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Oxidative stability and nuclear magnetic resonance analyses of linoleic acid encapsulated in cyclodextrins

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Journal of the American Oil Chemists' Society

Abstract

The effects of α- and β-cyclodextrin (CD) on the oxidative stability of linoleic acid (LA) at 35°C were studied by measuring headspace oxygen depletion in airtight 35-mL serum bottles. LA was encapsulated in α-CD or β-CD in an aqueous solution during homogenization at 8000 rpm for 1 min and then dried under vacuum for 60 h at room temperature. Headspace oxygen was measured by thermal conductivity gas chromatography. The rate of oxygen depletion for the control, which contained LA only, was 93.8 µmole/L·h. The rates of oxygen depletion for LA, encapsulated at a 1:1 mole ratio (mole CD/moles LA) in α-CD and β-CD, were 13.8 and 111 µmoles/L·h, respectively. When LA was encapsulated in α-CD and β-CD at a 2:1 mole ratio (moles CD/moles LA), the rates of oxygen depletion were 0.573 and 53.9 µmoles/L·h, respectively. Although α-CD protected LA from reaction with oxygen at both ratios, the rate of oxygen depletion by LA encapsulated in β-CD at a 1:1 mole ratio was not statistically different from the control. β-CD protected LA from reaction with oxygen at a 2:1 mole ratio. 1H nuclear magnetic resonance spectra of the complexes formed from 1:1 mole ratios of LA and CD indicated that LA was encapsulated in α-CD or β-CD.

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References

  1. Saenger, W., Structural Aspects of Cyclodextrins and Their Inclusion Complexes, in Inclusion Compounds, edited by J.L. Atwood, J.E. Davies, and D.D. MacNicol, Academic Press, London, 1984, Vol. 2, pp. 231–259.

    Google Scholar 

  2. Divakar, S.J., Structures of a β-Cyclodextrin-Vanillin Inclusion Complex, J. Agric. Food Chem. 38:940–944 (1990).

    Article  CAS  Google Scholar 

  3. Hedges, A.R., W.J. Shieh, and C.T. Sikorski, Use of Cyclodextrins for Encapsulation in the Use and Treatment of Food Products, in Encapsulation and Controlled Release of Food Ingredients, ACS Symposium Series, Vol. 590, 1995, pp. 60–71.

  4. Ishiguro, T., S. Adachi, and R. Matsuno, Thermographic Analysis of Cyclodextrin-Fatty Acid Complex Formation and Its Use for Predicting Suppressed Autoxidation of Fatty Acids, Biosci. Biotechnol. Biochem. 59:51–54 (1995).

    CAS  Google Scholar 

  5. Szente, L., J. Szejtli, J. Szeman, and L.J. Kato, Fatty Acid-Cyclodextrin Complexes: Properties & Applications, Inclusion Phenom. Mol. Recognit. Chem. 16:339–354 (1993).

    Article  CAS  Google Scholar 

  6. Imagi, J., K. Muraya, D. Yamashita, S. Adahi, and R. Matsuno, Retarded Oxidation of Liquid Lipids Entrapped in Matrixes of Saccharides or Proteins, Biosci. Biotechnol. Biochem. 56:1236–1240 (1992).

    Article  CAS  Google Scholar 

  7. Shimada, K., K. Fujikawa, K. Yahara, and T.J. Nakamura, Antioxidative Properties of Xanthan on the Autoxidation of Soybean Oil in Cyclodextrin Emulsion, J. Agric. Food Chem. 40:945–948 (1992).

    Article  CAS  Google Scholar 

  8. Jyothirmayi, N., C.S. Ramadoss, and S.J. Divakar, Nuclear Magnetic Resonance Studies of Cyclodextrin Complexes of Linoleic Acid and Arachidonic Acid, Ibid.:2123–2127 (1991).

    Article  CAS  Google Scholar 

  9. Laakso, S., Stabilization of Lipids by Molecular Inclusion: Cyclodextrins and Casein as Antioxidants, in Lipid Oxidation: Biological Food Chemical Aspects, edited by R. Marcuse, Scandinavian Forum of Lipid Research Technology, Göteborg, Sweden, 1986, pp. 165–170.

  10. Laakso, S., Inhibition of Lipid Peroxidation by Casein, Biochim. Biophys. Acta 792:11–15 (1984).

    PubMed  CAS  Google Scholar 

  11. Parker, S.P. (ed.), in McGraw-Hill Encyclopedia of Science and Technology, 7th edn., McGraw-Hill Book Co., New York, 1992, Vol. 2, p. 222.

    Google Scholar 

  12. SAS Institute, Inc., SAS/STAT User’s Guide, Version 6, 4th edn., SAS Institute, Cary, 1990.

    Google Scholar 

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Correspondence to David B. Min.

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Reichenbach, W.A., Min, D.B. Oxidative stability and nuclear magnetic resonance analyses of linoleic acid encapsulated in cyclodextrins. J Amer Oil Chem Soc 74, 1329–1333 (1997). https://doi.org/10.1007/s11746-997-0065-5

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  • DOI: https://doi.org/10.1007/s11746-997-0065-5

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