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Merck
CN

D9404

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
UNSPSC Code:
12161900
NACRES:
NA.25
PubChem Substance ID:
24894291
EC Number:
205-603-4
Beilstein/REAXYS Number:
95448
MDL number:
MFCD00003687

Key Documents

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InChI key

XZTUSOXSLKTKJQ-CESUGQOBSA-N

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

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

description

non-ionic

assay

≥97.0% (TLC)

form

powder

mol wt

374.51 g/mol

mp

253 °C (lit.)

Gene Information

rat ... Atp1a1(24211)

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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.

General description

Digitoxigenin is the aglycone of digitoxin.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000166569
0000166569
0000136893
0000131498
0000131499

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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)
T Warashina et al.
Chemical & pharmaceutical bulletin, 48(4), 516-524 (2000-04-27)
Twenty-nine new oxypregnane glycosides were obtained along with two known cardenolides, frugoside and gofruside, and three known 12-O-acylated pregnane glycosides from the roots of Asclepias incarnata L. (Asclepiadaceae). By detailed studies of the 1H- and 13C-NMR spectra, the structures were
P De Weer et al.
The Journal of general physiology, 117(4), 315-328 (2001-03-30)
The steady-state voltage and [Na(+)](o) dependence of the electrogenic sodium pump was investigated in voltage-clamped internally dialyzed giant axons of the squid, Loligo pealei, under conditions that promote the backward-running mode (K(+)-free seawater; ATP- and Na(+)-free internal solution containing ADP
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
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
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