Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam species, such as the Kokoro. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.
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| Names | |
|---|---|
| IUPAC name (25R)-Spirost-5-en-3β-ol | |
| Systematic IUPAC name (2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-4′,4a,6a,7-Tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naphtho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-oxan]-2-ol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.396 |
| EC Number |
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PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C27H42O3 | |
| Molar mass | 414.630 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Sources
It is present in detectable amounts in Costus speciosus, Smilax menispermoidea, Helicteres isora, species of Paris, Aletris, Trigonella, and Trillium, and in extractable amounts from many species of Dioscorea – D. althaeoides, D. colletti, D. composita,[1] D. floribunda, D. futschauensis, D. gracillima, D. hispida, D. hypoglauca, D. mexicana,[2] D. nipponica, D. panthaica, D. parviflora, D. septemloba, and D. zingiberensis.[3]
Industrial uses
Diosgenin is a chemical precursor for several hormones, starting with the Marker degradation process, which includes synthesis of progesterone.[4] The process was used in the early manufacturing of combined oral contraceptive pills.[5] Diosgenin in dietary supplements is not a physiological precursor to estradiol or progesterone, and the use of such products as wild yam has no hormonal activity in the human body.[6]
See also
References
External links
- Diosgenin at the U.S. National Library of Medicine Medical Subject Headings (MeSH)