D141

Digitonin

Used as non-ionic detergent

• Synonym(s): Digitin
• Empirical Formula (Hill Notation): C₅₆H₉₂O₂₉
• CAS Number: 11024-24-1
• Molecular Weight: 1229.31
• Beilstein/REAXYS Number: 78654
• EC Number: 234-255-6
• MDL number: MFCD00077729
• UNSPSC Code: 12161900
• PubChem Substance ID: 24893429
• NACRES: NA.25

Properties

• biological source: plant seeds (Digitalis purpurea)
• 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
• impurities: <6.0% water
• CMC: <0.5 mM (20-25°C); <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

Description

General description

Digitonin, a steroidal saponin extracted from the purple foxglove plant (Digitalis purpurea), stands as a versatile non-ionic detergent crucial for cell biology and biochemical research. Its unique attributes position it as a valuable asset in the exploration of cellular membranes, membrane proteins, and intracellular components. Digitonin′s key properties and applications include its ability to solubilize membrane-bound proteins effectively while preserving their native conformation, making it an ideal tool for studying membrane protein interactions and activities.

Moreover, Digitonin selectively permeabilizes the cholesterol-rich plasma membrane, leaving organelle membranes intact. This feature facilitates the extraction and purification of specific organelles, contributing to the study of their functions and roles in cellular processes. The detergent′s capability to permeabilize diverse cell types allows the study of intracellular components and processes by introducing molecules, antibodies, or enzymes into cells. Additionally, Digitonin finds application in immunocytochemistry experiments, enabling the labeling and detection of intracellular proteins and structures.

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.

Features and Benefits

Highly versatile compound for your cell biology and biochemical research

Quality

Preparation is free of water-insoluble constituents.

Other Notes

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

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H373
• pcodes: P301 + P310 + P330 - P314
• 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