FComEx: Isoferulic acid (PC000307)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:47 UTC

Update date

2017-01-19 02:36:19 UTC

FoodComEx ID

PC000307

FoodDB Record

FDB002700

Chemical Information

Name

Isoferulic acid

Description

It is used as a food additive; listed in the EAFUS Food Additive Database (Jan 2001) Isoferulic acid is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids, such as caffeic, ferulic, and {rho}-coumaric, with quinic acid. CGA are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2 - 9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation. (PMID: 17884997). Isoferulic acid is found in many foods, some of which are sunflower, peanut, common wheat, and vinegar.

CAS Number

537-73-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid	biospider
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate	biospider
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid	HMDB
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 9CI	db_source
3-Hydroxy-4-methoxy-cinnamate	HMDB
3-Hydroxy-4-methoxy-cinnamic acid	HMDB
3-Hydroxy-4-methoxycinnamate	biospider
3-Hydroxy-4-methoxycinnamic acid	db_source
Hesperetate	biospider
Hesperetic acid	db_source
Hesperetinic acid	db_source
Isoferulate	biospider
Isoferulic acid	db_source

Chemical Formula

C10H10O4

IUPAC name

(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

InChI Identifier

InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

InChI Key

QURCVMIEKCOAJU-HWKANZROSA-N

Isomeric SMILES

COC1=C(O)C=C(\C=C\C(O)=O)C=C1

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents