FComEx: 3,4,5-Trimethoxycinnamic acid (PC000726)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:15 UTC

Update date

2017-01-19 02:36:34 UTC

FoodComEx ID

PC000726

FoodDB Record

FDB023019

Chemical Information

Name

3,4,5-Trimethoxycinnamic acid

Description

3,4,5-Trimethoxycinnamic acid is an organic acid found in normal human urine. (PMID: 6992730, 6511847) Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID: 16313198) [HMDB]

CAS Number

90-50-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
3,4,5-Trimethoxy cinnamate	hmdb
3,4,5-Trimethoxy cinnamic acid	hmdb
3,4,5-Trimethoxycinnamate	hmdb
3,4,5-Trimethoxyphenylacrylate	hmdb
3,4,5-Trimethoxyphenylacrylic acid	hmdb
O-Methylsinapate	hmdb
O-Methylsinapic acid	hmdb

Chemical Formula

C12H14O5

IUPAC name

(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid

InChI Identifier

InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+

InChI Key

YTFVRYKNXDADBI-SNAWJCMRSA-N

Isomeric SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC

Average Molecular Weight

238.2366

Monoisotopic Molecular Weight

238.084123558

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents