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Lovastatin

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

At room temperature, Lovastatin is a solid.

Melting point (Celsius)
174.00
Melting point (Kelvin)
447.15
Boiling point (Celsius)
669.10
Boiling point (Kelvin)
942.25
General information
Molecular weight
404.55g/mol
Molar mass
404.5450g/mol
Density
1.2000g/cm3
Appearence

Lovastatin is a white crystalline powder. It is odorless and practically insoluble in water, but freely soluble in chloroform, and insoluble in ether.

Comment on solubility

Solubility Characteristics

The compound 5-[(3S,5R,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one is characterized by several intriguing solubility properties.

Solubility Profile

As a complex polycyclic compound, its solubility largely depends on the following factors:

  • Hydroxyl Groups: The presence of multiple hydroxyl groups enhances the compound's ability to dissolve in polar solvents, particularly water.
  • Hydrophobic Regions: The polycyclic structure contains hydrophobic regions which can hinder solubility in pure aqueous solutions.
  • Organic Solvents: It is likely to have better solubility in organic solvents like ethanol, methanol, or dimethyl sulfoxide (DMSO) due to its non-polar characteristics.

General Observations

In practice, researchers may observe that:

  • The solubility in water may be limited, leading to a preference for organic solutions in laboratory settings.
  • Thermal conditions can also play a significant role, as increased temperatures often improve solubility.

Given its complex structure, it is essential to evaluate solubility through empirical methods, as the theoretical predictions may not encompass the nuances of intermolecular interactions that can affect solubility in various mediums.

Interesting facts

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

This compound belongs to a fascinating category of organic compounds known as steroidal glycosides, which are derivatives characterized by their unique cyclic structures and multiple functional groups.

Here are some intriguing aspects of this compound:

  • Natural Product: This compound can be isolated from various plants, indicating a potential role in their therapeutic properties.
  • Biological Significance: Many compounds in this class exhibit significant biological activity, which has generated interest in their applications in pharmacology.
  • Stereochemical Complexity: The multiple chiral centers present in the structure contribute to a high level of stereochemical complexity, making it essential for scientists to employ advanced techniques in stereochemistry for synthesis and analysis.
  • Potential Applications: With its unique functional groups, this compound may have prospective applications in the development of new pharmaceuticals, particularly in treating diseases due to its structural resemblance to biologically active compounds.

As a student of chemistry, understanding such compounds enhances one's knowledge of structure-activity relationships (SAR). The ability to manipulate the stereochemistry and functionalization of these compounds opens avenues for innovative drug design, ensuring that chemists are ever-inventive in exploring the vibrant chemistry of natural products.

In the words of a famous chemist, “Chemistry is the art of problem-solving,” and studying compounds like this showcases both the challenges and the beauty of organic synthesis, offering a noble journey into the heart of molecular architecture.

Synonyms
Gamabufotalin (Gamabufagin; Gamabufogenin)
AKOS040740344
AH-034/21084002