B1760
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:
Molecular Weight:
252.31
UNSPSC Code:
12352005
NACRES:
NA.25
PubChem Substance ID:
EC Number:
200-028-5
Beilstein/REAXYS Number:
1911333
MDL number:
Quality Level
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
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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Danger
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Muta. 1B - PBT - Repr. 1B - Skin Sens. 1 - vPvB
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
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