O-Coumaric acid

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.444 Edit this at Wikidata
UNII
  • 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
  • C1=CC=C(C(=C1)C=CC(=O)O)O
Properties
C9H8O3
Molar mass 164.16 g/mol
Hazards
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H315, H319, H335
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).

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.

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]

References

  1. ^ GHS: PubChem
  2. ^ Levy, Carl C.; Weinstein, Gerald D. (1964). "The Metabolism of Coumarin by a Microorganism. II. The Reduction of o-Coumaric Acid to Melilotic Acid". Biochemistry. 3 (12): 1944–7. doi:10.1021/bi00900a027. PMID 14269315.


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