M-Coumaric acid

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m-Coumaric acid

IUPAC name 3-(3-hydroxyphenyl)propanoic acid
Other names meta-coumaric acid 3-hydroxycinnamic acid
Identifiers
CAS number	621-54-5
PubChem	91
	Jmol-3D images	Image 1
SMILES C1=CC(=CC(=C1)O)CCC(=O)O
InChI InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) Key: QVWAEZJXDYOKEH-UHFFFAOYSA-N
Properties
Molecular formula	C₉H₈O₃
Molar mass	164.16 g/mol
Except where noted otherwise, 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	3,4,6-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic 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

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

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

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