Benzopyrene

Benzo[a]pyrene
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
Benzo[e]pyrene
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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A benzopyrene is an organic compound with the formula C20H12. Structurally, these colourless pentacyclic hydrocarbons are related to pyrene by fusion of a phenylene group. Two isomeric species are benzo[a]pyrene and the less common benzo[e]pyrene. Related compounds include cyclopentapyrenes, dibenzopyrenes, indenopyrenes and naphthopyrenes.

Benzopyrene is a component of pitch. Related pentacyclic aromatic species include picene, benzofluoranthenes, and perylene.[1] Benzopyrenes are problematic because they intercalate into DNA, interfering with transcription. They are considered pollutants and carcinogens.

They can be found in coal tar (after a forest fire), after eruption of volcanoes, in cigarette smoke, wood smoke, and in burnt foods such as coffee.

Evidence exists to link benzo[a]pyrene to the formation of lung cancer.[2]

References

  1. ^ W. D. Betts "Tar and Pitch" in Kirk‑Othmer Encyclopedia of Chemical Technology, 1997, John Wiley & Sons, New York. doi: 10.1002/0471238961.20011802052020.a01
  2. ^ Denissenko, Pao, A, Tang, M, et al 1996 "Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in P53." Science 274(430-432) http://www.sciencemag.org/cgi/content/abstract/274/5286/430?ijkey=7dd94e096ea549bac90bce0ec51acb6422cbb1a4&keytype2=tf_ipsecsha )