CID 5200420

Base Information

• Chemical Name: CID 5200420
• CAS No.: 126-17-0
• Molecular Formula: C27H43NO2
• Molecular Weight: 413.644
• European Community (EC) Number: 204-774-2
• Wikidata: Q27166949
• Wikipedia: Solasodine
• Mol file: 126-17-0.mol

Synonyms:solasodine;solasodine citrate, (3alpha,22alpha,25R)-isomer;solasodine, (3beta,22beta,25S)-isomer;tomatidenol

Chemical Property of CID 5200420

Chemical Property:

• Vapor Pressure: 8.21E-14mmHg at 25°C
• Melting Point: 284°C (dec.)(lit.)
• Refractive Index: 1.572
• Boiling Point: 537.9 °C at 760 mmHg
• PKA: pKb 6.30(at 25℃)
• Flash Point: 279.1 °C
• PSA: 41.49000
• Density: 1.12 g/cm³
• LogP: 5.61570
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble0.5mg/mL, clear (warmed)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 413.329379614
• Heavy Atom Count: 30
• Complexity: 749

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Solasodine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)O)C)C)C)NC1
• Isomeric SMILES: C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C)OC16CCC(CN6)C
• 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. antineoplastic, antiinflammatory A potentially useful precursor. Starting material for steroidal drugs.

Technology Process of CID 5200420

There total 65 articles about CID 5200420 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

solasodine-3β-acetate (1415-78-7,6159-99-5) → solasodine (126-17-0)

Guidance literature:

With water; sodium hydroxide; In methanol; dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2015.01.149

Reference yield: 88.0%

C43H61NO2Si → solasodine (126-17-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 70 ℃; Inert atmosphere;

Reference yield: 72.0%

C27H41N3O2 (1000612-48-5) → solasodine (126-17-0)

Guidance literature:

C₂₇H₄₁N₃O₂; With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 20 ℃; for 2h;

With sodium thiosulfate; In water; acetonitrile;

With sodium hydroxide; In water; acetonitrile; pH=9; diastereoselective reaction;

DOI:10.1016/j.tet.2011.06.058

upstream raw materials:

(25R)-3β-hydroxy-26-phthalimido-cholest-5-ene-16,22-dione

solamargine

solasonine

N-((25R)-3β,22-dihydroxy-(22ξH)-furost-5-en-26-yl)-phthalimide

Downstream raw materials:

C₄₉H₆₉NO₉

(22R,25R)-22,26-epiminocholest-5-ene-3β,16β-diol

pseudosolasodine diacetate

vespertilin

Refernces

• 1、 Kaneko,K.,Niitsu,K.. "-". . p. 299. Retrieved 1980.
• 2、 Uhle. "N-methylsolasodine.". . p. 792 - 797. Retrieved 1967.
• 3、 Uhle. "-". . . Retrieved 1961.
• 4、 Fayez,Saleh. "-". . p. 433,435. Retrieved 1967.
• 5、 Novruzov,Aslanov. "". . . Retrieved 1974.
• 6、 Wu, Jing-Jing,Gao, Ran,Shi, Yong,Tian, Wei-Sheng. "Direct amination of EF spiroketal in steroidal sapogenins: An efficient synthetic strategy and method for related alkaloids". . p. 6639 - 6642. Retrieved 2015.
• 7、 Rochelmeyer. "-". . p. 543. Retrieved 1936.
• 8、 Rozumek,Sander. "A contribution on chemical differentiation within species of Solanum dulcamara L". . p. 316 - 321. Retrieved 1967.
• 9、 Rowan, Daryl D.,Macdonald, Pauline E.,Skipp, Robert A.. "ANTIFUNGAL STRESS METABOLITES FROM SOLANUM AVICULARE". . p. 2102 - 2106. Retrieved 1983.
• 10、 Uhle. "-". . . Retrieved 1961.