17059-16-4

Basic information

• Product Name: (3beta,5beta,8xi,9xi)-3-(beta-D-glycero-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide
• Synonyms: AL-235;AY 22248;Glucodigitoxigenin;Digitoxigenin glucoside;Digitoxigenin-3-β-D-glucoside
• CAS NO: 17059-16-4
• Molecular Formula: C₂₉H₄₄O₉
• Molecular Weight: 536.6543
• Mol File: 17059-16-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 735.2°C at 760 mmHg
• Flash Point: 239.3°C
• Density: 1.36g/cm³
• Vapor Pressure: 5.98E-25mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: (3beta,5beta,8xi,9xi)-3-(beta-D-glycero-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,5beta,8xi,9xi)-3-(beta-D-glycero-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide(17059-16-4)
• EPA Substance Registry System: (3beta,5beta,8xi,9xi)-3-(beta-D-glycero-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide(17059-16-4)

Safety Data

• Hazardous Substances Data: 17059-16-4(Hazardous Substances Data)

Upstream product

• 57-50-1 Sucrose 
• 143-62-4 (+)-digitoxigenin 
• 143-62-4 digitoxigenin 
• 41628-29-9 Uzarigenin 3-O-β-D-Glucopyranosyl (1-4)-β-D-Glucopyranoside 

Downstream Products

• 35068-75-8 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(10S,13R,14S)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 143-62-4 Uzarigenin 
• 35068-75-8 14-hydroxy-3β-(tetra-O-acetyl-β-D-glucopyranosyloxy)-5β,14β-card-20(22)-enolide 
• 492-61-5 β-D-glucose 
• 143-62-4 (+)-digitoxigenin 
• 1102-88-1 digitoxigenone 
• 808-19-5 digitoxigenin 3-acetate 
• 50-99-7 D-glucose 

Relevant articles and documents

Biotransformation of digitoxigenin by cultured Strophanthus hybrid cells

Hybrid cells between Strophanthus gratus and S. amboensis were obtained by electrofusion and confirmed to be hybrids through isozyme and RFLP analyses. Because a new and hybrid compound, 17βH-periplogenin β-D- glucoside, was isolated as a biotransformation product of digitoxigenin by the hybrid cells, isomerization of 17β-lactone ring on S. gratus and glucosylation on S. amboensis were demonstrated simultaneously as the biotransformation abilities in the hybrid cells. Moreover, the productivity of the hybrid compound was increased by raising the sucrose concentration.

BIOTRANSFORMATION OF DIGITOXIGENIN BY GINSENG HAIRY ROOT CULTURES

Five new compounds (three esters and two glycosides) and seven previously reported compounds were isolated as biotransformation products of digitoxigenin by ginseng hairy root cultures.The new esters and glycosides were elucidated as digitoxigenin stearate, digitoxigenin palmitate, digitoxigenin myristate, 3-epidigitoxigenin β-D-gentiobioside and digitoxigenin β-D-sophoroside using 1H and 13C NMR and FAB mass spectral data.Biotransformations involving esterification (of stearic acid, palmitic acid, myristic acid and lauric acid) and glycosylation (of gentiobiose and sophorose) of digitoxigenin have been demonstrated for the first time in the plant cell and tissue cultures.The hairy roots showed high glycosylation ability to the digitoxigenin molecule.

Potential anticancer agents. V. Cardiac glycosides of Asclepias albicans (Asclepiadaceae)

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