Benzo(a)pyrene

Benzo[a]pyrene
Benzo[a]pyrene


Names
Preferred IUPAC name
Benzo[pqr]tetraphene[1]
Other names
  • Benz[a]pyrene
  • Benzo[a]pyrene
  • 3,4-Benzpyrene
  • 3,4-Benzopyrene
  • 3,4-Benz[a]pyrene
  • 3,4-Benzo[a]pyrene
  • Pentacyclo[10.6.2.02,7.09,19.016,20]icosa-1,3,5,7,9,11,13,15,17,19-decaene[citation needed]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.026 Edit this at Wikidata
EC Number
  • 200-028-5
KEGG
RTECS number
  • DJ3675000
UNII
UN number 3077, 3082
  • 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 checkY
    Key: FMMWHPNWAFZXNH-UHFFFAOYSA-N checkY
  • 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
    Key: FMMWHPNWAFZXNH-UHFFFAOYAQ
  • c1ccc2c(c1)cc3ccc4cccc5c4c3c2cc5
Properties
C20H12
Molar mass 252.316 g·mol−1
Density 1.24 g/cm3 (25 °C)
Melting point 179[2] °C (354 °F; 452 K)
Boiling point 495 °C (923 °F; 768 K)
0.2 to 6.2 μg/L
-135.7·10−6 cm3/mol
Hazards[3]
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H317, H340, H350, H360, H410
P201, P202, P261, P272, P273, P280, P281, P302+P352, P308+P313, P321, P333+P313, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Benzo[a]pyrene (BaP or B[a]P) 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). The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C20H12 is one of the benzopyrenes, 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 Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already known to be connected to soot.

  1. ^ Henri A. Favre, Warren H. Powell (2013). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. Royal Society of Chemistry. p. 232. ISBN 978-0-85404-182-4.
  2. ^ William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–42. ISBN 978-1-4987-5429-3.
  3. ^ "benzo[a]pyrene". pubchem.ncbi.nlm.nih.gov.