Benzo(a)pyrene

Benzo(a)pyrene

Benzopyrene is a polycyclic aromatic hydrocarbon found in coal tar with the formula C₂₀H₁₂. Its metabolites are mutagenic and highly carcinogenic, and it is listed as a Group 1 carcinogen by the IARC. The compound is one of the benzopyrenes, formed by a benzene ring fused to pyrene, and is the result of incomplete combustion at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F).

Chimney sweeps suffered from scrotal cancers in the 18th century, and frequent skin cancers were noted among fuel industry workers in the 19th century. In 1933, benzopyrene was determined to be the compound responsible for these cases, and its toxicity was demonstrated when skin tumors occurred in laboratory animals repeatedly painted with coal tar. When the body attempts to metabolise benzopyrene, the resulting diol epoxide reacts and binds to DNA, resulting in mutations and eventually cancer.