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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(3S,5S,10R,12R,13S,14S,17R)-3,5,12,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
State
State

At room temperature, digoxin is a solid.

Melting point (Celsius)
240.00
Melting point (Kelvin)
513.15
Boiling point (Celsius)
355.00
Boiling point (Kelvin)
628.15
General information
Molecular weight
780.95g/mol
Molar mass
780.9480g/mol
Density
1.2600g/cm3
Appearence

Digoxin is a white crystalline powder. It is practically insoluble in water, slightly soluble in ethanol, and freely soluble in chloroform. It is known for its characteristic bitter taste.

Comment on solubility

Solubility of 3-[(3S,5S,10R,12R,13S,14S,17R)-3,5,12,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

The solubility of this compound, with its complex structure, is an intriguing subject that often reflects its molecular interactions. Given the presence of multiple hydroxyl groups, which are polar, we can anticipate certain solubility characteristics:

  • Hydrophilicity: The hydroxyl (-OH) groups can engage in hydrogen bonding with water, enhancing solubility in aqueous environments.
  • Hydrophobic interactions: The extensive hydrocarbon backbone may impart hydrophobic characteristics, potentially decreasing solubility in polar solvents.
  • Importance of pH: The solubility may also vary with pH due to the potential ionization of hydroxyl groups, affecting the compound's overall polarity.

In conclusion, when evaluating the solubility of this compound, it is crucial to consider:

  1. The balance between hydrophilic and hydrophobic regions.
  2. The influence of environmental factors such as temperature and pH.
  3. The potential for solubilization techniques if solubility proves problematic.

To summarize, while the compound may exhibit some degree of solubility in polar solvents due to its hydroxyl groups, its overall solubility behavior will undoubtedly be complex and highly dependent on the molecular interactions at play. Understanding these interactions is key to manipulating the solubility for various applications.

Interesting facts

Interesting Facts about 3-[(3S,5S,10R,12R,13S,14S,17R)-3,5,12,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

This complex compound is a fascinating example of steroid-like structures that showcase the rich diversity found in organic chemistry. Its intricate molecular arrangement and configure present several interesting points:

  • Natural Sources: Compounds of this nature are often products of biological systems. Many steroid derivatives are found in plants and animals, indicating their potential roles in significant biological functions.
  • Structural Variety: The extensive number of chiral centers (notably, this compound has multiple stereocenters) allows for several stereoisomers to exist, each potentially exhibiting different biological activities and properties.
  • Biological Significance: Some of these types of compounds are known to have *hormonal functions* or act as precursors to various natural products such as vitamins and sterols, signaling their importance in metabolism and health.
  • Synthetic Challenges: The synthesis of such a molecule can be extraordinarily challenging due to its complex multi-ring structure and the presence of multiple functional groups, which may require advanced and innovative synthetic techniques.
  • Applications in Medicine: Understanding the structure-activity relationship of molecules like this can lead to the development of new pharmaceutical agents that could provide therapeutic benefits, particularly in areas such as oncology or hormone therapies.

This compound's rich structural detail provides a great opportunity for *research and discovery.* As a student or scientist, exploring such intricate compounds may reveal not only their beauty but also their potential in solving real-world problems within medicinal chemistry.

In the realm of organic chemistry, as we continue to investigate the structure and properties of complex compounds, we may uncover unprecedented applications and benefits that could significantly impact both science and health.

Synonyms
3,5,12,14,19-Pentahydroxycard-20(22)-enolide
DTXSID90940921