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N3633 Sigma-Aldrich

β-Naphthoflavone

≥98%

Synonym: 5,6-Benzoflavone, BNF, beta-Naphthoflavone

  • CAS Number 6051-87-2

  • Empirical Formula (Hill Notation) C19H12O2

  • Molecular Weight 272.30

  •  Beilstein/REAXYS Number 18991

  •  EC Number 227-958-4

  •  MDL number MFCD00004986

  •  PubChem Substance ID 57654450

  •  NACRES NA.22

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Properties

Related Categories Benzopyrans, Building Blocks, Cancer Research, Cell Biology, Chemical Synthesis,
Quality Level   200
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

Packaging

1, 5 g in poly bottle

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 & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
QL6200000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.1 During the oxi...
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Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Peer-Reviewed Papers
15

References

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