Chrysene

Chrysene^[1]

Names
Preferred IUPAC name Chrysene
Other names Benzo[a]phenanthrene 1,2-Benzphenanthrene
Identifiers
CAS Number	218-01-9
3D model (Jmol)	Interactive image
Beilstein Reference	1909297
ChEBI	CHEBI:51687
ChEMBL	ChEMBL85685
ChemSpider	8817
ECHA InfoCard	100.005.386
EC Number	205-923-4
Gmelin Reference	262600
KEGG	C14222
PubChem	10457109
RTECS number	GC0700000
UNII	084HCM49PT
InChI 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 Key: WDECIBYCCFPHNR-UHFFFAOYSA-N 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
SMILES c1ccc2c(c1)ccc3c2ccc4c3cccc4
Properties
Chemical formula	C18H12
Molar mass	228.29 g·mol^−1
Appearance	Orthorhombic bipyramidal plates
Density	1.274 g/cm^3
Melting point	254 °C (489 °F; 527 K)
Boiling point	448 °C (838 °F; 721 K)
Solubility in water	Insoluble
Solubility in ethanol	1 g/1300 mL[2]
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
18H
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

More than 20% of the carbon in the universe may be associated with PAHs, which have been implicated as starting materials for the formation of life. PAHs seem to have been formed shortly after the Big Bang, are widespread throughout the universe, and are associated with new stars and exoplanets.^[5][6]

Safety

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

• Phenanthrene

References

1. Merck Index, 11th Edition, 2259.
2. Merck Index, 14th edition
3.  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. Hoover, Rachel (February 21, 2014). "Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That". NASA. Retrieved February 22, 2014.
6. NASA Ames PAH IR Spectroscopic Database
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