o-Coumaric acid

o-Coumaric acid
Skeletal formula of 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
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:[1]
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 [77 °F], 100 kPa).
Infobox references

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 converts o-coumaric acid to melilotic acid using reduced nicotinamide adenine dinucleotide (NADH).[2] This enzyme participates in phenylalanine metabolism.[3]

2D representation of the chemical structure of o-Coumaric acid.
o-coumaric acid
+ NADH
 
 
H+
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H+
 
 
2D representation of the chemical structure of Q11751633.
melilotic acid
+ NAD+
 

References

  1. ^ GHS: PubChem
  2. ^ Enzyme 1.3.1.11 at KEGG Pathway Database.
  3. ^ 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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