Structure via PubChem · Public domain (PubChem)
benzo[a]pyrene
Sign in to saveAlso known as benzo[pqr]tetraphene, BP, 3,4-BP, 3,4-Benzopyrene, 3,4-Benzpyrene, benzo[def]chrysene, (B(a)P), benzo(a)pyrene
'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 and . 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 chimne
Chemical data
- Formula
- C20H12
- Molecular weight
- 252.3 g/mol
- IUPAC name
- benzo[a]pyrene
- SMILES
- C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3
- InChIKey
- FMMWHPNWAFZXNH-UHFFFAOYSA-N
- XLogP
- 6
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
20 papers- Modulatory effects of catechin hydrate on benzo[a]pyrene-induced nephrotoxicity in adult male albino rats.Toxicology research · 2021
- Some outcomes and a hypothetical mechanism of combined lead and benzo(a)pyrene intoxication, and its alleviation with a complex of bioprotectors.Toxicology reports · 2020
- New insights into benzo[⍺]pyrene osteotoxicity in zebrafish.Ecotoxicology and environmental safety · 2021
- [Malignant transformation of human bronchial epithelial cells induced by benzo(a)pyrene metabolite dihydroxyepoxy benzo pyrene].Wei sheng yan jiu = Journal of hygiene research · 2001
- [Cloning of differentially expressed cDNA sequences involved in malignant transformation induced by benzo(a)pyrene metabolite dihydroxyepoxy benzo pyrene].Zhonghua zhong liu za zhi [Chinese journal of oncology] · 2002
via PubMed
Wikidata facts
- Subclass of
- polycyclic aromatic hydrocarbons
- Has part
- carbon
- Mass
- 252.094
Show 6 more facts
- chemical formula
- C₂₀H₁₂
- Commons category
- Benzo(a)pyrene
- canonical SMILES
- C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3
- found in taxon
- Angelica sinensis
- melting point
- 179
- subject has role
- carcinogen
Sources (6)
via Wikidata · CC0
~9 min read
Encyclopedic overview
13 sectionsContents
- Description
- Sources
- History
- Toxicity
- Nervous system
- Immune system
- Reproductive system
- Carcinogenicity
- Interaction with DNA
- Nucleotide excision repair
- See also
- References
- External links
'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 and . 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.
== Description == 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 and .
Excerpted from Wikipedia’s “benzo[a]pyrene” article, available under the CC BY-SA 4.0 licence.