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Merck

Synthesis of 19-hydroxy-[7-2H2]androstenedione for human metabolism studies.

Steroids (1990-01-01)
S Ohnishi, T Kosaki, Y Osawa
RESUMEN

19-Hydroxyandrostenedione (19-OHA), highly labeled with deuterium at position 7, was synthesized from unlabeled androstenediol diacetate. The deuterium labels were introduced into the 7-keto compound with dichloroaluminum deuteride to obtain [7-2H2]androstenediol. The labeled androstenediol diacetate was converted to the labeled 19-OHA by a five-step sequence without appreciable loss of deuterium. The labeled 19-OHA is useful as an internal standard for gas chromatography-mass spectroscopy analysis of the endogenous levels and as a tracer for in vivo metabolic studies.