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Edelfosine

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Identification
Molecular formula
C27H58NO7P
CAS number
77286-66-9
IUPAC name
2-[(2-acetoxy-3-hexadecoxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium
State
State

At room temperature, Edelfosine is typically in a solid state. Its waxy and slightly sticky nature may give it a semi-solid texture at slightly higher temperatures.

Melting point (Celsius)
96.00
Melting point (Kelvin)
369.00
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.00
General information
Molecular weight
523.73g/mol
Molar mass
523.5000g/mol
Density
1.0280g/cm3
Appearence

Edelfosine typically appears as an off-white to pale yellow solid. It is known for being waxy and slightly sticky to the touch. The compound can be obtained in a solid state and tends to be amorphous, lacking a definitive crystalline structure.

Comment on solubility

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

The solubility characteristics of the compound 2-[(2-acetoxy-3-hexadecoxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium (C27H58NO7P) can be understood through several key factors:

  • Polarity: The presence of the phosphoryl group and several hydroxyl groups typically contributes to the polarity of the molecule, enhancing its solubility in polar solvents like water.
  • Hydrophobic Interactions: The long hexadecoxy chain indicates significant hydrophobic characteristics, which may limit solubility in aqueous environments but enhance solubility in organic solvents.
  • Ammonium Group: The trimethylammonium moiety is known to increase solubility in aqueous solutions due to its ability to interact favorably with water molecules.

As a result, this compound may exhibit:

  1. Moderate to high solubility in aqueous media, especially when influenced by temperature and pH.
  2. Enhanced solubility in organic solvents, owing to the presence of the long-chain alkyl group.
  3. Potential aggregation behavior in solution due to its amphiphilic nature, possibly forming micelles or other complex structures.

In conclusion, the solubility of 2-[(2-acetoxy-3-hexadecoxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium is multifaceted, highlighting the interplay between hydrophilic and hydrophobic components within the molecule. It is important to consider both the solvent’s nature and environmental conditions when assessing solubility performance.

Interesting facts

Interesting Facts about 2-[(2-acetoxy-3-hexadecoxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium

This compound is an intriguing member of the quaternary ammonium compounds family, known for their diverse applications in various fields ranging from biomedical to industrial uses. Here are some interesting aspects of this unique compound:

  • Quaternary Structure: The trimethylammonium component indicates a fully charged nitrogen atom, which is characteristic of quaternary ammonium compounds. These compounds are well-known for their surfactant properties and ability to act as cationic agents.
  • Biological Applications: Its structure suggests potential uses in the pharmaceutical field, particularly as a drug delivery system due to the presence of the phosphoryl group, which can interact favorably with biological membranes.
  • Stability and Interaction: The long hydrocarbon chain provided by the hexadecoxy group contributes to lipid bilayer interactions, which can enhance the compound's ability to penetrate cell membranes. This property is significant for research in drug design and delivery.
  • Organizational Role: The multifunctional nature of this compound makes it a candidate for products aimed at anti-microbial activity or as a surfactant in formulations, showcasing its diverse applicability in modern chemistry.
  • Historical Insight: Compounds in similar classes have been historically used in the development of antiseptics and in various cosmetic formulations, highlighting the ongoing relevance of quaternary ammonium compounds in consumer products.

In summary, 2-[(2-acetoxy-3-hexadecoxy-propoxy)-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium is more than just a complex name—it represents a fascinating union of chemistry and application-driven potential in a variety of disciplines. As one delves deeper into its compounds, the possibilities for innovation and discovery expand considerably.

Synonyms
77286-68-1
rac-Platelet activating factor
2-[(2-acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium
Paf enantiomer
SCHEMBL12235513
DTXSID10274371
DTXSID20868306
1-O-Palmityl-2-acetyl-rac-glycero-3-phosphocholine, ~99%
7-(Acetyloxy)-4-hydroxy-N,N,N-trimethyl-4-oxo-3,5,9-trioxa-4lambda~5~-phosphapentacosan-1-aminium