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D5628

Sigma-Aldrich

Digitonin

~50% (TLC)

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Synonym(s):
Digitin
Empirical Formula (Hill Notation):
C56H92O29
CAS Number:
11024-24-1
Molecular Weight:
1229.31
Beilstein:
78654
EC Number:
234-255-6
MDL number:
MFCD00077729
PubChem Substance ID:
24893949
NACRES:
NA.25

description

non-ionic

form

powder

mol wt

micellar avg mol wt 70,000

concentration

~50% (TLC)

aggregation number

60

CMC

<0.5 mM (20-25°C)

mp

230-240 °C (dec.) (lit.)

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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1 of 4

This Item
D141D5878BP855
Digitonin ~50% (TLC)

Sigma-Aldrich

D5628

Digitonin

Digitonin Used as non-ionic detergent

Sigma-Aldrich

D141

Digitonin

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

Sigma-Aldrich

D5878

Digitoxin

Digitoxin British Pharmacopoeia (BP) Reference Standard

BP855

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.)

General description

Digitonin is a biodetergent and saponin that synergistically enhances the cytotoxicity of plant secondary metabolites in cancer cells.
Digitonin, a non-ionic detergent, is obtained from foxglove. This saponin has a head-tail structure. Two galactose, two glucose, and a xylose are present on its bulky sugar headgroup.

Application

Digitonin has been used in a study to investigate how lipopeptide toxins target biological membranes.
Digitonin has been used:
  • to incubate isolated mitochondria for removing the mitochondrial outer membrane for mitoplasts preparation
  • in the permeabilization of HeLa cells for in vitro import assay
  • as a component in HEPES-buffered saline (HBS) to permeate the cells and release the aequorins for fluorescence and bioluminescence imaging

Biochem/physiol Actions

Digitonin plays a key role in permeabilizing cell membranes. It also helps to solubilize membrane components. Digitonin specifically interacts with cholesterol in the membrane, resulting in pore formation. It helps to lyse eukaryotic cells but not bacterial membranes.

Features and Benefits

  • Can extract membrane proteins like supercomplexes from the mitochondrial inner membrane
  • Solubilizes 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) large unilamellar vesicles (LUVs) gradually at high temperature
  • Canorm micelles at a wide range of concentrations

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301 - H373

Precautionary Statements

P301 + P310 + P330 - P314

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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Saponin A glycoside used to permeabilize cellular membranes. Exhibits hemolytic activity.

Millipore

558255

Saponin

The dopamine D1 receptor: partial purification of a digitonin-solubilized receptor-guanine nucleotide binding complex.
H B Niznik et al.
Biochemical pharmacology, 35(17), 2974-2977 (1986-09-01)
Dominic S Alonzi et al.
Cellular and molecular life sciences : CMLS, 70(15), 2799-2814 (2013-03-19)
Endoplasmic reticulum-associated degradation (ERAD) is a key cellular process whereby misfolded proteins are removed from the endoplasmic reticulum (ER) for subsequent degradation by the ubiquitin/proteasome system. In the present work, analysis of the released, free oligosaccharides (FOS) derived from all
Xianying A Cui et al.
PLoS biology, 10(5), e1001336-e1001336 (2012-06-09)
In metazoans, the majority of mRNAs coding for secreted and membrane-bound proteins are translated on the surface of the endoplasmic reticulum (ER). Although the targeting of these transcripts to the surface of the ER can be mediated by the translation
Didier Blanot et al.
Chemical biology & drug design, 79(1), 2-8 (2011-08-06)
Muramyl peptides derived from bacterial peptidoglycan have long been known for their ability to trigger host innate immune responses, including inflammation and antimicrobial defense. Muramyl peptides have also been widely studied for their role as immune adjuvants. In mammals, the
Safaa Yehia Eid et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(14), 1307-1314 (2012-10-16)
In phytotherapy, extracts from medicinal plants are employed which contain mixtures of secondary metabolites. Their modes of action are complex because the secondary metabolites can react with single or multiple targets. The components in a mixture can exert additive or
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