CAS 11024-24-1

Digitonin

Description:

Digitonin is a glycoside derived from the plant Digitalis purpurea, commonly known as foxglove. It is primarily used in biochemistry and pharmacology for its ability to selectively solubilize membrane proteins, making it valuable in the study of cellular membranes and their components. Digitonin has a complex structure, featuring a steroid backbone linked to a sugar moiety, which contributes to its amphipathic nature. This property allows it to interact with lipid bilayers, facilitating the extraction of membrane proteins while maintaining their functional integrity. In addition to its biochemical applications, digitonin exhibits cytotoxic effects on certain cell types, which has implications for its use in research and potential therapeutic contexts. It is important to handle digitonin with care, as it can be toxic in higher concentrations. Overall, digitonin serves as a crucial tool in the study of membrane biology and the isolation of membrane-associated proteins.

Formula: C₅₆H₉₂O₂₉

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

InChI key: InChIKey=UVYVLBIGDKGWPX-KUAJCENISA-N

SMILES: C[C@@]12[C@@]3([C@]([C@@H](O)[C@]1([C@]4([C@](CC2)([C@]5(C)[C@@](CC4)(C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@H]7[C@H](O[C@H]8[C@H](O)[C@@H](O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)[C@@H](O)[C@@H](CO)O8)[C@@H](O[C@H]%10[C@H](O)[C@@H](O)[C@H](O)CO%10)[C@H](O)[C@@H](CO)O7)[C@H](O)[C@H]6O)[C@H](O)C5)[H])[H])[H])[H])(O[C@@]%11([C@H]3C)CC[C@@H](C)CO%11)[H])[H]

Synonyms:

• (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-(4xi)-beta-D-xylo-hexopyranosyl-(1->4)-beta-D-galactopyranoside
• (2alpha,3beta,5alpha,15beta,25R)-spirostan-2,3,15-triol
• (2α,3β,5α,15β,25R)-2,15-Dihydroxyspirostan-3-yl O-β-<span class="text-smallcaps">D</smallcap>-glucopyranosyl-(1→3)-O-β-<smallcap>D</smallcap>-galactopyranosyl-(1→2)-O-[β-<smallcap>D</smallcap>-xylopyranosyl-(1→3)]-O-β-<smallcap>D</smallcap>-glucopyranosyl-(1→4)-β-<smallcap>D</span>-galactopyranoside
• Ai3-44893
• Brn 0078654
• Digitin
• Digitogenin, 3-[O-β-<span class="text-smallcaps">D</smallcap>-glucopyranosyl-(1→3)-O-β-<smallcap>D</smallcap>-galactopyranosyl-(1→2)-O-[β-<smallcap>D</smallcap>-xylopyranosyl-(1→3)]-O-β-<smallcap>D</smallcap>-glucopyranosyl-(1→4)-β-<smallcap>D</span>-galactopyranoside]
• Digitogenin, 3-[O-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside]
• Digitogenin, glycoside
• Digitonina
• Digitonine
• Nsc 23471
• Nsc 237417
• Spiro[8H-naphth[2′,1′:4,5]indeno[2,1-b]furan-8,2′-[2H]pyran], β-<span class="text-smallcaps">D</span>-galactopyranoside deriv.
• Spirostan, β-<span class="text-smallcaps">D</span>-galactopyranoside deriv.
• beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1-3)-O-beta-D-galactopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-
• beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1.fwdarw.3)-O-beta-D-galactopyranosyl-(1.fwdarw.2)-O-(beta-D-xylopyranosyl-(1.fwdarw.3))-O-beta-D-glucopyranosyl-(1.fwdarw.4)-
• β-<span class="text-smallcaps">D</smallcap>-Galactopyranoside, (2α,3β,5α,15β,25R)-2,15-dihydroxyspirostan-3-yl O-β-<smallcap>D</smallcap>-glucopyranosyl-(1→3)-O-β-<smallcap>D</smallcap>-galactopyranosyl-(1→2)-O-[β-<smallcap>D</smallcap>-xylopyranosyl-(1→3)]-O-β-<smallcap>D</span>-glucopyranosyl-(1→4)-
• β-D-Galactopyranoside, (2α,3β,5α,15β,25R)-2,15-dihydroxyspirostan-3-yl O-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-
• Digitonin
• Spirostan, β-D-galactopyranoside deriv.

Digitonin

CAS: 11024-24-1

Formula: C₅₆H₉₂O₂₉

Color and Shape: White to Light yellow powder to crystaline

Molecular weight: 1,229.32

Ref: 3B-D0540

Digitonin

CAS: 11024-24-1

Digitonin

Formula: C₅₆H₉₂O₂₉

Color and Shape: white to yellowish powder

Molecular weight: 1,229.31g/mol

Ref: 54-BID3301

Digitonin

CAS: 11024-24-1

Formula: C₅₆H₉₂O₂₉

Color and Shape: White to pale yellow crystalline powder

Molecular weight: 1229.31

Ref: 7W-GC7189

Digitonin

CAS: 11024-24-1

Formula: C₅₆H₉₂O₂₉

Purity: 95%~99%

Molecular weight: 1229.32

Ref: BP-BP0488

Digitonin

CAS: 11024-24-1

Digitonin is a natural product of the glycoside family and is a detergent.

Formula: C₅₆H₉₂O₂₉

Color and Shape: Physical Description Crystals Or White Powder (Ntp 1992)

Molecular weight: 1229.31

Ref: TM-T2721

Digitonin Glycosides

Controlled Product

CAS: 11024-24-1

Formula: C₅₆H₉₂O₂₉

Color and Shape: White Solid

Molecular weight: 1229.31

Ref: TR-D446305

Digitonin - water-insoluble

CAS: 11024-24-1

Digitonin is produced from seeds of Digitalis pupurea and other Digitalis species. It is a steroid glycoside consisting of the aglycone digitogenin linked to five sugar residues. Reaction of naturally occurring steroids carrying a 3b-hydroxyl group with digitonin results in an insoluble precipitate. Digitonin has hemolytic activity and is toxic to humans. It permeabilizes plasma membranes of eukaryotic cells by complexing with membrane cholesterol and other unconjugated β-hydroxysterols. Digitonin is frequently used for solubilization of membrane proteins and permeabilization of cellular and nuclear membranes. Due to the complexing interactions it can be used for the determination of cholesterol and ergosterol This Digitonin product is insoluble in water.

Formula: C₅₆H₉₂O₂₉

Color and Shape: Powder

Molecular weight: 1,229.34 g/mol

Ref: 3D-OD09275

Digitonin, water-insoluble

CAS: 11024-24-1

Digitonin is produced from seeds of Digitalis pupurea and other Digitalis species. It is a steroid glycoside consisting of the aglycone digitogenin linked to five sugar residues. Reaction of naturally occurring steroids carrying a 3b-hydroxyl group with digitonin results in an insoluble precipitate. Digitonin has hemolytic activity and is toxic to humans. It permeabilizes plasma membranes of eukaryotic cells by complexing with membrane cholesterol and other unconjugated &beta;-hydroxysterols. Digitonin is frequently used for solubilization of membrane proteins and permeabilization of cellular and nuclear membranes. Due to the complexing interactions it can be used for the determination of cholesterol and ergosterol.

Formula: C₅₆H₉₂O₂₉

Molecular weight: 1,229.34 g/mol

Ref: 3D-D-3100

Digitonin, stable clear, water-soluble

CAS: 11024-24-1

This Digitonin product (stable clear, water soluble) is a superior water soluble Digitonin with improved stability for aqueous solutions. Digitonin is produced from seeds of Digitalis pupurea and other Digitalis species. It is a steroid glycoside consisting of the aglycone digitogenin linked to five sugar residues. Digitonin has hemolytic activity and is toxic to humans. Digitonin is frequently used for the solubilization of membrane proteins and for the permeabilization of cellular and nuclear membranes. It permeabilizes plasma membranes of eukaryotic cells by complexing with membrane cholesterol and other unconjugated β-hydroxysterols. This mechanism is used in procedures for the determination of cholesterol and ergosterol using Digitonin.
About this product: Aqueous solutions of conventional Digitonin will precipitate upon cooling to 4°C and will lose most of the biochemical function. Therefore, the precipitate is usually removed by filtration in many protocols. This filtration however decreases the concentration of Digitonin and alters the solubilizing power of the original product. In addition, precipitation and subsequent filtration result in an unknown Digitonin concentration in the final solutions and may negatively affect the reproducibility of any experiment with such solutions. In contrast to conventional Digitonin, our product Digitonin, stable clear, water soluble is a special grade that will not precipitate for at least one week.

Formula: C₅₆H₉₂O₂₉

Molecular weight: 1,229.34 g/mol

Ref: 3D-D-3203

Digitonin, water-soluble

CAS: 11024-24-1

Digitonin is produced from seeds of Digitalis pupurea and other Digitalis species. It is a steroid glycoside consisting of the aglycone digitogenin linked to five sugar residues. Reaction of naturally occurring steroids carrying a 3b-hydroxyl group with digitonin results in an insoluble precipitate. Digitonin has hemolytic activity and is toxic to humans. It permeabilizes plasma membranes of eukaryotic cells by complexing with membrane cholesterol and other unconjugated beta-hydroxysterols. Digitonin is frequently used for solubilization of membrane proteins and permeabilization of cellular and nuclear membranes. Due to the complexing interactions it can be used for the determination of cholesterol and ergosterol.

Formula: C₅₆H₉₂O₂₉

Molecular weight: 1,229.34 g/mol

Ref: 3D-D-3200

Digitonin (Digitin) extrapure, 50%

CAS: 11024-24-1

Formula: C₅₆H₉₂O₂₉

Color and Shape: White, Crystalline powder, Clear, Colourless

Molecular weight: 1229.30

Ref: SR-53755