Columbamine

Base Information

• Chemical Name: Columbamine
• CAS No.: 3621-36-1
• Molecular Formula: C20H20 N O4
• Molecular Weight: 338.383
• Hs Code.: 2933990090
• UNII: 7T4808FEJW
• DSSTox Substance ID: DTXSID80189766
• Nikkaji Number: J8.189B
• Wikipedia: Columbamine
• Wikidata: Q27098298
• Metabolomics Workbench ID: 133585
• ChEMBL ID: CHEMBL400345
• Mol file: 3621-36-1.mol

Synonyms:columbamine

Chemical Property of Columbamine

Chemical Property:

• Melting Point: 280-282℃ (methanol )
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 51.80000
• Density: g/cm³
• LogP: 3.08180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 338.13923312
• Heavy Atom Count: 25
• Complexity: 461

Purity/Quality:

≥98% ^*data from raw suppliers

Columbamine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)O)OC

Technology Process of Columbamine

There total 8 articles about Columbamine 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: 78.0%

C28H29NO6 → columbamine (3621-36-1)

Guidance literature:

C₂₈H₂₉NO₆; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

isocorypalmine (483-34-1,6487-33-8,6989-84-0,53447-14-6) → columbamine (3621-36-1)

Guidance literature:

With (S)-tetrahydroprotoberberine oxidase; tris hydrochloride; at 37 ℃; for 2h; pH=8.8; Enzymatic reaction;

DOI:10.1074/jbc.M112.420414

Reference yield:

C10H8ClNO2 → columbamine (3621-36-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / tetrahydrofuran / 65 °C

2.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C

3.2: 2 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; potassium carbonate; methanesulfonyl chloride; triethylamine; XPhos; In tetrahydrofuran; ethanol; dichloromethane; toluene;

upstream raw materials:

(-)-isocorypalmine

(S)-scoulerine

(+)-(S)-reticuline

isocorypalmine

Downstream raw materials:

isocorypalmine