Formation of Secondary and Tertiary Volatile Compounds Resulting from the Lipid Oxidation of Rapeseed Oil

The lipid oxidation of fats and oils leads to volatile organic compounds, having a decisive influence on the sensory quality of foods. To understand formation and degradation pathways and to evaluate the suitability of lipid-derived aldehydes as marker substances for the oxidative status of foods, t...

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Published inFoods Vol. 10; no. 10; p. 2417
Main Authors Grebenteuch, Sandra, Kroh, Lothar W., Drusch, Stephan, Rohn, Sascha
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 12.10.2021
MDPI
Subjects
2-butyl-2-octenal
Adducts
Aldehydes
Automation
Brassica napus
Chemicals
Chromatography
Cold
Condensates
Condensation products
condensation reactions
Degradation
Degradation products
Experiments
Fatty acids
flavour deterioration
Food
Food quality
Food science
Furans
Gas chromatography
Hexanal
Ketones
Lipid peroxidation
lipid-derived aldehydes
Lipids
Markers
Mass spectrometry
Organic compounds
Oxidation
Pesticides
Phospholipids
Potassium
Propionaldehyde
Rapeseed
Rapeseed oil
Scientific imaging
Sensory properties
tertiary products
Vegetable oils
VOCs
Volatile compounds
Volatile organic compounds
Volatility
Germany
Online AccessGet full text
ISSN2304-8158
2304-8158
DOI10.3390/foods10102417

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Abstract The lipid oxidation of fats and oils leads to volatile organic compounds, having a decisive influence on the sensory quality of foods. To understand formation and degradation pathways and to evaluate the suitability of lipid-derived aldehydes as marker substances for the oxidative status of foods, the formation of secondary and tertiary lipid oxidation compounds was investigated with gas chromatography in rapeseed oils. After 120 min, up to 65 compounds were detected. In addition to secondary degradation products, tertiary products such as alkyl furans, ketones, and aldol condensation products were also found. The comparison of rapeseed oils, differing in their initial peroxide values, showed that the formation rate of secondary compounds was higher in pre-damaged oils. Simultaneously, a faster degradation, especially of unsaturated aldehydes, was observed. Consequently, the formation of tertiary products (e.g., alkyl furans, aldol adducts) from well-known lipid oxidation products (i.e., propanal, hexanal, 2-hexenal, and 2-nonenal) was investigated in model systems. The experiments showed that these compounds form the new substances in subsequent reactions, especially, when other compounds such as phospholipids are present. Hexanal and propanal are suitable as marker compounds in the early phase of lipid oxidation, but at an advanced stage they are subject to aldol condensation. Consequently, the detection of tertiary degradation products needs to be considered in advanced lipid oxidation.
AbstractList The lipid oxidation of fats and oils leads to volatile organic compounds, having a decisive influence on the sensory quality of foods. To understand formation and degradation pathways and to evaluate the suitability of lipid-derived aldehydes as marker substances for the oxidative status of foods, the formation of secondary and tertiary lipid oxidation compounds was investigated with gas chromatography in rapeseed oils. After 120 min, up to 65 compounds were detected. In addition to secondary degradation products, tertiary products such as alkyl furans, ketones, and aldol condensation products were also found. The comparison of rapeseed oils, differing in their initial peroxide values, showed that the formation rate of secondary compounds was higher in pre-damaged oils. Simultaneously, a faster degradation, especially of unsaturated aldehydes, was observed. Consequently, the formation of tertiary products (e.g., alkyl furans, aldol adducts) from well-known lipid oxidation products (i.e., propanal, hexanal, 2-hexenal, and 2-nonenal) was investigated in model systems. The experiments showed that these compounds form the new substances in subsequent reactions, especially, when other compounds such as phospholipids are present. Hexanal and propanal are suitable as marker compounds in the early phase of lipid oxidation, but at an advanced stage they are subject to aldol condensation. Consequently, the detection of tertiary degradation products needs to be considered in advanced lipid oxidation.
The lipid oxidation of fats and oils leads to volatile organic compounds, having a decisive influence on the sensory quality of foods. To understand formation and degradation pathways and to evaluate the suitability of lipid-derived aldehydes as marker substances for the oxidative status of foods, the formation of secondary and tertiary lipid oxidation compounds was investigated with gas chromatography in rapeseed oils. After 120 min, up to 65 compounds were detected. In addition to secondary degradation products, tertiary products such as alkyl furans, ketones, and aldol condensation products were also found. The comparison of rapeseed oils, differing in their initial peroxide values, showed that the formation rate of secondary compounds was higher in pre-damaged oils. Simultaneously, a faster degradation, especially of unsaturated aldehydes, was observed. Consequently, the formation of tertiary products (e.g., alkyl furans, aldol adducts) from well-known lipid oxidation products (i.e., propanal, hexanal, 2-hexenal, and 2-nonenal) was investigated in model systems. The experiments showed that these compounds form the new substances in subsequent reactions, especially, when other compounds such as phospholipids are present. Hexanal and propanal are suitable as marker compounds in the early phase of lipid oxidation, but at an advanced stage they are subject to aldol condensation. Consequently, the detection of tertiary degradation products needs to be considered in advanced lipid oxidation.The lipid oxidation of fats and oils leads to volatile organic compounds, having a decisive influence on the sensory quality of foods. To understand formation and degradation pathways and to evaluate the suitability of lipid-derived aldehydes as marker substances for the oxidative status of foods, the formation of secondary and tertiary lipid oxidation compounds was investigated with gas chromatography in rapeseed oils. After 120 min, up to 65 compounds were detected. In addition to secondary degradation products, tertiary products such as alkyl furans, ketones, and aldol condensation products were also found. The comparison of rapeseed oils, differing in their initial peroxide values, showed that the formation rate of secondary compounds was higher in pre-damaged oils. Simultaneously, a faster degradation, especially of unsaturated aldehydes, was observed. Consequently, the formation of tertiary products (e.g., alkyl furans, aldol adducts) from well-known lipid oxidation products (i.e., propanal, hexanal, 2-hexenal, and 2-nonenal) was investigated in model systems. The experiments showed that these compounds form the new substances in subsequent reactions, especially, when other compounds such as phospholipids are present. Hexanal and propanal are suitable as marker compounds in the early phase of lipid oxidation, but at an advanced stage they are subject to aldol condensation. Consequently, the detection of tertiary degradation products needs to be considered in advanced lipid oxidation.
Author Grebenteuch, Sandra
Drusch, Stephan
Kroh, Lothar W.
Rohn, Sascha
AuthorAffiliation 3 NutriAct-Competence Cluster Nutrition Research, c/o The German Institute of Human Nutrition Potsdam-Rehbrücke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany; stephan.drusch@tu-berlin.de
2 Institute for Food and Environmental Research e. V., Papendorfer Weg 3, 14806 Bad Belzig, Germany
4 Department of Food Technology and Food Material Science, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Königin-Luise-Str. 22, 14195 Berlin, Germany
1 Department of Food Chemistry and Analysis, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany; sandra.grebenteuch@tu-berlin.de (S.G.); lothar.kroh@tu-berlin.de (L.W.K.)
AuthorAffiliation_xml – name: 1 Department of Food Chemistry and Analysis, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Gustav-Meyer-Allee 25, 13355 Berlin, Germany; sandra.grebenteuch@tu-berlin.de (S.G.); lothar.kroh@tu-berlin.de (L.W.K.)
– name: 2 Institute for Food and Environmental Research e. V., Papendorfer Weg 3, 14806 Bad Belzig, Germany
– name: 3 NutriAct-Competence Cluster Nutrition Research, c/o The German Institute of Human Nutrition Potsdam-Rehbrücke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany; stephan.drusch@tu-berlin.de
– name: 4 Department of Food Technology and Food Material Science, Institute of Food Technology and Food Chemistry, Technische Universität Berlin, Königin-Luise-Str. 22, 14195 Berlin, Germany
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  orcidid: 0000-0001-6237-8197
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  orcidid: 0000-0002-5009-8830
  surname: Rohn
  fullname: Rohn, Sascha
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Snippet The lipid oxidation of fats and oils leads to volatile organic compounds, having a decisive influence on the sensory quality of foods. To understand formation...
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StartPage 2417
SubjectTerms 2-butyl-2-octenal
Adducts
Aldehydes
Automation
Brassica napus
Chemicals
Chromatography
Cold
Condensates
Condensation products
condensation reactions
Degradation
Degradation products
Experiments
Fatty acids
flavour deterioration
Food
Food quality
Food science
Furans
Gas chromatography
Hexanal
Ketones
Lipid peroxidation
lipid-derived aldehydes
Lipids
Markers
Mass spectrometry
Organic compounds
Oxidation
Pesticides
Phospholipids
Potassium
Propionaldehyde
Rapeseed
Rapeseed oil
Scientific imaging
Sensory properties
tertiary products
Vegetable oils
VOCs
Volatile compounds
Volatile organic compounds
Volatility
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Title Formation of Secondary and Tertiary Volatile Compounds Resulting from the Lipid Oxidation of Rapeseed Oil
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https://www.proquest.com/docview/2584791726
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https://pubmed.ncbi.nlm.nih.gov/PMC8535505
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