56519-07-4

Basic information

• Product Name: (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde
• Synonyms: (-)-Akagerine;(3aS,αE)-α-Ethylidene-1,2,3,3a,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde;(αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde;Akagerine
• CAS NO: 56519-07-4
• Molecular Formula: C20H24N2O2
• Molecular Weight: 324.41676
• Mol File: 56519-07-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 541.3°Cat760mmHg
• Flash Point: 281.2°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.5E-12mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde(56519-07-4)
• EPA Substance Registry System: (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde(56519-07-4)

Safety Data

• Hazardous Substances Data: 56519-07-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H24N2O2/c1-3-13(12-23)14-10-18-20-16(8-9-21(18)2)15-6-4-5-7-17(15)22(20)19(24)11-14/h3-7,12,14,18-19,24H,8-11H2,1-2H3/b13-3-/t14-,18+,19+/m1/s1

Upstream product

• 116287-97-9 (-)-secologanin aglucone-O-silyl ether 
• 123828-68-2 palicoside 

Relevant articles and documents

Main glucosidase conversion products of the gluco-alkaloids dolichantoside and palicoside

The enzymatic glucose cleavage of palicoside revealed the biosynthetic pathway to akagerine, whereas the conversion of dolichantoside led to a new quaternary heteroyohimbine alkaloid named Nb-methyl-21-β-hydroxy-mayumbine. The hypothetical models of reactions occurring after the conversion of both substrates are proposed. Dolichantoside and palicoside, as well as Strychnos mellodora stem bark crude ethanol extract, exhibit significant antimycotic activity against human pathogens in presence of specific glucosidase.

First Enantioselective Synthesis of (-)-Akagerine by a Chemoenzymatic Approach

(-)-Akagerine (1) was synthesized in an efficient and stereocontrolled fashion from the readily available (1S,2R)-cyclohexenedimethanol monoacetate 4.Key steps were the cleavage of the C(17)/C(18) bond of a 14a and the regio- and stereoselective cyclizati