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Merck

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:
50-32-8
Molecular Weight:
252.31
UNSPSC Code:
12352005
NACRES:
NA.25
PubChem Substance ID:
24891610
EC Number:
200-028-5
Beilstein/REAXYS Number:
1911333
MDL number:
MFCD00003602

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Product Name

Benzo[a]pyrene, ≥96% (HPLC)

InChI key

FMMWHPNWAFZXNH-UHFFFAOYSA-N

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

SMILES string

c1ccc2c(c1)cc3ccc4cccc5ccc2c3c45

assay

≥96% (HPLC)

form

solid

bp

495 °C (lit.)

mp

177-180 °C (lit.)

Quality Level

200

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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.

signalword

Danger

Hazard Classifications

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

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCM1224
SLCL9348
SLCK8337
SLCK8342
SLCK8338

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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
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
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
A P Wolterbeek et al.
Cancer letters, 89(1), 107-116 (1995-02-10)
Several experimental models have been developed to study respiratory tract carcinogenesis. The most widely applied in vivo model uses Syrian golden hamsters which receive intratracheal instillations of a suspension of benzo[a]pyrene (B[a]P) particles attached to ferric-oxide (Fe2O3) particles in saline;
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