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Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products - 2-alkanones and lactones.

ABSTRACT: As known for quite a long time now, even saturated fatty acids can be oxidized at high temperatures to produce unique aroma compounds, such as 2-alkanones and lactones. Hydroperoxide positional isomers with a hydroperoxy group at the 2-, 3-, 4-, or 5-position are hypothesized to be responsible for the formation of these aroma components, but this hypothesis has not been verified. For the first time, this study successfully prepared a series of glyceryl trioctanoate hydroperoxide (C8TG;OOH) isomers. The isomers were thermally decomposed, proving that 2-heptanone was selectively formed from C8TG;3-OOH, and γ- and δ-octalactones were mainly formed from C8TG;4- and 5-OOH, respectively. C8TG;2-OOH was also involved in lactone formation, whereas C8TG;6- and 7-OOH were not. This proves the long-standing hypothesis. The mechanism revealed in this work is expected to be useful to create favorable aromas (i.e., 2-alkanones and lactones) from saturated fatty acids.

SUBMITTER: Aoyagi K

PROVIDER: S-EPMC10784145 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products - 2-alkanones and lactones.

Aoyagi Kanji K Kato Shunji S Isaka Daisuke D Sekiguchi Yoshinori Y Otoki Yurika Y Uehara Hidetaka H Nakagawa Kiyotaka K

Food chemistry: X 20231218

As known for quite a long time now, even saturated fatty acids can be oxidized at high temperatures to produce unique aroma compounds, such as 2-alkanones and lactones. Hydroperoxide positional isomers with a hydroperoxy group at the 2-, 3-, 4-, or 5-position are hypothesized to be responsible for the formation of these aroma components, but this hypothesis has not been verified. For the first time, this study successfully prepared a series of glyceryl trioctanoate hydroperoxide (C8TG;OOH) isome ...[more]

PMID: 38223526

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Dataset Information

Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products - 2-alkanones and lactones.

Publications

Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products - 2-alkanones and lactones.

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