O-Coumaric acid

o-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids — o-coumaric acid, m-coumaric acid, and p-coumaric acid — that differ by the position of the hydroxy substitution of the phenyl group.

o-Coumaric acid

Skeletal formula of o-coumaric acid
Names
Preferred IUPAC name (2E)-3-(2-Hydroxyphenyl)prop-2-enoic acid
Other names ortho-Coumaric acid 2-Hydroxycinnamic acid
Identifiers
CAS Number	614-60-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18125
ChemSpider	553146
ECHA InfoCard	100.009.444
PubChem CID	637540
UNII	23AU5FZB9C Y
CompTox Dashboard (EPA)	DTXSID10883240
InChI InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+ Key: PMOWTIHVNWZYFI-AATRIKPKSA-N InChI=1/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+ Key: PMOWTIHVNWZYFI-AATRIKPKBG
SMILES C1=CC=C(C(=C1)C=CC(=O)O)O
Properties
Chemical formula	C9H8O3
Molar mass	164.16 g/mol
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Natural occurrence

o-Coumaric acid can be found in vinegar.

2-Coumarate reductase is an enzyme that produces 2-coumarate from 3-(2-hydroxyphenyl)propanoate and NAD⁺. This enzyme participates in phenylalanine metabolism.^[2]