Summary
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1.
The isolation and identification of carbonyl compounds formed by autoxidation of pure ammonium linoleate (0.02 M. in water) has been carried out.
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2.
The autoxidation has been performed according to a method described by Tappel (23). A solution of 0.02 M. ammonium linoleate in 0.1 M. phosphate buffer of pH 6.9, containing 10−4 M. CuSO4, was subjected to autoxidation at 37.2°C.
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3.
The isolation and identification of the D.N.P.-ones of the carbonyl compounds have been carried out, using a method of partition and adsorption chromatography published by van Duin (10, 11).
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4.
It was demonstrated that the principal compounds formed were n-hexanal, 2-octenal, and 2,4-decadienal.
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5.
The formation of these aldehydes is fully in line with the theories of autoxidation of unsaturated fatty acids (1, 3, 13) and of the dismutation of the hydroperoxides formed (2).
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References
Bateman, L., Quart. Revs. (London),8, 147 (1954).
Bell, E. R., Raley, J. H., Rust, F. F., Seubold, F. H., Vaughan, W. E., Disc. Faraday Soc.,10, 242 (1951).
Bolland, L. J., Quart. REvs. (London),3, 1 (1949).
Brekke, J., Mackinney, G., J. Am. Oil Chemists' Soc.,27, 238 (1950).
Braude, F. A., Johnes, E. R. H., J. Chem. Soc. (London), 498 (1945).
Cannon, J. A., Zilch, K. T., Burket, S. C., Dutton, H. J., J. Am. Oil Chemists' Soc.,29, 447 (1952).
Chang, S. S., Kummerow, F. A., J. Am. Oil Chemists' Soc.,30, 251 (1953).
Chang, S. S., Kummerow, F. A., J. Am. Oil Chemists' Soc.,31, 324 (1954).
Coleman, J. E., Knight, H. B., Swern, Daniel, J. Am. Oil Chemists' Soc.,32, 135 (1955).
Duin, H. van, Nature,180, 1473 (1957).
Duin, H. van, Neth. Milk and Dairy J.,12, 74, 81 (1958).
Fritsch, C. W., Deatherage, F. E., J. Am. Oil Chemists' Soc.,33, 109 (1956).
Holman, R. T., “Progress in Chem. Fats Lipids”, vol. II, 51 (1954).
Johnson, O. C., Chang, S. S., and Kummerow, F. A., J. Am. Oil Chemists' Soc.,30, 317 (1953).
Kawahara, F. K., Dutton, H. J., J. Am. Oil Chemists' Soc.,29, 372 (1952).
Kawahara, F. K., Dutton, H. J., Cowan, J. C., J. Am. Oil Chemists' Soc.,29, 633 (1952).
Lea, C. H., Chem. and Ind. (London), 1303 (1953).
Privett, O. S., Lundberg, W. O., Khan, N. A., Tolberg, W. E., Wheeler, D. H., J. Am. Oil Chemists' Soc.,30, 61 (1953).
Schepartz, A. I., Daubert, B. F., J. Am. Oil Chemists' Soc.,27, 367 (1950).
Stapf, R. J., Daubert, B. F., J. Am. Oil Chemists' Soc.,27, 374 (1950).
Swift, C. E., Dollear, F. G., Brown, L. E., and O'Connor, R. T., J. Am. Oil Chemists' Soc.,25, 39 (1948).
Swift, C. E., O'Connor, R. T., Brown, L. E., and Dollear, F. G., J. Am. Oil Chemists' Soc.,26, 297 (1949).
Tappel, A. L., J. Am. Oil Chemists' Soc.,32, 252 (1955).
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Badings, H.T. Isolation and identification of carbonyl compounds formed by autoxidation of ammonium linoleate. J Am Oil Chem Soc 36, 648–650 (1959). https://doi.org/10.1007/BF02640278
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DOI: https://doi.org/10.1007/BF02640278