Diosgenin
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Basic information
- CAS
512-04-9- Standard SMILES
C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
WQLVFSAGQJTQCK-VKROHFNGSA-N- Molecular formula
- C27H42O3
- Average molar mass
- 414.6 g/mol
- Monoisotopic mass
- 414.3133952
Overview
Diosgenin is a sapogenin that is spirostan which is substituted by a hydroxy group at the 3beta position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone. It has a role as an antiviral agent, a metabolite, an antineoplastic agent and an apoptosis inducer. It is a sapogenin, a 3beta-sterol, a hexacyclic triterpenoid and a spiroketal. It derives from a hydride of a spirostan.
Names & identifiers
- Preferred name
- Diosgenin
- IUPAC
- (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
- English name
- Diosgenin
- Molecular formula
- C27H42O3
- Molecular weight
- 414.63
Names & synonyms
DIOSGENIN512-04-9Nitogenin(3beta,25R)-spirost-5-en-3-olK49P2K8WLXCHEBI:4629DTXSID00895074(25R)-spirost-5-en-3beta-diolSpirost-5-en-3-ol, (3beta,25R)-NSC-33396(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(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
Show more names
SAPOGENINdiosgenDIOSGENIN (3B-HYDROXY-5A-SPIROSCENE)6-Keto Diosgenin3β-Hydroxy-5-spirosteneSP 37DiosgC08898iosgeninDiosgemom
RefChem:5766DTXCID301324626208-134-3DiosgenineMFCD00016887DISOGENIN(25R)-Spirost-5-en-3beta-ol(2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-Tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol
Properties
Computed structural propertiesFilling in
- XLogP
- 5.7
- Topological polar surface area
- 38.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 746
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]
SpringerMaterials PropertiesCrystal structure
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
200.92 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
208.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 205 · 205-208°C
- Boiling point
- 473.46 °C · 473.46°C (rough estimate)
- alpha
- 25 · D25 -129° (c = 1.4 in CHCl3)
- Density
- 1.0483 · 1.0483 (rough estimate)
- refractive index
- 1.47 · 1.4700 (estimate)
- storage temp.
- 2 · 2-8°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 42.9% (3 of 7) of reports.
Warning
H315 (28.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 7 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/31815
Hazard Classes and CategoriesSkin Irrit. 2 (28.6%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- WH1450000
- hs_code
- 29329990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413
- REACH Registrations
- Active
Chemistry & industry
Applications
OccurrencePrimary sources of diosgenin (a steroidal sapogenin) include Smilax China, Rhizoma polygonati, Solanum incanum, Solanum xanthocarpum, Dioscorea villosa, Trigonella foenum graecum (fenugreek), and Dioscorea Linn (wild yams). It is commercially obtained from wild yam tubers and rootstock[1-2].
Usesantiinflammatory, estrogen
UsesAglicone of saponin dioscin. Diosgenin exists in some food supplements and herbal medicines and lowers plasma cholesterol by increasing fecal cholesterol excretion. e and Progesterone.
Usespregnenolone and progesterone precursor
General DescriptionDiosgenin is a triterpene and a glycone derivative of dioscin. Yams, Trigonella foenum-graecum and Costus speciosus are some of its source.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
17 records
Compound notes
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