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The title steroidal compound, C(31)H(49)NO(5), resulted from the selective oximation of (23R)-23-acetyl-sarsasapogenin acetate. One- and two-dimensional (1)H and (13)C NMR spectra, as well as IR data, are in agreement with the presence of a ketoxime group at C-23. However, recrystallization in slightly acidic media affords the title compound in the rare zwitterionic oxime form, as a consequence of migration of the hydr-oxy H atom to the N atom in the oxime group. This H atom is clearly detected and its position was refined from X-ray data. The geometry for the C=N(+)(H)-O(-) group features long C=N and short N-O bond lengths compared to non-zwitterionic oximes. The ketoxime is stabilized with the E configuration, avoiding steric hindrance between the oxime O atom and H atom at C-23. The sum of the angles around the oxime N atom is 359.6°, giving a planar configuration for that atom, as expected for sp(2) hybridization.

The zwitterion (23′E)-(23R,25S)-23-[1-(oxidoiminio)ethyl]-5β-spirostan-3β-yl acetate