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Simvastatin

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Identification
Molecular formula
C25H38O5
CAS number
79902-63-9
IUPAC name
5-[(3S,5R,10S,12R,13S,14S,17R)-3,12,14-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

The compound is typically solid at room temperature, existing as a crystalline powder.

Melting point (Celsius)
139.00
Melting point (Kelvin)
412.15
Boiling point (Celsius)
681.20
Boiling point (Kelvin)
954.35
General information
Molecular weight
418.57g/mol
Molar mass
418.5730g/mol
Density
1.0469g/cm3
Appearence

Simvastatin typically appears as a white or off-white crystalline powder. It is practically insoluble in water and freely soluble in chloroform, methanol, and ethanol.

Comment on solubility

Solubility of 5-[(3S,5R,10S,12R,13S,14S,17R)-3,12,14-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

The solubility of this complex organic compound can largely be attributed to its unique structural characteristics, which include multiple hydroxy groups and a polycyclic ring system. Understanding the solubility behavior of such compounds can be essential in various applications, particularly in pharmaceuticals and natural products. Here are some points to consider regarding its solubility:

  • Polarity: The presence of three hydroxy groups suggests increased polarity, which typically enhances solubility in polar solvents such as water and alcohols.
  • Hydrogen bonding: The hydroxy groups can engage in hydrogen bonding with solvent molecules, which may further promote solubility.
  • Hydrophobic regions: The polycyclic structure may have hydrophobic characteristics, leading to lower solubility in aqueous solutions but potentially good solubility in organic solvents like dimethyl sulfoxide (DMSO) or ethanol.
  • Concentration effects: At higher concentrations, the formation of aggregates or complexes can alter solubility dynamics.

In conclusion, while the presence of hydroxy groups generally indicates good solubility in polar solvents, the larger molecular structure and hydrophobic portions can create a more nuanced solubility profile that may challenge solubility in strictly aqueous environments. Hence, the solubility of this compound is subject to various factors, reflecting its complex nature.

Interesting facts

Interesting Facts about 5-[(3S,5R,10S,12R,13S,14S,17R)-3,12,14-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, often encountered in discussions related to natural products, exhibits fascinating properties and biological significance. Its structure features a complicated arrangement, indicative of its role in various biological activities. Here are some noteworthy aspects:

  • Natural Origins: Many compounds like this one are derived from plant sources and can participate in essential biological processes. They often play roles in plant defense mechanisms.
  • Structural Complexity: The intricate stereochemistry, including multiple hydroxy groups and a tricyclic structure, makes the study of its synthesis and reactivity particularly challenging and intriguing.
  • Biological Activity: Research suggests that similar compounds can exhibit a range of activities including anti-inflammatory, antimicrobial, and even anticancer properties. The presence of multiple hydroxy groups can enhance its ability to interact with biological molecules.
  • Potential Applications: There is ongoing research to explore the applications of this compound in pharmaceuticals and nutraceuticals. Its structural features may provide a foundation for designing new therapeutic agents.

Conclusion

In summary, the compound's complexity and potential bioactivity make it a valuable subject of study. As researchers continue to uncover its properties, we may find new applications that can benefit medicine and agriculture. Indeed, the intricate dance of atoms within this molecular structure might hold the key to unlocking innovative solutions in the future!

Synonyms
12-beta-Hydroxybufalin [German]
BRN 0056390
12-beta-Hydroxybufalin
3-beta,12-beta,14-Trihydroxy-5-beta-bufa-20,22-dienolide
5-beta-BUFA-20,22-DIENOLIDE, 3-beta,12-beta,14-TRIHYDROXY-
4-18-00-02556 (Beilstein Handbook Reference)
DTXSID10958341
3,12,14-Trihydroxybufa-20,22-dienolide