Digitonin - 50% , CAS No.11024-24-1

CAS: 11024-24-1 Cat. No.: D104508 Molecular Weight: 1229.31 Beilstein Registry Number: 78654 EC Number: 234-255-6 PubChem CID: 6474107

GRADE & PURITY 50%

Synonyms

AI3-44893 | (25R)-2beta,15alpha-dihydroxy-5beta,8alpha,10alpha,14beta,17beta-spirostan-3alpha-yl beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside | Digitonin |

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

It is a biodetergent and saponin that synergistically enhances the cytotoxicity of plant secondary metabolites in cancer cells.
It has been used in a study to investigate how lipopeptide toxins target biological membranes.A non-ionic biodetergent used to solubilize membrane-bound proteins

Specifications

Synonyms

AI3-44893 | (25R)-2beta, 15alpha-dihydroxy-5beta, 8alpha, 10alpha, 14beta, 17beta-spirostan-3alpha-yl beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside | Digitonin |

Specifications & Purity

50%

Biochemical and Physiological Mechanisms

Digitalis saponins play a crucial role in infiltrating cell membranes. It can also be used to dissolve cell membrane components. Digitalis saponins can interact with cholesterol in the cell membrane to form pores. It can lyse eukaryotic cells, but cannot

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, \xa0refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

• Pubchem Sid: 504764245
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764245
• Canonical 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
• 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)-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
• InChIKey: UVYVLBIGDKGWPX-KUAJCENISA-N
• 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
• Isomeric SMILES: C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)[C@H]([C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(C[C@H]([C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)O)C)C)O)C)OC1
• WGK Germany: 3
• RTECS: IH2050050
• PubChem CID: 6474107
• Molecular Weight: 1229.31
• Beilstein: 78654
• Reaxy-Rn: 78654

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroidal glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroidal glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Steroidal saponins
• Alternative Parents: Triterpenoids Spirostanes and derivatives Oligosaccharides Hydroxysteroids O-glycosyl compounds Ketals Oxanes Tetrahydrofurans Secondary alcohols Cyclic alcohols and derivatives Polyols Oxacyclic compounds Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Steroidal saponin - Triterpenoid - Spirostane skeleton - Oligosaccharide - 2-hydroxysteroid - 15-hydroxysteroid - Hydroxysteroid - Glycosyl compound - O-glycosyl compound - Ketal - Oxane - Cyclic alcohol - Tetrahydrofuran - Secondary alcohol - Polyol - Oxacycle - Acetal - Organoheterocyclic compound - Primary alcohol - Organooxygen compound - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in ethanol. Insoluble in water, chloroform, and ether.
• Specific Rotation[α]: -52° (C=1,EtOH)
• Melt Point(°C): 230-240°C
• Molecular Weight: 1229.300 g/mol
• XLogP3: -3.900
• Hydrogen Bond Donor Count: 17
• Hydrogen Bond Acceptor Count: 29
• Rotatable Bond Count: 14
• Exact Mass: 1228.57 Da
• Monoisotopic Mass: 1228.57 Da
• Topological Polar Surface Area: 455.000 Ų
• Heavy Atom Count: 85
• Formal Charge: 0
• Complexity: 2230.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 38
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Suli Chong, Yang Liu, Ziming Bian, Dongxue Hu, Shiqun Guo, Chenfei Dong, Jiayue Zeng, Sairong Fan, Xiaoming Chen.  (2025)  GALNT6 dual regulates innate immunity STING signaling and PD-L1 expression to promote immune evasion in pancreatic ductal adenocarcinoma.  CELLULAR SIGNALLING,      [PMID:40541816] [10.1016/j.cellsig.2025.111942]