16479-50-8

Basic information

• Product Name: (3beta,5beta,8xi,9xi)-3-{[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide
• Synonyms: card-20(22)-enolide, 3-[[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy]-14-hydroxy-, (3beta,5beta,8xi,9xi)-
• CAS NO: 16479-50-8
• Molecular Formula: C₃₅H₅₄O₁₀
• Molecular Weight: 634.7973
• EINECS: 240-533-8
• Mol File: 16479-50-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 794.1°C at 760 mmHg
• Flash Point: 246.7°C
• Density: 1.3g/cm³
• Vapor Pressure: 3.71E-29mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: (3beta,5beta,8xi,9xi)-3-{[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,5beta,8xi,9xi)-3-{[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide(16479-50-8)
• EPA Substance Registry System: (3beta,5beta,8xi,9xi)-3-{[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide(16479-50-8)

Safety Data

• Hazardous Substances Data: 16479-50-8(Hazardous Substances Data)

Usage

Description

(3beta,5beta,8xi,9xi)-3-[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy-14-hydroxycard-20(22)-enolide is a complex cardenolide molecule with a steroid backbone. It features various sugar residues, specifically 2,6-dideoxy-beta-D-ribo-hexopyranosyl groups, attached to the steroid core and a hydroxyl group at position 14 of the steroid structure. This naturally occurring organic compound is known for its potential pharmaceutical properties, particularly in the treatment of heart conditions.

Uses

Used in Pharmaceutical Industry:
(3beta,5beta,8xi,9xi)-3-[2,6-dideoxy-4-O-(2,6-dideoxy-beta-D-ribo-hexopyranosyl)-beta-D-ribo-hexopyranosyl]oxy-14-hydroxycard-20(22)-enolide is used as a pharmaceutical compound for its potential heart condition treatment. Its unique structure and properties make it a promising candidate for developing new drugs to address various cardiac disorders.

Upstream product

• 912454-95-6 digitoxigen 3-O-acetyl-2,6-dideoxy-4-O-((2'R,6'R)-3',6'-dihydro-6'-methyl-2H-pyran-2'-yl)-β-D-ribo-hexopyranoside 
• 30788-61-5 digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside) 
• 71-63-6 digitoxin 

Downstream Products

• 18404-43-8 evatromonoside 

Relevant articles and documents

Production of the Cytotoxic Cardenolide Glucoevatromonoside by Semisynthesis and Biotransformation of Evatromonoside by a Digitalis lanata Cell Culture

Recent studies demonstrate that cardiac glycosides, known to inhibit Na + /K + -ATPase in humans, have increased susceptibility to cancer cells that can be used in tumor therapy. One of the most promising candidates identified so far is glucoevatromonoside, which can be isolated from the endangered species Digitalis mariana ssp. heywoodii. Due to its complex structure, glucoevatromonoside cannot be obtained economically by total chemical synthesis. Here we describe two methods for glucoevatromonoside production, both using evatromonoside obtained by chemical degradation of digitoxin as the precursor. 1) Catalyst-controlled, regioselective glycosylation of evatromonoside to glucoevatromonoside using 2,3,4,6-tetra- O -acetyl- α -D-glucopyranosyl bromide as the sugar donor and 2-aminoethyldiphenylborinate as the catalyst resulted in an overall 30% yield. 2) Biotransformation of evatromonoside using Digitalis lanata plant cell suspension cultures was less efficient and resulted only in overall 18% pure product. Structural proof of products has been provided by extensive NMR data. Glucoevatromonoside and its non-natural 1-3 linked isomer neo-glucoevatromonoside obtained by semisynthesis were evaluated against renal cell carcinoma and prostate cancer cell lines.

A direct comparison of the anticancer activities of digitoxin MeON-Neoglycosides and O-Glycosides

Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis.

Thermal Degradation of Glycosides, VI - Hydrothermolysis of Cardenolide and Flavonoid Glycosides

The hydrothermolysis of cardenolide and flavonoid glycosides is described.On heating with water or water/dioxane, cardenolide (1, 5, 11) and flavonoid glycosides (16, 20, 23, 27) are converted into their genuine aglycones and partially hydrolyzed products, together with saccharide components.Meanwhile, the glycosidic linkage of 2-deoxy sugar moieties in cardenolide glycosides is more readily cleaved than that of the common sugar moieties by means of hydrothermolysis.Therefore, hydrothermolysis of the uzarigenin triglycoside (13), bearing a 2-deoxy sugar moiety whichis directly attached to the aglycone, leads to selective cleavage of the sugar-aglycone linkage.The hydrothermolyzed products have been isolated by chromatography and their structures elucidated by spectroscopic methods. Key Words: Thermolysis / Degradation, thermal / Carbohydrates / Glycosides / Cardenolides / Steroids / Flavonoids