Diosgenin

Source: Wikipedia, the free encyclopedia.
Diosgenin
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 Edit this at Wikidata
EC Number
  • 208-134-3
UNII
  • 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
  • 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
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).
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Diosgenin, a

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.

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

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

  1. ^ "Dioscorea composita". Germplasm Resources Information Network. Agricultural Research Service, United States Department of Agriculture. Retrieved 2008-09-14.
  2. ^ "Dioscorea mexicana". Germplasm Resources Information Network. Agricultural Research Service, United States Department of Agriculture. Retrieved 2008-09-14.
  3. ^ "2950 Diosgenin". Retrieved 2007-05-29.[permanent dead link]
  4. doi:10.1021/ja01869a023
    .
  5. S2CID 5933910
    .
  6. ^ Medigović I, Ristić N, Živanović J, Šošić-Jurjević B, Filipović B, Milošević V, Nestorović N “Diosgenin does not express estrogenic activity: a uterotrophic assay” Can J Physiol Pharmacol. 2014 Apr;92(4):292-8. doi: 10.1139/cjpp-2013-0419. Epub 2014 Feb 5. PMID: 24708211

External links

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