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| 50mg |
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| 100mg |
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| 250mg |
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| Targets |
1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is a phospholipid that serves as a structural component of biological membranes. It does not have a specific molecular target like an enzyme or receptor. Instead, its role is to form the lipid bilayer that constitutes the cell membrane. The phospholipid molecule consists of a glycerol backbone, two fatty acid chains (palmitic acid at sn-1 and oleic acid at sn-2), and a phosphocholine head group. The fatty acid chains provide hydrophobic interactions, while the phosphocholine head group provides hydrophilic interactions. These amphipathic properties allow POPC to spontaneously form lipid bilayers in aqueous environments. POPC is often used as a model membrane system because it forms stable, fluid bilayers that resemble the properties of natural cell membranes. It is also used in combination with cholesterol and other lipids to create more complex membrane models.
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| ln Vitro |
1-Palmitoyl-2-oleoyl-sn-glycerol-3-PC (POPC) is a phospholipid with 16:0 and 18:1 fatty acids at the sn-1 and sn-2 positions, respectively [1].
In vitro, 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is used as a component of model membranes for studying lipid bilayer properties. It is used in the formulation of liposomes, which are spherical vesicles composed of lipid bilayers. Liposomes can be used to encapsulate drugs or other molecules for delivery to cells. POPC is also used in studies of membrane protein function, as it can provide a lipid environment that supports the activity of membrane proteins. The phospholipid's fluidity and phase behavior can be studied using techniques such as differential scanning calorimetry (DSC), nuclear magnetic resonance (NMR) spectroscopy, and fluorescence spectroscopy. POPC is often used in combination with cholesterol to study the effects of cholesterol on membrane properties. The phospholipid is also used in Langmuir-Blodgett films and supported lipid bilayers for surface-based studies. |
| ln Vivo |
In vivo, 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is a natural component of cell membranes. It is not typically administered as a drug but is used as a component of liposomal drug delivery systems. When formulated into liposomes, POPC can be used to encapsulate drugs and deliver them to target tissues. The liposomes can be designed to be long-circulating or to target specific cells. The in vivo behavior of POPC-containing liposomes depends on their size, charge, and surface modifications. The phospholipid is metabolized in the body by phospholipases, which cleave the fatty acid chains. The fatty acids are then used for energy or incorporated into other lipids. POPC is generally considered to be biocompatible and biodegradable.
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| Enzyme Assay |
Cell-free assays for 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) typically involve studying its physical and chemical properties in model membrane systems. For example, the fluidity of POPC bilayers can be measured using fluorescence anisotropy of membrane-embedded probes. The phase transition temperature of POPC can be measured using differential scanning calorimetry (DSC). The permeability of POPC bilayers to various molecules can be measured using fluorescence or radiolabeled tracers. The interaction of POPC with other lipids, such as cholesterol, can be studied using these same techniques. POPC is also used in surface plasmon resonance (SPR) and quartz crystal microbalance (QCM) studies to measure the binding of proteins or other molecules to lipid bilayers. These assays do not involve enzymatic reactions but rather biophysical measurements of membrane properties.
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| Cell Assay |
For in vitro cellular assays, 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is typically used as a component of liposomes for drug delivery studies. Cells are incubated with POPC-containing liposomes that encapsulate a fluorescent dye or a drug. The uptake of the liposomes by the cells is measured using flow cytometry or fluorescence microscopy. The cytotoxicity of the liposomes is assessed using an MTT or resazurin assay. The ability of the liposomes to deliver their cargo to the cells is evaluated by measuring the intracellular concentration of the encapsulated molecule. POPC is also used in studies of membrane fusion and cell-cell interactions. In these studies, cells are labeled with fluorescent dyes that are incorporated into the membrane, and the fusion of cells or liposomes is monitored by fluorescence microscopy.
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| Animal Protocol |
In vivo animal experiments involving 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) typically focus on its use as a component of liposomal drug delivery systems. In such a study, mice or rats are injected intravenously with liposomes composed of POPC and other lipids, encapsulating a drug or a fluorescent tracer. The pharmacokinetics of the liposomes are studied by measuring the concentration of the encapsulated molecule in the blood and tissues at various time points. The biodistribution of the liposomes is assessed by imaging or by measuring the fluorescence in tissues. The therapeutic efficacy of the drug-loaded liposomes is evaluated in disease models, such as tumor-bearing mice. The toxicity of the liposomes is assessed by monitoring body weight, blood chemistry, and histopathology. These studies provide critical data on the in vivo behavior of POPC-containing liposomes.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties for 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) are not applicable in the traditional sense, as it is not a drug but a lipid. When formulated into liposomes, the pharmacokinetics of the liposomes are determined by the properties of the liposome as a whole, including size, charge, and surface modifications. POPC-containing liposomes are typically cleared from the circulation by the reticuloendothelial system (RES), primarily in the liver and spleen. The half-life of the liposomes in the blood can be prolonged by using PEGylated lipids or by reducing the size of the liposomes. The metabolism of POPC involves the cleavage of the fatty acid chains by phospholipases. The fatty acids are then used for energy or incorporated into other lipids. The phosphocholine head group is also metabolized.
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| Toxicity/Toxicokinetics |
1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is generally considered to be non-toxic, as it is a natural component of cell membranes. However, when formulated into liposomes, the toxicity of the liposomes depends on the composition of the liposomes and the encapsulated drug. High doses of liposomes can cause RES saturation and lead to toxicity. The phospholipid itself is biodegradable and biocompatible. No specific toxicity studies, such as acute or chronic toxicity, have been detailed in the public domain. As a research chemical, standard safety precautions should be observed when handling this compound. The compound is not approved for human therapeutic use as a drug, but it is used as an excipient in pharmaceutical formulations.
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| References |
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| Additional Infomation |
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol-3-phosphate choline is a phosphatidylcholine 34:1, wherein the 1- and 2-acyl groups are designated as hexadecanoyl (palmitoyl) and 9Z-octadecenoyl (oleoyl), respectively. It is a mouse metabolite. It is a phosphatidylcholine 34:1, and also a 1-acyl-2-oleoyl-sn-glycerol-3-phosphate choline betaine. It is functionally related to hexadecanoic acid and oleic acid. 1-Palmyl-2-oleoyl-sn-glycerol-3-phosphate choline has been reported in Streptomyces roseum, Drosophila melanogaster, and other organisms with relevant data. PC (16:0/18:1(9Z)) is a metabolite found or produced in Saccharomyces cerevisiae.
1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is a research tool for studying membrane structure and function. It is used in liposome formulation. It is a natural component of cell membranes. It is not a drug but an excipient. |
| Molecular Formula |
C₄₂H₈₂NO₈P
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|---|---|
| Molecular Weight |
760.08
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| Exact Mass |
759.577
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| CAS # |
26853-31-6
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| Related CAS # |
1-Palmitoyl-2-oleoyl-sn-glycero-3-PC-d31;179093-76-6;1-Palmitoyl-2-oleoyl-sn-glycero-3-PC-d82;2260669-94-9
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| PubChem CID |
5497103
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| Appearance |
White to off-white solid powder
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| LogP |
11.42
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
41
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| Heavy Atom Count |
52
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| Complexity |
899
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
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| InChi Key |
WTJKGGKOPKCXLL-VYOBOKEXSA-N
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| InChi Code |
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
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| Chemical Name |
[(2R)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
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| Synonyms |
1Palmitoyl2oleoylsnglycero3PC; 1 Palmitoyl 2 oleoyl sn glycero 3 PC
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
Ethanol : ~50 mg/mL (~65.78 mM)
DMSO :< 1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (1.64 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 1.25 mg/mL (1.64 mM) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.25 mg/mL (1.64 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3157 mL | 6.5783 mL | 13.1565 mL | |
| 5 mM | 0.2631 mL | 1.3157 mL | 2.6313 mL | |
| 10 mM | 0.1316 mL | 0.6578 mL | 1.3157 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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