✦ LIBER ✦

Synthesis of deuterium-labeled d3-androstenone and d3-skatole for boar taint analysis

✍ Scribed by Jochen Fischer; Paul W. Elsinghorst; Matthias Wüst

Book ID: 102368925
Publisher: John Wiley and Sons
Year: 2011
Tongue: French
Weight: 219 KB
Volume: 54
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.1895

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✦ Synopsis

The steroidal pig pheromone androstenone (5__α__‐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 ^2^H‐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 Δ5,6‐double bond of a hydrophobic steroid in a polar, D~2~O‐containing solvent mixture. Moreover, the utilization of D~2~O as a deuterium source with in situ formation of D~2~ by means of Mg^0^ was found to be a very feasible and convenient alternative with respect to costs and technical effort.

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