CAS 58917-67-2

BPDE

Description:

BPDE, or benzo[a]pyrene diol epoxide, is a potent polycyclic aromatic hydrocarbon derivative known for its role as a carcinogen. It is formed from the metabolic activation of benzo[a]pyrene, a compound commonly found in tobacco smoke and grilled foods. BPDE is characterized by its ability to form DNA adducts, which can lead to mutations and ultimately contribute to cancer development. The compound is highly reactive due to the presence of epoxide groups, making it capable of interacting with nucleophilic sites in biological molecules. BPDE is typically studied in the context of environmental health and toxicology, as exposure to this compound can occur through inhalation, ingestion, or dermal contact. Its persistence in the environment and potential for bioaccumulation raise concerns regarding its impact on human health and ecosystems. Understanding the mechanisms of BPDE's action is crucial for assessing risks associated with exposure and for developing strategies to mitigate its effects.

Formula: C₂₀H₁₄O₃

InChI: InChI=1/C20H14O3/c21-17-13-8-11-5-4-9-2-1-3-10-6-7-12(15(11)14(9)10)16(13)19-20(23-19)18(17)22/h1-8,17-22H/t17-,18+,19-,20+/s2

InChI key: InChIKey=DQEPMTIXHXSFOR-LMWGHQENNA-N

SMILES: O[C@@H]1C2=C(C3=C4C=5C(C=C3)=CC=CC5C=CC4=C2)[C@@]6([C@@](O6)([C@H]1O)[H])[H]

Synonyms:

• (+)-Anti-7,8-Dihydroxy-9,10-Epoxy-7,8,9,10-Tetrahydrobenzo(A)Pyrene
• (+-)-(E)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene
• (+/-)-Syn-7,8-Dihydroxy-9,10-Epoxy-7,8,9,10-Tetrahydrobenzo(A)Pyrene
• (-)-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene
• (±)-7α,8β-Dihydroxy-9β,10β-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• (±)-7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• (±)-Benzo[a]pyrene-r-7,t-8-dihydrodiol-t-9,10-epoxide
• (±)-anti-7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• (±)-anti-BPDE
• (±)-anti-Benzo[a]pyrene-7,8-dihydro-7,8-diol 9,10-epoxide
• (±)-anti-Benzo[a]pyrene-7,8-diol-9,10-epoxide
• (±)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• (±)-r-7,t-8-Dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• (±)-trans-7,8-Dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• (±)-trans-7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
• 7r,8t-Dihydroxy-9t,10t-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• Benzo(10,11)chryseno(3,4-b)oxirene-7,8-diol, 7,8,8a,9a-tetrahydro-
• Benzo(a)pyrene, 7,8,9,10-tetrahydro-7,8-dihydroxy-9,10-epoxy-, (E)-
• Benzo(a)pyrene, 7,8,9,10-tetrahydro-7,8-dihydroxy-9,10-epoxy-, anti-
• Benzo[10,11]chryseno[3,4-b]oxirene-7,8-diol, 7,8,8a,9a-tetrahydro-, (7R,8S,8aS,9aR)-rel-
• Benzo[10,11]chryseno[3,4-b]oxirene-7,8-diol, 7,8,8a,9a-tetrahydro-, (7α,8β,8aα,9aα)-
• Bpde 2
• anti-(±)-Benzo[a]pyrene-trans-7,8-dihydrodiol-9,10-epoxide

Benzo[a]pyrene Diol Epoxide (>90%)

Controlled Product

CAS: 58917-67-2

Stability Light Sensitive
Applications Benzo[a]pyrene diol epoxide stimulates an inflammatory response in normal human lung fibroblasts through a p53 and JNK mediated pathway. Benzo [a]pyrene diol epoxide (BPDE), a carcinogen present in tobacco smoke as well as in environmental pollution, induces esophageal carcinogenesis.
References Cavalieri, E., et al.: Biochem. Pharmacol., 1988, 37, 2173 (1988); Conney, A., et al.: Cancer Res., 42, 4875 (1982); Penning, T., et al.: Chem. Res. Toxicol., 9, 84 (1996); Lu, D., et al.: Chem. Res. Toxicol., 2011, 24, 1905 (2011);

Formula: C₂₀H₁₄O₃

Purity: >90%

Color and Shape: Neat

Molecular weight: 302.3234

Ref: TR-B287550

Benzo[A]pyrene diol epoxide

CAS: 58917-67-2

Benzo[A]pyrene diol epoxide (BPDE) is a genotoxic compound that can react with DNA, forming covalent adducts. This reaction leads to structural and functional changes in the DNA molecule and can lead to mutations in DNA. BPDE has been detected in human serum as an epoxide-DNA adduct. It is found in cigarette smoke and other sources of air pollution such as automobile exhaust, coal fires, and combustion of wood or fossil fuels. Analysis of BPDE has been used as an analytical method for identifying its presence in environmental samples. Multivariate logistic regression analysis has been used to study the relationship between BPDE levels and erythrocyte micronuclei frequency in humans. The results showed that there was a statistically significant association between these two variables.

Formula: C₂₀H₁₄O₃

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 302.3 g/mol

Ref: 3D-ICA91767