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Encapsulation of l-menthol in hydroxypropyl-β-cyclodextrin and release characteristics of the inclusion complex

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Treść / Zawartość
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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
l-menthol has been widely used in flavour, food and pharmaceuticals. Because of its high volatility and whisker growth, l-menthol-hydroxypropyl-β-cyclodextrin inclusion complex was produced to improve shelf-life, provide protection, and enhance the stability of l-menthol. The inclusion complex was characterized by Fourier transform infrared spectroscopy, X-ray diffraction. The results show that l-menthol was successfully encapsulated in hydroxypropyl-β-cyclodextrin. l-menthol loading capacity is about 8.44%. Geometries and binding energies of l-menthol-hydroxypropyl-β-cyclodextrin inclusion complexes were investigated using molecular mechanics calculations. The shape and orientation of the most stable complex, and the minimum binding energy were determined. L-menthol release from complex was determined by thermogravimetric analysis. Two l-menthol release rate peaks were observed at 69.3 and 279.1°C. The l-menthol release reaction order, release activation energy and the preexponential factor were obtained.
Rocznik
Strony
110--116
Opis fizyczny
Bibliogr. 25 poz., rys., tab.
Twórcy
autor
  • Shanghai Institute of Technology, No. 100 Haiquan Road, Shanghai, 201418, PR China
autor
  • Shanghai Institute of Technology, No. 100 Haiquan Road, Shanghai, 201418, PR China
autor
  • 14846, 43 Ave. Edmonton, Alberta, T6H 5S1, Canada
autor
  • Shanghai Institute of Technology, No. 100 Haiquan Road, Shanghai, 201418, PR China
autor
  • Shanghai Institute of Technology, No. 100 Haiquan Road, Shanghai, 201418, PR China
Bibliografia
  • 1. Kamatou, G.P.P., Vermaak, I., Viljoen, A.M. & Lawrence, B.M. (2013). Menthol: A simple monoterpene with remarkable biological properties. Phytochemistry 96, 15-25. DOI: 10.1016/j.phytochem.2013.08.005.
  • 2. Plößer, J., Lucas, M. & Claus, P. (2014). Highly selective menthol synthesis by one-pot transformation of citronellal using Ru/H-BEA catalysts. J. Catal. 320, 189-197. DOI: 10.1016/j.jcat.2014.10.007.
  • 3. Hiki, N., Kaminishi, M., Hasunuma, T., Nakamura, M., Nomura, S., Yahagi, N., Tajiri, H. & Suzuki, H. (2011). A phase I study evaluating tolerability, pharmacokinetics, and preliminary efficacy of l-menthol in upper gastrointestinal endoscopy. Clin. Pharmacol. The. 90, 221-338. DOI: 10.1038/clpt.2011.110.
  • 4. Liu, Z., Shen, C., Tao, Y., Wang, S., Wei, Z., Cao, Y., Wu, H., Fan, F., Lin, C., Shan, Y., Zhu, P., Sun, L., Chen, C., Wang, A., Zheng, S. & Lu, Y. (2015). Chemopreventive efficacy of menthol on carcinogen-induced cutaneous carcinoma through inhibition of inflammation and oxidative stress in mice. Food Chem. Toxicol. 82, 12-18. DOI: 10.1016/j.fct.2015.04.025.
  • 5. Soottitantawat, A., Takayama, K., Okamura, K., Muranaka, D., Yoshii, H., Furuta, T., Ohkawara, M. & Linko, P. (2005). Microencapsulation of l-menthol by spray drying and its release characteristics. Innov. Food Sci. Emerg. 6, 163-170. DOI: 10.1016/j.ifset.2004.11.007.
  • 6. Zhu, G., Xiao, Z., Zhou, R. & Niu, Y. (2016). Kinetics and release characteristics of menthyl acetate from its β-cyclodextrin inclusion complex by thermogravimetric analysis. J. Incl. Phenom. Macrocycl. Chem. 84, 219-224. DOI: 10.1007/s10847-016-0599-y.
  • 7. Mortenson, M.A. & Reineccius G.A. (2008). Encapsulation and release of menthol. Part 2: direct monitoring of L-menthol release from spray-dried powders made with OSAn-substituted dextrins and gum acacia. Flavour Fragr. J. 23, 407-415. DOI: 10.1002/ffj.1892.
  • 8. Liu X.D., Furuta, T., Yoshii, H., Linko, P. & Coumans, W.J. (2000). Cyclodextrin encapsulation to prevent the loss of l-menthol and its retention during drying. Biosci. Biotechnol. Biochem. 64, 1608-1613. DOI: 10.1271/bbb.64.1608.
  • 9. Kayaci, F. & Uyar, T. (2012). Encapsulation of vanillin/ cyclodextrin inclusion complex in electrospun polyvinyl alcohol (PVA) nanowebs: Prolonged shelf-life and high temperature stability of vanillin. Food Chem. 133, 641-649. DOI: 10.1016/j.ifset.2004.11.007.
  • 10. Carrier, R.L., Miller, L.A. & Ahmed, I. (2007). The utility of β-cyclodextrins for enhancing oral bioavailability, J. Control. Rel. 123, 78-99. DOI: 10.1016/j.jconrel.2007.07.018.
  • 11. Rassu, G., Soddu, E., Cossu, M., Brundu, A., Cerri, G., Marchetti, N., Ferraro, L., Regan, R.F., Giunchedi, P., Gavini, E. & Dalpiaz, A. (2015). Solid microparticles based on chitosan or methyl-β-cyclodextrin: A first formulative approach to increase the nose-to-brain transport of deferoxamine mesylate. J. Control. Rel. 201, 68-77. DOI: 10.1016/j. jconrel.2015.01.025.
  • 12. Hsu, C.M., Tsai, F.J. & Tsa, Y. (2014). Inhibitory effect of Angelica sinensis extract in the presence of 2-hydroxypropyl- β-cyclodextrin. Carbohyd. Polym. 114, 115-122. DOI: 10.1016/j.carbpol.2014.07.042.
  • 13. Ol’khovich, M.V., Sharapova, A.V., Lavrenov, S.N., Blokhina, S.V. & Perlovich, G.L. (2014). Inclusion complexes of hydroxypropyl-β-cyclodextrin with novel cytotoxic compounds: Solubility and thermodynamic properties. Fluid Phase Equilibr. 384, 68-72. DOI: 10.1016/j.fl uid.2014.10.030.
  • 14. Zhu, G., Feng, N., Xiao, Z., Zhou, R. & Niu, Y. (2015). Production and pyrolysis characteristics of citralmonochlorotriazinyl- β-cyclodextrin inclusion complex. J. Therm. Anal. Calorim. 120, 1811-1817. DOI: 10.1007/ s10973-015-4498-z.
  • 15. Zhu, G., Xiao, Z., Zhou, R. & Feng, N. (2015). Production of a transparent lavender fl avour nanocapsule aqueous solution and pyrolysis characteristics of flavour nanocapsule. J. Food Sci. Technol. 52, 4607-4612. DOI: 10.1007/ s13197-014-1465-9.
  • 16. Zhu, G., Xiao, Z., Zhou, R. & Zhu, Y. (2014). Study of production and pyrolysis characteristics of sweet orange flavour-β-cyclodextrin inclusion complex. Carbohyd. Polym. 105, 75-80. DOI: 10.1016/j.carbpol.2014.01.060.
  • 17. Chen, Q. & Guo, P. (2009). Inclusion compound of menthol with hydroxypropyl-β-cyclodextrin by infrared spectroscopy. Cent. South Pharm. 7, 749-752. (In Chinese).
  • 18. Yuan, C. & Jin, Z.Y. (2007). Study on configuration of hydroxypropyl-β-cyclodextrin, J. Food Sci. Biotech. 26, 34-36. (In Chinese). Lipkowitz, K.B. (1998). Applications of computational chemistry to the study of cyclodextrins. Chem. Rev. 98, 1829-1873. DOI: 10.1021/cr9700179.
  • 19. Trivedi, M.K., Patil, S., Mishra, R.K. & Jana, S. (2015). Structural and physical properties of biofield treated thymol and menthol. J. Mol. Pharm. Proc. Res. 3, 127. DOI: 10.4172/2329-9053.1000127.
  • 20. Zeng, Z., Fang, Y. & Ji, H. (2012). Side chain influencing the interaction between β-cyclodextrin and vanillin. Flav. Fragr. J. 27, 378-85. DOI: 10.1002/ffj.3115.
  • 21. Chai, K. & Ji, H. (2014). Inclusive seperation of acetophenone from petrochemical by-product with 1-phenylethanol via noncovalent interactions. AIChE J. 60, 2962-2975. DOI: 10.1002/aic.14474.
  • 22. Yang, Z., Zeng, Z., Xiao, Z. & Ji, H. (2014). Preparation and controllable release of chitosan/vanillin microcapsules and their application to cotton fabric. Flav. Fragr. J. 29, 114-120. DOI: 10.1002/ffj.3186.
  • 23. Zhu, G., Xiao, Z., Zhou, R. & Niu, Y. (2015). Pyrolysis Characteristics and kinetics of cyclodextrin and its two derivatives. Pol. J. Chem. Technol. 17, 1-4. DOI: 10.1515/ pjct-2015-0061.
  • 24. Coats, A.W. & Redfern, J.P. (1964). Kinetic parameters from thermogravimetric data. Nature 201, 68-69.
  • 25. Levine, I.N. (2012). Physical Chemistry (6th ed.). Beijing, China: Tsinghua University Press limited.
Uwagi
Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę.
Autor Zhou R. w artykule jest błędnie wpisany - Rujunzhou.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-9c3112eb-df00-4c5d-b8ae-88ee636873e0
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