Coumaric acid
| p-Coumaric acid | |
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(E)-3-(4-hydroxyphenyl)-2-propenoic acid |
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Other names
para-coumaric acid, 4-hydroxycinnamic acid, β-(4-hydroxyphenyl)acrylic acid |
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| Identifiers | |
| CAS number | 7400-08-0  |
| PubChem | 637542 |
| ChemSpider | 553148  |
| EC number | 231-000-0 |
| DrugBank | DB04066 |
| ChEBI | CHEBI:32374 |
| ChEMBL | CHEMBL66879 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C9H8O3 |
| Molar mass | 164.16 g mol−1 |
| Exact mass | 164.047344 |
| Melting point |
210–213 °C |
| Hazards | |
| R-phrases | R36/37/38 |
| S-phrases | S24/25 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature.
Together with sinapyl alcohol and coniferyl alcohols, p-coumaric acid is a major component of lignocellulose. It is biosynthesized from cinnamic acid by the action of the P450-dependent enzyme 4-cinnamic acid hydroxylase.
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[edit] Natural occurrence
p-Coumaric acid can be found in a wide variety of edible plants such as peanuts, tomatoes, carrots, and garlic. It is a crystalline solid that is slightly soluble in water, but well soluble in ethanol and diethyl ether.
It is also found in wine and vinegar.[1]
[edit] Biochemistry
p-Coumaric acid is the precursor of 4-ethylphenol produced by the yeast Brettanomyces in wine. The yeast converts this to 4-vinylphenol via the enzyme cinnamate decarboxylase.[2] 4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme vinyl phenol reductase. Coumaric acid is sometimes added to microbiological media, enabling the positive identification of Brettanomyces by smell.
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The conversion of p-coumaric acid to 4-ethyphenol by Brettanomyces
p-Coumaric acid has antioxidant properties and is believed to reduce the risk of stomach cancer[3] by reducing the formation of carcinogenic nitrosamines.[4]
[edit] See also
[edit] References
- ^ Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pages 29-31, doi:10.1007/BF01192948
- ^ Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol at etslabs.com
- ^ Ferguson LR, Shuo-tun Z, Harris PJ (2005). "Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29". Molecular Nutrition & Food Research 49 (6): 585–693. doi:10.1002/mnfr.200500014. PMID 15841493.
- ^ Kikugawa K, Hakamada T, Hasunuma M, Kurechi T (1983). "Reaction of p-hydroxycinnamic acid derivatives with nitrite and its relevance to nitrosamine formation". Journal of Agricultural and Food Chemistry 1 (4): 780–785. doi:10.1021/jf00118a025.
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