Encapsulation of hydroxycitronellal in β-cyclodextrin and the characteristics of the inclusion complex

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

doi:10.2478/pjct-2023-0004

Abstract

Hydroxycitronellal has been widely used in foods, beverages, perfumery and cosmetics. It can also be used to treat anxiety. The major drawbacks regarding the use of hydroxycitronellal are related to water insolubility, volatility, instability, and sensitization. To overcome these concerns, β-cyclodextrin was adopted as wall material to encapsulate hydroxycitronellal in this work. Hydroxycitronellal-β-cyclodextrin inclusion complex was prepared and the product was characterized. The interaction of hydroxycitronellal and β-cyclodextrin, and the assembly of hydroxycitronellal-β-cyclodextrin inclusion complex were investigated by molecular simulation (MM). The results showed that hydroxycitronellal loading capacity was 8.5%. The thermal stability and lastingness of hydroxycitronellal were improved by the formation of the inclusion complex. The minimum binding energy was –151.2 kJ/mol. Among the perpendicular, staggered parallel and ideally parallel orientation of the inclusion complexes, the minimum energy value was found for the staggered parallel arrangement. These basic data are useful to understand the interaction between hydroxycitronellal and β-cyclodextrin.

References

Surburg, H. & Panten, J. (2006). Common Fragrance and Flavor Materials. Weinheim, Wiley-Vch Verlag GmbH & Co. KGaA.
Search in Google Scholar Back to article
Burdock, G.A. (2010). Fenaroli’s handbook of flavor ingredients. Boca Raton, CRC Press.
Search in Google Scholar Back to article
Andrade, J.C., Monteiro, Á.B., Andrade, H.H.N., Gonzaga, T.K.S.N., Silva, P.R., Alves, D.N., Castro, R.D., Maia, M.S., Scotti, M.T., Sousa, D.P. & Almeida, Reinaldo N. (2021). Involvement of GABAA receptors in the anxiolytic-like effect of hydroxycitronellal. BioMed Res. Int. Article ID 9929805. DOI: 10.1155/2021/9929805
Open DOI Search in Google Scholar Back to article
Teixeira, M.A., Rodríguez, O., Gomes, P., Mata, V. & Rodrigues, A.E. (2013). Perfume Engineering: Design, Performance & Classification, New York, Elsevier Ltd.
Search in Google Scholar Back to article
Zhou, M. & Liu, J. (2000). Study on the permeability of cinnamic aldehyde and hydroxycitronellal in vitro. Chinese J. Health Labor. Technol., 10(2), 135–137. DOI: CNKI:SUN:ZWJZ.0.2000-02-003.
Open DOI Search in Google Scholar Back to article
Liu S. (2000). Technological Manuals of Synthetic Aroma Chemical, Beijing, China Light Industry Press Ltd.
Search in Google Scholar Back to article
Heydorn, S., Andersen, K.E., Johansen, J.D. & Menné, T. (2003). A stronger patch test elicitation reaction to the allergen hydroxycitronellal plus the irritant sodium lauryl sulfate. Contact Dermatitis 49, 133–139. DOI: 10.1111/j.0105-1873.2003.00175.x.
Open DOI Search in Google Scholar Back to article
Calnan, C.D. (1979). Unusual hydroxycitronellal perfume dermatitis. Contact Dermatitis 5(2), 123–123. DOI: 10.1111/j.1600-0536.1979.tb04816.x.
Open DOI Search in Google Scholar Back to article
Steltenkamp, R.J., Booman, K.A., Dorsky, J., King, T.O., Rothenstein, A.S., Schwoeppe, E.A., Sedlak, R.I., Smith T.H.F. & Thompson, G.R. (1980). Hydroxycitronellal: a survey of consumer patch-test sensitization. Food Cosm. Toxicol. 18, 407–412. DOI: 10.1016/0015-6264(80)90198-4.
Open DOI Search in Google Scholar Back to article
Ford, R.A., Api, A.M. & Suskind, R.R. (1988). Allergic contact sensitization potential of hydroxycitronellal in humans. Food Chem. Toxicol. 26, 921–926. DOI: 10.1016/0278-6915(88)90090-7.
Open DOI Search in Google Scholar Back to article
Liu, X., Wu, J., Wang, M. & Zhang, M. (2021). Research progress of cometic delivery system: application of pharmaceutical new dosage forms and new techniques in cosmetics. Flavour Frag. Cosmetics, 6, 99–105. (in Chnises).
Search in Google Scholar Back to article
Amann, M. & Dressnandt, G. (1993). Solving problems with cyclodextrins in cosmetics. Cosmetics and Toiletries, 108, 90–95.
Search in Google Scholar Back to article
Chen, N., Zhang, H. & Li, L. (2022). The carrier structure of retinol and retinol derivatives and its application in cosmetics. Chem. World 63(1), 51–56. (in Chinese). DOI: 10.19500/j. cnki.0367-6358.20200814.
Open DOI Search in Google Scholar Back to article
Celebioglu, A., Yildiz, Z.I. & Uyar, T. (2018). Thymol/cyclodextrin inclusion complex nanofibrous webs: Enhanced water solubility, high thermal stability and antioxidant property of thymol. Food Res. Int. 106, 280–290. DOI: 10.1016/j. foodres.2017.12.062.
Open DOI Search in Google Scholar Back to article
Kibici, D. & Kahveci, D. (2019). Effect of emulsifier type, maltodextrin, and β-cyclodextrin on physical and oxidative stability of oil-in-water emulsions. J. Food Sci. 84(6), 1273–1280. DOI: 10.1111/1750-3841.14619.
Open DOI Search in Google Scholar Back to article
Perinelli, D.R., Palmieri, G.F., Cespi, M. & Bonacucina, G. (2020). Encapsulation of Flavours and Fragrances into Polymeric Capsules and Cyclodextrins Inclusion Complexes: An Update. Molecules 25, 5878. DOI: 10.3390/molecules25245878.
Open DOI Search in Google Scholar Back to article
Kayaci, F., Sen, H.S., Durgun, E. & Uyar, T. (2014). Functional electrospun polymeric nanofibers incorporating geraniol–cyclodextrin inclusion complexes: High thermal stability and enhanced durability of geraniol. Food Res. Int. 62, 424–431. DOI: 10.1016/j.foodres.2014.03.033.
Open DOI Search in Google Scholar Back to article
Siva, S., Li, C., Cui, H. & Lin, L. (2019). Encompassment of isoeugenol in 2-hydroxypropyl-β-cyclodextrin using ultrasonication: Characterization, antioxidant and antibacterial activities. J. Mol. Liq. 296, 111777. DOI: 10.1016/j.molliq.2019.111777
Open DOI Search in Google Scholar Back to article
Real, D., Leonardi, D., WilliamsIII, R.O., Repka, M.A. & Salomon, C.J. (2018). Solving the Delivery Problems of Triclabendazole Using Cyclodextrins. AAPS PharmSciTech 19, 2311–2321. DOI: 10.1208/s12249-018-1057-5.
Open DOI Search in Google Scholar Back to article
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
Zhu, G., Zhu, G. & Xiao, Z. (2021). Study of formation constant, thermodynamics and β-ionone release characteristic of β-ionone-hydroxypropyl-β-cyclodextrin inclusion complex. Polym. Bull. 78, 247–260. DOI: 10.1007/s00289-020-03108-4.
Open DOI Search in Google Scholar Back to article
Zhu, G., Xiao, Z., Yu, G., Zhu, G., Niu, Y. & Liu, J. (2021). Formation and characterization of furfuryl mercaptan-β-cyclodextrin inclusion complex and its thermal release characteristics. Pol. J. Chem. Technol. 23(4), 35–40. DOI: 10.2478/pjct-2021-0035.
Open DOI Search in Google Scholar Back to article
Zhu, G., Xiao, Z. & Zhu, G. (2021). Fabrication and characterization of ethyl acetate-hydroxypropyl-β-cyclodextrin inclusion complex. J. Food Sci. 86, 3589–3597. DOI: 10.1111/1750-3841.15835.
Open DOI Search in Google Scholar Back to article
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 analoguess beyond the doughnut. Chem. Rev. 98, 1787–1802. DOI: 10.1021/cr9700181.
Open DOI Search in Google Scholar Back to article
He, Y., Fu, P., Shen, X. & Gao, H. (2008). Cyclodextrin-based aggregates and characterization by microscopy. Micron 39, 495–516. DOI: 10.1016/j.micron.2007.06.017.
Open DOI Search in Google Scholar Back to article
Stuart, B. (1996). Modern Infrared Spectroscopy. New York, John Wiley & Sons27.Ning, Y. (2010). Spectroscopy in Organic Chemistry and Spectral Analysis. Beijing, China Science Publishing & Media Ltd.
Search in Google Scholar Back to article
Ning, Y. (2010). Spectroscopy in Organic Chemistry and Spectral Analysis. Beijing, China Science Publishing & Media Ltd.
Search in Google Scholar Back to article
Zhu, G., Zhu, G. & Xiao, Z. (2019). A review of the production of slowrelease 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
Zhu, G., Jin, Y., Xiao, Z. & Zhu, G. (2022). Preparation and characterization of the dimethyl sulfide-β-cyclodextrin inclusion complex. J. Food Sci. 87, 3084–3094. DOI: 10.1111/1750-3841.16216.
Open DOI Search in Google Scholar Back to article
Zhu, G., Xiao, Z., Zhou, R., Liu, J., Zhu, G. & Zheng X. (2022). (-)-Menthol-β-cyclodextrin inclusion complex production and characterization. Pol. J. Chem. Technol. 24(2), 1–7. DOI: 10.2478/pjct-2022-0008.
Open DOI Search in Google Scholar Back to article

Encapsulation of hydroxycitronellal in β-cyclodextrin and the characteristics of the inclusion complex

Abstract

Paradigm

My account