P-Coumaric acid
Chemical compound
From Wikipedia, the free encyclopedia
p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of coumaric acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.
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| Names | |
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| Preferred IUPAC name
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid | |
| Other names
(E)-3-(4-Hydroxyphenyl)-2-propenoic acid (E)-3-(4-Hydroxyphenyl)acrylic acid para-Coumaric acid 4-Hydroxycinnamic acid trans-4-Hydroxycinnamic acid β-(4-Hydroxyphenyl)acrylic acid | |
| Identifiers | |
3D model (JSmol) |
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| 2207383 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.116.210 |
| EC Number |
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| 2245630 | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H8O3 | |
| Molar mass | 164.160 g·mol−1 |
| Melting point | 210 to 213 °C (410 to 415 °F; 483 to 486 K) |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H315, H319, H335[1] | |
| P261, P264, P271, P280, P302+P352, P305+P351+P338 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Natural occurrences
It is a precursor to many natural products, especially lignols, precursors to the woody mass that comprise many plants.[2] Of the myriad occurrences, p-coumaric acid can be found in Gnetum cleistostachyum.[3]
In food
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.[citation needed] It is found in wine and vinegar.[4] It is also found in barley grain.[5]
Derivatives
p-Coumaric acid glucoside can also be found in commercial breads containing flaxseed.[7] Diesters of p-coumaric acid can be found in carnauba wax.
Biosynthesis
It is biosynthesized from cinnamic acid by the action of the P450-dependent enzyme 4-cinnamic acid hydroxylase (C4H).
It is also produced from L-tyrosine by the action of tyrosine ammonia lyase (TAL).
+ NH3 + H+
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 of p-coumaric acid into 4-vinylphenol.[8] 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.
The conversion of p-coumaric acid to 4-ethyphenol by Brettanomyces
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.[9]
Phloretic acid, found in the rumen of sheep fed with dried grass, is produced by hydrogenation of the 2-propenoic side chain of p-coumaric acid.[10]
The enzyme, resveratrol synthase, also known as stilbene synthase, catalyzes the synthesis of resveratrol ultimately from a tetraketide derived from 4-coumaroyl CoA.[11]
p-Coumaric acid is a cofactor of photoactive yellow proteins (PYP), a homologous group of proteins found in many eubacteria.[12]
p-Coumaric acid is found as the base moiety of caleicine, one of many sesquiterpenes in Calea ternifolia.