m -Coumaric acid
Skeletal formula of m -coumaric acid
Names
Preferred IUPAC name
(2E )-3-(3-Hydroxyphenyl)prop-2-enoic acid
Other names
meta -Coumaric acid 3-Hydroxycinnamic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard
100.008.742
EC Number
KEGG
UNII
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
C1=CC(=CC(=C1)O)/C=C/C(=O)O
Properties
Chemical formula
C9 H8 O3
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 .[ 1] There are three isomers of coumaric acid – 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.
References
Types of hydroxycinnamic acids
Aglycones
Precursor Monohydroxycinnamic acids (Coumaric acids) 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 formsothers
Esters
glycoside-likes
Esters of caffeic acid with cyclitols
esters ofquinic 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 ofshikimic acid
Dactylifric acid (3-O -caffeoylshikimic acid)
Glycosides
Ferulic acid glucoside
p -Coumaric acid glucoside
1-Sinapoyl-D -glucose
Tartaric acid esters
Caftaric acid
Chicoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)
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
Triferulic acids : 5-5′,8′-O -4″-Triferulic acid
Tetramers
Conjugates withcoenzyme A (CoA)