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Digitoxin

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

Digitoxin is typically found in a solid crystalline state at room temperature.

Melting point (Celsius)
255.00
Melting point (Kelvin)
528.15
Boiling point (Celsius)
270.00
Boiling point (Kelvin)
543.15
General information
Molecular weight
765.95g/mol
Molar mass
765.9530g/mol
Density
1.3163g/cm3
Appearence

Digitoxin is a white, crystalline, odorless compound that has a bitter taste. It is usually found in solid form as a crystalline powder.

Comment on solubility

Solubility of 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-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 is influenced by its complex structure, which includes multiple hydroxyl groups that are capable of forming hydrogen bonds with water. As such, we can anticipate the following characteristics:

  • Solvent Interaction: The presence of numerous hydroxyl (-OH) groups typically suggests enhanced solubility in polar solvents like water.
  • Hydrophobic Regions: However, the bulkiness of the core structure may hinder solubility in non-polar solvents due to steric factors.
  • Potential for Dissolution: The furanone moiety can provide some degree of polarity, aiding in solubility under specific conditions.

In summary, while the compound demonstrates potential solubility in polar solvents due to its functional groups, its overall solubility will heavily depend on the interactions between its extensive functional groups and the solvent used. Therefore, empirical solubility data would be crucial for deriving precise information about its behavior in various solvents.

Interesting facts

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

The compound with the name 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one is a fascinating example of complex organic chemistry. Here are several intriguing points about this compound:

  • Steric Complexity: The compound features multiple stereocenters, indicating a significant level of stereochemical complexity, which can greatly influence its biological activity and interaction with enzymes.
  • Natural Product Derivation: Compounds of this structural type are often associated with natural products, particularly those derived from plant secondary metabolites, suggesting potential therapeutic applications.
  • Potential in Medicinal Chemistry: Due to its unique functional groups and structural characteristics, this compound may possess pharmacological properties, making it a candidate for further biological evaluation.
  • Joining of Diverse Functionalities: The presence of hydroxyl groups and furan rings highlights the compound’s versatility in forming hydrogen bonds, which is crucial for interactions at the molecular level.
  • Synthetic Challenge: The intricate synthesis required to construct such a compound can offer valuable insights into advanced organic synthesis techniques and methods for the creation of complex molecules.
  • Research Significance: Continued study of such compounds can lead to discoveries in drug design, development of synthetic pathways, and enhancement of our understanding in areas like biochemistry and pharmacognosy.

This compound is not just a chemical entity; it is a gateway to exploring the intricate relationships between molecular structure and biological function. As research in chemistry continues to evolve, the study of such complex compounds remains indispensable in the quest for new therapeutics and understanding of biochemical processes.

Synonyms
Strophanthidol-D-glucose
16479-53-1
BRN 0071908
3-beta-((Glucopyranosyl)oxy)-5,14,19-trihydroxy-5-beta-card-20(22)-enolide
4-18-00-03095 (Beilstein Handbook Reference)
DTXSID80936994
5-beta-CARD-20(22)-ENOLIDE, 3-beta-((D-GLUCOPYRANOSYL)OXY)-5,14,19-TRIHYDROXY-
3-(Hexopyranosyloxy)-5,14,19-trihydroxycard-20(22)-enolide