LANATOSIDE C

LANATOSIDE C Basic information
Product Name:LANATOSIDE C
Synonyms:LANATOSIDE C;20(22),5BETA-CARDENOLID-3BETA,12BETA,14BETA-TRIOL 3BETA-O-BETA-D-GLUCOPYRANOSYL-(1->4)-O-BETA-D-[3-O-ACETYLDIGITOXOPYRANOSYL]-(1->4)-O-BETA-D-DIGITOXOPYRANOSIDE-(1->4)-O-BETA-D-DIGITOXOPYRANOSIDE;Lanatoside C (Digoxin Impurity H);cedilanid;digilanidc;digilanidec;Digoxin EP Impurity H;Digoxin Impurity 8(Digoxin EP Impurity H)
CAS:17575-22-3
MF:C49H76O20
MW:985.12
EINECS:241-546-1
Product Categories:Cardioglycosides & Glycosides;Carbohydrates;Carbohydrates A to;Carbohydrates H-LBiochemicals and Reagents;Oligosaccharide;Intermediates & Fine Chemicals;Oligosaccharides;Pharmaceuticals;Steroids;DIFFERIN
Mol File:17575-22-3.mol
LANATOSIDE C Structure
LANATOSIDE C Chemical Properties
Melting point 272-274°C
alpha D20 +33.4 to +33.7° (200 mg dry weight in 10 ml alcohol)
Boiling point 741.7°C (rough estimate)
density 1.42±0.1 g/cm3 (20 ºC 760 Torr)
refractive index 1.7630 (estimate)
storage temp. -20°C
solubility DMSO:50.0(Max Conc. mg/mL);50.75(Max Conc. mM)
Ethanol:2.0(Max Conc. mg/mL);2.03(Max Conc. mM)
pka12.89±0.70(Predicted)
form Solid
color White to Off-White
Stability:Hygroscopic
LogP0.070
Safety Information
Hazard Codes T
Risk Statements 23/24/25
Safety Statements 36/37/39-45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS OE2100000
MSDS Information
LANATOSIDE C Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorLanatozid C,Biofarm
Usesanti-acne
UsesGlycosides
Manufacturing Process2000 parts of dry leaves of digitalis lanata are finely ground with 500 parts of sodium chloride, they are then wetted with 1000 parts of water and extracted with 30,000 parts of chloroform. The filtered extract is completely evaporated in vacuum at a low temperature and to the remaining residue are added 1000 parts of dry ether and the whole mixture is left under the ether until the thick viscous mass has been transformed into a hard body. The ether is then poured away and the residue is digested with 1000 parts of ether for about 2 hours under a reflux condenser. After cooling down the mixture, it is filtered, and the residue obtained, which is now in form of a brittle mass, which is then dried in vacuum in order to completely eliminate the remaining ether present, and pulverized. The pulverized mass is advantageously subjected once more to the treatment with ether. The yellow greenish powder thus obtained is then dissolved in 1000 parts of methyl alcohol and to the solution, so obtained a fine suspension of 30 parts lead hydroxide in 1000 parts water is added with stirring. The solution obtained is neutralized, stirred for about 2 hours, andfiltered, and the clear yellowish filtrate is preferably treated again with a small quantity of tannin precipitating substance. The clear filtrate thus obtained is concentrated in vacuum at a low temperature to about 200 parts, whereby the difficultly soluble portion of the glucoside mixture precipitates. The solution is then filtered. The precipitate is dissolved in a small quantity of methyl alcohol and is treated with a small quantity of water whereby the new product begins to precipitate in a crystalline form. By repeated crystallization from methyl alcohol, without addition of water, the glucoside may be obtained in the form of a perfectly pure compound; it does not change its properties even on further recrystallization. The glucoside, freshly crystallized from methyl alcohol and dried in vacuo, had MP: 248°C with decomposition, when heated rapidly. At 230°-235°C, the substance begins to sinter and becomes quite soft; the melting point, therefore, is not well defined.
Therapeutic FunctionCardiotonic
Purification MethodsCrystallise lanatoside C from MeOH. Its solubility is : 1/17000 (H2O), 1/45 (EtOH) and 1/1500-2000 (CHCl3). [Stoll et al. Helv Chim Acta 16 1049 1933, Stoll & Kreis Helv Chim Acta 35 1318 1952, Okada et al. Chem Pharm Bull Jpn 23 2039 1975, Beilstein 18 III/IV 2455.] It is cardiotonic.
LANATOSIDE C Preparation Products And Raw materials
Raw materialsTANNIC ACID-->LEAD HYDROXIDE
Ramnodigin ACETYLDIGITOXIN DIGOXIGENIN ALPHA-ACETYLDIGOXIN lanatoside D DIGOXIN digoxigenin-mono(digitoxoside) LANATOSIDE C K-STROPHANTHIN ABC lanatoside complex LANATOSIDE B Digitoxin STROPHANTHIN, g-(RG) A-METHYLDIGOXIN deacetyl-lanatosid Metildigoxin DIGITOXIGENIN LANATOSIDE A

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