| Identification | Back 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 Properties | Back 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) |
| Hazard Information | Back 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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