|Jmol-3D images||Image 1|
|Molar mass||414.62 g mol−1|
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Diosgenin, a steroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone), diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.
It is present in Costus speciosus, Smilax menispermoidea, species of Paris, Aletris, Trigonella, and Trillium, and many species of Dioscorea - D. althaeoides, colletti, futschauensis, gracillima, hispida, hypoglauca, floribunda, mexicana and composita nipponica, panthaica, parviflora, septemloba, and zingiberensis.
Diosgenin is the precursor for the semisynthesis of progesterone which in turn was used in early combined oral contraceptive pills. The unmodified steroid has estrogenic activity and can reduce the level of serum cholesterol.
Hydrolysis of this saponin leads to scission of the trisaccharide at the 3-position and the formation of the aglycone, diosgenin. Treatment of this acetal with hot acetic anhydride in the presence of toluenesulfonic acid leads initially to protonation of one of the acetal oxygens followed by elimination to form an enol ether. Oxidation by means of chromium trioxide leads to preferential attack at the electron-rich enol ether double bond. In effect, this transformation converts the side chain at C-17 in diosgenin to the acetyl group required for many steroid drugs. Heating that intermediate in with alcoholic sodium hydroxide leads to the elimination of the ester grouping beta to the ketone; there is thus obtained 16-dehydropregnenolone acetate. The presence of the olefin at C-17 allows ready entry to C-19 androstanes and provides the necessary function for the synthesis of potent C-16- and C-16,17-substituted corticosteroids.
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