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| | SOLASONINE Basic information |
| | SOLASONINE Chemical Properties |
| Melting point | 301-303℃ | | alpha | D23 -88° (c = 1.01 in pyridine); D22 -74.5° (c = 0.51 in methanol) | | density | 1.42 | | solubility | DMSO : 100 mg/mL (113.11 mM; Need ultrasonic) | | form | powder | | pka | 12.78±0.70(Predicted) | | color | White-beige | | LogP | 4.350 (est) |
| | SOLASONINE Usage And Synthesis |
| Description | This gly<:oalkaloid occurs in several species of Solanum including S. aviculare, S.
sodomeum, S. verbascifolium and S. xanthocarpum. The alkaloid crystallizes
from 80 per cent EtOH with 4.5 H20, m.p. 245-250°C (dec.), the anhydrous
form being obtained from absolute MeOH. It has [α]25D - 68° (EtOH) and
yields the following salts: hydrochloride, m.p. 265°C; picrate, m.p. 199-201 °C;
picrolonate, m.p. 230-loC and the acetyl derivative, m.p. l35-8°C. On alkaline
hydrolysis, the alkaloid gives solasodine and one mole each of galactose, glucose
and rhamnose. The solution in concentrated H2S04 eventually gives a crimson
colour with a brown fluorescence. | | Uses | α-Solasonine is a natural glycoalkaloid compound which has been shown to inhibit Gli-mediated transcritional activity. | | Definition | ChEBI: Solasonine is an azaspiro compound, an oxaspiro compound and a steroid. | | Purification Methods | Solasonine crystallises from aqueous 80% dioxane or MeOH in needles. [Bell & Briggs J Chem Soc 1 1942, Briggs et al. J Chem Soc 4645 1961, Briggs et al. J Chem Soc 2848 1963.] The picrate crystallises from 30% aqueous EtOH with m 197-198o(dec) [Briggs & Cambie J Chem Soc 1422 1958]. [Beilstein 27 III/IV 2006.] | | References | Oddo et a/., Gazzetta, 35, 27 (1905)
Levi., J. Soc. Chem. Ind., 49, 395T (1930)
Briggs., Nature, 144, 247 (1939)
Briggs.,J. Chem. Soc., 3 (1942)
Briggs, Vining., ibid, 2809 (1953)
Hayes, Scaforth., ibid, 74S (1963) |
| | SOLASONINE Preparation Products And Raw materials |
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