4-hydroxycinnamic acid,β-(4-hydroxyphenyl)acrylic acid
3D model (JSmol)
|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.
p-Coumaric acid can be found in a wide variety of edible plants such as peanuts, navy beans, tomatoes, carrots, basil and garlic. It is found in wine and vinegar. It is also found in barley grain.
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-β-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 demonstrates 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 honeybee keepers feed to their colonies. This absence has been suggested as a possible contributor to colony collapse disorder of honeybees, because p-coumaric acid has been found to help the bees detoxify certain pesticides. However, recent research has pointed to insecticides as the main reason for bee deaths.
- Coumaroyl-Coenzyme A
- Ferulic acid
- Cinnamic acid
- Phenolic content in wine
- p-Coumaroylated anthocyanins
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