https://chemwiki.ch.ic.ac.uk/api.php?action=feedcontributions&feedformat=atom&user=Hmg05ChemWiki - User contributions [en]2026-05-21T13:40:43ZUser contributionsMediaWiki 1.43.0https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7224It:Cinnamaldehyde2006-12-06T16:27:17Z<p>Hmg05: /* Notes */ Added References</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<sup>4</sup><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<sup>6</sup><br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<sup>7</sup><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.<sup>8</sup><br />
<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<sup>9</sup><br />
<br />
==Notes==<br />
<br />
1. [http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm| Chemical Land21-Cinnamaldehyde Information Page]<br />
<br />
2. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
3. GB Patent 504125 (1939 to I. G. Farben)<br />
<br />
4. Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)<br />
<br />
5. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
6. Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20<br />
<br />
7. WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Bioresour. technol., 2005, vol. 96, no7, pp. 813-818<br />
<br />
8. [http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm EPA Pesticide Factsheet for Cinnamaldehyde]<br />
<br />
9. http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART<br />
<br />
MSDS Resources:<br />
<br />
10.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
11.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7222It:Cinnamaldehyde2006-12-06T16:25:44Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<sup>4</sup><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<sup>6</sup><br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<sup>7</sup><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.<sup>8</sup><br />
<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<sup>9</sup><br />
<br />
==Notes==<br />
<br />
1. [http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm| Chemical Land21-Cinnamaldehyde Information Page]<br />
<br />
2. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
3. GB Patent 504125 (1939 to I. G. Farben)<br />
<br />
4. Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)<br />
<br />
5. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
6. Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20<br />
<br />
7. WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Bioresour. technol., 2005, vol. 96, no7, pp. 813-818<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7218It:Cinnamaldehyde2006-12-06T16:23:44Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<sup>4</sup><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<sup>6</sup><br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<sup>7</sup><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<br />
1. [http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm| Chemical Land21-Cinnamaldehyde Information Page]<br />
<br />
2. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
3. GB Patent 504125 (1939 to I. G. Farben)<br />
<br />
4. Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)<br />
<br />
5. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
6. Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20<br />
<br />
7. WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Bioresour. technol., 2005, vol. 96, no7, pp. 813-818<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7215It:Cinnamaldehyde2006-12-06T16:22:34Z<p>Hmg05: /* Antimicrobial Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<sup>4</sup><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<sup>6</sup><br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<sup>7</sup><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<br />
1. [http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm| Chemical Land21-Cinnamaldehyde Information Page]<br />
<br />
2. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
3. GB Patent 504125 (1939 to I. G. Farben)<br />
<br />
4. Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)<br />
<br />
5. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7214It:Cinnamaldehyde2006-12-06T16:20:40Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<sup>4</sup><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<br />
1. [http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm| Chemical Land21-Cinnamaldehyde Information Page]<br />
<br />
2. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
3. GB Patent 504125 (1939 to I. G. Farben)<br />
<br />
4. Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)<br />
<br />
5. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7211It:Cinnamaldehyde2006-12-06T16:18:32Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<br />
1. [http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm| Chemical Land21-Cinnamaldehyde Information Page]<br />
<br />
2. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
3. GB Patent 504125 (1939 to I. G. Farben)<br />
<br />
4. Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)<br />
<br />
5. Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)<br />
<br />
<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7209It:Cinnamaldehyde2006-12-06T16:14:36Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%<sup>5</sup> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7207It:Cinnamaldehyde2006-12-06T16:13:40Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7206It:Cinnamaldehyde2006-12-06T16:13:30Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7204It:Cinnamaldehyde2006-12-06T16:12:58Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde<sup>2</sup>; condensation of styrene and formyl methylaniline<sup>3</sup>; and oxidation of the primary alcohol cinnamyl alcohol<sup>4</sup><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7198It:Cinnamaldehyde2006-12-06T16:00:59Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents.[http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm]<br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7195It:Cinnamaldehyde2006-12-06T15:53:24Z<p>Hmg05: /* Chemical Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.[http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm]<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7188It:Cinnamaldehyde2006-12-06T15:43:55Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.<ref>http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm</ref><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unforeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7165It:Cinnamaldehyde2006-12-06T15:18:48Z<p>Hmg05: /* Antimicrobial Properties */ Added Antifungal Properties Paragraph and References</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.<ref>http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm</ref><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
'''Antifungal Properties'''<br />
<br />
Cinnamaldehyde has also been found to exhibit antifungal properties, and of all the leaf oils of the Cinnamonuium tree, possesses the strongest of these against some strains of fungi (such as Coriolus versicolor and Laetiporus sulphureus).<ref>WANG Sheng-Yang, CHEN Pin-Fun , CHANG Shang-Tzen: Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi, Bioresour. technol., 2005, vol. 96, no7, pp. 813-818</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7154It:Cinnamaldehyde2006-12-06T15:08:30Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.<ref>http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm</ref><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7153It:Cinnamaldehyde2006-12-06T15:07:52Z<p>Hmg05: /* Antimicrobial Properties */ Added Graph and reference</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.<ref>http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm</ref><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg|thumb|400px|left|Effect of eugenol and cinnamaldehyde on the growth of H. pylori (ATCC26695) at low pH.]][http://www.ann-clinmicrob.com/content/4/1/20 Annals of Clinical Microbiology and Antimicrobials 2005, 4:20 doi:10.1186/1476-0711-4-20 ... 2005 Ali et al]<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7149It:Cinnamaldehyde2006-12-06T14:58:44Z<p>Hmg05: /* Antimicrobial Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.<ref>http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm</ref><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
<br />
[[Image:1476-0711-4-20-4.jpg]]<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=File:1476-0711-4-20-4.jpg&diff=7147File:1476-0711-4-20-4.jpg2006-12-06T14:57:04Z<p>Hmg05: </p>
<hr />
<div></div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=7063It:Cinnamaldehyde2006-12-06T12:43:55Z<p>Hmg05: /* Chemical Properties */ Added Properties paragraph and ref.</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
<br />
Cinnamaldehyde is a planar acrylic aldehyde with a benzene ring substituent. Its geometry arises from the presence of the double bond and the aromatic benzene ring. Cis and trans isomers both exist, although the predominant form is the trans isomer, where the terminal carbonyl group is on the opposite side of the benzene ring over the rigid double bond.<ref>http://www.chemicalland21.com/specialtychem/perchem/CINNAMALDEHYDE.htm</ref><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6995It:Cinnamaldehyde2006-12-05T15:48:42Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effective in this area: namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6994It:Cinnamaldehyde2006-12-05T15:47:47Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme for this synthesis follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6943It:Cinnamaldehyde2006-12-05T12:48:38Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Chemical Properties==<br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6941It:Cinnamaldehyde2006-12-05T12:47:09Z<p>Hmg05: /* Introduction */ Added Spectra to chembox</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Spectral Data<br />
|-<br />
|Spectra<br />
|[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=UVVis&Large=on UV/Vis], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=0&Type=Mass&Large=on Mass], [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C104552&Index=1&Type=IR&Large=on IR]<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6910It:Cinnamaldehyde2006-12-05T11:53:55Z<p>Hmg05: /* Synthesis */ added reaction scheme</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme follows: <br />
<br />
<br />
<br />
[[Image:Cinnamaldehyde.gif]]<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Cinnamaldehyde.gif&diff=6909File:Cinnamaldehyde.gif2006-12-05T11:52:49Z<p>Hmg05: </p>
<hr />
<div></div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Reaction_scheme.gif&diff=6901File:Reaction scheme.gif2006-12-05T11:40:16Z<p>Hmg05: </p>
<hr />
<div></div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6691It:Cinnamaldehyde2006-12-03T17:51:08Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
'''Synthesis by Aldol Condensation of Benzaldehyde and Acetaldehyde'''<br />
This involves reacting benzaldehyde with acetaldehyde in aqueous NaOH with a benzene catalyst, with an optimum yield of 57%.<ref>Qufu Shifan Daxue Xuebao, Ziran Kexueban, 31(2) 96-98, (2005)</ref> A reaction scheme follows: <br />
<br />
<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6690It:Cinnamaldehyde2006-12-03T17:16:20Z<p>Hmg05: /* Antimicrobial Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Peine, ''Ber'', '''17''', 2117, (1884)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows: safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6689It:Cinnamaldehyde2006-12-03T17:15:37Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Peine, ''Ber'', '''17''', 2117, (1884)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows, safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6688It:Cinnamaldehyde2006-12-03T17:15:25Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Peine, ''Ber'', '''17''', 2117, (1884)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows, safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
1.[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
2.[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6687It:Cinnamaldehyde2006-12-03T17:15:04Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Peine, ''Ber'', '''17''', 2117, (1884)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows, safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6686It:Cinnamaldehyde2006-12-03T17:14:24Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde;<ref>Peine, ''Ber'', '''17''', 2117, (1884)</ref> condensation of styrene and formyl methylaniline;<ref>GB 504125 (1939 to I. G. Farben</ref> and oxidation of the primary alcohol cinnamyl alcohol.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
<br />
'''Synthesis by oxidation of cinnamyl alcohol'''<br />
<br />
The alcohol is usually oxidised by an agent such as a chromium(VI) oxide-pyridine complex, which has been shown to be effective at oxidation at room temperature and selective towards the alcohol group rather than the double bond present. This method results in yield of 81% of the product.<ref>Study of the Chromium(VI) Oxide-Pyridine Complex, Holum J. R., 26, 4814 (1961)</ref><br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows, safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6685It:Cinnamaldehyde2006-12-03T15:54:24Z<p>Hmg05: /* Antimicrobial Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the antibiotic resistance of this bacterium grows, safe and non-antibiotic methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6477It:Cinnamaldehyde2006-11-30T18:00:52Z<p>Hmg05: /* Antimicrobial Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
Recent studies have shown that cinnamaldehyde has antimicrobial properties, particularly against the human gastric pathogen Helicobacter pylori, which is a major factor in many gastronomic diseases. It was found that cinnamaldehyde (along with eugenol) was effective in inhibiting all strains of H. pylori, increasing effectiveness at acidic pH. Furthermore, no resistance to this compound was seen even after 10 doses. This is of particular importance as the resistance to antibiotics of this (and many other) bacterium grows, non-antibiotic, safe methods of eradication are required.<ref>Annals of Clinical Microbiology and Antimicrobials, 2005, 4:20</ref><br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6476It:Cinnamaldehyde2006-11-30T17:35:50Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<references/><br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6475It:Cinnamaldehyde2006-11-30T17:34:13Z<p>Hmg05: /* Notes */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
</references><br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6474It:Cinnamaldehyde2006-11-30T17:33:59Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-in/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6473It:Cinnamaldehyde2006-11-30T17:30:37Z<p>Hmg05: /* References */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-bin/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==Notes==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6472It:Cinnamaldehyde2006-11-30T17:21:17Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides. It has shown particular effectiveness in its uses as an antifungal agent, corn rootworm attractant and a dog and cat repellent. It has become increasingly popular due to its lack of unfroeseen adversable effects to humans, non-target organisms and the environment. In addition, its status as a natural extract makes it less expensive to register under the US Environmental Protection Agency due to relaxed regulations regarding natural product based repellents. <br />
<br />
Its use as a bird repellent has been considered, as it contains many of the chemical properties regarded as effetive in this area namely its planar structure; posession of a benxene ring; and its weak basicity at the carbonyl oxygen. However, studies showed that it lost effectiveness after the first day of the trial, suggesting that its potency is not sufficient for sustained use as a bird repellent.<ref>http://www3.interscience.wiley.com/cgi-bin/fulltext/63003418/PDFSTART</ref><br />
<br />
http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm<br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6469It:Cinnamaldehyde2006-11-30T16:49:39Z<p>Hmg05: /* Synthesis */ Added Introductory Paragraph</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although the majority of cinnamaldehyde is obtained from the steam distillation of twigs and leaves from the Cinnamonium tree, several synthetic methods have been devised. The most common of these are: by condensation of benzaldehyde and acetaldehyde; condensation of styrene and formyl methylaniline; and oxidation of the primary alcohol cinnamyl alcohol.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides.<br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6465It:Cinnamaldehyde2006-11-30T16:30:09Z<p>Hmg05: /* Pesticidal Properties */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although Cinnamaldehyde can be made synthetically, the more convenient method is steam distillation of the leaves of the Cinnamonium tree.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
Cinnamaldehyde has been increasingly used as an alternative to conventional pesticides.<br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6457It:Cinnamaldehyde2006-11-30T16:07:41Z<p>Hmg05: /* Synthesis */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although Cinnamaldehyde can be made synthetically, the more convenient method is steam distillation of the leaves of the Cinnamonium tree.<br />
<br />
==Antimicrobial Properties==<br />
<br />
==Pesticidal Properties==<br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=6456It:Cinnamaldehyde2006-11-30T16:03:51Z<p>Hmg05: /* Introduction */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Synthesis==<br />
<br />
Although Cinnamaldehyde can be made synthetically, the more convenient method is steam distillation of the leaves of the Cinnamonium tree.<br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=5585It:Cinnamaldehyde2006-11-20T14:02:59Z<p>Hmg05: /* Introduction */</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=5580It:Cinnamaldehyde2006-11-20T13:58:37Z<p>Hmg05: /* Introduction */ added jmol diagram</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|{{R36/37/38}}-{{R43}}<br />
|-<br />
|Safety Phrases<br />
|{{R26}}-{{R36/37}}<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Nov-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Nov-06 0 NONE 4<br />
ATOM 1 O 0 -4.127 -0.498 -0.001 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.228 0.319 -0.000 0.00 0.00 C+0<br />
ATOM 3 H 0 -3.458 1.375 0.005 0.00 0.00 H+0<br />
ATOM 4 C 0 -1.885 -0.110 -0.001 0.00 0.00 C+0<br />
ATOM 5 C 0 -0.884 0.800 0.000 0.00 0.00 C+0<br />
ATOM 6 C 0 0.517 0.352 -0.001 0.00 0.00 C+0<br />
ATOM 7 C 0 1.555 1.290 0.000 0.00 0.00 C+0<br />
ATOM 8 C 0 2.866 0.862 -0.000 0.00 0.00 C+0<br />
ATOM 9 C 0 3.156 -0.491 -0.001 0.00 0.00 C+0<br />
ATOM 10 C 0 2.134 -1.426 -0.002 0.00 0.00 C+0<br />
ATOM 11 C 0 0.819 -1.014 0.004 0.00 0.00 C+0<br />
ATOM 12 H 0 -1.656 -1.166 -0.002 0.00 0.00 H+0<br />
ATOM 13 H 0 -1.113 1.855 0.001 0.00 0.00 H+0<br />
ATOM 14 H 0 1.331 2.347 0.000 0.00 0.00 H+0<br />
ATOM 15 H 0 3.668 1.585 0.000 0.00 0.00 H+0<br />
ATOM 16 H 0 4.184 -0.820 -0.001 0.00 0.00 H+0<br />
ATOM 17 H 0 2.369 -2.480 -0.002 0.00 0.00 H+0<br />
ATOM 18 H 0 0.023 -1.744 0.004 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 23<br />
CONECT 2 1 3 4 0 NONE 24<br />
CONECT 4 2 5 12 0 NONE 25<br />
CONECT 5 4 6 13 0 NONE 26<br />
CONECT 6 5 11 7 0 NONE 27<br />
CONECT 7 6 8 14 0 NONE 28<br />
CONECT 8 7 9 15 0 NONE 29<br />
CONECT 9 8 10 16 0 NONE 30<br />
CONECT 10 9 11 17 0 NONE 31<br />
CONECT 11 10 6 18 0 NONE 32<br />
END NONE 33<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:projects&diff=5576It:projects2006-11-20T13:29:35Z<p>Hmg05: /* Supplemental Project Page */</p>
<hr />
<div>__FORCETOC__<br />
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| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]<br />
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| bgcolor="#CCFF00" |02<br />
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]<br />
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<br />
----<br />
[[Template:Chem-Data]]<br />
<br />
[[Template:Chembox supplement]] - to be linked to from the supplementary section of the table in the template above, for usage see [[Template_talk:chembox_supplement|here]]<br />
<br />
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<br />
[[R & S Phrases]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=5322It:Cinnamaldehyde2006-11-12T16:01:01Z<p>Hmg05: /* Cinnamaldehyde */ Added to introduction</p>
<hr />
<div>==Introduction==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|36/37/38-43<br />
|-<br />
|Safety Phrases<br />
|26-36/37<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.<br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=5321It:Cinnamaldehyde2006-11-12T15:47:53Z<p>Hmg05: /* Cinnamaldehyde */</p>
<hr />
<div>==Cinnamaldehyde==<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|36/37/38-43<br />
|-<br />
|Safety Phrases<br />
|26-36/37<br />
|}<br />
<br />
'''Cinnamaldehyde''' is an unsaturated [[aldehyde]] found in the bark of the [[Cinnamomum zeylanicum]] tree. Due to its distinctive flavour and aroma, it is a common component of among others, many foodstuffs, perfumes, and detergents. <br />
<br />
==References==<br />
<br />
[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]<br />
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=5320It:Cinnamaldehyde2006-11-12T15:40:19Z<p>Hmg05: /* Cinnamaldehyde */ Improved chembox</p>
<hr />
<div>==Cinnamaldehyde==<br />
<br />
Cinnamaldehyde is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. Due to its distinctive flavour and aroma, it is a common component of among others, many foodstuffs, perfumes, and detergents.<br />
<br />
{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"<br />
<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
| [[Chemical Formula|Molecular Formula]]<br />
|C6H5CH:CHCHO <br />
|-<br />
|[[Molar Mass]]<br />
|132.16<br />
|-<br />
|[[Simplified molecular input line entry specification|SMILES]]<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|[[CAS Registry Number|CAS Number]]<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|[[Melting Point]] <br />
|-7<sub>o</sub>C<br />
|-<br />
|[[Boiling Point]]<br />
|248 °C(lit.)<br />
|-<br />
|[[Flash Point]]<br />
|160 F<br />
|-<br />
|[[Density]]<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|36/37/38-43<br />
|-<br />
|Safety Phrases<br />
|26-36/37<br />
|}</div>Hmg05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Cinnamaldehyde&diff=5319It:Cinnamaldehyde2006-11-12T15:33:05Z<p>Hmg05: Entered chem box</p>
<hr />
<div>==Cinnamaldehyde==<br />
<br />
Cinnamaldehyde is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. Due to its distinctive flavour and aroma, it is a common component of among others, many foodstuffs, perfumes, and detergents.<br />
<br />
{| class="infobox"<br />
! {{chembox header}} | Cinnamaldehyde<br />
|-<br />
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [[IUPAC nomenclature|Systematic name]]<br />
|3-phenyl-2-propenal<br />
|-<br />
| Other names<br />
|trans-cinnamaldehyde, <br />
cinnamic aldehyde, <br />
trans-cinnamic aldehyde <br />
|-<br />
|Physical Appearance<br />
|Yellow oily liquid<br />
|-<br />
|Molecular Formula<br />
|C6H5CH:CHCHO <br />
|-<br />
|Molecular Mass<br />
|132.16<br />
|-<br />
|SMILES String<br />
|O=C([H])/C=C/C1=CC=CC=C1<br />
|-<br />
|CAS Registry Number<br />
|104-55-2<br />
|-<br />
! {{chembox header}} |Pysical Properties<br />
|-<br />
|Melting Point <br />
|-7<sub>o</sub>C<br />
|-<br />
|Boiling Point<br />
|248 °C(lit.)<br />
|-<br />
|Flash Point<br />
|160 F<br />
|-<br />
|Density<br />
|1.05 g/mL at 25 °C(lit.)<br />
|-<br />
|Refractive Index (n20/D)<br />
|1.621(lit.)<br />
|-<br />
|Vapour Density<br />
|4.5 (air = 1) <br />
|-<br />
|Vapour Pressure<br />
|0.02 mm Hg at 20 C<br />
|-<br />
|Solubility<br />
|Slight in water<br />
|-<br />
! {{chembox header}} | Stability<br />
|-<br />
|Stability<br />
|Stable, but combustible. Incompatible<br />
with strong bases and oxidising agents.<br />
|-<br />
! {{chembox header}} | Hazards and Safety<br />
|-<br />
|Hazard Codes<br />
| Xi<br />
|-<br />
|Risk Phrases<br />
|36/37/38-43<br />
|-<br />
|Safety Phrases<br />
|26-36/37<br />
|}</div>Hmg05