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Lovastatin

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

Lovastatin is typically found in a solid state at room temperature.

Melting point (Celsius)
174.00
Melting point (Kelvin)
447.15
Boiling point (Celsius)
518.10
Boiling point (Kelvin)
791.25
General information
Molecular weight
404.55g/mol
Molar mass
404.5400g/mol
Density
1.2000g/cm3
Appearence

Lovastatin appears as a white or off-white, crystalline powder which is practically insoluble in water but soluble in ethanol, methanol, and chloroform.

Comment on solubility

Solubility of 5-[(3S,5R,10R,13R,14S,17R)-3-[(2R,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-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 complex organic compounds, such as 5-[(3S,5R,10R,13R,14S,17R)-3-[(2R,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one, can vary significantly based on several factors:

  • Polarity: The presence of hydroxyl groups (-OH) can increase solubility in polar solvents, such as water, while the hydrophobic portions may lead to reduced solubility.
  • Hydrogen Bonding: The ability to form hydrogen bonds can enhance interactions with solvents, thus affecting solubility.
  • Temperature: Generally, increased temperature can lead to higher solubility for many substances, although exceptions exist.
  • pH Levels: The acidity or basicity of a solution can impact the ionization of the compound and its subsequent solubility.

In summary, this compound is expected to demonstrate enhanced solubility in moderately polar solvents due to its significant number of functional groups. However, its complex structure suggests that solubility may not be straightforward and could be influenced by environmental conditions.

Interesting facts

Exciting Insights on 5-[(3S,5R,10R,13R,14S,17R)-3-[(2R,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

This compound, with its complex structure, belongs to a fascinating category of naturally occurring compounds known as steroidal derivatives. Not only is its chemical architecture elaborate, but it hints at a wealth of potential biological activities that scientists are just beginning to explore.

Key Facts

  • Chirality: The presence of several stereocenters in its structure contributes to its chirality, which can have profound implications in biological systems, affecting how it interacts with various receptors and enzymes.
  • Natural Product Potential: Many compounds in this class are derived from natural sources, making them subjects of interest for drug discovery, particularly in the fields of cancer and cardiovascular research.
  • Structure-Activity Relationship (SAR): The intricate arrangement of hydroxyl and methoxy groups may correlate with enhanced pharmacological properties, providing avenues for rational drug design.
  • Applications: Potential applications extend to nutraceuticals and pharmaceuticals, demonstrating the bridge between organic chemistry and therapeutic development.

Researchers often emphasize the significance of the compound’s antifungal and anti-inflammatory properties, cataloguing its effects on various biological pathways. It’s not uncommon for such compounds to represent the source of inspiration for synthesizing analogs with improved efficacy and reduced side effects.

Conclusion

In summary, 5-[(3S,5R,10R,13R,14S,17R)-3-[(2R,5R)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one is not just a cryptic string of symbols, but a gateway to understanding the intricate relationship between structure and functionality in bioactive molecules. 

Synonyms
Bovosidol A
BRN 0071268
468-13-3
Bufa-20,22-dienolide, 3-(6-deoxy-3-O-methyl-D-glucopyranosyl)oxy-14,19-dihydroxy-
4-18-00-02558 (beilstein handbook reference)
DTXSID30963659
3-[(6-Deoxy-3-O-methylhexopyranosyl)oxy]-14,19-dihydroxybufa-20,22-dienolide