Merck
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P3017

Sigma-Aldrich

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

≥95.5% (GC), ≥98% (TLC)

Synonym(s):
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine, (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-(cis-9-octadecenoyl)-sn-glycero-3-phosphocholine, PC(16:0/18:1), 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine, PC(16:0/18:1(9Z)), 3-sn-Phosphatidylcholine, 2-oleoyl-1-palmitoyl, POPC, PC(16:0/18:1w9), L-β-Oleoyl-γ-palmitoyl-α-lecithin
Empirical Formula (Hill Notation):
C42H82NO8P
CAS Number:
Molecular Weight:
760.08
Beilstein:
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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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

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.
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

Packaging

10, 25, 100 mg in ampule

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

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
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

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