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Lovastatin

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Identification
Molecular formula
C24H36O5
CAS number
75330-75-5
IUPAC name
[(3S,5R,10S,13R,14S,16S)-3-[(2S,5S)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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-16-yl] acetate
State
State

At room temperature, Lovastatin is in a solid state.

Melting point (Celsius)
174.00
Melting point (Kelvin)
447.15
Boiling point (Celsius)
232.00
Boiling point (Kelvin)
505.15
General information
Molecular weight
404.53g/mol
Molar mass
404.5320g/mol
Density
1.1600g/cm3
Appearence

Lovastatin appears as a white, crystalline powder. It is odorless or may have a faint odor.

Comment on solubility

Solubility of the Compound

The solubility of the compound [(3S,5R,10S,13R,14S,16S)-3-[(2S,5S)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-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-16-yl] acetate can be quite complex due to its intricate molecular structure and the presence of various functional groups.

Factors Affecting Solubility

Several factors can influence the solubility of this compound:

  • Polarity: The presence of hydroxyl (-OH) groups typically increases the polarity, which can enhance solubility in polar solvents like water.
  • Molecular Size: Larger molecules often have lower solubility due to steric hindrance, which can hinder interactions with solvents.
  • Functional Groups: The methoxy (-OCH3) and furan groups may also contribute significantly to the solubility, potentially making it soluble in organic solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds can enhance solubility, particularly in polar solvents.

Solvent Compatibility

This compound may demonstrate:

  • Good Solubility: In organic solvents such as ethanol, methanol, or acetone.
  • Limited Solubility: In water due to the overall hydrophobic character imparted by the larger hydrophobic phenanthrene structure.

In conclusion, the solubility of this compound is influenced by a combination of structural elements and the nature of the solvent. It is essential to conduct specific solubility tests to determine the most suitable solvent for practical applications. As quoted, “The solubility of a compound is a reflection of its nature.” This complexity highlights the importance of understanding solubility in the context of chemical behavior and interactions.

Interesting facts

Interesting Facts about the Compound

This complex chemical compound, often referred to in the context of natural products and synthetic chemistry, offers a fascinating glimpse into the intricate world of organic molecules. Here are some engaging facts about this compound:

  • Natural Origins: The structure of this compound suggests a connection to naturally occurring steroids or terpenoids, hinting at possible biological activity and interaction with cellular processes.
  • Stereochemistry: With multiple chiral centers, the stereochemical configuration is crucial. In organic chemistry, the different spatial arrangements of its atoms can lead to vastly different properties and biological effects, emphasizing the importance of chirality in pharmacology.
  • Functional Groups: The compound features various functional groups, including hydroxyl (-OH), methoxy (-OCH₃), and an acetate (-COCH₃) group. These groups can significantly influence the compound's reactivity and solubility, leading to a variety of applications in medicinal chemistry.
  • Potential Applications: Given its structural complexity and the presence of bioactive groups, this compound is a potential candidate for investigation in the field of drug development, particularly for its possible anticancer or antimicrobial properties.
  • Structural Elucidation: Understanding this compound requires sophisticated analytical techniques such as NMR (Nuclear Magnetic Resonance) spectroscopy and Mass Spectrometry. These methods help chemists confirm the structure and elucidate the molecular dynamics involved.

In summary, the study of this compound not only underscores the beauty of organic chemistry but also showcases the potential for discovering new therapeutic agents. The intricate balance of its structure and reactivity serves as a reminder of nature's complexity and the innovative spirit of scientific inquiry.