Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones
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 t...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2024-03-01
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| Series: | Food Chemistry: X |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2590157523005175 |
| _version_ | 1797244935901020160 |
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| author | Kanji Aoyagi Shunji Kato Daisuke Isaka Yoshinori Sekiguchi Yurika Otoki Hidetaka Uehara Kiyotaka Nakagawa |
| author_facet | Kanji Aoyagi Shunji Kato Daisuke Isaka Yoshinori Sekiguchi Yurika Otoki Hidetaka Uehara Kiyotaka Nakagawa |
| author_sort | Kanji Aoyagi |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-08T20:10:23Z |
| format | Article |
| id | doaj.art-b1415326e3034b12b8da36ce658e638d |
| institution | Directory Open Access Journal |
| issn | 2590-1575 |
| language | English |
| last_indexed | 2024-04-24T19:18:55Z |
| publishDate | 2024-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Food Chemistry: X |
| spelling | doaj.art-b1415326e3034b12b8da36ce658e638d2024-03-26T04:27:06ZengElsevierFood Chemistry: X2590-15752024-03-0121101074Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactonesKanji Aoyagi0Shunji Kato1Daisuke Isaka2Yoshinori Sekiguchi3Yurika Otoki4Hidetaka Uehara5Kiyotaka Nakagawa6Laboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, 468-1, Aoba, Aramaki-aza, Aoba-ku, Sendai, Miyagi 980-8572, Japan; Central Research Laboratory, Technical Division, The Nisshin OilliO Group, Ltd., 1 Shinmori-cho, Isogo-ku, Yokohama, Kanagawa 235-8558, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, 468-1, Aoba, Aramaki-aza, Aoba-ku, Sendai, Miyagi 980-8572, JapanCentral Research Laboratory, Technical Division, The Nisshin OilliO Group, Ltd., 1 Shinmori-cho, Isogo-ku, Yokohama, Kanagawa 235-8558, JapanCentral Research Laboratory, Technical Division, The Nisshin OilliO Group, Ltd., 1 Shinmori-cho, Isogo-ku, Yokohama, Kanagawa 235-8558, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, 468-1, Aoba, Aramaki-aza, Aoba-ku, Sendai, Miyagi 980-8572, JapanCentral Research Laboratory, Technical Division, The Nisshin OilliO Group, Ltd., 1 Shinmori-cho, Isogo-ku, Yokohama, Kanagawa 235-8558, JapanLaboratory of Food Function Analysis, Graduate School of Agricultural Science, Tohoku University, 468-1, Aoba, Aramaki-aza, Aoba-ku, Sendai, Miyagi 980-8572, Japan; Corresponding author.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.http://www.sciencedirect.com/science/article/pii/S2590157523005175Saturated fatty acidsThermal oxidationHydroperoxide isomers2-AlkanonesLactones |
| spellingShingle | Kanji Aoyagi Shunji Kato Daisuke Isaka Yoshinori Sekiguchi Yurika Otoki Hidetaka Uehara Kiyotaka Nakagawa Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones Food Chemistry: X Saturated fatty acids Thermal oxidation Hydroperoxide isomers 2-Alkanones Lactones |
| title | Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones |
| title_full | Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones |
| title_fullStr | Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones |
| title_full_unstemmed | Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones |
| title_short | Preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products – 2-alkanones and lactones |
| title_sort | preparation of saturated fatty acid hydroperoxide isomers and determination of their thermal decomposition products 2 alkanones and lactones |
| topic | Saturated fatty acids Thermal oxidation Hydroperoxide isomers 2-Alkanones Lactones |
| url | http://www.sciencedirect.com/science/article/pii/S2590157523005175 |
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