CONVALLATOXIN

CONVALLATOXIN Basic information
Product Name:CONVALLATOXIN
Synonyms:STROPHANTHIN 3ALPHA-1-RHAMNOSIDE;STROPHANTHIDIN ALPHA-L-RHAMNOPYRANOSIDE;STROPHANTHIDIN A-L-RHAMNOPYRANOSIDE;CORGLYKON;CONVALLATOXIN;20(22),5BETA-CARDENOLID-19-AL-3BETA,5BETA,14BETA-TRIOL-3BETA-D-[A-1-RHAMNOPYRANOSIDE];Convallatoxine;Strophanthidin α-L-rhamnopyranoside, 3β,5α,14-Trihydroxy-19-oxo-5β,20(22)-cardenolide 3-(6-deoxy-α-L-mannopyranoside)
CAS:508-75-8
MF:C29H42O10
MW:550.64
EINECS:208-086-3
Product Categories:Aldehydes;Building Blocks;C13-C60;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
Mol File:508-75-8.mol
CONVALLATOXIN Structure
CONVALLATOXIN Chemical Properties
Melting point 238-239℃ (water )
alpha D22 -1.7 ± 3° (c = 0.65 in methanol); D25 -9.4 ± 3° (c = 0.72 in dioxane)
Boiling point 542°C (rough estimate)
density 1.41±0.1 g/cm3 (20 ºC 760 Torr)
refractive index 1.5376 (estimate)
storage temp. Store at -20°C
solubility Soluble in DMSO
form Solid
pka13.04±0.70(Predicted)
color White to Off-White
Merck 13,2538
Stability:Hygroscopic
Safety Information
RIDADR 3249
WGK Germany 2
RTECS GL4025000
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data508-75-8(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): 10.0 i.p., 16.0 i.v. (Frster)
MSDS Information
ProviderLanguage
SigmaAldrich English
CONVALLATOXIN Usage And Synthesis
OriginatorConvallatoxin,C-Strong Co., Ltd.
UsesConvallatoxin is a cardenolide that is used in the treatment of congestive heart failure. It may also be used in the treatment of tumor cells at nanomolar concentrations due to its anti-proliferative effects
DefinitionChEBI: A cardenolide glycoside that consists of strophanthidin having a 6-deoxy-alpha-L-mannopyranosyl (L-rhamnosyl) group attached at position 3.
Manufacturing Process1 part of grinded flowers Convallaria majalis and 12 parts of water was stirred for 15 hours at ambient temperature. After a filtration and washing with water, a clear brown filtrate was mixed with a concentrate solution of lead acetate. A lead consisted precipitate was filtered off and sodium phosphate was added to filtrate for removing the remaining lead. The solution was filtered again and 0.5 - 0.6 parts of a coal was added and the mixture was stirred for 3 hours at ambient temperature. The coal was filtered off, washed with a little water and dried at 30°-40°C. A hot CHCl3 was added to dry coal adsorbent. CHCl3 was distilled off to dryness in vacuum. The residue was dissolved in a little methanol and the obtained solution was shook 3 times with 2 volumes of petrol ether and then distilled to dryness in vacuum. This product was dissolved in minimum absolute ethanol and added to 10 volumes of dry ether. The formed precipitate was filtered and washed with ether to
give the glycoside as a gray powder. It was crystallized from diluted ethanol as colorless needles.
Therapeutic FunctionCardiotonic
Purification MethodsCrystallise convallatoxin from EtOAc, CHCl3/EtOH (9:1) or MeOH/Et2O. The tetraacetate has m 238-242o (from MeOH/Et2O), [] D 25 -5o (CHCl3). [Reyle et al. Helv Chim Acta 33 1541 1950, Fieser & Jacobson J Am Chem Soc 59 2335 1937 Beilstein 1 8 III/IV 3142.]
CONVALLATOXIN Preparation Products And Raw materials
tracheloside Poricoic acid A(F) dipotassium dihydrogen 15alpha-hydroxy-2beta-[[2-O-isovaleryl-3,4-di-O-sulphonato-beta-D-glucopyranosyl]oxy]kaur-16-ene-18,19-dioate Isosorbide dinitrate Pachymic acid Madecassoside Carboxyatractyloside Madecassic acid roburic acid ALLEOSIDE A Terrestrosin D Quinine TERPIN MONOHYDRATE CONVALLATOXIN TRANS-TERPIN K-strophanthin-beta STROPHANTHIDIN periplogenin

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