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5355-48-6

5355-48-6 Structure

5355-48-6 Structure
IdentificationBack Directory
[Name]

BETA-ACETYLDIGOXIN
[CAS]

5355-48-6
[Synonyms]

Digotab
digoridb
Cardioreg
Cor-puren
novodigal
B-ACETYLDIGOXIN
2-Acetyl Digoxin
β-Acetyl Digoxin
16’-acetyldigoxin
ACETYLDIGOXIN, B-
BETA-ACETYLDIGOXIN
4’’’-acetyldigoxin
Digoxin IMpurity J
-Acetyldigoxin CRS
acetate,beta-digoxi
acetyl-digoxin-beta
digoxin,4’’’-acetate
Digoxin EP Impurity J
BETA-ACETYLDIGOXIN USP/EP/BP
Acetyldigoxin research grade
hexamethyleneimine3,5-dinitrobenzoate
Digoxin Impurity 10(Digoxin EP Impurity J)
-acetyldigoxin for peak identification CRS
digoxigenin+zuckerkettewiebeiacetyl-digitoxin-alpha
3β-[[4-O-[4-O-(4-O-Acetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl)-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy]-12β,14-dihydroxy-5β-card-20(22)-enolide
3β-[4-O-[4-O-(4-O-Acetyl 2,6-dideoxy-β-D-ribo-hexopyranosyl)-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranosyloxy]-12β,14-dihydroxy-5β,14β-carda-20(22)-enolide
(3β,5β,12β)-3-[(O-4-O-Αcetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl-(14)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(14)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide
Card-20(22)-enolide, 3-[(O-4-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-, (3β,5β,12β)-
Card-20(22)-enolide, 3-((o-4-o-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.4)-o-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1.4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-
Card-20(22)-enolide, 3-[(O-4-O-acetyl-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-, (3beta,5beta,12beta)-
[EINECS(EC#)]

226-337-5
[Molecular Formula]

C43H66O15
[MDL Number]

MFCD00242932
[MOL File]

5355-48-6.mol
[Molecular Weight]

822.98
Chemical PropertiesBack Directory
[Melting point ]

271-273°C
[alpha ]

D20 +30.4° (c = 1.2 in alc)
[Boiling point ]

681.03°C (rough estimate)
[density ]

1.1139 (rough estimate)
[refractive index ]

1.5940 (estimate)
[storage temp. ]

-20°C Freezer
[solubility ]

Practically insoluble in water, sparingly soluble in methylene chloride, slightly soluble in ethanol (96 per cent).
[form ]

neat
[pka]

13.41±0.70(Predicted)
Safety DataBack Directory
[RIDADR ]

3249
[HazardClass ]

6.1(a)
[PackingGroup ]

II
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Originator]

Novodigal ,Asta Medica Arzneimittel
[Uses]

Digoxin derivative, a cardiotonic glycosides
[Definition]

ChEBI: Acetyldigoxin is a cardenolide glycoside.
[Manufacturing Process]

Dried crude product of the partial acetylation of digoxin (42 g) prepared from digitalis - is dissolved under reflux in acetone (480 ml) and n-hexane (2400 ml) is added to the solution with stirring. Fine crystals, which begin to separate immediately, are left at room temperature for 5 hours, then they are filtered with suction, washed with n-hexane and dried in vacuum at 40°C, yielding 32 g of crude β-acetyldigoxin (product 1). Product 1 (31 g) is dissolved under reflux in chloroform (500 ml) and toluene (2500 ml) is added thereto with stirring. The crystals, which separate after standing for 6 hours at room temperature, are filtered, washed with toluene and ether and dried in vacuum yielding 29 g of β-acetyldigoxin (product 2). MP: 249°-251°C.
The filtrate, which results from the separation of product 1, is evaparated to dryness in vacuum. The residue, which mainly contains unreacted digoxin, is purified by recrystallization from pyridine/ether/water (3.5:5:40) and repeatedly acetylated. It can then be recycled to produce more β- acetyldigoxin. The filtrate resulting from the separation of product 2 is evaporated to dryness. The resulting residue contains the di- and polyacetyl derivatives of digoxin, which are deacetylated to digoxin in a known manner and later is returned to a further acetylation process and can then be recycled to produce more β-acetyldigoxin. Beta-Acetyldigoxin may be prepared from digoxin, acetic acid and dicyclohexylcarbodiimide using the last one as a condensing agent.
[Therapeutic Function]

Cardiotonic
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