65199-11-3

Basic information

• Product Name: benzo(a)pyrene-7,8-dione
• Synonyms: benzo(a)pyrene-7,8-dione;7,8-BENZO(A)PYRENEQUINONE;Benzopyrene Related Compound 12
• CAS NO: 65199-11-3
• Molecular Formula: C₂₀H₁₀O₂
• Molecular Weight: 282.29
• Mol File: 65199-11-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 526.9°C at 760 mmHg
• Flash Point: 231.5°C
• Appearance: /
• Density: 1.446g/cm³
• Vapor Pressure: 3.44E-11mmHg at 25°C
• Refractive Index: 1.876
• CAS DataBase Reference: benzo(a)pyrene-7,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: benzo(a)pyrene-7,8-dione(65199-11-3)
• EPA Substance Registry System: benzo(a)pyrene-7,8-dione(65199-11-3)

Safety Data

• Hazardous Substances Data: 65199-11-3(Hazardous Substances Data)

Usage

Description

Benzo(a)pyrene-7,8-dione, also known as B(a)P-7,8-dione, is an o-quinone resulting from the formal oxidation of both hydroxy groups of benzo[a]pyrene-cis-7,8-dihydrodiol. It is a metabolite of the widespread carcinogen benzo[a]pyrene (B205800), which is a known carcinogen.

Uses

Used in Environmental Monitoring and Toxicology Research:
Benzo(a)pyrene-7,8-dione is used as a biomarker for exposure to polycyclic aromatic hydrocarbons (PAHs) in various environmental and occupational settings. Its presence in samples indicates the presence of PAHs, which are associated with adverse health effects, including cancer.
Used in Cancer Research:
Benzo(a)pyrene-7,8-dione is used as a research tool in cancer research to study the mechanisms of carcinogenesis and the effects of PAHs on cellular processes. It helps researchers understand the molecular pathways involved in the development of cancer and identify potential targets for therapeutic intervention.
Used in Analytical Chemistry:
Benzo(a)pyrene-7,8-dione is used as a reference compound in analytical chemistry for the development and validation of methods for the detection and quantification of PAHs in environmental and biological samples. Its well-defined chemical properties make it suitable for calibrating instruments and establishing analytical protocols.

InChI:InChI=1/C20H10O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10H

Upstream product

• 19821-80-8 1,3-dibromo-2-iodo-benzene 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 6751-75-3 2-bromoresorcinol 
• 156641-98-4 (6-methoxy-2-naphthalene)boronic acid 
• 115237-06-4 (((2-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene 
• 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 
• 50-32-8 benzopyrene 
• 17550-74-2 cis-7,8-dihydroxy-7,8,9,10-tetrahydrobenzopyrene 
• 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 
• 1397284-44-4 8-hydroxy-benzo[a]pyrene-7-O-sulfate 
• 1397284-45-5 C₂₀H₁₂O₅S 
• 1329639-24-8 C₂₁H₁₄O₂ 
• 1329639-23-7 O-8-methyl-(benzo[a]pyrene-7,8-catechol) 
• 849830-97-3 acetic acid 2-acetoxymethyl-5-{2-[7,8-bis-(tert-butyl-dimethyl-silanyloxy)-benzo[def]chrysen-10-ylamino]-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester 
• 849831-01-2 5-{2-[7,8-bis-(tert-butyl-dimethyl-silanyloxy)-benzo[def]chrysen-10-ylamino]-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-2-hydroxymethyl-tetrahydro-furan-3-ol 
• 849830-98-4 10-{9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-ylamino}-benzo[def]chrysene-7,8-dione 
• 849830-92-8 10-amino-7,8-bis(benzoyloxy)benzo[a]pyrene 
• 57303-99-8 7,8-Dihydroxybenzo[a]pyrene 
• 57404-88-3 (-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene 
• 37994-80-2 7,8-dihydroxy-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%.

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.

SYNTHESIS OF NON-K-REGION ORTHO-QUINONES OF POLYCYCLIC AROMATIC HYDROCARBONS FROM CYCLIC KETONES

Non-K-region o-quinones of polycyclic aromatic hydrocarbons are prepared in four steps from cyclic ketones via dehydrogenation of tetrahydrodiols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.