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Lecithin

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Identification
Molecular formula
C42H84NO9P
CAS number
8002-43-5
IUPAC name
2-[(2-acetoxy-3-hexadecanoyloxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium
State
State

At room temperature, lecithin is typically in a waxy solid state. It is often processed into powders and liquids for commercial use.

Melting point (Celsius)
-2.00
Melting point (Kelvin)
271.15
Boiling point (Celsius)
650.00
Boiling point (Kelvin)
923.15
General information
Molecular weight
770.12g/mol
Molar mass
770.1230g/mol
Density
1.0305g/cm3
Appearence

Lecithin is a yellow-brownish fatty substance occurring in animal and plant tissues. It appears as a waxy, gummy, or powdery substance, depending on its purity and source. In its pure form, it is generally a white powder but commercially often appears in a more complex form.

Comment on solubility

Solubility of 2-[(2-acetoxy-3-hexadecanoyloxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium (C42H84NO9P)

The solubility of 2-[(2-acetoxy-3-hexadecanoyloxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium is influenced by its unique structure, which includes both hydrophobic and hydrophilic components. Its behavior in solution can be summarized as follows:

  • Hydrophobic Character: The long hexadecanoyloxy chain contributes to significant hydrophobic interactions, which tend to reduce solubility in polar solvents such as water.
  • Hydrophilic Functional Groups: The presence of the trimethylammonium group enhances the compound's affinity for water, promoting solubility due to ionic interactions.
  • Amphiphilic Nature: Being amphiphilic, this compound can exhibit varying solubility depending on the solvent system. It may form micelles or aggregates in aqueous solutions, thereby increasing solubility at certain concentrations.
  • Temperature Effects: Solubility can also be temperature-dependent, with higher temperatures typically aiding in the dissolution process due to increased molecular motion.

In summary, while this compound may have limited solubility in pure water, its amphiphilic characteristics allow it to dissolve effectively in mixed solvents or at higher concentrations. The intricate balance of hydrophobic and hydrophilic attributes plays a crucial role in its solubility behavior.

Interesting facts

Exploring 2-[(2-acetoxy-3-hexadecanoyloxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium

This compound is a fascinating example of an organic ammonium salt that plays a significant role in various chemical and biological contexts. Here are some interesting aspects of this molecule:

  • Amphiphilic Nature: The structure of this compound suggests it possesses both hydrophilic and hydrophobic regions. This amphiphilic characteristic allows it to interact with both aqueous and fatty environments, making it ideal for applications in drug delivery and biomedicine.
  • Biological Activity: Compounds like this one are often studied for their potential pharmacological properties. The incorporation of long-chain fatty acids, such as hexadecanoyloxy groups, is particularly important in enhancing membrane permeability, which is a crucial factor in drug design.
  • Phosphorylation: The phosphoryl component in the structure is significant since phosphates are key players in various biological processes, including signaling pathways in cells. This feature may impart unique biological functionalities to the compound.
  • Cationic Amphiphiles: As a cationic compound, it can interact with negatively charged biological membranes, which raises its profile as a potential agent for drug delivery systems where membrane fusion is critical.
  • Synthetic Versatility: The synthetic routes leading to the formation of this compound can involve various reactions including esterification and phosphorylation, showcasing its synthetic accessibility in organic chemistry.

In summary, 2-[(2-acetoxy-3-hexadecanoyloxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium serves as a classic example of a modern compound that bridges organic chemistry with biological applications, making it a subject of great interest in the fields of medicinal and pharmaceutical chemistry.

Synonyms
SCHEMBL21248464