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. 2019 Mar 11;9:4125. doi: 10.1038/s41598-019-39767-1

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© The Author(s) 2019

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Expanded 2.45–3.65 ppm regions of the 400 MHz ¹H NMR spectra of (a) sunflower and (b) MRAFO oils heated according to a LSSFE at 180 °C for periods of 0–90 min. (samples were collected for ¹H NMR analysis at the 0, 5, 10, 20, 30, 60 and 90 min. time-points). Abbreviations: 1, trans-9,10-epoxystearate-CHOHC- protons (δ = 2.63 ppm); 2, a combination of the -CHOHC- protons of 9,10-epoxy-octadecanoate, 9,10-epoxy-12-octadecenoate (leukotoxin), 12,13-epoxy-9-octadecenoate (isoleukotoxin) and cis-9,10-epoxystearate (δ = 2.86–2.93 ppm), although almost exclusively the latter LOP in spectrum (b); 3, 9,10-12,13-diepoxyoctadecanoate -CHOHC-CH₂-CHOHC- functions (δ = 3.07 ppm); and 4, α-CH₂ group of primary alcohol LOPs (δ = 3.62 ppm).