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Mass spectra of 17ξ‐hydroxy‐5ξ‐androstane C(3) ketone and C(3ξ) alcohol isomers
Author(s) -
Jackson ChungJa Choi,
Templeton John F.,
Reimer Mark L. J.,
Westmore John B.
Publication year - 1985
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210200105
Subject(s) - androstane , chemistry , ketone , fragmentation (computing) , alcohol , mass spectrum , molecule , ion , electron ionization , medicinal chemistry , mass spectrometry , stereochemistry , organic chemistry , chromatography , ionization , computer science , operating system
Positive ion electron impact mass spectral data for the four isomeric 17ξ‐hydroxy‐17ξ‐methyl‐5ξ‐androstane C(3) ketones and the eight isomeric C(3ξ) alcohols are reported. In contrast to earlier reports, no general correlation was observed between the [MH 2 O] + ˙/[M] + ˙ ratio and the configuration at C(17). The ratios of the intensity of several fragment ions to that of the molecular ion do differentiate between the 5α‐ and 5β‐isomers in both C(3) ketones and alcohols, the extent of fragmentation being greater for 5β‐steroids. All of these fragments probably involve elimination of a water molecule at some stage in their formation. Elimination of water is also enhanced for 3α‐ v. 3β‐hydroxysteroids, particularly in a 5β‐isomer.