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https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13775
It07:Limonene
2007-12-07T09:58:29Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]]<ref>[www.3dchem.com/imagesofmolecules/Limonene.jpg] www.3Dchem.com</ref> <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
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<ref>SciFinder</ref><br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, <ref>[http://www.biochemcorp.com/dlimonene2.htm] Biochem Corp. of Florida, Inc. </ref><br />
''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<ref>[http://www.lyondell.com/NR/rdonlyres/EF826DF8-B8CA-44F4-A475-7B218267B3C6/0/perfumebottle.jpg] Lyondell - A Leading Global Producer of Chemicals, Fuels and Plastics.</ref><br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma<ref>[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1470060] ehp Environmental Health Perspectives </ref> by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system <ref>[http://www.mskcc.org/mskcc/html/69206.cfm] Memorial Sloan-Kettering Cancer Centre </ref> in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] NIST Chemistry WebBook </ref><br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] NIST Chemistry WebBook </ref><br />
<br />
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<ref>SciFinder</ref><br />
<br />
== References ==<br />
<br />
<references/></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13538
It07:Limonene
2007-12-06T15:08:50Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]]<ref>[www.3dchem.com/imagesofmolecules/Limonene.jpg] www.3Dchem.com</ref> <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
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<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, <ref>[http://www.biochemcorp.com/dlimonene2.htm] Biochem Corp. of Florida, Inc. </ref><br />
''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<ref>[http://www.lyondell.com/NR/rdonlyres/EF826DF8-B8CA-44F4-A475-7B218267B3C6/0/perfumebottle.jpg] Lyondell - A Leading Global Producer of Chemicals, Fuels and Plastics.</ref><br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma<ref>[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1470060] ehp Environmental Health Perspectives </ref> by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system <ref>[http://www.mskcc.org/mskcc/html/69206.cfm] Memorial Sloan-Kettering Cancer Centre </ref> in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] NIST Chemistry WebBook </ref><br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] NIST Chemistry WebBook </ref><br />
<br />
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== References ==<br />
<br />
<references/></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13533
It07:Limonene
2007-12-06T15:04:44Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
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<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, <ref>[http://www.biochemcorp.com/dlimonene2.htm] Biochem Corp. of Florida, Inc. </ref><br />
''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<ref>[http://www.lyondell.com/NR/rdonlyres/EF826DF8-B8CA-44F4-A475-7B218267B3C6/0/perfumebottle.jpg] Lyondell - A Leading Global Producer of Chemicals, Fuels and Plastics.</ref><br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma<ref>[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1470060] ehp Environmental Health Perspectives </ref> by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system <ref>[http://www.mskcc.org/mskcc/html/69206.cfm] Memorial Sloan-Kettering Cancer Centre </ref> in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] NIST Chemistry WebBook </ref><br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] NIST Chemistry WebBook </ref><br />
<br />
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<br />
<br />
== References ==<br />
<br />
<references/></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13530
It07:Limonene
2007-12-06T15:02:49Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
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<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, <ref>[http://www.biochemcorp.com/dlimonene2.htm] Biochem Corp. of Florida, Inc. </ref><br />
''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<ref>[http://www.lyondell.com/NR/rdonlyres/EF826DF8-B8CA-44F4-A475-7B218267B3C6/0/perfumebottle.jpg] Lyondell - A Leading Global Producer of Chemicals, Fuels and Plastics.</ref><br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma<ref>[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1470060] ehp Environmental Health Perspectives </ref> by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system <ref>[http://www.mskcc.org/mskcc/html/69206.cfm] Memorial Sloan-Kettering Cancer Centre </ref> in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]] <ref>[http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=IR&Large=on] Memorial Sloan-Kettering Cancer Centre </ref><br />
<br />
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<br />
== References ==<br />
<br />
<references/></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13524
It07:Limonene
2007-12-06T14:59:44Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
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<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, <ref>[http://www.biochemcorp.com/dlimonene2.htm] Biochem Corp. of Florida, Inc. </ref><br />
''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<ref>[http://www.lyondell.com/NR/rdonlyres/EF826DF8-B8CA-44F4-A475-7B218267B3C6/0/perfumebottle.jpg] Lyondell - A Leading Global Producer of Chemicals, Fuels and Plastics.</ref><br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma<ref>[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1470060] ehp Environmental Health Perspectives </ref> by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system <ref>[http://www.mskcc.org/mskcc/html/69206.cfm] Memorial Sloan-Kettering Cancer Centre </ref> in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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<br />
== References ==<br />
<br />
<references/></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13501
It07:Limonene
2007-12-06T14:40:08Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
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0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
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-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
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M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<ref>[http://www.lyondell.com/NR/rdonlyres/EF826DF8-B8CA-44F4-A475-7B218267B3C6/0/perfumebottle.jpg] Lyondell - A Leading Global Producer of Chemicals, Fuels and Plastics.</ref><br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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<br />
== References ==<br />
<br />
<references/></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13482
It07:Limonene
2007-12-06T14:16:01Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
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M END<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
[[Image: enantiomers.gif]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Enantiomers.gif&diff=13481
File:Enantiomers.gif
2007-12-06T14:15:20Z
<p>Kb406: </p>
<hr />
<div></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13470
It07:Limonene
2007-12-06T14:06:50Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
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M END</inlineContents>Molecule-1<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]<br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13467
It07:Limonene
2007-12-06T14:05:55Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
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-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
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M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
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M END</inlineContents>Molecule-1<br />
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0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
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7 9 1 0 0 0<br />
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9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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<br />
<br />
<br />
'''L-limonene''' - the [S]-enantiomer, with a turpentine-like odour. <br />
[[Image:L-Limonene.jpg|200px|Limonene]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13463
It07:Limonene
2007-12-06T14:02:33Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-, Unitene, (L)-Limonene, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4S)-, alpha-Limonene, beta-Limonene<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
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0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
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0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
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M END<br />
</jmolApplet><br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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'''L-limonene'''<br />
[[Image:L-Limonene.jpg|200px|Limonene]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13458
It07:Limonene
2007-12-06T13:58:58Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
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9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
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M END</inlineContents>Molecule-1<br />
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9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outer portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98% ''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
<br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
[[Image: LimoneneMech.gif]]<br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
== ''Spectroscopy'' ==<br />
<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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<br />
<br />
<br />
'''L-limonene'''<br />
[[Image:L-Limonene.jpg|200px|Limonene]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13454
It07:Limonene
2007-12-06T13:54:17Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98%''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
[[Image: LimoneneEnantiomers.png]]<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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'''L-limonene'''<br />
[[Image:L-Limonene.jpg|200px|Limonene]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:LimoneneEnantiomers.png&diff=13452
File:LimoneneEnantiomers.png
2007-12-06T13:53:07Z
<p>Kb406: </p>
<hr />
<div></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13440
It07:Limonene
2007-12-06T13:39:59Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
<br />
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M END<br />
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M END<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98%''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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<title>Molecule-1</title><color>green</color><br />
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<br />
<br />
<br />
'''L-limonene'''<br />
[[Image:L-Limonene.jpg|200px|Limonene]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:L-Limonene.jpg&diff=13437
File:L-Limonene.jpg
2007-12-06T13:37:36Z
<p>Kb406: http://www.lyondell.com/Lyondell/Products/ByMarket/FoodAndBeverage/FlavorIngredients/LLimonenePandF/</p>
<hr />
<div>http://www.lyondell.com/Lyondell/Products/ByMarket/FoodAndBeverage/FlavorIngredients/LLimonenePandF/</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13435
It07:Limonene
2007-12-06T13:36:23Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
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<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is 90-98%''technical grade'' D-limonene, and the rest is a combination of other monoterpenes, such as 3-carene. Technical grade D-limonene has many applications in industrial products. In the 1980s, citrus limonene began to be used instead of common household cleaning solvents. D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene. Because it is biodegradable, it is even used as a solvent for silicones. <br />
Limonene may be used as a component in<br />
<br />
* graffiti remover<br />
* hand cleaner<br />
* car wash solution<br />
* industrial metal cleaner<br />
* recycling<br />
* insect repellent<br />
* dog and cat repellent<br />
<br />
There are other derivatives of limonene that are used in every day products, for example ''carvone'' is used in spearmint oil (found in dental care sweets and other products).<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13417
It07:Limonene
2007-12-06T12:35:56Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br />
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M END<br />
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<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is ''tenchical grade'' D-limonene, and has many applications in industrial products.<br />
D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene.<br />
Limonene may be used as a component in<br />
<br />
*graffiti remover<br />
*hand cleaner<br />
*car wash solution<br />
*industrial metal cleaner<br />
*recycling<br />
*(Said to also have an insectiside component)<br />
<br />
<br />
== ''Structure of Limonene'' ==<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13415
It07:Limonene
2007-12-06T12:30:16Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
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'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is ''tenchical grade'' D-limonene, and has many applications in industrial products.<br />
D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene.<br />
Limonene may be used as a component in<br />
<br />
*graffiti remover<br />
*hand cleaner<br />
*car wash solution<br />
*industrial metal cleaner<br />
*recycling<br />
*(Said to also have an insectiside component)<br />
<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13414
It07:Limonene
2007-12-06T12:25:47Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
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<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
<br />
== ''Uses of Limonene'' ==<br />
Nowadays, limonene is used in order to create an orange fragrance for various products, and it is also used in the formation of paint solids. D-limonene is divided into two components, ''food grade'' and ''technical grade''. WAhen the juice is extracted from the peel of the citrus fruit, the essential oils (mentioned above) are obtained from the juice by distillation. The final product is ''food grade'' D-limonene. This type of D-limonene is used primarily in certain consumer products. ''Technical grade'' D-limonene is obtained in a slightly different way, although a type of distillation is indeed used. A steam extractor is used to obtain the oil from the citrus fruit rind, and on condensation of the steam a layer of oil is left, floating on the water's surface. This is ''tenchical grade'' D-limonene, and has many applications in industrial products.<br />
D-limonene in itself is a solvent, and it can replace various other solvents such as toluene or mineral spirits. In the house, it may be added to a surfactant and diluted to replace many caustic cleaners, for example wipe=cleaners or sprays containe D-limonene.<br />
Limonene may be used as a component in<br />
<br />
- graffiti remover<br />
- hand cleaner<br />
- car wash solution<br />
- industrial metal cleaner<br />
- recycling<br />
- (Said to also have an insectiside component)<br />
<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13408
It07:Limonene
2007-12-06T12:03:24Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Limonene.jpg|200px|Limonene]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
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'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13407
It07:Limonene
2007-12-06T12:00:36Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| <br />
[α]20/D +115.5±1°, c = 10% in ethanol<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| http://physchem.ox.ac.uk/MSDS/LI/limonene.html <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| Respiratory, skin and eye irritant. Harmful if swallowed. <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
|}<br />
<br />
<br />
<br />
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<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13403
It07:Limonene
2007-12-06T11:54:04Z
<p>Kb406: /* ''Introduction'' */ addition of R and S phrases</p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| {{{Density}}} 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| {{{Rotation}}}°<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| {{{Hazards}}} <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[NFPA 704]]<br />
| {{{NFPA}}}<!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on "very dangerous" as default- adjust according to actual values --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: R10 R22 R36 R37 R38 <br /> [[List of S-phrases|S]]: S28 S37N S60 S61?<br />
|-<br />
| [[RTECS]] number<br />
| {{{RTECS}}}<br />
|-<br />
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]<br />
|-<br />
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]] <br />
| [http://en.wikipedia.org/wiki/Refractive_index ''1.47606''], <br />
|-<br />
|}<br />
<br />
<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, <br />
Carvene, Cinene, Dipentene, Efchole, <br />
p-mentha-1,8-diene, <br />
isopropenyl-1-methyl-1-cyclohexene, <br />
Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
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3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
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1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
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5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine.<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13174
It07:Limonene
2007-12-05T15:38:01Z
<p>Kb406: Beginning of table</p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] <!-- replace if not identical with the pagename --><br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| ''p''-mentha-1,8-diene or 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
| Other names<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>10</sub>H<sub>16</sub> <br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] <!-- mostly for organic compounds, omit otherwise --><br />
| CC(=C)[C@@H]1CCC(=CC1)C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 136.2 g/mol<br />
|-<br />
| Appearance<br />
| Light yellow liquid <br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 5989-27-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]<br />
| {{{Density}}} 0.841 g/cm³ <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| -96.9<sup>O</sup>C<!-- (mention any decomposition) --><br />
|-<br />
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]<br />
| 176<sup>O</sup>C<br />
|-<br />
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] <!-- (Only include this for chiral compounds, indicate direction/enantiomer combo if known) --><br />
| {{{Rotation}}}°<br />
|-<br />
! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information --><br />
|-<br />
| [[Material safety data sheet|MSDS]]<br />
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] <!-- please replace with proper link--><br />
|-<br />
| Main [[Worker safety and health|hazard]]s<br />
| {{{Hazards}}} <!-- e.g. highly toxic, explosive, flammable, corrosive --><br />
|-<br />
| [[NFPA 704]]<br />
| {{{NFPA}}}<!-- {{NFPA 704 | Health=4 | Flammability=4 | Reactivity=4 | Other=OX }} These are set on "very dangerous" as default- adjust according to actual values --><br />
|-<br />
| [[Flash point]]<br />
| 50°C<br />
|-<br />
| [[Risk and Safety Statements|R/S statement]]<br />
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?<br />
|-<br />
| [[RTECS]] number<br />
| {{{RTECS}}}<br />
|-<br />
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]<br />
|-<br />
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]] <br />
| [http://en.wikipedia.org/wiki/Refractive_index ''1.47606''], <br />
|-<br />
|}<br />
<br />
<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, <br />
Carvene, Cinene, Dipentene, Efchole, <br />
p-mentha-1,8-diene, <br />
isopropenyl-1-methyl-1-cyclohexene, <br />
Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
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-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
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9 10 1 0 0 0<br />
M END<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13160
It07:Limonene
2007-12-05T15:20:07Z
<p>Kb406: Table change</p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
{{Drug-Box |<br />
| Box_Name = Characteristics of Limonene<br />
| ImageFile = example_image.jpg<br />
| IUPACName = ''p''-mentha-1,8-diene or (R)-4-isopropenyl-1-methylcyclohexene<br />
| OtherName = Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, <br />
isopropenyl-1-methyl-1-cyclohexene, <br />
Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
| CAS_No = 5989-27-5<br />
| ATC_Code = <br />
| PubChem = <br />
| SMILES = surround in nowiki script code '<' nowiki'>' CC(=C)[C@@H]1CCC(=CC1)C'</'nowiki'>'<br />
| Formula = C<sub>10</sub>H<sub>16</sub><br />
| MolarMass = 136.2 gmol<sub>-1</sub><br />
| Boiling Point = 176<sup>O</sup>C<br />
| Melting Point = -96.9<sup>O</sup>C<br />
| Density = <br />
| Flash Point = 43<sup>O</sup>C<br />
| Excretion = <br />
| Pregnancy_cat = <br />
| Legal_status = <br />
| Routes = <br />
}}<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, <br />
Carvene, Cinene, Dipentene, Efchole, <br />
p-mentha-1,8-diene, <br />
isopropenyl-1-methyl-1-cyclohexene, <br />
Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
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<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
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<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13147
It07:Limonene
2007-12-05T15:08:29Z
<p>Kb406: </p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, <br />
Carvene, Cinene, Dipentene, Efchole, <br />
p-mentha-1,8-diene, <br />
isopropenyl-1-methyl-1-cyclohexene, <br />
Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, <br />
1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
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M END<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13144
It07:Limonene
2007-12-05T15:05:51Z
<p>Kb406: Addition of Mechanism</p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
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M END<br />
title1<br />
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M END</inlineContents>Molecule-1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
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M END<br />
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<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
== ''Mechanism of Formation'' ==<br />
<br />
<br />
[[Image: LimoneneMech.gif]]<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene, isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, 1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
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<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:LimoneneMech.gif&diff=13142
File:LimoneneMech.gif
2007-12-05T15:04:20Z
<p>Kb406: ChemDraw: Synthesis of Limonene</p>
<hr />
<div>ChemDraw: Synthesis of Limonene</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13119
It07:Limonene
2007-12-05T14:28:05Z
<p>Kb406: Altering headlines</p>
<hr />
<div>=== '''Limonene''' ===<br />
<br />
== ''Introduction'' ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
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0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
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M END<br />
title1<br />
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-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
== ''Medicinal Properties'' ==<br />
<br />
<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene, isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, 1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
== ''Spectroscopy'' ==<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
<size>200</size><br />
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=13114
It07:Limonene
2007-12-05T14:24:52Z
<p>Kb406: Addition to Medicinal Properties</p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
'''Medicinal Properties'''<br />
D-Limonene is used as a supplement to treat and prevent cancer. As described above, D-limonene is a ‘‘terpene’’, specifically a ‘‘‘cyclic monoterpene’’’. These structures lead to an alteration of a gene expression, from the prevention of the isoprenylation of G proteins. The result of this is a G1 cell cycle arrest, apoptosis (a type of PCD, or Programmed Cell Death), and eventually the replacement of tumor parenchyma by stromal (organ framework) elements, which are predominantly made of connective tissue. Monoterpenes prevent the carcinogenesis process during all the stages, and are thought to be efficient in treating cancers in all periods. D-Limonene metabolises, after oral administration, to form limonene-1,2-diol, dihydroperillic acid, perillic acid and uroterpenol, all of which have the same effects outlined as above. <br />
Limonene also promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene, isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, 1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
<size>200</size><br />
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12910
It07:Limonene
2007-12-04T17:10:55Z
<p>Kb406: Addition of Medicinal Properties</p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
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4 5 1 0 0 0<br />
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8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene''' is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
'''Medicinal Properties'''<br />
Limonene is said to have anti-cancer effects, according to various studies. Limonene promotes the Gluthione-S-transferase (GST) system in the small bowel and liver, which detoxifies carcinogens (cancer-promoting substance, for example benzopyrene, found in cigarette smoke). <br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene, isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, 1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12909
It07:Limonene
2007-12-04T17:00:28Z
<p>Kb406: Addition to table</p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
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8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+'''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 <br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isopropenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene, isopropenyl-1-methyl-1-cyclohexene, Dextro-limonene, (R)-Limonene, (R)-(+)-Limonene, 1-methyl-4-(1-methylethenyl)-<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Registry Number''<br />
| 5989-27-5<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
<size>200</size><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12908
It07:Limonene
2007-12-04T16:53:53Z
<p>Kb406: </p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
<size>200</size><br />
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12907
It07:Limonene
2007-12-04T16:51:59Z
<p>Kb406: Addition of IR Spectrum</p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif|Mass Spectrum of Limonene]]<br />
<br />
[[Image:IR Spectrum of Limonene.gif|Infrared Spectrum of Limonene]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
<size>200</size><br />
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12906
It07:Limonene
2007-12-04T16:40:54Z
<p>Kb406: </p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
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5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
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5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Sci3d138-86-3;.mol&diff=12905
File:Sci3d138-86-3;.mol
2007-12-04T16:40:03Z
<p>Kb406: </p>
<hr />
<div></div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12902
It07:Limonene
2007-12-04T16:32:36Z
<p>Kb406: </p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
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M END<br />
title1<br />
title2<br />
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-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
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<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
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8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
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<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12900
It07:Limonene
2007-12-04T16:30:21Z
<p>Kb406: Ball-and-stick</p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
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9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
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9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<title>Molecule-1</title><color>green</color><br />
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Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12894
It07:Limonene
2007-12-04T16:22:59Z
<p>Kb406: Changing structure of page</p>
<hr />
<div>== Limonene ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
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M END<br />
title1<br />
title2<br />
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-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
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M END<br />
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</jmol><br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
<br />
<br />
<br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|-<br />
! ''Refractive Index''<br />
| 1.47606 at 14.4<sup>O</sup>C<br />
|-<br />
! ''Flash Point''<br />
| 119.0<sup>O</sup>F<br />
|-<br />
! ''Melting Point''<br />
| -142.4<sup>O</sup>F<br />
|-<br />
! ''Specific Gravity''<br />
| 0.8411 at 68.0<sup>O</sup>F<br />
|}<br />
<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12876
It07:Limonene
2007-12-04T16:03:04Z
<p>Kb406: Formation of Limonene</p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
[[Image: Formation_of_Limonene.png]]<br />
<br />
<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
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M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
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1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|}<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Formation_of_Limonene.png&diff=12875
File:Formation of Limonene.png
2007-12-04T16:02:05Z
<p>Kb406: ChemDraw</p>
<hr />
<div>ChemDraw</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12874
It07:Limonene
2007-12-04T16:01:41Z
<p>Kb406: Addition to intro</p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. Specifically, limonene is found in abundance in the oil sacs of the rind, which may be located in the flavedo, coloured or outr portion of the peel. D-Limonene takes up 90-95% of the oil, in citrus fruits. It is also found in the oils of pine trees.<br />
The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. Many everyday household products, for example fruit juices or spices, contain essential oils which are part of the ''terpene'' family. The common structural characteristic of all terpenes is that they generally contain at least five, or multiples of five carbon atoms, joined together in this fashion:<br />
<br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
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5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
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1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
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4 5 1 0 0 0<br />
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5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|}<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12851
It07:Limonene
2007-12-04T15:33:34Z
<p>Kb406: </p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
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5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! ''Appearance''<br />
| Light yellow liquid<br />
|}<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12850
It07:Limonene
2007-12-04T15:33:02Z
<p>Kb406: </p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! Appearance''<br />
| ''Light yellow liquid''<br />
|}<br />
<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12849
It07:Limonene
2007-12-04T15:31:39Z
<p>Kb406: Addition to table</p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|-<br />
! ''CAS Number''<br />
| 138-86-6<br />
|-<br />
! ''Specific Gravity''<br />
| 0.84<br />
|-<br />
! Appearance''<br />
| Light yellow liquid<br />
|}<br />
<br />
'''Spectroscopy'''<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12845
It07:Limonene
2007-12-04T15:26:27Z
<p>Kb406: Table</p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole, p-mentha-1,8-diene<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|-<br />
! ''Boiling Point''<br />
| 176<sup>O</sup>C<br />
|}<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12840
It07:Limonene
2007-12-04T15:22:10Z
<p>Kb406: Mass Spec Limonene</p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|}<br />
[[Image:Mass_Spec_Limonene.gif]]</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Mass_Spec_Limonene.gif&diff=12837
File:Mass Spec Limonene.gif
2007-12-04T15:21:18Z
<p>Kb406: http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=Mass&Large=on</p>
<hr />
<div>http://webbook.nist.gov/cgi/cbook.cgi?Spec=C5989275&Index=0&Type=Mass&Large=on</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12836
It07:Limonene
2007-12-04T15:20:52Z
<p>Kb406: </p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|}</div>
Kb406
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Limonene&diff=12833
It07:Limonene
2007-12-04T15:18:22Z
<p>Kb406: Upload IR Spectrum</p>
<hr />
<div>== Limonene ==<br />
<br />
<br />
'''Limonene'''is found in abundance in the essential oils of citrus fruits (hence the name ''limon''ene, which derived from lemon rind), particularly in orange and lemon peel. It is also found in the oils of pine trees. The molecule is a hydrocarbon, with the molecular formula C<sub>10</sub>H<sub>16</sub>, and it is specifically a ''terpene''. <br />
The molecule is chiral, which means that it exists as two enantiomers with different characteristics. D-limonene, the (R)-enantiomer, has an orange scent and L-limonene, the (S)-enantiomer, has a smell reminscent of turpentine. <br />
[[Image:orange-04limo.gif |thumb|right|200|Description of image]]<br />
<br />
[[Image:limonene.jpg|thumb|right|200|Description of image]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>orange</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
title1<br />
title2<br />
3 2 0 0 0 1 V2000<br />
-1.0400 1.5290 0.0000 O 0 0 0 0 0<br />
-1.0331 2.4710 0.0000 H 0 0 0 0 0<br />
-1.9535 1.2993 0.0000 H 0 0 0 0 0<br />
1 2 1 0 0 0<br />
1 3 1 0 0 0<br />
M END</inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
10 10 0 0 0 0 0 0 0 0999 V2000<br />
1.7064 -0.0612 0.1042 C 0 0 0 0 0 0 0 0 0 1<br />
3.0650 -0.6993 0.0549 C 0 0 0 0 0 0 0 0 0 2<br />
1.5859 1.2574 -0.0357 C 0 0 0 0 0 0 0 0 0 3<br />
0.4856 -0.9089 0.3104 C 0 0 0 0 0 0 0 0 0 4<br />
-0.7389 -0.3001 -0.3371 C 0 0 0 0 0 0 0 0 0 5<br />
0.7262 -2.3210 -0.2286 C 0 0 0 0 0 0 0 0 0 6<br />
-1.9681 -1.1169 0.1048 C 0 0 0 0 0 0 0 0 0 7<br />
-0.5240 -3.1520 -0.1294 C 0 0 0 0 0 0 0 0 0 8<br />
-1.7410 -2.6169 0.0230 C 0 0 0 0 0 0 0 0 0 9<br />
-2.9242 -3.5335 0.1357 C 0 0 0 0 0 0 0 0 0 10<br />
1 2 1 0 0 0<br />
1 3 2 0 0 0<br />
1 4 1 0 0 0<br />
4 5 1 0 0 0<br />
4 6 1 0 0 0<br />
5 7 1 0 0 0<br />
6 8 1 0 0 0<br />
7 9 1 0 0 0<br />
8 9 2 0 0 0<br />
9 10 1 0 0 0<br />
M END<br />
</jmolApplet><br />
</jmol><br />
<br />
{| border="1"<br />
|+ '''Characteristics of Limonene'''<br />
! Column heading 1 !! Column heading 2 !! Column heading 3<br />
|-<br />
! ''Chemical Name''<br />
| 4-isopropenyl-1-methylcyclohexene<br />
|-<br />
! ''Chemical Synonyms''<br />
| Methyl-4-isoproenyl cyclohexene, Cajaputene, Carvene, Cinene, Dipentene, Efchole<br />
|-<br />
! ''Chemical Formula''<br />
| C<sub>10</sub>H<sub>16</sub><br />
|}<br />
<br />
[[Image:IR_Spectrum_of_Limonene.gif]]</div>
Kb406