{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T03:03:03Z","timestamp":1790564583404,"version":"4.1.0"},"reference-count":40,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2021,2,19]],"date-time":"2021-02-19T00:00:00Z","timestamp":1613692800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002347","name":"Bundesministerium f\u00fcr Bildung und Forschung","doi-asserted-by":"publisher","award":["FKZ: 01EA1806"],"award-info":[{"award-number":["FKZ: 01EA1806"]}],"id":[{"id":"10.13039\/501100002347","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Lipid oxidation and the resulting volatile organic compounds are the main reasons for a loss of food quality. In addition to typical compounds, such as alkanes, aldehydes and alcohols, methyl ketones like heptan-2-one, are repeatedly described as aroma-active substances in various foods. However, it is not yet clear from which precursors methyl ketones are formed and what influence amino compounds have on the formation mechanism. In this study, the formation of methyl ketones in selected food-relevant fats and oils, as well as in model systems with linoleic acid or pure secondary degradation products (alka-2,4-dienals, alken-2-als, hexanal, and 2-butyloct-2-enal), has been investigated. Elevated temperatures were chosen for simulating processing conditions such as baking, frying, or deep-frying. Up to seven methyl ketones in milk fat, vegetable oils, and selected model systems have been determined using static headspace gas chromatography-mass spectrometry (GC-MS). This study showed that methyl ketones are tertiary lipid oxidation products, as they are derived from secondary degradation products such as deca-2,4-dienal and oct-2-enal. The study further showed that the position of the double bond in the precursor compound determines the chain length of the methyl ketone and that amino compounds promote the formation of methyl ketones to a different degree. These compounds influence the profile of the products formed. As food naturally contains lipids as well as amino compounds, the proposed pathways are relevant for the formation of aroma-active methyl ketones in food.<\/jats:p>","DOI":"10.3390\/molecules26041104","type":"journal-article","created":{"date-parts":[[2021,2,19]],"date-time":"2021-02-19T20:54:08Z","timestamp":1613768048000},"page":"1104","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":79,"title":["The Formation of Methyl Ketones during Lipid Oxidation at Elevated Temperatures"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6237-8197","authenticated-orcid":false,"given":"Sandra","family":"Grebenteuch","sequence":"first","affiliation":[{"name":"Food Chemistry and Analysis, Technische Universit\u00e4t Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany"},{"name":"Institute for Food and Environmental Research e. V., Papendorfer Weg 3, 14806 Bad Belzig, Germany"},{"name":"NutriAct-Competence Cluster Nutrition Research, c\/o The German Institute of Human Nutrition Potsdam-Rehbr\u00fccke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1461-5386","authenticated-orcid":false,"given":"Clemens","family":"Kanzler","sequence":"additional","affiliation":[{"name":"Food Chemistry and Analysis, Technische Universit\u00e4t Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefan","family":"Klau\u00dfnitzer","sequence":"additional","affiliation":[{"name":"Food Chemistry and Analysis, Technische Universit\u00e4t Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lothar W.","family":"Kroh","sequence":"additional","affiliation":[{"name":"Food Chemistry and Analysis, Technische Universit\u00e4t Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5009-8830","authenticated-orcid":false,"given":"Sascha","family":"Rohn","sequence":"additional","affiliation":[{"name":"Food Chemistry and Analysis, Technische Universit\u00e4t Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany"},{"name":"Institute for Food and Environmental Research e. V., Papendorfer Weg 3, 14806 Bad Belzig, Germany"},{"name":"NutriAct-Competence Cluster Nutrition Research, c\/o The German Institute of Human Nutrition Potsdam-Rehbr\u00fccke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1021\/acs.jafc.9b06258","article-title":"Melanoidins Formed by Heterocyclic Maillard Reaction Intermediates via Aldol Reaction and Michael Addition","volume":"68","author":"Kanzler","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1002\/mnfr.200900608","article-title":"A review on the beneficial aspects of food processing","volume":"54","author":"Fogliano","year":"2010","journal-title":"Mol. Nutr. Food Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"492","DOI":"10.1016\/j.foodchem.2014.05.006","article-title":"Off-flavour masking of secondary lipid oxidation products by pea dextrin","volume":"169","author":"Drusch","year":"2015","journal-title":"Food Chem."},{"key":"ref_4","unstructured":"Decker, E.A. (2010). Understanding and reducing oxidative flavour deterioration in foods. Oxidation in Foods and Beverages and Antioxidant Applications: Woodhead Publishing Series in Food Science, Technology and Nutrition, Woodhead Publishing."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"G\u00f3mez-Cort\u00e9s, P., Sacks, G.L., and Brenna, J.T. (2014). Quantitative analysis of volatiles in edible oils following accelerated oxidation using broad spectrum isotope standards. Food Chem., 310\u2013318.","DOI":"10.1016\/j.foodchem.2014.11.015"},{"key":"ref_6","unstructured":"Erickson, M.D. (2007). Formation and Analysis of Oxidized Monomeric, Dimeric, and Higher Oligomeric Triglycerides. Deep Frying (second edition), AOCS Press."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1007\/BF02536386","article-title":"Autoxidation of polyunsaturated triacylglycerols. IV. Volatile decomposition products from triacylglycerols containing linoleate and linolenate","volume":"27","author":"Frankel","year":"1992","journal-title":"Lipids"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1002\/food.19970410111","article-title":"Precursors of 2-nonenals causing the cardboard off-flavour in butter oil","volume":"41","author":"Widder","year":"1997","journal-title":"Nahrung"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1021\/jf00049a017","article-title":"Quantitative analysis of volatile aldehydes formed from various kinds of fish flesh during heat treatment","volume":"43","author":"Yasuhara","year":"1995","journal-title":"J. Agric. Food Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"671","DOI":"10.1016\/j.foodchem.2012.09.142","article-title":"Shelf-life of infrared dry-roasted almonds","volume":"138","author":"Yang","year":"2013","journal-title":"Food Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1080\/10408390601177613","article-title":"Toxic oxygenated alpha,beta-unsaturated aldehydes and their study in foods: A review","volume":"48","author":"Goicoechea","year":"2008","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1590","DOI":"10.1089\/ars.2011.4406","article-title":"4-Hydroxy-2-Nonenal, a Reactive Product of Lipid Peroxidation, and Neurodegenerative Diseases: A Toxic Combination Illuminated by Redox Proteomics Studies","volume":"17","author":"Perluigi","year":"2011","journal-title":"Antioxid. Redox Signal."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Frankel, E.N. (2012). Chapter 4\u2014Hydroperoxide decomposition. Lipid Oxidation: Oily Press Lipid Library Series, Woodhead Publishing. [2nd ed.].","DOI":"10.1533\/9780857097927.67"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1002\/ffj.1932","article-title":"Aroma-active compounds of Beijing roast duck","volume":"24","author":"Chen","year":"2009","journal-title":"Flavour Fragr. J."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1021\/jf00103a012","article-title":"Isolation and identification of volatile compounds from baked potatoes","volume":"29","author":"Coleman","year":"1981","journal-title":"J. Agric. Food Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1007\/s11746-002-0540-4","article-title":"Evaluation of fat-derived aroma compounds in blue cheese by dynamic headspace GC\/Olfactometry-MS","volume":"79","author":"Qian","year":"2002","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4076","DOI":"10.1007\/s13197-019-03876-6","article-title":"Comprehensive profiling of lipid oxidation volatile compounds during storage of mayonnaise","volume":"56","author":"Calingacion","year":"2019","journal-title":"J. Food Sci. Technol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1111\/j.1745-459X.2004.tb00133.x","article-title":"Sensory characteristics of chemical compounds potentially associated with beany aroma in foods","volume":"19","author":"Chambers","year":"2004","journal-title":"J. Sens. Stud."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/S0308-8146(01)00240-0","article-title":"Interactions between non-volatile water-soluble molecules and aroma compounds in Camembert cheese","volume":"76","author":"Pionnier","year":"2002","journal-title":"Food Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1996","DOI":"10.1021\/jf011094e","article-title":"Characterization of the Most Odor-Active Compounds of Iberian Ham Headspace","volume":"50","author":"Carrapiso","year":"2002","journal-title":"J. Agric. Food Chem."},{"key":"ref_21","first-page":"1026","article-title":"Analysis of Key Odor Compounds in Steamed Chinese Mitten Crab (Eriocheir sinensis)","volume":"941-944","author":"Gu","year":"2014","journal-title":"Adv. Mat. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1094\/CCHEM.2002.79.3.367","article-title":"Differences Between Sensory Profiles and Development of Rancidity During Long-Term Storage of Native and Processed Oat","volume":"79","author":"Lehtinen","year":"2002","journal-title":"Cereal Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/j.foodchem.2008.03.052","article-title":"Formation of oxygenated \u03b1,\u03b2-unsaturated aldehydes and other toxic compounds in sunflower oil oxidation at room temperature in closed receptacles","volume":"111","author":"Guillen","year":"2008","journal-title":"Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1265","DOI":"10.1021\/jf00007a014","article-title":"Headspace volatile compounds formed from heated corn oil and corn oil with glycine","volume":"39","author":"Macku","year":"1991","journal-title":"J. Agric. Food Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1007\/BF02908549","article-title":"A systematic characterization of the reversion flavor of soybean oil","volume":"44","author":"Smouse","year":"1967","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1007\/BF02646284","article-title":"Quantitative studies on methyl ketone formation in butteroil: Effect of temperature","volume":"43","author":"Schwartz","year":"1966","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1291","DOI":"10.3168\/jds.S0022-0302(64)88907-4","article-title":"Development and flavor properties of methyl ketones in milk fat","volume":"47","author":"Langler","year":"1964","journal-title":"J. Dairy Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1007\/BF02633339","article-title":"The effect of heat on pure triglycerides","volume":"39","author":"Crossley","year":"1962","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/S0022-2275(20)40243-3","article-title":"Isolation and characterization of the methyl ketone mecursor in butter fat","volume":"5","author":"Parks","year":"1964","journal-title":"J. Lipid Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1387","DOI":"10.3168\/jds.S0022-0302(65)88472-7","article-title":"Effect of Water on Methyl Ketone Formation in Butteroil","volume":"48","author":"Schwartz","year":"1965","journal-title":"J. Dairy Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/S0022-2275(20)40372-4","article-title":"Precursors of methyl ketones in butter","volume":"4","author":"Begemann","year":"1963","journal-title":"J. Lipid Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"135","DOI":"10.2478\/bvip-2013-0026","article-title":"Fatty Acid Profile of Milk\u2014A Review","volume":"57","year":"2013","journal-title":"Bull. Vet. Inst. Pulawy"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1007\/BF02537398","article-title":"Volatiles from thermal decomposition of isomeric methyl (12S, 13S)-(E)-12,13-epoxy-9-hydroperoxy-10-octadecenoates","volume":"19","author":"Gardner","year":"1984","journal-title":"Lipids"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1002\/jsfa.2740490311","article-title":"Volatile compounds produced in maillard reactions involving cysteine, ribose and phospholipid","volume":"49","author":"Farmer","year":"1989","journal-title":"J. Sci. Food Agric."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3228","DOI":"10.3168\/jds.S0022-0302(91)78509-3","article-title":"The Composition of Milk Fat1","volume":"74","author":"Jensen","year":"1991","journal-title":"J. Dairy Sci."},{"key":"ref_36","unstructured":"U.S. Department of Agricuture (2021, February 18). FoodData Central, Available online: https:\/\/fdc.nal.usda.gov\/."},{"key":"ref_37","first-page":"191","article-title":"Chromatographic analysis of vegetable oils: A review","volume":"4","author":"Aluyor","year":"2009","journal-title":"Sci. Res. Essays"},{"key":"ref_38","unstructured":"Decker, E.A. (2010). 6-Oxidation of edible oils. Oxidation in Foods and Beverages and Antioxidant Applications: Woodhead Publishing Series in Food Science, Technology and Nutrition, Woodhead Publishing."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1016","DOI":"10.1021\/jf00088a044","article-title":"Volatile compounds formed from thermal interaction of 2,4-decadienal with cysteine and glutathione","volume":"37","author":"Zhang","year":"1989","journal-title":"J. Agric. Food Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1002\/food.19870310115","article-title":"Reaction of oxidized lipids with protein Part 14. Aldolization reactions of lower alkanals in presence of nonlipidic substances","volume":"31","author":"Janitz","year":"1987","journal-title":"Nahrung"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/4\/1104\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:26:24Z","timestamp":1760160384000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/4\/1104"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,2,19]]},"references-count":40,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26041104"],"URL":"https:\/\/doi.org\/10.3390\/molecules26041104","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,2,19]]}}}