(S)-Tetrahydrocolumbamine

Base Information

• Chemical Name: (S)-Tetrahydrocolumbamine
• CAS No.: 483-34-1
• Deprecated CAS: 483-33-0,1356-03-2,20504-94-3
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• Hs Code.: 2933990090
• UNII: MX470OL19D
• DSSTox Substance ID: DTXSID10964043
• Nikkaji Number: J34.147I
• Wikidata: Q27102599
• Pharos Ligand ID: W7UXB3QCKJD9
• Metabolomics Workbench ID: 51034
• ChEMBL ID: CHEMBL2334891
• Mol file: 483-34-1.mol

Synonyms:tetrahydro-columbamine;tetrahydrocolumbamine

Chemical Property of (S)-Tetrahydrocolumbamine

Chemical Property:

• Vapor Pressure: 1.14E-10mmHg at 25°C
• Melting Point: 239 - 240 °C
• Boiling Point: 501.2°C at 760 mmHg
• PKA: 10.18±0.20(Predicted)
• Flash Point: 256.9°C
• PSA: 51.16000
• Density: 1.29
• LogP: 3.01140
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated), Ethyl Acetate (Slightly, Heated)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 461

Purity/Quality:

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

(-)-Isocorypalmine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)OC
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)OC
• Description: This Menispermaceous alkaloid is found in the EtOH extract of Bornean Tino_x0002_miscium petiolare and crystallizes as colourless crystals from Me2CO. The 0- methyl derivative is identical with (-)-Tetrahydropalmatine, m.p. 141-2°C.
• Uses: A metabolite of the isoquinoline alkaloid biosynthesis pathway.

Technology Process of (S)-Tetrahydrocolumbamine

There total 46 articles about (S)-Tetrahydrocolumbamine 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: 81.0%

(S)-2-benzyloxy-3,9,10-trimethoxytetrahydroprotoberberine (1422431-55-7) → (-)-isocorypalmine (6487-33-8,6989-84-0,53447-14-6,483-34-1)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 2h; Reflux;

DOI:10.1016/j.bmc.2012.12.016

Reference yield:

tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8) → (-)-isocorypalmine (6487-33-8,6989-84-0,53447-14-6,483-34-1)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 0.416667h;

Reference yield:

tetrahydropalmatine (483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8) → (-)-isocorypalmine (6487-33-8,6989-84-0,53447-14-6,483-34-1) + (S)-scoulerine (605-34-5,6451-72-5,6451-73-6,6507-34-2)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 1h;

DOI:10.3390/molecules13092303

upstream raw materials:

columbamine

2-hydroxy-3-methoxy-9,10-dimethoxyprotoberberine iodide

diazomethane

(+/-)-tetrahydropalmatine

Downstream raw materials:

columbamine

canadine

tetrahydropalmatine

3,4-dimethoxy-phthalic acid

Refernces

• 1、 Lee, David Y.W.,Liu, Jing,Zhang, Shuzhen,Huang, Peng,Liu-Chen, Lee-Yuan. "Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors". . p. 1437 - 1440. Retrieved 2017/03/08.
• 2、 Gadhiya, Satishkumar,Madapa, Sudharshan,Kurtzman, Thomas,Alberts, Ian L.,Ramsey, Steven,Pillarsetty, Nagavara-Kishore,Kalidindi, Teja,Harding, Wayne W.. "Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity". . p. 2060 - 2071. Retrieved 2016/04/20.