Preparation of 13 or 9-hydroperoxy-9Z,11E (9E,11E) or 10E,12Z (10E,12E)-octadecadienoic phosphatidylcholine hydroperoxide

J Oleo Sci. 2014;63(5):431-7. doi: 10.5650/jos.ess13225. Epub 2014 Apr 9.

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.

MeSH terms

  • Hydrogen Peroxide / chemistry
  • Organic Chemistry Phenomena
  • Phosphatidylcholines / chemical synthesis*
  • Phosphatidylcholines / chemistry
  • Phosphatidylcholines / standards
  • Reference Standards
  • Vinyl Compounds / chemistry

Substances

  • Phosphatidylcholines
  • Vinyl Compounds
  • phosphatidylcholine hydroperoxide
  • vinyl ether
  • Hydrogen Peroxide