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	501-98-4
PubChem	322
EC number	231-000-0
SMILES	C1=CC(=CC=C1\C=C\C(=O)O)O
InChI	1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11, 12)/b6-3+/f/h11H
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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

• Coumaroyl-Coenzyme A
• Ferulic acid
• Cinnamic acid

References

1. ^ 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. 
2. ^ Kikugawa K, Hakamada T, Hasunuma M, Kurechi T (1983). "Reaction of p-hydroxycinnamic acid derivatives with nitrite and its elevance to nitrosamine formation". Journal of Agricultural and Food Chemistry 1 (4): 780–785. doi:10.1021/jf00118a025. http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1983/31/i04/f-pdf/f_jf00118a025.pdf?sessid=6006l3.