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D9404

Sigma-Aldrich

Digitoxigenin

Synonym(s):

3β,14-Dihydroxy-5β,20(22)-cardenolide, 3,14,21-Trihydroxy-20(22)-norcholenic acid lactone, 5β,20(22)-Cardenolide-3β,14-diol

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About This Item

Empirical Formula (Hill Notation):
C23H34O4
CAS Number:
143-62-4
Molecular Weight:
374.51
Beilstein:
95448
EC Number:
205-603-4
MDL number:
MFCD00003687
UNSPSC Code:
12161900
PubChem Substance ID:
24894291
NACRES:
NA.25

description

non-ionic

Quality Level

200

Assay

≥97.0% (TLC)

form

powder

mol wt

374.51 g/mol

mp

253 °C (lit.)

SMILES string

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@]([H])(CC[C@]34O)C5=CC(=O)OC5)[C@@]1(C)CC[C@H](O)C2

InChI

1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1

InChI key

XZTUSOXSLKTKJQ-CESUGQOBSA-N

Gene Information

rat ... Atp1a1(24211)

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General description

Digitoxigenin is the aglycone of digitoxin.

Application

Digitoxigenin has been used in a study to assess its stereochemical effects in cancer cytotoxicity. It has also been used in a study to investigate the advantage of gold(I)-catalyzed glycosidation of glycosyl o-alkyl benzoates to assemble digitoxin.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The crystal structure of digitoxigenin, C23H34O4
Isabella Karle and J. Karle
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, B25, 434-434 (1969)
Maoquan Zhou et al.
Organic letters, 8(19), 4339-4342 (2006-09-08)
A convergent and stereocontrolled route to trisaccharide natural product digitoxin has been developed. The route is amenable to the preparation of both the digitoxigen mono- and bisdigitoxoside. This route featured the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1,3-transposition
A Babes et al.
Biophysical journal, 79(5), 2557-2571 (2000-10-29)
We have used admittance analysis together with the black lipid membrane technique to analyze electrogenic reactions within the Na(+) branch of the reaction cycle of the Na(+)/K(+)-ATPase. ATP release by flash photolysis of caged ATP induced changes in the admittance
Michael C Roy et al.
Journal of natural products, 68(10), 1494-1499 (2005-10-29)
A series of cardenolides and related compounds have been isolated from the aerial parts and roots of the ornamental milkweed, Asclepias curassavica. Their structures were determined by spectroscopic and chemical methods. Among them, three derivatives of calactinic acid methyl ester
M Gobbini et al.
Journal of medicinal chemistry, 44(23), 3821-3830 (2001-11-02)
The synthesis and binding affinities to the digitalis Na(+),K(+)-ATPase receptor of a series of 3 beta,14 beta-dihydroxy-5 beta-androstane and 3 beta-hydroxy-14-oxoseco-D-5 beta-androstane derivatives bearing a 17 alpha-(aminoalkoxy)imino chain are reported; some derivatives were also studied for their inotropic activity. Our
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