4-hydroxycinnamic acid

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
CAS Number	501-98-4^Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:32374^Y
ChEMBL	ChEMBL66879^Y
ChemSpider	553148^Y
DrugBank	DB04066^Y
ECHA InfoCard	100.116.210
EC Number	231-000-0
IUPHAR/BPS	5787
PubChem	637542
InChI InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+^Y Key: NGSWKAQJJWESNS-ZZXKWVIFSA-N^Y InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11, 12)/b6-3+/f/h11H InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ Key: NGSWKAQJJWESNS-ZZXKWVIFBJ
SMILES C1=CC(=CC=C1\C=C\C(=O)O)O c1cc(ccc1/C=C/C(=O)O)O
Properties
Chemical formula	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 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.

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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