Editing Benzo(a)pyrene (section)

{{Short description|Carcinogenic compound found in smoke and soot}}
{{DISPLAYTITLE:Benzo(''a'')pyrene}}
{{Correct title|reason=bracket|edit=substitution|Benzo[''a'']pyrene}}
{{Chembox
| Watchedfields = changed
| verifiedrevid =443416124
| Name =Benzo[''a'']pyrene
| ImageFile =Benzo-a-pyrene.svg
| ImageSize =
| ImageCaption = [[Skeletal formula]]
| ImageName =Benzo[''a'']pyrene
| ImageFile1 = Benzo(a)pyrene-from-xtal-3D-bs-17.png
| ImageSize1 =
| ImageCaption1 = [[Ball-and-stick model]]
| ImageFile2 = Benzo(a)pyrene-from-xtal-3D-sf.png
| ImageCaption2 = [[Space-filling model]]
| PIN =Benzo[''pqr'']tetraphene<ref name="bluebook">{{cite book | author=Henri A. Favre, Warren H. Powell | title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 | year=2013 | publisher=[[Royal Society of Chemistry]] | isbn = 978-0-85404-182-4 | page=232}}</ref>
| OtherNames = {{ubl|Benz[''a'']pyrene|Benzo[''a'']pyrene|3,4-Benzpyrene|3,4-Benzopyrene|3,4-Benz[''a'']pyrene|3,4-Benzo[''a'']pyrene|Pentacyclo[10.6.2.0<sup>2,7</sup>.0<sup>9,19</sup>.0<sup>16,20</sup>]icosa-1,3,5,7,9,11,13,15,17,19-decaene{{citation needed|date=May 2019}}}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2246
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =C07535
| InChI =1/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
| InChIKey =FMMWHPNWAFZXNH-UHFFFAOYAQ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL =31184
| PubChem = 2336
| RTECS = DJ3675000
| UNNumber = 3077, 3082
| UNII = 3417WMA06D
| EINECS = 200-028-5
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI =1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey =FMMWHPNWAFZXNH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =50-32-8
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =29865
| SMILES =c1ccc2c(c1)cc3ccc4cccc5c4c3c2cc5}}
|Section2={{Chembox Properties
| C=20 | H=12
| Density =1.24 g/cm<sup>3</sup> (25 °C)
| MeltingPtC = 179 <ref name="crc97">{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | pages=3–42 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}</ref>
| MeltingPt_notes =
| BoilingPtC = 495
| BoilingPt_notes =
| Solubility =0.2 to 6.2 μg/L
| MagSus = −135.7·10<sup>−6</sup> cm<sup>3</sup>/mol}}
| Section7 = {{Chembox Hazards
| Hazards_ref =<ref>{{cite web|title=benzo[''a'']pyrene|url=https://pubchem.ncbi.nlm.nih.gov/compound/2336#section=Hazards-Identification|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>
<!-- (data page) -->
| ExternalSDS = 
| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|317|340|350|360|410}}
| PPhrases = {{P-phrases|201|202|261|272|273|280|281|302+352|308+313|321|333+313|363|391|405|501}}
}}
}}

'''Benzo[''a'']pyrene''' ('''B''a''P''' or '''B[a]P''') is a [[polycyclic aromatic hydrocarbon]] and the result of incomplete combustion of [[organic matter]] at temperatures between {{convert|300|°C|°F}} and {{convert|600|°C|°F}}. The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C<sub>20</sub>H<sub>12</sub> is one of the [[benzopyrene]]s, formed by a [[benzene]] ring fused to [[pyrene]]. Its [[diol]] [[epoxide]] metabolites, more commonly known as BPDE, react with and bind to [[DNA]], resulting in mutations and eventually cancer. It is listed as a [[List of IARC Group 1 carcinogens|Group 1 carcinogen]] by the [[International Agency for Research on Cancer|IARC]]. In the 18th century a scrotal cancer of chimney sweepers, the [[chimney sweeps' carcinoma]], was already known to be connected to soot.