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Digitonin, MP Biomedicals™

Permeabilizes plasma membranes of eukaryotic cells. Digitonin, MP Biomedicals is a mild nonionic detergent that complexes with membrane cholesterol and other unconjugated β-hydroxysterols. It is used to solubilize receptors and permeabilize cellular

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Chemical Identifiers

CAS 11024-24-1
Molecular Formula C56H92O29
Molecular Weight (g/mol) 1229.32
MDL Number MFCD00077729
InChI Key UVYVLBIGDKGWPX-QYLWGQLPSA-N
Synonym digitonin
PubChem CID 102004607
IUPAC Name (2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1'R,2R,2'S,3'S,4'R,7'S,8'R,9'S,12'S,13'S,15'R,16'R,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES C[C@H]1[C@H]2[C@@H](O[C@]11CCC(C)CO1)[C@@H](O)[C@H]1[C@@H]3CC[C@H]4C[C@@H](O[C@@H]5O[C@H](CO)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]21C
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Description

Description

Digitonin has following uses:

  • Cholesterol determination
  • Use of digitonin-permeabilized adipocytes for cAMP studies
  • Solubilization of membrane proteins
  • The water soluble form can be used for the isolation of mitotic chromosomes
Specifications

Chemical Identifiers

11024-24-1
1229.32
UVYVLBIGDKGWPX-QYLWGQLPSA-N
102004607
C[C@H]1[C@H]2[C@@H](O[C@]11CCC(C)CO1)[C@@H](O)[C@H]1[C@@H]3CC[C@H]4C[C@@H](O[C@@H]5O[C@H](CO)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]21C
C56H92O29
MFCD00077729
digitonin
(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1'R,2R,2'S,3'S,4'R,7'S,8'R,9'S,12'S,13'S,15'R,16'R,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Specifications

11024-24-1
230°C to 240°C (decomposition)(literature)
MFCD00077729
Soluble in boiling water (1g/10mL). Heat for 15 minutes at 98°C. Cool and place at 4°C for 3 hrs and filter off any precipitate. Soluble in absolute alcohol (1g/57mL) and 95% alcohol (1g).
C[C@H]1[C@H]2[C@@H](O[C@]11CCC(C)CO1)[C@@H](O)[C@H]1[C@@H]3CC[C@H]4C[C@@H](O[C@@H]5O[C@H](CO)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]21C
1229.32
1229.3
[α]20/D −54° (c=2.8, methanol) (Lit.)
White Powder
C56H92O29
digitonin
UVYVLBIGDKGWPX-QYLWGQLPSA-N
(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1'R,2R,2'S,3'S,4'R,7'S,8'R,9'S,12'S,13'S,15'R,16'R,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
102004607
CriticalMicelle Concentration (CMC) <0.5mM (20–25°C) (Lit.)
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Safety and Handling

Recommended Storage : Store at Room Temperature (15°C to 30°C), dessicate.

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