(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
(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
- 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 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
- pka
- 12.79±0.70(Predicted)
(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
Originator
Thevetin A,SigmaAldrich
Uses
Thevetin A is a cardiac glycoside that can lead to intoxication and poisoning.
Definition
ChEBI: Thevetin A is a trisaccharide derivative and a gentiobiosylthevetoside. It is functionally related to a cannogenin.
Manufacturing Process
A 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 Function
Cardiotonic
Purification Methods
Crystallise 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)-enolideSupplier
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