Mechanism of thermal oxidation into volatile compounds from (E)-4-decenal: A density functional theory study

Binchen Wang; Shaohua Dou; Shang Wang; Yi Wang; Sufang Zhang; Xinping Lin; Yingxi Chen; Chaofan Ji; Yiwei Dai; Liang Dong

doi:10.1016/j.fochx.2024.101174

Mechanism of thermal oxidation into volatile compounds from (E)-4-decenal: A density functional theory study

Food Chem X. 2024 Feb 6:21:101174. doi: 10.1016/j.fochx.2024.101174. eCollection 2024 Mar 30.

Authors

Binchen Wang^{1

2}, Shaohua Dou³, Shang Wang⁴, Yi Wang⁴, Sufang Zhang^{1

2}, Xinping Lin^{1

2}, Yingxi Chen^{1

2}, Chaofan Ji^{1

2}, Yiwei Dai^{1

2}, Liang Dong^{1

2}

Affiliations

¹ School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, Liaoning, China.
² National Engineering Research Centre of Seafood, Dalian 116034, Liaoning, China.
³ College of Life and Health, Dalian University, Dalian 116622, Liaoning, China.
⁴ School of Biotechnology, Dalian Polytechnic University, Dalian 116034, Liaoning, China.

Abstract

Unsaturated aliphatic aldehyde oxidation plays a significant role in the deep oxidation of fatty acids to produce volatile chemicals. Exposing the oxidation process of unsaturated aliphatic aldehydes is crucial to completely comprehend how food flavor forms. In this study, thermal desorption cryo-trapping in conjunction with gas chromatography-mass spectrometry was used to examine the volatile profile of (E)-4-decenal during heating, and 32 volatile compounds in all were detected and identified. Meanwhile, density functional theory (DFT) calculations were used, and 43 reactions were obtained in the 24 pathways, which were summarized into the peroxide reaction mechanism (ROOH), the peroxyl radical reaction mechanism (ROO·) and the alkoxy radical reaction mechanism (RO·). Moreover, the priority of these three oxidative mechanisms was the RO· mechanism > ROOH mechanism > ROO· mechanism. Furthermore, the DFT results and experimental results agreed well, and the oxidative mechanism of (E)-4-decenal was finally illuminated.

Keywords: Flavor; Oxidation mechanism; Theoretical calculation; Unsaturated aldehyde.