Solasodin

SOLASODINE Chemische Eigenschaften,Einsatz,Produktion Methoden

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.

• Beschreibung

  There 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]²⁰_D - 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.

• Verwenden

  A potentially useful precursor.

• Verwenden

  antineoplastic, antiinflammatory

• Verwenden

  Solasodine 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.

• Verwenden

  Starting material for steroidal drugs.

• Definition

  ChEBI: 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+).

• Allgemeine Beschreibung

  This 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 Actions

  Solasodine 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.

• Sicherheitsprofil

  Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

• läuterung methode

  Solasodine 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.]

• Einzelnachweise

  Rochelmeyer, 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)

SOLASODINE Upstream-Materialien And Downstream Produkte

Solasodin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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