1111-39-3

Basic information

• Product Name: ACETYLDIGITOXIN
• Synonyms: acetate,alpha-digitoxi;acetyl-digitoxin-alpha;acylanid;adicin;alpha-acetyldigitoxin;ACETYLDIGITOXIN;3'''-Acetyldigitoxin;3β-[[4-O-[4-O-(3-O-Acetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl)-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy]-14-hydroxy-5β-card-20(22)-enolide
• CAS NO: 1111-39-3
• Molecular Formula: C₄₃H₆₆O₁₄
• Molecular Weight: 806.98
• EINECS: 214-178-4
• Mol File: 1111-39-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 217-221°
• Boiling Point: 673.84°C (rough estimate)
• Flash Point: 265ºC
• Appearance: /
• Density: 1.1009 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6130 (estimate)
• CAS DataBase Reference: ACETYLDIGITOXIN(CAS DataBase Reference)
• NIST Chemistry Reference: ACETYLDIGITOXIN(1111-39-3)
• EPA Substance Registry System: ACETYLDIGITOXIN(1111-39-3)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 1111-39-3(Hazardous Substances Data)

Usage

Originator

Acylanid ,Sandoz ,US ,1954

Manufacturing Process

Acetyldigitoxin-α can be obtained from acetyldigitoxin-β by heating it in an anhydrous or aqueous organic solvent at neutral, weakly acid or weakly alkaline pH, i.e., at a pH range from about 3.5 to about 8. The acetylidigitoxin-β used for this purpose is a cardiac glycoside which can be obtained either by splitting off the glucose residue from lanatoside A, or by extraction of the leaves of Digitalis ferrugines. It is composed of the aglycone digitoxigenin and 3 molecules of digitoxose, to one of which an acetyl group is attached. Acetyldigitoxin-α, obtained from acetyldigitoxin-β by rearrangement, differs from the latter in the position of the acetyl group. The process may be carried out, for example, in the following manner: A solution of acetyldigitoxin-β in a suitable solvent, such as methanol, is boiled under reflux and then diluted with water. The unchanged acetyldigitoxin-β, which crystallizes out first, is filtered off and can again be submitted to the same process. On concentrating the filtrate, acetyldigitoxin-α separates out in crystalline form and after filtering off and recrystallizing is obtained in a pure state. The acetyldigitoxin-α crystallizes from aqueous methanol in platelets melting at 217-221°C.

Brand name

Acylanid (Novartis).

Therapeutic Function

Cardiotonic

Purification Methods

-Acetyldigitoxin is obtained from the commercial mixture [ : (2:1)] [25395-32-8]. The form is obtained from the form by heating in anhydrous or aqueous organic solvent (e.g. aqueous MeOH) at pH 3.5—8. It crystallises from MeOH as plates, CHCl3/Et2O or Me2CO/Et2O. At 20o 1g dissolves in 16mL of MeOH, 66mL of Me2CO and ~880mL of EtOAc. [Stoll & Kreis Helv Chim Acta 35 1318, 1322 1952, Beilstein 18 III/IV 1479.] It is a cardenolide.C5128

InChI:InChI=1/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1

Upstream product

• 25876-27-1 3',4'-di-O-acetyl digitoxin 
• 110-86-1 pyridine 
• 71-63-6 digitoxin 

Downstream Products

• 4442-17-5 3-dehydrodigoxigenin 
• 1672-46-4 digoxigenin 
• 71-63-6 digitoxin 
• 2053-00-1 D-digitoxose 
• 143-62-4 Digitoxigenin 

Related news

NOTESAcetyldigoxin and ACETYLDIGITOXIN (cas 1111-39-3) from Digitalis lanata08/13/2019

This paper describes the ready separation of acetyldigoxin from acetyldigitoxin when these secondary glycosides are isolated in combination from Digitalis lanata, fresh or dried, containing the maximum amounts of the native glycosides. The initial primary extract used 35% aqueous methanol and en...detailed

Relevant articles and documents

Selective enzymatic transformation of lanatoside A

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Uses of ouabain and ouabain-like molecules in apoptosis related pathologies

Longterm elevation of the intracellular Na+/K+ratio inhibits macromolecule synthesis and proliferation in the majority of cell types studied so far, including vascular smooth muscle cells (VSMC). We report here that inhibition of the Na+,K+pump in VSMC by ouabain or 1 hour preincubation in K+-depleted medium attenuated apoptosis triggered by serum withdrawal, staurosporine or okadaic acid. In the absence of ouabain, both DNA degradation and caspase-3 activation in VSMC undergoing apoptosis were insensitive to modification of the extracellular Na+/K+ratio as well as to hyperosmotic cell shrinkage. In contrast, protection of VSMC from apoptosis by ouabain was abolished under equimolar substitution of Na+owith K+o, showing that the anti apoptotic action of Na+,K+pump inhibition was caused by inversion of the intracellular Na+/K+ratio. Unlike VSMC, the same level of increment of the [Na+]i/[K+]iratio caused by 2 hours preincubation of Jurkat cells with ouabain did not affect chromatin cleavage and caspase-3 activity triggered by treatment with Fas ligand, staurosporine or hyperosmotic shrinkage. Thus, our results show for the first time that similarly to cell proliferation, maintenance of a physiologically low intracellular Na+/K+ratio is required for progression of VSMC apoptosis.