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Monacolin K (Lovastatin)

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Identification
Molecular formula
C24H36O5
CAS number
75330-75-5
IUPAC name
5-[(3S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
State
State

At room temperature, Monacolin K is typically in the form of a solid.

Melting point (Celsius)
174.00
Melting point (Kelvin)
447.15
Boiling point (Celsius)
712.00
Boiling point (Kelvin)
985.15
General information
Molecular weight
404.55g/mol
Molar mass
404.5440g/mol
Density
1.2000g/cm3
Appearence

Monacolin K, also known as Lovastatin, is a white, crystalline powder. It can sometimes appear as a creamy white to off-white solid depending on purity.

Comment on solubility

Solubility of 5-[(3S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

The solubility of complex organic compounds like 5-[(3S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one can be quite intricate and is influenced by various factors:

  • Molecular Structure: The presence of hydroxyl (-OH) groups enhances hydrophilicity, leading to potential solubility in polar solvents such as water.
  • Polarity: If the molecule has both polar and nonpolar regions, it can exhibit differential solubility in various solvents, such as being soluble in organic solvents and less so in aqueous solutions.
  • Hydrogen Bonding: The compound's ability to form hydrogen bonds can significantly affect its solubility, particularly in water.
  • Temperature: Increasing temperature typically improves solubility for many compounds, making it a critical factor to consider in experimental applications.

In general, it can be noted that compounds with multiple hydroxyl groups, like this one, tend to be more soluble in water than their counterparts lacking these features. However, the large and complex structure may also lead to challenges in achieving optimum solubility.

Understanding these factors is essential for predicting the behavior of chemical compounds in different environments.

Interesting facts

Interesting Facts about 5-[(3S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

This compound represents a fascinating intersection of organic chemistry and biological activity, often drawing attention for its structural complexity and potential applications in medicinal chemistry. Here are some engaging facts about this unique molecule:

  • Structural Intricacies: The molecule features a multi-ring system with numerous stereocenters, making its synthesis a remarkable achievement in organic chemistry.
  • Biological Significance: Compounds of this general class have demonstrated various biological activities, including anti-cancer, anti-inflammatory, and anti-viral properties, making them significant in pharmaceutical research.
  • Natural Occurrence: Similar molecules are often derived from natural sources, particularly plants, suggesting an evolutionary role in protecting against environmental stresses.
  • Chirality: The presence of multiple stereocenters indicates chirality, which is crucial because the 3D orientation of the molecule can influence its biological efficacy and interactions in the body.
  • Potential Synthetic Pathways: The synthesis of such complex molecules often involves multi-step reactions, showcasing the creativity and innovation in modern synthetic methodologies, including asymmetric synthesis and organocatalysis.
  • Application in Drug Development: Understanding the mechanism of action and improving the efficacy of similar compounds continue to be a major focus in the field of medicinal chemistry.

In summary, this compound is not just a formula; it represents a rich field of research and application in science. With its structural complexity and potential medicinal benefits, the study of such compounds offers endless avenues for exploration and discovery.