Oxyberberine

Base Information

• Chemical Name: Oxyberberine
• CAS No.: 549-21-3
• Molecular Formula: C20H17 N O5
• Molecular Weight: 351.359
• NSC Number: 93138
• UNII: 4A04YKB3FT
• DSSTox Substance ID: DTXSID70203389
• Nikkaji Number: J11.558D
• Wikidata: Q27259321
• Metabolomics Workbench ID: 122322
• ChEMBL ID: CHEMBL11531
• Mol file: 549-21-3.mol

Synonyms:8-oxoberberine;JKL 1073A;JKL-1073A;JKL1073A

Chemical Property of Oxyberberine

Chemical Property:

• Vapor Pressure: 6.84E-15mmHg at 25°C
• Melting Point: 200-201℃
• Boiling Point: 611.5°Cat760mmHg
• PKA: -1.62±0.20(Predicted)
• Flash Point: 323.6°C
• PSA: 58.92000
• Density: 1.44g/cm³
• LogP: 2.97050
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 351.11067264
• Heavy Atom Count: 26
• Complexity: 607

Purity/Quality:

≥98% ^*data from raw suppliers

Berlambine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2=O)OCO5)OC
• Uses: Oxyberberin is a naturally occurring isoquinoline alkaloid shown to inhibit lipoxygenase and provide antioxidant activity.

Technology Process of Oxyberberine

There total 3 articles about Oxyberberine 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: 37.0%

berberine (2086-83-1) → oxyberberine (549-21-3) + 3-<3,4-dihydro-1-oxo-6,7-(methylenedioxy)-2H-isoquinolin-2-yl>-4,5-dimethoxy-1(3H)-isobenzofuranone (64939-64-6,66408-44-4) + 13-hydroxy-8-oxo-berberine (66408-27-3)

Guidance literature:

With iodosylbenzene; tetra-(n-butyl)ammonium iodide; In water; acetonitrile; at 50 ℃; for 18h;

DOI:10.1002/1522-2675(200204)85:4<1069::AID-HLCA1069>3.0.CO;2-I

Reference yield: 25.0%

canadine (29074-38-2) → oxyberberine (549-21-3) + berberine (2086-83-1) + 3-<3,4-dihydro-1-oxo-6,7-(methylenedioxy)-2H-isoquinolin-2-yl>-4,5-dimethoxy-1(3H)-isobenzofuranone (64939-64-6,66408-44-4)

Guidance literature:

With iodosylbenzene; tetra-(n-butyl)ammonium iodide; In water; acetonitrile; at 50 ℃; for 18h;

DOI:10.1002/1522-2675(200204)85:4<1069::AID-HLCA1069>3.0.CO;2-I

Reference yield:

Berberinol (10134-52-8) → oxyberberine (549-21-3) + 7,8-dihydroberberine (483-15-8)

Guidance literature:

With sodium hydroxide;

upstream raw materials:

Berberinol

berberine

canadine

Downstream raw materials:

berberine chloride

berberine

7,8-dihydroberberine

(RS)-6-[hydroxy-((SR)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-methyl]-2,3-dimethoxy-benzoic acid

Refernces