{{short description|Chemical compound}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 455522715 | Reference = <ref>''Merck Index'', 11th Edition, '''2259'''.</ref> | ImageFile = Chryzen.svg | ImageName = Skeletal structure | ImageFile1 = Chrysene molecule ball.png | ImageAlt1 = Ball-and-stick model of the chrysene molecule | PIN = Chrysene<ref>{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> | OtherNames = 1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzo[a]phenanthrene; NSC 6175; [4]Phenacene |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8817 | InChIKey = WDECIBYCCFPHNR-UHFFFAOYAK | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 85685 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WDECIBYCCFPHNR-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 218-01-9 | EINECS = 205-923-4 | PubChem = 9171 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 084HCM49PT | SMILES = c1ccc2c(c1)ccc3c2ccc4c3cccc4 | 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 | RTECS = GC0700000 | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 51687 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C14222 | Beilstein = 1909297 | Gmelin = 262600 }} |Section2={{Chembox Properties | C=18 | H=12 | Appearance = white solid | Density = 1.274 g/cm<sup>3</sup> | MeltingPtC = 254 | MeltingPt_notes = | BoilingPtC = 448 | BoilingPt_notes = | Solubility = Insoluble | SolubleOther = 1 g/1300 mL<ref>''Merck Index'', 14th edition</ref> | Solvent = ethanol | pKa = | pKb = | MagSus = −166.67·10<sup>−6</sup> cm<sup>3</sup>/mol}} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = Pyrene, Tetracene, Triphenylene | OtherFunction_label = PAHs | OtherCompounds = }} }}

'''Chrysene''' is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula {{chem|C|18|H|12}}<ref>{{cite EB1911|wstitle=Chrysene|volume=6|page=319}}</ref> 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&nbsp;mg/kg.<ref name=Ullmann>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 {{Webarchive|url=https://web.archive.org/web/20160304042118/http://www.qrpoil.com/site/?bitumen |date=2016-03-04 }}</ref>

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.<ref name="TalhoutSchulz2011">{{cite journal |last1=Talhout |first1=Reinskje |last2=Schulz|first2=Thomas |last3=Florek |first3=Ewa |last4=Van Benthem |first4=Jan |last5=Wester |first5=Piet |last6=Opperhuizen |first6=Antoon |title=Hazardous Compounds in Tobacco Smoke |journal=International Journal of Environmental Research and Public Health |volume=8 |issue=12|year=2011 |pages=613–628 |issn=1660-4601 |doi=10.3390/ijerph8020613 |pmid=21556207 |pmc=3084482|doi-access=free }}</ref>

==Safety== As with other PAHs, chrysene is suspected to be a human carcinogen. Some evidence suggests that it causes cancer in laboratory animals,<ref>[http://www.atsdr.cdc.gov/toxprofiles/tp69.pdf TOXICOLOGICAL PROFILE FOR POLYCYCLIC AROMATIC HYDROCARBONS]</ref> but chrysene is often contaminated with more strongly carcinogenic compounds. Chrysene is estimated to have about 1% of the toxicity of benzo(a)pyrene.<ref>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}}</ref>

==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== <references/>

{{PAHs}}

Category:Polycyclic aromatic hydrocarbons Category:IARC Group 2B carcinogens Category:Tetracyclic compounds Category:PBT substances