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Rosuvastatin

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Identification
Molecular formula
C22H28FN3O6
CAS number
147098-20-2
IUPAC name
4-[(3R,5S)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
State
State

Rosuvastatin is solid at room temperature. It is commonly administered in the form of oral tablets, indicating its solid state as a powder or crystalline form when not in pharmaceutical preparation.

Melting point (Celsius)
122.30
Melting point (Kelvin)
395.45
Boiling point (Celsius)
760.13
Boiling point (Kelvin)
1 033.13
General information
Molecular weight
481.54g/mol
Molar mass
481.5410g/mol
Density
1.2870g/cm3
Appearence

Rosuvastatin is typically found as a white to off-white powder or crystalline solid. It is practically insoluble in water and only slightly soluble in octanol. It is used orally in tablet form for medical purposes. Its appearance in pharmaceutical forms can vary but generally consists of small, round, and coated tablets.

Comment on solubility

Solubility of 4-[(3R,5S)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

The solubility characteristics of 4-[(3R,5S)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid can be intriguing due to its complex structural features.

In general, the solubility of this compound is influenced by several key factors, including:

  • Polarity: The presence of hydroxyl (-OH) groups tends to enhance the solubility in polar solvents like water.
  • Hydrophobic character: The large hydrophobic hydrocarbon framework might limit solubility in aqueous environments.
  • pH levels: As a carboxylic acid, its solubility can vary significantly with changes in pH, affecting its protonation state.
  • Temperature: Increasing temperature generally improves solubility for many organic compounds.

In practical terms, it may be expected that:

  • The compound exhibits moderate solubility in organic solvents.
  • It might show limited solubility in water, particularly at lower temperatures.

Overall, understanding the solubility behavior of this compound is essential for its applications in various chemical and biological fields.

Interesting facts

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

This compound, often associated with complex biochemical processes and pharmacological applications, has several intriguing aspects that make it a topic of interest in the field of chemistry.

Structural Significance

  • Stability and Conformation: The intricate structure of this compound, with multiple stereocenters, contributes to its stability and unique conformational possibilities.
  • Functional Groups: The presence of hydroxyl (-OH) and carbonyl (=O) functional groups plays a crucial role in its reactivity and interactions with biological systems.

Biological Implications

  • Potential Therapeutic Uses: Compounds similar to this one have been explored for their pharmaceutical properties, particularly in areas such as anti-inflammatory or anti-cancer treatments.
  • Steroid-Like Activity: Given its structural similarities to steroidal compounds, it may exhibit hormonal functions or modulate biochemical pathways.

Challenges in Synthesis

Synthesizing a molecule of such complexity presents a significant challenge for chemists. The multifaceted stereochemistry requires:

  • Selective Reactions: Careful selection of reagents and conditions to achieve desired stereochemical outcomes.
  • Purification Techniques: Advanced methods to isolate and purify the compound from reaction mixtures, ensuring high yields of the target molecule.

Conclusion

In summary, 4-[(3R,5S)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid is a fascinating compound that exemplifies the complex relationship between chemical structure and biological function. Its study not only enhances our understanding of natural products but also paves the way for future innovations in medicinal chemistry.