1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
• CAS No.: 26853-31-6
• Molecular Formula: C₄₂H₈₂NO₈P
• Molecular Weight: 760.089
• Hs Code.: 2923900090
• European Community (EC) Number: 248-056-7
• UNII: TE895536Y5
• DSSTox Substance ID: DTXSID101029642
• Wikipedia: POPC
• Wikidata: Q10860475
• Metabolomics Workbench ID: 13298
• Mol file: 26853-31-6.mol

Synonyms:1-palmitoyl-2-oleoyl-lecithin;1-palmitoyl-2-oleoyl-phosphatidylcholine;1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylcholine;1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine;1-palmitoyl-2-oleoylphosphatidylcholine;1-palmitoyl-2-oleoylphosphatidylcholine, (R)-(Z)-isomer;1-palmotoyl-2-oleoylglycero-3-phosphocholine;1-POPC;alpha-phosphatidylcholine-beta-oleoyl-gamma-palmitoyl;beta-oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholine;palmitoyloleoylphosphatidylcholine;POPC lipid

Chemical Property of 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine

Chemical Property:

• Melting Point: -3 °C
• PSA: 121.00000
• LogP: 12.23820
• Storage Temp.: −20°C
• XLogP3: 13.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 41
• Exact Mass: 759.57780557
• Heavy Atom Count: 52
• Complexity: 899

Purity/Quality:

97% ^*data from raw suppliers

1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Ambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
• Recent EU Clinical Trials: A placebo-controlled, double-blind, randomized trial to compare the effect of treatment on plaque burden as determined by intravascular ultrasound and to evaluate the efficacy, pharmacokinetics, safety, and tolerability of MDCO-216 given as multiple weekly infusions in subjects with a recent acute coronary syndrome.
• Description: 1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is a phospholipid containing 16:0 and 18:1 fatty acids at the sn-1 and sn-2 positions, respectively. It belongs to a class of phospholipids that are a major component of biological membranes. 1-PALMITOYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE can be used for liposome production in order to study the properties of lipid bilayers. 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPhtCho), is a phosphatidylcholine, that belongs to a class of phospholipids that are a major component of biological membranes. 1-PALMITOYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE has been shown to decrease the expression of α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptor subunit GluR1 on the plasma membrane of CA1 region of rat hippocampal slices.
• Uses: 16:0-18:1 PC has been used in the preparation of liposomes for the muramyl tripeptide encapsulation. It has also been used in the preparation of membrane scaffold protein 1 nanodisc. 16:0-18:1 PC may be used in the synthesis of discoidal reconstituted high-density lipoproteins. 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. Glycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.

Technology Process of 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine

There total 16 articles about 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

methyl iodide (74-88-4) + (Z)-Octadec-9-enoic acid (R)-2-[(2-dimethylamino-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester (1490-20-6) → 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (6753-55-5,26662-91-9,26662-92-0,26853-31-6,67738-47-0,109958-90-9)

Guidance literature:

With cyclohexylamine; In methanol; for 15h;

Reference yield: 64.0%

2-chloroethyl phosphorodichloridate (1455-05-6) + 1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol (29541-66-0) + trimethylamine (75-50-3) → 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (6753-55-5,26662-91-9,26662-92-0,26853-31-6,67738-47-0,109958-90-9)

Guidance literature:

2-chloroethyl phosphorodichloridate; 1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol; With triethylamine; In dichloromethane;

With water; triethylamine; In dichloromethane;

trimethylamine; In ethanol; at 70 - 80 ℃; for 72h;

DOI:10.1248/cpb.47.1659

Reference yield:

citicoline (987-78-0) + 1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol (29541-66-0) → 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (6753-55-5,26662-91-9,26662-92-0,26853-31-6,67738-47-0,109958-90-9)

Guidance literature:

cytidinediphosphocholine phosphocholinetransferase;

DOI:10.1021/ja00021a043

upstream raw materials:

citicoline

1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol

2-chloroethyl phosphorodichloridate

trimethylamine

Downstream raw materials:

1-palmitoyl-sn-glycero-3-phosphocholine

1-oleoyl-L-lysophosphatidylcholine

2-(octadec-cis-9-enoyl)-sn-glycero-3-phosphocholine

Refernces

Supramolecular aggregates of azobenzene phospholipids and related compounds in bilayer assemblies and other microheterogeneous media: Structure, properties, and photoreactivity

10.1021/ja971291n

The study focuses on the synthesis and investigation of azobenzene phospholipids (APLs) in aqueous dispersions, both in pure form and when mixed with saturated and unsaturated phospholipids. The research explores the structures of the assemblies formed by these APLs, which include various forms such as large plates, and their ability to form "H" aggregates with typical aggregation numbers being multiples of three. The study utilizes techniques like microcalorimetry, dynamic light scattering, cryo-transmission electron microscopy, and reagent entrapment to analyze the assemblies. It also examines the photoreactivity of the azobenzenes, which can photoisomerize to produce cis-rich photostationary states. Interestingly, the cis-azobenzenes do not aggregate and can be reverted back to the trans form through irradiation or thermal means. The research further explores the controlled release of entrapped reagents from vesicles formed by mixed aqueous dispersions of trans-APLs with other phospholipids, demonstrating that photoisomerization can induce reagent release. The study provides insights into how aggregation influences the microstructure and macroscopic properties of the assemblies, with potential applications in drug delivery and other areas requiring photoresponsive materials.