Solasodine
Basic information
- CAS
126-17-0- Standard SMILES
C[C@@H]1CC[C@@]2(NC1)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
KWVISVAMQJWJSZ-VKROHFNGSA-N- Molecular formula
- C27H43NO2
- Average molar mass
- 413.6 g/mol
- Monoisotopic mass
- 413.32937961
Overview
Solasodine is an oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. It has a role as an antispermatogenic agent, an antioxidant, an antiinfective agent, a central nervous system depressant, an antipyretic, a diuretic, an anticonvulsant, an antifungal agent, a cardiotonic drug, an immunomodulator, a teratogenic agent, an apoptosis inducer and a plant metabolite. It is a hemiaminal ether, a sapogenin, a steroid alkaloid, an azaspiro compound, an oxaspiro compound and an alkaloid antibiotic. It is a conjugate base of a solasodine(1+).
Names & identifiers
- Preferred name
- Solasodine
- 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'-piperidine]-16-ol
- English name
- SOLASODINE
- Molecular formula
- C27H43NO2
- Molecular weight
- 413.64
Names & synonyms
solasodine126-17-0PurapuridineSolanidine-SSolancarpidineSolasodinSolasod-5-en-3beta-olSpirosol-5-en-3-ol, (3beta,22alpha,25R)-L40Y453Y96NSC-178260NSC-179187Salasodine
Show more names
Nsc178260SosasodineNSC 179187Solancarpine
SalasdineCHEBI:9190(3beta,22alpha,25R)-spirosol-5-en-3-olDTXSID101030558delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-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'-piperidine]-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'-piperidine)-16-olRefChem:184222
Database identifiers
- CAS
126-17-0- PubChem CID
- 442985
- DTXSID
DTXSID101030558- ChEMBL
CHEMBL514596、CHEMBL518252- ChEBI
CHEBI:9190- UNII
- L40Y453Y96
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 41.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 749
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Toxins
Color/FormHEXAGONAL PLATES FROM METHANOL OR BY SUBLIMATION IN HIGH VACUUM
Solubility
FREELY SOL IN BENZENE, PYRIDINE, AND CHLOROFORM; MODERATELY SOL IN ALC, METHANOL, AND ACETONE; SLIGHTLY SOL IN WATER; PRACTICALLY INSOL IN ETHER
SOL IN DIOXANE
Melting Point200-202 °C
Optical RotationSPECIFIC OPTICAL ROTATION: -92.4 DEG @ 20 °C/D (BENZENE); +109.8 DEG @ 20 °C/D (CHLOROFORM)
Physical DescriptionSolid; [Merck Index]
Dissociation ConstantsPKB: 6.3
Collision Cross Section
207.15 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
207.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationSpirosol-5-en-3-ol, (3.beta.,22.alpha.,25R)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Spirosol-5-en-3-ol, (3.beta.,22.alpha.,25R)-: Environment tier I assessment
Hazards SummaryEmergency treatment: Plants- solanine; [HSDB] May cause irritation; Effects in high-dose animal studies include parasympathomimetic effects; [MSDSonline] See Solanine.
Special Reports
A REVIEW ON THE UTILIZATION OF SOLASODINE AS A POTENTIAL ECDYSONE ANTAGONIST.[CAMBIE RC, POTTER GJ; UTILIZATION OF SOLASODINE AS A POTENTIAL ECDYSONE ANTAGONIST; CHEM NZ 43 (3): 91-4 (1979)]
A REVIEW AND DISCUSSION CONCERNING THE SOURCES, CHEMISTRY, BIOCHEMISTRY, ISOLATION AND DETERMINATION OF SOLASODINE.[MANN JD; PRODUCTION OF SOLASODINE FOR THE PHARMACEUTICAL INDUSTRY; ADV AGRON 30 207-45 (1978)]
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Natural Pollution Sources
SOLASODINE WAS ISOLATED FROM THE DRIED ROOTS AND LEAVES OF SOLANUM SURATTENSE.
DEVELOPING BERRIES AND LEAVES OF SOLANUM SISYMBRIFOLIUM WERE SCREENED FOR SOLASODINE CONTENT. THE CONTENT INCR WITH THE AGE OF THE BERRIES REACHING ITS MAX VALUE (7.2% OF DRY WT) 45 DAYS AFTER ANTHESIS WHEN THE COLOR WAS SCARLET. IN LEAVES THE CONTENT VARIED FROM 6.4 TO 7.2%.
THE SOLASODINE CONTENT IN THE FRUITS OF SOLANUM MARGINATUM DURING 3 STAGES OF MATURITY WAS INVESTIGATED. THE GREEN FRUIT CONTAINED 2.3% AND THE DEEP YELLOW FRUITS CONTAINED 1.4%.
Non-Human Toxicity Excerpts
Chemistry & industry
Pharmacology
Absorption, Distribution and Excretion
LABELED SOLASODINE WAS INJECTED INTO 2 NORMAL MEN AND INTO SYRIAN HAMSTERS. IN BOTH MEN, BLOOD (3)H WAS LARGELY ASSOCIATED WITH ERYTHROCYTES WHICH AFTER 8 DAYS STILL ACCOUNTED FOR 3.3% OF THE DOSE; PLASMA CONTAINED 1.6%, URINE 7% AND FECES 20% OF THE DOSE. EXCRETION OF (3)H BY HAMSTERS HAD DECLINED TO A VERY LOW LEVEL AFTER 8 DAYS WHEN 22-30% OF THE DOSE HAD BEEN EXCRETED. UNCHANGED SOLASODINE WAS STILL DETECTABLE IN LIVER 22 DAYS AFTER ADMIN.
Uses & manufacturing
Uses
Alkaloid derived from Solanum species; Used to make steroidal drugs; [Merck Index]
STARTING MATERIAL FOR STEROIDAL DRUGS
Methods of Manufacturing
STEROIDAL ALKALOID ISOLATED FROM VARIOUS SOLANUM SPECIES. BY HYDROLYSIS OF SOLASONINE: ROCHELMEYER, ARCH PHARM 277, 329 (1939).
THE ISOLATION AND IDENTIFICATION OF SOLASODINE IN CALLUS CULTURE OF SOLANUM JASMINOIDES ARE DESCRIBED.
Applications
DescriptionThere is still some doubt as to whether this base occurs as such in Solanum aviculare and S. xanthocarpum or whether it is an artifact formed from Sola_x0002_sonine (q.v.) during the extraction process. The base is laevorotatory having [α]20D - 92.4° (C6H6) and the following salts and derivatives have been prepared: hydrochloride, m.p. 314°C; hydriodide, m.p. 293°C; oxalate, m.p. 248°C; tartrate, m.p. 222°C; picrate, m.p. 1.4l-2°C; picrolonate, m.p. 234°C; acetyl derivative, m.p. 195°C; benzoyl compound, m.p. 2l6-7°C and the 3:5-dinitrobenzoyl derivative, m.p. 191.5-193°C. The alkaloid forms a sparingly soluble digitonide and yields Diels's hydrocarbon on selenium dehydrogenation.
UsesStarting material for steroidal drugs.
UsesSolasodine is a potentially useful precursor for steroidal compounds and hormones, this is usually found in plants from the solanaceae family. It also has potent cytotoxic and anti-inflammatory effects.
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