Synthesis of deuterium-labeled d(3)-androstenone and d(3)-skatole for boar taint analysis

The steroidal pig pheromone androstenone (5 alpha-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 H-2-labeled internal standards of androstenone and skatole for stable isotope dilution assay-gas chromatogr...

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Published inJournal of labelled compounds & radiopharmaceuticals Vol. 54; no. 9-10; pp. 591 - 596
Main Authors Fischer, Jochen, Elsinghorst, Paul W., Wuest, Matthias
Format Journal Article
LanguageEnglish
Published MALDEN Wiley 01.08.2011
Subjects
Biochemical Research Methods
Biochemistry & Molecular Biology
Chemistry
Chemistry, Analytical
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
deuteration
STEROIDS
androstenone
CASTRATION
boar taint
skatole
MASS-SPECTROMETRY
GC-MS
PLASMA
INDOLE
deuterium
SIDA
PIGLETS
FAT
MALE PIGS
ANDROSTENONE LEVELS
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Summary:The steroidal pig pheromone androstenone (5 alpha-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 H-2-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 Delta 5,6-double bond of a hydrophobic steroid in a polar, D2O-containing solvent mixture. Moreover, the utilization of D2O 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.
ISSN:0362-4803
DOI:10.1002/jlcr.1895