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Merck

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)

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

D9404-VAR: + D9404-10MG: + D9404-25MG: + D9404-100MG: + D9404-BULK:

jan

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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)
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
Ming Zhao et al.
Journal of natural products, 70(7), 1098-1103 (2007-06-28)
Four new cardenolide monoglycosides, cardenolides N-1 (1), N-2 (2), N-3 (3), and N-4 (4), were isolated from Nerium oleander, together with two known cardenolides, 5 and 12, and seven cardenolide monoglycosides, 6-11 and 13. The structures of compounds 1-4 were
Ingo P Korndörfer et al.
Journal of molecular biology, 330(2), 385-396 (2003-06-26)
DigA16 is an artificial digoxigenin-binding protein, which was derived from the bilin-binding protein, a lipocalin of Pieris brassicae, via reshaping of its natural ligand pocket. Here we report the crystal structures of DigA16 in the presence of either digoxigenin or
Baradwaj Gopal Ravi et al.
Journal of chromatography. A, 1618, 460903-460903 (2020-02-10)
Plants of the Digitalis genus contain a cocktail of cardenolides commonly prescribed to treat heart failure. Cardenolides in Digitalis extracts have been conventionally quantified by high-performance liquid chromatography yet the lack of structural information compounded with possible co-eluents renders this
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