Related Experiment Video
Updated: May 1, 2026
Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Preparation of 13 or 9-hydroperoxy-9Z,11E (9E,11E) or 10E,12Z (10E,12E)-octadecadienoic phosphatidylcholine
Shunji Kato1, Kiyotaka Nakagawa, Yuuri Suzuki
1Food and Biodynamic Chemistry Laboratory, Graduate School of Agricultural Science, Tohoku University.
Abstract:
Increasing evidence of phospholipid peroxidation in the pathophysiology of various diseases demonstrates the need for pure phosphatidylcholine hydroperoxide (PCOOH) reference as a standard for quantification, and for biological studies in this field. Our previous study showed the usability of reaction between hydroperoxide and vinyl ether for preparation of PCOOH. However, the reaction has sometimes provided brown byproducts. Here, we report a method to improve reaction conditions, and demonstrate the production of 30 mg of PCOOH (a pure mixture of 13- and 9-hydroperoxyoctadecadienoyl PCOOH isomers) from 100 mg of phosphatidylcholine without byproduct formation. The resultant PCOOH will be useful as a standard for quantification studies, as well as for the evaluation of PCOOH pathogenicity.
More Related Videos
10:31A Liposome Membrane Permeability Assay for Investigating the Effects of Phosphatidylinositol Phosphate Groups on Membranotropic Action of Venom PLA2
Published on: September 26, 2025
12:23Real-time Monitoring of Ligand-receptor Interactions with Fluorescence Resonance Energy Transfer
Published on: August 20, 2012
Related Concept Videos
01:27Synthesis of Phosphatidylcholine in the ER Membrane
The major components of all eukaryotic cell...
03:00Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
01:57Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids