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C18:1-C16:0 Phosphatidylcholine

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Identification
Molecular formula
C29H60NO8P
CAS number
597-56-4
IUPAC name
(2-hydroxy-3-octadecoxy-propyl) 2-(trimethylammonio)ethyl phosphate
State
State

The compound is typically found as a solid at room temperature, with a waxy texture due to its long hydrophobic fatty acid chains.

Melting point (Celsius)
-20.00
Melting point (Kelvin)
253.15
Boiling point (Celsius)
322.00
Boiling point (Kelvin)
595.15
General information
Molecular weight
495.75g/mol
Molar mass
495.7490g/mol
Density
0.9686g/cm3
Appearence

The compound appears as an off-white to pale yellow waxy solid, reflecting its fatty alkyl chains typical of phosphatidylcholines.

Comment on solubility

Solubility of (2-hydroxy-3-octadecoxy-propyl) 2-(trimethylammonio)ethyl phosphate

The compound (2-hydroxy-3-octadecoxy-propyl) 2-(trimethylammonio)ethyl phosphate, with the chemical formula C29H60NO8P, exhibits distinct solubility characteristics that are influenced by its molecular structure. This amphiphilic compound contains both hydrophilic (water-attracting) and hydrophobic (water-repelling) components, making its solubility behavior particularly interesting.

Solubility Characteristics

  • Hydrophilic nature: The presence of the phosphate group and the quaternary ammonium cation contributes to the hydrophilic properties of the compound, enabling some degree of solubility in aqueous environments.
  • Hydrophobic characteristics: The long alkyl chain (octadecyloxy) imparts significant hydrophobic character, which may limit solubility in polar solvents like water.
  • Solvent interactions: The solubility is likely to improve in mixed solvents or in the presence of surfactants, where the amphiphilic nature can modify interfacial tension.

In general, one might expect that this compound could exhibit low to moderate solubility in water, while demonstrating a higher affinity for non-polar solvents, such as organic solvents. As a result, its solubility can be described as a delicate balance between hydrophilic and hydrophobic interactions.

Understanding the solubility of such compounds is crucial in applications ranging from pharmaceuticals to industrial formulations, influencing their behavior in various environments and influencing their practical use.

Interesting facts

Interesting Facts about (2-hydroxy-3-octadecoxy-propyl) 2-(trimethylammonio)ethyl phosphate

The compound known as (2-hydroxy-3-octadecoxy-propyl) 2-(trimethylammonio)ethyl phosphate is a fascinating, complex molecule that falls under the category of phospholipids. Here are some engaging facts about this compound:

  • Structural Diversity: This compound features a unique dual structure combining both hydrophobic and hydrophilic components, which makes it an excellent candidate for applications in emulsification and stabilization of colloidal systems.
  • Biological Relevance: Phospholipids are key components of cell membranes. This compound’s structure is similar to natural phospholipids, suggesting its potential role in biological membranes, cell signaling, and the delivery of drugs.
  • Amphiphilic Nature: Due to its amphiphilic characteristics, it can self-assemble into bilayers or micelles, a property that is highly useful for the development of drug delivery systems or as surfactants in various industrial applications.
  • Polycationic Properties: The presence of a trimethylammonio group gives this compound polycationic properties, which can enhance its interaction with negatively charged biological molecules, such as DNA and RNA, opening avenues for gene delivery.
  • Application in Nanotechnology: Its unique properties enable its use in nanotechnology, such as in the formulation of nanoparticles for targeted therapies or as a vehicle for contrast agents in imaging techniques.

The versatility of (2-hydroxy-3-octadecoxy-propyl) 2-(trimethylammonio)ethyl phosphate exemplifies how advances in organic and medicinal chemistry can lead to innovative solutions across different scientific fields. As research continues, the full potential of such complex molecules is far from being fully realized.

Synonyms
Lyso-PAF c-18
Lyso-PAF (C18)
72490-82-5
(2-hydroxy-3-octadecoxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
1-octadecylglycero-3-phosphocholine
34240-68-1
LPC O-18:0
2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
Ro 14-0859
CHEMBL229361
SCHEMBL7592842
CHEBI:91144
DTXSID20955785
lyso-PC (O-18:0/0:0)
4,7-DihydroXY-N,N,N-trimethyl-2,5,9-trioxa-4-phosphaheptacosan-1-aminium hydroxide, inner salt, 4-oxide, (+-)-
FO111149
FO177703
1-O-Octadecyl-rac-glycero-3-phosphocholine
DB-055878
Q27163081
(2-Hydroxy-3-octadecoxypropyl)2-(trimethylazaniumyl)ethyl phosphate
3,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-, hydroxide, inner salt, 4-oxide, (+-)-