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Lincomycin

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Identification
Molecular formula
C18H34N2O6S
CAS number
154-21-2
IUPAC name
(2S,4R)-N-[(1S)-2-hydroxy-1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide
State
State

At room temperature, Lincomycin is a solid. It is stable under normal temperatures and pressures.

Melting point (Celsius)
158.00
Melting point (Kelvin)
431.00
Boiling point (Celsius)
372.15
Boiling point (Kelvin)
645.30
General information
Molecular weight
406.55g/mol
Molar mass
406.5460g/mol
Density
1.3000g/cm3
Appearence

Lincomycin is typically seen as a white to off-white powder. It is crystalline in nature.

Comment on solubility

Solubility of (2S,4R)-N-[(1S)-2-hydroxy-1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide

The solubility of this complex organic compound can be quite intriguing, primarily due to its structural characteristics. Here are several key points regarding its solubility:

  • Polarity: The presence of multiple hydroxyl groups (–OH) typically enhances solubility in polar solvents, especially water. This is bolstered by their ability to form hydrogen bonds.
  • Hydrophobic Regions: The alkyl groups (1-methyl, 4-propyl) introduce hydrophobic characteristics, which can limit solubility in water.
  • Solvent Interaction: The solubility may significantly vary in different solvents. For example:
    • Highly polar solvents like methanol and ethanol could increase solubility due to favorable interactions.
    • Aprotic solvents may poorly solubilize the compound due to the hydrophobic parts dominating.
  • pH Sensitivity: Depending on the pH of the solution, the ionization of the carboxamide group can affect solubility. A more basic environment may enhance solubility.

In conclusion, the solubility of this compound is influenced by a delicate balance between its hydrophilic functionalities and hydrophobic regions. As one can observe, predicting the solubility is multifaceted and requires consideration of multiple factors combined with experimental data.

Interesting facts

Interesting Facts about (2S,4R)-N-[(1S)-2-hydroxy-1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide

This complex compound boasts a fascinating structure that encompasses both chiral centers and a variety of functional groups, which makes it a subject of considerable interest in the fields of organic and medicinal chemistry. Here are some noteworthy aspects:

  • Stereochemistry: The compound contains multiple stereogenic centers. Its specific stereochemistry is crucial for determining its biological activity, as even subtle changes in configuration can lead to drastically different effects in biological systems.
  • Functional Diversity: This molecule features a blend of functional groups, notably a hydroxyl group and a carboxamide, which can play essential roles in its reactivity and interaction with biological targets.
  • Natural Product Derivative: The presence of the tetrahydropyran ring suggests a potential lineage to natural products, which often serve as the foundation for the development of pharmaceuticals.
  • Biological Relevance: Compounds like this one are frequently studied for their potential therapeutic applications, particularly as they may mimic or inhibit biological processes.
  • Sulfanyl Functionality: The inclusion of a methylsulfanyl group is particularly interesting as it can affect the compound's pharmacokinetics and pharmacodynamics.

As researchers delve deeper into the world of compounds like (2S,4R)-N-[(1S)-2-hydroxy-1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide, they uncover the intricate relationships between structure and function that drive the development of new therapeutic agents. The challenge lies in synthesizing and characterizing such intricate molecules, paving the way for discoveries that could revolutionize medicine.

Synonyms
Lincomycin A
(2S,4R)-N-[(1S)-2-hydroxy-1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
12768-69-3
DTXSID50925936
OJMMVQQUTAEWLP-ZUWRKQLMSA-N
Methyl 6,8-dideoxy-6-{[hydroxy(1-methyl-4-propylpyrrolidin-2-yl)methylidene]amino}-1-thiooctopyranoside