Sarsasapogenin
Basic information
- CAS
126-19-2- Standard SMILES
C[C@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
GMBQZIIUCVWOCD-WWASVFFGSA-N- Molecular formula
- C27H44O3
- Average molar mass
- 416.6 g/mol
- Monoisotopic mass
- 416.32904526
Overview
(25S)-5beta-spirostan-3beta-ol is a sapogenin.
Names & identifiers
- Preferred name
- Sarsasapogenin
- IUPAC
- (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol
- English name
- Sarsasapogenin
- Molecular formula
- C27H44O3
- Molecular weight
- 416.64
Names & synonyms
Sarsasapogenin126-19-2ParigeninSarsagenin(25S)-5beta-Spirostan-3beta-olSpirostan-3-ol, (3beta,5beta,25S)-CFS802C28FNSC 1615PURE SARSASAPOGENIN(3beta,5beta,25S)-spirostan-3-olCHEBI:15578DTXSID00903921
Show more names
SARSAPOGENINSARSAPOGENINEPERIGENINSarsasapogeinSASARASAPOGENINSarsasapogenin-RM
NSC-1615(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-olsarsageninasarsageninesarsageninum(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-oxane)-16-olRefChem:931315DTXCID501331881
Database identifiers
- CAS
126-19-2- PubChem CID
- 92095
- DTXSID
DTXSID00903921- ChEMBL
Properties
Computed structural properties
- XLogP
- 6.5
- 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
- 694
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point200 - 201.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 194 °C · 194°C
- alpha
- 25 · D25 -75°; 25546 -89° (c = 0.5 in CHCl3)
- Boiling point
- 474.91 °C · 474.91°C (rough estimate)
- Density
- 1.0362 · 1.0362 (rough estimate)
- refractive index
- 1.47 · 1.4700 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 mg/ml; · DMF: 2 mg/ml; DMSO: 0.2 mg/ml; Ethanol: 2 mg/ml; Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
- form
- A crystalline solid
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 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2932990090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P280-P261-P271
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionSmilagengenin is a steroidal saponin with antitumor activity, which is mainly used in refreshing beverages, foaming sweets, mixed wine, etc.
UsesSarsasapogenin has cytotoxic properties and is used to develop lead structures for cancer drugs. Sarsasapogenin is also identified to effectively lower the production of Aβ amyloids and stimulate neurite ogrowth in neuronal cell cultures.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: (25S)-5beta-spirostan-3beta-ol is a sapogenin.
Related reactions
8 records
Compound notes
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