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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
0000515159
0000515161
0000515160
0000515160
0000515161

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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)
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)
Preethi Korangath et al.
Science advances, 6(13), eaay1601-eaay1601 (2020-04-02)
The factors that influence nanoparticle fate in vivo following systemic delivery remain an area of intense interest. Of particular interest is whether labeling with a cancer-specific antibody ligand ("active targeting") is superior to its unlabeled counterpart ("passive targeting"). Using models
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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