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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,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-tetramethyl-spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-tetrahydropyran]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
State
State

At room temperature, digoxin is in a solid state, typically found as a crystalline powder.

Melting point (Celsius)
230.00
Melting point (Kelvin)
503.00
Boiling point (Celsius)
266.00
Boiling point (Kelvin)
539.00
General information
Molecular weight
780.94g/mol
Molar mass
780.9380g/mol
Density
1.1000g/cm3
Appearence

Digoxin is a white or almost white, crystalline powder. It is practically insoluble in water, but freely soluble in diluted ethanol.

Comment on solubility

Solubility of the Compound

The solubility of the compound (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,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-tetramethyl-spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-tetrahydropyran]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-4-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (C41H64O14) can be characterized by several notable points:

  • Polarity: The presence of multiple hydroxyl groups (–OH) in its structure suggests that the compound is likely polar, which often enhances solubility in polar solvents such as water.
  • Hydrogen Bonding: The hydroxyl groups can engage in hydrogen bonding with solvent molecules, further increasing solubility. This behavior is often pivotal for compounds with several hydroxyl groups.
  • Hydrophobic Characteristics: Despite its polar parts, the compound may also contain regions that are hydrophobic due to its complex cyclic structure. This can limit solubility in highly polar solvents.
  • Solvent Effects: Solubility can vary significantly with different solvents. It may be soluble in alcohols and other organic solvents, while being less soluble in nonpolar solvents.

In summary, the solubility of this compound is influenced by the balance between its polar hydroxyl groups and any potential hydrophobic regions within its intricate structure. Understanding these factors is crucial when predicting its behavior in various chemical environments.

Interesting facts

Compound Insights: A Complex Organic Molecule

This compound, with its intricate structure, exemplifies the captivating complexity that organic chemistry offers. As a multi-ringed molecule with several stereocenters, it plays an intriguing role in various biological processes. Here are some interesting facts about this fascinating compound:

  • Natural Origin: Such compounds are often derivatives of natural products and can be found in numerous organisms, including plants and fungi, playing a critical role in their chemistry and potential medicinal properties.
  • Stereochemistry: With multiple chiral centers, this compound is a great topic of study for understanding stereochemistry and its implications in drug design, as slight changes in stereochemistry can lead to drastically different biological activities.
  • Biological Significance: Compounds of similar structures are often investigated for their efficacy in pharmaceutical applications, including their potential as anti-inflammatory, anti-viral, and anti-cancer agents.
  • Complex Synthesis: The synthesis of such a molecule poses significant challenges, often requiring elaborate multi-step procedures in synthetic organic chemistry, making it a hallmark of advanced research.
  • Research Opportunities: Investigating this compound can lead students and researchers alike to explore the intersections of structure, function, and synthesis in organic compounds.

As a quote by the famous chemist Robert H. Grubbs states, "Chemistry is the science of connection." This compound serves as a prime example of how individual components can connect to create something brilliant and complex within the world of chemical sciences.

Synonyms
SCHEMBL6068
CHEMBL404811
UVYVLBIGDKGWPX-YCCXZQINSA-N
Q410968