2006-10-31T14:29:24Z

Bg105: added reference

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D Structure of Zingerone
|-
| align="center" colspan="3" bgcolour="#ffffff" | [[Image:Untitled.gif]]
|-
! {{chembox header}} colspan="3" |3D structure of Zingerone <jmol>
<jmolApplet>
<size>200</size>
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<inlineContents>
HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 O 0 3.909 -1.039 -0.489 0.00 0.00 O+0
ATOM 2 C 0 2.599 -0.845 -0.181 0.00 0.00 C+0
ATOM 3 C 0 2.106 0.445 -0.009 0.00 0.00 C+0
ATOM 4 O 0 2.934 1.515 -0.149 0.00 0.00 O+0
ATOM 5 C 0 2.143 2.682 0.086 0.00 0.00 C+0
ATOM 6 C 0 0.770 0.636 0.305 0.00 0.00 C+0
ATOM 7 C 0 -0.070 -0.452 0.446 0.00 0.00 C+0
ATOM 8 C 0 -1.523 -0.242 0.787 0.00 0.00 C+0
ATOM 9 C 0 -2.335 -0.105 -0.502 0.00 0.00 C+0
ATOM 10 C 0 -3.788 0.105 -0.161 0.00 0.00 C+0
ATOM 11 C 0 -4.804 0.269 -1.261 0.00 0.00 C+0
ATOM 12 O 0 -4.137 0.142 0.995 0.00 0.00 O+0
ATOM 13 C 0 0.419 -1.734 0.275 0.00 0.00 C+0
ATOM 14 C 0 1.750 -1.932 -0.044 0.00 0.00 C+0
ATOM 15 H 0 4.384 -1.120 0.349 0.00 0.00 H+0
ATOM 16 H 0 1.331 2.723 -0.641 0.00 0.00 H+0
ATOM 17 H 0 1.728 2.643 1.093 0.00 0.00 H+0
ATOM 18 H 0 2.767 3.570 -0.016 0.00 0.00 H+0
ATOM 19 H 0 0.385 1.637 0.439 0.00 0.00 H+0
ATOM 20 H 0 -1.889 -1.094 1.359 0.00 0.00 H+0
ATOM 21 H 0 -1.629 0.666 1.381 0.00 0.00 H+0
ATOM 22 H 0 -1.969 0.747 -1.074 0.00 0.00 H+0
ATOM 23 H 0 -2.229 -1.013 -1.096 0.00 0.00 H+0
ATOM 24 H 0 -4.306 0.208 -2.228 0.00 0.00 H+0
ATOM 25 H 0 -5.551 -0.521 -1.186 0.00 0.00 H+0
ATOM 26 H 0 -5.291 1.240 -1.164 0.00 0.00 H+0
ATOM 27 H 0 -0.240 -2.582 0.386 0.00 0.00 H+0
ATOM 28 H 0 2.130 -2.934 -0.178 0.00 0.00 H+0
CONECT 1 2 15 0 0 NONE 33
CONECT 2 1 14 3 0 NONE 34
CONECT 3 2 4 6 0 NONE 35
CONECT 4 3 5 0 0 NONE 36
CONECT 5 4 16 17 18 NONE 37
CONECT 6 3 7 19 0 NONE 38
CONECT 7 6 8 13 0 NONE 39
CONECT 8 7 9 20 21 NONE 40
CONECT 9 8 10 22 23 NONE 41
CONECT 10 9 11 12 0 NONE 42
CONECT 11 10 24 25 26 NONE 43
CONECT 12 10 0 0 0 NONE 44
CONECT 13 7 14 27 0 NONE 45
CONECT 14 13 2 28 0 NONE 46
END NONE 47
</inlineContents>
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</jmol>
|-
! {{chembox header}} colspan="3" | Properties
|-
| colspan="1" |IUPAC Systematic Name
| colspan="2"|4-(4-hydroxy-3-methoxyphenyl)-2-butanone
|-
| colspan="1" |Molecular formula
| colspan="2" |C<sub>11</sub>H<sub>14</sub>O<sub>3</sub>
|-
| colspan="1" |SMILES String
| colspan="2" |OC1=C(OC)C=C(CCC(C)=O)C=C1
|-
| colspan="1" |Molecular Mass
| colspan="2" |194 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Yellow to yellow-brown crystals
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| colspan="1" |CAS Registry Number
| colspan="2" |122-48-5
|-
| Melting Point
| colspan="2" |40-42°C
|-
|colspan="1" |Boiling point
| colspan="2" |290°C
|-
|colspan="1" |Refractive index
| colspan="2" |1.544-1/545 at 20°C

|}

==Zingerone== is the molecule responsible for most of the taste of cooked ginger. It is also a week antioxidant, and this may account for some of the proposed medicinal properties of the compound.

Many other molecules which give foods taste and smell are chemically similar to zingerone, most notably capsaicin and vanillin, which give vanilla and hot peppers their tastes. Zingerone has a higher molecular weight than vanillin, and contains a carbonyl side group which allows stronger Van Der Waals interactions. This means zingerone can bind strongly to itself when compared with molecules like vanillin. This in turn makes zingerone less volatile, which accounts for the fact that while vanilla and ginger give similarly strong tastes, vanilla's smell is much more potent. It can escape more readily as a gas. On the other hand, capsaicin is a heavier molecule than zingerone, is much less volatile, and therefore is completely odourless.
To compare zingerone with several other 'taste' molecules see [http://antoine.frostburg.edu/chem/senese/101/features/capsaicin.shtml General Chemistry Online: Fire and Spice]

Fresh ginger contains no zingerone. When ginger is cooked gingerol, a molecule present in fresh ginger, reacts to give zingerone. Whereas gingerol has an extremely strong taste, zingerone has a milder, sweeter taste. This is not only true for ginger, but also in a smaller way for raspberries, another potential source of zingerone.

It is thought that gingerol and zingerone are evolutionarily favourable chemicals for plants to contain because they are used as a defence mechanism. Although the taste of zingerone is pleasant, up to about 80ppm, the taste of large amounts of gingerol in fresh ginger is repellent, at least to most mammalian species. Interestingly, many species of birds are insensitive to both gingerol and zingerone in concentrations up to 10,000ppm. [elibrary.unm.edu/sora/Auk/v112n02/p0511-p0514.pdf Mammmalian Irritants as Chemical Stimuli for Birds: The importance of training]

[[Image:gingerol.gif|50px]]
Chemical structure of gingerol, a precursor of gingerone

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 5.987 -0.884 -0.823 0.00 0.00 O+0
ATOM 2 C 0 4.709 -0.762 -0.373 0.00 0.00 C+0
ATOM 3 C 0 4.152 0.500 -0.190 0.00 0.00 C+0
ATOM 4 O 0 4.884 1.614 -0.459 0.00 0.00 O+0
ATOM 5 C 0 4.047 2.737 -0.176 0.00 0.00 C+0
ATOM 6 C 0 2.850 0.619 0.269 0.00 0.00 C+0
ATOM 7 C 0 2.107 -0.514 0.542 0.00 0.00 C+0
ATOM 8 C 0 0.691 -0.382 1.040 0.00 0.00 C+0
ATOM 9 C 0 -0.268 -0.352 -0.152 0.00 0.00 C+0
ATOM 10 C 0 -1.685 -0.220 0.347 0.00 0.00 C+0
ATOM 11 C 0 -2.827 -0.167 -0.635 0.00 0.00 C+0
ATOM 12 C 0 -4.147 -0.033 0.126 0.00 0.00 C+0
ATOM 13 O 0 -4.178 1.221 0.810 0.00 0.00 O+0
ATOM 14 C 0 -5.314 -0.104 -0.861 0.00 0.00 C+0
ATOM 15 C 0 -6.636 -0.096 -0.090 0.00 0.00 C+0
ATOM 16 C 0 -7.803 -0.167 -1.077 0.00 0.00 C+0
ATOM 17 O 0 -1.904 -0.158 1.532 0.00 0.00 O+0
ATOM 18 C 0 2.660 -1.768 0.359 0.00 0.00 C+0
ATOM 19 C 0 3.957 -1.893 -0.103 0.00 0.00 C+0
ATOM 20 H 0 6.557 -0.900 -0.042 0.00 0.00 H+0
ATOM 21 H 0 3.751 2.714 0.873 0.00 0.00 H+0
ATOM 22 H 0 4.594 3.658 -0.378 0.00 0.00 H+0
ATOM 23 H 0 3.158 2.696 -0.805 0.00 0.00 H+0
ATOM 24 H 0 2.415 1.598 0.412 0.00 0.00 H+0
ATOM 25 H 0 0.450 -1.232 1.679 0.00 0.00 H+0
ATOM 26 H 0 0.591 0.541 1.611 0.00 0.00 H+0
ATOM 27 H 0 -0.027 0.498 -0.790 0.00 0.00 H+0
ATOM 28 H 0 -0.168 -1.275 -0.722 0.00 0.00 H+0
ATOM 29 H 0 -2.699 0.691 -1.295 0.00 0.00 H+0
ATOM 30 H 0 -2.840 -1.082 -1.227 0.00 0.00 H+0
ATOM 31 H 0 -4.234 -0.844 0.849 0.00 0.00 H+0
ATOM 32 H 0 -4.099 1.910 0.135 0.00 0.00 H+0
ATOM 33 H 0 -5.278 0.756 -1.529 0.00 0.00 H+0
ATOM 34 H 0 -5.240 -1.021 -1.446 0.00 0.00 H+0
ATOM 35 H 0 -6.672 -0.956 0.578 0.00 0.00 H+0
ATOM 36 H 0 -6.710 0.821 0.494 0.00 0.00 H+0
ATOM 37 H 0 -8.744 -0.161 -0.528 0.00 0.00 H+0
ATOM 38 H 0 -7.766 0.694 -1.746 0.00 0.00 H+0
ATOM 39 H 0 -7.729 -1.084 -1.662 0.00 0.00 H+0
ATOM 40 H 0 2.076 -2.651 0.573 0.00 0.00 H+0
ATOM 41 H 0 4.387 -2.874 -0.245 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 46
CONECT 2 1 19 3 0 NONE 47
CONECT 3 2 4 6 0 NONE 48
CONECT 4 3 5 0 0 NONE 49
CONECT 5 4 21 22 23 NONE 50
CONECT 6 3 7 24 0 NONE 51
CONECT 7 6 8 18 0 NONE 52
CONECT 8 7 9 25 26 NONE 53
CONECT 9 8 10 27 28 NONE 54
CONECT 10 9 11 17 0 NONE 55
CONECT 11 10 12 29 30 NONE 56
CONECT 12 11 13 14 31 NONE 57
CONECT 13 12 32 0 0 NONE 58
CONECT 14 12 15 33 34 NONE 59
CONECT 15 14 16 35 36 NONE 60
CONECT 16 15 37 38 39 NONE 61
CONECT 17 10 0 0 0 NONE 62
CONECT 18 7 19 40 0 NONE 63
CONECT 19 18 2 41 0 NONE 64
END NONE 65
</inlineContents>
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</jmol>

Above: 3D strutcture of [4]-Gingerol

There is some evidence that gingerol has therapeutic properties that help with symptoms like nausea and vomiting, and may be of some use as a natural remedy to things like morning sickness and seasickness. There is some controversy as to these effects because not all studies show any effect when compared with a placebo.
[http://bja.oxfordjournals.org/cgi/content/abstract/84/3/367 Article:efficacy of ginger for nausea and vomiting]

==Zingerone synthesis==

[[Image:Zingerone synthesis.gif|thumb|Description]]

In 1968 CONNELL and SUTHERLAND examined the structures and synthesis of zingerone. They found that it was possible to synthesise zingerone by hydrolysing gingerol using hot aqueous barium hydroxide solution. Other aldehydes are also produced in this reaction.

[[Image:Gingerol hydrolysis.gif|thumb|Description]]

{|-
! {{chembox header}} colspan="3" | Properties of Gingerol
|-
| colspan="1" |CAS Registry Number
| colspan="2"|41743-68-4, 77398-90-4
|-
| colspan="1" |Chemical Name
| colspan="2" |[4]-Gingerol
|-
| colspan="1" |Autoname
| colspan="2" |5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-octan-3-one
|-
| colspan="1" |Molecular Formula
| colspan="2" |C15H22O4
|-
| colspan="1" |Molecular Weight
| colspan="2" |266.34
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| Melting Point
| colspan="2" |74-75°C

|}

==Spectra of Zingerone==

''Infrared Spectrum'':
[[Image:irzingerone.PNG]]

''Infra Red Assignements for Zingerone:''

C = O - 1700 cm<sup>-1</sup>

O - H - 3410 cm<sup>-1</sup>

''Mass Spectrum'':
[[Image:Zingerone.jpg|thumb|Description]]

==Uses of Zingerone by Chemical Scientists==
In 2005 an article in the American Chemical Society found that Zingerone inhibited the formation of peroxynitrite (ONOO<sup>-</sup> ), which is formed when a O2<sup>-</sup> radical reacts with an NO radical. This can cause strokes, atherosclerosis and even Alzheimer's disease. It was found that Zingerone aided with electron donation and so helping with the cells defense against many diseases.

==References==
* Spectra obtained from NIST Chemistry Web book - [http://webbook.nist.gov/chemistry/]
* Connell, D. W.; Sutherland, M. D. A Re-Examination of Gingerol, Shogaol, and Zingerone, The Pungent Principles of Ginger (Zingiber Officinule Roscoe). Aust. J. Chem. 1969,22, 1033-1043, and references cited therein.
* Properties of Gingerol was obtained from Beilstein (Beilstein registry number 1991143).
*Sang-Guk Shin, Ji Young Kim, et. al.; "Zingerone as an Antioxidant against Peroxynitrite"; American Chemical Society; August 2005
*General Chemistry Online: Fire and Spice
*Article:efficacy of ginger for nausea and vomiting, British Journal of Anaesthesia
*http://www.thegoodscentscompany.com, provided some additional data
*elibrary.unm.edu/sora/Auk/v112n02/p0511-p0514.pdf Mammalian Irritants as Chemical Stimuli for Birds:
The Importance of Training J. RUSSELML ASONA ND LARRYC LARK provided details of bird insensitiviy

[[Further Abstract & Syntheses]]

2006-10-19T12:55:14Z

Bg105:

==Zingerone==

[[Image:Untitled.gif]]
Chemical Structure of zingerone

{| border="1"
|+ '''General Data'''
|-
|Chemical Name||4-(4-hydroxy-3-methoxyphenyl)-2-butanone
|-
|Chemical Formula||C<sub>11</sub>H<sub>14</sub>O<sub>3</sub>
|-
|SMILES String||OC1=C(OC)C=C(CCC(C)=O)C=C1
|}

Zingerone is the molecule responsible for most of the taste of cooked ginger. It is also a week antioxidant, and this may account for some of the proposed medicinal roperties of the compound.

Many other molecules which give foods taste and smell are chemically similar to zingerone, most notably capsaicin and vanillin, which give vanilla and hot peppers their tastes. Zingerone has a higher molecular weight than vanillin, and contains a carbonyl side group which allows stronger Van Der Waals interactions. This means zingerone can bind strongly to itself when compared with molecules like vanillin. This in turn makes zingerone less volatile, which accounts for the fact that while vanilla and ginger give similarly strong tastes, vanilla's smell is much more potent. It can escape more readily as a gas. On the other hand, capsaicin is a heavier molecule than zingerone, is much less volatile, and therefore is completely odourless.
To compare zingerone with several other 'taste' molecules see [http://antoine.frostburg.edu/chem/senese/101/features/capsaicin.shtml General Chemistry Online: Fire and Spice]

Fresh ginger contains no zingerone. When ginger is cooked gingerol, a molecule present in fresh ginger, reacts to give zingerone. Whereas gingerol has an extremely strong taste, zingerone has a milder, sweeter taste.

[[Image:gingerol.gif]]
Chemical structure of gingerol, a precursor of gingerone

There is some evidence that gingerol has therapeutic properties that help with symptoms like nausea and vomiting, and may be of some use as a natural remedy to things like morning sickness and seasickness. There is some controversy as to these effects because not all studies show any effect when compared with a placebo.
[http://bja.oxfordjournals.org/cgi/content/abstract/84/3/367 Article:efficacy of ginger for nausea and vomiting]

It:Gingerone

2006-10-19T12:53:34Z

Bg105: Added two structures, table, title, link to journal and text over course of day

==Zingerone==

[[Image:Untitled.gif]]
Chemical Structure of zingerone

{| border="1"
|+ '''General Data'''
|-
|Chemical Name||4-(4-hydroxy-3-methoxyphenyl)-2-butanone
|-
|Chemical Formula||C<sub>11</sub>H<sub>14</sub>O<sub>3</sub>
|-
|SMILES String||OC1=C(OC)C=C(CCC(C)=O)C=C1
|}

Zingerone is the molecule responsible for most of the taste of cooked ginger. It is also a week antioxidant, and this may account for some of the proposed medicinal roperties of the compound. When ginger is cooked gingerol, a molecule present in fresh ginger, reacts to give zingerone. Whereas gingerone has an extremely strong taste, zingerone has a milder, sweeter taste.

Many other molecules which give foods taste and smell are chemically similar to zingerone, most notably capsaicin and vanillin, which give vanilla and hot peppers their tastes. Zingerone has a higher molecular weight than vanillin, and contains a carbonyl side group which allows stronger Van Der Waals interactions. This means zingerone can bind strongly to itself when compared with molecules like vanillin. This in turn makes zingerone less volatile, which accounts for the fact that while vanilla and ginger give similarly strong tastes, vanilla's smell is much more potent. It can escape more readily as a gas. On the other hand, capsaicin is a heavier molecule than zingerone, is much less volatile, and therefore is completely odourless.
To compare zingerone with several other 'taste' molecules see [http://antoine.frostburg.edu/chem/senese/101/features/capsaicin.shtml General Chemistry Online: Fire and Spice]

[[Image:gingerol.gif]]
Chemical structure of gingerol, a precursor of gingerone

There is some evidence that gingerol has therapeutic properties that help with symptoms like nausea and vomiting, and may be of some use as a natural remedy to things like morning sickness and seasickness. There is some controversy as to these effects because not all studies show any effect when compared with a placebo.
[http://bja.oxfordjournals.org/cgi/content/abstract/84/3/367 Article:efficacy of ginger for nausea and vomiting]