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999989P

Avanti

18:1 Diether PC

powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C44H88NO6P
CAS Number:
105370-99-8
Molecular Weight:
758.15
MDL number:
MFCD28143676
UNSPSC Code:
51191904
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (999989P-10mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 999989P

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

InChI

1S/C44H88NO6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-39-48-42-44(43-51-52(46,47)50-41-38-45(3,4)5)49-40-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,44H,6-19,24-43H2,1-5H3/b22-20-,23-21-/t44-/m1/s1

InChI key

RBPWQIKZHBYIEY-PXCYNBOKSA-N

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 diether PC (phosphocholine)-containing proteoliposomes
  • 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 (999989P-10mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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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