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Coumaric acid

 
Wikipedia: Coumaric acid
p-Coumaric acid
Coumaric acid acsv.svg
IUPAC name
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
InChI
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

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. 

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