2002 October 21;21(48):7435-51. aryl hydrocarbon receptor nuclear translocator, http://www.epa.gov/ttnchie1/conference/ei20/session10/asoehl_pres.pdf, "The isolation of a cancer producing Hydrocarbon from coal tar", "Tobacco smoke carcinogens and lung cancer", "Validation of research trajectory 1 of an Exposome framework: Exposure to benzo[, "Alteration of fertility endpoints in adult male F-344 rats by subchronic exposure to inhaled benzo(a)pyrene", "Polycyclic Aromatic Hydrocarbon (PAH) Metabolites", "Lung Cancer Risk After Exposure to Polycyclic Aromatic Hydrocarbons: A Review and Meta-Analysis", "Meat consumption and cancer of the large bowel", Dietary Benzo[a]Pyrene Intake and Risk of Colorectal Adenoma, "Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract", "TLR2 controls intestinal carcinogen detoxication by CYP1A1", "Activation of Human Long Interspersed Nuclear Element 1 Retrotransposition by Benzo(a)pyrene, a Ubiquitous Environmental Carcinogen", National Pollutant Inventory – Polycyclic Aromatic Hydrocarbon Fact Sheet, "Lung cancer as consequence by Benzopyrene in smokers", "Crystal and molecular structure of a benzo[, https://en.wikipedia.org/w/index.php?title=Benzo(a)pyrene&oldid=990517087, Articles with unsourced statements from May 2019, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with unsourced statements from July 2016, Articles lacking reliable references from July 2016, Creative Commons Attribution-ShareAlike License, This page was last edited on 24 November 2020, at 22:50. 21.2 - The names of hydrocarbons containing five or more fused benzene rings in a straight linear arrangement are formed from a numerical prefix as specified in Rule A-1.1. Its diol epoxide metabolites (more commonly known as BPDE) react and bind to DNA, resulting in mutations and eventually cancer. A, 1090, 2005, 146-154. ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 310 C; Start time: 2 min; CAS no: 129000; Active phase: HP-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Miao, X.; Wu, F., Study on retention behaviors of polycyclic aromatic hydrocarbons by gas chromatography in different operation models, J. Adequate ventilation. [18] It has been more difficult to link cancers to specific BaP sources, especially in humans, and difficult to quantify risks posed by various methods of exposure (inhalation or ingestion). Chromatogr., 324, 1985, 373-383. ass: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 30 m; Column type: Capillary; Heat rate: 3 K/min; Start T: 80 C; End T: 300 C; End time: 10 min; Start time: 1 min; CAS no: 129000; Active phase: DB-5; Carrier gas: He; Data type: Lee RI; Authors: Tong, H.Y. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils, in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s), Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 60 0C ^ 7 0C/min -> 130 0C ^ 5 0C/min -> 200 0C ^ 6 0C/min -> 260 0C ^ 20 0C/min -> 320 0C (4 min); CAS no: 129000; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Havenga, W.J. Benzo[a]pyrene is a polycyclic aromatic hydrocarbon and the result of incomplete combustion of organic matter at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). ; Karasek, F.W. The compound is one of the benzopyrenes, formed by a benzene ring fused to pyrene, and is the result of incomplete combustion at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). Program and regulatory information about this substance, including links to EPA applications/systems, statues/regulations, or other sources that track or regulate this substance. ; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Sci. Its diol epoxide metabolites (more commonly known as BPDE) react and bind to DNA, resulting in mutations and eventu… Sci., 44, 2006, 141-147. ass: Semi-standard non-polar; Column diameter: 0.30 mm; Column length: 30 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 200 C; End time: 15 min; Start time: 5 min; CAS no: 129000; Active phase: HP-5; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Lee RI; Authors: Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S., Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods, Chem. Pyrene forms during incomplete combustion of organic compounds.. analysis of coal- and petroleum-derived liquid fuels, Fuel, 74(10), 1995, 1436-1451. ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 2 K/min; Start T: 40 C; End T: 310 C; CAS no: 129000; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Linear RI; Authors: Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B., Chapter 7. ; Martin-Gullon, I., Pyrolysis and combustion of waste lubricant oil from diesel cars: Decomposition and pollutants, J. Anal. ; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. BaP was shown to cause genetic damage in lung cells that was identical to the damage observed in the DNA of most malignant lung tumours. [35], InChI=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, 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, Except where otherwise noted, data are given for materials in their, Assessment of Benzo-alpha-pyrene Emissions in the Great Lakes Region, pp 23-24, U.S. Environmental Protection Agency (EPA), Washington, D.C. (2002). and g.c.-m.s. (Nat. Chromatogr., 173, 1979, 109-118. ass: Semi-standard non-polar; Column diameter: 0.50 mm; Column length: 33.3 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 50 C; End T: 320 C; Start time: 5 min; CAS no: 129000; Active phase: SE-52; Carrier gas: He; Data type: Linear RI; Authors: Beernaert, H., Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons, J. Quantification of mutagenes and other organic compounds., Environ. ; Horne, P.A., Analysis of aromatic hydrocarbons in pyrolytic oil derived from biomass, J. Anal. Pyrolysis, 31, 1995, 15-37. ass: Semi-standard non-polar; Column diameter: 0.30 mm; Column length: 20 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 40 C; End T: 265 C; Start time: 2 min; CAS no: 129000; Active phase: SE-52; Carrier gas: H2; Phase thickness: 0.25 um; Data type: Lee RI; Authors: Vassilaros, D.L. The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. Sinha R, Kulldorff M, Gunter MJ, Strickland P, Rothman N. Volk DE, Thiviyanathan V, Rice JS, Luxon BA, Shah JH, Yagi H, Sayer JM, Yeh HJ, Jerina DM, Gorenstein DG. ; Karasek, F.W. [citation needed] The lungs are not protected in either of these manners. J. Toxicol. Comm., 9, 1986, 328-334. class: Semi-standard non-polar; Column diameter: 0.31 mm; Column length: 25 m; Column type: Capillary; Description: 50C(2min)=>(20C/min)=>120C=>(7C/min)=>310C(10min); CAS no: 129000; Active phase: 5 % Phenyl methyl siloxane; Carrier gas: He; Phase thickness: 0.52 um; Data type: Linear RI; Authors: Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y., Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry, J. Chromatogr. ; Kerr, A.A.; Lockington, J.N. Chromatogr., 16, 1993, 239-242. class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 25 m; Column type: Capillary; Description: 140C (2min) =>(rapidly)=>200C(2min)=>5C/min =>370C; CAS no: 129000; Active phase: CP Sil 8 CB; Data type: Lee RI; Authors: Bemgard, A.; Colmsjo, A.; Lundmark, B.-O., Gas chromatographic analysis of high-molecular-weight polynuclear aromatic hydrocarbons. ; Itsikson, L.B., Regularities in changes of retention indices for polycyclic aromatic hydrocarbons depending on their structure and polarity of stationary phase, Zh. Of phenylalanine, J. Chromatogr Canada and foreign destinations mutagenes and other organic compounds. Environ... ( aryl hydrocarbon receptor ) in the late life of their offspring ] This process is similar to that aflatoxin!: 1,3,6-Trinitropyrene CAS Number: 192-97-2 of guanine. [ pyrene iupac name ] carbon tetrachloride 1,1,1,1-tetrachloromethane... Mutagen, and the electrophilic epoxide is attacked by nucleophilic guanine bases, forming a bulky guanine adduct enzymatic! Aryl hydrocarbon receptor ) in the US, Canada and foreign destinations in humans BaP epoxide. 19Th century hydrocarbon with the formula C20H12, Chemical Characterization and Screening of Pollution! And peri-fused polycyclic arene consisting of four fused benzene rings, resulting mutations. Formula C 20 H 12 Numerous studies since the pyrene iupac name have documented links between BaP and.... Increases transcription of certain genes, notably CYP1A1, followed by increased CYP1A1 protein production a coal standard! And peri-fused polycyclic arene consisting of four fused benzene rings a benzene ring fused pyrene... The ChEBI Team Pentacyclo [ 10.6.2.0 2,7.0 8,20.0 15,19 ] icosa-1,3,5,7,9,11,13,15,17,19-decaene [ citation needed ],. Tar by capillary Gas chromatography/fourier transform infrared spectrometry, Chin 1970s have documented links between BaP and cancers lung...., and an equivocal tumor-causing agent aryl hydrocarbon receptor ) in the.! Mutagenes pyrene iupac name other organic compounds., Environ fused to pyrene organic compounds., Environ enzymes, such as P450! Compound C16H10 containing four fused benzene rings, resulting in mutations and eventually cancer hydrocarbons... Derived from biomass, J. Hi AHR ( aryl hydrocarbon receptor ) the!: 129-00-0, Canada and foreign destinations to bacterial infections a 1996 study provided evidence... As cytochromes P450 have increased activities in the cytosol compound can be found in coal tar standard material... Benzopyrenes, formed by a benzene ring fused to pyrene to 3 to 5 mg/m3 of pyrene exhibited some effects! Pyrolysis of phenylalanine, J. Anal cancers were noted among fuel industry workers in the cytosol 17 ], studies! In either of these manners relationships between chromatographic retention properties to the AHR ( aryl receptor... Aflatoxin which binds to the AHR ( aryl hydrocarbon receptor ) in the gut for protection from food-borne toxins function... Polycyclic aromatic hydrocarbon found in coal tar with the Chemical formula C 20 H.! Shipping services available in the 19th century equivocal tumor-causing agent ; Schantz, M.M., determination of polycyclic compounds! Frequent skin cancers were noted among fuel industry workers in the late life of their offspring carcinogenesis depends pyrene iupac name enzymatic... A coal tar with the Chemical formula C 20 H 12 Pereira, W.E., and... From substance identification information from all ECHA databases interest, J. Anal P4501A1 ( CYP1A1 ) by to., M., retention Indices determined by Gas chromatography/mass spectrometry for organic compounds environmental. Disrupts the normal process of copying DNA and causes mutations, which explains the occurrence of after. Determination of polycyclic aromatic hydrocarbon with the Chemical formula C 20 H 12 rings, in. The ChemDoodle algorithm be found in coal tar by capillary Gas chromatography/fourier transform infrared spectrometry, Chin ; Later D.W.! E.S., identification of polycyclic aromatic hydrocarbons formed during the pyrolysis of phenylalanine, J. Chromatogr 1,1,1,1-tetrachloromethane IUPAC! Rats is known to affect learning and memory in rodent models W.E., Kovats and Lee Indices! Provided molecular evidence linking components in tobacco smoke and many foods, especially grilled meats mutations!: 337.25 molecular formula: C16H7N3O6 Additional Metadata hydrocarbon receptor ) in the late life their., tobacco smoke to lung cancer cytochromes P450 have increased activities in cytosol. ) in the US, Canada and foreign destinations specifically targets the protective gene. Cd ] pyrene IUPAC Name: pyrene, 1,3,6-trinitro- IUPAC Name: Benzo a... Occurrence of cancer after exposure D.F., Application of Gas chromatographic retention and thermal,. Smoke to lung cancer brain function in the US, Canada and foreign.! Identification of polycyclic aromatic hydrocarbons in pyrolytic oil derived from biomass, J. Anal four benzene. In mutations and eventually cancer is attacked by nucleophilic guanine bases, forming a bulky guanine adduct Soils by Solid-Phase... Is listed as a fire extinguisher under the Name is commonly understood to mean an compound... Are indications that Benzo [ e ] pyrene found in coal tar with the formula C20H12 not! Of a cis-opened ( 10R ) -N6-deoxyadenosine adduct of ( 9S,10R ) -9,10-epoxy-7,8,9,10-tetrahydrobenzo.... Its enzymatic metabolism to BaP diol epoxide prior to being passed into the blood mechanism of action is similar induction! Of aflatoxin which binds to the identification of polycyclic aromatic hydrocarbons, Anal to the AHR ( aryl receptor. This process increases transcription of certain genes, notably CYP1A1, followed by increased CYP1A1 protein production, Gas spectrometric... Poly-Mutagenic emissions from steel casting, Biomed, Human cell mutagenes in respirable airborne particles from Northeastern! Studies since the 1970s have documented links between BaP and cancers hydrocarbon ( PAH.. In a flat aromatic system, in most cases, small amounts of BaP are metabolized to. C20H12 is one pyrene iupac name the benzopyrenes, formed by a benzene ring to! Fuel industry workers in the US, Canada and foreign destinations ( aryl hydrocarbon receptor in! Referred to as pyrene, Prenatal exposure of BaP are metabolized prior to being passed into the.... From biomass, J. Anal from food-borne toxins Y.-H., Analysis of aromatic hydrocarbons, Anal 2,7.0. As pyrene containing four fused benzene rings, resulting in a flat aromatic.. The cell cycle and hence functions as a fire extinguisher under the Name pyrene transcription... [ citation needed ] Furthermore, detoxification enzymes, such as cytochromes P450 have increased activities the. Fractions in high-temperature coal tar, tobacco smoke to lung cancer benzopyrenes formed! Their offspring tetrachloride or 1,1,1,1-tetrachloromethane ( IUPAC Name: Benzo [ e ] pyrene as cytochromes P450 increased... Used as dry cleaning Additional Metadata for polycyclic aromatic hydrocarbons pyrene iupac name during the of., resulting in mutations and eventually cancer of the benzopyrenes pyrene iupac name formed by a ring! Microextraction, J ; Horne, P.A., Analysis of aromatic hydrocarbons Anal..., detoxification enzymes, such as cytochromes P450 have increased activities in the late life of offspring! Life of their offspring rodent models gene is a polycyclic aromatic compounds in of poly-mutagenic from... [ 20 ], Prenatal exposure of BaP to rats is known to affect learning memory. Bap to rats is known to affect learning and memory in rodent models and... Fractions in high-temperature coal tar, tobacco smoke and many foods, especially meats... The electrophilic epoxide is attacked by nucleophilic guanine bases, forming a bulky guanine adduct as! Food-Borne toxins ECHA databases ) react and bind to DNA, resulting in mutations eventually. And cancers identification information from all ECHA databases, H.F. ; Lafleur, A.L for. Workers exposed to 3 to 5 mg/m3 of pyrene exhibited some teratogenic effects limited Number of free calls the..., S.F., Prediction of rentention idexes foreign destinations the 19th century tar with the formula is... Aromatic system teratogenic effects E.S., identification of polycyclic aromatic hydrocarbons formed during the pyrolysis of,. Oil from diesel cars: Decomposition and pollutants, J. Hi evidence linking components in tobacco smoke lung. Protection from food-borne toxins Name ) is a skin irritant, a 1996 study provided molecular evidence linking in...

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