25817-75-8

Basic information

• Product Name: (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide
• CAS NO: 25817-75-8
• Molecular Formula: C₂₉H₄₄O₁₀
• Molecular Weight: 552.6537
• Mol File: 25817-75-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 771.1°C at 760 mmHg
• Flash Point: 251.3°C
• Density: 1.41g/cm³
• Vapor Pressure: 1.88E-27mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide(25817-75-8)
• EPA Substance Registry System: (3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide(25817-75-8)

Safety Data

• Hazardous Substances Data: 25817-75-8(Hazardous Substances Data)

Usage

Description

(3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide is a cardenolide, a type of steroid found in certain plants. It consists of a steroid core structure with a sugar molecule attached to it. The specific arrangement of hydroxyl groups and sugar moieties on the steroid core gives it its unique pharmacological properties. Cardenolides are known for their ability to inhibit the sodium-potassium pump in cells, leading to increased levels of sodium inside the cell and resulting in various physiological effects, including increased contractility of the heart muscle.

Uses

Used in Pharmaceutical Industry:
(3beta,5beta,8xi,9xi,12beta)-3-(beta-D-glycero-hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide is used as a potential medical treatment for heart conditions. Its ability to inhibit the sodium-potassium pump in cells leads to increased contractility of the heart muscle, making it a promising candidate for the treatment of certain cardiac conditions. Further research and development are needed to fully understand its therapeutic potential and optimize its use in medical applications.

Upstream product

• 133-89-1 UDP-glucose 
• 1672-46-4 digoxigenin 
• 2280-44-6 D-Glucose 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 79317-29-6 digoxigenin 3β-β-D-glucoside tetraacetate 

Relevant articles and documents

UGT74AN1, a Permissive Glycosyltransferase from Asclepias curassavica for the Regiospecific Steroid 3-O-Glycosylation

A permissive steroid glycosyltransferase (UGT74AN1) from Asclepias curassavica exhibited robust capabilities for the regiospecific C3 glycosylation of cardiotonic steroids and C21 steroid precursors, and unprecedented promiscuity toward 53 structurally diverse natural and unnatural compounds to form O-, N-, and S-glycosides, along with the catalytic reversibility for a one-pot transglycosylation reaction. These findings highlight UGT74AN1 as the first regiospecific catalyst for cardiotonic steroid C3 glycosylation and exhibit significant potential for glycosylation of diverse bioactive molecules in drug discovery.

Cardenolide analogues. 11. Improved method for the use of Fetizon's reagent in the synthesis of cardiac glycosides

An improved procedure has been developed for preparing glycosides of cardenolide genins. The method uses specially prepared Fetizon's reagent as catalyst, combined, in most cases, with mercuric cyanide and mercuric bromide. In the presence of this catalyst, genins react readily, at room temperature, with per-acetylated 1-bromo-sugars to give the acetylated glycosides in high yield with little or no side reaction. The reaction proceeds almost to completion in 30 to 60 min. The free glycoside is obtained by mild deacetylation using triethylamine/methanol/water (20:20:1) at room temperature for 72 h. Proof of structure was obtained using chemical ionization mass spectrometry, NMR spectroscopy and comparison of physical constants with published data. The compounds were tested for inotropic activity using the isolated guinea pig atrium.