(-)-Menthol-β-cyclodextrin inclusion complex production and characterization

Zhu, Guangyong; Xiao, Zuobing; Zhou, Rujun; Liu, Junhua; Zhu, Guangxu; Zheng, Xiongjian

doi:10.2478/pjct-2022-0008

References

1. Surburg, H. & Panten, J. (2006). Common Fragrance and Flavor Materials. Weinheim, Germany: Wiley-VCH.10.1002/3527608214
Search in Google Scholar Back to article
2. Burdock, G.A. (2010). Fenaroli’s Handbook of Flavor Ingredients. Boca Raton, USA: CRC Press. (2010).
Search in Google Scholar Back to article
3. Hu, Z., Li, S., Wang, S., Zhang, B. & Huang, Q. (2021). Encapsulation of menthol into cyclodextrin metal-organic frameworks: Preparation, structure characterization and evaluation of complexing capacity. Food. Chem. 338, 127839. DOI: 10.1016/j.foodchem.2020.127839.32822901
Open DOI Search in Google Scholar Back to article
4. Soottitantawata, A., Takayamaa, K., Okamuraa, K., Muranakaa, D., Yoshiia, H., Furutaa, T., Ohkawarab, 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.
Open DOI Search in Google Scholar Back to article
5. Biswas, L., Harrison, E., Gong, Y., Avusula, R., Lee, J., Zhang, M., Rousselle, T., Lage, J. & Liu, X. (2016). Enhancing effect of menthol on nicotine self-administration in rats. Psycho-pharmacology 233, 3417–3427. DOI: 10.1007/s00213-016-4391-x.499049927473365
Open DOI Search in Google Scholar Back to article
6. Lawrence, D., Cadman, B. & Hoffman, A.C. (2011). Sensory properties of menthol and smoking topography. Tob. Induc. Dis. 9(Suppl. 1), S3. DOI: 10.1186/1617-9625-9-S1-S3310290221624149
Open DOI Search in Google Scholar Back to article
7. Cadham, C.J., Sanchez-Romero, L.M., Fleischer, N.L., Mistry, R., Hirschtick, J.L., Meza, R. & Levy, D.T. (2020). The actual and anticipated effects of a menthol cigarette ban: a scoping review. BMC Public Health 20, 1055. DOI: 10.1186/s12889-020-09055-z.734660632641026
Open DOI Search in Google Scholar Back to article
8. Wang, H. & Meng, F. (2017). The permeability enhancing mechanism of menthol on skin lipids: a molecular dynamics simulation study. J. Mol. Model., 23, 279. DOI: 10.1007/s00894-017-3457-y.28914377
Open DOI Search in Google Scholar Back to article
9. Xu, X., Yu, N., Bai, Z., Xun, Y., Jin, D., Li, Z. & Cui, H. (2011). Effect of menthol on ocular drug delivery. Graef. Arch. Clin. Exp. Ophthalmol. 249, 1503–1510. DOI: 10.1007/s00417-011-1703-z.21597947
Open DOI Search in Google Scholar Back to article
10. Shen, Q., Li, X., Li, W. & Zhao, X. (2011). Enhanced intestinal absorption of daidzein by borneol/menthol eutectic mixture and microemulsion. AAPS PharmSciTech 12(4), 1044–1049. DOI: 10.1208/s12249-011-9672-4.322555421842308
Open DOI Search in Google Scholar Back to article
11. Xia, Q.-p., Chang, L., Mo, Y.-F. & Deng, L. (2020). Experimental study of the influence of menthol on the ozone treatment for corneal alkali burn in rats. Chinese J. Drug Appl. Monit. 17(3), 148–151. (in Chinese).
Search in Google Scholar Back to article
12. Flood, T.R., Waldron, M. & Jeffries, O. (2017). Oral lmenthol reduces thermal sensation, increases workrate and extends time to exhaustion, in the heat at a fixed rating of perceived exertion. Eur. J. Appl. Physiol. 117, 1501–1512. DOI: 10.1007/s00421-017-3645-6.28508114
Open DOI Search in Google Scholar Back to article
13. Barwood, M.J., Corbett, J., Thomas, K. & Twentyman, P. (2015). Relieving thermal discomfort: Effects of sprayed L-menthol on perception, performance, and time trial cycling in the heat. Scand. J. Med. Sci. Spor. 25 (Suppl. 1), 211–218. DOI: 10.1111/sms.12395.
Open DOI Search in Google Scholar Back to article
14. Jang, Y.-J., Kim, J.-H. & Lee, J.-Y. (2015). Effects of menthol on thermoregulatory responses after exercise-induced hyperthermia. Extreme Physiol. Medicine 4(Suppl 1), A6. DOI:10.1186/2046-7648-4-S1-A6.
Open DOI Search in Google Scholar Back to article
15. Kounalakis, S.N., Botonis, P.G., Koskolou, M.D. & Geladas, N.D. (2010). The effect of menthol application to the skin on sweating rate response during exercise in swimmers and controls. Eur. J. Appl. Physiol. 109, 183–189. DOI: 10.1007/s00421-009-1345-6.
Open DOI Search in Google Scholar Back to article
16. Wang, Z.-f., Ding, Z.-m., He, J., Ma, Y.-M. & Yang, W.-J. (2020) Progress in chemical constituents, pharmacological activities and product development of mentha haplocalyx Briq. Mod. Chin. Med. 22(6), 979–984. DOI: 10.13313/j.issn.1673-4890.20190513002 (in Chinese).
Open DOI Search in Google Scholar Back to article
17. Sabzghabaee, A.M., Nili, F., Ghannadi, A., Eizadi-Mood, N. & Anvari, M. (2011). Role of menthol in treatment of candidial napkin dermatitis. World J. Pediatr. 7(2), 167–170. DOI: 10.1007/s12519-011-0253-0.
Open DOI Search in Google Scholar Back to article
18. Kong, L., Zuo, H. & Wu, C. (2020). Study on the mechanism of active ingredients of peppermint in the treatment of chronic cholecystitis based on network pharmacology. Chinese J. Ethnomed. Ethnopharmacy 29(8), 27–33. DOI:CNKI:SUN:MZMJ.0.2020-08-007 (in Chinese).
Open DOI Search in Google Scholar Back to article
19. Yoshida, N., Naito, Y., Hirose, R., Ogiso, K., Inada, Y., Fernandopulle, N., Kamada, K., Katada, K., Uchiyama, K., Handa, O., Takagi, T., Konishi, H., Yagi, N., Wakabayashi, N., Yanagisawa, A. & Itoh, Y. (2014). Prevention of colonic spasm using L-menthol in colonoscopic examination. Int. J. Colorectal Dis. 29, 579–583. DOI: 10.1007/s00384-014-1844-8.
Open DOI Search in Google Scholar Back to article
20. Li, R., Zhang, N., Yao, L. & Li, Y.-h. (2020). Study on the hair growth promotion effect of lavender essential oil and Asian mint essential oil, China Surfactant Deterg. Cosmet., 50(8), 536–541. DOI: 10.3969/j.issn.1001-1803.2020.08.005 (in Chinese).
Open DOI Search in Google Scholar Back to article
21. Ferreira, A.l., Silva, W.d.S.e., Neves, L.d.C., Ferreira, N.S., Takata, R. & Luz, R.K. (2020). Benzocaine and menthol as anesthetics for the African cichlid Aulonocara nyassae. Aquacult. Int., 28, 1837–1846. DOI: 10.1007/s10499-020-00561-w.
Open DOI Search in Google Scholar Back to article
22. Zhu, G., Xiao, Z., Zhu, G., Rujunzhou & Niu, Y. (2016). Encapsulation of l-menthol in hydroxypropyl-β-cyclodextrin and release characteristics of the inclusion complex. Pol. J. Chem. Technol. 18, 110–116. DOI: 10.1515/pjct-2016-0056.
Open DOI Search in Google Scholar Back to article
23. Yildiz, Z.I., Celebioglu, A., Kilic, M.E., Durgun, E. & Uyar, T. (2018). Menthol/cyclodextrin inclusion complex nanofibers: Enhanced water-solubility and high-temperature stability of menthol. J. Food Eng., 224, 27–36. DOI:10.1016/j.jfoodeng.2017.12.020.
Open DOI Search in Google Scholar Back to article
24. Martel, B., Morcellet, M., Ruffin, D., Vinet, F. & Weltrowski, M. (2002). Capture and controlled release of fragrances by CD finished textiles. J. Incl. Phenom. Macro. Chem., 44, 439–442. DOI:10.1023/a:1023028105012.
Open DOI Search in Google Scholar Back to article
25. Fernando Ayala-Zavala, J., Soto-Valdez, H., González-León, A., Álvarez-Parrilla, E., Martín-Belloso, O. & González-Aguilar, G.A. (2008). Microencapsulation of cinnamon leaf (Cinnamomum zeylanicum) and garlic (Allium sativum) oils in β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem., 60, 359–368. DOI: 10.1007/s10847-007-9385-1.
Open DOI Search in Google Scholar Back to article
26. Yoshii, H., Sakane, A., Kawamura, D., Neoh, T.L., Kajiwara, H. & Furuta, T. (2007). Release kinetics of (-)-menthol from chewing gum. J. Incl. Phenom. Macrocycl. Chem., 57, 591–596. DOI: 10.1007/s10847-006-9279-7.
Open DOI Search in Google Scholar Back to article
27. Zhu, G., Xiao, Z. & Zhu, G. (2017). Preparation, characterization and the release kinetics of mentha-8-thiol-3-one-β-cyclodextrin inclusion complex. Polym. Bull. 74, 2263–2275. DOI: 10.1007/s00289-016-1835-8.
Open DOI Search in Google Scholar Back to article
28. Zhu, G., Jiang, X., Zhu, G. & Xiao, Z. (2020). Encapsulation of difurfuryl disulfde in β-cyclodextrin and release characteristics of the guest from its inclusion complex. J. Incl. Phenom. Macro. Chem., 96, 263–273. DOI: 10.1007/s10847-019-00967-x.
Open DOI Search in Google Scholar Back to article
29. Zhu, G., Feng, N., Xiao, Z., Zhou, R. & Niu, Y. (2015). Production and pyrolysis characteristics of citralmonochlorotriazinyl-β-cyclodextrin inclusion complex. J. Therm. Anal. Calorime., 120, 1811–1817. DOI:10.1007/s10973-015-4498-z.
Open DOI Search in Google Scholar Back to article
30. Saenger, W., Jacob, J., Gessler, K., Steiner, T., Hoffmann, D., Sanbe, H., Koizumi, K., Smith, S.M. & Takaha, T. (1998). Structures of the common cyclodextrins and their larger analogues beyond the doughnut. Chem. Rev. 98, 1787–1802. DOI: 10.1021/cr9700181.
Open DOI Search in Google Scholar Back to article
31. Polarz, S., Smarsly, B., Bronstein, L. & Antoniett, M. (2001) From Cyclodextrin Assemblies to Porous. Angew. Chem. Int. Ed. 40, 4417–4421. DOI: 10.1002/1521-3773(20011203)40:23<;4417::AID ANIE4417>3.0.CO;2-P.
Open DOI Search in Google Scholar Back to article
32. Zhu, G., Zhu, G. & Xiao, Z. (2019). A review of the production of slow-release favor by formation inclusion complex with cyclodextrins and their derivatives. J. Incl. Phenom. Macro. Chem. 95, 17–33. DOI: 10.1007/s10847-019-00929-3.
Open DOI Search in Google Scholar Back to article

(-)-Menthol-β-cyclodextrin inclusion complex production and characterization

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