1,2-Dipalmitoyl-sn-glycero-3-phosphocholine [63-89-8]

1,2-Dipalmitoyl-sn-glycero-3-phosphocholine, often abbreviated as DPPC, is a synthetic phospholipid notable for its critical role in the study of biophysical properties of cell membranes. Structurally, DPPC contains two palmitic acid chains, which are saturated 16-carbon fatty acids, linked to the first and second carbons of a glycerol molecule. The third carbon of the glycerol is bound to a phosphocholine group. This configuration makes DPPC a major component in the formation of lipid bilayers and vesicles due to its amphiphilic nature, with the hydrophobic tails of the palmitic acids and the hydrophilic phosphate choline headgroup. In research, DPPC is extensively used to create model membranes that mimic the lipid bilayer of cell membranes, facilitating the study of membrane dynamics, stability, and interactions with other molecules. The high melting temperature of DPPC results in a gel phase at body temperature, which has been exploited in studies to understand phase transitions within lipid bilayers and their effects on membrane fluidity and function. Additionally, DPPC serves as a fundamental tool in exploring lipid rafts, drug delivery systems via liposomes, and the mechanics of lipid layers, which are essential for understanding more complex biological processes and interactions at the cellular level. Its ability to form stable, well-defined bilayers makes it an invaluable compound in membrane research, particularly in experiments that require controlled environments to replicate cellular conditions.

References:

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2. Induction of immune responses against glycosphingolipid antigens: comparison of antibody responses in mice immunized with antigen associated with liposomes prepared from various phospholipids.  |  Uemura, A., et al. 2005. J Vet Med Sci. 67: 1197-201. PMID: 16397376
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4. Isovaleric, methylmalonic, and propionic acid decrease anesthetic EC50 in tadpoles, modulate glycine receptor function, and interact with the lipid 1,2-dipalmitoyl-Sn-glycero-3-phosphocholine.  |  Weng, Y., et al. 2009. Anesth Analg. 108: 1538-45. PMID: 19372333
5. Curcumin disorders 1,2-dipalmitoyl-sn-glycero-3-phosphocholine membranes and favors the formation of nonlamellar structures by 1,2-dielaidoyl-sn-glycero-3-phosphoethanolamine.  |  Pérez-Lara, A., et al. 2010. J Phys Chem B. 114: 9778-86. PMID: 20666521
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15. Synthesis and properties of dimeric glycerophospholipid: 2,2′-dotriacontanedioylbis(1-palmitoyl-sn-glycero-3-phosphocholine).  |  Yamauchi, K., et al. 1996. J Biochem. 119: 115-9. PMID: 8907184