57404-88-3

Basic information

• Product Name: TRANS-7,8-DIHYDROXY-7,8-DIHYDRO-BENZO(A)PYRENE
• Synonyms: TRANS-7,8-DIHYDROXY-7,8-DIHYDRO-BENZO(A)PYRENE
• CAS NO: 57404-88-3
• Molecular Formula: C20H14 O2
• Molecular Weight: 286.34
• Product Categories: Aromatics, Heterocycles, Mutagenesis Research Chemicals
• Mol File: 57404-88-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 388.69°C (rough estimate)
• Flash Point: 268.6°C
• Appearance: /
• Density: 1.1197 (rough estimate)
• Vapor Pressure: 4.47E-13mmHg at 25°C
• Refractive Index: 1.7580 (estimate)
• CAS DataBase Reference: TRANS-7,8-DIHYDROXY-7,8-DIHYDRO-BENZO(A)PYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-7,8-DIHYDROXY-7,8-DIHYDRO-BENZO(A)PYRENE(57404-88-3)
• EPA Substance Registry System: TRANS-7,8-DIHYDROXY-7,8-DIHYDRO-BENZO(A)PYRENE(57404-88-3)

Safety Data

• Hazardous Substances Data: 57404-88-3(Hazardous Substances Data)

Usage

Uses

trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene is a metabolite of Benzopyrene (B205800). Benzo[a]pyrene (B205800), a prototypic PAH, is metabolized by cytochrome P 450 1A1/1B1. (-)-trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene (D452280) undergoes further P 4501A1/1B1-mediated metabolism to a carcinogen, which forms DNA-adducts primarily with 2'-deoxyguanosine. A carcinogen.

InChI:InChI=1/C20H14O2/c21-16-9-7-14-10-13-5-4-11-2-1-3-12-6-8-15(18(13)17(11)12)19(14)20(16)22/h1-10,16,20-22H/t16-,20+/m0/s1

Upstream product

• 156641-98-4 (6-methoxy-2-naphthalene)boronic acid 
• 6751-75-3 2-bromoresorcinol 
• 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 
• 57405-01-3 C₃₄H₂₃BrO₄ 
• 57405-00-2 (+/-)-7,8,9,10-Tetrahydrobenzopyrene-trans-7,8-diol dibenzoate 
• 6272-55-5 7-hydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 17573-15-8 9,10-dihydro benzopyrene 
• 678996-94-6 2-(2,6-bis{2-methoxyvinyl}phenyl)-6-methoxynaphthalene 
• 671780-70-4 2-methoxy-6-(2,6-divinylphenyl)naphthalene 
• 671780-69-1 2-(2-methoxynaphthalen-6-yl)benzene-1,3-dialdehyde 
• 17573-31-8 3-methoxybenzopyrene 
• 13345-26-1 7-hydroxy benzopyrene 

Downstream Products

• 63323-30-8 (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 60864-95-1 (-)-7R-trans-Benzopyrene-7,8-dihydrodiol 
• 62314-67-4 (+/-)-trans-7,8-Dihydrobenzo[a]pyrene-7,8-diol 
• 61490-66-2 7,8,9,10-tetrahydroxytetrahydrobenzopyrene 
• 58917-91-2 (+/-)-7α,8β-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 62697-16-9 (+/-)-7β,8α,9α,10α-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 62697-17-0 r-7,t-8,10,c-9-tetrahydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 62697-13-6 (+/-)-7β,8α,9β,10β-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 37994-82-4 7-Hydroxybenzo[a]pyrene 
• 13345-26-1 7-hydroxy benzopyrene 

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%.

Synthesis of the o-Quinones and Other Oxidized Metabolites of Polycyclic Aromatic Hydrocarbons Implicated in Carcinogenesis

Efficient new syntheses of the o-quinone derivatives of benzo[a]pyrene (BPQ), 7,12-dimethylbenz-[a] anthracene (DMBAQ), and benz[a]anthracene (BAQ), implicated as active carcinogenic metabolites of the parent polycyclic aromatic hydrocarbons (PAHs), are reported. These PAH quinones also serve as starting compounds for the synthesis of the other active metabolites of these PAHs thought to be involved in their mechanism(s) of carcinogenesis. The latter include the corresponding o-catechols, trans-dihydrodiols, and the corresponding anti- and syn-diol epoxides.

Efficient Synthesis of Non-K-Region trans-Dihydro Diols of Polycyclic Aromatic Hydrocarbons from o-Quinones and Catechols

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