Chrysene
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
| Template:Longitem | 1909297 |
| ChEBI | Template:Unbulleted list |
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| EC Number | Template:Unbulleted list |
| Template:Longitem | 262600 |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | white solid |
| Density | 1.274 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Solubility in ethanol | 1 g/1300 mL[3] |
| Template:Longitem | −166.67·10−6 cm3/mol |
| Template:Longitem | Pyrene, Tetracene, Triphenylene |
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Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula Template:Chem/link[4] 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.[5]
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.[6]
Safety
As with other PAHs, chrysene is suspected to be a human carcinogen. Some evidence suggests that it causes cancer in laboratory animals,[7] but chrysene is often contaminated with more strongly carcinogenic compounds. Chrysene is estimated to have about 1% of the toxicity of benzo(a)pyrene.[8]
Derivatives
Derivatives of chrysene include tetrahydrochrysene and 2,8-dihydroxyhexahydrochrysene, which are estrogenic compounds. The experimental cancer drug crisnatol is a derivative of chrysene.
See also
References
- ↑ Merck Index, 11th Edition, 2259.
- ↑ Script error: No such module "citation/CS1".
- ↑ Merck Index, 14th edition
- ↑ Template:Cite EB1911
- ↑ Anja Sörensen and Bodo Wichert "Asphalt and Bitumen" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2009. Script error: No such module "CS1 identifiers".http://www.qrpoil.com/site/?bitumen Script error: No such module "webarchive".
- ↑ Script error: No such module "Citation/CS1".
- ↑ TOXICOLOGICAL PROFILE FOR POLYCYCLIC AROMATIC HYDROCARBONS
- ↑ 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. Script error: No such module "CS1 identifiers".
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