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999989C

Avanti

18:1 Diether PC

1,2-di-O-(9Z-octadecenyl)-sn-glycero-3-phosphocholine, chloroform

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Synonym(s):
Dioctadecenyl PC
Empirical Formula (Hill Notation):
C44H88NO6P
CAS Number:
105370-99-8
Molecular Weight:
758.15
UNSPSC Code:
51191904
NACRES:
NA.25

form

liquid

packaging

pkg of 1 × 1 mL (999989C-10mg)

manufacturer/tradename

Avanti Polar Lipids 999989C

concentration

10 mg/mL (999989C-10mg)

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OCCCCCCCC/C=C\CCCCCCCC)COCCCCCCCC/C=C\CCCCCCCC)=O

General description

18:1 Diether PC (phosphocholine) is a class of glycerophospholipids that has two octadecene chains attached to the sn-1 and sn-2 positions of the glycerol backbone by ether bonds. It has choline as the alcohol moiety, attached to the phosphate group.

Application

18:1 Diether PC or 1,2-di-O-(9Z-octadecenyl)-sn-glycero-3-phosphocholine might be used:
  • to prepare proteoliposomes to investigate the effects of ceramide and ceramide phosphate/ for the determination of phospholipase A activity of lecithin-cholesterol acyltransferase (LCAT) in the ether matrix
  • to prepare lipid bilayer membrane to study the influence of glutamic acid residues and pH on the properties of transmembrane helices
  • in large unilamellar vesicles (LUVs) to explore the differential interaction of pH (low) insertion peptide (pHLIP) with it by utilizing fluorescence and circular dichroism (CD) spectroscopic approaches

Biochem/physiol Actions

Lipids prepared using 18:1 Diether PC (phosphocholine), are found to be more stable than the natural ester lipids under alkaline conditions.

Packaging

5 mL Clear Glass Sealed Ampule (999989C-10mg)

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

Target Organs

Central nervous system, Liver,Kidney

WGK

WGK 3

Regulatory Information

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Venkatesan Rajagopalan et al.
Biochimica et biophysica acta. Biomembranes, 1859(3), 484-492 (2017-01-11)
Negatively charged side chains are important for the function of particular ion channels and certain other membrane proteins. To investigate the influence of single glutamic acid side chains on helices that span lipid-bilayer membranes, we have employed GWALP23 (acetyl-GGALW5LALALALALALALW19LAGA-amide) as
Papasani V Subbaiah et al.
Biochemistry, 45(15), 5029-5038 (2006-04-12)
Sphingomyelin (SM), the second most abundant phospholipid in plasma lipoproteins, was previously shown to be a physiological inhibitor of the lecithin-cholesterol acyltransferase (LCAT) reaction. In this study, we investigated the effects of its metabolites, ceramide and ceramide phosphate, on the
Bhagyashree D Rao et al.
Chemistry and physics of lipids, 226, 104849-104849 (2019-12-15)
pH (low) insertion peptide (pHLIP) is a polypeptide from the third transmembrane helix of bacteriorhodopsin. The pH-dependent membrane insertion of pHLIP has been conveniently exploited for translocation of cargo molecules and as a novel imaging agent in cancer biology due
John M Dean et al.
Protein & cell, 9(2), 196-206 (2017-05-20)
Ether lipids, such as plasmalogens, are peroxisome-derived glycerophospholipids in which the hydrocarbon chain at the sn-1 position of the glycerol backbone is attached by an ether bond, as opposed to an ester bond in the more common diacyl phospholipids. This

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