(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide

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CAS:37933-66-7
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(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide manufacturers

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(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Basic information
Product Name:(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide
Synonyms:(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide;3β-[[4-O-[6-O-(β-D-Glucopyranosyl)-D-glucopyranosyl]-6-deoxy-3-O-methyl-α-L-glucopyranosyl]oxy]-14-hydroxy-19-oxo-5β-card-20(22)-enolide;Thevetin A >=95% (LC/MS-ELSD);Thevetin A DISCONTINUED;Card-20(22)-enolide, 3-[(O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxy-19-oxo-, (3β,5β)-
CAS:37933-66-7
MF:C42H64O19
MW:872.94616
EINECS:253-722-5
Product Categories:
Mol File:37933-66-7.mol
(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Structure
(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Chemical Properties
Melting point 208-210°
alpha D24 -72.0 ±1.5° (c = 1.48 in methanol)
Boiling point 1035.6±65.0 °C(Predicted)
density 1.49±0.1 g/cm3(Predicted)
storage temp. -20°C
pka12.79±0.70(Predicted)
form solid
color White to off-white
Major Applicationmetabolomics
vitamins, nutraceuticals, and natural products
InChIKeyWPNLWBRKPZXVGD-XQNLSVLQSA-N
Safety Information
WGK Germany 3
Storage Class11 - Combustible Solids
MSDS Information
(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Usage And Synthesis
OriginatorThevetin A,SigmaAldrich
UsesThevetin A is a cardiac glycoside that can lead to intoxication and poisoning.
DefinitionChEBI: Thevetin A is a trisaccharide derivative and a gentiobiosylthevetoside. It is functionally related to a cannogenin.
Manufacturing ProcessA mixture of Thevetins A and B was prepared by extraction from seeds of Thevetia neriifolia.
100 g of this mixture are dissolved in 1500 ml of aqueous ethanol at 96°C. Then 50 ml of a 30% solution of sodium bisulfite is added. The solution is left for about 1 hour and is then diluted with 3 L of water. The resulting solution is extracted 3 times in reflux extraction apparatus with 4 L of n-butanol as the extraction solvent. Thevetin A passes into said n-butanol which is then washed with distilled water and evaporated to dryness. The crude thevetin A is recrystallized in absolute ethanol (100 ml) and precipitating with 10 volumes of isopropyl oxide. The residual thevetin B of the bisulfite solution also may be prepared.
Therapeutic FunctionCardiotonic
Biological ActivityCardiac glycosides found in yellow oleander including thevetin A, have potential to tre at patients with heart failure and atrial fibrillation.
Purification MethodsCrystallise thevetin A from H2O. The acetyl derivative crystallises from MeOH/Et2O at -15o with m 145-149o, and [] D -54.2o (c 1.86, CHCl3). [Block et al. Helv Chim Acta 43 652 1960, 13C NMR: Tori et al. Tetrahedron Lett 717 1977, Beilstein 18 III/IV 2552, 18/4 V 439.]
(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide Preparation Products And Raw materials
Raw materials1-Butanol-->Sodium bisulfite-->Ethanol
Tag:(3beta,5beta)-3-[(O-beta-D\-glucopyranosyl-(1->6)-O-D\-glucopyranosyl-(1->4)-6-deoxy-3-O-methyl-alpha-L\-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide(37933-66-7) Related Product Information

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