caa a22 4500 60551321X CHVBK 20210128100659.0 cr unu---uuuuu 210128e20150501xx s 000 0 eng 10.1007/s00894-015-2652-y doi (NATIONALLICENCE)springer-10.1007/s00894-015-2652-y Quantum chemical study of the isomerization of 24-methylenecycloartanol, a potential marker of olive oil refining [Elektronische Daten] [Henry Wedler, Ryan Pemberton, Valère Lounnas, Gert Vriend, Dean Tantillo, Selina Wang] 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. Springer-Verlag Berlin Heidelberg, 2015 Olive oil nationallicence Carbocation nationallicence Quantum chemistry nationallicence Mechanism nationallicence Wedler Henry Department of Chemistry, University of California-Davis, 95616, Davis, CA, USA aut Pemberton Ryan Department of Chemistry, University of California-Davis, 95616, Davis, CA, USA aut Lounnas Valère CMBI Radboudumc, Geert Grooteplein 26-28, 6525 GA, Nijmegen, The Netherlands aut Vriend Gert CMBI Radboudumc, Geert Grooteplein 26-28, 6525 GA, Nijmegen, The Netherlands aut Tantillo Dean Department of Chemistry, University of California-Davis, 95616, Davis, CA, USA aut Wang Selina UC Davis Olive Center, University of California-Davis, 95616, Davis, CA, USA aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-4 1610-2940 21:5<1 2015 21 894 https://doi.org/10.1007/s00894-015-2652-y text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2652-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Wedler Henry Department of Chemistry, University of California-Davis, 95616, Davis, CA, USA aut NATIONALLICENCE 700 1- Pemberton Ryan Department of Chemistry, University of California-Davis, 95616, Davis, CA, USA aut NATIONALLICENCE 700 1- Lounnas Valère CMBI Radboudumc, Geert Grooteplein 26-28, 6525 GA, Nijmegen, The Netherlands aut NATIONALLICENCE 700 1- Vriend Gert CMBI Radboudumc, Geert Grooteplein 26-28, 6525 GA, Nijmegen, The Netherlands aut NATIONALLICENCE 700 1- Tantillo Dean Department of Chemistry, University of California-Davis, 95616, Davis, CA, USA aut NATIONALLICENCE 700 1- Wang Selina UC Davis Olive Center, University of California-Davis, 95616, Davis, CA, USA aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-4 1610-2940 21:5<1 2015 21 894