Berberrubine

Base Information

• Chemical Name: Berberrubine
• CAS No.: 17388-19-1
• Molecular Formula: C19H16NO4+
• Molecular Weight: 322.34
• UNII: ZZT5GBZ8KE
• DSSTox Substance ID: DTXSID90169675
• Wikidata: Q83039387
• Metabolomics Workbench ID: 126296
• ChEMBL ID: CHEMBL203135
• Mol file: 17388-19-1.mol

Synonyms:5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride;9-berberoline chloride;berberrubine;berberrubine chloride

Chemical Property of Berberrubine

Chemical Property:

• Melting Point: 255-259 °C
• PSA: 51.80000
• LogP: 2.79330
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 322.10793299
• Heavy Atom Count: 24
• Complexity: 474

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Berberrubine ^*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=CC5=C(C=C4CC3)OCO5)O

Technology Process of Berberrubine

There total 10 articles about Berberrubine 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: 98.4%

berberine chloride (633-65-8) → berberrubine (17388-19-1)

Guidance literature:

In N,N-dimethyl-formamide; for 0.25h; Wavelength; Microwave irradiation; Reflux;

DOI:10.1016/j.bmc.2017.08.013

Reference yield: 82.0%

berberine hydrochloride → berberrubine (17388-19-1)

Guidance literature:

With butanoic acid anhydride; pyridine hydrochloride; at 135 ℃; Inert atmosphere;

Reference yield: 76.0%

C28H29NO6 → berberrubine (17388-19-1)

Guidance literature:

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

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

upstream raw materials:

2-[(2-benzo[1,3]dioxol-5-yl-ethylamino)-methyl]-6-methoxy-phenol

Glyoxal

2-{[(E)-2-Benzo[1,3]dioxol-5-yl-ethylimino]-methyl}-6-methoxy-phenol

3,4-methylenedioxyphenylethylamine

Downstream raw materials:

berberrubine chloride