| Identification | Back Directory | [Name]
SOLASONINE | [CAS]
19121-58-5 | [Synonyms]
NSC 82149
PURAPURIN
SOLASONIN
SOLASONINE
PURAPURINE
SOLANINE S
SOLANCARPIN
Solasoonine
α-Solasonine
SOLASODAMINE
SOLASONINE(RG)
ALPHA-SOLASONINE
Solasonine 19121-58-5
Solasonine
alpha-Solasonine
[(22R,25R)-Spirosol-5-en-3β-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-3-O-(β-D-glucopyranosyl)-β-D-galactopyranoside
5-SOLASODEN-3BETA-OL 3-O-6-D-DEOXY-ALPHA-L-MONOPYRANOSYL (1->2)-BETA-D-GLUCOPYRANOSYL (1->3)-BETA-D-GALACTOPYRANOSIDE
β-D-Galactopyranoside, (3β,22α,25R)-spirosol-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-
.beta.-D-Galactopyranoside, (3.beta.,22.alpha.,25R)-spirosol-5-en-3-yl O-6-deoxy-.alpha.-L-mannopyranosyl-(1?2)-O-.beta.-D-glucopyranosyl-(1?3)-
(2S,3R,4S,5S,6R)-2-(((2R,3S,4S,5R,6R)-3-hydroxy-2-(hydroxymethyl)-6-(((2'S,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-4-yl)oxy)-5-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-4-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | [EINECS(EC#)]
242-826-6 | [Molecular Formula]
C45H73NO16 | [MDL Number]
MFCD00017611 | [MOL File]
19121-58-5.mol | [Molecular Weight]
884.06 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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) |
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