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Lipid A

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Identification
Molecular formula
C176H273O61P2
CAS number
88843-38-5
IUPAC name
[2-[[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate
State
State

At room temperature, Lipid A exists as a solid due to its long-chain fatty acids and relatively high molecular weight. It is part of the lipopolysaccharide (LPS) layer in the outer membrane of Gram-negative bacteria and is crucial for maintaining the integrity and functionality of the bacterial membrane.

Melting point (Celsius)
0.00
Melting point (Kelvin)
0.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
1504.07g/mol
Molar mass
1 504.0700g/mol
Density
1.0500g/cm3
Appearence

Lipid A is generally a pale yellow to white solid at room temperature. It is known for its amphipathic character, having both hydrophilic and hydrophobic parts, which is characteristic of lipids. In its pure form, Lipid A is a waxy solid. However, it is usually not encountered in isolation and is often part of a larger complex, such as lipopolysaccharides in bacterial membranes.

Comment on solubility

Solubility of the Compound

The solubility of the compound 2-[[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate (C176H273O61P2) is an intriguing subject due to its complex structure and extensive functional groups.

Key points regarding its solubility include:

  • Polar and Non-Polar Interactions: Given the presence of hydroxyl (–OH) groups and phosphate (–PO₄) moieties, this compound likely displays a significant degree of polarity, which usually enhances solubility in polar solvents such as water or alcohols.
  • Hydrophobic Regions: The long alkyl chain contributed by the hydroxytetradecanoate portion can introduce hydrophobic characteristics that may limit solubility in highly polar solvents.
  • Solvent Type: It may exhibit better solubility in mixed solvents or solvents with intermediate polarities, where both polar and non-polar interactions can be accommodated.
  • Complexation and Salt Formation: In some cases, interactions with metal ions or formation of salts can enhance solubility, which may be another route to explore for this compound.

In general, while the theoretical assessment suggests potential solubility in polar environments, the actual solubility can vary widely based on factors such as concentration, temperature, and the presence of co-solvents. Therefore, experimental verification of solubility characteristics would be crucial in understanding the practical applications of this compound.

Interesting facts

Interesting Facts about 2-[[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(3-hydroxytetradecanoylamino)tetrahydropyran-4-yl] 3-hydroxytetradecanoate

This complex chemical compound showcases the intricate interplay of various functional groups and structural motifs, making it a fascinating subject of study in chemical and biomedical research. Below are some intriguing facts about this molecule:

  • Complex Structure: The compound features multiple hydroxyl groups and phosphate moieties, which can significantly influence its solubility, reactivity, and biological activity.
  • Pyrimidine Derivative: The presence of a pyrimidine ring is of particular interest as it is a common component in many biologically active molecules and pharmaceuticals, especially in nucleic acid analogs.
  • Biological Relevance: Such compounds may exhibit properties essential for therapeutic applications, particularly in cancer therapy and antiviral treatments, due to their potential interactions with biological macromolecules.
  • Phosphorylation: Phosphate groups are known for their roles in cellular signaling pathways. This compound may possess similar functionalities which could lead to innovative therapeutic strategies.
  • Fatty Acid Moiety: The inclusion of a hydroxytetradecanoate chain indicates potential lipophilicity, which could influence membrane permeability and distribution within biological systems.

In summary, the multifaceted nature of this compound opens up avenues for extensive research into its applications in medicine and biochemistry. As quoted in the field, “The more complex the molecule, the more numerous the secrets it may reveal.” Embracing the complexity of such compounds is key to unraveling their potential benefits.

Synonyms
QDA29360
UDP-3-O-[R-3-hydroxymyristoyl]-N-[R-3-hydroxymyristoyl] glucosamine tris