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Erythromycin A

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

At room temperature, Erythromycin A is typically a crystalline powder and is insoluble in water. It is often prepared in formulations that increase its solubility in bodily fluids for therapeutic use.

Melting point (Celsius)
135.00
Melting point (Kelvin)
408.15
Boiling point (Celsius)
148.00
Boiling point (Kelvin)
421.15
General information
Molecular weight
733.94g/mol
Molar mass
733.9370g/mol
Density
1.2481g/cm3
Appearence

In pure form, Erythromycin A appears as white or slightly yellowish crystalline powder. It is typically available as its stearate or ethylsuccinate ester for oral administration, which also have a slightly yellow appearance.

Comment on solubility

Solubility of 6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one (C37H67NO13)

The solubility of a compound like 6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one is influenced by several factors, including its complex structure and functional groups. Here are some key points regarding its solubility:

  • Polarity: The presence of multiple hydroxyl (-OH) and ether (-O-) groups typically enhances solubility in polar solvents such as water.
  • Hydrophobic regions: The significant hydrophobic portions of the molecule may limit solubility in aqueous environments, potentially leading to lower solubility overall.
  • Solvent interaction: It is likely to exhibit varying solubility in different organic solvents; for example, it may be more soluble in ethanol or methanol compared to chloroform.
  • Temperature: The solubility can also be temperature-dependent, often increasing with elevated temperatures.
  • Concentration: In saturated solutions, interactions between similar molecules can lead to unique solubility equilibria.

Overall, while the specific solubility values would require empirical measurements, it can be said that the interplay between its polar functional groups and hydrophobic components dictates its solubility behavior in various solvents. As with many complex pharmaceutical compounds, characterization and experimental validation are key for determining solubility in practical applications.

Interesting facts

Interesting Facts about 6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

This compound, a complex organic molecule, is a fascinating example of the intricate world of chemical synthesis. Here are some intriguing facts about it:

  • Structural Complexity: The compound features multiple functional groups, including hydroxyl, methoxy, and dimethylamino groups, which contribute to its diverse chemical reactivities and biological activities. The arrangement of these functional groups allows for various interactions with biological molecules.
  • Biological Significance: Due to its structural makeup, this compound may possess pharmacological properties and could be explored for potential therapeutic applications. Many compounds with similar structures are studied for their effects on cellular processes.
  • Synthesis Challenges: Creating such a large and complex molecule can be a daunting task for chemists. The synthetic pathways often require numerous steps, high precision, and specific conditions to ensure the product’s purity and yield.
  • Research Potential: Molecules like this one play a crucial role in medicinal chemistry, providing valuable insights into drug design and development. The study of such compounds can lead to innovations in treatments for various diseases.
  • Learning Opportunities: For chemistry students, analyzing the structure and synthesis processes of this compound can enhance understanding of organic chemistry concepts, such as stereochemistry, functionalization, and reactivity patterns.

In conclusion, the compound represents more than just a collection of atoms; it is a testament to the beauty and complexity of organic chemistry, showcasing how scientists can manipulate structures to explore new frontiers in science.

Synonyms
roxithromycin
80214-83-1
Erythromycin 9-(-O-[2-methoxyethoxy]methyloxime)
DTXSID50861022
134931-00-3
BCP13066
6-{[4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy]-10-{[(2-methoxyethoxy)methoxy]imino}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
6-{[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy]-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one