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Erythromycin

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Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
2-[[(6aR,11aS)-9-[(1S)-1-[(2S)-3-hydroxy-5-methyl-2-piperidyl]ethyl]-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-3-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
State
State

At room temperature, erythromycin is in a solid state, typically available as a crystalline powder or in tablet form. It is stable under recommended storage conditions, which include protection from moisture and heat.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
745.40
Boiling point (Kelvin)
1 018.55
General information
Molecular weight
733.94g/mol
Molar mass
733.9410g/mol
Density
1.1508g/cm3
Appearence

Erythromycin appears as a white to off-white powder. It is slightly soluble in water and freely soluble in alcohol, chloroform, and ether. It should be stored in a tightly sealed container protected from light and moisture.

Comment on solubility

Solubility of 2-[[(6aR,11aS)-9-[(1S)-1-[(2S)-3-hydroxy-5-methyl-2-piperidyl]ethyl]-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-3-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

The solubility of this complex compound is primarily determined by its unique structure and functional groups. Here are some key factors influencing its solubility:

  • Hydroxyl Groups: The presence of multiple hydroxyl groups (-OH) suggests that the compound may exhibit good solubility in polar solvents like water due to hydrogen bonding.
  • Hydrophobic Regions: The large hydrophobic regions in the benzo[a]fluorene framework could decrease solubility in polar solvents, potentially causing a balance of properties that may limit its overall solubility.
  • Amine Functionality: The molecule contains piperidine structure which can contribute to solubility behaviors depending upon the conditions and resultant ionization.

In summary, while the multiple hydroxyl groups may enhance the water solubility of this compound, the significant presence of hydrophobic sections is likely to hinder it, making the solubility behavior quite complex. It highlights a beautiful interplay of chemical functionalities, suggesting that solubility may vary widely based on environmental conditions.

Interesting facts

Interesting Facts about 2-[[(6aR,11aS)-9-[(1S)-1-[(2S)-3-hydroxy-5-methyl-2-piperidyl]ethyl]-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-3-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

This compound is a fascinating example of complexity in organic chemistry, showcasing the intricate interplay of stereochemistry and functional group orientation. It belongs to a class of compounds that exhibit a significant degree of chirality, which is pivotal in determining the behavior and reactivity of molecules in biological systems. Here are some engaging points about this compound:

  • Stereochemistry: This molecule has multiple stereocenters, which means it can exist in various chiral forms. The specified configurations (6aR, 11aS) highlight the importance of stereochemistry in impacting the compound's biological properties.
  • Biological Activity: While the specific biological functions of this compound may vary, compounds with similar structural characteristics have been studied for their potential roles in medicinal chemistry, particularly in neuropharmacology.
  • Functional Groups: The presence of hydroxymethyl and piperidine moieties could hint at potential interactions with biological macromolecules, hence influencing various biochemical pathways.
  • Complexity in Synthesis: The synthesis of such a structurally complex molecule can pose significant challenges, often requiring multi-step synthetic strategies and careful control over reaction conditions to ensure the desired stereochemistry is achieved.
  • Applications in Drug Development: Given its structural features, this compound could be a candidate for drug development, especially targeting specific receptors or enzymes due to its unique geometric and electronic properties.

As with many compounds in the realm of organic chemistry, further research and investigation are essential to unravel the full potential and applications of this intriguing molecule. In the words of renowned chemist Robert H. Grubbs, "The beauty of chemistry lies in the complexity and diversity of molecules, each with their own story to tell." This compound is no exception!