Digitonin

• CAS: 11024-24-1
• Catalog Number: ACM11024241
• Category: Main Products
• Molecular Weight: 1229.3
• Molecular Formula: C56H92O29
• Synonyms: Digitin; NSC 23471; NSC 237417
• 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
• 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
• 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: UVYVLBIGDKGWPX-KUAJCENISA-N
• Melting Point: 230-240 °C (dec.) (lit.)
• Density: 1.59 g/cm³
• Solubility: DMF: 30 mg/mL; DMSO: 30 mg/mL
• Appearance: A crystalline solid
• Complexity: 2230
• EC Number: 234-255-6
• Exact Mass: 1228.57242689
• Formal Charge: 0
• Hazard Statements: T
• Heavy Atom Count: 85
• Hydrogen Bond Acceptor Count: 29
• Hydrogen Bond Donor Count: 17
• 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
• Monoisotopic Mass: 1228.57242689
• Packing Group: II
• pKa: 12.68±0.70 (Predicted)
• Rotatable Bond Count: 14
• Safety Description: 22-28-36/37-45
• Shipping: Room temperature
• Stability: ≥2 years
• Storage Conditions: -20 °C
• Supplemental Hazard Statements: H301-H311-H330-H301+H311+H331
• Symbol: GHS06
• Topological Polar Surface Area: 455 Ų
• WGK Germany: 3
• XLogP3-AA: -3.9

Case Study

Study on the Disrupting Effect of Digitonin on Phospholipid Monolayers

M. Orczyk, et al. Langmuir, 2017, 33(15), 3871-3881.

The effects of digitonin were studied on a range of phospholipids, including zwitterionic (DPPC, DMPE, POPC, POPE, DSPC, DSPE, DPPE) and ionic (DPPS, DPPG).In this work, individual phospholipids were spread on water, exchanged with a solution of digitonin after solvent evaporation, and the change in surface pressure over time, Π(t), was recorded. Furthermore, the phase behavior of phospholipid monolayers exposed to the action of digitonin was observed by fluorescence microscopy, and structural information on digitonin-induced changes in the monolayer was collected using infrared reflection absorption spectroscopy (IRRAS).
· The surface pressure achieved during exposure of the monolayers to digitonin in each case was higher than that for its Gibbs layers on the bare water-air interface. This confirms that digitonin molecules penetrate the lipid layers.
· Digitonin displays selectivity towards phosphatidylethanolamine and phosphatidylserine phospholipids.
· The presence of digitonin, despite increasing surface pressure, induces disordering of the alkyl chains in DMPE, DPPE and DPPS monolayers. For DPPE and DPPS, which form highly ordered monolayers on pure water even at the lowest surface pressure, addition of digitonin can even lead to unprecedented LC-LE transition upon increasing surface pressure.

Preparation of Digitonin-Conjugated Gold Nanoparticles for Cholesterol Detection

Vidya Raj, et al. et al. Biosensors and Bioelectronics, 2011, 27(1), 197-200.

Gold nanoparticles were modified with digitonin, and the obtained digitonin conjugated gold nanoparticles (DGNP) have specific molecular recognition of cholesterol, thus showing the potential to be developed as an enzyme-free sensor for cholesterol. The strategy demonstrates a direct relationship between cholesterol levels and the corresponding plasma peak absorbance within the range of 160-600 ng/mL, with a detection limit of 100 ± 9 ng/mL.
Synthesis of digitonin-conjugated gold nanoparticles
· First, the surface of gold nanoparticles was modified with sulfhydryl groups in the presence of nonionic surfactants.
· Gold nanoparticles conjugated with 16-mercaptohexadecanoic acid (16-MHDA) were exposed to digitonin in the presence of H2SO4. The reaction mixture was agitated for 5 hours at room temperature to allow the carboxyl group (-COOH) to react with the hydroxyl group (-OH) of digitonin.
· Following this, the reaction mixture was purified by repeated centrifugation at 15,000 rpm for 20 minutes to yield digitonin-conjugated gold nanoparticles (DGNP).
· A cholesterol stock solution was made by dissolving 0.00387 g of cholesterol in a 100 mL mixture of acetone and water. Subsequently, 1 mL of DGNP was mixed with 10 µL of the cholesterol stock solution, with absorbance peaks being monitored as the cholesterol concentration varied.

Custom Reviews

August 20, 2023

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Work well in chemical detection
By precipitation method, digitonin can accurately detect cholesterol in plasma.

Custom Q&A

What is the melting point of digitonin ?

201°C - 300°C

What is the density of digitonin ?

1.1421

What is the specific optical rotation of digitonin ?

D20 -54° (0.45 g in 15.8 ml methanol)

What is the acidity factor of digitonin ?

12.68±0.70

What extinguishing agents are suitable for digitonin ?

Suitable extinguishing agents for digitonin are water, carbon dioxide, dry powder, sand and earth.

What are the relevant applications of digitonin ?

Digitonin can be used to determine cholesterol in plasma, bile and tissues using precipitation reactions. It is also used as a reagent for higher alcohols and phenols and thiophenols. It is also used in biochemical studies as a descaling agent and desolvent to treat isolated mitochondria and to dissolve the outer mitochondrial membrane.

What about the toxicity of digitonin ?

Digitonin is a highly toxic substance

How soluble is digitonin in water?

Digitonin has a maximum solubility of 10 mg/mL in water at 95°C. The resulting liquid is colorless and transparent.

What is the molecular mass of digitonin ?

1229.31

What is the bioacute toxic dose of digitonin ?

Oral-rat LD50 > 50 mg/kg; Oral-mouse LDL0: 90 mg/kg