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Digitoxigenin

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Identification
Molecular formula
C23H34O4
CAS number
143-62-4
IUPAC name
3-[(3S,5S,10R,13R,14S,17R)-3,14-dihydroxy-10-(hydroxymethyl)-13-methyl-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, digitoxigenin is typically in a solid state, manifesting as a powder or fine crystals. It is stable under standard conditions of temperature and pressure.

Melting point (Celsius)
253.00
Melting point (Kelvin)
526.15
Boiling point (Celsius)
187.00
Boiling point (Kelvin)
460.15
General information
Molecular weight
402.55g/mol
Molar mass
402.5530g/mol
Density
1.2600g/cm3
Appearence

Digitoxigenin appears as a white or almost white crystalline powder. It can also be described in terms of its crystalline structure with reflection properties that give it a particular sheen under light.

Comment on solubility

Solubility of 3-[(3S,5S,10R,13R,14S,17R)-3,14-dihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

The solubility of complex organic compounds like 3-[(3S,5S,10R,13R,14S,17R)-3,14-dihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one can vary significantly based on several factors. This specific compound contains multiple hydroxyl groups and a furan moiety, suggesting a potential for enhanced solubility in polar solvents due to hydrogen bonding influences.

Here are some key considerations regarding its solubility:

  • Polarity: The presence of multiple hydroxyl groups usually contributes to increased polarity, which might enhance solubility in polar solvents like water.
  • Hydrogen Bonding: Hydroxyl groups can engage in hydrogen bonding with solvent molecules, a critical factor in solubility dynamics.
  • Hydrophobic Interactions: The tetradecahydrocyclopenta structure may introduce hydrophobic effects that could limit solubility in highly polar solvents.
  • Solvent Choice: Solubility is often solvent-dependent; this compound may exhibit greater solubility in organic solvents such as alcohols or dimethyl sulfoxide (DMSO).

In conclusion, while one can estimate certain solubility behaviors based on structural features, experimental determination is crucial to accurately characterize the solubility of this compound in different solvents. As the saying goes, “The proof of the pudding is in the eating”—meaning practical solubility tests provide the most reliable insights.

Interesting facts

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

This fascinating compound is an example of a complex natural product with a unique structure that displays a rich array of functional groups and stereochemistry. Here are some key points of interest:

  • Natural Product: This compound is part of a class of molecules derived from natural sources, often found in plants or fungi, which are typically characterized by their intricate structures and biological activities.
  • Stereochemistry: The stereochemical configuration of this compound is particularly worth noting. The specific arrangement of the four chiral centers greatly influences its chemical and biological properties.
  • Bioactivity: Compounds similar to this one have been studied for their potential pharmacological effects, including anticancer, antimicrobial, and anti-inflammatory activities. Their mechanism of action often involves interactions with specific biological targets, making them an important topic of research in medicinal chemistry.
  • Research Potential: Due to its complex structure, there is significant interest in the synthetic pathways and modification of this compound to enhance its efficacy or selectivity for certain biological targets.
  • Functional Groups: The presence of hydroxyl (-OH) groups in the structure enhances hydrogen bonding capabilities, potentially increasing solubility and reactivity, which can be pivotal in biological interactions.

As a student or researcher in chemistry, exploring such compounds can provide deep insights into organic synthesis, medicinal chemistry, and the chemistry of natural products. Understanding the structure-function relationship in these interesting compounds allows scientists to design and develop new therapies based on known compounds.