Skip to Content
Merck
All Photos(4)

Key Documents

View All Documentation

B1760

Sigma-Aldrich

Benzo[a]pyrene

≥96% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

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

Looking for similar products? Visit Product Comparison Guide

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.

related product

Product No.
Description
Pricing

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Benzo[k]fluoranthene for fluorescence, ≥99%

Sigma-Aldrich

392251

Benzo[k]fluoranthene

Pyrene 98%

Sigma-Aldrich

185515

Pyrene

Fluoranthene 98%

Sigma-Aldrich

F807

Fluoranthene

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
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
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
View All Related Papers

Articles

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service