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

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

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

• 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 
• 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%.

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

The hypervalent iodine reagents o-iodoxybenzoic acid (IBX) and bis(trifluoro-acetoxy)iodobenzene (BTI) are shown to be general reagents for regio-controlled oxidation of polycyclic aromatic phenols (PAPs) to specific isomers (ortho, para, or remote) of polycyclic aromatic quinones (PAQs). The oxidations of a series of PAPs with IBX take place under mild conditions to furnish the corresponding ortho-PAQs. In contrast, oxidations of the same series of PAPs with BTI exhibit variable regiospecificity, affording para-PAQs where structurally feasible and ortho-PAQs or remote PAQ isomers in other cases. The structures of the specific PAQ isomers formed are predictable on the basis of the inherent regioselectivities of the hypervalent iodine reagents in combination with the structural requirements of the phenol precursors. IBX and BTI are recommended as the preferred reagents for regio-controlled oxidation of PAPs to PAQs.

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.

Modulation of cytochrome P4501-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells.

Allyl sulfides such as diallyl sulfide (DAS), diallyl disulfide (DADS), and diallyl trisulfide (DATS), typical flavor components of Allium vegetables, have been shown to inhibit benzo[a]pyrene (B[a]P)-induced carcinogenesis in animal models. As a possible mechanism of this inhibition, the effect of these volatile substances on cytochrome P450 (CYP)1 (CYP1A1, 1A2 and 1B1)-mediated bioactivation of B[a]P was investigated using a human hepatoma cell model (HepG2). DADS and DATS inhibited the B[a]P-induced ethoxyresorufin O-deethylase (EROD) activity, a marker enzyme for CYP1, by 30-90% and 70-95% at 100-1,000 microM concentration, respectively. The cell viability, an indicator of the capacity to inhibit B[a]P bioactivation, was increased by treatments of 100-1,000 microM DADS and 10-100 microM DATS. Immunoblot results indicated that the B[a]P inducible CYP1A2 protein was suppressed by 100-1,000 microM of DADS and 10-100 microM of DATS, but CYP1A1 and 1B1 were not detectable in any microsomes. Analysis of B[a]P metabolites revealed that the level of 7,8-diol formed was significantly reduced in the DADS and DATS treated microsomes as compared to the control. The level of 9,10-diol and 4,5-diol formed was also lowered by the allyl sulfide treatments. These results suggest that the protective mechanism of allyl sulfides on B[a]P-induced carcinogenesis is possibly related with the modulation of CYP1-mediated bioactivation of B[a]P.

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.

Synthesis of the o-Quinones and Dihydro Diols of Polycyclic Aromatic Hydrocarbons from the Corresponding Phenols

Terminal-ring trans-dihydro diol metabolites have been implicated as the ultimate carcinogenic forms of polycyclic aromatic hydrocarbons.Synthesis of these dihydro diols from the related polycyclic phenols in two steps via oxidation to the corresponding o-quinones with either Fremy's salt or phenylseleninic anhydride followed by stereospecific reduction with lithium aluminum hydride is described.The non-K-region quinones and trans-dihydro diols of naphthalene, anthracene, phenanthrene, benzanthracene, benzopyrene, and 7,12-dimethylbenzanthracene are synthesized via this approach.Although poor yields (1-4percent) were previously reported for the reduction of non-K-region quinones, an improved experimental procedure has been developed which affords the trans-dihydro diols free of the isomeric cis-dihydro diols in generally good yields.Major byproducts are the corresponding hydroquinones, previously undetected, and the related tetrahydro diols.The latter are the major products of reduction of the poorly soluble quinones of benzopyrene and benzanthracene and are shown to arise through further reduction of the dihydro diols.Since the tetrahydro diols are convertible to dihydro diols and the hydroquinones are reoxidizable to quinones, good overall conversions of quinones to dihydro diols are attainable. trans-3,4-Dihydroxy-3,4-dihydro-7,12-dimethylbenzanthracene synthesized in these studies is the most potent tumorigenic hydrocarbon metabolite tested to date.