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P3017

Sigma-Aldrich

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

≥95.5% (GC), ≥98% (TLC)

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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:
Molecular Weight:
760.08
Beilstein/REAXYS Number:
4173237
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
P4142P4329P0763
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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.

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)


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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
Birgitta Rosengren et al.
Arteriosclerosis, thrombosis, and vascular biology, 26(7), 1579-1585 (2006-04-08)
To study the distribution of group V secretory phospholipase A2 (sPLA2) in human and mouse lesions and compare its expression by human vascular cells, its activity toward lipoproteins, and the interaction with arterial proteoglycans (proteoglycans) with those of sPLA2-IIA. In
Maik Hadorn et al.
Scientific reports, 1, 168-168 (2012-02-23)
Today, free-standing membranes, i.e. liposomes and vesicles, are used in a multitude of applications, e.g. as drug delivery devices and artificial cell models. Because current laboratory techniques do not allow handling of large sample sizes, systematic and quantitative studies on

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