Diosgenin

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Diosgenin
Diosgenin.svg
Diosgenina3D.png
Names
IUPAC name
(25R)-Spirost-5-en-3β-ol
Preferred 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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.396 Edit this at Wikidata
EC Number
  • 208-134-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1 checkY
    Key: WQLVFSAGQJTQCK-VKROHFNGSA-N checkY
  • InChI=1/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
    Key: WQLVFSAGQJTQCK-VKROHFNGBS
SMILES
  • O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C(=C/C[C@H]3[C@@H]5C4)\C[C@@H](O)CC6)C
Properties
Chemical formula
 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).
☒N  (what is checkY☒N ?)
Infobox references

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, 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.

Sources[]

It is present in detectable amounts in Costus speciosus, , species of Paris, Aletris, Trigonella, and Trillium, and in extractable amounts many species of Dioscorea – D. althaeoides, colletti, composita,[1] floribunda, futschauensis, gracillima, hispida, hypoglauca, mexicana,[2] nipponica, panthaica, parviflora, septemloba,Helicteres isora and zingiberensis.[3]

Industrial uses[]

Diosgenin is a 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]

References[]

  1. ^ "Dioscorea composita". Germplasm Resources Information Network (GRIN). Agricultural Research Service (ARS), United States Department of Agriculture (USDA). Retrieved 2008-09-14.
  2. ^ "Dioscorea mexicana". Germplasm Resources Information Network (GRIN). Agricultural Research Service (ARS), United States Department of Agriculture (USDA). Retrieved 2008-09-14.
  3. ^ "2950 Diosgenin". Retrieved 2007-05-29.[permanent dead link]
  4. ^ Marker RE, Krueger J (1940). "Sterols. CXII. Sapogenins. XLI. The Preparation of Trillin and its Conversion to Progesterone". J. Am. Chem. Soc. 62 (12): 3349–3350. doi:10.1021/ja01869a023.
  5. ^ Djerassi C (December 1992). "Steroid research at Syntex: "the pill" and cortisone". Steroids. 57 (12): 631–41. doi:10.1016/0039-128X(92)90016-3. PMID 1481227. S2CID 5933910.

External links[]

  • Diosgenin at the US National Library of Medicine Medical Subject Headings (MeSH)
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