(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
- 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
- CAS No.
- 37933-66-7
- Chemical 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
- Thevetin A DISCONTINUED;Thevetin A >=95% (LC/MS-ELSD);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;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)-;(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
- CBNumber
- CB7916722
- Molecular Formula
- C42H64O19
- Formula Weight
- 872.94616
- 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 Property
- 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)
- form
- solid
Safety
- WGK Germany
- 3
N-Bromosuccinimide Price
- Product number
- SMB00166
- Product name
- Thevetin A
- Purity
- ≥95% (LC/MS-ELSD)
- Packaging
- 1mg
- Price
- $327
- Updated
- 2024/03/01
- Product number
- API0016381
- Product name
- THEVETIN A
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $498.05
- Updated
- 2021/12/16
(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,Usage,Production
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
Biological Activity
Cardiac glycosides found in yellow oleander including thevetin A, have potential to tre at patients with heart failure and atrial fibrillation.
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)-enolide Preparation Products And Raw materials
Raw materials
Preparation Products
(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 Suppliers
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