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P3017

Sigma-Aldrich

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

≥95.5% (GC), ≥98% (TLC)

Synonyme(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

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About This Item

Formule empirique (notation de Hill):
C42H82NO8P
Numéro CAS:
26853-31-6
Poids moléculaire :
760.08
Numéro Beilstein :
4173237
Numéro CE :
248-056-7
Numéro MDL:
MFCD00043212
Code UNSPSC :
12352211
ID de substance PubChem :
24898382
Nomenclature NACRES :
NA.77

Pureté

≥95.5% (GC)
≥98% (TLC)

Forme

powder

Température de stockage

−20°C

Chaîne 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

Clé InChI

WTJKGGKOPKCXLL-RYDYYDTQSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Peter van Hoogevest et al.
European journal of lipid science and technology : EJLST, 116(9), 1088-1107 (2014-11-18)
In pharmaceutical formulations, phospholipids obtained from plant or animal sources and synthetic phospholipids are used. Natural phospholipids are purified from, e.g., soybeans or egg yolk using non-toxic solvent extraction and chromatographic procedures with low consumption of energy and minimum possible
Lin Qiao et al.
The journal of physical chemistry. B, 119(44), 14188-14199 (2015-10-16)
Ambient ozone is a common pollutant in the atmosphere that has an extremely high oxidative ability, can dramatically change the structure and functionality of biomolecules, and is harmful to public health. However, the knowledge about the influence of low-level ozone
M Mijajlovic et al.
Colloids and surfaces. B, Biointerfaces, 104, 276-281 (2013-01-22)
Lipid vesicles have received significant attention in areas ranging from pharmaceutical and biomedical engineering to novel materials and nanotechnology. Microfluidic-based synthesis of liposomes offers a number of advantages over the more traditional synthesis methods such as extrusion and sonication. One
Rafael Atillo Espiritu et al.
Biochemistry, 52(14), 2410-2418 (2013-03-13)
Theonellamides (TNMs) are members of a distinctive family of antifungal and cytotoxic bicyclic dodecapeptides isolated from the marine sponge Theonella sp. Recently, it has been shown that TNMs recognize 3β-hydroxysterol-containing membranes, induce glucan overproduction, and damage cellular membranes. However, to
Heinrich Sandermann
FEBS letters, 554(1-2), 165-168 (2003-11-05)
Octanol-1/water partitioning currently provides the most widely used model system to simulate both phospholipid target lipids and triglyceride storage lipids. A differentiation between the two lipid classes is now achieved by making use of a water-induced lipid phase separation. Coefficients
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