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| | BETA-ACETYLDIGOXIN Basic information |
| Product Name: | BETA-ACETYLDIGOXIN | | Synonyms: | novodigal;ACETYLDIGOXIN, B-;BETA-ACETYLDIGOXIN;B-ACETYLDIGOXIN;16’-acetyldigoxin;4’’’-acetyldigoxin;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)-;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 | | CAS: | 5355-48-6 | | MF: | C43H66O15 | | MW: | 822.98 | | EINECS: | 226-337-5 | | Product Categories: | Intermediates & Fine Chemicals;Oligosaccharides;Pharmaceuticals;Steroids | | Mol File: | 5355-48-6.mol |  |
| | BETA-ACETYLDIGOXIN Chemical Properties |
| 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) |
| RIDADR | 3249 | | HazardClass | 6.1(a) | | PackingGroup | II |
| | BETA-ACETYLDIGOXIN Usage And Synthesis |
| 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 |
| | BETA-ACETYLDIGOXIN Preparation Products And Raw materials |
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