Acta Cryst. (2012). E68, o2357
[ doi:10.1107/S1600536812027912 ]

Diosgenin hemihydrate

M.-G. Hernández Linares, S. Bernès, M. Flores-Alamo, G. Guerrero-Luna and A. A. Martínez-Gallegos

Abstract: Diosgenin [or (22R,25R)-spirost-5-en-3-ol] is the starting material of the Marker degradation, a cheap semi-synthesis of progesterone, which has been designated as an International Historic Chemical Landmark. Thus far, a single X-ray structure for diosgenin is known, namely its dimethyl sulfoxide solvate [Zhang et al. (2005). Acta Cryst. E61, o2324-o2325]. We have now determined the structure of the hemihydrate, C₂₇H₄₂O₃·0.5H₂O. The asymmetric unit contains two diosgenin molecules, with quite similar conformations, and one water molecule. Hydroxy groups in steroids and water molecules form O-HO hydrogen-bonded R₅⁴(10) ring motifs. Fused edge-sharing R(10) rings form a backbone oriented along [100], which aggregates the diosgenin molecules in the crystal structure.

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