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Lipid A

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Identification
Molecular formula
C96H182NO28P2
CAS number
202938-13-0
IUPAC name
[3-hydroxy-2-[[6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-5-phosphonooxy-tetrahydropyran-2-yl]oxymethyl]-5-(3-hydroxytetradecanoylamino)-6-phosphonooxy-tetrahydropyran-4-yl] 3-hydroxytetradecanoate
State
State

Lipid A is usually found in a solid state at room temperature. Its amphiphilic nature means that it can integrate into biological membranes or micelles, which is a key component of the lipopolysaccharides found in the outer membrane of Gram-negative bacteria.

Melting point (Celsius)
240.00
Melting point (Kelvin)
513.15
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.15
General information
Molecular weight
1796.11g/mol
Molar mass
1 796.1050g/mol
Density
1.3500g/cm3
Appearence

Lipid A is typically a colorless to pale yellow solid. It may appear as a waxy or greasy substance consisting of acyl chains. The compound is amphipathic, showing both hydrophobic and hydrophilic regions, which is typical for lipid molecules.

Comment on solubility

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

The solubility of the compound with the formula C96H182NO28P2 reflects the complexities associated with its extensive structure that includes multiple hydroxy and phosphonic acid groups. Here are some key aspects to consider:

  • Hydrophilic Regions: The presence of numerous hydroxyl (-OH) groups contributes to its potential *hydrophilicity*, making it more soluble in polar solvents such as water.
  • Hydrophobic Characteristics: Conversely, the long hydrophobic tetradecanoyl chains may reduce solubility in water but enhance solubility in organic solvents.
  • Phosphate Groups: The phosphonic acid components add further complexity. These groups generally increase aqueous solubility, especially in ionized form.

It is crucial to note that the overall solubility of this compound will depend on:

  1. The *pH* of the solution, which can affect ionization of the phosphonic groups.
  2. The *temperature*, as higher temperatures typically enhance solubility.
  3. Interactions with other solutes or solvents in the solution, which can either stabilize or destabilize the solubility.

In summary, while the compound has features that suggest a moderate to good solubility profile in appropriate solvents, the *trade-offs between hydrophilicity and hydrophobicity* make it essential to evaluate solubility in specific conditions for practical applications.

Interesting facts

Interesting Facts about 3-Hydroxy-2-[[6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-5-phosphonooxy-tetrahydropyran-2-yl]oxymethyl]-5-(3-hydroxytetradecanoylamino)-6-phosphonooxy-tetrahydropyran-4-yl] 3-hydroxytetradecanoate

This fascinating compound, known as a complex glycosylated phospholipid, plays a significant role in biochemistry and cellular biology. It contains multiple functional groups that contribute to its unique properties and potential applications:

  • Biological Activity: The intricacies of its structure suggest a potential role in various biological activities, such as cell signaling and membrane interactions.
  • Hydroxyl Groups: The presence of numerous hydroxyl groups often indicates a high degree of polarity, which can influence solubility and reactivity in biological systems.
  • Phosphonate Moieties: These contribute to the compound's ability to interact with biological macromolecules, making it a potential candidate for drug delivery systems.
  • Long-Chain Fatty Acids: The incorporation of tetradecanoyl groups may enhance its membrane fluidity and provide insight into lipid metabolism.

Moreover, its complex structure; characterized by multiple rings and branched chains, beckons the interest of researchers striving to explore natural product synthesis and modifications in fat metabolism. As a scientist might say, "Understanding the intricate relationships among the parts of such compounds offers keys to unlocking the mysteries of biological functions."

Research on such compounds can help elucidate important mechanisms in human health and disease, potentially leading to innovative therapeutic strategies in medicine.

Synonyms
SCHEMBL25930671