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Merck

P3017

Sigma-Aldrich

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

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About This Item

Empirische Formel (Hill-System):
C42H82NO8P
CAS-Nummer:
Molekulargewicht:
760.08
Beilstein:
4173237
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352211
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥95.5% (GC)
≥98% (TLC)

Form

powder

Lagertemp.

−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

InChIKey

WTJKGGKOPKCXLL-RYDYYDTQSA-N

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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