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64107

Sigma-Aldrich

Gitoxin

≥99% (HPLC)

Synonym(s):

Anhydrogitalin, Bigitalin, Pseudodigitoxin

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About This Item

Empirical Formula (Hill Notation):
C41H64O14
CAS Number:
4562-36-1
Molecular Weight:
780.94
EC Number:
224-934-5
MDL number:
MFCD00021173
UNSPSC Code:
12352200
PubChem Substance ID:
329759926
NACRES:
NA.25

Assay

≥99% (HPLC)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

C[C@H]1O[C@H](C[C@H](O)[C@@H]1O)O[C@H]2[C@@H](O)C[C@@H](O[C@@H]2C)O[C@H]3[C@@H](O)C[C@@H](O[C@@H]3C)O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@]7(C)[C@H]([C@@H](O)C[C@]67O)C8=CC(=O)OC8)C4

InChI

1S/C41H64O14/c1-19-36(47)27(42)14-33(50-19)54-38-21(3)52-34(16-29(38)44)55-37-20(2)51-32(15-28(37)43)53-24-8-10-39(4)23(13-24)6-7-26-25(39)9-11-40(5)35(22-12-31(46)49-18-22)30(45)17-41(26,40)48/h12,19-21,23-30,32-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25+,26-,27+,28+,29+,30+,32+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1

InChI key

LKRDZKPBAOKJBT-CNPIRKNPSA-N

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Application

Gitoxin, a cardiac glycoside from the Woolly Foxglove (Digitalis lanata), may be studied for its potential cardiac applications similar to those of digoxin. Gitoxin is a starting material for the synthesis of gitoxin derivatives with activity as cardiac glycosides.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Certificates of Analysis (COA)

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P Pellegrin et al.
European journal of drug metabolism and pharmacokinetics, 8(1), 1-8 (1983-01-01)
Hepatic clearance of gitoxin has been studied in the rabbit and compared with that of digoxin using an isolated perfused liver technique. During 1.5 hour perfusions with a modified Krebs-Henseleit solution, gitoxin perfusate levels decreased biexponentially; the distribution and elimination
Danijela Krstić et al.
Journal of enzyme inhibition and medicinal chemistry, 19(5), 409-415 (2005-01-15)
Inhibition of Na+/K+-ATPase activity from human erythrocyte membranes and commercial porcine cerebral cortex by in vitro single and simultaneous exposure to digoxin and gitoxin was investigated to elucidate the difference in the mechanism of the enzyme inhibition by structurally different
M L Coates et al.
Biomedical & environmental mass spectrometry, 13(4), 199-204 (1986-04-01)
Positive- and negative-ion mass spectra of five glycoconjugates were obtained using laser desorption/Fourier transform mass spectrometry. These were the glycoalkaloids alpha-solanine and alpha-tomatine and the steroid glycosides gitoxin, lanatoside A and digitonin. Doping with KCl yielded both potassium- and chloride-attachment
P L Pellegrin et al.
Drug metabolism and disposition: the biological fate of chemicals, 12(2), 235-241 (1984-03-01)
After in vitro perfusion of rabbit isolated liver with an emulsion of perfluorocarbon containing [3H]gitoxin, the radioactivity in the liver and in the bile was the sum of that contained in a volatile fraction (tritiated water due to metabolism of
L Muthuselvi et al.
Colloids and surfaces. B, Biointerfaces, 51(1), 39-43 (2006-07-04)
This work reports the use of simple coacervates of the hydrophobic protein zein to encapsulate Gitoxin, a cardiotonic glycoside. The microspheres obtained using ethanol, methanol, iso-propyl alcohol were characterized using viscosity index, scanning electron microscopy (SEM) and laser light scattering
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