| Revision as of 12:37, 14 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
Latest revision as of 15:47, 19 December 2024 edit undo176.200.94.39 (talk)No edit summaryTags: Mobile edit Mobile web edit |
| (63 intermediate revisions by 37 users not shown) |
| Line 1: |
Line 1: |
|
|
{{short description|Chemical compound}} |
|
{{chembox |
|
{{chembox |
|
| Verifiedfields = changed |
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 455519681 |
|
| verifiedrevid = 455522715 |
|
| Reference = <ref>''Merck Index'', 11th Edition, '''2259'''.</ref> |
|
| Reference = <ref>'']'', 11th Edition, '''2259'''.</ref> |
|
| ImageFile = Chrysene structure.png |
|
| ImageFile = Chryzen.svg |
|
| ImageName = Skeletal structure |
|
| ImageName = Skeletal structure |
|
| ImageFile1 = Chrysene-3D-balls.png |
|
| ImageFile1 = Chrysene molecule ball.png |
|
| ImageName1 = Ball-and-stick model |
|
| ImageAlt1 = Ball-and-stick model of the chrysene molecule |
|
|
| PIN = Chrysene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
|
| IUPACName = Chrysene |
|
|
| OtherNames = Benzophenanthrene<br>1,2-Benzphenanthrene |
|
| OtherNames = 1,2-Benzophenanthrene; 1,2-Benzphenanthrene; Benzophenanthrene; NSC 6175; Phenacene |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| Abbreviations = |
|
| Abbreviations = |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 8817 |
|
| ChemSpiderID = 8817 |
|
| InChIKey = WDECIBYCCFPHNR-UHFFFAOYAK |
|
| InChIKey = WDECIBYCCFPHNR-UHFFFAOYAK |
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL = <!-- blanked - oldvalue: 85685 --> |
|
| ChEMBL = 85685 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| 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 |
|
| 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 |
| Line 23: |
Line 25: |
|
| CASNo = 218-01-9 |
|
| CASNo = 218-01-9 |
|
| EINECS = 205-923-4 |
|
| EINECS = 205-923-4 |
|
| PubChem = 10457109 |
|
| PubChem = 9171 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 084HCM49PT |
|
| UNII = 084HCM49PT |
| Line 34: |
Line 36: |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = C14222 |
|
| KEGG = C14222 |
|
|
| Beilstein = 1909297 |
|
| ATCCode_prefix = |
|
|
|
| Gmelin = 262600 |
|
| ATCCode_suffix = |
|
|
|
}} |
|
| ATC_Supplemental =}} |
|
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
|
| C=18 | H=12 |
|
| Formula = C<sub>18</sub>H<sub>12</sub> |
|
|
|
| Appearance = white solid |
|
| MolarMass = 228.28 |
|
|
| Appearance = Orthorhombic bipyramidal plates |
|
|
| Density = 1.274 g/cm<sup>3</sup> |
|
| Density = 1.274 g/cm<sup>3</sup> |
|
| MeltingPtC = 254 |
|
| MeltingPtC = 254 |
|
| Melting_notes = |
|
| MeltingPt_notes = |
|
| BoilingPtC = 448 |
|
| BoilingPtC = 448 |
|
| Boiling_notes = |
|
| BoilingPt_notes = |
|
| Solubility = Insoluble |
|
| Solubility = Insoluble |
|
| SolubleOther = 1 mg/1300 mL |
|
| SolubleOther = 1 g/1300 mL<ref>''Merck Index'', 14th edition</ref> |
|
| Solvent = ] |
|
| Solvent = ] |
|
| pKa = |
|
| pKa = |
|
| pKb = }} |
|
| pKb = |
|
|
| MagSus = -166.67·10<sup>−6</sup> cm<sup>3</sup>/mol}} |
|
| Section7 = {{Chembox Hazards |
|
|Section7={{Chembox Hazards |
|
| EUClass = |
|
|
| EUIndex = |
|
|
| MainHazards = |
|
| MainHazards = |
|
| NFPA-H = |
|
| NFPA-H = |
|
| NFPA-F = |
|
| NFPA-F = |
|
| NFPA-R = |
|
| NFPA-R = |
|
| NFPA-O = |
|
| NFPA-S = |
|
| RPhrases = |
|
|
| SPhrases = |
|
|
| RSPhrases = |
|
|
| FlashPt = |
|
| FlashPt = |
|
| Autoignition = |
|
| AutoignitionPt = |
|
| ExploLimits = |
|
| ExploLimits = |
|
| PEL = }} |
|
| PEL = }} |
|
| Section8 = {{Chembox Related |
|
|Section8={{Chembox Related |
|
| OtherAnions = |
|
| OtherAnions = |
|
| OtherCations = |
|
| OtherCations = |
|
| OtherFunctn = |
|
| OtherFunction = |
|
], ], ] |
|
], ], ] |
|
| Function = PAHs |
|
| OtherFunction_label = PAHs |
|
| OtherCpds = |
|
| OtherCompounds = |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Chrysene''' is a ] (PAH) with the molecular formula {{chem|C|18|H|12}} that consists of four fused ] rings. It is a natural constituent of ], from which it was first isolated and characterized. It is also found in ], a chemical used to preserve wood. |
|
'''Chrysene''' is a ] (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 ] rings. It is a natural constituent of ], from which it was first isolated and characterized. It is also found in ] at levels of 0.5–6 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> |
|
|
|
|
Chrysene is formed in small amounts during the burning or distillation of coal, crude oil, and plant material. |
|
|
|
|
|
|
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 ], which cannot be separated easily. |
|
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 ], which cannot be separated easily. |
|
|
|
|
|
==Use== |
|
==Occurrence== |
|
|
|
|
Chrysene is used in the manufacture of some dyes. |
|
|
|
Chrysene is a constituent of ].<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== |
|
==Safety== |
|
As with other PAHs, chrysene is suspected to be a human ]. It is known to cause cancer in laboratory animals.<ref></ref> |
|
As with other PAHs, chrysene is suspected to be a human ]. Some evidence suggests that it causes cancer in laboratory animals,<ref></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)", ] 1992, Volume 16, Pages 290-300. {{doi|10.1016/0273-2300(92)90009-X}}</ref> |
|
|
|
|
|
==Derivatives== |
|
|
] of chrysene include ] and ], which are ]ic compounds. The experimental cancer drug ] is a derivative of chrysene. |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
|
|
|
==References== |
|
==References== |
| Line 95: |
Line 97: |
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|