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

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.2013.08.005.10.1016/j.phytochem.2013.08.00524054028Search in Google Scholar

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.2014.10.007.10.1016/j.jcat.2014.10.007Search in Google Scholar

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 effi cacy of l-menthol in upper gastrointestinal endoscopy. Clin. Pharmacol. The. 90, 221-338. DOI: 10.1038/clpt.2011.110.10.1038/clpt.2011.11021544078Search in Google Scholar

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 effi cacy of menthol on carcinogen-induced cutaneous carcinoma through inhibition of infl ammation and oxidative stress in mice. Food Chem. Toxicol. 82, 12-18. DOI: 10.1016/j.fct.2015.04.025.10.1016/j.fct.2015.04.02525956868Search in Google Scholar

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.2004.11.007.10.1016/j.ifset.2004.11.007Search in Google Scholar

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.10.1007/s10847-016-0599-ySearch in Google Scholar

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.1892.10.1002/ffj.1892Search in Google Scholar

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.64.1608.10.1271/bbb.64.160810993145Search in Google Scholar

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.2004.11.007.10.1016/j.ifset.2004.11.007Search in Google Scholar

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.2007.07.018.10.1016/j.jconrel.2007.07.01817888540Search in Google Scholar

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 fi rst 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.Search in Google Scholar

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.2014.07.042.10.1016/j.carbpol.2014.07.04225263871Search in Google Scholar

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.Search in Google Scholar

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.10.1007/s10973-015-4498-zSearch in Google Scholar

15. Zhu, G., Xiao, Z., Zhou, R. & Feng, N. (2015). Production of a transparent lavender fl avour nanocapsule aqueous solution and pyrolysis characteristics of fl avour nanocapsule. J. Food Sci. Technol. 52, 4607-4612. DOI: 10.1007/ s13197-014-1465-9.10.1007/s13197-014-1465-9448655526139932Search in Google Scholar

16. Zhu, G., Xiao, Z., Zhou, R. & Zhu, Y. (2014). Study of production and pyrolysis characteristics of sweet orange fl avour-β-cyclodextrin inclusion complex. Carbohyd. Polym. 105, 75-80. DOI: 10.1016/j.carbpol.2014.01.060.10.1016/j.carbpol.2014.01.06024708955Search in Google Scholar

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).Search in Google Scholar

18. Yuan, C. & Jin, Z.Y. (2007). Study on confi guration 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/cr9700179.10.1021/cr970017911848951Search in Google Scholar

19. Trivedi, M.K., Patil, S., Mishra, R.K. & Jana, S. (2015). Structural and physical properties of biofi eld treated thymol and menthol. J. Mol. Pharm. Proc. Res. 3, 127. DOI: 10.4172/2329-9053.1000127.10.4172/2329-9053.1000127Search in Google Scholar

20. Zeng, Z., Fang, Y. & Ji, H. (2012). Side chain infl uencing the interaction between β-cyclodextrin and vanillin. Flav. Fragr. J. 27, 378-85. DOI: 10.1002/ffj.3115.10.1002/ffj.3115Search in Google Scholar

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.14474.10.1002/aic.14474Search in Google Scholar

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.3186.10.1002/ffj.3186Search in Google Scholar

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-2015-0061.10.1515/pjct-2015-0061Search in Google Scholar

24. Coats, A.W. & Redfern, J.P. (1964). Kinetic parameters from thermogravimetric data. Nature 201, 68-69.10.1038/201068a0Search in Google Scholar

25. Levine, I.N. (2012). Physical Chemistry (6th ed.). Beijing, China: Tsinghua University Press limited. Search in Google Scholar