O-Coumaric acid

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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
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 Â°C [77 Â°F], 100 kPa).
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Natural occurrence

o-Coumaric acid can be found in vinegar.

Biosynthesis

In some plants such as Melilotus species, o-coumaric acid is produced directly from cinnamic acid by the enzyme trans-cinnamate 2-monooxygenase.[2]

2D representation of the chemical structure of cinnamic acid .
cinnamic acid
+ NADPH
 
 
O2 + H+
H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of O-Coumaric acid.
o-coumaric acid
+ NADP+
 

Metabolism

2-Coumarate reductase is an enzyme that converts o-coumaric acid to melilotic acid using reduced nicotinamide adenine dinucleotide (NADH).[3] This enzyme participates in phenylalanine metabolism.[4]

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

External links

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