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o-Coumaric acid

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(Redirected from Trans-2-hydroxycinnamate)
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.444 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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:
Pictograms GHS06: ToxicGHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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.

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.

External links


Types of hydroxycinnamic acids
Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
esters of
shikimic acid
Glycosides
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
Oligomeric forms
Dimers
Trimers
Tetramers
Conjugates with
coenzyme A (CoA)
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