Diosgenin hemihydrate

Abstract

Diosgenin [or (22R,25R)-spirost-5-en-3β-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—H...O 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

Solanum steroidal glycoalkaloids: structural diversity, biological activities, and biosynthesis

“…92 Diosgenin is an important starting point for the commercial synthesis or semi-synthesis of pregnenolone, cortisone, progesterone, and other pharmaceuticals. 93,94 It has also been used for the semi-synthesis of some important SGA. The unique spiroketal system joins the E and F-rings in steroidal sapogenins.…”

Structural Diversity of Diosgenin Hydrates: Effect of Initial Concentration, Water Volume Fraction, and Solvent on Crystallization

“…The molecular structure of diosgenin is shown in Scheme . To the best of our knowledge, only one dimethyl sulfoxide solvate and one hemihydrates (labeled as HH-I) of diosgenin are known. The structural analyses display that steroids functionalized with hydroxyl groups have a propensity to form hydrates, and in these cases, the hydroxyl group acts as hydrogen bond recognition site to interact with the lattice water molecule. − Therefore, in our study, diosgenin was selected as a model to investigate the controlling factors during the formation of hydrates.…”

Unveiling the Chemical Composition of Sulfur-Fumigated Herbs: A Triple Synthesis Approach Using UHPLC-LTQ-Orbitrap MS—A Case Study on Steroidal Saponins in Ophiopogonis Radix

“…MS 2 [911]: 869(100), 851(58), 737 (21), 779 (10), 723 (8), 652 (6), 719( 6) MS 2 [927]: 885(100), 867(54), 753 (16), 885 (13), 735 (7), 739 (5), 721 (37), 903 (32), 933 (31), 753 (15), 1061 (13), 899 (12), 591(8) (30), 903 (32), 933 (31), 753 (15), 1061 (13), 899 (12), 591 (39), 949 (26), 787 (22), 1077 (15), 769 (15), 915 (13), 607 (10) Hydroxyl-Ophiopogonin J/Ophiopogonin (11), 1033 (9), 1015 (7), 1063 (5), 883(3), 899(1)…”