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Erythromycin

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Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2,4-dimethyl-tetrahydropyran-3-yl] 3-methylbutanoate
State
State

At room temperature, erythromycin is typically found in a solid state. It is often used in its base or salt form for pharmaceutical applications.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.15
General information
Molecular weight
733.94g/mol
Molar mass
733.9370g/mol
Density
1.2400g/cm3
Appearence

Erythromycin is a white to off-white crystalline powder. It may appear in various forms including small crystals or a fine powder. It is often odorless or may have a faint characteristic smell.

Comment on solubility

Solubility of [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[[4R,5S,6S,7R,9R,16R)-4-acetoxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2,4-dimethyl-tetrahydropyran-3-yl] 3-methylbutanoate

The solubility of this complex organic compound is influenced by various factors, including its structural features and functional groups. The presence of multiple hydroxy (-OH) groups and ether linkages suggests potential solubility in polar solvents, particularly due to hydrogen bonding capabilities.

Key points regarding its solubility include:

  • Polar solvents: It is likely soluble in water or alcohols due to its numerous polar functional groups.
  • Solvent interactions: The structural configuration might facilitate interactions with both polar and non-polar solvents, suggesting variable solubility behavior.
  • Concentration levels: Solubility might depend on concentration, temperature, and pH, making it necessary to conduct empirical solubility tests for accurate determination.
  • Derived forms: In certain derivatives, such as salts, solubility may be enhanced compared to the parent compound.

In summary, while the intricate structure hints at potential solubility, actual behavior will need to be determined experimentally, supporting the notion that "solubility is as much an art as it is a science." Understanding the balance of polar and non-polar interactions is crucial for applications in pharmaceuticals and chemistry.

Interesting facts

Interesting Facts about the Compound: A Unique Natural Product

This compound, known for its complex structure and intricate stereochemistry, represents a fascinating example of a natural product with significant biological activity. It showcases a remarkable architecture that includes several stereocenters, demonstrating the exquisite precision required in organic synthesis.

Biological Significance

Natural products often serve as inspiration for drug design, and this compound is no exception. Here are a few key points regarding its biological relevance:

  • Potential Pharmacological Activity: Compounds similar to this structure are often investigated for their anti-inflammatory and anticancer properties.
  • Enzyme Inhibition: It may exhibit activity against specific enzymes, contributing to its potential as a therapeutic agent.
  • Structural Diversity: The unique arrangement of functional groups enhances its interaction with biological targets.

Challenges in Synthesis

The synthesis of such a compound poses considerable challenges due to its multi-step process and the need for stereoelectronic control. Some notable aspects include:

  • Regioselectivity: Achieving selective functionalization at distinct sites is crucial to maintain the integrity of the structure.
  • Stereochemical Integrity: Maintaining the correct stereochemical configuration at each chiral center is pivotal for the compound's activity.
  • Protecting Groups: A variety of protecting groups may be employed to selectively activate certain functional groups at various steps in the synthesis.

Future Perspectives

Research on this compound and similar analogs holds great promise. Chemists continue to explore:

  • Green Chemistry: Developing more sustainable and efficient synthetic routes that minimize waste and environmental impact.
  • Derivatives Development: Modifying the structure to optimize biological activity and reduce toxicity.
  • Mechanism of Action Studies: Understanding how this compound interacts with biological systems through advanced imaging and molecular modeling techniques.

The exploration of this compound not only highlights the beauty of organic chemistry but also underscores the endless possibilities within natural product research and medicinal chemistry.