Coumaric acid

p-Coumaric acid
Identifiers
CAS number 7400-08-0 N
PubChem 637542
ChemSpider 553148 Y
EC number 231-000-0
DrugBank DB04066
ChEBI CHEBI:32374 Y
ChEMBL CHEMBL66879 Y
Jmol-3D images Image 1
Image 2
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
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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]

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.[3] 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.


See also

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. PMID 15841493. 
  2. ^ 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. 
  3. ^ Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol at etslabs.com