1,2-Dimyristoyl-sn-glycero-3-phosphocholine

• CAT Number: R027477
• CAS Number: 18194-24-6
• Molecular Formula: C36H72NO8P
• Molecular Weight: 677.945
• Purity: ≥95%
• Synonyms: 3,5,9-Trioxa-4-phosphatricosan-1-aminium, 4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxotetradecyl)oxy]-, hydroxide, inner salt, 4-?oxide, (R)-; Choline, hydroxide, dihydrogen phosphate, inner salt, ester with 1,2-dimyristin, L- (8CI); Choline, phosphate
• Target: Liposome
• Storage: -20°C
• IUPAC Name: [(2R)-2,3-di(tetradecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• InChI: InChI=1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/m1/s1
• InChIKey: CITHEXJVPOWHKC-UUWRZZSWSA-N
• SMILES: CCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC

1,2-Dimyristoyl-sn-glycero-3-phosphocholine(CAT: R027477) is a synthetic phospholipid used in the study of lipid bilayers and liposomes. With 14:0 fatty acids at both the sn-1 and sn-2 positions, it mimics a naturally occurring lipid structure. The compound’s significance lies in its application as a component in liposome formulations, which are widely used to model biological membranes and study membrane properties. 1,2-Dimyristoyl-sn-glycero-3-phosphocholine provides researchers with a controlled and reproducible system for investigating various aspects of lipid bilayers, membrane structure, and interactions with other molecules.

Reference

1. M. Navab et al. “Oral Synthetic Phospholipid (DMPC) Raises High-Density Lipoprotein Cholesterol Levels, Improves High-Density LipoproteinFunction, and Markedly Reduces Atherosclerosis in Apolipoprotein E–Null Mice” Circulation, vol. 108 pp. 1735-1739, 20032. M. Billah and J. Anthes “The regulation and cellular functions of phosphatidylcholine hydrolysis” Biochemistry Journal, Vol. 269 pp. 281-291, 19903. J. Exton “Signaling through Phosphatidylcholine Breakdown” The Journal of Biological Chemistry, Vol. 265(1) pp. 1-4, 19904. Z. Li and D. Vance “Phosphatidylcholine and choline homeostasis” Journal of Lipid Research, Vol. 49 pp. 1187-1194, 2008