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D141

Sigma-Aldrich

Digitonin

Used as non-ionic detergent

Synonym(s):
Digitin
Empirical Formula (Hill Notation):
C56H92O29
CAS Number:
Molecular Weight:
1229.31
Beilstein:
78654
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

form

powder

optical activity

[α]20/D −54°, c = 2.8 in methanol(lit.)

mol wt

micellar avg mol wt 70,000

aggregation number

60

CMC

<0.5 mM (20-25°C)

mp

230-240 °C (dec.) (lit.)

solubility

H2O: ~5 % (w/v) (solubilized by heating to 95 °C - 98 °C and then cooling to room temp.)

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

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

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This Item
D5628D5878PHL82516
Digitonin Used as non-ionic detergent

Sigma-Aldrich

D141

Digitonin

Digitonin ~50% (TLC)

Sigma-Aldrich

D5628

Digitonin

Digitoxin &#8805;92% (HPLC), powder

Sigma-Aldrich

D5878

Digitoxin

Digitoxin phyproof&#174; Reference Substance

PHL82516

Digitoxin

form

powder

form

powder

form

powder

form

-

mol wt

micellar avg mol wt 70,000

mol wt

micellar avg mol wt 70,000

mol wt

-

mol wt

-

aggregation number

60

aggregation number

60

aggregation number

-

aggregation number

-

CMC

<0.5 mM (20-25°C)

CMC

<0.5 mM (20-25°C)

CMC

-

CMC

-

mp

230-240 °C (dec.) (lit.)

mp

230-240 °C (dec.) (lit.)

mp

240 °C (dec.) (lit.)

mp

240 °C (dec.) (lit.)

solubility

H2O: ~5 % (w/v) (solubilized by heating to 95 °C - 98 °C and then cooling to room temp.)

solubility

-

solubility

chloroform: soluble

solubility

-

General description

Digitonin is a saponin obtained from foxglove. This non-ionic detergent has a head-tail structure. The bulky sugar headgroup of digitonin comprises two galactose, two glucose, and a xylose.

Application

Digitonin has been used along with permeabilization buffer for cyclic guanosine monophosphate-adenosine monophosphate (cyclic GMP-AMP) stimulation in cells.
Digitonin has been used in a study to assess a procedure for isolating mitochondria from ascites tumor cells. It has also been used in a study to investigate its effect on the cytotoxicity of plant secondary metabolites in cancer cells.

Biochem/physiol Actions

Digitonin plays a key role in permeabilizing cell membranes. It is capable of lysing eukaryotic cells but not bacterial membranes. It is also used to solubilize membrane components. It helps to create pores by interacting specifically with cholesterol in the membrane. It is preferred in biotechnology due to its mild detergency. This membrane-active compound act with doxorubicin against multi-drug resistant cancer cells.

Quality

Preparation is free of water-insoluble constituents.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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