Basic information
- CAS
126-17-0- Standard SMILES
CC1CCC2(NC1)OC1CC3C4CC=C5CC(O)CCC5(C)C4CCC3(C)C1C2C- InChIKey
KWVISVAMQJWJSZ-UHFFFAOYSA-N- Molecular formula
- C27H43NO2
- Average molar mass
- 413.6 g/mol
- Monoisotopic mass
- 413.32937961
Overview
solassodine has been reported in Solanum violaceum, Solanum aviculare, and other organisms with data available.
Names & identifiers
- Preferred name
- Npc147835
- IUPAC
- 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
RefChem:1092725Npc147835Spirosol-5-en-3-olSolasod-5-en-3 beta-olSOLASODINE HYDROCHLORIDE BASENSC179187Solasod-5-en-3.beta.-olSolancarpine(-)-SolasodineNSC 178260Spirosol-5-en-3-ol,22.alpha.,25R)-Solauricidine
Show more names
SolasodinSalasdineNsc178260SOLASODINESalasodineNSC 179187Solanidine-SPURAPURIDINE
SosasodineSolanidine S(3|A,22|A,25R)-Spirosol-5-en-3-olSolasod-5-en-3beta -olOprea1_090106orb1303271CHEMBL1964743SCHEMBL12838252
Database identifiers
- CAS
126-17-0、1415-77-6- PubChem CID
- 5250
- DTXSID
DTXSID40871610- ChEMBL
CHEMBL1964743
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
Melting Point200 - 201 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 200 · 200-202°
- alpha
- 25 · D25 -98° (c = 0.14 in methanol); D -113° (CHCl3)
- Boiling point
- 532.75 °C · 532.75°C (rough estimate)
- Density
- 1.0159 · 1.0159 (rough estimate)
- refractive index
- 1.64 · 1.6400 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 0.5 mg/mL, · DMSO: soluble0.5mg/mL, clear (warmed)
- pka
- 6.3 · pKb 6.30(at 25℃)
- form
- powder
- color
- white to beige
- optical activity
- -88 to · [α]/D -88 to -98°, c = 0.2 in methanol
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- rtecs
- WF1300000
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazardous Substances Data
- 126-17-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
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.
Usesantineoplastic, antiinflammatory
UsesA potentially useful precursor.
General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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