Benzo(a)pyrene

Benzo[a]pyrene

Names
IUPAC name Benzo[a]pyrene
Identifiers
CAS Number	50-32-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:29865 Y
ChEMBL	ChEMBL31184 Y
ChemSpider	2246 Y
ECHA InfoCard	100.000.026
KEGG	C07535 Y
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 Y Key: FMMWHPNWAFZXNH-UHFFFAOYSA-N Y 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
SMILES c1ccc2c(c1)cc3ccc4cccc5c4c3c2cc5
Properties
Chemical formula	C20H12
Molar mass	252.32 g·mol−1
Density	1.24 g/cm3 (25 °C)
Melting point	179 °C (354 °F; 452 K)
Boiling point	495 °C (923 °F; 768 K)
Solubility in water	0.2 to 6.2 ug/L
Magnetic susceptibility (χ)	-135.7·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Benzo[a]pyrene is a polycyclic aromatic hydrocarbon and the result of incomplete combustion 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 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 connected to soot.

Benzo[a]pyrene (BaP) is a polycyclic aromatic hydrocarbon found in coal tar with the formula C₂₀H₁₂. 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).

The main source of atmospheric BaP is residential wood burning. It is also found in coal tar, in automobile exhaust fumes (especially from diesel engines), in all smoke resulting from the combustion of organic material (including cigarette smoke), and in charbroiled food. A 2001 National Cancer Institute study found levels of BaP to be significantly higher in foods that were cooked well-done on the barbecue, particularly steaks, chicken with skin, and hamburgers: Cooked meat products have been shown to contain up to 4 ng/g of BaP, and up to 5.5 ng/g in fried chicken and 62.6 ng/g in overcooked charcoal barbecued beef.