Synthesis of deuterium-labeled d_3 androstenone and d_3 - skatole for boar taint analysis

摘要

The steroidal pig pheromone androstenone (5a-androst-16-en-3-one) as well as the indole derivate skatole are known to be the major compounds contributing to boar taint. The preparation of ~2H-labeled internal standards of androstenone and skatole for stable isotope dilution assay-gas chromatography-mass spectrometry analysis of pig back fat samples is presented. The synthesis of d_3-androstenone is highlighted by a palladium catalyzed deuteration of a A5,6-double bond of a hydrophobic steroid in a polar, D_2O-containing solvent mixture. Moreover, the utilization of D_2O as a deuterium source with in situ formation of D_2 by means of Mg° was found to be a very feasible and convenient alternative with respect to costs and technical effort.