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Can conversion mixture substitute beta-cyclodextrin in encapsulation of essential oils and their components?

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Abstract

Complexation of some monoterpene flavors with beta-cyclodextrin is shown in details to demonstrate the effect of molecular encapsulation on thermal stability and on storage stability of these aroma components and of some essential oils containing them. Thermal analysis was used to distinguish between the really included flavor and that bound on the surface. The solubilizing and stabilizing efficiency of the three natural cyclodextrins and their mixture with linear dextrins (conversion mixture, an intermediate product of cyclodextrin manufacturing) were evaluated with two model flavors: thymol and vanillin and two essential oils: thyme oil and oregano oil both containing thymol as main component. Interestingly, the stabilizing effect of the conversion mixture was only slightly inferior compared to that of the pure cyclodextrins. Utilization of conversion mixture seems to be an economic compromise for flavor encapsulation.

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References

  1. Szente, L., Szejtli, J.: Cyclodextrins as food ingredients. Trends Food Sci. Tech. 15(3–4), 137–142 (2004)

    Article  CAS  Google Scholar 

  2. Hashimoto, H.: CyD applications in food, cosmetic, toiletry, textile and wrapping material fields. In: Dodziuk, H. (ed.) Cyclodextrins and Their Complexes, pp. 452–459. Wiley, Weinheim (2008)

    Google Scholar 

  3. Hedges A.R., Shieh W.J., Sikorski C.T.: Use of cyclodextrin for encapsulation in the use and treatment of food products. In: ACS Symposium Series 590: Encapsulation and Controlled Release of Food Ingredients (206th National Meeting of the American Chemical Society, Chicago, Illinois, August 22–27, 1993), pp. 60–73 (1995)

  4. Cravotto, G., Binello, A., Baranelli, E., Carraro, P., Trotta, F.: Cyclodextrins as food additives and in food processing. Curr. Nutr. Food Sci. 2(4), 343–350 (2006)

    Article  CAS  Google Scholar 

  5. Astray, G., Gonzalez-Barreiro, C., Mejuto, J.C., Rial-Otero, R., Simal-Gandara, J.: A review on the use of cyclodextrins in foods. Food Hydrocoll. 23(7), 1631–1640 (2009)

    Article  CAS  Google Scholar 

  6. Martina, K., Binello, A., Lawson, D., Jicsinszky, L., Cravotto, G.: Recent applications of cyclodextrins as food additives and in food processing. Curr. Nutr. Food Sci. 9(4), 167–179 (2013)

    Article  CAS  Google Scholar 

  7. Martina, K., Cravotto, G.: Cyclodextrin as food additives in food processing. In: Salem, M.A. (ed.) Functional Polymers in Food Science: From Technology to Biology, vol. II, Chap 12. Scrivener Publishing LLC, Published Online: 27 Mar 2015 DOI: 10.1002/9781119108580.ch12. Accessed 22 Sept 2015

  8. Szejtli, J.: Cyclodextrins and molecular encapsulation. In: Nalwa, H.S. (ed.) Encyclopedia of Nanoscience and Nanotechnology, vol. 2, pp. 283–304. American Scientific Publishers, Stevenson Ranch (2004)

    Google Scholar 

  9. Schmid, G.: Preparation and industrial production of cyclodextrins. In: Szejtli, J., Osa, T. (eds.) Comprehensive Supramolecular Chemistry, vol. 3, pp. 615–626. Elsevier, Oxford (1996)

    Google Scholar 

  10. Nakamura, N., Matsuzawa, M., Horikoshi, K.: Cyclic dextrin–containing starch–sugar powder. Japanese Patent 54044045 (1979)

  11. FDA Agency Response Letter GRAS Notice No. GRN 000046 (2000). http://www.accessdata.fda.gov/scripts/fdcc/?set=GRASNotices&id=46. Accessed 18 Aug 2015

  12. FDA Agency Response Letter GRAS Notice No. GRN 000074 (2001). http://www.accessdata.fda.gov/scripts/fdcc/?set=GRASNotices&id=74. Accessed 18. Aug 2015

  13. FDA Agency Response Letter GRAS Notice No. GRN 000155 (2004). http://www.accessdata.fda.gov/scripts/fdcc/?set=GRASNotices&id=155. Accessed 18 August 2015

  14. Szejtli, J., Szente, L., Banky-Elod, E.: Molecular encapsulation of volatile, easily oxidizable labile flavor substances by cyclodextrins. Acta Chim. Acad. Sci. Hung. 101(1–2), 27–46 (1979)

    CAS  Google Scholar 

  15. Szente, L., Szejtli, J.: Stabilization of flavors by cyclodextrins. ACS Symp. Ser. 370, 148 (1988)

    Article  CAS  Google Scholar 

  16. Bhandari, B., D’Arcy, B., Young, G.: Flavor retention during high temperature short time extrusion cooking process: a review. Int. J. Food Sci. Technol. 36(5), 453–461 (2001)

    Article  CAS  Google Scholar 

  17. Furuta, T., Yoshii, H., Shiga, H.: Microencapsulation of food flavorings by inclusion in cyclodextrin and by spray drying and its release characteristics. Foods & Food Ingred. J. Jpn. 191, 23–32 (2001)

    CAS  Google Scholar 

  18. Cabral Marques, H.M.: A review on cyclodextrin encapsulation of essential oils and volatiles. Flavour. Fragr J. 25(5), 313–326 (2010)

    Article  CAS  Google Scholar 

  19. Ciobanu, A., Landy, D., Fourmentin, S.: Complexation efficiency of cyclodextrins for volatile flavor compounds. Food Res. Int. 53(1), 110–114 (2013)

    Article  CAS  Google Scholar 

  20. Kuge, T., Takeo, K.: Complexes of starchy materials with organic compounds: Part I. Affinity observed by gas chromatography. Agric. Biol. Chem. 32, 753–758 (1968)

    CAS  Google Scholar 

  21. Maier, H.G., Bauer, A.: Binding of volatile aroma components on starch. Starch–Staerke 24, 101–107 (1972)

    Article  CAS  Google Scholar 

  22. Wulff, G., Avgenaki, G., Guzmann, M.S.P.: Molecular encapsulation of flavours as helical inclusion complexes of amylose. J. Cereal Sci. 41, 239–249 (2005)

    Article  CAS  Google Scholar 

  23. Tapanapunnitkul, O., Caiseri, S., Peterson, D.G., Thompson, D.B.: Water solubility of flavor compounds influences formation of flavor inclusion complexes from dispersed high–amylose maize starch. J. Agric. Food Chem. 56(1), 220–226 (2008)

    Article  Google Scholar 

  24. Rogers, W.I., Whaley, W.M.: Inclusion compound incorporating edible juice constituents. US Patent 3,061,444 (1962)

  25. Di Cesare, L.F., Nani, R., Mariani, N., D’Angelo, V.: Influence of maltodextrin, cyclodextrin and palm oil on the aroma retention of apricot powders. Ind. delle Bevande 25(142), 101–107 (1996)

    Google Scholar 

  26. Furuta, T., Yoshii, H., Kobayashi, T., Nishitarumi, T., Yasunishi, A.: Powdery encapsulation of d–limonene by kneading with mixed powders of beta–cyclodextrin and maltodextrin at low water content. Biosci. Biotechnol. Biochem. 58(5), 847–850 (1994)

    Article  CAS  Google Scholar 

  27. Liu, X.D., Furuta, T., Yoshii, H., Linko, P., Coumans, W.J.: Cyclodextrin encapsulation to prevent the loss of l–menthol and its retention during drying. Biosci. Biotechnol. Biochem. 64(8), 1608–1613 (2000)

    Article  CAS  Google Scholar 

  28. Shiga, H., Yoshii, H., Taguchi, R., Nishiyama, T., Furuta, T., Linko, P.: Release characteristics of flavor from spray–dried powder in boiling water and during rice cooking. Biosci. Biotechnol. Biochem. 67(2), 426–428 (2003)

    Article  CAS  Google Scholar 

  29. Yoshii, H., Yasuda, M., Furuta, T., Kuwahara, H., Ohkawara, M., Linko, P.: Retention of cyclodextrin complexed shiitake (Lentinus edodes) flavors with spray drying. Dry. Technol. 23(6), 1205–1215 (2005)

    Article  CAS  Google Scholar 

  30. Loftsson, T., Hreinsdottir, D., Masson, M.: Evaluation of cyclodextrin solubilization of drugs. Int. J. Pharm. 302(1–2), 18–28 (2005)

    Article  CAS  Google Scholar 

  31. Higuchi, T., Connors, K.A.: Phase solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–212 (1965)

    CAS  Google Scholar 

  32. Ueno, A., Kuwabara, T., Nakamura, A., Toda, F.: A modified cyclodextrin as a guest responsive color–change indicator. Nature (London) 356(6365), 136–137 (1992)

    Article  CAS  Google Scholar 

  33. Dornier, M., Jallageas, J.C., Serpelloni, M., Mentink, L., Crouzet, J.: Determination of association constants between beta–cyclodextrin and aroma compounds, In: Duchene D. (ed.), Minutes of International Symposium on Cyclodextrins, 5th pp. 230–233. Paris: Ed. Sante (1990)

  34. Astray, G., Mejuto, J.C., Morales, J., Rial-Otero, R., Simal-Gandara, J.: Factors controlling flavors binding constants to cyclodextrins and their applications in foods. Food Res. Int. 43(4), 1212–1218 (2010)

    Article  CAS  Google Scholar 

  35. Donze, C., Coleman, A.W.: Beta–cyclodextrin inclusion complexes: relative selectivity of terpene and aromatic guest molecules studied by competitive inclusion experiments. J. Incl. Phenom. Macrocycl. Chem. 16, 1–15 (1993)

    Article  CAS  Google Scholar 

  36. Ishikawa, H., Kuwano, A., Matsumoto, K.: Complexation of vanillin and ethylvanillin with alpha–, beta–, and gamma–cyclodextrin. J. Fac. Agric., Kyushu Univ., 52(1), 87–90. Chem. Abstr.: 147, 540420 (2007)

  37. Orgovanyi, J., Poeppl, L., Otta, H., Lovas, G.A.: Thermoanalytical method for studying the guest content in cyclodextrin inclusion complexes. J. Therm. Anal. Calorim. 81(2), 261–266 (2005)

    Article  CAS  Google Scholar 

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Acknowledgments

The HPLC measurements by Dr. Julianna Szemán and Katalin Csabai as well as the DSC studies by Prof. János Madarász are greatly acknowledged. The financial support of National Competitiveness Programme of Hungary (Fólia, GVOP–3.0–0217–04) and EU FP7 (Tornado Project, KBBE–2007–2–2–07–222720) is greatly acknowledged.

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Correspondence to Eva Fenyvesi.

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Fenyvesi, E., Zemlényi, C., Orgoványi, J. et al. Can conversion mixture substitute beta-cyclodextrin in encapsulation of essential oils and their components?. J Incl Phenom Macrocycl Chem 86, 55–66 (2016). https://doi.org/10.1007/s10847-016-0641-0

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