Berbine

Base Information

• Chemical Name: Berbine
• CAS No.: 483-49-8
• Molecular Formula: C17H17N
• Molecular Weight: 235.3236
• UNII: 728C74FB5Z
• DSSTox Substance ID: DTXSID70870550
• Nikkaji Number: J31.841H
• Wikidata: Q27116529
• Mol file: 483-49-8.mol

Synonyms:berbine;tetrahydroprotoberberine

Chemical Property of Berbine

Chemical Property:

• Melting Point: 85°
• Boiling Point: 354.2°Cat760mmHg
• PKA: 7.85±0.20(Predicted)
• Flash Point: 151.8°C
• PSA: 3.24000
• Density: 1.17g/cm³
• LogP: 3.28000
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 235.136099547
• Heavy Atom Count: 18
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

BERBINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC3=CC=CC=C3CC2C4=CC=CC=C41

Technology Process of Berbine

There total 3 articles about Berbine 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: 47.0%

2-(o-((trimethylsilyl)methyl)benzyl)-3,4-dihydroisoquinolinium perchlorate (104330-76-9) → 2-(2-Trimethylsilanylmethyl-benzyl)-3,4-dihydro-2λ5-isoquinoline (116351-60-1) + (+-)-Berbin (483-49-8)

Guidance literature:

With cesium fluoride; In ethanol; for 12h; Heating;

DOI:10.1021/jo00256a038

Reference yield: 15.0%

2-(o-((trimethylsilyl)methyl)benzyl)-3,4-dihydroisoquinolinium perchlorate (104330-76-9) → 2-(2-methylbenzyl)-3,4-dihydroisoquinolin-1(2H)-one (116351-63-4) + (+-)-Berbin (483-49-8)

Guidance literature:

With cesium fluoride; In acetonitrile; for 12h; Heating;

DOI:10.1021/jo00256a038

Reference yield:

formic acid (64-18-6) + (-)-1-benzyl-1,2,3,4-tetrahydro-isoquinoline (19716-56-4,46808-99-5,57680-86-1,57680-87-2) → (-)-berbine (131-10-2,483-49-8,41173-75-5,107538-84-1)

Guidance literature:

Erhitzen des Reaktionsgemisches mit Phosphor(V)-oxid und Tetralin und Erwaermen des danach isolierten Reaktionsprodukts mit konz. wss. Salzsaeure und Zink_.;

upstream raw materials:

2-(o-((trimethylsilyl)methyl)benzyl)-3,4-dihydroisoquinolinium perchlorate

formic acid

(-)-1-benzyl-1,2,3,4-tetrahydro-isoquinoline

Refernces

Reactions of silyl enol ethers and lactone enolates with dimethyl(methylene)ammonium iodide. The bis α methylenation of pre vernolepin and pre vernomenin

10.1021/ja00437a058

The research focuses on the synthesis and reactions of various organic compounds, particularly those derived from Papaver somniferum and berberinoids. The purpose of the research was to explore the oxidation of the N-7 and C-8 bond in tetrahydroprotoberberine base (-)-scoulerine and its impact on the formation of phthalideisoquinoline derivatives, as well as to develop new pathways for the cleavage of the N-7 to C-8 bond in berberinoids. The study also investigated the use of di-methyl(methy1ene)ammonium iodide (7) in Mannich reactions and its potential in steroid synthesis, demonstrating the conversion of vicinal hydroxybutylrolactones into their α-methylene derivatives without the need for hydroxyl protection. The conclusions drawn from the research were that two pathways are available in the laboratory for the cleavage of the N-7 to C-8 bond of berberinoids, one involving the quinone methide route and the other through direct oxidation.

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