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Merck

N3633

β-Naphthoflavone

≥98%

Synonym(s):

beta-Naphthoflavone, 5,6-Benzoflavone, BNF

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About This Item

Empirical Formula (Hill Notation):
C19H12O2
CAS Number:
6051-87-2
Molecular Weight:
272.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57654450
EC Number:
227-958-4
Beilstein/REAXYS Number:
18991
MDL number:
MFCD00004986

Key Documents

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Product Name

β-Naphthoflavone, ≥98%

InChI key

OUGIDAPQYNCXRA-UHFFFAOYSA-N

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

SMILES string

O=C1C=C(Oc2ccc3ccccc3c12)c4ccccc4

assay

≥98%

color

off-white to yellow

mp

164-166 °C (lit.)

storage temp.

2-8°C

Quality Level

200

Gene Information

rat ... Gabra2(29706)

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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.

General description

β-Naphthoflavone is a polyaromatic hydrocarbon.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCK9091
SLCF5489
SLCC7687
SLBW8991
SLBR8979V

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Transcriptome regulation and chromatin occupancy by E2F3 and MYC in mice
Tang X, et al.
Scientific data, 3(4), 160008-160008 (2016)
Cyp1a reporter zebrafish reveals target tissues for dioxin
Kim KH, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 134, 57-65 (2013)
beta-naphthoflavone interferes with cyp1c1, cox2 and IL-8 gene transcription and leukotriene B4 secretion in Atlantic cod (Gadus morhua) head kidney cells during inflammation
Holen E and Olsvik P
Fish & Shellfish Immunology, 54(1), 128-134 (2016)
Ryeo-Ok Kim et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 157(2), 172-182 (2012-11-28)
CYP1A is involved in the metabolism of diverse chemicals, including polycyclic aromatic hydrocarbons and alkylated-PAHs, as a first line of detoxification mechanism. First, we identified and characterized the CYP1A gene from the marine medaka, Oryzias melastigma. O. melastigma CYP1A (Om-CYP1A)
Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry.
Minoru Ishikawa et al.
Journal of medicinal chemistry, 54(6), 1539-1554 (2011-02-25)
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