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Retro-aldol degradations of unsaturated aldehydes: Role in the formation ofc4-heptenal fromt2,c6-nonadienal in fish, oyster and other flavors

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Journal of the American Oil Chemists’ Society

Abstract

Alterations of cucumber-, melon-like notes in aromas and flavors caused by retro-aldol degradations oft2,c6-nonadienal were confirmed using gas chromatographic measurements of volatile compounds in model systems. The data indicated that 3-hydroxy-c6-nonenal was formed first by the addition of water to the alpha/beta double bond oft2,c6-nonadienal, and this was followed by a retro-aldol condensation of 3-hydroxy-c6-nonenal to yieldc4-heptenal and ethanal. Compared to the reaction rate in aqueous systems at neutral pH, formation ofc4-heptenal was enhanced substantially at alkaline pH, but was greatly diminished at acidic pH values. Heating (to 90 C) of aqueous model systems oft2,c6-nonadienal held at neutral pH also enhanced the rate of formation ofc4-heptenal substantially compared to that at ambient temperature (21 C). Rates of formation ofc4-heptenal in aqueous model systems held under air or nitrogen atmospheres were similar.c4-Heptenal was not formed whent2,c6-nonadienal was held at 21 C for 96 hr under air or nitrogen in nonaqueous commercial corn oil.

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Authors and Affiliations

  1. Department of Food Science, University of Wisconsin-Madison, 53706, Madison, WI

    David B. Josephson & Robert C. Lindsay

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  1. David B. Josephson
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  2. Robert C. Lindsay
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This paper is based on research supported by the College of Agriculture and Life Sciences and the Sea Grant Program, University of Wisconsin-Madison.

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Josephson, D.B., Lindsay, R.C. Retro-aldol degradations of unsaturated aldehydes: Role in the formation ofc4-heptenal fromt2,c6-nonadienal in fish, oyster and other flavors. J Am Oil Chem Soc 64, 132–138 (1987). https://doi.org/10.1007/BF02546268

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  • DOI: https://doi.org/10.1007/BF02546268

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