From Wikipedia, the free encyclopedia
o -Coumaric acid
Names
Preferred IUPAC name
(2E )-3-(2-Hydroxyphenyl)prop-2-enoic acid
Other names
ortho -Coumaric acid 2-Hydroxycinnamic acid
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.009.444
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
C9 H8 O3
Molar mass
164.16 g/mol
Hazards
GHS labelling :
[1]
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 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
^ GHS:
PubChem
^ 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
Aglycones
Precursor Monohydroxycinnamic acids (Coumaric acids)
Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of caffeic acid with cyclitols
Glycosides
Tartaric acid esters Other esters with caffeic acid Caffeoyl phenylethanoid glycoside (CPG)
Echinacoside
Calceolarioside A ,
B ,
C ,
F
Chiritoside A ,
B ,
C
Cistanoside A ,
B ,
C ,
D ,
E ,
F ,
G ,
H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (
Isoverbascoside ,
2′-Acetylverbascoside )
Oligomeric forms
Dimers
Diferulic acids (DiFA) :
5,5′-Diferulic acid ,
8-O -4′-Diferulic acid ,
8,5′-Diferulic acid ,
8,5′-DiFA (DC) ,
8,5′-DiFA (BF) ,
8,8′-Diferulic acid
Trimers Tetramers
Conjugates with
coenzyme A (CoA)