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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(3S,5R,10R,13R,14S,17R)-3-[(2S,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-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

At room temperature, digoxin is in solid-state and typically utilized in pharmaceutical formulations.

Melting point (Celsius)
249.30
Melting point (Kelvin)
522.45
Boiling point (Celsius)
410.00
Boiling point (Kelvin)
683.15
General information
Molecular weight
780.94g/mol
Molar mass
780.9440g/mol
Density
1.0900g/cm3
Appearence

Digoxin is obtained as white to off-white crystalline powder that is very light and fluffy. The powder should be stored in well-closed containers as it is hygroscopic in nature.

Comment on solubility

Solubility of 3-[(3S,5R,10R,13R,14S,17R)-3-[(2S,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-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 this complex compound can be a challenging aspect to evaluate due to its intricate molecular structure. The presence of multiple functional groups, such as hydroxyl (–OH) and methoxy (–OCH3) moieties, suggests potential for hydrogen bonding, which may enhance solubility in polar solvents. However, the overall hydrophobic character of the tetradecahydro structure can hinder dissolution in aqueous solutions.

Factors Influencing Solubility:

  • Polar vs. Nonpolar Solvents: The solubility of this compound in water may be low, while it could be more soluble in organic solvents like ethanol or methanol.
  • Hydrogen Bonding: The –OH groups can form hydrogen bonds, increasing solubility in polar solvents.
  • Chain Length: The extensive hydrophobic carbon chain may lead to decreased solubility in water.

As such, one can expect the solubility of this compound to vary significantly:

  1. Higher solubility in: Organic solvents due to hydrophobic interactions.
  2. Lower solubility in: Aqueous environments given its large hydrophobic regions.

In practical applications, performing solubility tests in various mediums will provide a better understanding of how this compound behaves in solution. Therefore, experimentation is essential to draw definitive conclusions about its solubility profile.

Interesting facts

Interesting Facts about 3-[(3S,5R,10R,13R,14S,17R)-3-[(2S,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-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 is a fascinating example of complex organic chemistry, particularly in the realm of natural product synthesis. Known for its intricate structure, it exemplifies the **rich diversity** found in organic molecules. Here are some intriguing aspects of this compound:

  • Chirality: The compound features multiple chiral centers, specifically at the 3S and 5R positions. This chirality plays a crucial role in determining the biological activity of the molecule. Such compounds can exhibit vastly different pharmacological effects depending on their spatial arrangement.
  • Natural Sources: Many complex organic compounds similar to this one are derived from natural sources like plants and fungi. They often serve as secondary metabolites, contributing to the defense mechanisms of the organism.
  • Potential Applications: Due to its structure, this compound may have interesting applications in medicinal chemistry. Compounds with similar characteristics are often investigated for their potential as therapeutic agents in fields such as oncology and biochemistry.
  • Synthesis Challenges: The synthesis of such a complex molecule poses significant challenges, requiring innovative strategies and techniques in organic synthesis. It often involves multi-step reactions, protecting group strategies, and possibly the employment of chiral catalysts.
  • Research Significance: Exploring compounds like this one not only enhances our understanding of organic chemistry but also aids in the development of new medicinal compounds. As researchers uncover the properties and behaviors of such substances, they contribute to the broader field of pharmacology.

This compound reminds us of the **intricacy of chemistry** and the endless potential for discovery within the molecular world. As we delve deeper into its structure, we uncover not just the science behind it but the **story** of its origin and possible futures in the realm of science.

Synonyms
DTXSID90988267
3-[(6-Deoxy-3-O-methylhexopyranosyl)oxy]-14,19-dihydroxycard-20(22)-enolide