1-Palmitoyl-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-Palmitoyl-sn-glycero-3-phosphocholine
• CAS No.: 17364-16-8
• Molecular Formula: C24H50NO7P
• Molecular Weight: 495.637
• European Community (EC) Number: 306-536-4
• UNII: JD6PYE3XUX
• DSSTox Substance ID: DTXSID30914020
• Wikidata: Q27105001
• Metabolomics Workbench ID: 14994
• ChEMBL ID: CHEMBL3093100
• Mol file: 17364-16-8.mol

Synonyms:1-O-hexadecylpropanediol 3-phosphorylcholine;1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine;1-palmitoyl-sn-glycerol-3-phosphorylcholine;1-palmitoylglycerol-3-phosphorylcholine;1-palmitoyllysophosphatidylcholine;hydroxide inner salt(+-)-isomer of We 201;hydroxide inner salt(R)-isomer of We 201;hydroxide inner salt(S)-isomer of We 201;LYSO-PC;palmitoyl lysophosphatidylcholine;We 201;We-201;1-palmitoyl-2-lysophosphatidylcholine;1-Pam-2-lysoPtdCho

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

Chemical Property:

• Melting Point: 253 °C
• PSA: 114.93000
• LogP: 5.64980
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 24
• Exact Mass: 495.33248993
• Heavy Atom Count: 33
• Complexity: 517

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Palmitoyl-sn-glycero-3-phosphocholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Description: 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC is the ubiquitous lipid species generated following phospholipase A2 (PLA2) hydrolysis of phosphatidylcholine. It increases the production of reactive oxygen species (ROS) and decreases superoxide dismutase (SOD) and endothelial nitric oxide synthase (eNOS) protein levels and phosphorylation of ERK1/2 in human umbilical vein endothelial cells (HUVECs) when used at a concentration of 125 μM. 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC potentiates the secretion of IL-6, IL-1β, IL-12, and TNF-α in LPS-stimulated M1 macrophages, but has no effect on CD163, CD206, CD36, or IL-10 in LPS-stimulated M2 macrophages when used at concentrations of 0.3 and 1.0 μM. It increases TGF-β1 production and enhances Foxp3 protein levels in Treg cells in isolated human peripheral blood when used at a concentration of 10 μM. 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC enhances neutrophil function, bacterial clearance, and survival in mouse models of sepsis when administered at a dose of 10 mg/kg.
• Uses: A lipid biomarker for stable and unstable heart disease. 16:0 Lyso PC has been used to reveal the central role of the adipocyte inflammasome in homocysteine-induced insulin resistance. It has also been used for lipid extraction and mass spectrometry analysis.

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

There total 43 articles about 1-Palmitoyl-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: 99.0%

L-dipalmitoylphosphatidylcholine (63-89-8) → 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5)

Guidance literature:

With sodium docusate; phospholipase A₂; In aq. buffer; at 40 ℃; for 0.5h; pH=8.5;

DOI:10.1371/journal.pone.0157278

Reference yield: 98.0%

n-hexadecanoyl chloride (112-67-4) → 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5)

Guidance literature:

L-glycero-3-phosphorylcholine; With di(n-butyl)tin oxide; In methanol; for 1.5h; Heating / reflux;

n-hexadecanoyl chloride; With triethylamine; In WA; at 25 ℃; Product distribution / selectivity;

Reference yield: 98.0%

1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-3-glycerophosphocholine (605680-01-1) → 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1021/jo062352f

upstream raw materials:

hexadecanoic acid, glycidyl ester

choline phosphate

1-palmitoyllysophosphatidylcholine

1-palmitoyl-2-benzylglycerophosphocholine

Downstream raw materials:

10-Nitrooleic Acid

(E)-methyl 10-nitrooctadec-9-enoate

Refernces

• 1、 Guttenberger, Nikolaus,Glabonjat, Ronald A.,Tassoti, Sebastian,Francesconi, Kevin A.. "Synthetic access to arsenic-containing phosphatidylcholines". supporting information. p. 2651 - 2653. Retrieved 2017/06/14.
• 2、 Gliszczyńska, Anna,Niezgoda, Natalia,G?adkowski, Witold,Czarnecka, Marta,?witalska, Marta,Wietrzyk, Joanna. "Synthesis and biological evaluation of novel phosphatidylcholine analogues containing monoterpene acids as potent antiproliferative agents". . . Retrieved 2016/07/06.