436-05-5

Basic information

• Product Name: CURINE
• Synonyms: L-BEBEERINE;CURINE;(-)-BEBEERINE;d-bebeerine;(1R)-6,6'-Dimethoxy-2,2'-dimethyltubocuraran-7',12'-diol;(1R,1'R)-6,6'-Dimethoxy-2,2'-dimethyltubocuraran-7',12'-diol;Aristolochine【C36 alkaloid】;13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido(3',2':14,15)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinoline-9,19-diol, 2,3,13A,14,15,16,25,25A-octahydro-18,29-dimethoxy-1,14-dimethyl-, (13ar,25ar)-
• CAS NO: 436-05-5
• Molecular Formula: C₃₆H₃₈N₂O₆
• Molecular Weight: 594.7
• EINECS: 207-109-4
• Mol File: 436-05-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 213°; mp 221° in vacuo; mp 161°
• Boiling Point: 647.35°C (rough estimate)
• Flash Point: 381.1 °C
• Appearance: /
• Density: 1.1774 (rough estimate)
• Vapor Pressure: 1.27E-20mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Very Slightly)
• PKA: 9.39±0.20(Predicted)
• CAS DataBase Reference: CURINE(CAS DataBase Reference)
• NIST Chemistry Reference: CURINE(436-05-5)
• EPA Substance Registry System: CURINE(436-05-5)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• RIDADR: UN 1544 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 436-05-5(Hazardous Substances Data)

Usage

Uses

l-Bebeerine is a bisbenzylisoqinoline alkaloid which displays anto-allergic properties. In addition, has been shown to arrest cell cycle activity and induce apoptosis.

InChI:InChI=1/C36H38N2O6/c1-37-13-11-23-18-31(41-3)32-20-26(23)27(37)15-21-5-8-25(9-6-21)43-36-34-24(19-33(42-4)35(36)40)12-14-38(2)28(34)16-22-7-10-29(39)30(17-22)44-32/h5-10,17-20,27-28,39-40H,11-16H2,1-4H3/t27-,28-/m1/s1

Upstream product

• 15357-92-3 6-methoxy-7-(benzyloxy)-3,4-dihydroisoquinoline 
• 123-11-5 4-methoxy-benzaldehyde 
• 156-38-7 4-hydroxyphenylacetate 
• 52336-73-9 7-(benzyloxy)-6-methoxy-2-methyl-3,4-dihydroisoquinolinium iodide 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 55803-41-3 N-formyl-2-[3-methoxy-4-(benzyloxy)phenyl]ethylamine 
• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 121-33-5 vanillin 
• 63909-38-6 1-(benzyloxy)-2-methoxy-4-[(E)-2-nitroethenyl]benzene 
• 115032-64-9 4-bromomethylphenyl methoxymethyl ether 
• 7212-39-7 (4-methoxymethoxyphenyl)methanol 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 

Downstream Products

• 100-09-4 4-methoxybenzoic acid 
• 1721-93-3 1-methylisoquinoline 
• 31944-97-5 chondrofoline 
• 99-50-3 3,4-Dihydroxybenzoic acid 

Relevant articles and documents

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine

Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.