Quantum chemical study of the isomerization of 24-methylenecycloartanol, a potential marker of olive oil refining

  • Henry B. Wedler
  • Ryan P. Pemberton
  • Valère Lounnas
  • Gert Vriend
  • Dean J. Tantillo
  • Selina C. Wang
Original Paper

Abstract

Quantum chemical calculations on the isomerization of 24-methylenecycloartanol are described. An energetically viable mechanism, with a rate-determining protonation step, is proposed. This rearrangement may find applicability in tests for determining if an olive oil has been refined.

Graphical Abstract

The results of density functional calculations on the mechanism of a rearrangement of a sterol proposed to occur during olive oil heating are described. These results indicate that this rearrangement can indeed occur at a fast rate under refining conditions, but will not occur at an appreciable rate under conditions for producing extra virgin olive oil.

Keywords

Olive oil Carbocation Quantum chemistry Mechanism 

Supplementary material

894_2015_2652_MOESM1_ESM.pdf (3.4 mb)
Supporting InformationAdditional Supporting Information (details on computational approaches, along with coordinates and energies for computed structures and IRC data) may be found in the online version of this article. (PDF 3457 kb)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Henry B. Wedler
    • 1
  • Ryan P. Pemberton
    • 1
  • Valère Lounnas
    • 3
  • Gert Vriend
    • 3
  • Dean J. Tantillo
    • 1
  • Selina C. Wang
    • 2
  1. 1.Department of ChemistryUniversity of California–DavisDavisUSA
  2. 2.UC Davis Olive CenterUniversity of California–DavisDavisUSA
  3. 3.CMBI RadboudumcNijmegenThe Netherlands

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