Benzo(a)piren

Benzo[a]piren
	Benzo[a]piren
Identifikacija
CAS registarski broj	50-32-8
ChemSpider	2246
KEGG	C07535
ChEBI	29865
ChEMBL	CHEMBL31184
Jmol-3D slike	Slika 1
SMILES
	c1ccc2c(c1)cc3ccc4cccc5c4c3c2cc5
InChI
	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 ; Kod: FMMWHPNWAFZXNH-UHFFFAOYSA-N 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; Kod: FMMWHPNWAFZXNH-UHFFFAOYAQ
Svojstva
Molekulska formula	C20H12
Molarna masa	252.31 g mol−1
Gustina	1,24 g/cm³ (25 °C)
Tačka topljenja	179 °C
Tačka ključanja	495 °C
Rastvorljivost u vodi	0,11 mg/L (25 °C)
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Benzo[a]piren je policiklični aromatični ugljovodonik koji se nalazi u katranu, i ima hemijsku formulu C₂₀H₁₂. Njegovi metaboliti su mutageni i visoko karcinogeni. On je uvršten u grupu 1 karcinogena IARC-a. Ovo jedinjenje pripada klasi benzopirena. Ono se sastoji od benzenovog prstena kondenzovanog sa pirenom. Benzo[a]pyren je rezultat nepotpunog sagorevanja na temperaturi između 300 °C i 600 °C.

Dimnjičari su obolevali od raka testisa u 18. veku, i česta pojava raka kože je zabeležena među industrijskim radnicima u 19. veku. Utvrđeno je da je benzo[a]piren jedinjenje odgovorno za ove slučajeve 1933. Njegova toksičnost je demonstrirana putem razvoja tumora kože na laboratorijskim životinjama. Kad telo pokuša da metabolizuje benzo[a]piren, rezultirajući diol epoksid reaguje i vezuje se za DNK, proizvodeći mutacije i eventualno kancer.

Izvori benzo[a]pirena

Benzo[a]piren se nalazi u katranu, u automobilskim izduvnim gasovima (posebno iz dizel mašina), u dimu proizvedenom sagorevanjem organskog materijala (poput dima cigareta), i u hrani sa roštilja. Kuvani proizvodi od mesa, regularno konzumiranje kojih je epidemiološki povezano sa povišenim nivoima raka debelog creva^[4] (mada to samo po sebi ne dokazuje karcinogenost),^[5] sadrže do 4 ng/g benzo[a]pirena,^[6] do 5.5 ng/g je prisutno u prženoj piletini^[7] i 62.6 ng/g u govedini prepečenoj na žaru.^[8]

Reference

↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Le Marchand L, Hankin JH, Pierce LM, Sinha R, Nerurkar PV, Franke AA, Wilkens LR, Kolonel LN, Donlon T, Seifried A, Custer LJ, Lum-Jones A, Chang W. Well-done red meat, metabolic phenotypes and colorectal cancer in Hawaii. Mutation Research. 2002 Sep 30;506-507:205-14. PMID 12351160
↑ Truswell AS. Meat consumption and cancer of the large bowel. European Journal of Clinical Nutrition. 2002 Mar;56 Suppl 1:S19-24. PMID 11965518
↑ Kazerouni N, Sinha R, Hsu CH, Greenberg A, Rothman N. Analysis of 200 food items for benzo[a]pyrene and estimation of its intake in an epidemiologic study. Food and Chemical Toxicology 2002;40(1):133. doi:10.1016/S0278-6915(00)00158-7
↑ Lee BM, Shim GA. Dietary exposure estimation of benzo[a]pyrene and cancer risk assessment. Journal of Toxicology and Environmental Health Part A. 2007 Aug;70(15-16):1391-4. PMID 17654259
↑ Aygün SF, Kabadayi F. Determination of benzo[a]pyrene in charcoal grilled meat samples by HPLC with fluorescence detection. International Journal of Food Sciences and Nutrition. 2005 Dec;56(8):581-5. PMID 16638662

Povezano

Spoljašnje veze

Portal Hemija

Internacionalna karta hemijske bezbednosti 0104
National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet Arhivirano 2006-05-18 na Wayback Machine-u
„Lung cancer as consequence by Benzopyrene in smokers”. Lung Cancer. Arhivirano iz originala na datum 2005-04-14. Pristupljeno 16 maj, 2012.
„Levels of Benzopyrene in Burnt toasts”. Guardian Unlimited. Pristupljeno 16 maj, 2012.
„Crystal and molecular structure of a benzo-a-pyrene 7,8-diol 9,10-epoxide N2-deoxyguanosine adduct: Absolute configuration and conformation”. Proceedings of the National Academy of Sciences. Pristupljeno 16 maj, 2012.

[1] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[2] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[3] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[4] Le Marchand L, Hankin JH, Pierce LM, Sinha R, Nerurkar PV, Franke AA, Wilkens LR, Kolonel LN, Donlon T, Seifried A, Custer LJ, Lum-Jones A, Chang W. Well-done red meat, metabolic phenotypes and colorectal cancer in Hawaii. Mutation Research. 2002 Sep 30;506-507:205-14. PMID 12351160

[5] Truswell AS. Meat consumption and cancer of the large bowel. European Journal of Clinical Nutrition. 2002 Mar;56 Suppl 1:S19-24. PMID 11965518

[6] Kazerouni N, Sinha R, Hsu CH, Greenberg A, Rothman N. Analysis of 200 food items for benzo[a]pyrene and estimation of its intake in an epidemiologic study. Food and Chemical Toxicology 2002;40(1):133. doi:10.1016/S0278-6915(00)00158-7

[7] Lee BM, Shim GA. Dietary exposure estimation of benzo[a]pyrene and cancer risk assessment. Journal of Toxicology and Environmental Health Part A. 2007 Aug;70(15-16):1391-4. PMID 17654259

[8] Aygün SF, Kabadayi F. Determination of benzo[a]pyrene in charcoal grilled meat samples by HPLC with fluorescence detection. International Journal of Food Sciences and Nutrition. 2005 Dec;56(8):581-5. PMID 16638662

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]