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DIGITOXIGENIN

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DIGITOXIGENIN Basic information

Product Name:
DIGITOXIGENIN
Synonyms:
  • 5BETA,20[22]-CARDENOLIDE-3BETA,14-DIOL
  • 3BETA,14-DIHYDROXY-5BETA,20[22]-CARDENOLIDE
  • 20(22),5BETA-CARDENOLID-3BETA,14BETA-DIOL
  • 3,14,21-TRIHYDROXY-20(22)-NORCHOLENIC ACID LACTONE
  • cerberigenin
  • delta-sup(20:22)-3,14,21-trihydroxynorcholenicacidlactone
  • digitoxigenine
  • echujetin
CAS:
143-62-4
MF:
C23H34O4
MW:
374.51
EINECS:
205-603-4
Product Categories:
  • Biochemistry
  • Steroids
  • Steroids (Others)
  • ATPase
Mol File:
143-62-4.mol
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DIGITOXIGENIN Chemical Properties

Melting point:
253-255 °C (dec.)(lit.)
alpha 
D17 +19.1° (c = 1.36 in methanol)
Boiling point:
423.5°C (rough estimate)
Density 
1.0284 (rough estimate)
refractive index 
1.4433 (estimate)
storage temp. 
Store at -20°C
solubility 
DMF: 25 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 20 mg/ml; Ethanol: 5 mg/ml
pka
14.93±0.70(Predicted)
form 
powder to crystal
color 
White to Almost white
Water Solubility 
11.24mg/L(30 ºC)
Merck 
14,3162
BRN 
95448
Stability:
Hygroscopic
LogP
2.640
CAS DataBase Reference
143-62-4(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 3462 6.1/PG 2
WGK Germany 
3
RTECS 
FH4975000
HS Code 
2938.90.0000
HazardClass 
6.1(a)
PackingGroup 
II
Toxicity
cat,LDLo,intravenous,254ug/kg (0.254mg/kg),GASTROINTESTINAL: NAUSEA OR VOMITING,Journal of the American Pharmaceutical Association. Vol. 27, Pg. 189, 1938.

MSDS

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DIGITOXIGENIN Usage And Synthesis

Uses

Cardiotonic;Na+ K+ ATPase inhibitor

Definition

ChEBI: Digitoxigenin is a 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22). It is a 3beta-hydroxy steroid and a 14beta-hydroxy steroid. It derives from a hydride of a 5beta-cardanolide.

Purification Methods

Dissolve digitoxigenin in EtOAc, wash it with H2O, dry it (Na2SO4), evaporate and recrystallise it from 40% aqueous EtOH or aqueous MeOH then EtOAc/Et2O. The UV has max at 218nm ( 14,500 M-1cm-1). The 3-acetate crystallises from Me2CO/Et2O with m 222-227o, [] D 20 +21o (c 1, CHCl3). [Wyss et al. Helv Chim Acta 43 644 1960, Cruz et al. J Org Chem 4 2 3580 1977, Beilstein 18 IV 1468.]

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