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6-Hydroxychroman-2-carboxylic acids: Novel antioxidants

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Abstract

6-Hydroxychroman-2-carboxylic acids (I) have been found to be effective antioxidants in animal fats, vegetable oils, and emulsion systems. Two new

syntheses of these compounds have been developed. Structure-activity correlations for I with various substitutents at C2, C5, C7, and C8 in various test systems have been obtained. In addition, the homologous chroman acetic acids, which are also antioxidants, and a number of other derived compounds have been synthesized. The most effective antioxidant in this series is the tetramethyl compound I (R2=R5=R7=R8=CH3). This compound has activity which compares well with the better commercial antioxidants.

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References

  1. Bauernfeind, J.C., and W.M. Cort, “Encyclopedia of Food Technology,” Avi Publishing, Westport, Conn., In press.

  2. Lundberg, W.O., Editor, “Autoxidation and Antioxidants,” Vol. II, Interscience, New York, N.Y., 1962, pp. 469–70, 489–90.

    Google Scholar 

  3. Skinner, W.A., H.L. Johnson, M. Ellis, and R.M. Parkhurst, J. Pharm. Sci. 60:643 (1971).

    Article  PubMed  CAS  Google Scholar 

  4. Skinner, W.A., and R.M. Parkhurst, Lipids 5:184 (1970).

    Article  PubMed  CAS  Google Scholar 

  5. Thompson, J.W., and E.R. Sherwin, JAOCS 43:684 (1966).

    Google Scholar 

  6. John, W., and M. Schmeil, Chem. Ber. 72:1653 (1939).

    Google Scholar 

  7. Mayer, H., P. Schudel, R. Rüegg, and O. Isler, Helv. Chim. Acta 46:650 (1963).

    Article  CAS  Google Scholar 

  8. Cort, W.M., J. Food Tech., In press.

  9. Association of Official Analytical Chemists, “Official Methods of Analysis of AOAC,” Association of Official Analytical Chemists, Washington, D.C., 1970, pp. 445–446.

    Google Scholar 

  10. Brown, R.E., D.M. Lustgarten, R.J. Stanaback, and R.I. Meltzer, J. Org. Chem. 31:1489 (1966).

    PubMed  CAS  Google Scholar 

  11. Cort, W.M., JAOCS, In press.

  12. Schudel, P., H. Mayer, J. Metzger, R. Rüegg, and O. Isler, Helv. Chim. Acta 46:636 (1963).

    Article  CAS  Google Scholar 

  13. Eisai Co., Ltd., Jap. Pat. 72 09, 582 (1972).

  14. Corey, E.J., S. Barcza, and G. Klotmann, J. Amer. Chem. Soc. 91:4782 (1969).

    Article  CAS  Google Scholar 

  15. Jacob, A., M. Steiger, A.R. Todd, and T.S. Work, J. Chem. Soc. 542 (1939).

  16. Dolby, L.J., C.A. Elliger, S. Esfandiari, and K.S. Marshall, J. Org. Chem. 33:4508 (1968).

    Article  Google Scholar 

Download references

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Scott, J.W., Cort, W.M., Harley, H. et al. 6-Hydroxychroman-2-carboxylic acids: Novel antioxidants. J Am Oil Chem Soc 51, 200–203 (1974). https://doi.org/10.1007/BF02632894

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  • DOI: https://doi.org/10.1007/BF02632894

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