Chrysene is a

polycyclic aromatic hydrocarbon A Polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced by the incomplete combustion of organic matter— by engine exhaust fumes, tobacco, incine ...

(PAH) with the molecular formula that consists of four fused

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

rings. It is a natural constituent of

coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoria ...

, from which it was first isolated and characterized. It is also found in

creosote Creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood, or fossil fuel. They are typically used as preservatives or antiseptics. Some creosote types w ...

at levels of 0.5–6 mg/kg.Anja Sörensen and Bodo Wichert "Asphalt and Bitumen" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2009. http://www.qrpoil.com/site/?bitumen The name "chrysene" originates from Greek ''Χρύσoς'' (''chrysos''), meaning "gold", and is due to the golden-yellow color of the crystals of the hydrocarbon, thought to be the proper color of the compound at the time of its isolation and characterization. However, high purity chrysene is colorless, the yellow hue being due to the traces of its yellow-orange isomer tetracene, which cannot be separated easily.

Occurrence

Chrysene is a constituent of

tobacco smoke Tobacco smoke is a sooty aerosol produced by the incomplete combustion of tobacco during the smoking of cigarettes and other tobacco products. Temperatures in burning cigarettes range from about 400 °C between puffs to about 900 °C ...

Safety

As with other PAHs, chrysene is suspected to be a human

carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...

. Some evidence suggests that it causes cancer in laboratory animals, but chrysene is often contaminated with more strongly carcinogenic compounds. Chrysene is estimated to have about 1% of the toxicity of benzo(a)pyrene.Ian C.T. Nisbet, Peter K. LaGoy "Toxic equivalency factors (TEFs) for polycyclic aromatic hydrocarbons (PAHs)",

Regulatory Toxicology and Pharmacology ''Regulatory Toxicology and Pharmacology'' is a monthly peer-reviewed scientific journal which covers legal aspects of toxicological and pharmacological regulations. It is published by Elsevier on behalf of the International Society of Regulatory ...

1992, Volume 16, Pages 290-300.

Derivatives

Derivatives of chrysene include tetrahydrochrysene and 2,8-dihydroxyhexahydrochrysene, which are

estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

ic compounds. The experimental cancer drug crisnatol is a derivative of chrysene.

References

{{PAHs Polycyclic aromatic hydrocarbons IARC Group 2B carcinogens Tetracyclic compounds PBT substances

Occurrence

Safety

Derivatives

See also

References