1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE Chemical Properties

Melting point:

253 °C

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

form 

Solid

color 

White to Off-White

biological source

synthetic

optical activity

Consistent with structure

BRN 

5385682

InChI

InChI=1S/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

InChIKey

ASWBNKHCZGQVJV-HSZRJFAPSA-N

SMILES

O(C(=O)CCCCCCCCCCCCCCC)C[C@H](COP(OCC[N+](C)(C)C)([O-])=O)O

Safety Information

WGK Germany 

3

F 

10-21

HS Code 

2923.20.2000

MSDS

• Language:English Provider:SigmaAldrich

1-PALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE Usage And Synthesis

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 T_reg 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

A lipid biomarker for stable and unstable heart disease.

Uses

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.

Definition

ChEBI: 1-hexadecanoyl-sn-glycero-3-phosphocholine is a lysophosphatidylcholine 16:0 in which a hexadecanoyl (palmitoyl) group is attached to the glycero moiety at position 1. It has a role as a mouse metabolite. It is a lysophosphatidylcholine 16:0 and a 1-O-acyl-sn-glycero-3-phosphocholine.

Biochem/physiol Actions

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

References

[1] JESúS BALSINDE  Edward A D  Michelle V Winstead. Phospholipase A2 regulation of arachidonic acid mobilization[J]. FEBS Letters, 2002, 531 1: Pages 2-6. DOI: 10.1016/s0014-5793(02)03413-0
[2] SHINKYU CHOI. Superoxide generated by lysophosphatidylcholine induces endothelial nitric oxide synthase downregulation in human endothelial cells.[J]. Cellular Physiology and Biochemistry, 2010, 25 2-3: 233-240. DOI: 10.1159/000276557
[3] XIAOFEI QIN  Luosha Z  Chunguang Qiu. Lysophosphatidylcholine perpetuates macrophage polarization toward classically activated phenotype in inflammation[J]. Cellular immunology, 2014, 289 1: Pages 185-190. DOI: 10.1016/j.cellimm.2014.04.010
[4] HITOSHI HASEGAWA . Lysophosphatidylcholine enhances the suppressive function of human naturally occurring regulatory T cells through TGF-β production[J]. Biochemical and biophysical research communications, 2011, 415 3: Pages 526-531. DOI: 10.1016/j.bbrc.2011.10.119
[5] JI-JING YAN. Therapeutic effects of lysophosphatidylcholine in experimental sepsis[J]. Nature Medicine, 2004, 10 2: 161-167. DOI: 10.1038/nm989

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