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Enzymatic interesterification of triolein and tristearin: Chemical structure and differential scanning calorimetric analysis of the products

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Journal of the American Oil Chemists' Society

Abstract

The structural composition and thermal properties of the products of enzymatic interesterification of triolein and tristearin were investigated. The biocatalyst for the reaction was an immobilized Candida antarctica lipase, SP435. Enzyme load of 10% (w/w reactants) produced 72% of desired total products. Oleoyl-distearoyl triglycerides (SSO, OSS) had higher melting points than dioleoyl-stearoyl triglycerides (OOS, SOO) because the sample contained larger amounts of stearic acid than oleic acid residues. SOS and OSO were hardly produced (0.2 to 1.2%), which indicates that SP435 acted as a nonspecific lipase when catalyzing the interesterification of triolein and tristearin. The maximal yield of OSS and SSO (46.9%) was achieved with a 1.2 mole ratio of triolein to tristearin. As the proportion of tristearin was increased, the production of SOO and OOS decreased, the melting profile of the interesterified triglycerides shifted toward higher melting forms, and the solid fat content increased, indicating formation of hard fats.

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References

  1. Cho, S.W., and J.S. Rhee, Immobilization of Lipase for Effective Interesterification of Fats and Oils in Organic Solvent, Biotechnol. Bioeng. 41:204–210 (1993).

    Article  CAS  Google Scholar 

  2. DeMan, J.M., Fats and Oils: Chemistry, Physics and Applications, in Encyclopedia of Food Science and Technology, edited by Y.H. Hui, Wiley, New York, 1992, pp. 823–824.

    Google Scholar 

  3. Chang, M.K., G. Abraham, and V.T. John. Production of Cocoa Butter-Like Fat from Interesterification of Vegetable Oils. J. Am. Oil Chem. Soc. 67:832–834 (1990).

    Article  CAS  Google Scholar 

  4. Busfield, W.K., and P.N. Proschogo, Thermal Analysis of Palm Stearin by DSC, Ibid.:171–175 (1990).

    Article  CAS  Google Scholar 

  5. Birker, P.J.M.W.L., and F.B. Padley, Physical Properties of Fat and Oils, in Recent Advances in Chemistry and Technology of Fats and Oils, edited by R.J. Hamilton and A. Bhati, Elsevier Applied Science, New York, 1987, p. 2.

    Google Scholar 

  6. Garti, N., J. Schlichter, and S. Sarig, DSC Studies Concerning Polymorphism of Saturated Monoacid Triglycerides in the Presence of Food Emulsifiers, Fat Sci Technol. 8:295–299 (1988).

    Google Scholar 

  7. DeMan, J.M., and S. Gupta, Viscoelastic Properties of Plastic Fat Products, J. Am. Oil Chem. Soc. 62:1672–1675 (1985).

    Article  Google Scholar 

  8. Akoh, C.C., B.H. Jennings, and D.A. Lillard, Enzymatic Modification of Evening Primrose Oil: Incorporation of n-3 Polyunsaturated Fatty Acids, Ibid.:1059–1062 (1996).

    Article  CAS  Google Scholar 

  9. Huang, K.H., and C.C. Akoh, Optimization and Scale-Up of Enzymatic Synthesis of Structured Lipid Using RSM, J. Agric. Food Sci. 61:137–141 (1996).

    CAS  Google Scholar 

  10. Huang, K.H., and C.C. Akoh, Lipase-Catalyzed Incorporation of n-3 Polyunsaturated Fatty Acids into Vegetable Oils, J. Am. Oil Chem. Soc. 71:1277–1280 (1996).

    Article  Google Scholar 

  11. Huang, K.H., and C.C. Akoh, Enzymatic Synthesis of Structured Lipids: Transesterification of Triolein and Caprylic Acid Ethyl Ester, Ibid.:245–250 (1994).

    Article  Google Scholar 

  12. Huang, K.H., C.C. Akoh, and M.C. Erickson, Enzymatic Modification of Melon Seed Oil: Incorporation of Eicosapentaenoic Acid, J. Agric. Food. Sci. 42:2646–2648 (1994).

    Article  CAS  Google Scholar 

  13. Luddy, F.E., R.A. Barford, S.F. Herb, P. Magidman, and R.W. Riemenschneider, Pancreatic Lipase Hydrolysis of Triglycerides by a Semimicro Technique, J. Am. Oil Chem. Soc. 41:693–696 (1963).

    Google Scholar 

  14. Official Methods and Recommended Practices of the American Oil Chemists’ Society, 3rd edn., edited by D. Firestone, American Oil Chemists’ Society, Champaign, 1988, Cj 1–94.

    Google Scholar 

  15. Sreenivasan, B., Interesterification of Fats, J. Am. Oil Chem. Soc. 55:796–805 (1978).

    CAS  Google Scholar 

  16. Book Pricing, Novo Nordisk Biochem North America Inc., Franklinton, NC, 1997.

  17. Walker, W.W., Aging of Tristearin: Comparison of DSC and Positron Lifetime Results, J. Am. Oil Chem. Soc. 64:754–756 (1987).

    Article  CAS  Google Scholar 

  18. Lovegreen, N.V., and M.S. Gray, Polymorphism of Saturated Triglycerides: I. 1,3-Distearoyl Triglycerides, Ibid.:311–316 (1978).

    Google Scholar 

  19. Product Information, Novo Nordisk Biochem North America Inc., B 665a-GB 200, Franklinton, NC, 1992.

  20. Hagemann, J.W., and W.H. Tallent, Differential Scanning Calorimetry of Single Acid Triglycerides: Effect of Chain Length and Unsaturation, J. Am. Oil Chem. Soc. 49:119–123 (1972).

    Article  Google Scholar 

  21. Wada, S., and C. Koizumi, Influence of the Position of Unsaturated Fatty Acid Esterified Glycerol on the Oxidation Rate of Triglyceride, Ibid.:1105–1109 (1983).

    CAS  Google Scholar 

  22. Bornaz, S., J. Fanni, and M. Parmentier, Limit of Solid Fat Content Modification of Butter, Ibid.:1373–1380 (1994).

    Article  CAS  Google Scholar 

  23. 7 Series/Unix DSC7 Uses Manual, Software Version 4.0, Perkin Elmer Corporation, Norwalk, CT. 1995.

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Correspondence to Casimir C. Akoh.

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Seriburi, V., Akoh, C.C. Enzymatic interesterification of triolein and tristearin: Chemical structure and differential scanning calorimetric analysis of the products. J Amer Oil Chem Soc 75, 711–716 (1998). https://doi.org/10.1007/s11746-998-0210-9

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  • DOI: https://doi.org/10.1007/s11746-998-0210-9

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