trans-4,5-Dihydrobenzo(a)pyrene-4,5-diol

Base Information

• Chemical Name: trans-4,5-Dihydrobenzo(a)pyrene-4,5-diol
• CAS No.: 37571-88-3
• Molecular Formula: C20H14O2
• Molecular Weight: 286.34
• DSSTox Substance ID: DTXSID001031991
• Nikkaji Number: J238.316K
• Mol file: 37571-88-3.mol

Synonyms:37571-88-3;trans-4,5-Dihydrobenzo(a)pyrene-4,5-diol;trans-Benzo(a)pyrene-4,5-dihydrodiol;(4R,5R)-4,5-dihydrobenzo[a]pyrene-4,5-diol;Benzo(a)pyrene-4,5-dihydrodiol, (E)-;trans-4,5-Dihydro-4,5-dihydroxybenzo(a)pyrene;trans-4,5-Dihydroxy-4,5-dihydrobenzo(a)pyrene;BENZO(a)PYRENE, 4,5-DIHYDRO-4,5-DIHYDROXY-, (E)-;Benzo[a]pyrene-4,5-diol, 4,5-dihydro-, trans-;SCHEMBL3346047;DTXSID001031991;LS-39956;(4R,5R)-benzo[a]pyrene-trans-4,5-dihydrodiol;(4S,5S)-4,5-dihydrobenzo[pqr]tetraphene-4,5-diol

Chemical Property of trans-4,5-Dihydrobenzo(a)pyrene-4,5-diol

Chemical Property:

• Vapor Pressure: 1.09E-13mmHg at 25°C
• Melting Point: 210 °C(Solv: chloroform (67-66-3))
• Refractive Index: 1.7580 (estimate)
• Boiling Point: 566.9°Cat760mmHg
• PKA: 13.53±0.40(Predicted)
• Flash Point: 275.5°C
• PSA: 40.46000
• Density: 1.452g/cm³
• LogP: 4.22660
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 286.099379685
• Heavy Atom Count: 22
• Complexity: 435

Purity/Quality:

99% ^*data from raw suppliers

trans-Benzo[a]pyrene-4,5-dihydrodiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C3=C4C(=CC2=C1)C(C(C5=CC=CC(=C54)C=C3)O)O
• Isomeric SMILES: C1=CC=C2C3=C4C(=CC2=C1)[C@H]([C@@H](C5=CC=CC(=C54)C=C3)O)O
• Uses: trans-Benzo[a]pyrene-4,5-dihydrodiol is a polyaromatic hydrocarbon (PAH) that occurs as an environmental pollutant and is also a suspected carcinogen to humans. When PAHs enter into the body, is converted to a proximate carcinogen by human epoxide hydrolase and CYP1A1, thus initiating cancer.

Technology Process of trans-4,5-Dihydrobenzo(a)pyrene-4,5-diol

There total 5 articles about trans-4,5-Dihydrobenzo(a)pyrene-4,5-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<α>pyrene-4,5-dione (42286-46-4) → 4,5-dihydrobenzopyrene-4,5-trans-(e,e)-diol (28622-84-6,37571-88-3,50700-50-0,51689-89-5,62600-10-6,64474-18-6,72040-28-9,72040-29-0,72040-30-3)

Guidance literature:

With sodium tetrahydroborate; oxygen; In ethanol; for 24h; Ambient temperature;

DOI:10.1055/s-1982-29834

Reference yield:

4,5-dihydro(epoxy) benzopyrene (37574-47-3,72010-12-9,72010-13-0) → 5-hydroxy-benzo[a]pyrene (24027-84-7) + 4-hydroxybenzoanthracene (37574-48-4) + 4,5-dihydrobenzopyrene-4,5-trans-(e,e)-diol (28622-84-6,37571-88-3,50700-50-0,51689-89-5,62600-10-6,64474-18-6,72040-28-9,72040-29-0,72040-30-3)

Guidance literature:

With ethylenediaminetetraacetic acid; tris hydrochloride; In sodium hydroxide; at 23 ℃; pH=7.3; Kinetics;

DOI:10.1021/tx960134j

Reference yield:

4,5-dihydro(epoxy) benzopyrene (37574-47-3,72010-12-9,72010-13-0) + calf thymus desoxyribonucleic acid → 5-hydroxy-benzo[a]pyrene (24027-84-7) + 4-hydroxybenzoanthracene (37574-48-4) + 4,5-dihydrobenzopyrene-4,5-trans-(e,e)-diol (28622-84-6,37571-88-3,50700-50-0,51689-89-5,62600-10-6,64474-18-6,72040-28-9,72040-29-0,72040-30-3) + 2-(4-Hydroxy-4,5-dihydro-benzo[def]chrysen-5-ylamino)-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one

Guidance literature:

With sodium hydroxide; ethylenediaminetetraacetic acid; tris hydrochloride; at 23 ℃; pH=7.3; Kinetics;

DOI:10.1021/tx960134j

upstream raw materials:

4,5-dihydro(epoxy) benzopyrene

benzo<α>pyrene-4,5-dione

Refernces

• 1、 Huang, Chao-Ran,Milliman, Ann,Price, Harry L.,Urano, Shigeyuki,Fetzer, Sharon M.,LeBreton, Pierre R.. "Photoemission probes of catalysis of benzo[a]pyrene epoxide reactions in complexes with linear, double-stranded and closed-circular, single-stranded DNA". . p. 7794 - 7805. Retrieved 2007/10/02.
• 2、 Platt, Karl L.,Oesch, Franz. "K-Region trans-Dihydrodiols of Polycyclic Arenes; An Efficient and Convenient Preparation from o-Quinones or o-Diphenols by Reduction with Sodium Borohydride in the Presence of Oxygen". . p. 459 - 461. Retrieved 2007/10/02.