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D5628

Sigma-Aldrich

Digitonin

~50% (TLC)

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

biological source

plant seeds (Digitalis purpurea)

description

non-ionic

assay

50% (TLC)

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.)

solubility

ethanol: 10 mg/mL, clear, colorless to faintly yellow

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
D141300410D1800000
vibrant-m

D5628

Digitonin

vibrant-m

D141

Digitonin

vibrant-m

300410

Digitonin, High Purity

vibrant-m

D1800000

Digitoxin

form

powder

form

powder

form

powder

form

-

assay

50% (TLC)

assay

-

assay

-

assay

-

mp

230-240 °C (dec.) (lit.)

mp

230-240 °C (dec.) (lit.)

mp

-

mp

240 °C (dec.) (lit.)

solubility

ethanol: 10 mg/mL, clear, colorless to faintly yellow

solubility

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

solubility

-

solubility

-

CMC

<0.5 mM (20-25°C)

CMC

<0.5 mM (20-25°C)

CMC

-

CMC

-

General description

Digitonin, a steroidal glycoside derived from the purple foxglove plant (Digitalis purpurea), stands as a versatile non-ionic detergent with diverse applications in cell biology and biochemical research. Its unique properties position it as a valuable tool for investigating cellular membranes, membrane proteins, and intracellular components. Digitonin demonstrates exceptional membrane solubilization capabilities, effectively extracting membrane-bound proteins while preserving their native conformation for studying interactions and activities. Additionally, it can also selectively permeabilize the cholesterol-rich plasma membrane, allowing for the isolation and purification of specific organelles, and facilitating the study of their functions.

The detergent′s cellular permeabilization property extends to various cell types, enabling the study of intracellular components and processes by introducing antibodies, enzymes, or other molecules into cells. In immunocytochemistry experiments, Digitonin plays a crucial role by permeabilizing cells, allowing for the labeling and detection of intracellular proteins and structures, offering insights into cellular organization and protein localization. Furthermore, Digitonin facilitates RNA extraction and purification by lysing cells, a critical step for molecular biology applications such as gene expression analysis and RNA sequencing. The detergent′s utility is also evident in immunoprecipitation experiments, where it solubilizes membrane proteins, enabling the isolation of specific protein-antibody complexes for the study of protein interactions and signaling pathways.

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

Other Notes

For additional information on our range of Biochemicals, please complete this form.

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Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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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)
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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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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
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Recruitment of circulating monocytes and neutrophils to infection sites is essential for host defense against infections. Here, we identified a previously unannotated gene that encodes an immunoglobulin-like receptor, designated CD300H, which is located in the CD300 gene cluster. CD300H has

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