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N3633

Sigma-Aldrich

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
Beilstein:
18991
EC Number:
227-958-4
MDL number:
MFCD00004986
UNSPSC Code:
12352100
PubChem Substance ID:
57654450
NACRES:
NA.22

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)

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
The polyaromatic hydrocarbon beta-naphthoflavone alters binding of YY1, Sp1, and Sp3 transcription factors to the Dp71 promoter in hepatic cells
Becerril-Esquivel C, et al.
Molecular Medicine Reports, 17(4), 6150-6155 (2018)
Induction of a chloracne phenotype in an epidermal equivalent model by 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) is dependent on aryl hydrocarbon receptor activation and is not reproduced by aryl hydrocarbon receptor knock down
Forrester AR, et al.
Journal of Dermatological Science, 73(1), 10-22 (2014)
Wei Zhang et al.
Bioorganic & medicinal chemistry, 17(5), 2077-2090 (2009-02-10)
Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of
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