Palmitoyl Lyso-phosphocholine
[CAS# 17364-16-8]

Identification

• Classification: Biochemical >> Inhibitor
• Name: Palmitoyl Lyso-phosphocholine
• Synonyms: 1-Palmitoyl-rac-glycero-3-phosphocholine
• Molecular Formula: C₂₄H₅₀NO₇P
• Molecular Weight: 495.63
• CAS Registry Number: 17364-16-8
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Palmitoyl lyso-phosphocholine, commonly referred to as 1-palmitoyl-lysophosphatidylcholine, is a naturally occurring lysophospholipid derived from phosphatidylcholine. Structurally, it consists of a glycerol backbone esterified at the sn-1 position with palmitic acid and linked at the sn-3 position to a phosphocholine group, while the sn-2 position bears a free hydroxyl group. It is generated in biological systems primarily through the action of phospholipase A2, which hydrolyzes one fatty acyl chain from phosphatidylcholine. This enzymatic process has been well documented in studies of membrane lipid metabolism and signal transduction.

The identification of lysophosphatidylcholines, including the palmitoyl species, emerged from early investigations into phospholipid structure in the twentieth century. As analytical techniques such as chromatography and nuclear magnetic resonance spectroscopy advanced, researchers were able to characterize the composition and positional distribution of fatty acids in membrane phospholipids. The formation of lysophosphatidylcholine as a product of enzymatic hydrolysis was confirmed through biochemical assays, establishing its presence in plasma and tissues under physiological and pathological conditions.

One major area of application for palmitoyl lyso-phosphocholine has been in biochemical and cell biology research. Because it is a well-defined single-acyl phospholipid, it has been used experimentally to study membrane structure and dynamics. Lysophosphatidylcholines possess distinct physicochemical properties compared with diacyl phospholipids; they can alter membrane curvature and permeability when incorporated into lipid bilayers. Controlled laboratory studies have employed palmitoyl lyso-phosphocholine to examine membrane disruption, micelle formation, and interactions with proteins. These investigations have contributed to understanding how lipid composition influences membrane stability and function.

Palmitoyl lyso-phosphocholine has also been studied for its biological activity as a signaling and bioactive lipid. Elevated concentrations of lysophosphatidylcholine have been detected in oxidized low-density lipoprotein, and experimental work has demonstrated that this lipid can influence endothelial cell behavior, monocyte recruitment, and inflammatory responses. Such findings have established its role as a mediator in inflammatory and vascular processes. Research in this area has relied on purified preparations of defined lysophosphatidylcholine species, including the palmitoyl form, to distinguish the effects of specific fatty acyl chains.

In addition to its role in basic research, palmitoyl lyso-phosphocholine has been used in pharmaceutical and formulation studies. Its amphiphilic nature allows it to function as a component in model membrane systems and liposomal formulations. By incorporating lysophosphatidylcholines into lipid vesicles, investigators have examined drug release properties and membrane fusion behavior. These applications are grounded in experimentally verified properties of lysophospholipids and their interactions with aqueous and lipid phases.

Analytical methods for detecting and quantifying palmitoyl lyso-phosphocholine have been developed as part of lipidomics research. Techniques such as liquid chromatography coupled with mass spectrometry enable precise measurement of this compound in biological samples. Such methodologies have facilitated studies of lipid metabolism, inflammation, and metabolic disorders by providing accurate profiles of lysophospholipid species.

Palmitoyl lyso-phosphocholine therefore represents a well-characterized intermediate in phospholipid metabolism and a widely used reagent in membrane and signaling research. Its discovery through enzymatic studies, structural elucidation by modern analytical chemistry, and documented applications in cell biology and pharmaceutical investigations underscore its established significance in biochemical science.

References

2024. Lysophosphatidylcholines Enriched with cis and trans Palmitoleic Acid Regulate Insulin Secretion via GPR119 Receptor. ACS Medicinal Chemistry Letters.
DOI: 10.1021/acsmedchemlett.3c00263