Preparation and application of 2,4,6-tribromo-[13C6]-anisole for the quantitative determination of 2,4,6-tribromoanisole in wine

Abstract

An expedient preparation of 2,4,6-tribromo-[13C6]-phenol (13C6-TBP) and its conversion to 2,4,6-tribromo-[13C6]-anisole (13C6-TBA) is described. The method involves the bromination of an aqueous solution of 13C6-phenol and subsequent methylation of the corresponding tribromophenol with methyl iodide. Mass spectrometric and nuclear magnetic resonance analyses of 13C6-TBP and 13C6-TBA confirm that their chemical and isotopic purities were better than 99%. The application of 13C6-TBA to the quantitative analysis of the known musty taint 2,4,6-tribromoanisole (TBA) in wine using solid phase microextraction coupled to gas chromatography-mass spectrometry, operated in the selected ion monitoring mode, is described. The detection limit for TBA was 2 ng l-1, based on a minimum signal response greater than three times the background noise. Crown Copyright © 2008.