(E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol

Base Information

• Chemical Name: (E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol
• CAS No.: 57404-88-3
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.33
• Nikkaji Number: J1.107J
• ChEMBL ID: CHEMBL165048
• Mol file: 57404-88-3.mol

Synonyms:7,8-dihydro 7,8-dihydroxybenzo(a)pyrene;7,8-dihydro-7,8-dihydroxybenzopyrene;7,8-dihydrobenzo(a)pyrene-7,8-diol;7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene;benzo(a)pyrene 7,8-dihydrodiol;benzo(a)pyrene 7,8-dihydrodiol, (7R-trans)-isomer;benzo(a)pyrene 7,8-dihydrodiol, (7S-trans)-isomer;benzo(a)pyrene 7,8-dihydrodiol, (cis)-isomer;benzo(a)pyrene 7,8-dihydrodiol, (trans)-(+-)-isomer;benzo(a)pyrene 7,8-dihydrodiol, (trans)-isomer;benzopyrene-7,8-dihydrodiol;BP-7,8 diol;trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene;trans-benzopyrene 7,8-dihydrodiol

Chemical Property of (E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol

Chemical Property:

• Vapor Pressure: 4.47E-13mmHg at 25°C
• Refractive Index: 1.7580 (estimate)
• Boiling Point: 553.3°Cat760mmHg
• Flash Point: 268.6°C
• PSA: 40.46000
• Density: 1.46g/cm³
• LogP: 4.00510
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 286.099379685
• Heavy Atom Count: 22
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

trans-7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C=CC(C5O)O)C=C2
• Isomeric SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C=C[C@@H]([C@H]5O)O)C=C2
• 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.

Technology Process of (E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol

There total 25 articles about (E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

benzo[a]pyren-7,8-dione (65199-11-3) → (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene (57404-88-3,13345-25-0,60657-25-2,60864-95-1,61443-57-0,62314-67-4,76188-90-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 3h; Ambient temperature;

DOI:10.1021/jo00150a027

Reference yield:

(+/-)-trans-7,8-Dihydrobenzopyrene-7,8-diol dibenzoate (57405-08-0,62654-79-9,63268-37-1,63268-38-2,64912-51-2) → (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene (57404-88-3,13345-25-0,60657-25-2,60864-95-1,61443-57-0,62314-67-4,76188-90-4)

Guidance literature:

With sodium methylate;

Reference yield:

7-hydroxy benzopyrene (13345-26-1) → (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene (57404-88-3,13345-25-0,60657-25-2,60864-95-1,61443-57-0,62314-67-4,76188-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92.2 percent / o-iodoxybenzoic acid / dimethylformamide / 1 h / 20 °C

2: NaBH₄; O₂

With sodium tetrahydroborate; oxygen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In N,N-dimethyl-formamide;

DOI:10.1021/jo030348n

upstream raw materials:

benzo[a]pyren-7,8-dione

(+/-)-trans-7,8-Dihydrobenzopyrene-7,8-diol dibenzoate

benzopyrene

7-hydroxy benzopyrene

Downstream raw materials:

7-Hydroxybenzo[a]pyrene

7-hydroxy benzopyrene

7,8,9,10-tetrahydroxytetrahydrobenzopyrene

(+/-)-7β,8α,9α,10α-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene

Refernces

• 1、 Lakshman, Mahesh K.,Keeler, John C.,Ngassa, Felix N.,Hilmer, John H.,Pradhan, Padmanava,Zajc, Barbara,Thomasson, Kathryn A.. "Highly diastereoselective synthesis of nucleoside adducts from the carcinogenic benzo[a]pyrene diol epoxide and a computational analysis". . p. 68 - 76. Retrieved 2008/04/18.
• 2、 Shimada, Tsutomu,Gillam, Elizabeth M. J.,Oda, Yoshimitsu,Tsumura, Fujiko,Sutter, Thomas R.,Guengerich, F. Peter,Inoue, Kiyoshi. "Metabolism of benzo[a]pyrene to trans-7,8-dihydroxy-7,8- dihydrobenzo[a]pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase". . p. 623 - 629. Retrieved 2007/10/03.