Chrysene

Chrysene^[1]
Names
	Preferred IUPAC name Chrysene
	Other names 1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzo[a]phenanthrene; NSC 6175; [4]Phenacene
Identifiers
CAS Number	218-01-9 ;
3D model (JSmol)	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 CID	10457109;
RTECS number	GC0700000;
UNII	084HCM49PT ;
CompTox Dashboard (EPA)	DTXSID0022432 ;
	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	228.294 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)
Solubility in water	Insoluble
Solubility in ethanol	1 g/1300 mL
Magnetic susceptibility (χ)	-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). verify (what is ?) Infobox references

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.

References

^ Merck Index, 11th Edition, 2259.
^ 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.
^ Merck Index, 14th edition
^ Chisholm, Hugh, ed. (1911). "Chrysene" . Encyclopædia Britannica. Vol. 6 (11th ed.). Cambridge University Press. p. 319.
^ 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.pub2 http://www.qrpoil.com/site/?bitumen Archived 2016-03-04 at the Wayback Machine
^ 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.
^ 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. doi:10.1016/0273-2300(92)90009-X

[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.

[Ullmann-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.pub2 http://www.qrpoil.com/site/?bitumen Archived 2016-03-04 at the Wayback Machine

[TalhoutSchulz2011-6] 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

[4]

[5]

[1]

[2]

[3]

[6]

[7]

[8]

Chrysene

Contents

Occurrence

Safety

Derivatives

See also

References

Names


Preferred IUPAC name Chrysene^[2]
Other names 1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzo[a]phenanthrene; NSC 6175; [4]Phenacene
Identifiers
CAS Number	218-01-9^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1909297
ChEBI	CHEBI:51687^Y
ChEMBL	ChEMBL85685^Y
ChemSpider	8817^Y
ECHA InfoCard	100.005.386
EC Number	205-923-4
Gmelin Reference	262600
KEGG	C14222^Y
PubChem CID	10457109
RTECS number	GC0700000
UNII	084HCM49PT^Y
CompTox Dashboard (EPA)	DTXSID0022432
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^Y Key: WDECIBYCCFPHNR-UHFFFAOYSA-N^Y 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	228.294 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)
Solubility in water	Insoluble
Solubility in ethanol	1 g/1300 mL^[3]
Magnetic susceptibility (χ)	-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). N verify (what is ^YN ?) Infobox references