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Withanolide A

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Identification
Molecular formula
C28H38O9
CAS number
32911-49-0
IUPAC name
[(3S,5R,10S,13R,14S,16S,17R)-16-acetoxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
State
State

Withanolide A is a solid at room temperature.

Melting point (Celsius)
290.00
Melting point (Kelvin)
563.20
Boiling point (Celsius)
541.20
Boiling point (Kelvin)
814.40
General information
Molecular weight
504.62g/mol
Molar mass
504.6210g/mol
Density
1.2300g/cm3
Appearence

Withanolide A is typically a solid compound. It is part of a group of naturally occurring steroids built on an ergostane backbone. Appearance can vary depending on its form such as crystalline or powder.

Comment on solubility

Solubility Characteristics

The solubility of the compound [(3S,5R,10S,13R,14S,16S,17R)-16-acetoxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate is quite nuanced and depends on several factors:

Factors Affecting Solubility

  • Polarity: Due to the presence of hydroxyl groups and acetoxy functionalities, this compound exhibits some degree of polarity, which can enhance its solubility in polar solvents like water and alcohol.
  • Hydrophobic Regions: The extensive hydrophobic hydrocarbon framework may limit its solubility in highly polar solvents, favoring organic solvents like chloroform or dichloromethane.
  • Temperature: As with many organic compounds, increasing the temperature may also enhance solubility by increasing molecular motion and disrupting intermolecular interactions.
  • pH Sensitivity: The solubility can be influenced by the pH of the solution, especially given the presence of acidic and basic functional groups which may ionize.

Solubility Overview

In summary, the solubility of this intricate compound can be described as:

  • **Soluble** in organic solvents such as ethanol and acetone
  • **Slightly soluble** in water due to competing interactions between hydrophobic regions and polar aspects.
  • **Insoluble** in non-polar solvents due to significant hydrophilicity imparted by functional groups.

Understanding the solubility of this compound is crucial for its application in various chemical and pharmaceutical processes, influencing factors such as bioavailability and therapeutic efficacy.

Interesting facts

Interesting Facts about the Compound

This intriguing compound is a fascinating example of a complex organic molecule that showcases the intricate nature of chemical synthesis and structural diversity. Here are some intriguing aspects of this compound:

  • Structural Complexity: The compound features multiple stereocenters, denoted by its (3S, 5R, 10S, 13R, 14S, 16S, 17R) configuration. This complexity leads to a rich array of three-dimensional arrangements, critical in understanding how the compound might interact at the molecular level.
  • Bioactivity Potential: The presence of functional groups such as acetoxy and hydroxy suggests potential biological activity. Researchers often investigate compounds with similar structures for their medicinal properties, providing hope for applications in pharmaceuticals.
  • Natural Occurrence: Compounds with similar structures are frequently isolated from natural sources, particularly in plants and fungi. This compound could be a derivative of steroids or terpenes that play significant roles in biological systems.
  • Chirality and Isomerism: The numerous chiral centers give rise to enantiomers and diastereomers, which can have different biological activities. Understanding chirality in this context is essential for drug design, as the desired therapeutic effects can be highly stereospecific.
  • Synthetic Challenges: The synthesis of such complex molecules is typically challenging and may involve multiple steps, requiring expert handling of reagents and conditions to ensure the correct formation of stereoisomers.

In summary, the study of this compound is not just about its structure; it's about the broader implications for chemistry, biology, and medicinal applications. As one researcher aptly noted, "Complexity in molecular architecture often begets complexity in biological effects." This highlights the importance of investigating such compounds in depth.

Synonyms
5996-03-2
Gitoxingenin acetate
Gitoxigenin diacetate
Diacetylgitoxigenin
3,16-Diacetylgitoxigenin
3,16-O-Diacetylgitoxigenin
BRN 0066387
DTXSID40975384
3-beta,14,16-beta-Trihydroxy-5-beta-card-20(22)-enolide 3,16-diacetate
Card-20(22)-enolide, 3,16-bis(acetyloxy)-14-hydroxy-, (3-beta,5-beta,16-beta)-
4-18-00-02459 (Beilstein Handbook Reference)
3,16-Bis(acetyloxy)-14-hydroxycard-20(22)-enolide
5-beta-CARD-20(22)-ENOLIDE, 3-beta,14,16-beta-TRIHYDROXY-, 3,16-DIACETATE