rac all-trans 4-Hydroxy Retinoic Acid

• CAT Number: R010634
• CAS Number: 66592-72-1
• Molecular Formula: C20H28O3
• Molecular Weight: 316.441
• Purity: ≥95%
• Synonyms: 4-Hydroxy-all-trans-retinoic Acid; 4-Hydroxyretinoic Acid;?
• Storage: -20°C
• IUPAC Name: (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• InChI: InChI=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+
• InChIKey: KGUMXGDKXYTTEY-FRCNGJHJSA-N
• SMILES: CC1=C(C(CCC1O)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C

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).

Reference

1.Idres, Nadia, et al. "Activation of retinoic acid receptor-dependent transcription by all-trans-retinoic acid metabolites and isomers." Journal of Biological Chemistry 277.35 (2002): 31491-31498.
2.Taimi, Mohammed, et al. "A novel human cytochrome P450, CYP26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid." Journal of Biological Chemistry 279.1 (2004): 77-85.
3.Idres, Nadia, et al. "Granulocytic differentiation of human NB4 promyelocytic leukemia cells induced by all-trans retinoic acid metabolites." Cancer research 61.2 (2001): 700-705.