SOLASODINE

SOLASODINE Basic information
Product Name:SOLASODINE
Synonyms:(3beta,22alpha,25r)-spirosol-5-en-3-o;Solanum nigrum L.;SOLANCARPIDINE;SOLASOD-5-EN-3BETA-OL;SOLASODINE;PURAPURIDINE;delta5-20betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol;Salasdine
CAS:126-17-0
MF:C27H43NO2
MW:413.64
EINECS:204-774-2
Product Categories:chemical reagent;pharmaceutical intermediate;Alkaloids;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:126-17-0.mol
SOLASODINE Structure
SOLASODINE Chemical Properties
Melting point 200-202°
alpha D25 -98° (c = 0.14 in methanol); D -113° (CHCl3)
Boiling point 532.75°C (rough estimate)
density 1.0159 (rough estimate)
refractive index 1.6400 (estimate)
storage temp. 2-8°C
solubility DMSO: soluble0.5mg/mL, clear (warmed)
pkapKb 6.30(at 25℃)
form powder
color white to beige
optical activity[α]/D -88 to -98°, c = 0.2 in methanol
InChIKeyKOZCINYDCJVLDW-GCGBSLFCSA-N
CAS DataBase Reference126-17-0(CAS DataBase Reference)
NIST Chemistry ReferenceSolasodine(126-17-0)
Safety Information
Safety Statements 22-24/25
RTECS WF1300000
Hazardous Substances Data126-17-0(Hazardous Substances Data)
MSDS Information
SOLASODINE Usage And Synthesis
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.
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.
UsesStarting material for steroidal drugs.
DefinitionChEBI: 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 a plant metabolite, a teratogenic agent, a diuretic, an antifungal agent, a cardiotonic drug, an immunomodulator, an antipyretic, an apoptosis inducer, an antioxidant, an antiinfective agent, an anticonvulsant, a central nervous system depressant and an antispermatogenic agent. It is an azaspiro compound, an oxaspiro compound, an alkaloid antibiotic, a hemiaminal ether, a sapogenin and a steroid alkaloid. It is a conjugate base of a solasodine(1+).
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
Biochem/physiol ActionsSolasodine is a neuroprotective antioxidant glycoalkaloid of Solanum species. Solasodine increases superoxide dismutase (SOD), catalase (CAT),and glutathione (GSH) levels, while reducing lipid peroxidation (LPO) and nitric oxide (NO) levels in the brains of ischemia/reperfusion (I/R)-injury model in rats. Also, Solasonine displayed multiple activities including, anti-cancer and leishmanicidal activities.
Safety ProfilePoison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsSolasodine crystallises (as monohydrate) from MeOH as lustrous plates (on heating, the plates change to needles as they melt and resolidify in needles), or aqueous 80% EtOH, and sublimes at high vacuum. After recrystallisation from H2O, m 198-199o, then from Me2CO/H2O, m 199-201o, it has [] D 22 -109.3o (c 0.581, CHCl3). On TLC with silica gel G (*C6H6/absolute EtOH, 8:2) it has RF 0.45. IR (KBr): max at 10.3, 10.4, 11.2, 11.5 (azaoxaspirane bands). [Schreiber & Rnsch Tetrahedron 20 1939 1964, Uhle J Org Chem 27 656 1962, Kessar et al. Tetrahedron 27 2153 1971, Beilstein 27 III/IV 2000.]
ReferencesRochelmeyer, Chen., Arch. Pharm., 277,329 (1939)
Briggs., J. Chem. Soc., 3, (1942)
Briggs et al., ibid, 3013 (1950)
Absolute configuration: Boll, Phillipsborn., Acta Chem. Scand., 19, 1365 (1965)
Synthesis: Schreiber, Walther, Ronsch., Tetrahedron, 20, 1939 (1964)
Adam, Schreiber., Experientia, 21,471 (1965)
Adam, Schreiber., Tetrahedron, 22,3591 (1966)





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