126-17-0 Usage
Description
Solasodine is a naturally occurring steroidal alkaloid that serves as a valuable precursor for the synthesis of steroidal compounds and hormones. It is typically found in plants belonging to the Solanaceae family and exhibits potent cytotoxic and anti-inflammatory properties.
Uses
Used in Pharmaceutical Industry:
Solasodine is used as a starting material for the production of steroidal drugs due to its potential as a precursor for steroidal compounds and hormones.
Used in Anticancer Applications:
Solasodine is used as an antineoplastic agent, leveraging its cytotoxic effects to target and eliminate cancer cells.
Used in Anti-inflammatory Applications:
Solasodine is utilized for its anti-inflammatory properties, helping to reduce inflammation and alleviate related symptoms.
Used as a Reference Substance:
As a primary reference substance with assigned absolute purity, Solasodine is used for various analytical and research purposes, ensuring accurate measurements and comparisons in scientific studies.
General Description:
Solasodine is a compound with specific optical activity, being laevorotatory with a specific rotation of [α]20D 92.4° (C6H6). Several salts and derivatives of Solasodine have been prepared, including hydrochloride, hydriodide, oxalate, tartrate, picrate, picrolonate, acetyl derivative, benzoyl compound, and the 3:5-dinitrobenzoyl derivative, each with distinct melting points. Additionally, the alkaloid forms a sparingly soluble digitonide and yields Diels's hydrocarbon upon selenium dehydrogenation. There is some uncertainty regarding its natural occurrence in Solanum aviculare and S. xanthocarpum, as it may be an artifact formed from Solasonine during the extraction process.
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.
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)
Check Digit Verification of cas no
The CAS Registry Mumber 126-17-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 6 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 126-17:
(5*1)+(4*2)+(3*6)+(2*1)+(1*7)=40
40 % 10 = 0
So 126-17-0 is a valid CAS Registry Number.
InChI:InChI=1/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20?,21?,22+,23+,24?,25+,26+,27-/m1/s1
126-17-0Relevant articles and documents
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Singh,S. et al.
, p. 2020 - 2022 (1974)
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Lewis,Liljegren
, p. 2193,2195 (1970)
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Aslanov,S.M.
, (1972)
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Revision of the Structure of N, O-Diacetylsolasodine. Unusual Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine
Czajkowska-Szczykowska, Dorota,Jastrzebska, Izabella,Rode, Joanna E.,Morzycki, Jacek W.
, p. 59 - 65 (2019)
The steroidal alkaloid solasodine (1) undergoes inversion of configuration at the C-22 spiro atom when treated with acetic anhydride-pyridine at ambient temperature. The basic solvolysis of the N,O-diacetyl derivative (2) reverses the reaction, yielding the starting solasodine (1). The mechanisms of both processes (acetylation and deacetylation) were studied in terms of possible reaction pathways.
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Bell,Briggs
, p. 1 (1942)
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Novruzov,E.N. et al.
, (1973)
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Schreiber,Adam
, p. 3591,3594 (1966)
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Briggs,Brooker
, p. 1419,1420, 1421 (1958)
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Novruzov et al.
, (1975)
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Kessar,S.V. et al.
, p. 2869 - 2875 (1971)
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Facile synthesis of solasodine based on a mild halogenation-ring opening reaction of spiroketals in steroidal sapogenins
Wu, Jing-Jing,Shi, Yong,Tian, Wei-Sheng
, p. 1215 - 1217 (2015/03/04)
Herein we report a halogenation-ring opening reaction of spiroketals in steroidal sapogenins at room temperature to gain highly valuable ω-halo enol ethers in excellent yields. Boosted by this method, we have prepared solasodine, an antitumor steroidal alkaloid, from diosgenin acetate in three steps with an overall yield of 50%.