Digitonin

• CAT Number: R019047
• CAS Number: 11024-24-1
• Molecular Formula: C56H92O29
• Molecular Weight: 1229.31
• Purity: ≥95%
• Synonyms: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-6-[(1R,2S,3S,4R,5’R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-3,15-dihydroxy-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2′-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: 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
• InChIKey: UVYVLBIGDKGWPX-KUAJCENISA-N
• SMILES: CC1CCC2(C(C3C(O2)C(C4C3(CCC5C4CCC6C5(CC(C(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)O)O)O)OC2C(C(C(C(O2)CO)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O)C)C)O)C)OC1

Digitonin (Cat No.: R019047) is a natural steroidal saponin extracted from the plant Digitalis purpurea. It consists of a steroid aglycone linked to a complex sugar chain and is known for its ability to solubilize membrane lipids, particularly cholesterol. In biochemistry, digitonin is widely used to selectively permeabilize cell membranes and isolate organelles like mitochondria. It forms water-soluble complexes with cholesterol, making it useful in membrane protein studies. Its nonionic nature and specificity make digitonin a valuable tool in cell biology and biochemical assays.

Reference

[1]. Lindnér PG, et al. Digitonin enhances the efficacy of carboplatin in liver tumour after intra-arterial administration. Cancer Chemother Pharmacol. 1997;40(5):444-8.
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[2]. Leendert van Dalsen, et al. In meso Crystallogenesis. Compatibility of the Lipid Cubic Phase With the Synthetic Digitonin Analogue, Glyco-Diosgenin. J Appl Crystallogr. 2020 Mar 25;53(Pt 2):530-535.
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