Digitonin

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Structure of Digitonin
Structure of Digitonin

Digitonin is a glycoside obtained from Digitalis purpurea; the aglycone is digitogenin. Used as a detergent, it effectively water-solubilizes lipids. As such, it has several membrane-related applications in biochemistry, including solubilizing membrane proteins, precipitating cholesterol, and permeabilizing cell membranes.

Digitonin is sometimes confused with the cardiac drug digoxin (sometimes also called digitalis or digitoxin), but has no heart-related effects.

Physical & Chemical Properties

Chemical Formula= C56H92O29
Molecular Weight= 1229.3
Critical micelle concentration= < 0.5 mM
Average micellar weight= 70000
Solubility= 5 % (w/v)
Appearance = White to off-white powder
Boiling Point/Melting Point= 230 °C to 240 °C
Specific Rotation= -47 TO -49º (10 g/100 ml 75% Acetic Acid at 25 °C)1
Aggregation number = 60.

Biological Properties

Rat-LD50 : 4 mg/kg body weight (IVN), 51 mg/kg body weight (ORAL)

External links

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Glycosides
Bond:
Geometry:
Glycone:
Aglycone:
Major families of biochemicals
Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids
Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles

Wikipedia content modification information:

  • This page was last modified on 16 September 2008, at 23:59.

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