549-21-3

Basic information

• Product Name: BERLAMBINE
• Synonyms: OXYBERBERIN;BERLAMBINE;13,13a-didehydro-9,10-dimethoxy-2,3-(methylenedioxy)-8-berbinon;8-oxyberberine;9,10-dimethoxy-2,3-(methylenedioxy)-13,13a-didehydro-8-berbinone;ketoberberine;5,6-Dihydro-9,10-dimethoxy-8H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-8-one;9,10-Dimethoxy-5,6-dihydro-8H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine-8-one
• CAS NO: 549-21-3
• Molecular Formula: C₂₀H₁₇NO₅
• Molecular Weight: 351.35
• Product Categories: Alkaloids
• Mol File: 549-21-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 200-201℃
• Boiling Point: 611.5°Cat760mmHg
• Flash Point: 323.6°C
• Appearance: /
• Density: 1.44±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 6.84E-15mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -1.62±0.20(Predicted)
• CAS DataBase Reference: BERLAMBINE(CAS DataBase Reference)
• NIST Chemistry Reference: BERLAMBINE(549-21-3)
• EPA Substance Registry System: BERLAMBINE(549-21-3)

Safety Data

• Hazardous Substances Data: 549-21-3(Hazardous Substances Data)

Usage

Uses

Oxyberberin is a naturally occurring isoquinoline alkaloid shown to inhibit lipoxygenase and provide antioxidant activity.

InChI:InChI=1/C20H17NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9H,5-6,10H2,1-2H3

Upstream product

• 10134-52-8 Berberinol 
• 2086-83-1 berberine 
• 29074-38-2 canadine 

Downstream Products

• 29580-82-3 8-oxyberberrubine 
• 71700-15-7 12b-hydroxy-9,10-dimethoxy-5H-[1,3]dioxolo[4'',5'':4',5']benzo[1',2':4,5]azepino[2,1-a]isoindole-8,13(6H,12bH)-dione 
• 71266-76-7 8-Canadinylessigsaeure 
• 71266-74-5 (9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-ylidene)-p-tolyl-amine 
• 66392-97-0 (9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-ylidene)-malononitrile 
• 71266-73-4 (9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-ylidene)-phenyl-amine 
• 71266-78-9 8,8-Diethyldihydroberberin 
• 71266-91-6 Ethyl 8-berberinylidenacetoacetat 
• 71266-75-6 8-Berberinylessigsaeure 
• 71266-80-3 8-benzyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium; bromide 
• 61065-16-5 8-benzylcanadine 
• 66408-36-4 (+/-)-β-Norhydrastin 
• 66408-39-7 (RS)-6-[hydroxy-((SR)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-methyl]-2,3-dimethoxy-benzoic acid 
• 483-15-8 7,8-dihydroberberine 

Relevant articles and documents

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

Oxidation of N-methyltetrahydroisoquinolines with iodosylbenzene in the presence of a catalytic amount of tetrabutylammonium iodide in various solvents afforded N-methyl-2H-3,4-dihydroisoquinol-1-ones in almost quantitative yields. The application of this finding to the oxidation of other isoquinolines, including tetrahydroisoquinolines, lycorine diacetate, and benzyltetrahydroisoquinolines, also afforded the corresponding lactams in good yields, however, accompanied by a few minor byproducts. Under similar conditions, tetrahydroberberine gave a rearranged compound, berberal, as the major product, accompanied by 8-oxoberberine and berberine.