Abstract
A possible decomposition product of oils containing unsaturated fatty acids with the double bond pattern ω3,6,9 or ω3,6,9, etc., is 2-trans,4-cis,7-cis-decatrienal. It has therefore been investigated whether this trienal is present in strongly autoxidized linolenic acid, soybean, linseed and fish oils. Via a degassing technique the carbonyls from the samples of oils heated in a closed system under nitrogen were collected and separated as their 2,4-dinitrophenylhydrazones (DNPHs) by thin layer chromatography (TLC). The presence of 2-trans,4-cis,7-cis-decatrienal in the samples was positively established by TLC, UV absorption and mass spectroscopy of its DNPH. All analytical data established the complete identity of the isolated DNPH with a synthesized 2,4,7-decatrienal-DNPH. The free aldehyde obtained on hydrolysis of the alkatrienal-DNPH in question had the same flavor as authentic 2-trans,4-cis,7-cis-decatrienal, having a fish or rather a whale oil flavor.
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Presented by J.B.A. Stroink at the ISF Congress, Göteborg, Sweden, June 1972.
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Meijboom, P.W., Stroink, J.B.A. 2-trans,4-cis,7-cis-Decatrienal, the fishy off-flavor occurring in strongly autoxidized oils containing linolenic acid or ω 3,6,9, etc., fatty acids. J Am Oil Chem Soc 49, 555–558 (1972). https://doi.org/10.1007/BF02609225
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DOI: https://doi.org/10.1007/BF02609225