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)

pka

12.89±0.70(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

LogP

0.070

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

LANATOSIDE C Usage And Synthesis

Chemical Properties

White Solid

Originator

Lanatozid C,Biofarm

Uses

anti-acne

Uses

Glycosides

Manufacturing Process

2000 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 Function

Cardiotonic

Purification Methods

Crystallise 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(17575-22-3)Related Product Information

• LANATOSIDE B
• K-STROPHANTHIN
• DIGITOXIGENIN
• Metildigoxin
• deacetyl-lanatosid
• lanatoside D
• DIGOXIN
• ACETYLDIGITOXIN
• DIGOXIGENIN
• LANATOSIDE C
• Digitoxin
• LANATOSIDE A
• G-STROPHANTHIN
• 3-ACETYL STROPHANTHIDIN
• digoxigenin-mono(digitoxoside)
• A-METHYLDIGOXIN
• ALPHA-ACETYLDIGOXIN
• ABC lanatoside complex