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o-Coumaric acid

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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: Toxic GHS07: 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).
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 acidso-coumaric acid, m-coumaric acid, and p-coumaric acid — that differ by the position of the hydroxy substitution of the phenyl group.

Natural occurrence

[edit ]

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

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  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.
[edit ]


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
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Conjugates with
coenzyme A (CoA)
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