Density functional theory studies on the oleic acid thermal oxidation into volatile compounds

Lin Xiao; Shang Wang; Yi Wang; Binchen Wang; Chaofan Ji; Xinping Lin; Huipeng Liang; Sufang Zhang; Xianbing Xu; Liang Dong

Food Chemistry: X (Oct 2023)

Density functional theory studies on the oleic acid thermal oxidation into volatile compounds

Lin Xiao,
Shang Wang,
Yi Wang,
Binchen Wang,
Chaofan Ji,
Xinping Lin,
Huipeng Liang,
Sufang Zhang,
Xianbing Xu,
Liang Dong

Affiliations

Lin Xiao: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; China Resources Snow Beer, Beijing 100000, Beijing, China
Shang Wang: School of Biotechnology, Dalian Polytechnic University, Dalian 116034, Liaoning, China
Yi Wang: School of Biotechnology, Dalian Polytechnic University, Dalian 116034, Liaoning, China
Binchen Wang: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China
Chaofan Ji: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China
Xinping Lin: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China
Huipeng Liang: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China
Sufang Zhang: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China
Xianbing Xu: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China
Liang Dong: School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China; National Engineering Research Center of Seafood, Dalian 116034, Liaoning, China; Corresponding author at: School of Food Science and Technology, National Engineering Research Center of Seafood, Dalian Polytechnic University, Qinggongyuan Road No.1, Dalian 116034, China.

Journal volume & issue: Vol. 19
p. 100737

Abstract

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Oleic acid oxidation is one of the main sources of food flavor compounds. Volatile profiling was investigated using thermal desorption cryo-trapping combined with gas chromatography–mass spectrometry to analyze the volatile composition of oleic acid oxidation. A total of 43 volatile compounds, including aldehydes (11), ketones (2), alcohols (5), furans (2), acids (8), ester (12) and alkane (3) were identified from oleic acid during heating. Then, density functional theory (DFT) was applied to analyze the oxidative mechanism of oleic acid during heating. A total of 30 reactions were obtained and grouped into the peroxide (ROOH), alkoxy radical (RO•), and peroxide radical (ROO•) pathways. The structures of intermediates, transition states (TS), and products in each reaction were also determined. Results show that the branch chemical reactions were the key reactions in different reaction pathway. Moreover, the reaction priority of the thermal oxidation reaction of oleic acid was the peroxide radical mechanism > the peroxide mechanism > the alkoxy radical mechanism.

Published in Food Chemistry: X

ISSN: 2590-1575 (Online)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Technology: Home economics: Nutrition. Foods and food supply; Technology: Chemical technology: Food processing and manufacture
Website: https://www.journals.elsevier.com/food-chemistry-x

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