58917-91-2

Usage

Uses

Used in Environmental Research:
SYN-BENZO(A)PYRENEDIOLEPOXIDE is used as a research compound for studying the impact of environmental pollutants and carcinogens on human and rodent health. Its role as an intermediate in the synthesis of these harmful substances makes it a valuable tool for understanding their metabolic pathways and potential health risks.
Used in Pharmaceutical Development:
SYN-BENZO(A)PYRENEDIOLEPOXIDE is used as a key intermediate in the development of pharmaceuticals targeting the detoxification and treatment of diseases caused by exposure to environmental pollutants and carcinogens. Its involvement in metabolic studies aids in the design of drugs that can mitigate the harmful effects of these substances on the human body.
Used in Toxicology Studies:
SYN-BENZO(A)PYRENEDIOLEPOXIDE is employed as a reference compound in toxicology studies, helping researchers to evaluate the toxicity levels and potential health hazards associated with exposure to environmental pollutants and carcinogens. This information is crucial for developing safety guidelines and regulations to protect public 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/t17-,18+,19-,20+/m0/s1

Upstream product

• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 115237-06-4 (((2-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene 
• 1714-29-0 1-bromopyrene 
• 156641-98-4 (6-methoxy-2-naphthalene)boronic acid 
• 17573-31-8 3-methoxybenzopyrene 
• 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 
• 172533-57-2 Toluene-4-sulfonic acid 2-bromo-pyren-1-yl ester 

Downstream Products

• 62697-13-6 (+/-)-7β,8α,9β,10β-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 77340-98-8 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-((7S,8R,9R,10S)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1,9-dihydro-purin-6-one 
• 77340-97-7 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-((7R,8S,9S,10S)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1,9-dihydro-purin-6-one 
• 77341-00-5 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-((7S,8R,9R,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1,9-dihydro-purin-6-one 
• 77341-01-6 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-((7R,8S,9S,10R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1,9-dihydro-purin-6-one 
• 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 
• 62697-17-0 r-7,t-8,10,c-9-tetrahydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 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 

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%.