56182-99-1

Usage

InChI:InChI=1/C21H14O/c1-22-19-12-15-11-14-5-2-3-7-16(14)17-10-9-13-6-4-8-18(19)20(13)21(15)17/h2-12H,1H3

Upstream product

• 110418-68-3 (+/-)-trans-4-methoxy-5-hydroxy-4,5-dihydrobenzopyrene 
• 74-88-4 methyl iodide 
• 37574-47-3 4,5-dihydro(epoxy) benzopyrene 

Relevant academic research and scientific papers

Chemical derivatization and Shpol'skii spectrofluorometric determination of benzo[a]pyrene metabolites in fish bile

The practical applicability and analytical performance of laser-excited Shpol'skii spectroscopy (LESS) for the determination of benzo[a]pyrene (BaP) metabolites was studied. Quantitation of these compounds in fish bile can provide insight into the BaP uptake from a contaminated aquatic environment (biomonitoring). Chemical derivatization of hydroxylated BaP metabolites with methyl iodide (to improve the compatibility with the Shpol'skii matrix) was tested. The methylation of phenolic metabolites was rapid and quantitative, but with BaP-dihydro diol metabolites, mixtures of methylation and elimination products were formed. An analytical procedure was developed for the quantitative determination of 3-OH-BaP, the major BaP metabolite detected in bile from flounder (Platichthys flesus). With LESS, the detection limit was 0.005 ng/mL (200 amol); the repeatability was 16%. The method was applied to a mesocosm experiment in which flounders were exposed to different sediments. The average BaP uptake from Rotterdam harbor sediment was 40 times higher than the uptake from Wadden Sea sand. Direct contact with the sediments was a major route of exposure. The usefulness of the method for the biomonitoring of polycyclic aromatic hydrocarbon stress in the aquatic environment is discussed.

Absolute Configurations of K-Region Epoxide Enantiomers of 3-Methylcholanthrene, Benzanthracene, and Benzopyrene

The absolute configurations of K-region epoxide enantiomers of 3-methylcholanthrene, benzanthracene, and benzopyrene have been determined via their monomethyl ether derivatives.Methoxylation of each racemic or enantiomeric epoxide by sodium methoxide resulted in a pair of monomethyl ether derivatives, which were separated by normal-phase high-performance liquid chromatography (HPLC).The position of the methoxy group was determined by products formed by acid-catalyzed dehydration and/or demethanolization of each monomethyl ether derivative.Enantiomers of each epoxide and its methoxylated derivatives were resolved by at least two of the four Pirkle chiral stationary phase HPLC columns utilized in this study.The absolute stereochemistries of enantiomeric monomethyl ether derivatives were established by comparing their circular dichroism spectra with those of enantiomeric monomethyl ether derivatives derived from trans dihydrodiol enantiomers of known absolute configurations.The absolute configuration of each epoxide enantiomer was deduced from the location of the methoxy group and the absolute configuration of enantiomeric monomethyl ether derivatives.Results indicate that the method described is useful in general for the determination of absolute configurations of K-region epoxide enantiomers of polycyclic aromatic hydrocarbons.