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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
[(3S,5R,10S,12R,13S,14S,17R)-12-formyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] formate
State
State
Digitoxin is a solid at room temperature.
Melting point (Celsius)
245.00
Melting point (Kelvin)
518.15
Boiling point (Celsius)
940.00
Boiling point (Kelvin)
1 213.15
General information
Molecular weight
765.01g/mol
Molar mass
764.9600g/mol
Density
1.2300g/cm3
Appearence
Digitoxin is typically found in crystalline form and it may also appear as a white powder. It dissolves moderately well in ethanol but is nearly insoluble in water.
Comment on solubility

Solubility Characteristics

The solubility of the compound [(3S,5R,10S,12R,13S,14S,17R)-12-formyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] formate is influenced by several factors. Understanding its solubility is crucial for practical applications in pharmaceuticals, chemical synthesis, and material science.

Factors Affecting Solubility

Several key aspects determine the solubility of this particular compound:

  • Polarity: The presence of polar functional groups such as formyloxy and hydroxy can enhance solubility in polar solvents, while the overall hydrophobic structure may limit its solubility in water.
  • Hydrogen Bonding: The ability to form hydrogen bonds can facilitate solvation in appropriate solvents, particularly those with hydroxyl or carbonyl groups.
  • Temperature: Solubility typically increases with temperature; hence, dissolving this compound may require heating, especially in less polar solvents.
  • pH of the solution: Changes in pH can affect the ionization of functional groups, thereby influencing solubility.

General Insights

In general, this compound is expected to have:

  • Insolubility in Water: The hydrophobic nature of its backbone suggests poor water solubility.
  • Soluble in Organic Solvents: Higher solubility is anticipated in organic solvents such as ethanol, methanol, or acetone due to the molecule's overall structure and functional groups.

In conclusion, while the complex structure poses challenges, understanding the functional dynamics allows chemists to predict and enhance the solubility of this fascinating compound in various media.

Interesting facts

Interesting Facts about the Compound

This compound, known for its intricate structure, exemplifies the complexity often found in organic chemistry. It belongs to a class of compounds known as natural products, which are crucial in the development of pharmaceuticals. Here are some fascinating aspects:

  • Natural Origins: Compounds like this one are often derived from plant sources, leading to potential medicinal properties. Exploration of their sources can yield insights into traditional remedies.
  • Functional Groups: The presence of multiple functional groups, such as the formyloxy and hydroxy groups, contributes to the compound's reactivity and biological activity. These groups often participate in key chemical reactions.
  • Stereochemistry: The specific stereochemistry (e.g., the designation of S and R configurations) plays a critical role in determining the compound’s biological interactions. This stereochemical purity can influence efficacy and safety in therapeutic applications.
  • Oxofuran Moiety: The incorporation of the 5-oxo-2H-furan-3-yl unit is of particular interest because it enhances the potential for biological activity. Such furan derivatives are often linked to various pharmacological effects.
  • Research Potential: Scientists are keenly interested in compounds like this one due to their potential in drug discovery. Research into their mechanisms of action can uncover novel therapies for various diseases.

As we delve deeper into the study of such compounds, it becomes evident that the world of organic chemistry is not just about understanding structures but also about recognizing their significance in nature and medicine. As one researcher wisely noted, "The beauty of chemistry lies in its complexity and the patterns that emerge from it."

Synonyms
3-12-Formyl-digoxigenin
1256-24-2
3-beta,12-beta,14-Trihydroxy-5-beta-card-20(22)-enolide 3,12-diformate
5-beta-CARD-20(22)-ENOLIDE, 3-beta,12-beta,14-TRIHYDROXY-, 3,12-DIFORMATE
Card-20(22)-enolide, 3,12-bis(formyloxy)-14-hydroxy-, (3-beta,5-beta,12-beta)-
DTXSID40925182
3,12-Bis(formyloxy)-14-hydroxycard-20(22)-enolide