77988-07-9

Basic information

• Product Name: Secologanin diMethyl acetal
• Synonyms: Secologanin diMethyl acetal
• CAS NO: 77988-07-9
• Molecular Formula: C19H30O11
• Molecular Weight: 434.4349
• Mol File: 77988-07-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 578.2°C at 760 mmHg
• Flash Point: 197°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 8.93E-16mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: Secologanin diMethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: Secologanin diMethyl acetal(77988-07-9)
• EPA Substance Registry System: Secologanin diMethyl acetal(77988-07-9)

Safety Data

• Hazardous Substances Data: 77988-07-9(Hazardous Substances Data)

Usage

Uses

Secologanin Acetal is obtained from the leaves of Davidia involucrata and displays neuritogenic activity in PC12h cells.

InChI:InChI=1/C19H30O11/c1-5-9-10(6-13(25-2)26-3)11(17(24)27-4)8-28-18(9)30-19-16(23)15(22)14(21)12(7-20)29-19/h5,8-10,12-16,18-23H,1,6-7H2,2-4H3/t9-,10+,12-,14-,15+,16-,18+,19+/m1/s1

Upstream product

• 67-56-1 methanol 
• 19351-63-4 secologanin 
• 1227940-10-4 hydracyanoside D 

Relevant articles and documents

Formation of trioxadamantane type aglucones of 3-methoxy secologanin derivatives

Acidic transformation of some 3,4-dihydro-3-substituted secologanin derivatives produced trioxadamantane type compounds. The formation of the bridged tricyclic products from monocyclic educts is interpreted as multistep hydrolysis and transacetalation accompanied by deglucosylation.

SELECTIVE TRANSFORMATIONS OF SECOLOGANIN: DIHYDROXYLATION

Sweroside tetraacetate ( 2b ) has been converted in high yield by osmylation to the epimeric glycols 3 and 4 ( R=H ) which have been separated.This reaction proceeds with high chemoselectivity for reaction at the vinyl side chain but with low stereoselectivity, leading to a small excess of the 3-R isomer.Secologanin derivatives appear to show a much lower chemoselectivity in this reaction, but the stereoselectivity is considerably higher, and opposite to that in the sweroside example.Conditions have been found for oxidizing the dimethylacetal 5b of secologanin tetraacetate in useful yields to the epimeric glycols 6 and 7 ( R=H ); in this reaction a large excess of the 3-S isomer is formed.The reasons for these differences in selectivity appear to be related to differences between the two series in conformational preference.