SOLASODINE

Описание

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.

Использование

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.

Общее описание

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

Профиль безопасности

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

Методы очистки

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.]

использованная литература

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)