55097-80-8

Usage

Uses

Used in Environmental and Health Research:
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide is used as a subject of research in environmental and health studies to understand its role in the carcinogenic properties of pollutants and to explore ways to mitigate its impact on human health.
Used in Toxicology and Mutagenesis Studies:
BPDE is utilized as a model compound in toxicology and mutagenesis research to investigate the mechanisms of DNA damage and tumor induction, as well as to develop strategies for cancer prevention and treatment.
Used in Analytical Chemistry:
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide is employed as a reference compound in analytical chemistry for the development and validation of methods to detect and quantify toxic and carcinogenic compounds in environmental and biological samples.
Used in Drug Development:
BPDE is used in the pharmaceutical industry for the development of drugs and therapies aimed at counteracting its toxic and carcinogenic effects, as well as for the identification of potential chemopreventive agents that can reduce the risk of cancer associated with exposure to BPDE and similar compounds.
Used in Public Health Policy and Regulation:
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide serves as a basis for the establishment of public health policies and regulations to control the levels of toxic and carcinogenic compounds in the environment, including the setting of safety standards and guidelines for exposure limits.
Used in Education and Awareness Programs:
BPDE is incorporated into educational and awareness programs to inform the public about the health risks associated with exposure to environmental pollutants and to promote strategies for reducing exposure and mitigating the impact of these substances on human health.

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

Upstream product

• 156641-98-4 (6-methoxy-2-naphthalene)boronic acid 
• 17573-31-8 3-methoxybenzopyrene 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 65199-11-3 benzo[a]pyren-7,8-dione 
• 6751-75-3 2-bromoresorcinol 
• 13345-26-1 7-hydroxy benzopyrene 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 19821-80-8 1,3-dibromo-2-iodo-benzene 
• 115237-06-4 (((2-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene 
• 172533-57-2 Toluene-4-sulfonic acid 2-bromo-pyren-1-yl ester 
• 1714-29-0 1-bromopyrene 

Downstream Products

• 62624-73-1 C₃₀H₂₇N₅O₇ 
• 59957-91-4 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 59957-91-4 7,8,9,10-tetrahydroxytetrahydrobenzo[a]pyrene 
• 128084-00-4 (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-amino-7,8,9,10-tetrahydrobenzopyrene 
• 59957-91-4 (7R,8S,9R)-7,8,9,10-Tetrahydro-benzo[def]chrysene-7,8,9,10-tetraol 
• 65883-37-6 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-((7R,8S,9R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1H-pyrimidin-2-one 
• 62624-73-1 9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-((7R,8R,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1,9-dihydro-purin-6-one 
• 61490-66-2 7,8,9,10-tetrahydroxytetrahydrobenzopyrene 
• 62697-16-9 (+/-)-7β,8α,9α,10α-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 136616-47-2 (S)-2-[((S)-1-{(S)-2-Amino-3-[1-(7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-yl)-1H-imidazol-4-yl]-propionyl}-pyrrolidine-2-carbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid 
• 136616-46-1 (S)-2-[((S)-1-{(S)-2-Amino-3-[3-(7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-yl)-3H-imidazol-4-yl]-propionyl}-pyrrolidine-2-carbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid 

Relevant academic research and scientific papers

Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene

Polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BaP), are ubiquitous environmental contaminants that are implicated in causing lung cancer. BaP is a component of tobacco smoke that is transformed enzymatically to active forms that interact with DNA. We reported previously development of a sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the complete set of its 13C4-labelled oxidized metabolites needed as internal standards They include the metabolites not involved in carcinogenesis (Group A) and the metabolites implicated in initiation of cancer (Group B). The synthetic approach is novel, entailing use of Pd-catalyzed Suzuki, Sonogashira, and Hartwig cross-coupling reactions combined with PtCl2-catalyzed cyclization of acetylenic compounds. This synthetic method requires fewer steps, employs milder conditions, and product isolation is simpler than conventional methods of PAH synthesis. The syntheses of 13C4-BaP and 13C4-BaP-8-ol each require only four steps, and the 13C-atoms are all introduced in a single step. 13C4-BaP-8-ol serves as the synthetic precursor of all the oxidized metabolites of 13C-BaP implicated in initiation of cancer. The isotopic purities of the synthetic 13C 4-BaP metabolites were estimated to be ≥99.9%.