A systematic characterization of the reversion flavor of soybean oil
Rent the article at a discountRent now
* Final gross prices may vary according to local VAT.Get Access
The volatile flavor compounds in a reverted soybean oil with a peroxide number of 4.3 meq/kg were isolated by a semicontinuous counter-current vacuum steam-distillation process, fractionated by repeated gas chromatography, and identified by infrared and mass spectrometry. A total of 71 compounds were identified, which included 19 acids, 39 nonacidic compounds, and 13 tentatively identified compounds. The acids consisted of eight normal saturated acids, nine α,β-unsaturated acids, a branch-chain acid, one hydroxy acid, two keto acids, three lactones, and one aromatic acid. The nonacidic compounds consisted of two esters, eight normal saturated aldehydes, two branched-chain aldehydes, five 2-enals, three dienals, eight ketones, eight alcohols, six hydrocarbons, and four aromatic compounds.
The mechanism of formation of the identified compounds indicated that they were mostly primary or secondary autoxidation products of the hydroperoxides of the unsaturated fatty esters. Since many of the identified compounds were produced from oleic and linoleic acids, it is doubtful that linolenic acid was solely responsible for the reversion flavor.
Of the compounds identified two are of unusual interest. They are 1-decyne and 2-pentyl furan. The former is the first acetylenic compound reported as the autoxidation products of unsaturated fatty esters which contained only double bonds. The latter imparts to an oil at concentrations of 5–10 ppm a beany and grassy flavor reminiscent of that of a reverted soybean oil. Since this compound is postulated as being produced by the autoxidation of linolenic acid, it is suggested that the presence of linolenic acid catalyzes the autoxidation of linoleic acid and possibly alters the decomposition pattern of its hydroperoxides.
- Chang, S. S., and J. R. Wilson, Ill. Med. Jour.126, 675–678 (1964).
- Durkee, M. M., Ind. Eng. Chem.28, 898–903 (1936). CrossRef
- Golumbie, C., A. I. Shepartz, and B. F. Daubert, Oil and Soap23, 380–381 (1946). CrossRef
- Dutton, H. J., A. W. Schwab, H. A. Moser and J. C. Cowan, JAOCS26, 441–444 (1949). CrossRef
- Robinson, H. E., and H. C. Black, Ind. Eng. Chem.37, 217–219. (1945). CrossRef
- Bickford, W. G., Oil and Soap18, 95–98 (1941). CrossRef
- Sims, R. J. JAOCS,29, 347–350 (1952). CrossRef
- Lemon, H. W., Can. J. Res.25 F, 34–43 (1947).
- Lips, H. J., H. W. Lemon and G. A. Grant, Can. J. Res.25 F, 44–50 (1947).
- Mattil, K. F., JAOCS24, 243–246 (1947). CrossRef
- Taylor, W. G., JAOCS26, 413–418 (1949). CrossRef
- Hoffmann, R. L., H. A. Moser, C. D. Evans and J. C. Cowan, JAOCS39, 323–327 (1962). CrossRef
- Chang, S. S., and F. A. Kummelow, JAOCS30, 251–254 (1953). CrossRef
- Johnson, O. S., S. S. Chang and F. A. Kummerow, JAOCS30, 317–320 (1953). CrossRef
- Chang, S. S., and F. A. Kummerow, JAOCS31, 324–327 (1954). CrossRef
- Holm, U., K. Ekbom and G. Wode, JAOCS34, 606–610 (1957). CrossRef
- Evans, C. D., E. N. Frankel, P. M. Cooney and H. A. Moser, JAOCS37, 452–456 (1960). CrossRef
- Martin, C., A. I. Schepartz and B. F. Daubert, JAOCS25, 113–117 (1948). CrossRef
- Stapf, R. J. and B. F. Daubert, JAOCS27, 374–377 (1950). CrossRef
- Kawahara, F. K., and H. J. Dutton JAOCS29, 372–377 (1952). CrossRef
- Von Pezold, H., Fette, Seifen, Anstrich,10, 1018–1024 (1959). CrossRef
- Hoffmann, G., JAOCS38, 1–4 (1961). CrossRef
- Ibid.,, JAOCS38, 31–33 (1961).
- Chang, S. S., JAOCS38, 669–671 (1961). CrossRef
- Chang, S. S., K. M. Brobst, H. Tai and C. E. Ireland, JAOCS38, 671–674 (1961). CrossRef
- Mookherjee, B. D. and S. S. Chang, JAOCS40, 232–235 (1963). CrossRef
- Schlenk, H., and J. L. Gellerman, Anal. Chem.32, 1412–1418 (1960). CrossRef
- Smouse, T. H., and S. S. Chang, J. Chromatog.13, 244–246 (1964). CrossRef
- Deck, R. E., J. A. Thompson and S. S. Chang, J. Gas Chromatog. 392–393 (1965).
- Kawada, T., B. D. Mookherjee and S. S. Chang, JAOCS43, 237–241 (1966). CrossRef
- Smouse, T. H., B. D. Mookherjee and S. S. Chang, Ohem. and Ind., 1301–1303 (1965).
- Chang, S. S., T. H. Smouse, R. G. Klishnamurthy, B. D. Mookherjee and B. R. Reddy, Chem. and Ind. 1926–1927 (1966).
- Kawada, T., R. G. Krishnamurthy, B. D. Mookherjee and S. S. Chang, JAOCS44, 131–135 (1967). CrossRef
- Gould, E. S., “Mechanism of Structure in Organic Chemistry,” Holt, Rinehart, and Winston, New York, N.Y., 1959, p. 708.
- Lundberg, W. O., “Autoxidation and Antioxidants,” Vol. 1, Interscience Publishers, Inc., New York, N.Y., 1961, p. 198.
- Mookherjee, B. D., R. E. Deck and S. S. Cyang, Jour. Agr. Food Chem.13, 131–134 (1965). CrossRef
- Silveira, A. Jr., Y. Masuda and S. S. Chang, JAOCS42, 85–86 (1965). CrossRef
- Hoffmann, G., JAOCS39, 439–445 (1962). CrossRef
- Friedman, L. F. and F. A. Long, J. Am. Chem. Soc.75, 2832–2837 (1953). CrossRef
- A systematic characterization of the reversion flavor of soybean oil
Journal of the American Oil Chemists’ Society
Volume 44, Issue 8 , pp 509-514
- Cover Date
- Print ISSN
- Online ISSN
- Additional Links
- Industry Sectors