fluoranthene
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461101697
| Name = Fluoranthene
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageFile1 = Fluoranthene.svg
| ImageClass1 = skin-invert-image
| ImageSize1 = 130px
| ImageName1 = Chemical structure of fluoranthene
| ImageFile2 = Fluoranthene 3D.png
| ImageClass2 = bg-transparent
| ImageSize2 = 150px
| ImageName2 = Ball-and-stick model of fluoranthene
| ImageFile3 = Fluoranthene sample.JPG
| ImageSize3 = 150px
| PIN = Fluoranthene{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | pages = 206, 503 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}
| OtherNames = Benzo[jk]fluorene
Tetracyclo[7.6.1.05,16.010,15]hexadeca-1,3,5,7,9(16),10,12,14-octaene{{citation needed|date=May 2019}}
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 360UOL779Z
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33083
| SMILES = c1ccc-2c(c1)-c3cccc4c3c2ccc4
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8800
| InChI = 1/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H
| InChIKey = GVEPBJHOBDJJJI-UHFFFAOYAL
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 355014
| Beilstein = 1907918
| Gmelin = 262216
| PubChem = 9154
| EC_number = 205-912-4
| UNNumber = 1325, 3082
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GVEPBJHOBDJJJI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 206-44-0
| RTECS =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19425
}}
|Section2={{Chembox Properties
| C=16|H=10
| Appearance = Yellow to green needles
| Density = 1.252 g/cm3 (0 °C), solid
| Solubility = 265 μg/L (25 °C)
| MeltingPtC = 110.8
| MeltingPt_notes =
| BoilingPtC = 375
| BoilingPt_notes =
| Viscosity = 0.652 cP at 20 °C
| MagSus = −138.0·10−6 cm3/mol
}}
|Section3={{Chembox Structure
| MolShape = Planar
| Dipole = 0.34 D
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = warning
| HPhrases = {{HPhrases|H302|H410}}
| PPhrases = {{PPhrases|P273|P501}}
| GHS_ref = GHS: [https://gestis.dguv.de/data?name=030010 GESTIS 030010]
| FlashPtC = 210
| AutoignitionPtC =
}}
|Section8={{Chembox Related
| OtherFunction_label = hydrocarbons
| OtherFunction =
| OtherCompounds =
}}
}}
Fluoranthene is a polycyclic aromatic hydrocarbon (PAH). The molecule can be viewed as the fusion of naphthalene and benzene unit connected by a five-membered ring. The chemical formula is {{chem2|C16H10}}. Although samples are often pale yellow, the compound is colorless. It is soluble in nonpolar organic solvents.Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a13_227}} It is a member of the class of PAHs known as non-alternant PAHs because it has rings other than those with six carbon atoms. It is a structural isomer of the alternant PAH pyrene. It is not as thermodynamically stable as pyrene. Its name is derived from its fluorescence under UV light.
Occurrence
=Pollutant=
Fluoranthene is one of the U.S. Environmental Protection Agency's 16 priority pollutant PAHs. Fluoranthene has been classified by the International Agency for Research on Cancer as a group 3 carcinogen, "not classifiable as to its carcinogenicity to humans"[1], however it was found to possess carcinogenic properties in case of newborn mice according to short-term lung tumor assay (Busby et al., 1984).{{cite web |url=http://cira.ornl.gov/documents/FLUORANT.pdf |title=Archived copy |access-date=2012-07-30 |url-status=dead |archive-url=https://web.archive.org/web/20120911233743/http://cira.ornl.gov/documents/FLUORANT.pdf |archive-date=2012-09-11 }} In 2019, fluoranthene was added to the Candidate List of Substances of Very High Concern (SVHCs) due to its persistent, bioaccumulative and toxic (PBT) and very persistent and very bioaccumulative (vPvB) properties.{{cite web |url=https://echa.europa.eu/-/six-new-substances-added-to-the-candidate-list |title=Six new substances added to the Candidate List ECHA/PR/19/01 |access-date=2019-01-17 }} Its occurrence in food has been assessed.
Its biodegradation has been elucidated. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.{{cite journal |doi=10.3390/ijerph6010278|doi-access=free|title=Bacterial Degradation of Aromatic Compounds|year=2009|last1=Seo|first1=Jong-Su|last2=Keum|first2=Young-Soo|last3=Li|first3=Qing|journal=International Journal of Environmental Research and Public Health|volume=6|issue=1|pages=278–309|pmid=19440284|pmc=2672333}}
References
External links
- [https://web.archive.org/web/20060518002254/http://www.npi.gov.au/database/substance-info/profiles/74.html National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet]
- [http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=206%2d44%2d0 Chemical Profile for FLUORANTHENE from Scorecard]
- [https://web.archive.org/web/20091225060952/http://www.speclab.com/compound/c206440.htm FLUORANTHENE Chemical Fact Sheet by Spectrum Laboratories]
- [http://monographs.iarc.fr/ENG/Classification/ClassificationsAlphaOrder.pdf]
- [https://web.archive.org/web/20120911233743/http://cira.ornl.gov/documents/FLUORANT.pdf TOXICITY SUMMARY FOR FLUORANTHENE August 1993]
{{PAHs}}
Category:Polycyclic aromatic hydrocarbons