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Density functional theory studies on the oleic acid thermal oxidation into volatile compounds
Lin Xiao1,2, Shang Wang3, Yi Wang3
1School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China.
Food Chemistry: X
|October 2, 2023
Summary
Oleic acid oxidation generates key food flavor compounds. Density functional theory revealed that peroxide radical mechanisms are the primary pathway in thermal oxidation, followed by peroxide and alkoxy radical mechanisms.
Area of Science:
- Food Chemistry
- Physical Chemistry
- Computational Chemistry
Background:
- Oleic acid oxidation is a significant source of volatile compounds contributing to food flavor.
- Understanding the oxidative mechanisms is crucial for controlling flavor development and preventing off-flavors.
Purpose of the Study:
- To identify volatile compounds produced during oleic acid oxidation.
- To elucidate the underlying oxidative mechanisms using computational methods.
Main Methods:
- Volatile profiling via thermal desorption cryo-trapping and gas chromatography-mass spectrometry (GC-MS).
- Density functional theory (DFT) calculations to analyze reaction pathways and intermediates.
Main Results:
- Identified 43 volatile compounds, including aldehydes, ketones, alcohols, furans, acids, esters, and alkanes.
- Mapped 30 distinct reaction pathways: peroxide (ROOH), alkoxy radical (RO•), and peroxide radical (ROO•).
- Determined the reaction priority: peroxide radical mechanism > peroxide mechanism > alkoxy radical mechanism.
Conclusions:
- Branch chemical reactions are pivotal in oleic acid oxidation pathways.
- The peroxide radical mechanism dominates the thermal oxidation of oleic acid.
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