35068-75-8

Basic information

• Product Name: (3alpha,5beta,8xi,9xi)-14-hydroxy-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glycero-hexopyranosyl)oxy]card-20(22)-enolide
• CAS NO: 35068-75-8
• Molecular Formula: C₃₇H₅₂O₁₃
• Molecular Weight: 704.801
• Mol File: 35068-75-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 748.656°C at 760 mmHg
• Flash Point: 223.828°C
• Density: 1.3g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: (3alpha,5beta,8xi,9xi)-14-hydroxy-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glycero-hexopyranosyl)oxy]card-20(22)-enolide(CAS DataBase Reference)
• NIST Chemistry Reference: (3alpha,5beta,8xi,9xi)-14-hydroxy-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glycero-hexopyranosyl)oxy]card-20(22)-enolide(35068-75-8)
• EPA Substance Registry System: (3alpha,5beta,8xi,9xi)-14-hydroxy-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glycero-hexopyranosyl)oxy]card-20(22)-enolide(35068-75-8)

Safety Data

• Hazardous Substances Data: 35068-75-8(Hazardous Substances Data)

Upstream product

• 143-62-4 (+)-digitoxigenin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 6877-82-3 Desglucouzarin 
• 466-09-1 uzarigenine 
• 83-87-4 D-glucose pentaacetate 
• 17059-16-4 digitoxigenin 3-O-β-D-glucoside 

Relevant articles and documents

Synthesis of cardenolide glycosides and putative biosynthetic precursors of cardenolide glycosides

A rapid and efficient procedure for glycosylation of steroids was established using a modified Koenigs-Knorr procedure. Peracetylated β- glycosides were synthesized by reaction of cardenolides, various pregnanes and 23-nor-5,20(22)E-choldienic acid at room temperature with the peracetylated 1-bromo derivatives of D-glucose, D-galactose, D-fucose and cellobiose. Subsequent deprotection was performed by alkaline hydrolysis with sodium methoxide. Structures of the respective glycosides were established by NMR techniques. The complete protocol was shown to be non-destructive at all stages to the sugar moiety and the steroidal nucleus. The γ-unsaturated lactone ring of the cardenolides was shown to remain intact and no formation of C-14 unsaturated compounds was observed.

Cardiac glycosides: 2. Synthesis of glucose and galactose analogs.

Five cardioactive steroid genins 1a to 5a of widely varying C17 beta-side groups were converted by modified Koenigs-Knorr reactions into the corresponding beta-D-glucosides 1c to 5c and beta-D-galactosides 1e to 5e. The genins included digitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta-card-20-(22)-enolide, 1a); (20R)-20, 22-dihydrodigitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta, 20R-cardanolde, 2a); 3 beta, 14-dihydroxy-22-methylene-5 beta, 14 beta, 20S-cardanolide (3a); methyl 3 beta, 14-dihydroxy-5 beta, 14 beta-pregn-20(E)-ene-21-carboxylate (4a); and methyl 3 beta, 14-dihydroxy-21-methylene-5 beta, 14 beta-pregnane-21-carboxylate (5a).

BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL SUSPENSION CULTURES OF DIGITALIS PURPUREA

Digitoxigenin was oxidized to digitoxigenone which was reduced to epidigitoxigenin and then glucosylated to epidigitoxigenin glucoside by cell cultures of Digitalis purpurea.The epidigitoxigenin glucoside, together with digitoxigenone and epidigitoxigenin, was isolated in considerable amounts, whereas digitoxigenin glucoside could only be detected in low concentration.Furthermore, it was confirmed by TLC and HPLC that digitoxigenin was hydroxylated to periplogenin.Key Word Index-Digitalis purpurea; Scrophulariaceae; tissue cultures; biotransformation; hydroxylation; glucosylation; steroid; digitoxigenin; digitoxigenone; epidigitoxigenin; periplogenin; digitoxigenin glucoside; epidigitoxigenin glucoside.