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Withaferin A

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Identification
Molecular formula
C28H38O6
CAS number
5119-48-2
IUPAC name
(3S,5S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
State
State

Withaferin A exists as a solid at room temperature. It is typically isolated and stored as a powder or crystalline solid.

Melting point (Celsius)
258.00
Melting point (Kelvin)
531.15
Boiling point (Celsius)
552.30
Boiling point (Kelvin)
825.45
General information
Molecular weight
470.59g/mol
Molar mass
470.5580g/mol
Density
1.2800g/cm3
Appearence

Withaferin A is a crystalline compound that appears as a white or off-white solid. It typically forms needle-like crystals. It is sensitive to air and light.

Comment on solubility

Solubility of (3S,5S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-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 is influenced by its intricate molecular structure, which introduces both hydrophilic and lipophilic characteristics. Understanding its solubility can shed light on its potential applications and interactions in various environments.

Key Factors Affecting Solubility:

  • Hydroxyl Groups: The presence of multiple hydroxyl (-OH) groups generally enhances solubility in polar solvents, such as water, due to hydrogen bonding.
  • Aliphatic Hydrocarbon Chains: The bulky hydrocarbon sections can potentially lower solubility in polar liquids while promoting solubility in non-polar solvents.
  • Functional Groups: The 6-oxopyran moiety may further complicate solubility characteristics, as different functional groups exhibit varied solvation behavior.

Given the above factors, one might find that the compound demonstrates:

  • Higher solubility in organic solvents compared to water, which can be attributed to its hydrophobic regions.
  • Moderate solubility in polar solvents, influenced by the pendulous hydroxyl groups seeking to interact with solvent molecules.
  • Potential crystallization properties that may affect its availability in solution.

In summary, the solubility of this compound is a complex interplay of its functional groups and molecular architecture, making it an intriguing subject for further research in relation to its behavior in different solvents.

Interesting facts

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

This fascinating compound, characterized by its intricate structure, belongs to the category of polycyclic compounds and presents numerous points of interest for both chemists and biologists. Here are some engaging facts:

  • Natural Origins: Many compounds similar to this structure are found in natural sources, particularly in plants, where they can play vital roles in biological functions, including medicinal properties.
  • Hydroxyl Groups: The presence of three hydroxyl groups in this compound suggests its potential as a hydrogen bond donor, which is crucial for interactions in biological systems or for developing pharmaceuticals.
  • Complexity: With multiple stereocenters, this compound exhibits chirality, which means it can exist in different configurations that may result in varying biological activities. Chiral compounds are often of particular interest in the field of drug design.
  • Carbaldehyde Group: The aldehyde functional group in the structure makes it reactive, allowing for further chemical modifications or interactions with other cellular components.
  • Structure-Activity Relationship: The complex arrangement of rings and functional groups suggests that scientists may explore how these elements influence the biological activity of the compound. Understanding these relationships is essential in medicinal chemistry.
  • Potential Applications: Due to its unique structural attributes, this compound possesses potential applications in drug development, especially targeting diseases where plant-derived compounds show promise.

Overall, this compound serves as an exquisite example of the beautiful complexity of chemistry, blending natural product chemistry with medicinal research possibilities. As we dive deeper into understanding such compounds, we might uncover new therapeutic agents to improve human health!