Benzo
'a''yrene (B''a''P or B
) is a
polycyclic aromatic hydrocarbon
A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...
and the result of incomplete combustion of
organic matter
Organic matter, organic material, or natural organic matter refers to the large source of carbon-based compounds found within natural and engineered, terrestrial, and aquatic environments. It is matter composed of organic compounds that have c ...
at temperatures between and . The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C
20H
12 is one of the
benzopyrene
A benzopyrene is an organic compound with the formula C20H12. Structurally speaking, the colorless isomers of benzopyrene are pentacyclic hydrocarbons and are fusion products of pyrene and a phenylene group. Two isomeric species of benzopyrene ...
s, formed by a
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
ring fused to
pyrene
Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is . This yellow solid is the smallest peri-fused PAH (one where the rings are fused through mor ...
. Its diol epoxide metabolites (more commonly known as BPDE) react with and bind to
DNA, resulting in mutations and eventually cancer. It is listed as a
Group 1 carcinogen by the
IARC IARC may refer to:
* International Aerial Robotics Competition
* International Age Rating Coalition
* International Agency for Research on Cancer
* International Arctic Research Center
* Israel Amateur Radio Club
The Israel Amateur Radio Club (IA ...
. In the 18th century a scrotal cancer of chimney sweepers, the
chimney sweeps' carcinoma
Chimney sweep's cancer, also called soot wart, is a squamous cell carcinoma of the skin of the scrotum. It has the distinction of being the first reported form of occupational cancer, and was initially identified by Percivall Pott in 1775. It wa ...
, was already known to be connected to soot.
Description
B