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Lipid A

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Identification
Molecular formula
C192H348N2O35P2
CAS number
441-62-3
IUPAC name
2-[2-carboxy-6-(1,2-dihydroxyethyl)-2-[[5-(3-dodecanoyloxytetradecanoylamino)-6-[[3-hydroxy-6-[hydroxy(phosphonooxy)phosphoryl]oxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-3-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-5-hydroxy-tetrahydropyran-4-yl]oxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid
State
State

At room temperature, Lipid A is a solid. It is a part of lipopolysaccharides found in the outer membrane of Gram-negative bacteria. Its structure with multiple lipid chains contributes to a substantial crystalline or waxy appearance, making it less soluble in water.

Melting point (Celsius)
180.00
Melting point (Kelvin)
453.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
3284.87g/mol
Molar mass
3 284.8700g/mol
Density
1.1500g/cm3
Appearence

Lipid A typically presents as a white powder in its pure form. Due to its complex structure, which includes several acyl chains and multiple functional groups, it can appear waxy or oily when extracted from sources where it naturally occurs.

Comment on solubility

Solubility of 2-[2-carboxy-6-(1,2-dihydroxyethyl)-2-[[5-(3-dodecanoyloxytetradecanoylamino)-6-[[3-hydroxy-6-[hydroxy(phosphonooxy)phosphoryl]oxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-3-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-5-hydroxy-tetrahydropyran-4-yl]oxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid

The solubility of the compound 2-[2-carboxy-6-(1,2-dihydroxyethyl)-2-[[5-(3-dodecanoyloxytetradecanoylamino)-6-[[3-hydroxy-6-[hydroxy(phosphonooxy)phosphoryl]oxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-3-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-5-hydroxy-tetrahydropyran-4-yl]oxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid (C192H348N2O35P2) can be characterized as follows:

  • High Molecular Weight: The substantial molecular weight indicates that the compound may have limited solubility in common solvents.
  • Hydrophilic Functional Groups: With multiple hydroxyl (-OH) and carboxylic acid groups present, the compound is likely to exhibit some degree of solubility in polar solvents such as water or methanol.
  • Hydrophobic Regions: The presence of long hydrophobic alkyl chains (dodecanoyl and tetradecanoyl groups) suggests potential insolubility in non-polar solvents, making the solubility depend heavily on the solvent environment.

In summary, while the compound may exhibit some solubility in polar environments due to its hydrophilic characteristics, the presence of the extensive hydrophobic regions may contribute to its overall low solubility in non-polar solvents. Further empirical tests would be essential to confirm these solubility traits.

Interesting facts

Interesting Facts About 2-[2-carboxy-6-(1,2-dihydroxyethyl)-2-[[5-(3-dodecanoyloxytetradecanoylamino)-6-[[3-hydroxy-6-[hydroxy(phosphonooxy)phosphoryl]oxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-3-phosphonooxy-4-(3-tetradecanoyloxytetradecanoyloxy)tetrahydropyran-2-yl]methoxy]-5-hydroxy-tetrahydropyran-4-yl]oxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid

The compound, known for its complex structure, is a notable example in the realm of bioactive molecules. Here are some fascinating insights into its properties and potential applications:

  • Structural Intricacies: This compound comprises multiple tetrahydropyran rings, evidencing a rich blend of natural product chemistry and sophisticated molecular architecture.
  • Biological Relevance: With its numerous functional groups, such as carboxylic acids and phosphonooxy groups, it may exhibit significant biological activities including antimicrobial and anti-inflammatory properties.
  • Potential Therapeutic Uses: Its intricate network of functionalities suggests potential applications in drug development, particularly in the area of targeted therapies or as a precursor for synthesizing novel biomolecules.
  • Synthetic Challenges: The synthesis of this compound can illustrate the importance of advanced organic synthesis techniques, making it an excellent case study in organic and medicinal chemistry coursework.
  • Implications in Nutraceuticals: Given its impressive range of structural motifs, it may also be of interest within the field of nutraceuticals, exploring its roles in nutrition and health.

As we delve into the realm of this compound, we unearth the profound complexity of organic molecules and their potential to drive innovations across various fields of science. The study of such compounds not only enriches our understanding but also paves the way for future discoveries.