alpha-Naphthoflavone

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. alpha-Naphthoflavone is a flavone that modulates xenobiotic metabolism at several points. It antagonizes AhR, blocking the expression of phase I and II genes at nanomolar concentrations, although it can agonize AhR at higher concentrations (10 µM). alpha-Naphthoflavone inhibits CYP19 (aromatase), CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 µM). Dietary alpha-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.Formal Name: 2-phenyl-4H-naphtho[1,2-b]pyran-4-one. CAS Number: 604-59-1. Synonyms: 7,8-Benzoflavone, NSC 407011. Molecular Formula: C19H12O2. Formula Weight: 272.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMF:PBS (pH 7.2) (1:4): 0.1 mg/ml, DMSO: 10 mg/ml, Ethanol: 1 mg/ml. lambdamax: 225, 280, 344 nm. SMILES: O=C1C2=C(C(C=CC=C3)=C3C=C2)OC(C4=CC=CC=C4)=C1. InChi Code: InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H. InChi Key: VFMMPHCGEFXGIP-UHFFFAOYSA-N.