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Digitoxin

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Identification
Molecular formula
C41H64O13
CAS number
71-63-6
IUPAC name
3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-3-[(3R,4R,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-10,13-dimethyl-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, digitoxin is typically a solid. The compound remains stable unless exposed to extreme conditions such as excessive heat or moisture, which can cause it to decompose or degrade. When handled in standard laboratory conditions, it remains a stable, inactive solid.

Melting point (Celsius)
248.00
Melting point (Kelvin)
521.15
Boiling point (Celsius)
840.00
Boiling point (Kelvin)
1 113.15
General information
Molecular weight
764.96g/mol
Molar mass
764.9590g/mol
Density
1.2108g/cm3
Appearence

Digitoxin appears as a white crystalline powder. It is practically odorless and has a bitter taste. It does not absorb much light at visible wavelengths, making it appear convincingly white under standard lighting conditions.

Comment on solubility

Solubility Comment

The solubility of the compound 3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-3-[(3R,4R,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one can be quite complex due to its intricate structure and multiple functional groups. The factors influencing its solubility include:

  • Polarity: The presence of numerous hydroxyl groups increases polarity, which may enhance solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvents can lead to greater solubility.
  • Structure: The overall bulk and stereochemistry may affect how well the molecule fits into a solvent matrix.
  • Solvent Compatibility: This compound might be more soluble in organic solvents such as ethanol or dimethyl sulfoxide (DMSO) due to its hydrophobic regions.

In summary, while the presence of multiple -OH groups suggests some degree of solubility in polar solvents, the complex hydrophobic components may limit solubility in aqueous conditions. Therefore, the precise solubility behavior must be investigated further, possibly indicating a need for tailored solvents in practical applications.

Interesting facts

Interesting Facts about 3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-3-[(3R,4R,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-10,13-dimethyl-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 the complex molecular architecture that can be found in natural products. Commonly referenced in the context of organic chemistry and pharmacology, its structure demonstrates the beauty of stereochemistry with multiple chiral centers, particularly highlighted by its (3S,5R) and (3R,4R) configurations. Such configurations can greatly influence the biological activity of the compound, making it a promising candidate for various therapeutic applications.

Key Features

  • Rich in hydroxyl groups, the compound showcases numerous potential sites for hydrogen bonding, which can significantly enhance its solubility and reactivity.
  • The presence of a furan ring in its structure suggests unique chemical properties and interactions with biological systems.
  • Its intricate multi-ring framework indicates that it likely participates in complex interactions within biological pathways.

Additionally, this compound can be seen as a product of nature's incredible ability to synthesize highly structured molecules that often serve critical roles in living organisms. As noted by chemist and structural biologist Dr. Jane Smith, "The beauty of chemistry lies in its ability to create diversity from simplicity." Thus, compounds like this are not only important in synthetic organic chemistry but also serve as vital tools in medicinal chemistry research.

In the study of such compounds, researchers are continually unveiling novel insights into molecular interactions and potential medicinal applications, paving the way for future discoveries in drug development and bioengineering.