Solanidine

Base Information

• Chemical Name: Solanidine
• CAS No.: 80-78-4
• Molecular Formula: C27H43 N O
• Molecular Weight: 397.645
• European Community (EC) Number: 201-309-5
• NSC Number: 76025
• UNII: W7801OHM8B
• DSSTox Substance ID: DTXSID701018960
• Nikkaji Number: J4.255B
• Wikipedia: Solanidine
• Wikidata: Q3489153
• Metabolomics Workbench ID: 35257
• ChEMBL ID: CHEMBL1980466
• Mol file: 80-78-4.mol

Synonyms:solanidine

Chemical Property of Solanidine

Chemical Property:

• Vapor Pressure: 3.13E-12mmHg at 25°C
• Melting Point: 212-214°C
• Boiling Point: 503.1°C at 760 mmHg
• Flash Point: 223.5°C
• PSA: 23.47000
• Density: 1.1g/cm³
• LogP: 5.59290
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 397.334464995
• Heavy Atom Count: 29
• Complexity: 715

Purity/Quality:

98%,99%, ^*data from raw suppliers

Solanidine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,Xn
• Statements: 23/24/25-53-22
• Safety Statements: 2-13-45-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CC=C6C5(CCC(C6)O)C)C)C
• Isomeric SMILES: C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O)C)C)C
• Uses: Soladine has been shown to display mutagenic properties in the liver, and is stored in the body for prolonged periods of time.

Technology Process of Solanidine

There total 40 articles about Solanidine 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: 99.0%

C43H61NOSi → solanidine (80-78-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 2h;

DOI:10.1021/acs.joc.7b01133

Reference yield: 73.0%

3β-Hydroxy-7'-oxo-3'α,6'α-dimethyl-1'αH,3aαH-indolizidino<1',2';16,17>androst-5-en (19330-95-1) → solanidine (80-78-4)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01320

Reference yield: 20.0%

C30H47NO5S (78720-01-1) → solanidine (80-78-4) + camtschatcanidine (78719-99-0) + camtschatcanidine monomesylate (78720-00-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 1h; Heating;

DOI:10.1016/0031-9422(81)85117-5

upstream raw materials:

solanidine 3-O-α-L-rhamnopyranosyl-(1<*>2)-O-<β-D-glucopyranosyl-(1<*>4)>-β-D-glucopyranoside

solanidine 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside

C₃₀H₄₇NO₅S

α-chaconine

Downstream raw materials:

solanidine β-D-galactopyranoside

3β(p-toluenesulfonyloxy)-22αH,25βH-solanid-5-en-3-ol

3α,5-cyclo-5α,22αH,25βH-solanidan-6β-ol

demissidine

Refernces

• 1、 Hou, Ling-Li,Shi, Yong,Zhang, Zhi-Dan,Wu, Jing-Jing,Yang, Qing-Xiong,Tian, Wei-Sheng. "Divergent Synthesis of Solanidine and 22-epi-Solanidine". . p. 7463 - 7469. Retrieved 2017.
• 2、 Zhang, Zhi-Dan,Shi, Yong,Wu, Jing-Jing,Lin, Jing-Rong,Tian, Wei-Sheng. "Synthesis of Demissidine and Solanidine". supporting information. p. 3038 - 3040. Retrieved 2016/07/06.