77208-18-5

Usage

Uses

Used in Chemical Synthesis:
(1R,2S,3S,4R)-1,2,3,4-tetrahydrochrysene-1,2,3,4-tetrol is utilized as a key intermediate in the synthesis of various metabolites and derivatives of chrysene. Its unique structure and stereochemistry make it a valuable building block for creating complex organic molecules with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1R,2S,3S,4R)-1,2,3,4-tetrahydrochrysene-1,2,3,4-tetrol is used as a precursor for the synthesis of Dihydrodiol and Diol Epoxide metabolites of chrysene. These metabolites have been shown to possess carcinogenic activity, making them important targets for research into the development of drugs that can modulate or inhibit their effects, potentially leading to novel cancer therapies or preventive agents.
Used in Environmental and Toxicological Studies:
Due to the carcinogenic properties of the Dihydrodiol and Diol Epoxide metabolites derived from (1R,2S,3S,4R)-1,2,3,4-tetrahydrochrysene-1,2,3,4-tetrol, (1R,2S,3S,4R)-1,2,3,4-tetrahydrochrysene-1,2,3,4-tetrol can also be used in environmental and toxicological studies. It can help researchers understand the mechanisms of chrysene-induced carcinogenesis and develop methods for assessing the environmental impact of such compounds, as well as strategies for mitigating their harmful effects.

Upstream product

• 64920-33-8 trans-1,2-dihydroxy-anti-3,4-epoxy-1,2,3,4-tetrahydrochrysene 

Relevant academic research and scientific papers

Detection of DNA and globin adducts of polynuclear aromatic hydrocarbon diol epoxides by gas chromatography - Mass spectrometry and [3H]CH3I postlabeling of released tetraols

Gas chromatography - negative ion chemical ionization mass spectrometry - selected ion monitoring (GC-NICI-MS-SIM) was employed to detect tetramethyl ether derivatives of tetraols formed upon hydrolysis of DNA and globin adducts derived from diol epoxides of benzo[α]-pyrene (BP) and other polynuclear aromatic hydrocarbons (PAH). The tetramethyl ether derivatives could also be detected by [3H]CH3I postlabeling. The methodology involves the following steps: (1) isolation of DNA or globin; (2) mild acid hydrolysis under vacuum; (3) isolation of the resulting tetraols and derivatization to the corresponding tetramethyl ethers using methyl sulfinyl carbanion and unlabeled or 3H-labeled CH3I; (4) analysis by GC-NICI-MS-SIM or HPLC with radioflow detection. The optimum conditions for hydrolysis of adducts and derivatization of the resulting tetraols as well as the feasibility of this approach for detecting PAH adducts in mice and humans were explored. Using the set of four BP-tetraols that can be formed upon hydrolysis of adducts formed from r-7,t-8-dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[α]pyrene (anti-BPDE) or r-7,t-8-dihydroxy-c-9,10-epoxy-7,8,9,10-tetrahydrobenzo-[α]pyrene (syn-BPDE) as models, the stability of the tetraols under the hydrolysis conditions was investigated. Adducts derived from anti-BPDE yield predominantly the stable r-7,t-8,9-c-10-tetrahydroxy-7,8,9,10-tetrahydrobenzo[α]pyrene (trans-anti-BP-tetraol), while adducts derived from syn-BPDE released cis-syn-BP-tetraol as a major hydrolysis product. Hydrolysis under vacuum significantly increased the recovery of tetraols. Conditions for derivatization of the BP-tetraols as well as tetraols derived from several other PAH anti-diol epoxides were investigated. Tetramethyl ethers proved to be superior derivatives that were stable, easy to prepare in high yields, and detectable with high sensitivity by GC-NICI-MS-SIM (1-50 fmol per injection). Alternatively, these derivatives could be detected by HPLC with radioflow detection if [3H]CH3I were employed for derivatization. The methodology was tested by comparing levels of DNA and globin adducts in mice treated with either unlabeled or 3H-labeled BP. Good agreement was obtained among the GC-NICI-MS-SIM, [3H]CH3I postlabeling, and conventional radiometric methods. Moreover, analysis of human hemoglobin by GC-NICI-MS-SIM resulted in detection of adducts derived from anti-BPDE and r-1,t-2-dihydroxy-t-3,4-epoxy-1,2,3,4-tetrahydrochrysene. The results of this study demonstrate that GC-NICI-MS-SIM of tetramethyl ethers of tetraols formed by hydrolysis of PAH diol epoxide DNA and globin adducts is a promising approach for detection and quantitation of adducts derived from a broad range of PAH.