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The flavor problem of soybean oil. XIII. Sulfur coordination compounds effective in edible oil stabilization
Author(s) -
Schwab A. W.,
Moser Helen A.,
Gurley Rosemary S.,
Evans C. D.
Publication year - 1953
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02639361
Subject(s) - chemistry , succinic acid , flavor , organic chemistry , soybean oil , sulfur , sulfonic acid , butyric acid , food science
Summary Sulfur compounds of the tridentate class having at least 2 carboxy groups in α or β position to the coordinating atom have been found to be effective in the stabilization of soybean oil. Comparing model compounds with different coordinating atoms, the order of effectiveness appears to be S>N>O. This order of effectiveness follows an order of increasing electronegativity. Carboxymethylmercapto butyric acid, carboxymethylmercapto phenyl propionic acid, the monoethyl ester of carboxymethylmercapto succinic acid, p‐toluene sulfonic acid, α,α’ acid, and sulfur dioxide all improved the oxidative stability but gave undesirable flavors. Thiodiacetic acid, β,β’ acid, carboxymethylmercapto succinic acid, and the monooctadecyl ester of carboxymethylmercapto succinic acid were found to be excellent stabilizers. The first two may be added either on the upgrade or the downgrade of deodorization, but the heat instability of the latter two limits their addition to the downgrade. All these compounds improved the flavor stability as well as the oxidative stability. The monooctadecyl ester has the added advantage in that it is oil soluble.