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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
3-[(3S,5R,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)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

Digitoxin is typically found as a solid at room temperature.

Melting point (Celsius)
248.00
Melting point (Kelvin)
521.15
Boiling point (Celsius)
345.80
Boiling point (Kelvin)
618.95
General information
Molecular weight
765.96g/mol
Molar mass
765.9580g/mol
Density
1.2800g/cm3
Appearence

Digitoxin appears as a white crystalline powder. It is practically tasteless.

Comment on solubility

Solubility Characteristics

The compound with the intricate structure of 3-[(3S,5R,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)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 presents an interesting case for solubility due to its complex organic structure. Its solubility can be influenced by various factors such as:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that the compound may possess some polar characteristics, which generally enhance solubility in polar solvents like water.
  • Hydrophobic regions: However, the bulky hydrocarbon framework may create hydrophobic regions that could limit solubility in non-polar solvents.
  • Temperature: Increased temperature might improve solubility as kinetic energy allows for better interactions between solvent and solute molecules.
  • pH Dependence: The ionization of hydroxyl groups under varying pH conditions could further play a role in the solubility dynamics of this compound.

In summary, the solubility of this compound is likely to be moderate in polar solvents while potentially limited in non-polar environments. Understanding these solubility characteristics is crucial for applications in pharmaceuticals and material sciences, where dissolution behavior can affect bioavailability and efficacy.

Interesting facts

Interesting Facts about 3-[(3S,5R,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)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 is a fascinating example of a highly complex and structurally intricate natural product, often encountered in the realms of medicinal chemistry and pharmacology. Here are some engaging insights:

  • Structural Complexity: The compound features multiple stereogenic centers, which contribute to its three-dimensional shape and influence its biological activity.
  • Natural Product: Many compounds similar to this one are derived from natural sources, which makes them valuable in drug discovery and development.
  • Biological Activity: The presence of hydroxyl groups in its structure often confers significant bioactivity, making it a subject of interest in medicinal chemistry for its potential therapeutic applications.
  • Chemical Interactions: This compound may participate in various chemical interactions, which are critical for its efficacy in biological systems.
  • Synthesis Challenges: The intricate structure presents challenges in synthetic chemistry, often necessitating innovative synthetic pathways and techniques for preparation.

As scientists continue to explore the realm of complex natural products like this one, the pursuit of understanding their mechanisms of action and potential medicinal benefits remains at the forefront of research initiatives. The study of such compounds not only expands the chemical toolkit available to researchers but also deepens our understanding of the intricate relationships between structure and activity in biologically active molecules.

Synonyms
Digoxigenin-beta-D-glucosid
25817-75-8
RefChem:1083570
Digoxigenin-beta-D-glucosid [German]
BRN 0071194
12-beta,14-Dihydroxy-3-beta-((beta-D-glucopyranosyl)oxy)-5-beta-card-20(22)-enolide
5-beta-Card-20(22)-enolide, 3-beta-((beta-D-glucopyranosyl)oxy)-12-beta,14-dihydroxy-
DTXSID60948717
3-(Hexopyranosyloxy)-12,14-dihydroxycard-20(22)-enolide