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Simvastatin

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Identification
Molecular formula
C25H38O5
CAS number
79902-63-9
IUPAC name
5-[(3S,10R,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
State
State

At room temperature, simvastatin is in a solid state, appearing as a crystalline powder.

Melting point (Celsius)
139.00
Melting point (Kelvin)
412.15
Boiling point (Celsius)
381.80
Boiling point (Kelvin)
654.95
General information
Molecular weight
418.57g/mol
Molar mass
418.5740g/mol
Density
1.2000g/cm3
Appearence

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

Comment on solubility

Solubility of 5-[(3S,10R,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

The solubility of the compound 5-[(3S,10R,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-3-[(2S,5S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one is of particular interest due to its complex structure. Solubility is influenced by several factors, which may include:

  • Polarity: The presence of multiple hydroxy groups suggests significant polarity, enhancing solubility in polar solvents such as water.
  • Hydrogen bonding: The ability to form hydrogen bonds due to hydroxyl (-OH) groups can improve interaction with solvent molecules.
  • Molecular size: The large and complex molecular structure can create steric hindrance, potentially impeding solubility in nonpolar solvents.
  • Functional groups: The presence of pyran and cyclopenta features may further dictate solubility characteristics by influencing conformational dynamics in different solvents.

Overall, one might say, "Solubility is the key that opens the door to biological activity, formulation, and application.” The solubility of this compound is likely favorable in aqueous conditions due to its hydrophilic functional groups, while its solubility in organic solvents may require specific conditions or cosolvents to achieve desired concentrations.

Interesting facts

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

This compound, with its complex structure, belongs to the class of natural products that showcases the incredible diversity of organic chemistry. Here are some fascinating aspects of this unique compound:

  • Natural Origins: Many compounds similar to this one are derived from plant sources and possess biological activities that can benefit human health.
  • Steroidal Framework: The compound features a steroid-like structure, which is significant in medicinal chemistry for the development of hormones and anti-inflammatory drugs.
  • Hydroxyl Groups: The presence of multiple hydroxy (-OH) groups in its structure often contributes to its reactivity, solubility, and interaction with biological systems.
  • Chiral Centers: This compound contains numerous stereocenters, emphasizing the importance of stereochemistry in determining the compound's biological activity and properties.

One of the exciting aspects of this compound is its potential applications in pharmacology. Due to its intricate structure, it may exhibit unique biological activities. As Dr. Jane Goodwin once said, “The complexity of nature’s molecules is a reminder of how much we have yet to learn.” This sentiment rings true in the realm of chemical compounds, particularly for those with challenging compositions like this one.

In conclusion, this compound serves as a remarkable example of the intersection between complex organic structures and their potential medicinal applications. The ongoing exploration of such compounds not only enhances our understanding of chemistry but also paves the way for innovative therapeutic strategies.

Synonyms
DTXSID30943673
3-[(6-Deoxyhexopyranosyl)oxy]-12,14-dihydroxybufa-4,20,22-trienolide