4-oxo Retinoic Acid

4-oxo Retinoic acid is an active metabolite of the vitamin A metabolite and retinoic acid receptor (RAR) ligand all-trans retinoic acid (Cay-11017). It is formed from all-trans retinoic acid by several cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A7, and CYP26A1. 4-oxo Retinoic acid binds to RARalpha, RARbeta, and RARgamma (IC50s = 59, 50, and 142 nM, respectively, in radioligand binding assays) and induces expression of a luciferase reporter in COS-7 cells expressing RARalpha, RARbeta, or RARgamma (EC50s = 33, 8, and 89 nM, respectively). It increases protein levels of cytokeratin 7 (CK-7) and CK-19 in human epidermal keratinocytes when used at a concentration of 1 µM. 4-oxo Retinoic acid (10-1,000 nM) inhibits the proliferation of MCF-7 breast cancer cells. It is teratogenic to zebrafish embryos (EC50 = 8.1 nM).CAS Number: 38030-57-8. Synonyms: all-trans-4-keto Retinoic Acid, all-trans-4-oxo RA, all-trans-4-oxo Retinoic Acid, 4-keto atRA, 4-oxo RA. Molecular Formula: C20H26O3. Formula Weight: 314.4. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Chloroform: Slightly soluble, Methanol: Slightly soluble. lambdamax: 280, 360 nm. SMILES: OC(/C=C(C)/C=C/C=C(C)/C=C/C(C(C)(CC1)C)=C(C)C1=O)=O. InChi Code: InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+. InChi Key: GGCUJPCCTQNTJF-FRCNGJHJSA-N. Origin: Synthetic.