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Rapamycin

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Identification
Molecular formula
C51H79NO13
CAS number
53123-88-9
IUPAC name
5-[(2S,4R,6R,7R,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one
State
State

At room temperature, rapamycin is typically in the solid state. It is stable under normal conditions if kept dry and away from light.

Melting point (Celsius)
183.00
Melting point (Kelvin)
456.15
Boiling point (Celsius)
865.00
Boiling point (Kelvin)
1 138.15
General information
Molecular weight
914.17g/mol
Molar mass
914.1720g/mol
Density
1.1242g/cm3
Appearence

Rapamycin typically appears as a white to off-white crystalline powder. It is usually odorless and can sometimes appear slightly beige, depending on its purity. Due to its crystalline nature, it can have a fine granular texture.

Comment on solubility

Solubility of 5-[(2S,4R,6R,7R,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one

The solubility profile of this complex compound is intriguing and hinges on several factors, primarily dictated by its chemical structure. Understanding its solubility can be essential for practical applications, ranging from pharmaceutical uses to biochemical interactions.

Factors Influencing Solubility:

  • Molecular Weight: The large molecular structure can hinder solubility in common solvents.
  • Polarity: The presence of hydroxy groups increases polarity, potentially enhancing solubility in polar solvents like water.
  • Hydrophobic Regions: The pentacyclic structure introduces hydrophobic characteristics that might lead to limited solubility in aqueous solutions.

In general, compounds with a balance of hydrophobic and hydrophilic properties tend to exhibit more favorable solubility characteristics. As such, one might expect:

  • Better solubility in ethanol or methanol as compared to water.
  • Poor solubility in non-polar solvents, given its structural complexity.

Overall, the intricate structure features a delicate interplay between its hydrophilic and hydrophobic components, leading to a nuanced solubility behavior that could challenge conventional solvent compatibilities.

Interesting facts

Exploring 5-[(2S,4R,6R,7R,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one

This fascinating compound is a specialized natural product, showcasing the complexity of organic chemistry through its intricate structure. As a part of the larger family of chemical compounds known as pyranones, it features a unique arrangement of rings that contributes to its potential biological activities.

Key Characteristics

  • Stereochemistry: The compound is notable for its stereogenic centers, with a specific configuration indicated by the (2S,4R,6R,7R,11S,14S,16R) notation. This intricate stereochemistry plays a crucial role in determining the compound's reactivity and interactions with biological systems.
  • Pharmaceutical Significance: Compounds of this nature can serve as leads in drug design, potentially offering therapeutic benefits due to their unique molecular shapes and functional groups.
  • Natural Sources: Many pyranones are derived from plants and microorganisms, often involved in essential ecological roles, such as defense mechanisms against predators or pathogens.

The compound might prompt inquiries such as:
       "How does its structure influence its medicinal properties?"
       "Could it be synthesized for pharmaceutical applications?"

In summary, 5-[(2S,4R,6R,7R,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one serves as a testament to the beauty and complexity of organic molecules. Its study could potentially unveil new avenues in pharmacology and natural product chemistry, making it a compound of great interest to chemists and drug designers alike.

Synonyms
Bufogein
5-[(2S,4R,6R,7R,11S,14S,16R)-14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one
NCGC00181021-01
Bufogenin (JAN/INN)
SCHEMBL1652389
NCGC00181021-02
NS00120227
C17058
D01378
Q27114274
(3beta,5beta,15beta)-14,15-Epoxy-3-hydroxybufa-20,22-dienolide