Structure via PubChem · Public domain (PubChem)
diosgenin
Sign in to saveAlso known as (20R,25R)-spirost-5-en-3beta-ol, (25R)-spirost-5-en-3beta-ol
Diosgenin, a phytosteroid spirostanol 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. It is also present in smaller amounts in a number of other species. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.
Chemical data
- Formula
- C27H42O3
- Molecular weight
- 414.6 g/mol
- IUPAC name
- (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol
- SMILES
- C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
- InChIKey
- WQLVFSAGQJTQCK-VKROHFNGSA-N
- XLogP
- 5.7
- Polar surface area
- 38.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,330 papers- Diosgenin attenuates non-alcoholic fatty liver disease in type 2 diabetes through regulating SIRT6-related fatty acid uptake.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2023
- Diosgenin: Mechanistic Insights on its Anti-inflammatory Effects.Anti-inflammatory & anti-allergy agents in medicinal chemistry · 2022
- Diosgenin: An Updated Pharmacological Review and Therapeutic Perspectives.Oxidative medicine and cellular longevity · 2022
- Diosgenin and Its Analogs: Potential Protective Agents Against Atherosclerosis.Drug design, development and therapy · 2022
- Diosgenin: An ingress towards solving puzzle for diabetes treatment.Journal of food biochemistry · 2022
via PubMed
Wikidata facts
- Mass
- 414.313395
Show 6 more facts
- found in taxon
- Dioscorea alata
- chemical formula
- C₂₇H₄₂O₃
- isomeric SMILES
- C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
- canonical SMILES
- CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)O)C)C)C)OC1
- Commons category
- Diosgenin
- natural product of taxon
- Dioscorea
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Sources
- Industrial uses
- See also
- References
- External links
Diosgenin, a phytosteroid spirostanol 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. It is also present in smaller amounts in a number of other species. 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, D. floribunda, D. futschauensis, D. gracillima, D. hispida, D. hypoglauca, D. mexicana, D. nipponica, D. panthaica, D. parviflora, D. septemloba, and D. zingiberensis.
Excerpted from Wikipedia’s “diosgenin” article, available under the CC BY-SA 4.0 licence.