Coumaric acid
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| p-Coumaric acid | |
|---|---|
| Image:Coumaric acid.png | |
| IUPAC name | 3-(4-hydroxyphenyl)- 2-propenoic acid |
| Other names | para-coumaric acid 4-hydroxycinnamic acid β-(4-hydroxyphenyl)acrylic acid |
| Identifiers | |
| CAS number | |
| SMILES | OC(/C=C/C1=CC=C(O)C=C1)=O |
| Properties | |
| Molecular formula | C9H8O3 |
| Molar mass | 164.15 g/mol |
| Melting point |
210-213 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Coumaric acids are organic compounds that are hydroxy derivatives 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 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.
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.
p-Coumaric acid has antioxidant properties and is believed to reduce the risk of stomach cancer[1] by reducing the formation of carcinogenic nitrosamines.[2]
See also
References
- ↑ Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells. Ferguson Lynnette R; Zhu Shuo-tun; Harris Philip J. Molecular Nutrition & Food Research (2005), 49(6), 585-93.
- ↑ "Reaction of p-hydroxycinnamic acid derivatives with nitrite and its relevance to nitrosamine formation. Kikugawa, Kiyomi; Hakamada, Tomoko; Hasunuma, Makiko; Kurechi, Tsutao Journal of Agricultural and Food Chemistry (1983), 31(4), 780-5.
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