Benzo[a]pyrene 

A polycyclic aromatic hydrocarbon (PAH), environmental pollutant and carcinogen. 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.

≥96% (HPLC)

495 °C(lit.)

177-180 °C(lit.)

Operana, T.N., et al., Human CYP1A1GFP expression in transgenic mice serves as a biomarker for environmental toxicant exposure. Toxicol. Sci. 95, 98-107, (2007) abstract

Andrysik, Z., et al., The aryl hydrocarbon receptor-dependent deregulation of cell cycle control induced by polycyclic aromatic hydrocarbons in rat liver epithelial cells. Mutat. Res. 615, 87-97, (2007) abstract

Revel, A., et al., Resveratrol, a natural aryl hydrocarbon receptor antagonist, protects lung from DNA damage and apoptosis caused by benzo[a]pyrene. J. Appl. Toxicol. 23, 255-261, (2003) abstract

Gamper, H.B., et al., Mechanism of benzo[a]pyrene diol epoxide induced deoxyribonucleic acid strand scission. Biochemistry 19, 3948-3956, (1980) abstract

Merck 13,1104

Beil. 5,IV,2687

Aldrich MSDS 1, 163:C / Corp MSDS 1 (1), 366:B / FT-IR 2 (2), 1675:A / FT-IR 1 (1), 969:A / FT-NMR 1 (2), 57:C / IR-Spectra (3), 583:E / IR-Spectra (2), 520:A / NMR-Reference 2 (1), 770:B / RegBook 1 (1), 1157:F / Sax 6, 382 / Sigma FT-IR 1 (2), 308:C / Structure Index 1, 178:D:6

UN 3077 9/PG 3

3

DJ3675000