Oleoscience
Online ISSN : 2187-3461
Print ISSN : 1345-8949
ISSN-L : 1345-8949
The Mechanism of 2-Alkanone and Lactone Formation by Oxidation of Saturated Fatty Acids
Kanji AOYAGIShunji KATODaisuke ISAKAYurika OTOKIHidetaka UEHARAKiyotaka NAKAGAWA
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2025 Volume 25 Issue 8 Pages 319-329

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Abstract

Saturated fatty acids, which do not have double bonds in their alkyl chains, are often vaguely considered to be less susceptible to oxidation than unsaturated fatty acids, which do have double bonds. However, it has been known for more than half a century that even saturated fatty acids can undergo oxidation when exposed to high temperatures, producing characteristic decomposition products such as 2-alkanones and lactones—key contributors for the aroma of animal-derived foods, including dairy products and beef. It was hypothesized that specific hydroperoxide positional isomers of saturated fatty acids were involved in this phenomenon; however, at the time, it was difficult to prepare these isomers using available techniques, and as a result, the mechanism remained unexplained. In this review, we describe the mechanism by which 2-alkanones and lactones are generated through the oxidation of saturated fatty acids, as elucidated using our recently developed techniques for preparing hydroperoxide isomers. Understanding this mechanism is expected to contribute to the development of technology for creating the aroma of animal-derived foods from plant oils rich in saturated fatty acids, thereby enhancing the flavor of plant-based foods and other products.

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© 2025 Japan Oil Chemists' Society
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