N3633

β-Naphthoflavone

≥98%

• Synonym(s): beta-Naphthoflavone, 5,6-Benzoflavone, BNF
• Empirical Formula (Hill Notation): C₁₉H₁₂O₂
• CAS Number: 6051-87-2
• Molecular Weight: 272.30
• Beilstein/REAXYS Number: 18991
• EC Number: 227-958-4
• MDL number: MFCD00004986
• UNSPSC Code: 12352100
• PubChem Substance ID: 57654450
• NACRES: NA.22

Properties

• assay: ≥98%
• color: off-white to yellow
• mp: 164-166 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: O=C1C=C(Oc2ccc3ccccc3c12)c4ccccc4
• InChI: 1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H
• InChI key: OUGIDAPQYNCXRA-UHFFFAOYSA-N
• Gene Information: rat ... Gabra2(29706)

Description

General description

β-Naphthoflavone is a polyaromatic hydrocarbon.

Application

β-Naphthoflavone has been used:

• as aryl hydrocarbon receptor agonist to elucidate its effect on Cyp1A1 expression in embryos of transgenic cytochrome P450 1A1 (cyp1a) reporter zebrafish
• as AhR agonists, to treat primary normal human epidermal keratinocytes (NHEKs) to study about aryl hydrocarbon receptor (AhR) activation by western blot analysis
• to determine its effect on the expression of dystrophin (Dp)71
• to stimulate the expression of causes recombination (Cre) recombinase and to delete the flanking alleles of locus of crossing (x) over, P1 (loxP) sequences

Biochem/physiol Actions

β-Naphthoflavone (BNF) is an exogenous ligand for aryl hydrocarbon receptor (AhR) in humans. It is an inducer of phase I detoxification enzymes (CYPs) and phase II enzymes (UDP-GTs) and NAD(P)H-dependent quinone oxyreductase-1(NQO1). It also induces cytochrome P450 (Cyp1a). BNF represses the expression of Duchenne muscular dystrophy gene, dystrophin (Dp)71 by altering the binding of the transcription factors.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves