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This product has not been tested for solubility or suitability in cell culture. The solubility is tested in Chloroform at 50 mg/ml. However, various sources report that this compound is also slightly soluble in DMSO and Ethanol. This information has not been validated. The end-user would have to determine suitability for cell culture applications.
N3633
β-Naphthoflavone
≥98%
Synonym(s):
beta-Naphthoflavone, 5,6-Benzoflavone, BNF
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1 G
$56.00
5 G
$156.00
About This Item
Empirical Formula (Hill Notation):
C19H12O2
CAS Number:
Molecular Weight:
272.30
Beilstein/REAXYS Number:
18991
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.[1]
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[2]
- as AhR agonists, to treat primary normal human epidermal keratinocytes (NHEKs) to study about aryl hydrocarbon receptor (AhR) activation by western blot analysis[3]
- to determine its effect on the expression of dystrophin (Dp)71[1]
- to stimulate the expression of causes recombination (Cre) recombinase and to delete the flanking alleles of locus of crossing (x) over, P1 (loxP) sequences[4]
Biochem/physiol Actions
β-Naphthoflavone (BNF) is an exogenous ligand for aryl hydrocarbon receptor (AhR) in humans.[2] 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).[5] BNF represses the expression of Duchenne muscular dystrophy gene, dystrophin (Dp)71 by altering the binding of the transcription factors.[1]
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
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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)
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
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
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)
Articles
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.
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How can I reconstitute the reagent β-Naphthoflavone (Ref# N3633-1G) for cell culture? Is it soluble in ethanol or DMSO?
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