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Merck
CN

37008

Digitonin

~50% (TLC)

Synonym(s):

Digitin

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About This Item

Empirical Formula (Hill Notation):
C56H92O29
CAS Number:
11024-24-1
Molecular Weight:
1229.31
EC Number:
234-255-6
UNSPSC Code:
12352200
MDL number:
MFCD00077729
Beilstein/REAXYS Number:
78654

Key Documents

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InChI

1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36-,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1

InChI key

UVYVLBIGDKGWPX-KUAJCENISA-N

SMILES string

C[C@@]12[C@]([C@@H]3C)([H])[C@](O[C@]34CC[C@@H](C)CO4)([H])[C@@H](O)[C@@]1([H])[C@@](CC[C@]5([H])[C@@]6(C[C@@H](O)[C@H](O[C@]([C@@H]([C@@H](O)[C@H]7O[C@@](O[C@H](CO)[C@@H](O)[C@@H]8O[C@@](OC[C@@H](O)[C@@H]9O)([H])[C@@H]9O)([H])[C@@H]8O[C@@](O[C@H](CO)[C@H

description

non-ionic

optical activity

[α]20/D −54.5±3°, c = 1% in methanol (dry matter)

mol wt

micellar avg mol wt 70,000

concentration

~50% (TLC)

aggregation number

60

mp

230-240 °C (dec.) (lit.)

solubility

ethanol: 10 mg/mL, clear, almost colorless (hot)

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Application

suitable for determination of cholesterol

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Permeabilizes plasma membranes of eukaryotic cells by complexing with membrane cholesterol and other unconjugated β-hydroxysterols. Use of digitonin-permeabilized adipocytes for cAMP studies; Selective precipitation of cholesterol; Solubilization of membrane proteins; Opioid receptor proteins.

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T J Scallen et al.
The Journal of cell biology, 40(3), 802-813 (1969-03-01)
A major methodological problem in the intracellular localization of cholesterol is the nearly complete extraction of sterols during routine dehydration and embedding procedures for electron microscopy. Cholesterol digitonide (a sterol complex with digitonin), however, is qualitatively insoluble in these solvents.
C D Demoliou-Mason et al.
FEBS letters, 170(2), 378-382 (1984-05-21)
The binding sites for opiates (agonist and antagonist) and opioid peptides can be solubilized from rat brain membranes with digitonin in the presence of Mg2+ (10 mM). High affinity and high capacity binding to the soluble delta, mu, and kappa
Solubilization of functional membrane proteins.
L M Hjelmeland et al.
Methods in enzymology, 104, 305-318 (1984-01-01)
Use of digitonin-permeabilized adipocytes for cAMP studies.
R A Mooney
Methods in enzymology, 159, 193-202 (1988-01-01)

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