19-epi-Ajmalicine

Base Information

• Chemical Name: 19-epi-Ajmalicine
• CAS No.: 25532-45-0
• Molecular Formula: C21H24 N2 O3
• Molecular Weight: 352.433
• DSSTox Substance ID: DTXSID501316603
• Nikkaji Number: J393.324E
• Wikidata: Q27105363
• Pharos Ligand ID: 6YFNSKG3YKV2
• ChEMBL ID: CHEMBL2079609
• Mol file: 25532-45-0.mol

Synonyms:19-epiajmalicine;ajmalicine;ajmalicine hydrochloride;ajmalicine, (19alpha,20alpha)-isomer;ajmalicine, (19beta)-isomer;ajmalicine, (19beta,20alpha)-isomer;ajmalicine, (3-beta,19beta)-isomer;ajmalicine, (3beta,19alpha)-isomer;ajmalicine, (3beta,19alpha,20alpha)-isomer;ajmalicine, (hydrochloride(19beta,20alpha))-isomer;ajmalicine, hydrochloride(19alpha)-isomer;ajmalicine, PO4(19alpha)-isomer;akuammigine;delta-yohimbine;Lamuran;raubasine;raubasine HCl;raubasine hydrochloride;rauvasan;tetrahydro-alstonine;tetrahydroalstonine

Chemical Property of 19-epi-Ajmalicine

Chemical Property:

• Vapor Pressure: 4.47E-11mmHg at 25°C
• Boiling Point: 524°C at 760 mmHg
• Flash Point: 270.7°C
• PSA: 54.56000
• Density: 1.3g/cm³
• LogP: 3.11670
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 606

Purity/Quality:

99% ^*data from raw suppliers

Mayumbine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45
• Isomeric SMILES: C[C@@H]1[C@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45

Technology Process of 19-epi-Ajmalicine

There total 65 articles about 19-epi-Ajmalicine 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: 60.0%

C23H26N2O6 → (+)-rauniticine (483-03-4,483-04-5,642-17-1,5299-09-2,6474-90-4,6870-40-2,6884-17-9,20361-85-7,20361-86-8,24196-06-3,24196-08-5,24196-15-4,24196-16-5,25532-45-0,25532-46-1,112835-69-5,122441-12-7,132016-16-1)

Guidance literature:

C₂₃H₂₆N₂O₆; With methanol; sodium tetrahydroborate; at -10 ℃; for 0.5h; Inert atmosphere;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Reflux;

With methanol; potassium carbonate; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.chempr.2017.04.007

Reference yield:

<21α-2H>-geissoschizine → ajmalicine (483-04-5) + 19-Epiajmalicine (25532-45-0)

Guidance literature:

With nicotinamide adenine dinucleotide phosphate; NADPH; In water; cell-free extracts of C_. roseus cell suspension;

DOI:10.1016/S0040-4039(00)93646-3

Reference yield:

(Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate (439-66-7) → ajmalicine (483-04-5) + 19-Epiajmalicine (25532-45-0)

Guidance literature:

With nicotinamide adenine dinucleotide phosphate; NADPH; In water; cell-free extracts of C_. roseus cell suspension;

DOI:10.1016/S0040-4039(00)93646-3

upstream raw materials:

(Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate

tryptamine

serpentine

Downstream raw materials:

tetrahydroalstonine

Refernces

• 1、 Pfitzner, Artur,Stoeckigt, Joachim. "PARTIAL PURIFICATION AND CHARACTERIZATION OF GEISSOSCHIZINE DEHYDROGENASE FROM SUSPENSION CULTURES OF CATHARANTHUS ROSEUS". . p. 1585 - 1588. Retrieved 1982.
• 2、 Martin, Stephen F.,Benage, Brigitte,Geraci, Leo S.,Hunter, James E.,Mortimore, Michael. "Unified strategy for synthesis of indole and 2-oxindole alkaloids". . p. 6161 - 6171. Retrieved 2007/10/02.