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SOLASODINE

SOLASODINE Structure
CAS No.
126-17-0
Chemical Name:
SOLASODINE
Synonyms
Solasodin;Salasdine;Nsc178260;SOLASODINE;Salasodine;Sosasodine;NSC 179187;Solanidine-S;PURAPURIDINE;Solancarpine
CBNumber:
CB5132193
Molecular Formula:
C27H43NO2
Molecular Weight:
413.64
MOL File:
126-17-0.mol
MSDS File:
SDS
Modify Date:
2025/1/27 9:38:02

SOLASODINE 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)
pka pKb 6.30(at 25℃)
form powder
color white to beige
optical activity [α]/D -88 to -98°, c = 0.2 in methanol
InChIKey KOZCINYDCJVLDW-GCGBSLFCSA-N
CAS DataBase Reference 126-17-0(CAS DataBase Reference)
NIST Chemistry Reference Solasodine(126-17-0)

SAFETY

Risk and Safety Statements

Safety Statements  22-24/25
RTECS  WF1300000
Hazardous Substances Data 126-17-0(Hazardous Substances Data)

SOLASODINE price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) SML1141 Solasodine ≥95% (HPLC) 126-17-0 5MG ₹6841.4 2022-06-14 Buy
Sigma-Aldrich(India) SML1141 Solasodine ≥95% (HPLC) 126-17-0 25MG ₹27668.7 2022-06-14 Buy
SRL 53771 Solasodine extrapure, 98% 126-17-0 10mg ₹6470 2022-05-26 Buy
SRL 53771 Solasodine extrapure, 98% 126-17-0 25mg ₹15500 2022-05-26 Buy
Product number Packaging Price Buy
SML1141 5MG ₹6841.4 Buy
SML1141 25MG ₹27668.7 Buy
53771 10mg ₹6470 Buy
53771 25mg ₹15500 Buy

SOLASODINE Chemical Properties,Uses,Production

Description

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]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.

Uses

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.

General Description

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

Safety Profile

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

Purification Methods

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.]

References

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)

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SOLASODINE Spectrum

(3beta,22alpha,25r)-spirosol-5-en-3-o SOLANCARPIDINE SOLASOD-5-EN-3BETA-OL SOLASODINE PURAPURIDINE delta5-20betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol Salasdine Salasodine Solanidine-S Solasodin Solasodine hydrochloride base Sosasodine Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-piperidine], spirosol-5-en-3-ol deriv. Spirosol-5-en-3-ol Spirosol-5-en-3-ol, (3beta,22alpha,25R)- 5-SOLASODEN-3BETA-OL Solasod-5-en-3β-ol Salasod-5-en-3β-ol Nsc178260 Solancarpine (3β,22α,25R)-Spirosol-5-en-3-ol NSC 179187 Solasod-5-en-3β-ol (7CI,8CI) Solanum nigrum L. Spirosol-5-en-3-ol, (3β,22α,25R)- (4S,5'R,6aR,6bS,8aS,8bR,9S,10R,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-ol (2'R,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-ol Solasodine extrapure, 98% SOLANI NIGERI HERBA (-)-Solasodine Solasodine-RM Fluoroestradiol Impurity 36 Solasodine, 10 mM in DMSO Solasodine - Bio-X ? 126-17-0 C27H43NO2 chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract Alkaloids