P3017

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

≥95.5% (GC), ≥98% (TLC)

• Sinónimos: (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
• Fórmula empírica (notación de Hill): C₄₂H₈₂NO₈P
• Número de CAS: 26853-31-6
• Peso molecular: 760.08
• Beilstein: 4173237
• Número CE: 248-056-7
• Número MDL: MFCD00043212
• Código UNSPSC: 12352211
• ID de la sustancia en PubChem: 24898382
• NACRES: NA.77

Propiedades

• Ensayo: ≥95.5% (GC); ≥98% (TLC)
• Formulario: powder
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: WTJKGGKOPKCXLL-RYDYYDTQSA-N

Descripción

Descripción general

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.[1] POPC is associated with alveoli membranes and is a lung surfactant.[2]

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

Aplicación

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[3]
• in the preparation of liposome for fusion with human umbilical vein endothelial cells (HUVEC) to monitor interleukin1 induced clotting process[4]
• with trioleoylglycerol for phase separation studies[5]

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.

Acciones bioquímicas o fisiológicas

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.[2] POPC is typically considered one of the model lipids for biophysical experiments.[1] It undergoes oxidative decomposition upon ozone exposure.[2]

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)