63323-29-5

Basic information

• Product Name: (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol
• Synonyms: (+)-7,8,9,10-Tetrahydro-9α,10α-epoxybenzo[a]pyrene-7α,8β-diol;(7S,8R,8aS,9aR)-7,8,8a,9a-Tetrahydrobenzo[10,11]chryseno[3,4-b]oxirene-7,8-diol;(7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol;7,8,8aβ,9aβ-Tetrahydrobenzo[10,11]chryseno[3,4-b]oxirene-7α,8β-diol;9α,10α-Epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene-7α,8β-diol
• CAS NO: 63323-29-5
• Molecular Formula: C20H14O3
• Molecular Weight: 302.34
• Mol File: 63323-29-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 403.36°C (rough estimate)
• Flash Point: 313.2°C
• Appearance: /
• Density: 1.1653 (rough estimate)
• Vapor Pressure: 5.73E-15mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• CAS DataBase Reference: (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol(63323-29-5)
• EPA Substance Registry System: (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol(63323-29-5)

Safety Data

• Hazardous Substances Data: 63323-29-5(Hazardous Substances Data)

Usage

Description

(7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol is a complex chemical compound that is a diol derivative of benzo[a]pyrene, a polycyclic aromatic hydrocarbon with known carcinogenic properties. (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol is characterized by its unique stereochemistry, with specific S and R designations indicating the orientation of functional groups on the carbon atoms.

Uses

Used in Research and Development:
(7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol is used as a research compound for studying the mechanisms of carcinogenesis and the potential health effects of exposure to polycyclic aromatic hydrocarbons. Its unique structure and properties make it a valuable tool for understanding the interactions between these compounds and biological systems.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol may be used as a starting material or a reference compound for the development of new drugs targeting cancer or other diseases related to the exposure to polycyclic aromatic hydrocarbons. Its specific stereochemistry and functional groups could provide insights into the design of more effective therapeutic agents.
Used in Environmental Monitoring:
(7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol can be employed as a reference compound in environmental monitoring and assessment of the presence of polycyclic aromatic hydrocarbons in air, water, and soil samples. Its unique properties can help in the development of more accurate and sensitive analytical methods for detecting and quantifying these potentially harmful substances.
Used in Toxicology Studies:
In toxicology, (7S,8R,9S,10R)-7,8,9,10-Tetrahydro-9,10-epoxybenzo[a]pyrene-7,8-diol may be used as a test compound to evaluate the toxic effects of polycyclic aromatic hydrocarbons on various biological systems. This can contribute to a better understanding of the risks associated with exposure to these compounds and inform the development of safety guidelines and regulations.

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

• 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

• 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 
• 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 
• 61490-66-2 7,8,9,10-tetrahydroxytetrahydrobenzopyrene 
• 62697-16-9 (+/-)-7β,8α,9α,10α-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 59957-91-4 7,8,9,10-tetrahydroxytetrahydrobenzo[a]pyrene 
• 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 
• 59957-91-4 (7R,8S,9R)-7,8,9,10-Tetrahydro-benzo[def]chrysene-7,8,9,10-tetraol 
• 59957-91-4 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 128084-00-4 (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-amino-7,8,9,10-tetrahydrobenzopyrene 
• 62624-73-1 C₃₀H₂₇N₅O₇ 

Relevant articles and documents

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%.

Free Radical Epoxidation of 7,8-Dihydroxy-7,8-Dihydrobenzopyrene by Hematin and Polyunsaturated Fatty Acid Hydroperoxides

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