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Simvastatin

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Identification
Molecular formula
C25H38O5
CAS number
79902-63-9
IUPAC name
5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-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, simvastatin is a solid. It is typically formulated into tablets for oral administration.
Melting point (Celsius)
139.00
Melting point (Kelvin)
412.10
Boiling point (Celsius)
431.00
Boiling point (Kelvin)
704.10
General information
Molecular weight
418.57g/mol
Molar mass
418.5730g/mol
Density
1.0423g/cm3
Appearence

Simvastatin appears as a white to off-white crystalline powder. It is often provided in a micronized form to improve absorption.

Comment on solubility

Solubility of 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-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 characteristics of 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-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 can be intriguing due to its complex structure and functional groups. Several factors influence its solubility:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that the compound may exhibit increased polarity, often enhancing solubility in polar solvents like water.
  • Hydrogen Bonding: The -OH groups are capable of strong hydrogen bonding, which can facilitate solubility in solvents that can engage in such interactions.
  • Molecular Weight: The relatively high molecular weight of the compound may limit its solubility in nonpolar solvents, hindering its passage through lipid membranes.
  • Hydrophobic Interactions: The bulky hydrophobic segments of the molecule might decrease overall solubility in aqueous environments despite the presence of polar functional groups.

Considering the interplay of these factors, it is likely that this compound demonstrates variable solubility depending on the solvent used. In general, compounds of this nature may solubilize well in alcoholic solutions or aqueous mixtures that can accommodate polar functionalities, while showing significantly lower solubility in pure organic solvents such as hexane or chloroform.

Overall, the solubility aspects of this complex compound are a balance between its hydrophilic characteristics due to hydroxyl groups and its hydrophobic structure, which could lead to an alluring profile for solubility studies.

Interesting facts

Interesting Facts about 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-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 recognized for its complex and intricate structure, belongs to a class of molecules that exhibit fascinating biological properties.

Biological Significance

  • Phytochemistry: It is derived from natural sources, suggesting a potential role in traditional medicine.
  • Antioxidant Activity: Research indicates that compounds within this class may possess strong antioxidant properties, which can be beneficial in combating oxidative stress.
  • Potential Therapeutic Uses: There is growing interest in compounds like these for their applications in treating various ailments, particularly in the fields of oncology and endocrinology.

Chemical Complexity

The structural configuration of this compound is impressive:

  • With multiple stereocenters, it showcases the importance of chirality in biological systems.
  • Its intricate polycyclic structure highlights the relationship between molecular architecture and biological function.
  • The presence of hydroxyl groups adds to the molecule's reactivity and interaction with biological targets.

Molecular Interactions

Understanding how this compound interacts with biological macromolecules is crucial for leveraging its potential. Here are some ways it may engage:

  • Hydrogen Bonding: The hydroxyl groups can participate in hydrogen bonding, enhancing solubility in biological systems.
  • Receptor Binding: It may bind to specific cellular receptors, leading to a cascade of biological effects.

In summary, the exploration of this compound opens avenues for innovative research in drug development and bioactive compounds, inviting scientists to unlock its full potential!

Synonyms
5beta,20(22)-Bufadienolide-3beta,14-diol
SCHEMBL14007456
AKOS015896786
5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-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