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

Description

BERLAMBINE is a naturally occurring isoquinoline alkaloid that has been identified for its potential biological activities, including the inhibition of lipoxygenase and antioxidant properties. It is derived from various plant sources and has garnered interest due to its potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
BERLAMBINE is used as a bioactive compound for its ability to inhibit lipoxygenase, an enzyme involved in various inflammatory processes. This inhibition can contribute to the development of anti-inflammatory drugs, which may be beneficial in treating conditions characterized by excessive inflammation.
Additionally, BERLAMBINE is used as an antioxidant agent for its capacity to neutralize harmful free radicals in the body. Antioxidants are essential in preventing oxidative stress and reducing the risk of various diseases, including cancer, cardiovascular diseases, and neurodegenerative disorders.

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.