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Atorvastatin

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Identification
Molecular formula
C33H35FN2O5
CAS number
110862-48-1
IUPAC name
4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
State
State

Atorvastatin is typically found in a solid state at room temperature. It is most stable in its crystalline form and used as a pharmaceutical substance due to its physical and chemical properties.

Melting point (Celsius)
159.00
Melting point (Kelvin)
432.00
Boiling point (Celsius)
458.00
Boiling point (Kelvin)
731.00
General information
Molecular weight
1209.42g/mol
Molar mass
1 209.4200g/mol
Density
1.0660g/cm3
Appearence

Atorvastatin typically appears as a white to off-white crystalline powder. It is known for its characteristic odorless property and is a compound that is often utilized in its salt form.

Comment on solubility

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

This complex compound presents intriguing solubility characteristics, primarily due to its structural components. The presence of hydroxyl groups, indicated in its name, generally enhances solubility in polar solvents, particularly water. However, the extensive hydrocarbon chain contributes to hydrophobic interactions, potentially limiting its solubility in aqueous environments. Here's a breakdown of the solubility factors:

  • Hydroxyl Groups: The presence of two hydroxyl groups (-OH) suggests that the compound can form hydrogen bonds, which often leads to increased solubility in water.
  • Hydrophobic Chain: The long carbon chain introduces significant hydrophobic character, which may challenge solubility in polar solvents, particularly water.
  • Solvent Selection: The compound may exhibit better solubility in organic solvents like ethanol or methanol compared to aqueous solutions due to its lipophilic portions.
  • pH Dependence: The acidity of the carboxylic acid functional group can influence solubility, as it may dissociate in basic conditions, potentially increasing solubility through ionic interactions.

In conclusion, while the presence of polar functional groups can enhance solubility, the overall structure leans towards a complex hydrophobic profile. Hence, one can expect variable solubility behavior depending on the solvent conditions employed, making it essential to consider the target application when predicting solubility in this case.

Interesting facts

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

This compound is a fascinating example of a complex steroid-like structure. Here are some captivating details about this compound:

  • Structural Complexity: The intricate configuration involves multiple chiral centers, indicating a high level of stereochemical specificity which is significant in biological interactions.
  • Biological Relevance: This compound might belong to a class of molecules with potential pharmacological properties, particularly in the realm of steroids, making it an interesting subject for research in medicinal chemistry.
  • Natural Occurrence: Similar compounds are often found in nature, potentially serving as natural hormones or signaling molecules. This hints at the evolutionary significance of such structures in biological organisms.
  • Potential Usage: The functionality of the hydroxyl (-OH) groups in the structure may contribute to the compound's reactivity and can be exploited for various biological applications, including drug development.
  • Synthesis Challenges: The synthesis of compounds with such complexity often presents significant challenges, requiring advanced synthetic techniques and often multi-step processes to achieve the desired configuration.

This compound exemplifies the beauty of organic chemistry, revealing how intricate molecular architectures can lead to significant biological functions and therapeutic potentials. Further exploration and study of this compound could yield new discoveries in both chemistry and pharmacology.

Synonyms
4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
SCHEMBL11967213
CHEBI:124935
CCG-208090
BRD-A08027849-236-01-7
Q27215246