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Thin-layer chromatographic separation of some bromo-and hydroxyderivatives of stearic acid

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

Abstract

Addition of polar substituents to unsaturated fatty acids or their methyl esters enhanced the adsorption affinity contributed by each unsaturation site to such an extent that the resulting derivatives could be easily separated by differential adsorption on a silica gel coating. Saturated and unsaturated fatty acids could be separated by thin layer chromatography after either bromination of their methyl esters or oxidation of their mixture into unsaturated esters, monoenoates, dienoates, and trienoates. Furthermore, it was possible to separate the configurational isomers of the hydroxystearic acids derived fromcis andtrans hydroxylation of oleic and linoleic acids.

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References

  1. Moretti, J., and J. Polonovski, Bull. Soc. Chim. de France, 935 (1954).

  2. Howton, D. R., Science121, 704 (1955).

    Article  CAS  Google Scholar 

  3. Ory, R. L., W. G. Bickford, and J. W. Dieckert, Anal. Chem.,31, 1447 (1959).

    Article  CAS  Google Scholar 

  4. Bergström, S., and K. Pääbo, Acta. Chem. Scand.,8, 1486 (1954).

    Article  Google Scholar 

  5. Kaufmann, H. P., and W. H. Nitsch, Fette-Scifen Anstrichmittel,58, 234 (1956).

    Article  CAS  Google Scholar 

  6. Kaufmann, H. P., and T. H. Khoe,Ibid., 64, 81 (1962).

    Article  CAS  Google Scholar 

  7. Griffiths, H. N., and T. P. Hilditch, J. Chem. Soc.,134, 2321 (1932).

    Google Scholar 

  8. Nevenzel, J. C., and D. R. Howton, J. Org. Chem.,22, 319 (1957).

    Article  CAS  Google Scholar 

  9. McCutcheon, J. W., Org. Syntheses Coll. vol. III, p. 526.

  10. McCutcheon, J. W.,Ibid. Org. Syntheses Coll. vol. III, p. 531.

  11. Rollett, A., Z. Physiol. Chem.,62, 422 (1909).

    Google Scholar 

  12. Kass, J. P., and G. O. Burr, J. Am. Chem. Soc.,61, 1062 (1939).

    Article  CAS  Google Scholar 

  13. Swern, D., G. N. Billen, T. W. Findley, and J. T. Scanlan,Ibid, 67, 1786 (1945).

    Article  CAS  Google Scholar 

  14. Lapworth, A., and E. N. Mottram, J. Chem. Soc.,127, 1628 (1925).

    CAS  Google Scholar 

  15. Riemenschneider, R. W., D. H. Wheeler, and C. E. Sando, J. Biol. Chem.,127, 391 (1939).

    CAS  Google Scholar 

  16. McKay, A. F., N. Levitin, and R. N. Jones, J. Am. Chem. Soc.,76, 2383 (1954).

    Article  CAS  Google Scholar 

  17. Savary, P., and P. Desnuelle, Bull. Soc. Chim. de France, 939 (1953).

  18. Stahl, E., Pharmazie,11, 633 (1956).

    CAS  Google Scholar 

  19. Robinson, G. M., and R. Robinson, J. Chem. Soc.,127, 175 (1925).

    CAS  Google Scholar 

  20. Witnauer, L. P., and D. Swern, J. Am. Chem. Soc.,72, 3364 (1950).

    Article  CAS  Google Scholar 

Download references

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Partial support of these studies by Grant No. H-1819 from National Institutes of Health.

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Sgoutas, D., Kummerow, F.A. Thin-layer chromatographic separation of some bromo-and hydroxyderivatives of stearic acid. J Am Oil Chem Soc 40, 138–141 (1963). https://doi.org/10.1007/BF02640720

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  • DOI: https://doi.org/10.1007/BF02640720

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