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Ouabain

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Identification
Molecular formula
C29H44O12
CAS number
630-60-4
IUPAC name
(3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
State
State

Ouabain is in a solid state at room temperature.

Melting point (Celsius)
195.00
Melting point (Kelvin)
468.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
728.83g/mol
Molar mass
728.8330g/mol
Density
1.4400g/cm3
Appearence

Ouabain appears as a colorless to white crystalline solid. It is odorless and has a bitter taste.

Comment on solubility

Solubility of (3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

The solubility of this complex compound can be quite intriguing due to its multifaceted structure. Here are some key insights regarding its solubility:

  • Polarity: Its numerous hydroxyl groups suggest enhanced polarity, which typically increases solubility in polar solvents like water.
  • Hydrogen Bonding: The presence of -OH groups allows for extensive hydrogen bonding with solvent molecules, potentially favouring solubility.
  • Hydrophobic Regions: The dodecahydro-1H-cyclopenta[a]phenanthrene moiety introduces a hydrophobic character, which may lead to poor solubility in highly polar solvents and better solubility in organic solvents.
  • Solvent Dependence: Its solubility might vary significantly depending on the solvent used, with potential variability in solubility between water, ethanol, and other organic solvents.

In summary, while this compound has the potential for solubility in polar solvents due to its hydroxyl functional groups, its overall solubility behavior is complex and dependent on the balance between its hydrophilic and hydrophobic characteristics. Understanding this balance is crucial for predicting solubility trends and potential applications in various fields.

Interesting facts

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

This complex organic compound is a fascinating example of the intricate structures that can be formed through natural processes. Here are some key points that explore its unique characteristics:

  • Structural Diversity: The compound features a highly branched structure, which is indicative of its biological complexity. It contains multiple functional groups such as hydroxyl and aldehyde groups that greatly influence its reactivity and potential biological activity.
  • Natural Sources: Compounds of this nature are often derived from natural sources, particularly plants, and are studied for their medicinal properties. This includes potential anti-inflammatory, antibacterial, and anti-tumor activities, making them of great interest in pharmacology.
  • Chirality: The presence of multiple stereocenters (as indicated by the extensive use of stereochemical descriptors) adds to the compound's chirality, which can lead to unique biological activities based on the orientation of the atoms in space.
  • Research Implications: The complexity of this molecule provides a rich vein for research in synthetic organic chemistry, where chemists aim to replicate such sophisticated structures in the lab. Understanding how these compounds can be synthesized may lead to the development of new pharmaceuticals.

As stated in a research paper, “The intricacies of natural products often lead to significant breakthroughs in drug design and development.” This compound is a prime example of how uncovering the mysteries of organic chemistry can yield valuable insights for therapeutic applications.

In summary, the exploration of this compound not only enhances our understanding of chemical structures but also opens doors to innovations in medicine and biotechnology. It serves as a reminder of chemistry’s profound role in nature and human health.

Synonyms
Strophanthidin-D-xylose
15596-26-6
Strophanthidin-beta-d-xyloside
5,14-Dihydroxy-3-beta-((D-xylopyranosyl)oxy)-19-oxo-5-beta-card-20(22)-enolide
DTXSID90935332
5-beta-CARD-20(22)-ENOLIDE, 5,14-DIHYDROXY-3-beta-((D-XYLOPYRANOSYL)OXY)-19-OXO-
5,14-Dihydroxy-19-oxo-3-(pentopyranosyloxy)card-20(22)-enolide