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: 78654
• EC Number: 234-255-6
• MDL number: MFCD00077729
• PubChem Substance ID: 24893429
• NACRES: NA.25

Properties

• 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

Description

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.

Safety Information

• Pictograms: 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