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Misoprostol

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Identification
Molecular formula
C22H38O5
CAS number
59122-46-2
IUPAC name
4-[5-hydroxy-4-(3-hydroxyoct-1-enyl)-1-phenyl-5,6-dihydro-4H-cyclopenta[b]pyrrol-2-yl]butanoic acid
State
State

At room temperature, misoprostol is a solid.

Melting point (Celsius)
261.00
Melting point (Kelvin)
534.15
Boiling point (Celsius)
144.00
Boiling point (Kelvin)
417.15
General information
Molecular weight
382.53g/mol
Molar mass
382.5330g/mol
Density
1.0440g/cm3
Appearence

Misoprostol is a white to off-white crystalline powder. It is soluble in ethanol, methanol, and methylene chloride and has limited solubility in water.

Comment on solubility

Solubility of 4-[5-hydroxy-4-(3-hydroxyoct-1-enyl)-1-phenyl-5,6-dihydro-4H-cyclopenta[b]pyrrol-2-yl]butanoic acid (C22H38O5)

The solubility of this complex organic compound can be quite intricate, influenced by its unique structure and functional groups. Generally, the presence of multiple hydroxyl (-OH) groups suggests a propensity for hydrogen bonding with water molecules, which can enhance its solubility in polar solvents. However, the large hydrophobic hydrocarbon chains may counteract this effect to some extent.

Key Factors Influencing Solubility:

  • Hydroxyl Groups: The compound contains hydroxyl groups which typically increase solubility in water due to their ability to form hydrogen bonds.
  • Hydrophobic Regions: The long hydrocarbon tail may create significant hydrophobic interactions that limit solubility in aqueous solutions.
  • Steric Hindrance: The bulky cyclopenta[b]pyrrol moiety might further complicate solubility due to steric factors inhibiting interaction with solvent molecules.
  • pH Dependency: Being a carboxylic acid, its solubility can vary with pH, as it may ionize to form a more soluble anion in basic conditions.

In general, it is expected that this compound may demonstrate moderate solubility in organic solvents like ethanol or DMSO, while its solubility in water could be influenced by the aforementioned factors. Thus, empirical testing is recommended to quantify its solubility characteristics effectively.

Interesting facts

Interesting Facts about 4-[5-hydroxy-4-(3-hydroxyoct-1-enyl)-1-phenyl-5,6-dihydro-4H-cyclopenta[b]pyrrol-2-yl]butanoic acid

This compound, with its intricate structure, belongs to a fascinating class of organic molecules known for their diverse biological activities. Here are some intriguing aspects of this particular compound:

  • Complex Structure: The compound features a cyclopenta[b]pyrrole core, which is a fused bicyclic structure that contributes to its unique chemical properties. Such frameworks are often associated with interesting biological functionalities.
  • Functional Groups: The presence of multiple hydroxyl groups (–OH) in its structure typically enhances solubility in polar solvents and can significantly affect the compound's reactivity. This may also imply potential interactions with biological systems.
  • Biological Relevance: Compounds of this nature have been investigated for their potential as pharmaceutical agents. Their complex structure often allows for interactions at multiple biological targets, making them of interest in the fields of drug discovery and development.
  • Natural Products: Many similar compounds are derived from natural products, emphasizing their importance in traditional medicine and modern therapeutics. Understanding their mechanisms can lead to novel drug discoveries.
  • Research Potential: The structural features of this compound may provide a rich platform for synthetic chemists to explore modifications that can enhance potency, selectivity, and pharmacokinetics.

As a chemistry student or researcher, exploring the properties and potential applications of such compounds can lead to significant insights in both organic chemistry and medicinal applications. The challenges and possibilities surrounding their synthesis and functionalization can inspire innovative research endeavors.