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Coumaric acid

p-Coumaric acid

IUPAC name	3-(4-hydroxyphenyl)- 2-propenoic acid
Other names	para-coumaric acid 4-hydroxycinnamic acid β-(4-hydroxyphenyl)acrylic acid
Identifiers
CAS number	7400-08-0
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.

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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]

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.

Category: Phenylpropanoids