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Chrysene

Chemical compound

Chemical compound

| NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = Pyrene, Tetracene, Triphenylene

Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula that consists of four fused benzene rings. It is a natural constituent of coal tar, from which it was first isolated and characterized. It is also found in creosote at levels of 0.5–6 mg/kg.

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. 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.

Derivatives

Derivatives of chrysene include tetrahydrochrysene and 2,8-dihydroxyhexahydrochrysene, which are estrogenic compounds. The experimental cancer drug crisnatol is a derivative of chrysene.

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''2259'''.
  2. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  3. ''Merck Index'', 14th edition
  4. {{cite EB1911
  5. Anja Sörensen and Bodo Wichert "Asphalt and Bitumen" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2009. {{doi. 10.1002/14356007.a03_169.pub2http://www.qrpoil.com/site/?bitumen {{Webarchive. link. (2016-03-04)
  6. (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health.
  7. [http://www.atsdr.cdc.gov/toxprofiles/tp69.pdf TOXICOLOGICAL PROFILE FOR POLYCYCLIC AROMATIC HYDROCARBONS]
  8. 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. {{doi. 10.1016/0273-2300(92)90009-X
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polycyclic-aromatic-hydrocarbons iarc-group-2b-carcinogens tetracyclic-compounds pbt-substances
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