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Erythromycin A

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Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
(4R,8S,12R,19S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13,19-pentamethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
State
State

At room temperature, Erythromycin A is typically in a solid crystalline form. It is stable under normal conditions and can be kept in a dry place to maintain its efficacy as a macrolide antibiotic.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
838.30
Boiling point (Kelvin)
1 111.45
General information
Molecular weight
733.94g/mol
Molar mass
733.9370g/mol
Density
1.1830g/cm3
Appearence

Erythromycin A appears as a white to off-white crystalline powder. It is commonly provided in its crystalline form, and as an antibiotic, it is also formulated into tablets or capsules for medical use. Its appearance can vary slightly depending on the formulation and presence of excipients in pharmaceutical preparations.

Comment on solubility

Solubility of (4R,8S,12R,19S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13,19-pentamethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

The solubility of the compound (4R,8S,12R,19S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13,19-pentamethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one is a complex subject due to its intricate structure and multiple functional groups. Several factors influence its solubility:

  • Polarity: The presence of hydroxyl (-OH) and carbonyl (C=O) groups typically enhances polar interactions, potentially improving solubility in polar solvents like water.
  • Alkyl Substituents: The pentamethyl groups may increase hydrophobic character, which can limit solubility in aqueous solutions.
  • Solvent Interaction: Such a compound may exhibit variable solubility in different solvents; for instance:
    • Good solubility in organic solvents (e.g., ethanol, acetone)
    • Poor solubility in water or highly polar environments

Researchers often find that the harmonic balance between hydrophilic and hydrophobic characteristics dictates the solubility profile of such large and complex molecules. As a rule of thumb, "like dissolves like," meaning that a compound's solubility can be predicted based on its structural relatives and the solvent's polarity. Thus, understanding the solubility behavior of this compound is crucial for applications in pharmaceuticals, materials science, and chemical synthesis.

Interesting facts

Interesting Facts about (4R,8S,12R,19S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13,19-pentamethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

This intricate compound represents a fascinating example of molecular architecture with significant implications in pharmaceutical science. Here are some noteworthy aspects:

  • Complex Structure: The compound showcases a unique pentacyclic structure that contributes to its distinctive chemical properties. The multiple rings provide a robust framework, making it an interesting subject for structural analysis.
  • Fluorine's Influence: The presence of a fluorine atom in this compound can significantly enhance its biological activity and metabolic stability. Fluorine substitutions are well-known to modify the pharmacokinetics of compounds, often resulting in enhanced potency.
  • Hydroxy Groups: Multiple hydroxy functional groups can impact the solubility and reactivity of the compound, which are critical factors in drug design. These functional groups also enable potential interactions with biological targets, making it relevant for medicinal chemistry.
  • Potential Applications: Given its structure and functional groups, this compound may hold promise in therapeutic areas such as anti-cancer agents or enzyme inhibition, bolstering the importance of studying such complex molecules.
  • Chirality Matters: The specific stereochemistry (4R, 8S, 12R, 19S) underscores the importance of chirality in pharmacology. Chirality can lead to different biological activities, with one enantiomer potentially being more effective or safer than the other.

As researchers and students dive deeper into such compounds, it's crucial to understand how slight modifications can lead to vastly different outcomes in both chemical behavior and biological activity. As one prominent chemist once said, "The diversity of organic chemistry is unmatched, and each compound tells its own story."

In conclusion, (4R,8S,12R,19S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13,19-pentamethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one is more than just a formula; it's a window into the potential of chemical innovation and therapeutic advancements.