P3017

2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine

≥95.5% (GC), ≥98% (TLC)

• Synonym(s): (7R,17Z)-4-Hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphahexacos-17-en-1-aminium 4-oxide, inner salt, 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine, 1-Hexadecanoyl-2-(cis-9-octadecenoyl)-sn-glycero-3-phosphocholine, 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, 3-sn-Phosphatidylcholine, 2-oleoyl-1-palmitoyl, L-β-Oleoyl-γ-palmitoyl-α-lecithin, PC(16:0/18:1(9Z)), PC(16:0/18:1), PC(16:0/18:1w9), POPC
• Empirical Formula (Hill Notation): C₄₂H₈₂NO₈P
• CAS Number: 26853-31-6
• Molecular Weight: 760.08
• Beilstein/REAXYS Number: 4173237
• EC Number: 248-056-7
• MDL number: MFCD00043212
• UNSPSC Code: 12352211
• PubChem Substance ID: 24898382
• NACRES: NA.77

Properties

• assay: ≥95.5% (GC); ≥98% (TLC)
• form: powder
• storage temp.: −20°C
• SMILES string: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C\CCCCCCCC
• InChI: 1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20+/t40-/m1/s1
• InChI key: WTJKGGKOPKCXLL-RYDYYDTQSA-N

Description

General description

2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (POPC) mimics mammalian phospholipid composition. It comprises a saturated chain (palmitic acid) in the sn-1 position and unsaturated chain (oleic acid) in the sn-2 position,. It is an excellent synthetic substitute for EPC. POPC is associated with alveoli membranes and is a lung surfactant.

Non-pyrogenic, well-defined liposomes, loaded with a molecule of choice, are formed by a single hydration step.

Application

2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine has been used:

• in the liposome preparation for lipid binding assay of monogalactosyldiacylglycerol synthase (MGD1) activity in plant samples
• in the preparation of liposome for fusion with human umbilical vein endothelial cells (HUVEC) to monitor interleukin1 induced clotting process
• with trioleoylglycerol for phase separation studies

The effect of non-ionic detergent on liposomes was studied with giant POPC liposomes. Increasing concentrations of detergent cause tubular protrusions, then indentations, to develop on spherical liposomes. At higher detergent concentrations, the liposomes burst.

Biochem/physiol Actions

2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (POPC) reduces air-liquid interface associated surface tension. It is effective in alleviating alveolar collapse and pulmonary edema. POPC is typically considered one of the model lipids for biophysical experiments. It undergoes oxidative decomposition upon ozone exposure.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)