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Tetracycline

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Identification
Molecular formula
C22H24N2O8
CAS number
60-54-8
IUPAC name
(1R,3S,5R,8R,10R,11S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one
State
State

At room temperature, tetracycline is a solid.

Melting point (Celsius)
213.00
Melting point (Kelvin)
486.00
Boiling point (Celsius)
780.00
Boiling point (Kelvin)
1 053.00
General information
Molecular weight
444.44g/mol
Molar mass
444.4350g/mol
Density
1.5000g/cm3
Appearence

Tetracycline is typically a light yellow crystalline powder. It may appear slightly hygroscopic, absorbing moisture from the air.

Comment on solubility

Solubility of (1R,3S,5R,8R,10R,11S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one

The solubility of this complex organic compound is influenced by several key structural features, making it quite intriguing:

  • Hydroxyl Groups: The presence of three hydroxyl (–OH) groups indicates potential for hydrogen bonding with water molecules, which may enhance its solubility in polar solvents.
  • Methylamino Substituents: The bis(methylamino) groups can also facilitate interactions with water, particularly in ionized form, suggesting it might exhibit greater solubility under acidic or basic conditions.
  • Cyclic Structure: The intricate tricyclic configuration can impact its overall solubility, as steric factors may hinder or facilitate below mentioned interactions.

However, predicting solubility is often a balance of these factors:

  • If the compound forms numerous hydrogen bonding interactions, it is likely to be relatively soluble in water.
  • Conversely, any significant hydrophobic character from the rest of the hydrocarbon framework can limit solubility.

In practice, solubility should be empirically tested, as theoretical predictions may not always align with experimental findings due to the complexity of molecular interactions in various solvents. Ultimately, this compound's unique architecture leads to a rich tapestry of solubility behavior that merits detailed investigation.

Interesting facts

Interesting Facts about (1R,3S,5R,8R,10R,11S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one

This fascinating compound is an example of a complex organic molecule that showcases the intricacies of chemical synthesis and the versatility of carbon-based compounds. Here are some remarkable aspects of this compound:

  • Stereochemistry: The compound has multiple stereocenters, indicated by its detailed stereochemical nomenclature. This means it exists in different spatial arrangements, potentially impacting its reactivity and biological interactions.
  • Hydroxyl Groups: The presence of three hydroxyl groups (–OH) contributes significantly to the molecule's chemical properties, such as solubility and intermolecular interactions. Hydroxyl groups often enhance polarity and can engage in hydrogen bonding, making them critical for biological functions.
  • Tricyclic Structure: As a tricyclic compound, this molecule exhibits unique structural characteristics that can affect its stability and reactivity. Tricyclic compounds are prominent in various fields such as pharmaceuticals and organic chemistry for their potential pharmaceutical applications.
  • Biological Relevance: Compounds with similar structures have been studied extensively due to their potential biological activity. They may serve as key intermediates or active components in therapeutics, showcasing the importance of structural diversity in medicinal chemistry.
  • Synthesis Challenges: The complexity of its synthesis reflects the challenges encountered in creating multi-functional molecules. This can involve multiple steps of functionalization, protecting group strategies, and resolving stereochemistry, making it a significant topic in organic synthesis courses.

In conclusion, this compound not only represents the pinnacle of synthetic organic chemistry but also symbolizes the relationship between structure and function in biological systems. As you delve deeper into the study of such complex molecules, remember the intricate balance between their physical, chemical, and biological properties!