m-Coumaric acid

m-Coumaric acid
Names

IUPAC name 3-(3-hydroxyphenyl)propanoic acid
Other names meta-coumaric acid 3-hydroxycinnamic acid
Identifiers
CAS Number	621-54-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:CHEBI:32357
ChemSpider	553147
ECHA InfoCard	100.008.742
EC Number	209-615-0
KEGG	C12621
PubChem	637541
InChI InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ Key: KKSDGJDHHZEWEP-SNAWJCMRSA-N InChI=1/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ Key: KKSDGJDHHZEWEP-SNAWJCMRBO
SMILES C1=CC(=CC(=C1)O)/C=C/C(=O)O
Properties
Chemical formula	C₉H₈O₃
Molar mass	164.16 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

m-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. m-Coumaric acid can be found in vinegar.

External links

m-Coumaric acid at www.phenol-explorer.eu

References

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid

Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid

Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid

Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid

others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid

esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Ferulic acid glucoside
p-Coumaric acid glucoside
1-Sinapoyl-D-glucose

Tartaric acid esters

Caftaric acid
Cichoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C and F
Chiritoside A, B and C
Cistanoside A, B, C, D, E, F, G an 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	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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