Chrysene

Chrysene[1]
Skeletal structure
Ball-and-stick model of the chrysene molecule
Names
Preferred IUPAC name
Chrysene[2]
Other names
1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzo[a]phenanthrene; NSC 6175; [4]Phenacene
Identifiers
3D model (JSmol)
1909297
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.386 Edit this at Wikidata
EC Number
  • 205-923-4
262600
KEGG
RTECS number
  • GC0700000
UNII
  • InChI=1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H checkY
    Key: WDECIBYCCFPHNR-UHFFFAOYSA-N checkY
  • InChI=1/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H
    Key: WDECIBYCCFPHNR-UHFFFAOYAK
  • c1ccc2c(c1)ccc3c2ccc4c3cccc4
Properties
C18H12
Molar mass 228.294 g·mol−1
Appearance white solid
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[3]
-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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Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula C
18H
12[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

  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. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ Merck Index, 14th edition
  4. ^ Chisholm, Hugh, ed. (1911). "Chrysene" . Encyclopædia Britannica. Vol. 6 (11th ed.). Cambridge University Press. p. 319.
  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 Archived 2016-03-04 at the Wayback Machine
  6. ^ 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 3084482. PMID 21556207.
  7. ^ 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