56293-29-9

Basic information

• Product Name: ALOPERINE
• Synonyms: 6,13-METHANO-2H-DIPYRIDO[1,2-A:3',2'-E]AZOCINE,1,3,4,6,6A,7,8,9,10,12,13,13A-DODECAHYDRO-, [6R-(6,6A,13,13A)]-;ALLOPTERIN;ALOPERIN;ALOPERINE;(7-alpha,9-alpha)-9-de-2-piperidinyl-16,17-didehydro-ormosanine;16,17-didehydro-9-de-2-piperidinyl-,(7-alpha,9-alpha)-ormosanin;ALOPERIN:6,13-METHANO-2H-DIPYRIDO[1,2-A:3',2'-E]AZOCINE,1,3,4,6,6A,7,8,9,10,12,13,13A-DODECAHYDRO-, [6R-(6,6A,13,13A)]-,;6,13-Methano-2H-dipyrido[1,2-a:3',2'-e]azocine,1,3,4,6,6a,7,8,9,10,12,13,13a-dodecahydro-,[6R-(6α,6aβ,13α,13aα)]-
• CAS NO: 56293-29-9
• Molecular Formula: C₁₅H₂₄N₂
• Molecular Weight: 232.36
• EINECS: 300-006-2
• Product Categories: Alkaloids;Herb extract;Inhibitors
• Mol File: 56293-29-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 67-72 °C
• Boiling Point: 367.7 °C at 760 mmHg
• Flash Point: 155.8 °C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.31±0.20(Predicted)
• CAS DataBase Reference: ALOPERINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALOPERINE(56293-29-9)
• EPA Substance Registry System: ALOPERINE(56293-29-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RTECS: RM2979500
• Hazardous Substances Data: 56293-29-9(Hazardous Substances Data)

Usage

Description

The structure of this alkaloid from Sophora alopercuroides has recently been established from NMR and mass spectrometry.

Uses

Aloperine is a quinolizidine alkaloid with potential to treat inflammatory and allergic diseases.

References

Tolkachev et al., Khim. Prir. Soedin., 11,30 (1975)

InChI:InChI=1/C15H24N2/c1-2-7-17-10-13-9-12(14(17)5-1)8-11-4-3-6-16-15(11)13/h8,12-16H,1-7,9-10H2/t12?,13?,14-,15-/m1/s1

Upstream product

• 220384-61-2 (6R,7R,13R,14R,15S)-14-hydroxy-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one 
• 220384-57-6 (2R)-2-<(1E)-2-<1-(p-toluenesulfonyl)-1,4,5,6-tetrahydropyridin-3-yl>-vinyl>-piperidine-1-carboxylic acid tert-butyl ester 
• 220384-49-6 (2R)-2-vinylpiperidine-1-carboxylic acid tert-butyl ester 
• 220384-68-9 1-(p-toluenesulfonyl)-piperidin-3-ol 
• 792937-18-9 1-benzyl-2-oxo-6-piperidin-2-yl-1,2,3,4,6,7,8,8a-octahydro-quinoline-8-carboxylic acid methyl ester 
• 792937-19-0 1-benzyl-8-hydroxymethyl-6-piperidin-2-yl-1,2,3,4,6,7,8,8a-octahydro-1H-quinoline 
• 792937-20-3 N-benzyl-aloperine 
• 220384-63-4 (6R,7R,13S,15S)-1-(p-toluenesulfonyl)-tetradecahydro-6,13-methano-dipyrido<1,2-a;3',2'-e>azocin-12-one 
• 220384-55-4 1-(p-toluenesulfonyl)-piperidin-3-one 
• 220384-58-7 5-((E)-(R)-2-Piperidin-2-yl-vinyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine 
• 220384-56-5 trifluoromethanesulfonic acid 1-(p-toluenesulfonyl)-1,4,5,6-tetrahydro-pyridin-3-yl ester 

Relevant articles and documents

Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine

The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alco