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Lipid A

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Identification
Molecular formula
C176H306N2O60P
CAS number
143136-23-4
IUPAC name
[5-hydroxy-2-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate
State
State

At room temperature, Lipid A exists as a solid. It is hydrophobic, which allows it to integrate into the lipid bilayer of bacterial membranes, contributing to its structural stability.

Melting point (Celsius)
140.00
Melting point (Kelvin)
413.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
2394.16g/mol
Molar mass
2 394.1610g/mol
Density
1.0123g/cm3
Appearence

Lipid A is a lipid molecule that typically appears in a wax-like solid form. It is part of the lipopolysaccharide component of Gram-negative bacterial cell walls and is primarily responsible for the endotoxin activity of Gram-negative bacteria. In pure form, it can form crystalline structures.

Comment on solubility

Solubility of 5-hydroxy-2-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate (C176H306N2O60P)

The solubility of complex organic compounds like 5-hydroxy-2-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate can often be challenging to predict due to their intricate structures and functional groups. Here are some key aspects to consider when analyzing the solubility of this compound:

  • Polarity: The presence of multiple hydroxyl (-OH) and phosphonooxy groups can contribute to increased polarity, suggesting better solubility in polar solvents like water.
  • Hydrophobic Regions: The long tetradecanoyl chains imply hydrophobic characteristics, which could hinder solubility in polar environments and favor solubility in non-polar solvents.
  • pH Sensitivity: The phosphonooxy group may alter the compound's solubility depending on the pH of the solution, highlighting the importance of environmental factors on its dissolvability.
  • Concentration Effects: The solubility might vary with concentration; at lower concentrations, the compound might dissolve more readily than at saturation levels.

In summary, while the complex structure of this compound implies potential interactions that could enhance solubility in certain environments, the balance between hydrophilic and hydrophobic characteristics can lead to variability in solubility across different media. It's crucial to conduct empirical tests to provide definitive solubility data for practical applications.

Interesting facts

Interesting Facts About 5-hydroxy-2-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate

This complex compound, known for its intricate structure, plays a significant role in various biological processes and is of particular interest in the field of medicinal chemistry. Here are some compelling facts about this fascinating molecule:

  • Biological Significance: This compound is known to interact with cellular pathways, potentially influencing metabolic processes and cellular signaling.
  • Phosphorylation: The presence of phosphono groups suggests that this compound might be involved in phosphorylation reactions, which are critical for regulating protein functions.
  • Hydroxyl Groups: With multiple hydroxyl groups in its structure, this molecule can engage in hydrogen bonding, enhancing its solubility and interaction with biological membranes.
  • Amidation: The inclusion of tetradecanoyl groups indicates potential fatty acid interactions, which are essential for lipid metabolism and energy production in cells.
  • Structural Complexity: The tetracyclic configuration of the compound enhances its stereochemistry, allowing diverse conformations that may affect its reactivity and interaction with biomolecules.

Overall, the study of this compound could unlock new insights into drug design and the development of therapeutic agents. As one researcher aptly stated, "Understanding the intricacies of such molecules is key to advancing our knowledge in biochemistry and pharmacology."

With ongoing research into its properties and potential applications, this compound exemplifies the intersection of chemistry and biomedicine, showcasing the endless possibilities that complex molecules can offer.

Synonyms
SCHEMBL25930648