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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-[(2S,5S)-3,4,5-trihydroxy-6-methyl-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

At room temperature, digitoxin is a solid.

Melting point (Celsius)
259.00
Melting point (Kelvin)
532.15
Boiling point (Celsius)
302.00
Boiling point (Kelvin)
575.15
General information
Molecular weight
764.95g/mol
Molar mass
764.9470g/mol
Density
1.3000g/cm3
Appearence

Digitoxin appears as white to off-white crystalline powder. It is practically tasteless and odorless.

Comment on solubility

Solubility of 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-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

This compound, despite its complex structure, exhibits notable solubility characteristics that may vary based on several factors. Understanding its solubility involves considering the following aspects:

  • Polarity: The presence of multiple hydroxyl groups in the molecule enhances its polarity, likely increasing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The potential for extensive hydrogen bonding between the hydroxyl groups and solvent molecules can lead to improved solubility profiles.
  • Hydrophobic Regions: Conversely, the hydrophobic parts of the compound could hinder solubility in polar solvents, suggesting limited solubility in non-polar environments.
  • pH Dependency: The solubility may also be influenced by the pH of the solution, impacting the ionization state of certain functional groups.

In summary, while this complex molecule may show promising solubility in polar solvents, its behavior in various solvents may necessitate further empirical investigation. As stated, “The solubility of a compound is significantly affected by its molecular architecture and the nature of the solvent.” Hence, experimental data are crucial for a comprehensive understanding of its solubility attributes.

Interesting facts

Interesting Facts about 3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-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

This fascinating compound is a member of the class of compounds known as steroidal glycosides, a structural category that showcases a unique combination of steroid frameworks and sugar moieties. Its complex architecture contributes to strong biological activities, often resulting in significant pharmacological effects.

Biological Significance

  • Medicinal Properties: This compound has been studied for its potential therapeutic applications, particularly in the realms of cancer research and cardiovascular health.
  • Natural Sources: Many compounds similar in nature are isolated from various plants, leading to significant interest as potential natural remedies.
  • Mechanism of Action: Research suggests that it may interact with specific biological pathways, influencing cell signaling and metabolic processes.

Chemical Structure Insight

This compound features a remarkable structural complexity, including multiple hydroxyl groups, which often enhance its reactivity and ability to form hydrogen bonds. This can lead to increased solubility and bioavailability in biological systems. The presence of the tetrahydropyran ring, characteristic of many carbohydrate derivatives, links it to various metabolic pathways.

Applications in Research

Due to its intricate design and inherent properties, it serves as a prime candidate for drug development. Its multifaceted interactions make it a focal point for ongoing studies aimed at elucidating its full potential:

  • Investigating its synergistic effects with other compounds.
  • Exploring its role in enzyme inhibition.
  • Assessing its safety and efficacy in clinical trials.

In conclusion, this compound exemplifies the intersection of chemistry and biology, embodying the continuous quest in the scientific community to discover molecules that can lead to groundbreaking therapies and health improvements.

Synonyms
Convallatoxol
3253-62-1
3-[(3S,5S,10R,13R,14S,17R)-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2S,5S)-3,4,5-trihydroxy-6-methyloxan-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
Perconval
Mannopyranoside, strophanthidol-3 6-deoxy-, alpha-L-
DTXSID50954261
UQEKVLJMBGSQGS-TXWZKFBRSA-N
5-beta-Card-20(22)-enolide, 3-beta-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,14,19-trihydroxy-
3-[(6-Deoxyhexopyranosyl)oxy]-5,14,19-trihydroxycard-20(22)-enolide