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Synthesis and Properties of Alkyl Glycoside and Stachyose Fatty Acid Polyesters

Abstract

A solvent-free interesterification procedure was used to synthesize alkyl giycoside fatty acid polyesters: methyl glucoside polyesters, methyl galactoside polyesters, octyl glucoside polyesters, and tetrasaccharide fatty acid polyester, stachyose polyester. To obtain high yields, the hydroxyl groups on alkyl glycosides and stachyose were first protected by acetylation, and thereafter interesterified with fatty acid methyl esters (FAME) of long chain fatty acids to yield saccharide polyesters. Spectral analysis indicated excellent substitution of fatty acids onto the saccharide moiety. Quantitative C-13 NMR spectroscopic data calculation of the degree of substitution on the saccharide acetates and the saccharide fatty acid polyesters were obtained using chromium acetyl acetonate. Studies of the physical properties of the polyesters indicated that the alkyl glycosides and stachyose polyesters were not markedly different from sucrose polyesters (SPE) or triglycerides.In vitro lipolysis indicated no evidence of hydrolysis, suggesting potential use of alkyl giycoside and stachyose fatty acid polyesters as low calorie oils.

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References

  1. 1.

    Akoh, C.C., and B.G. Swanson,J. Am. Oil Chem. Soc. In press.

  2. 2.

    Akoh, C.C., and B.G. Swanson,J. Food Sci. 52:1570.

  3. 3.

    Akoh, C.C., Ph.D. thesis, Washington State University, Pullman (1988).

  4. 4.

    Mieth, G., A. Eisner and A. Weiss,Die Nahrung 27:147 (1983).

  5. 5.

    Linstead, R.P., A. Rutenberg, W.G. Dauben and W.L. Evans,J. Am. Oil Chem. Soc. 62:3260 (1940).

  6. 6.

    Roseveaar, P., T. VanAken, J. Baxter and S. Ferguson-Miller,Biochemistry 19:4108 (1980).

  7. 7.

    Gibbons, J.P., and C.J. Swanson,J. Am. Oil Chem. Soc. 36:553 (1959).

  8. 8.

    Albano-Garcia, E., R.G. Lorica, M. Pama and L. de Leon,Philipp. J. Coconut Stud. 5:51 (1980).

  9. 9.

    Myhre, D.V., U.S. Patent 3, 597, 417 (1971).

  10. 10.

    Birch, C.G., and F.E. Crowe,J. Am. Oil Chem. Soc. 53:581 (1976).

  11. 11.

    Hamm, D.J.,J. Food Sci. 49:419 (1984).

  12. 12.

    Akoh, C.C., and B.G. Swanson,J. Food Proc. Pres. 12:139 (1988).

  13. 13.

    Weiss, T.J., M. Brown, H.J. Zeringue and R.O. Feuge,J. Am. Oil Chem. Soc. 48:145 (1971).

  14. 14.

    Jandacek, R.J., and M.R. Webb,Chem. Phys. Lipids 22:163 (1978).

  15. 15.

    Akoh, C.C., and B.G. Swanson,Nutrition Rept. International. 39:659 (1989).

  16. 16.

    Pfeffer, P.E., F.E. Luddy, J. Unruh and J.M. Schoolery,J. Am. Oil Chem. Soc. 54:380 (1977).

  17. 17.

    Wehrli, F.W., and T. Wirthlin,Interpretation of C-13 NMR Spectra, Heyden and Sons Inc., New York, NY, 1976.

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Author information

Correspondence to Casimir C. Akoh.

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Akoh, C.C., Swanson, B.G. Synthesis and Properties of Alkyl Glycoside and Stachyose Fatty Acid Polyesters. J Am Oil Chem Soc 66, 1295–1301 (1989). https://doi.org/10.1007/BF03022749

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Keywords

  • Glucoside
  • Apparent Viscosity
  • Methyl Oleate
  • Octyl
  • Thin Layer Chromatography Plate