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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(3S,5S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5R)-3,4,5-trihydroxy-6-[[(3R,6S)-4,5,6-trihydroxy-2-methyl-tetrahydropyran-3-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

Digoxin is generally found as a solid at room temperature, typically in the form of powders or compressed into tablets for medicinal use.

Melting point (Celsius)
249.00
Melting point (Kelvin)
522.15
Boiling point (Celsius)
539.30
Boiling point (Kelvin)
812.50
General information
Molecular weight
780.94g/mol
Molar mass
780.9440g/mol
Density
1.2800g/cm3
Appearence

Digoxin appears as a white or almost white, crystalline powder. It is practically insoluble in water but freely soluble in a mixture of alcohol and water.

Comment on solubility

Solubility of 3-[(3S,5S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5R)-3,4,5-trihydroxy-6-[[(3R,6S)-4,5,6-trihydroxy-2-methyl-tetrahydropyran-3-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 solubility of complex compounds such as this one can vary widely based on several structural factors. Here are some key considerations:

  • Polarity: The presence of hydroxyl groups significantly increases the polarity of the molecule, enhancing its ability to interact with polar solvents such as water.
  • Hydrogen Bonding: With multiple hydroxyl groups, this compound has the potential for extensive hydrogen bonding, which can impact solubility in both polar and non-polar solvents.
  • Structural Complexity: The intricate structure may lead to steric hindrance, which can hinder solubility in certain solvents.
  • Temperature Dependence: Solubility can also be affected by temperature; increasing the temperature may improve solvent interaction.

It is important to note that while the theoretical considerations provide a basis for predicting solubility, practical experimental data is essential to accurately determine the solubility of this compound in various solvents. As a result, one should not assume comprehensive solubility based solely on structural analysis, but rather conduct appropriate tests to definitively establish solubility characteristics.

This demonstrates that solubility is often a nuanced topic in chemistry, with multiple variables at play that can lead to different outcomes depending on conditions.

Interesting facts

Interesting Facts about 3-[(3S,5S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5R)-3,4,5-trihydroxy-6-[[3R,6S)-4,5,6-trihydroxy-2-methyl-tetrahydropyran-3-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

This compound, a complex steroid-like structure, exhibits a multitude of both biochemical and pharmacological properties that pique the interest of scientists and researchers alike. Here are some noteworthy aspects:

  • Biological Activity: Compounds of this nature are often studied for their unique interactions with biological systems, particularly their role as potential therapeutic agents.
  • Structural Complexity: The intricate stereochemistry includes multiple chiral centers, making it a fascinating compound for organic synthesis and stereochemical studies.
  • Natural Occurrences: Many compounds related to this structure are found in nature, often derived from plant sources, hinting at their possible roles in human health and nutrition.
  • Research Opportunities: The diversity within this compound's structure opens the door for further exploration in drug development, particularly in the fields of oncology and metabolic diseases.
  • Historical Significance: Compounds similar to this one have historical relevance in traditional medicine, with claims of various health benefits that warrant modern scientific exploration.

As a chemistry student or researcher, exploring such a compound can provide insights into:

  1. Natural product synthesis: Understanding how similar compounds are synthesized in nature can guide synthetic approaches in the lab.
  2. Pharmacology: Investigating how this compound interacts with biological targets may lead to the development of new medications.
  3. Chirality and its effects: Analyzing the implications of chirality in pharmacodynamics and pharmacokinetics is crucial in drug design.

In conclusion, the exploration of 3-[(3S,5S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,5R)-3,4,5-trihydroxy-6-[[3R,6S)-4,5,6-trihydroxy-2-methyl-tetrahydropyran-3-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 not only highlights its potential importance in various fields but also serves as a compelling subject for ongoing research in organic and medicinal chemistry.