|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||164.160 g·mol−1|
|Melting point||210 to 213 °C (410 to 415 °F; 483 to 486 K)|
|GHS Signal word||Danger|
|H301, H302, H311, H314, H315, H317, H319, H335|
|P260, P261, P264, P270, P271, P272, P280, P301+310, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P330, P332+313, P333+313, P337+313, P361, P362, P363|
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 and fungi 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.
Biosynthetic building block
p-Coumaric acid is the precursor of 4-ethylphenol produced by the yeast Brettanomyces in wine. The enzyme cinnamate decarboxylase catalyzes the conversion oof p-coumaric acid into 4-vinylphenol. Vinyl phenol reductase then catalyzes the reduction of 4-vinylphenol to 4-ethylphenol. 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 uridine diphosphate glucose and cis-p-coumarate to produce 4′-O-β-D-glucosyl-cis-p-coumarate and uridine diphosphate (UDP). This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases.
- Coumaroyl-Coenzyme A
- Ferulic acid
- Cinnamic acid
- Phenolic content in wine
- p-Coumaroylated anthocyanins
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