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Erythromycin

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Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
(2R,3R)-2,3-dihydroxybutanedioic acid;2-[(4R,5S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
State
State

At room temperature, erythromycin is typically in a solid state as a crystalline powder. It is stable under normal conditions but should be kept in a tightly closed container, away from light and moisture, to avoid degradation.

Melting point (Celsius)
135.50
Melting point (Kelvin)
408.50
Boiling point (Celsius)
194.00
Boiling point (Kelvin)
467.00
General information
Molecular weight
733.94g/mol
Molar mass
733.9380g/mol
Density
1.2440g/cm3
Appearence

Erythromycin appears as a white or slightly yellow crystalline powder. It is practically odorless and has a bitter taste. In powder form, it can clump together easily upon exposure to air due to its hygroscopic nature.

Comment on solubility

Solubility of (2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(4R,5S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde

The solubility of complex organic compounds such as (2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(4R,5S,7R,9R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde is influenced by several structural factors. The presence of multiple hydroxyl (-OH) groups typically suggests a favorable solubility in polar solvents such as water. However, the overall structure is quite intricate, which may lead to unique solubility characteristics.

  • Polar Functional Groups: The dihydroxy and other hydroxyl groups promote strong hydrogen bonding, enhancing solubility in polar media.
  • Hydrophobic Regions: Alkyl chains and cyclic structures may introduce hydrophobicity, potentially limiting solubility in aqueous environments.
  • Conformational Variability: The compound's necessary conformations may influence how well it interacts with solvents, affecting solubility.

In conclusion, while the presence of polar functional groups enhances water solubility, the complex structure of this compound may result in variable solubility depending on the solvent used. As noted, “the structure influences the way molecules interact”—therefore, understanding the balance between hydrophilic and hydrophobic sections is crucial in predicting solubility in different solvents.

Interesting facts

Interesting Facts about (2R,3R)-2,3-Dihydroxybutanedioic Acid and Its Complex Derivative

(2R,3R)-2,3-dihydroxybutanedioic acid is an intriguing compound that falls under the category of dicarboxylic acids, showcasing unique properties due to its multiple hydroxyl (-OH) groups. This compound is also known as tartaric acid in its more simplified form. Here are some fascinating aspects of this compound and its derivative:

  • Natural Occurrence: Tartaric acid is predominantly found in grapes and is a vital component in the winemaking process, contributing to a wine’s flavor and stability.
  • Pharmaceutical Applications: Its derivatives are often employed in the pharmaceutical industry due to their ability to enhance the solubility and stability of various drugs.
  • Chirality: The (2R,3R) configuration indicates that this compound has chiral centers, leading to different stereoisomers. Stereochemistry plays a crucial role in drug design and biological activity.

Exploration of the Complex Derivative

The complex structure derived from (2R,3R)-2,3-dihydroxybutanedioic acid features a multitude of functional groups and stereocenters, making it a subject of interest in synthetic organic chemistry. Consider the following:

  • Structural Complexity: The intricate arrangement of carbon, oxygen, and nitrogen within this derivative provides a rich avenue for research into its potential applications.
  • Biological Importance: Research is ongoing to understand how such complex molecules interact with biological systems, potentially leading to new therapeutic agents.
  • Enzymatic Reactions: The multiple hydroxyl groups can act as substrates for various enzymatic reactions, opening pathways for biological and chemical synthesis.

In summary, the exploration of (2R,3R)-2,3-dihydroxybutanedioic acid and its more complex derivatives reveals a fascinating intersection of natural products, pharmaceutical applications, and chemical synthesis. The impact of chirality and structural complexity in these compounds cannot be overstated, as they offer potential for innovation in various fields, including medicinal chemistry and biochemistry.