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B1760

Sigma-Aldrich

Benzo[a]pyrene

≥96% (HPLC)

Synonym(s):

3,4-Benzopyrene, 3,4-Benzpyrene, Benzo[def]chrysene

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About This Item

Empirical Formula (Hill Notation):
C20H12
CAS Number:
50-32-8
Molecular Weight:
252.31
Beilstein:
1911333
EC Number:
200-028-5
MDL number:
MFCD00003602
UNSPSC Code:
12352005
PubChem Substance ID:
24891610
NACRES:
NA.25

Assay

≥96% (HPLC)

form

solid

bp

495 °C (lit.)

mp

177-180 °C (lit.)

SMILES string

c1ccc2c(c1)cc3ccc4cccc5ccc2c3c45

InChI

1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H

InChI key

FMMWHPNWAFZXNH-UHFFFAOYSA-N

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Application

Benzo[a]pyrene (PAH), a polycyclic aromatic hydrocarbon pollutant, is used as a chemical carcinogen in experimental models of cancer. Carcinogenesis depends on it′s oxidation by CYP1A1 to benzo[a]pyrenediolepoxide, that forms depurinating adducts with DNA that dissociate to form abasic lesions. Benzo[a]pyrene is a ligand for the arylhydrocarbon receptor (AhR), and some of its biological effects, including the induction of CYP1A1, appear to be mediated via activation of the AhR.

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Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Muta. 1B - Repr. 1B - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Ariel Revel et al.
Journal of applied toxicology : JAT, 23(4), 255-261 (2003-07-29)
Benzo[a]pyrene (BaP) is an agonistic ligand for the aryl hydrocarbon receptor (AhR) and a major environmental carcinogen implicated in the aetiology of lung cancer through the induction of benzo[a]pyrene diol epoxidation (BPDE) and BPDE-DNA adducts. Because BaP metabolization requires cytochrome
Yi-Chen Lin et al.
Antioxidants (Basel, Switzerland), 9(8) (2020-08-17)
Benzo[a]pyrene (B[a]P) is a polycyclic aromatic hydrocarbon formed by the incomplete combustion of organic matter. Environmental B[a]P contamination poses a serious health risk to many organisms because the pollutant may negatively affect many physiological systems. As such, chronic exposure to
Audrey Barranger et al.
Nanomaterials (Basel, Switzerland), 9(7) (2019-07-11)
This study aimed to assess the ecotoxicological effects of the interaction of fullerene (C60) and benzo[a]pyrene (B[a]P) on the marine mussel, Mytilus galloprovincialis. The uptake of nC60, B[a]P and mixtures of nC60 and B[a]P into tissues was confirmed by Gas
Yuji Fujita et al.
Bioorganic & medicinal chemistry, 18(3), 1194-1203 (2010-01-12)
The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption
Devivasha Bordoloi et al.
Biomolecules, 9(12) (2019-12-11)
Lung cancer represents the most common cause of cancer deaths in the world, constituting around 11.6% of all new cancer cases and 18.4% of cancer-related deaths. The propensity for early spread, lack of suitable biomarkers for early diagnosis, as well
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