P3017

2-Oleoyl-1-Palmitoyl-sn-Glycero-3-Phosphocholin

≥95.5% (GC), ≥98% (TLC)

• Synonym(e): (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-oxid, inneres Salz, 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholin, 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholin, 3-sn-Phosphatidylcholin, 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
• Empirische Formel (Hill-System): C₄₂H₈₂NO₈P
• CAS-Nummer: 26853-31-6
• Molekulargewicht: 760.08
• UNSPSC Code: 12352211
• NACRES: NA.77
• PubChem Substance ID: 24898382
• EC Number: 248-056-7
• Beilstein/REAXYS Number: 4173237
• MDL number: MFCD00043212
• Assay: ≥95.5% (GC), ≥98% (TLC)
• Form: powder

Eigenschaften

• Quality Segment: 200
• 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

Beschreibung

General description

Nicht-pyrogene, eindeutig definierte Liposomen, beladen mit einem beliebigen Molekül, werden mit einem einzigen Hydrationsschritt gebildet.

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]

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[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.

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

Sicherheitshinweise

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