63323-31-9

Basic information

• Product Name: Diolepoxide 2
• Synonyms: (+)-(R,S,S,R)-Benzo[a]pyrene diol epoxide;(7R,8S,8aS,9aR)-7,8,8a,9a-Tetrahydrobenzo[10,11]chryseno[3,4-b]oxirene-7,8-diol;(7R,8S,9S,10R)-7,8,9,10-Tetrahydro-7,8-dihydroxy-9,10-epoxybenzo[a]pyrene;Diolepoxide 2
• CAS NO: 63323-31-9
• Molecular Formula: C₂₀H₁₄O₃
• Molecular Weight: 302.34
• Mol File: 63323-31-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 227°C (rough estimate)
• Boiling Point: 383.36°C (rough estimate)
• Appearance: /
• Density: 1.2559 (rough estimate)
• Refractive Index: 1.4618 (estimate)
• CAS DataBase Reference: Diolepoxide 2(CAS DataBase Reference)
• NIST Chemistry Reference: Diolepoxide 2(63323-31-9)
• EPA Substance Registry System: Diolepoxide 2(63323-31-9)

Safety Data

• Hazardous Substances Data: 63323-31-9(Hazardous Substances Data)

Usage

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-/m1/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 
• 63268-36-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (7R,8R)-8-hydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-7-yl ester 
• 63268-38-2 7,8-bis-benzoyloxy-7,8-dihydro benzo[a]pyrene 
• 169437-81-4 trans-(7R,8R)-7,8-dibenzoyloxy-7,8,9,10-tetrahydrobenzopyrene 

Downstream Products

• 62624-73-1 C₃₀H₂₇N₅O₇ 
• 128084-00-4 (+/-)-7β,8α,9α-tris(benzoyloxy)-10β-amino-7,8,9,10-tetrahydrobenzopyrene 
• 59957-91-4 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 59957-91-4 7,8,9,10-tetrahydroxytetrahydrobenzo[a]pyrene 
• 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 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%.

Regio- and stereocontrolled synthesis of the bay-region anti-diol epoxide metabolites of the potent carcinogens benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene

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Improved Formal Preparation of Enantiomerically Pure anti-Benzopyrene Diol Epoxide.

We report an improved, economical formal route to enantiomerically pure anti-benzopyrene diol epoxide (BPDE).A trimethylaluminum catalyzed regio- and stereoselective opening of racemic 7,8-epoxy-7,8,9,10-tetrahydrobenzopyrene with Mosher's acid delivers benzylic esters exclusively.This step is a significant improvement over the lack of regioselectivity of standard procedures.We also show that modification of the subsequent chemical steps further shortens the preparation of enantiomerically pure anti-BPDE.