Chrysene is a
polycyclic aromatic hydrocarbon (PAH) with the molecular formula that consists of four fused
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 ...
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 pso ...
, from which it was first isolated and characterized. It is also found in
creosote 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.
Safety
As with other PAHs, chrysene is suspected to be a human
carcinogen
A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive sub ...
. 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 1992, Volume 16, Pages 290-300. ]
Derivatives
Derivatives of chrysene include
tetrahydrochrysene and
2,8-dihydroxyhexahydrochrysene, which are
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...
ic compounds. The experimental cancer drug
crisnatol is a derivative of chrysene.
See also
*
Phenanthrene
References
{{PAHs
Polycyclic aromatic hydrocarbons
IARC Group 2B carcinogens
Tetracyclic compounds
PBT substances