Dibenzopyrenes are a group of high molecular weight polycyclic aromatic hydrocarbons with the molecular formula C24H14. There are five isomers of dibenzopyrene which differ by the arrangement of aromatic rings: dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, dibenzo[a,l]pyrene, and dibenzo[e,l]pyrene.
Dibenzopyrenes have been recognized for their suspected human carcinogenicity.[1] The most notable dibenzopyrene isomer, dibenzo[a,l]pyrene is a constituent of tobacco smoke[2] and is thought to be 30 to 100 times more potent as a carcinogen than benzo[a]pyrene.[3][4] The four dibenzopyrene isomers; dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, dibenzo[a,l]pyrene are included in the list of 16 EU priority polycyclic aromatic hydrocarbons due to their mutagenicity and suspected human carcinogenicity.
Primary sources of dibenzopyrenes in the environment are combustion of wood and coal,[5] gasoline and diesel exhaust,[6] and tires.[7]
ReferencesEdit
^Boström, C. E.; Gerde, P; Hanberg, A; Jernström, B; Johansson, C; Kyrklund, T; Rannug, A; Törnqvist, M; Victorin, K; Westerholm, R (2002). "Cancer risk assessment, indicators, and guidelines for polycyclic aromatic hydrocarbons in the ambient air". Environmental Health Perspectives. 110 Suppl 3: 451–88. doi:10.1289/ehp.110-1241197. PMC1241197. PMID 12060843.
^Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC3084482. PMID 21556207.
^"Development of a Relative Potency Factor (RPF) Approach for Polycyclic Aromatic Hydrocarbon (PAH) Mixtures". Integrated Risk Information System (IRIS). United States Environmental Protection Agency. 2010.
^Muller, Pavel (1997). "Scientific criteria document for multimedia standards development, polycyclic aromatic hydrocarbons (PAH)". Standards Development Branch, Ontario Ministry of Environment and Energy. {{cite journal}}: Cite journal requires |journal= (help)
^Masala, Silvia; Bergvall, Christoffer; Westerholm, Roger (15 August 2012). "Determination of benzo[a]pyrene and dibenzopyrenes in a Chinese coal fly ash certified reference material". Science of the Total Environment. 432: 97–102. Bibcode:2012ScTEn.432...97M. doi:10.1016/j.scitotenv.2012.05.081. PMID 22728296.
^Bergvall, Christoffer; Westerholm, Roger (2009). "Determination of highly carcinogenic dibenzopyrene isomers in particulate emissions from two diesel- and two gasoline-fuelled light-duty vehicles". Atmospheric Environment. 43 (25): 3883–3890. Bibcode:2009AtmEn..43.3883B. doi:10.1016/j.atmosenv.2009.04.055.
^Sadiktsis, Ioannis; Bergvall, Christoffer; Johansson, Christer; Westerholm, Roger (2012). "Automobile Tires—A Potential Source of Highly Carcinogenic Dibenzopyrenes to the Environment". Environmental Science & Technology. 46 (6): 3326–3334. Bibcode:2012EnST...46.3326S. doi:10.1021/es204257d. PMID 22352997.
August 31, 2023
dibenzopyrenes, group, high, molecular, weight, polycyclic, aromatic, hydrocarbons, with, molecular, formula, c24h14, there, five, isomers, dibenzopyrene, which, differ, arrangement, aromatic, rings, dibenzo, pyrene, dibenzo, pyrene, dibenzo, pyrene, dibenzo, . Dibenzopyrenes are a group of high molecular weight polycyclic aromatic hydrocarbons with the molecular formula C24H14 There are five isomers of dibenzopyrene which differ by the arrangement of aromatic rings dibenzo a e pyrene dibenzo a h pyrene dibenzo a i pyrene dibenzo a l pyrene and dibenzo e l pyrene Dibenzopyrenes dibenzo a e pyrene dibenzo a h pyrenedibenzo a i pyrene dibenzo a l pyrenedibenzo e l pyreneIdentifiersCAS Number 192 65 4 a e Y189 64 0 a h Y189 55 9 a i Y191 30 0 a l Y192 51 8 e l Y3D model JSmol a e Interactive image a h Interactive image a i Interactive image a l Interactive image e l Interactive imageChEBI CHEBI 82442 a e CHEBI 82313 a h CHEBI 82314 a i CHEBI 35861 a l CHEBI 82443 e l ChemSpider 8772 a e 8754 a h 8752 a i 8765 a l 8768 e l PubChem CID 9126 a e 9108 a h 9106 a i 9119 a l 9122 e l UNII SAC8PEK62H a e YXR5R3V8BJK a h Y7FMI112D18 a i YG3X629VE4A a l YR1OAU0KNG7 e l YInChI a e InChI 1S C24H14 c1 2 8 17 16 6 1 14 22 19 10 4 3 9 18 19 20 11 5 7 15 12 13 21 17 24 22 23 15 20 h1 14HKey KGHMWBNEMFNJFZ UHFFFAOYSA N a h InChI 1S C24H14 c1 3 7 19 15 5 1 13 17 9 12 22 20 8 4 2 6 16 20 14 18 10 11 21 19 23 17 24 18 22 h1 14HKey RXUSYFJGDZFVND UHFFFAOYSA N a i InChI 1S C24H14 c1 3 7 19 15 5 1 13 17 9 10 18 14 16 6 2 4 8 20 16 22 12 11 21 19 23 17 24 18 22 h1 14HKey TUGYIJVAYAHHHM UHFFFAOYSA N a l InChI 1S C24H14 c1 2 8 18 16 6 1 14 17 13 12 15 7 5 11 20 19 9 3 4 10 21 19 24 18 23 17 22 15 20 h1 14HKey JNTHRSHGARDABO UHFFFAOYSA N e l InChI 1S C24H14 c1 2 8 16 15 7 1 19 11 5 13 21 17 9 3 4 10 18 17 22 14 6 12 20 16 24 22 23 19 21 h1 14HKey BMIAHKYKCHRGBA UHFFFAOYSA NSMILES a e c1ccc2c c1 cc3c4ccccc4c5cccc6c5c3c2cc6 a h c1ccc2c c1 cc3ccc4c5ccccc5cc6c4c3c2cc6 a i c1ccc2c c1 cc3ccc4cc5ccccc5c6c4c3c2cc6 a l c1ccc2c c1 cc3ccc4cccc5c4c3c2c6c5cccc6 e l c1ccc2c c1 c3cccc4c3c5c2cccc5c6c4cccc6PropertiesChemical formula C 24H 14Molar mass 302 376 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Dibenzopyrenes have been recognized for their suspected human carcinogenicity 1 The most notable dibenzopyrene isomer dibenzo a l pyrene is a constituent of tobacco smoke 2 and is thought to be 30 to 100 times more potent as a carcinogen than benzo a pyrene 3 4 The four dibenzopyrene isomers dibenzo a e pyrene dibenzo a h pyrene dibenzo a i pyrene dibenzo a l pyrene are included in the list of 16 EU priority polycyclic aromatic hydrocarbons due to their mutagenicity and suspected human carcinogenicity Primary sources of dibenzopyrenes in the environment are combustion of wood and coal 5 gasoline and diesel exhaust 6 and tires 7 References Edit Bostrom C E Gerde P Hanberg A Jernstrom B Johansson C Kyrklund T Rannug A Tornqvist M Victorin K Westerholm R 2002 Cancer risk assessment indicators and guidelines for polycyclic aromatic hydrocarbons in the ambient air Environmental Health Perspectives 110 Suppl 3 451 88 doi 10 1289 ehp 110 1241197 PMC 1241197 PMID 12060843 Talhout Reinskje Schulz Thomas Florek Ewa Van Benthem Jan Wester Piet Opperhuizen Antoon 2011 Hazardous Compounds in Tobacco Smoke International Journal of Environmental Research and Public Health 8 12 613 628 doi 10 3390 ijerph8020613 ISSN 1660 4601 PMC 3084482 PMID 21556207 Development of a Relative Potency Factor RPF Approach for Polycyclic Aromatic Hydrocarbon PAH Mixtures Integrated Risk Information System IRIS United States Environmental Protection Agency 2010 Muller Pavel 1997 Scientific criteria document for multimedia standards development polycyclic aromatic hydrocarbons PAH Standards Development Branch Ontario Ministry of Environment and Energy a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help Masala Silvia Bergvall Christoffer Westerholm Roger 15 August 2012 Determination of benzo a pyrene and dibenzopyrenes in a Chinese coal fly ash certified reference material Science of the Total Environment 432 97 102 Bibcode 2012ScTEn 432 97M doi 10 1016 j scitotenv 2012 05 081 PMID 22728296 Bergvall Christoffer Westerholm Roger 2009 Determination of highly carcinogenic dibenzopyrene isomers in particulate emissions from two diesel and two gasoline fuelled light duty vehicles Atmospheric Environment 43 25 3883 3890 Bibcode 2009AtmEn 43 3883B doi 10 1016 j atmosenv 2009 04 055 Sadiktsis Ioannis Bergvall Christoffer Johansson Christer Westerholm Roger 2012 Automobile Tires A Potential Source of Highly Carcinogenic Dibenzopyrenes to the Environment Environmental Science amp Technology 46 6 3326 3334 Bibcode 2012EnST 46 3326S doi 10 1021 es204257d PMID 22352997 Retrieved from https en wikipedia org w index php title Dibenzopyrenes amp oldid 1134772227, wikipedia, wiki, book, books, library,
