4-hydroxycinnamic acid,β-(4-hydroxyphenyl)acrylic acid
|Jmol 3D model||Interactive image
|Molar mass||164.16 g·mol−1|
|Melting point||210 to 213 °C (410 to 415 °F; 483 to 486 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
p-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid—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. p-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid.
Diesters of p-coumaric acid can be found in carnauba wax.
- + Ammonia + H+
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. 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.
cis-p-coumarate glucosyltransferase is an enzyme that uses UDP-glucose and cis-p-coumarate to produce 4'-O-beta-D-glucosyl-cis-p-coumarate and UDP. This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases.
p-Coumaric acid has antioxidant properties and is believed to reduce the risk of stomach cancer by reducing the formation of carcinogenic nitrosamines. p-Coumaric acid in honey also demonstrate in vitro anti-inflammatory activity
p-Coumaric acid is normally present in honey, but not in the substitute nutrients based on high-fructose corn syrup that honey bee keepers feed to their colonies. This absence has been suggested as a possible contributor to Colony Collapse Disorder of honey bees because p-coumaric acid has been found to help honey bees detoxify certain pesticides.
- Coumaroyl-Coenzyme A
- Ferulic acid
- Cinnamic acid
- Phenolic content in wine
- p-Coumaroylated anthocyanins
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