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P-Coumaric acid

p-Coumaric acid
Skeletal formula of p-coumaric acid
Ball-and-stick model of p-coumaric acid
Names
IUPAC name
(E)-3-(4-hydroxyphenyl)-2-propenoic acid
Other names
para-coumaric acid,

4-hydroxycinnamic acid,

β-(4-hydroxyphenyl)acrylic acid
Identifiers
501-98-4 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:32374 YesY
ChEMBL ChEMBL66879 YesY
ChemSpider 553148 YesY
DrugBank DB04066 YesY
ECHA InfoCard 100.116.210
EC Number 231-000-0
5787
PubChem 637542
Properties
C9H8O3
Molar mass 164.16 g·mol−1
Melting point 210 to 213 °C (410 to 415 °F; 483 to 486 K)
Hazards
R-phrases R36/37/38
S-phrases S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-hydroxycinnamic acid,

p-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acido-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.

It is a crystalline solid that is slightly soluble in water, but well soluble in ethanol and diethyl ether.

Together with sinapyl alcohol and coniferyl alcohols, p-coumaric acid is a major component of lignin.

p-Coumaric acid can be found in Gnetum cleistostachyum.

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.

p-Coumaric acid from pollen is a constituent of honey.

p-Coumaric acid glucoside can also be found in commercial breads containing flaxseed.

Diesters of p-coumaric acid can be found in carnauba wax.


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