17364-16-8

Basic information

• Product Name: 1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: P-LYSO-PC;3-SN-LYSOPHOSPHATIDYLCHOLINE, 1-PALMITOYL;1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE;1-PALMITOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE;1-PALMITOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHOCHOLINE;1-PALMITOYL-2-LYSO-SN-GLYCERO-3-PHOSPHOCHOLINE;1-HEXADECANOYL-SN-GLYCEROL-3-PHOSPHORYLCHOLINE;16:0 LYSO PC
• CAS NO: 17364-16-8
• Molecular Formula: C₂₄H₅₀NO₇P
• Molecular Weight: 495.63
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 17364-16-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 253 °C
• Appearance: /
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• BRN: 5385682
• CAS DataBase Reference: 1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(17364-16-8)
• EPA Substance Registry System: 1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(17364-16-8)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 17364-16-8(Hazardous Substances Data)

Usage

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.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 17364-16-8 differently. You can refer to the following data:
1. A lipid biomarker for stable and unstable heart disease.
2. 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.

Biochem/physiol Actions

1-Palmitoyl-sn-glycero-3-phosphocholine may be used as a substrate to identify, differentiate and characterize lysophosphocholine acyl transferases.

InChI:InChI=1/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1

Upstream product

• 14912-92-6 caesium palmitate 
• 6753-55-5 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine 
• 17364-18-0 1-palmitoyllysophosphatidylcholine 
• 7501-44-2 hexadecanoic acid, glycidyl ester 
• 645-84-1 choline phosphate 
• 28319-77-9 L-α-glycerophosphorylcholine 
• 623-65-4 palmitic anhydride 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 525-66-6 propranolol 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 112-67-4 n-hexadecanoyl chloride 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 6931-84-6 lecithin 
• 408-35-5 sodium palmitate 

Downstream Products

• 1039749-81-9 C₅₅H₈₆NO₈PS 
• 875685-46-4 10-Nitrooleic Acid 
• 294659-11-3 (E)-methyl 10-nitrooctadec-9-enoate 
• 117205-52-4 1-hexadecanoyl-2-(9-carboxynonanoyl)glycerophosphocholine 
• 6931-84-6 lecithin 
• 57-10-3 1-hexadecylcarboxylic acid 
• 1372802-60-2 C₇₉H₁₄₃F₄N₅O₁₆P₂S₂ 
• 1315501-24-6 C₃₉H₆₅F₄N₄O₉P 
• 116405-87-9 1-palmitoyl-2-<12-(lipoyloxy)dodecanoyl>-sn-glycero-3-phosphocholine 
• 865302-38-1 C₆₀H₉₆NO₁₁PSi 

Relevant articles and documents

Lytic reactions of drugs with lipid membranes

Propranolol is shown to undergo lipidation reactions in three types of lipid membrane: (1) synthetic single-component glycerophospholipid liposomes; (2) liposomes formed from complex lipid mixtures extracted from E. coli or liver cells; and (3) in cellulo in Hep G2 cells. Fourteen different lipidated propranolol homologues were identified in extracts from Hep G2 cells cultured in a medium supplemented with propranolol. This isolation of lipidated drug molecules from liver cells demonstrates a new drug reactivity in living systems. Acyl transfer from lipids to the alcoholic group of propranolol was favoured over transfer to the secondary amine. Migration of acyl groups from the alcohol to the amine was diminished. Other drugs that were examined did not form detectable levels of lipidation products, but many of these drugs did affect the lysolipid levels in model membranes. The propensity for a compound to induce lysolipid formation in a model system was found to be a predictor for phospholipidosis activity in cellulo.

Synthetic access to arsenic-containing phosphatidylcholines

We wish to disclose the first synthesis of 1-O-hexadecanoyl-2-O-((15-(dimethylarsinoyl)pentadecanoyl)oxy)-sn-glycero-3-phosphocholine, which belongs to the group of arsenic-containing phosphatidylcholines (AsPCs), recently discovered in herring caviar. The synthesized product will serve as a model compound to study biological and toxicological properties of arsenolipids in food.

Peptidophospholipids: Synthesis, phospholipase A2 catalyzed hydrolysis, and application to development of phospholipid prodrugs

New phospholipid analogues incorporating sn-2-peptide substituents have been prepared to probe the fundamental structural requirements for phospholipase A2 catalyzed hydrolysis of PLA2-directed synthetic substrates. Two structurally