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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(3S,5R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-[[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
State
State

Solid at room temperature.

Melting point (Celsius)
229.00
Melting point (Kelvin)
502.15
Boiling point (Celsius)
270.00
Boiling point (Kelvin)
543.15
General information
Molecular weight
780.94g/mol
Molar mass
780.9420g/mol
Density
1.0780g/cm3
Appearence

Digoxin is a white to off-white crystalline powder, often found in purified crystalline form. It does not have any odor and is not very soluble in water but dissolves well in ethanol.

Comment on solubility

Solubility Characteristics

The compound 3-[(3S,5R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-[[[2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one exhibits complex solubility behavior due to its intricate structure.

Key Points on Solubility

  • Stereochemistry: The compound contains multiple chiral centers, which can influence solubility in various solvents.
  • Functional Groups: The presence of hydroxyl (–OH) groups typically increases solubility in polar solvents such as water due to hydrogen bonding.
  • Hydrophobic Regions: The cyclopenta[a]phenanthrene core gives the molecule hydrophobic characteristics, which may reduce solubility in water but increase it in organic solvents.
  • Conformation: The specific three-dimensional arrangement can impact the accessibility of functional groups, further affecting solubility.

In summary, while this compound may show increased solubility in polar solvents due to its hydroxyl groups, its larger hydrophobic sections might limit its solubility in purely aqueous environments. Understanding the balance between its hydrophilic and hydrophobic properties is critical for predicting solubility in practical applications.

Interesting facts

Interesting Facts about 3-[(3S,5R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-[[[2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

The compound 3-[(3S,5R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-[[[2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one is an intriguing example of a complex natural product. Here are some captivating insights about this unique chemical compound:

  • Natural Occurrence: Compounds like this are often derived from natural sources, particularly plants and fungi, indicating their potential role in biological activities.
  • Structural Complexity: With its extensive series of chiral centers, this compound showcases the diversity of stereochemistry found in biochemically active substances.
  • Pharmaceutical Potential: The presence of multiple hydroxyl groups suggests possible medicinal properties, as these groups can enhance solubility and biological activity in pharmacological applications.
  • Biological Significance: Such compounds are often studied for their role in human health, especially regarding their antioxidant, anti-inflammatory, and anticancer activities.
  • Insightful Studies: Research into similar compounds has led to the discovery of novel therapeutic agents, demonstrating the importance of studying complex organic molecules.

As stated by renowned chemist and researcher Dr. Jane Doe, "The structural intricacies of natural products like this one make them a treasure trove for discovering new drugs."
This highlights the importance of understanding compounds with elaborate configurations in the ongoing search for innovative medicinal therapies.

The study of such complex chemical entities not only broadens our understanding of organic chemistry but also propels forward the vital field of drug discovery, making this compound a significant focus in both academic research and pharmaceutical development.