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Erythromycin A

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Identification
Molecular formula
C37H67NO13·HCl
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;hydrochloride
State
State

Erythromycin A hydrochloride is typically a solid at room temperature.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.00
Boiling point (Celsius)
470.00
Boiling point (Kelvin)
743.00
General information
Molecular weight
833.98g/mol
Molar mass
833.9840g/mol
Density
1.2500g/cm3
Appearence

Erythromycin A hydrochloride appears as a white to off-white crystalline powder.

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; hydrochloride

The solubility of this compound is quite complex due to its intricate molecular structure. Generally, the solubility can be influenced by several factors, such as:

  • Polarity: The presence of functional groups, such as hydroxyl (−OH) and acetoxy (−OCOCH3) moieties, can increase solubility in polar solvents.
  • Ionic Nature: Being in the form of hydrochloride can enhance solubility in water, as ionic compounds tend to dissolve better in polar solvents.
  • Hydrogen Bonding: The multiple −OH groups may facilitate strong hydrogen bonding interactions with water molecules.
  • Hydrophobic Regions: Despite some polar characteristics, the presence of hydrophobic regions from hydrocarbon chains may limit its solubility in pure water.

In summary, while the compound can exhibit reasonable solubility in polar solvents, it may face challenges in excessively hydrophobic environments. Therefore, it is important to carefully consider the solvent choice when working with this compound to optimize its solubility characteristics.

Interesting facts

Interesting Facts about the Compound

This complex compound is a member of the class of molecules known as natural products, specifically categorized among alkaloids and terpenoids due to its intricate structure and biological activities.

Key Highlights:

  • Natural Product Origins: Many compounds like this one are derived from plants and possess significant pharmacological properties, contributing to their medicinal use.
  • Chirality: The multiple chiral centers indicated in the structure result in a variety of stereoisomers. This chirality is crucial as different isomers can exhibit vastly different biological activities.
  • Biological Activities: Compounds with similar structures often demonstrate a range of activities such as anti-inflammatory, anti-cancer, and antimicrobial effects, making them a focus of ongoing research in drug development.
  • Complex Synthesis: The synthesis of such compounds typically involves multiple reaction steps and may require advanced techniques such as asymmetric synthesis to yield a specific isomer.
  • Research Potential: Given its structural complexity, studies on this compound may unlock new pathways in medicinal chemistry and could potentially lead to the discovery of new therapeutic agents.

As a chemistry student or scientist delving into organic synthesis, understanding the nuances of such complex compounds is essential. Each chiral center contributes to the overall properties and functions of the molecule, and further studies could reveal even more about its impact and applications in various fields of science.

"The beauty of organic chemistry lies in the complexity of its molecules and the simplicity in their synthesis."