Tabersonine

Base Information

• Chemical Name: Tabersonine
• CAS No.: 4429-63-4
• Molecular Formula: C21H24N2O2
• Molecular Weight: 336.434
• European Community (EC) Number: 224-615-0
• UNII: MN955K48NB
• DSSTox Substance ID: DTXSID30196102
• Nikkaji Number: J62.335K
• Wikipedia: Tabersonine
• Wikidata: Q21099578
• Metabolomics Workbench ID: 50639
• ChEMBL ID: CHEMBL2011511
• Mol file: 4429-63-4.mol

Synonyms:tabersonine;tabersonine monoacetate

Chemical Property of Tabersonine

Chemical Property:

• Appearance/Colour: Yellow to brownish powder, pungent odour
• Vapor Pressure: 1.06E-09mmHg at 25°C
• Melting Point: 196 °C
• Refractive Index: 1.651
• Boiling Point: 488.7 °C at 760 mmHg
• PKA: 7?+-.0.60(Predicted)
• Flash Point: 249.4 °C
• PSA: 41.57000
• Density: 1.27 g/cm³
• LogP: 3.29710
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Ethyl Acetate (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 336.183778013
• Heavy Atom Count: 25
• Complexity: 669

Purity/Quality:

Tabersonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12CC(=C3C4(C1N(CC4)CC=C2)C5=CC=CC=C5N3)C(=O)OC
• Isomeric SMILES: CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)C5=CC=CC=C5N3)C(=O)OC
• Description: This alkaloid, found in Amsonia tabernaemontana, is difficult to obtain crystalline but the hydrochloride is readily crystallizable and has m.p. 195-6°C; [α]D - 310° (c 0.134, MeOH).
• Uses: (-)-Tabersonine is one of the terpenoid indole alkaloids (TIAs) from Catharanthus roseus. (-)-Tabersonine shows hypotensive activity, anti-tumor activity, hypoglycemic, diuretic activity.

Technology Process of Tabersonine

There total 35 articles about Tabersonine 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: 90.0%

19-Iodo-tabersonine (55856-70-7) → tabersonine (4429-63-4)

Guidance literature:

With sodium hydroxide; hydrogen; nickel; In methanol; at 0 ℃; for 0.0833333h;

Reference yield: 73.0%

methyl (2S,3aR,3a1S,10bR)-3a-ethyl-2-hydroxy-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate (62414-79-3) → tabersonine (4429-63-4)

Guidance literature:

With triphenylphosphine; In tetrachloromethane; acetonitrile; at 70 ℃; for 0.5h;

DOI:10.1016/S0040-4039(98)02667-7

Reference yield: 73.0%

methyl cyanoformate (17640-15-2) + (-)-1,2,14,15-tetradehydroaspidospermidine (32975-46-5) → tabersonine (4429-63-4)

Guidance literature:

(-)-1,2,14,15-tetradehydroaspidospermidine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1h; Inert atmosphere;

methyl cyanoformate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja408114u

upstream raw materials:

methyl (2S,3aR,3a1S,10bR)-3a-ethyl-2-hydroxy-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate

(S)-3a-Ethyl-2-hydroxy-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

19-Iodo-tabersonine

tabersonine N₄-oxide

Downstream raw materials:

voaphylline

lochnericine

vincamin

Refernces

• 1、 Kim, Joo-Young,Suhl, Chang-Heon,Lee, Joon-Ho,Cho, Cheon-Gyu. "Directed Fischer Indolization as an Approach to the Total Syntheses of (+)-Aspidospermidine and (-)-Tabersonine". . p. 6168 - 6171. Retrieved 2017.
• 2、 Farrow, Scott C.,Kamileen, Mohamed O.,Caputi, Lorenzo,Bussey, Kate,Mundy, Julia E. A.,McAtee, Rory C.,Stephenson, Corey R. J.,O'Connor, Sarah E.. "Biosynthesis of an Anti-Addiction Agent from the Iboga Plant". supporting information. p. 12979 - 12983. Retrieved 2019/08/26.