{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T02:23:48Z","timestamp":1760235828418,"version":"build-2065373602"},"reference-count":16,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2021,9,27]],"date-time":"2021-09-27T00:00:00Z","timestamp":1632700800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Polish Ministry of Science and Higher Education","award":["11\/2020"],"award-info":[{"award-number":["11\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>It was proven that sterols subjected to high-temperature treatment can be concatenated, which results in polymeric structures, e.g., 3\u03b2,3\u2032\u03b2-disteryl ethers. However, it was also proven that due to increased temperature in oxygen-containing conditions, sterols can undergo various oxidation reactions. This study aimed to prove the existence and perform quantitative analysis of oxidized 3\u03b2,3\u2032\u03b2-disteryl ethers, which could form during high-temperature treatment of sterol-rich samples. Samples were heated at 180, 200 and 220 \u00b0C for 0.5 to 4 h. Quantitative analyses of the oxidized 3\u03b2,3\u2032\u03b2-disteryl ethers were performed with liquid extraction, solid-phase extraction and liquid chromatography coupled with mass spectrometry. Additionally, to perform this analysis, the appropriate standards of all oxidized 3\u03b2,3\u2032\u03b2-disteryl ethers were prepared. Eighteen various oxidized 3\u03b2,3\u2032\u03b2-disteryl ethers (derivatives of 3\u03b2,3\u2032\u03b2-dicholesteryl ether, 3\u03b2,3\u2032\u03b2-disitosteryl ether and 3\u03b2,3\u2032\u03b2-distigmasteryl ether) were prepared. Additionally, the influence of metal compounds on the mechanism of ether formation at high temperatures was investigated.<\/jats:p>","DOI":"10.3390\/ijms221910421","type":"journal-article","created":{"date-parts":[[2021,9,27]],"date-time":"2021-09-27T10:39:20Z","timestamp":1632739160000},"page":"10421","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis of Oxidized 3\u03b2,3\u2032\u03b2-Disteryl Ethers and Search after High-Temperature Treatment of Sterol-Rich Samples"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5256-6298","authenticated-orcid":false,"given":"Adam","family":"Zmys\u0142owski","sequence":"first","affiliation":[{"name":"Spectrometric Methods Laboratory, National Medicines Institute, Che\u0142mska 30\/34, 00-725 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9962-6024","authenticated-orcid":false,"given":"Jerzy","family":"Sitkowski","sequence":"additional","affiliation":[{"name":"Falsified Medicines and Medical Devices Department, National Medicines Institute, Che\u0142mska 30\/34, 00-725 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6544-5412","authenticated-orcid":false,"given":"Katarzyna","family":"Bus","sequence":"additional","affiliation":[{"name":"Spectrometric Methods Laboratory, National Medicines Institute, Che\u0142mska 30\/34, 00-725 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7329-3081","authenticated-orcid":false,"given":"Katarzyna","family":"Michalska","sequence":"additional","affiliation":[{"name":"Department of Synthetic Drugs, National Medicines Institute, Che\u0142mska 30\/34, 00-725 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Arkadiusz","family":"Szterk","sequence":"additional","affiliation":[{"name":"Center for Translationale Medicine, University for Life Sciences, Nowoursynowska 100, 02-797 Warsaw, Poland"},{"name":"Transfer of Science Sp. z o.o., Janiszowska 14, 02-264 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1186\/s12944-017-0579-2","article-title":"Current Knowledge on the Mechanism of Atherosclerosis and Pro-Atherosclerotic Properties of Oxysterols","volume":"16","author":"Szterk","year":"2017","journal-title":"Lipids Health Dis."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.cca.2019.01.022","article-title":"Oxysterols as a Biomarker in Diseases","volume":"491","author":"Szterk","year":"2019","journal-title":"Clin. Chim. Acta"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1007\/s00217-010-1335-2","article-title":"Dimer Formation during the Thermo-Oxidation of Stigmasterol","volume":"231","author":"Struijs","year":"2010","journal-title":"Eur. Food Res. Technol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"127132","DOI":"10.1016\/j.foodchem.2020.127132","article-title":"Synthesis and Search for 3\u03b2,3\u2032\u03b2-Disteryl Ethers after High-Temperature Treatment of Sterol-Rich Samples","volume":"329","author":"Sitkowski","year":"2020","journal-title":"Food Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1016\/j.foodchem.2013.11.079","article-title":"Spectroscopic Characterisation of Dimeric Oxidation Products of Phytosterols","volume":"151","author":"Przybylski","year":"2014","journal-title":"Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2000331","DOI":"10.1002\/ejlt.202000331","article-title":"Purification of Commercially Available \u03b2-Sitosterol via Chemical Synthesis","volume":"123","author":"Sitkowski","year":"2021","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/j.foodchem.2014.08.117","article-title":"Cholesterol Transformations during Heat Treatment","volume":"171","author":"Derewiaka","year":"2015","journal-title":"Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1007\/s11746-009-1397-0","article-title":"Products Formed During Thermo-Oxidative Degradation of Phytosterols","volume":"86","author":"Przybylski","year":"2009","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2132","DOI":"10.1002\/pmic.200700111","article-title":"Analysis of Modified Apolipoprotein B-100 Structures Formed in Oxidized Low-Density Lipoprotein Using LC-MS\/MS","volume":"7","author":"Obama","year":"2007","journal-title":"Proteomics"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"320","DOI":"10.1016\/S0022-2275(20)37619-7","article-title":"Free and Esterified Oxysterol: Formation during Copper-Oxidation of Low Density Lipoprotein and Uptake by Macrophages","volume":"37","author":"Brown","year":"1996","journal-title":"J. Lipid Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1849","DOI":"10.1016\/j.clnu.2019.07.026","article-title":"Zinc, Copper, and Oxysterol Levels in Patients with Type 1 and Type 2 Diabetes Mellitus","volume":"39","author":"Samadi","year":"2020","journal-title":"Clin. Nutr."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1600486","DOI":"10.1002\/ejlt.201600486","article-title":"Volatile Markers of Cholesterol Thermal Changes","volume":"119","author":"Derewiaka","year":"2017","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1002\/ejlt.200900069","article-title":"Distribution of Monomeric, Dimeric and Polymeric Products of Stigmasterol during Thermo-Oxidation","volume":"111","author":"Lampi","year":"2009","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_14","first-page":"2431","article-title":"Dry Column Vacuum Chromatography","volume":"2001","author":"Pedersen","year":"2001","journal-title":"Synthesis"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1007\/s11746-002-0444-3","article-title":"Analysis of Free and Esterified Sterols in Vegetable Oils","volume":"79","author":"Verleyen","year":"2002","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5085","DOI":"10.1007\/s00216-018-1164-x","article-title":"Electrochemical Nonenzymatic Sensor for Cholesterol Determination in Food","volume":"410","author":"Derina","year":"2018","journal-title":"Anal. Bioanal. Chem."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/22\/19\/10421\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:05:57Z","timestamp":1760166357000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/22\/19\/10421"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,27]]},"references-count":16,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2021,10]]}},"alternative-id":["ijms221910421"],"URL":"https:\/\/doi.org\/10.3390\/ijms221910421","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2021,9,27]]}}}