(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

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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 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)

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SMB00166
Product name: Thevetin A
Purity: ≥95% (LC/MS-ELSD)
Packaging: 1mg
Price: $327
Updated: 2024/03/01

American Custom Chemicals Corporation

Product number: API0016381
Product name: THEVETIN A
Purity: 95.00%
Packaging: 5MG
Price: $498.05
Updated: 2021/12/16

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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 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

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

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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 Suppliers

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37933-66-7, (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)-enolideRelated Search:

(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)-

37933-66-7