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Lipid A

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Identification
Molecular formula
C82H160N2O44P2
CAS number
113-98-4
IUPAC name
6-(1,2-dihydroxyethyl)-4,5-dihydroxy-2-[[6-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-3-phosphonooxy-tetrahydropyran-2-yl]methoxy]tetrahydropyran-2-carboxylic acid
State
State

At room temperature, Lipid A is typically considered a viscous liquid or amorphous solid. As a component of bacterial membranes, it can be isolated in a semi-solid or waxy state.

Melting point (Celsius)
185.00
Melting point (Kelvin)
458.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
1544.00g/mol
Molar mass
1 543.9990g/mol
Density
0.9200g/cm3
Appearence

Lipid A is a part of the lipopolysaccharides (LPS) which is responsible for the biological activity of LPS, including its toxicity. It is usually composed of a disaccharide of glucosamine attached to fatty acids, appearing colorless or as a waxy substance depending on its preparation and specific form.

Comment on solubility

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

The solubility of the compound C82H160N2O44P2, known for its complex structure featuring multiple hydroxyl groups and phosphonates, can be anticipated to be influenced by several factors:

  • Hydroxyl Groups: The presence of multiple hydroxyl (–OH) groups generally enhances **hydrophilicity**, promoting solubility in polar solvents such as water.
  • Phosphate moieties: The phosphate groups contribute to the ionization of the compound, which often leads to increased solubility in aqueous environments, particularly at physiological pH levels.
  • Long hydrocarbon chains: However, the long tetradecanoyl side chains suggest that there might be a **hydrophobic** segment that could hinder solubility in purely polar solvents.
  • Aggregate Formation: The combination of hydrophilic and hydrophobic properties may lead to the formation of micelles or aggregates in solution, which could further complicate direct measurement of solubility.

In conclusion, one could expect this compound to have limited solubility in water while exhibiting better solubility in organic solvents or through formulations that lower hydrophobic interactions. It is essential to consider these aspects when assessing its practical applications in various fields.

Interesting facts

Interesting Facts about 6-(1,2-dihydroxyethyl)-4,5-dihydroxy-2-[[6-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-3-phosphonooxy-tetrahydropyran-2-yl]methoxy]tetrahydropyran-2-carboxylic acid

This complex compound is a fascinating example of the intricate nature of organic molecules and their biological significance. Here are some intriguing details:

  • Biological Relevance: This compound incorporates several hydroxyl and phosphono groups, suggesting it may interact with various biological systems, particularly in signaling pathways or as a bioactive compound.
  • Structural Complexity: The compound comprises multiple tetrahydropyran rings and carboxylic acid functionalities, illustrating the high level of structural complexity often found in natural products and pharmaceuticals.
  • Potential in Drug Development: Molecules with such extensive functionalities are often subject to research for their potential in drug delivery systems or as therapeutic agents in treating diseases.
  • Fatty Acid Interaction: With links to long-chain fatty acids (as indicated by the tetradecanoyl moiety), this compound could be studied for its role in lipid chemistry or membrane biology.
  • Research Interest: Compounds like this one may serve as key intermediates in the synthesis of more complex molecules, drawing interest from synthetic chemists and biochemists alike.

In essence, 6-(1,2-dihydroxyethyl)-4,5-dihydroxy-2-[[6-[[3-hydroxy-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-6-phosphonooxy-tetrahydropyran-2-yl]methoxy]-5-(3-hydroxytetradecanoylamino)-4-(3-hydroxytetradecanoyloxy)-3-phosphonooxy-tetrahydropyran-2-yl]methoxy]tetrahydropyran-2-carboxylic acid is not just a mouthful to say; it represents the intricacies of chemical synthesis and the potential for groundbreaking discoveries in medicinal chemistry.