58917-67-2

Usage

Uses

Used in Research Applications:
+-7R,8T-DIHYDROXY-9T,-10T-EPOXY-7,8,9,10-TETRAHYDROBENZO(A) is used as a research tool to study the mechanisms of carcinogenesis and the effects of environmental pollutants on human health. It is used to investigate the role of p53 and JNK mediated pathways in inducing an inflammatory response in normal human lung fibroblasts.
Used in Toxicology Studies:
+-7R,8T-DIHYDROXY-9T,-10T-EPOXY-7,8,9,10-TETRAHYDROBENZO(A) is used in toxicology studies to evaluate the potential health risks associated with exposure to environmental pollutants and tobacco smoke. It helps researchers understand the molecular mechanisms underlying the development of esophageal cancer and other malignancies.
Used in Drug Development:
+-7R,8T-DIHYDROXY-9T,-10T-EPOXY-7,8,9,10-TETRAHYDROBENZO(A) is used in drug development to identify potential therapeutic agents that can counteract the harmful effects of this carcinogen. It serves as a target for the development of drugs that can inhibit the formation of BPDE-DNA adducts and reduce the risk of cancer.
Used in Environmental Monitoring:
+-7R,8T-DIHYDROXY-9T,-10T-EPOXY-7,8,9,10-TETRAHYDROBENZO(A) is used in environmental monitoring to assess the levels of pollution in air, water, and soil. It helps in the development of strategies to reduce exposure to this harmful compound and protect public health.
Used in Public Health Policies:
+-7R,8T-DIHYDROXY-9T,-10T-EPOXY-7,8,9,10-TETRAHYDROBENZO(A) is used in public health policies to raise awareness about the dangers of tobacco smoke and environmental pollution. It serves as a basis for regulations and guidelines aimed at reducing exposure to this carcinogen and improving overall health outcomes.

Safety Profile

Questionable carcinogen withexperimental tumorigenic data reported. Human mutationdata reported. When heated to decomposition it emitsacrid smoke and irritating fumes.

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 

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%.