Skip to main content

Erythromycin

ADVERTISEMENT
Identification
Molecular formula
C37H67NO13
CAS number
114-07-8
IUPAC name
(3R,4S,6R,7R,9R,11R,12S,13R,14R)-6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
State
State

At room temperature, erythromycin is typically in a solid state.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.20
Boiling point (Celsius)
693.70
Boiling point (Kelvin)
966.90
General information
Molecular weight
733.93g/mol
Molar mass
733.9360g/mol
Density
1.2400g/cm3
Appearence

Erythromycin is a white or slightly yellow, crystalline powder. It may have a faint odor and is often used in the form of esters or salts, which can affect its appearance slightly. The powder is practically insoluble in water but is soluble in ethanol and chloroform.

Comment on solubility

Solubility of the Compound

The solubility of the compound (3R,4S,6R,7R,9R,11R,12S,13R,14R)-6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione can be quite complex due to its intricate structure. Several factors influence its solubility:

  • Molecular Structure: The presence of multiple functional groups such as hydroxy and ether linkages can enhance solubility in polar solvents.
  • Hydrophobic vs Hydrophilic: Despite the hydrophilic groups, the bulky hydrocarbon chains may hinder complete solubility in water, leading to variances in solubility depending on the medium.
  • Steric Hindrance: The spatial arrangement of the molecular framework may create challenges for solvent interactions.
  • pH Sensitivity: The solubility might be affected by the pH of the solution, particularly due to the presence of amine groups.

In practice, this compound is expected to exhibit better solubility in organic solvents like ethanol or DMSO, while its solubility in water may be limited. For example, compounds with similar structures often show:

  1. A tendency to precipitate in aqueous environments.
  2. Enhanced stability and solubility in slightly alkaline solutions due to protonation effects.

As is common with complex organic molecules, studying solubility often requires empirical testing to determine precise solubility limits. Consequently, understanding these solubility mechanisms is crucial for applications in fields such as pharmacology and materials science.

Interesting facts

Interesting Facts about (3R,4S,6R,7R,9R,11R,12S,13R,14R)-6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

This complex organic compound showcases the fascinating world of stereochemistry and functional diversity. Here are some noteworthy aspects:

  • Stereochemistry: This compound exhibits multiple stereocenters, leading to distinct spatial arrangements. The specific R/S configurations indicate the potential for unique interactions in biochemical pathways.
  • Biological Activity: Compounds like this often serve vital functions in biological systems, possibly as intermediates in metabolic processes or as active pharmaceutical ingredients. They could play important roles in the discovery and development of new drugs.
  • Structural Complexity: The intricate structure, featuring a combination of hydroxyl groups and tetrahydropyran moieties, highlights the versatility of organic molecules. This complexity can lead to a variety of chemical behaviors and functionalities.
  • Potential Applications: Compounds with similar frameworks are often considered in fields such as:
    • Medicinal Chemistry
    • Natural Products Research
    • Agricultural Chemistry
  • Quote from a Chemist: "The beauty of chemistry lies in its ability to create molecules that can mimic nature’s precision and complexity." This is evident in the design and synthesis of such compounds.

Overall, the study of this compound not only enhances our understanding of chemical principles but also broadens the scope for innovation in various scientific disciplines.

Synonyms
b erythromycin
Erythromycin B, Berythromycin, 12-Deoxyerythromycin
(3R,4S,6R,7R,9R,11R,12S,13R,14R)-6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
6-(4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12-dihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione