13345-26-1

Basic information

• Product Name: 8-HYDROXYBENZO[A]PYRENE
• Synonyms: 8-HYDROXYBENZO[A]PYRENE;Benzo[a]pyren-8-ol
• CAS NO: 13345-26-1
• Molecular Formula: C20H12O
• Molecular Weight: 268.31
• Mol File: 13345-26-1.mol

Chemical Properties

• Boiling Point: 527.2°Cat760mmHg
• Flash Point: 252.9°C
• Appearance: /
• Density: 1.379g/cm³
• Vapor Pressure: 9.85E-12mmHg at 25°C
• Refractive Index: 1.924
• CAS DataBase Reference: 8-HYDROXYBENZO[A]PYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-HYDROXYBENZO[A]PYRENE(13345-26-1)
• EPA Substance Registry System: 8-HYDROXYBENZO[A]PYRENE(13345-26-1)

Safety Data

• Hazardous Substances Data: 13345-26-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-HYDROXYBENZO[A]PYRENE is used as a pharmaceutical agent for its antiestrogenic activity. It has the potential to modulate estrogen-related signaling pathways, which can be beneficial in the treatment of estrogen-dependent conditions and diseases.
Used in Chemical Synthesis:
8-HYDROXYBENZO[A]PYRENE is used as a synthetic intermediate for the production of Benzo[a]pyrene-7,8-diol (B205840). 8-HYDROXYBENZO[A]PYRENE is an important building block in the synthesis of various complex organic molecules, including those with potential applications in the pharmaceutical, agrochemical, and materials science industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4157, 1981 DOI: 10.1021/jo00334a010

InChI:InChI=1/C20H12O/c21-16-7-9-17-15(11-16)10-14-5-4-12-2-1-3-13-6-8-18(17)20(14)19(12)13/h1-11,21H

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• 17573-31-8 3-methoxybenzopyrene 
• 17573-25-0 9,10-dihydrobenzopyren-8(7H)-one 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 

Downstream Products

• 63323-30-8 (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 37994-80-2 7,8-dihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 
• 57303-99-8 7,8-Dihydroxybenzo[a]pyrene 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 65199-11-3 benzo[a]pyren-7,8-dione 

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.

Tetrabutylammonium Hydroxide: A Reagent for the Base-Catalyzed Dehydration of Vicinal Dihydro Diols of Aromatic Hydrocarbons. Implications to Ion-Pair Chromatography

Vicinal dihydro diols of benzopyrene and benzanthracene are dehydrated to their phenolic derivatives by the methanol eluate of reverse-phase (octadecylsilane) columns previously treated with tetrabutylammonium phosphate.Phenols are also produced by treating the dihydro diols with methanolic tetrabutylammonium hydroxide on removal solvent.In most cases the regioselectivity is markedly different from the acid-catalyzed dehydration.The in situ generated tetrabutylammonium phenoxides are converted to the butyl ethers at high temperatures (150 deg C) but not under th e conditions of dehydration (60 deg C).Tetraethylammonium and tetramethylammonium hydroxides also dehydrate dihydro diols, whereas potassium and sodium hydroxides do not.Dehydration does occur by treatment of dihydro diols with potassium hydroxide in the presence of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) and with sodium methoxide in the presence of tetrabutylammonium chloride.A mechanism is suggested.