1-hexacosanoyl-2-hydroxy-sn-glycero-3-phosphocholine
- Product Name
- 1-hexacosanoyl-2-hydroxy-sn-glycero-3-phosphocholine
- CAS No.
- 1213783-80-2
- Chemical Name
- 1-hexacosanoyl-2-hydroxy-sn-glycero-3-phosphocholine
- Synonyms
- 26:0 Lyso PC;1-Hexacosanoyl-sn-glycero-3-phosphocholine;1-hexacosanoyl-2-hydroxy-sn-glycero-3-phosphocholine;1-HEXACOSANOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHOCHOLINE;26:0 LYSO PC;(R)-3-(hexacosanoyloxy)-2-hydroxypropyl (2-(trimethylammonio)ethyl) phosphate;[(2R)-3-hexacosanoyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
- CBNumber
- CB42719799
- Molecular Formula
- C34H70NO8P
- Formula Weight
- 651.895261
- MOL File
- 1213783-80-2.mol
1-hexacosanoyl-2-hydroxy-sn-glycero-3-phosphocholine Property
- storage temp.
- -20°C
- form
- powder
- Appearance
- white powder
1-hexacosanoyl-2-hydroxy-sn-glycero-3-phosphocholine Chemical Properties,Usage,Production
Description
Lysopc(26:0), also known as LysoPC a C26:0, is classified as a member of the 1-acyl-sn-glycero-3-phosphocholines. 1-acyl-sn-glycero-3-phosphocholines are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Lysopc(26:0) can be used as internal standard LC-MS studies.
Lysophosphatidylcholines (LPCs) specifically bind to G protein-coupled receptors GPR119, GPR40, GPR55 and GPR4. Binding of LPCs to GPR119, GPR40 and GPR55 induces intracellular calcium mobilization and leads to increased glucose-stimulated insulin secretion in different cell systems. In blood or plasma LPCs are bound mainly to albumin and to a lesser extent to lipoproteins.
Inflammation, cell damage and other pathophysiological conditions can profoundly alter the ratio of free to albumin bound LPC through increased production of LPC or decreased plasma levels of albumin. In particular, lower levels of albumin (hypoalbuminemia) lead to lower levels of LPC in the blood. Lysopc(26:0) is a biomarker for X-linked Adrenoleukodystrophy (X-ALD). Lysopc(26:0) could be used as auxiliary marker for diagnosis of peroxisomal β-oxidation disorders.
Uses
26:0 Lyso PC has been used as an internal standard for C26:0-lysophosphatidylcholine (LPC) extraction.
Definition
ChEBI: (2-{[(2R)-3-(hexacosanoyloxy)-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium is a 1-O-acyl-sn-glycero-3-phosphocholine.
Biological Activity
Lysophosphatidylcholine (LPC) induces many second messengers including, protein kinase C, extracellular-signal-regulated kinases and protein tyrosine kinases. It alters various biological functions in different cell types, including endothelial cells, smooth muscle cells, monocytes, macrophages and T-cells. LPC is linked to atherosclerosis and inflammatory diseases.