FComEx: Retinoic acid (PC000498)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:58 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000498

FoodDB Record

FDB022710

Chemical Information

Name

Retinoic acid

Description

Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). [HMDB]

CAS Number

302-79-4

Structure

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

Synonyms

Synonym	Source
(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	hmdb
(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	hmdb
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	hmdb
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	hmdb
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)	Generator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)	ChEBI
acide retinoique (French)	hmdb
AGN 100335	ChEBI
all-(E)-Retinoate	hmdb
all-(E)-Retinoic acid	hmdb
all-trans-Retinoate	hmdb
all-trans-Retinoic acid	hmdb
all-trans-Tretinoin	hmdb
all-trans-Vitamin a acid	ChEBI
all-trans-Vitamin A1 acid	hmdb
all-trans-β-retinoate	Generator
all-trans-β-retinoic acid	Generator
beta-Retinoate	Generator
beta-Retinoic acid	ChEBI
Retinoate	Generator
Retisol-a	ChEBI
Ro 1-5488	ChEBI
Solage	ChEBI
Stieva-a	ChEBI
trans-Retinoate	Generator
trans-Retinoic acid	ChEBI
Tretin M	hmdb
Tretinoine (French)	hmdb
Vitamin A acid	hmdb
Vitinoin	ChEBI
β-retinoate	Generator
β-retinoic acid	Generator

Chemical Formula

C20H28O2

IUPAC name

3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

InChI Identifier

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)

InChI Key

SHGAZHPCJJPHSC-UHFFFAOYSA-N

Isomeric SMILES

CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O

Average Molecular Weight

300.4351

Monoisotopic Molecular Weight

300.20893014

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents