For research use only. Not for therapeutic Use.
<span style="color:#000000;"><span style="font-size:12px;"><span style="font-family:arial,helvetica,sans-serif;">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 (IC<span style="box-sizing: border-box; position: relative; line-height: 0; vertical-align: initial; bottom: -0.25em;">50</span>s = 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 (EC<span style="box-sizing: border-box; position: relative; line-height: 0; vertical-align: initial; bottom: -0.25em;">50</span>s = 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 G<span style="box-sizing: border-box; position: relative; line-height: 0; vertical-align: initial; bottom: -0.25em;">1</span> phase, and induces differentiation of NB4 acute promyelocytic leukemia cells (EC<span style="box-sizing: border-box; position: relative; line-height: 0; vertical-align: initial; bottom: -0.25em;">50</span> = 79.8 nM).</span></span></span>
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Catalog Number | R010634 |
CAS Number | 66592-72-1 |
Synonyms | 4-Hydroxy-all-trans-retinoic Acid; 4-Hydroxyretinoic Acid;? |
Molecular Formula | C20H28O3 |
Purity | ≥95% |
Target | Vitamin D Related/Nuclear Receptor |
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 |
Reference | <span style="color:#000000;"><span style="font-size:12px;"><span style="font-family:arial,helvetica,sans-serif;">1.Idres, Nadia, et al. "Activation of retinoic acid receptor-dependent transcription by all-trans-retinoic acid metabolites and isomers." <i style="font-family: Arial, sans-serif; font-size: 13px;">Journal of Biological Chemistry</i> 277.35 (2002): 31491-31498.<br /> |