rac all-trans 4-Hydroxy Retinoic Acid - CAS 66592-72-1

rac all-trans 4-Hydroxy Retinoic Acid (CAS 66592-72-1) is a metabolite of all- trans retinoic acid formed by the cytochrome P450 (CYP) isoforms CYP26A1, B1, and C1. It binds to retinoic acid receptors (RARs) with a lower affinity than other all-trans retinoic acid metabolites (IC50s = 606, 298, and 892 nM for RARα, RARβ, and RARγ, respectively, in a radioligand binding assay). It also transactivates RARs with a lower efficacy than other metabolites (EC50s = 791, 64, and 94 nM for RARα, RARβ, and RARγ, respectively) but induces transcription of a reporter plasmid equipotently. all-trans-4-hydroxy Retinoic acid inhibits cell growth, halts the cell cycle in the G1 phase, and induces differentiation of NB4 acute promyelocytic leukemia cells (EC50 = 79.8 nM).


Catalog Number: R010634

CAS Number: 66592-72-1

PubChem Substance ID:355199497

Molecular Formula: C20H28O3

Molecular Weight:316.441

Purity: ≥95%

* For research use only. Not for human or veterinary use.

Synonym

Synonyms4-Hydroxy-all-trans-retinoic Acid; 4-Hydroxyretinoic Acid;?

Property

Molecular Formula: C20H28O3
Molecular Weight316.441
Purity≥95%
Storage-20°C

Computed Descriptor

IUPAC Name(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
InChIInChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChIKeyKGUMXGDKXYTTEY-FRCNGJHJSA-N
SMILESCC1=C(C(CCC1O)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C