Chrysene

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Chrysene[1]
Skeletal structure
Ball-and-stick model of the chrysene molecule
Names
Preferred IUPAC name
Chrysene
Other names
Benzo[a]phenanthrene
1,2-Benzphenanthrene
Identifiers
3D model (JSmol)
1909297
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.386
EC Number 205-923-4
262600
KEGG
RTECS number GC0700000
UNII
Properties
C18H12
Molar mass 228.29 g·mol−1
Appearance Orthorhombic bipyramidal plates
Density 1.274 g/cm3
Melting point 254 °C (489 °F; 527 K)
Boiling point 448 °C (838 °F; 721 K)
Insoluble
Solubility in ethanol 1 g/1300 mL[2]
-166.67·10−6 cm3/mol
Related compounds
Related PAHs
Pyrene, Tetracene, Triphenylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula C
18
H
12
[3] 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.[4]

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[edit]

Chrysene is a constituent of tobacco smoke.[5]

Safety[edit]

As with other PAHs, chrysene is suspected to be a human carcinogen. Some evidence suggests that it causes cancer in laboratory animals,[6] but chrysene is often contaminated with more strongly carcinogenic compounds. Chrysene is estimated to have about 1% of the toxicity of benzopyrene.[7]

Derivatives[edit]

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[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 2259.
  2. ^ Merck Index, 14th edition
  3. ^ Wikisource Chisholm, Hugh, ed. (1911). "Chrysene". Encyclopædia Britannica. 6 (11th ed.). Cambridge University Press. p. 319. 
  4. ^ 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
  5. ^ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC 3084482Freely accessible. PMID 21556207. 
  6. ^ TOXICOLOGICAL PROFILE FOR POLYCYCLIC AROMATIC HYDROCARBONS
  7. ^ 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