Abstract
Encapsulation aims at protecting components, providing controlled release, preventing oxidation and extending the shelf life. The inclusion complex of citral and monochlorotriazinyl-β-cyclodextrin has been studied. The scanning electron microscopy result showed that the dried citral–monochlorotriazinyl-β-cyclodextrin inclusion complexes formed aggregates with many geometric shapes in the size range 1–2 μm, and the transmission electron microscopy result shows that the inclusion complex aggregates were expressed through a bicontinuous “worm-type” pore system. Fourier transform infrared spectroscopy results show that citral enters the cavity of monochlorotriazinyl-β-cyclodextrin. The citral loading capacity determined from thermogravimetric data is about 8.96 %, and a 1:1 stoichiometry is obtained. Pyrolysis characteristics of the inclusion complexes were determined. Geometries of host, guest and the host–guest inclusion complex were optimized using molecular mechanics calculations. The binding energies for the most stable complexes geranial/monochlorotriazinyl-β-cyclodextrin and neral/monochlorotriazinyl-β-cyclodextrin are −143 and −162 kJ mol−1, respectively. The shapes and orientations of those complexes were presented.
Similar content being viewed by others
References
Zhu G, Xiao Z, Zhou R, Zhu Y. Study of production and pyrolysis characteristics of sweet orange flavor-β-cyclodextrin inclusion complex. Carbohydr Polym. 2014;105:75–80.
Schofield WCE, Badyal JPS. Controlled fragrant molecule release from surface-tethered cyclodextrin host-guest inclusion complexes. Appl Mater Interfaces. 2011;3:2051–6.
Menezes PP, Serafini MR, Quintans-Júnior LJ, Silva GF, Oliveira JF, Carvalho FMS, Souza JCC, Matos JR, Alves PB, Matos IL, Hǎdǎrugǎ DI, Araújo AAS. Inclusion complex of (–)-linalool and β-cyclodextrin. J Therm Anal Calorim. 2014;115:2429–37.
Serafini MR, Menezes PP, Costa LP, Lima CM, Quintans LJ Jr, Cardoso JC, Matos JR, Soares-Sobrinho JL, Grangeiro S Jr, Nunes PS, Bonjadim LR, Araújo AAS. Interaction of p-cymene with β-cyclodextrin. J Therm Anal Calorim. 2012;109:951–5.
Heghes A, Hǎdǎrugǎ NG, Fulias A-V, Bandur GN, Hǎdǎrugǎ DI, Dehelean C-A. Capsicum annuum extracts/β-cyclodextrin complexes. J Therm Anal Calorim. 2014;. doi:10.1007/s10973-014-4229-x.
Yao Q, You B, Zhou S, Chen M, Wang Y, Li W. Inclusion complexes of cypermethrin and permethrin with monochlorotriazinyl-beta-cyclodextrin: a combined spectroscopy, TG/DSC and DFT study. Spectrochim Acta A. 2014;117:576–86.
Vrinceanu N, Tanasa D, Hristodor CM, Brinza F, Popovici E, Gherca D, Pui A, Coman D, Carsmariu A, Bistricianu I, Broasca G. Synthesis and characterization of zinc oxide nanoparticles. J Therm Anal Calorim. 2013;111:1107–19.
Lipkowitz KB. Applications of computational chemistry to the study of cyclodextrins. Chem Rev. 1998;98:1829–73.
Salvatierra S, Jaime C, Virgili A, Sánchez-Ferrando F. Determination of the inclusion geometry for the γ-cyclodextrin/benzoic acid complex by NMR and molecular modeling. J Org Chem. 1996;61:9578–81.
Fathallah M, Fotiadu F, Jaime C. Cyclodextrin inclusion complexes. MM2 calculations reproducing bimodal inclusions. J Org Chem. 1994;59:1288–93.
Pérez F, Jaime C, Sánchez-Ruiz X. MM2 calculations on cyclodextrins: multimodal inclusion complexes. J Org Chem. 1995;60:3840–5.
Polarz S, Smarsly B, Bronstein L, Antonietti M. From cyclodextrin assemblies to porous materials by silica templating. Angew Chem Int Ed. 2001;40:4417–21.
He Y, Fu P, Shen X, Gao H. Cyclodextrin-based aggregates and characterization by microscopy. Micron. 2008;39:495–516.
Zhu G, Xiao Z, Zhou R, Feng N. Production of a transparent lavender flavour nanocapsule aqueous solution and pyrolysis characteristics of flavour nanocapsule. J Food Sci Technol. 2014;. doi:10.1007/s13197-014-1465-9.
Zhou W, Lin J, Wu R, Lin W, Ge F, Huang H. Direct synthesis of lemonile from litsea cubeba oil. Fine Chem. 2005;22:515–7 (in Chinese).
Zeng Z, Fang Y, Ji H. Side chain influencing the interaction between b-cyclodextrin and vanillin. Flavour Fragr J. 2012;27:378–85.
Yang Z, Zeng Z, Xiao Z, Ji H. Preparation and controllable release of chitosan/vanillin microcapsules and their application to cotton fabric. Flavour Fragr J. 2014;29:114–20.
Acknowledgements
This work was financially supported by the National Natural Science Fund of China (21276157, 21476140).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zhu, G., Feng, N., Xiao, Z. et al. Production and pyrolysis characteristics of citral–monochlorotriazinyl-β-cyclodextrin inclusion complex. J Therm Anal Calorim 120, 1811–1817 (2015). https://doi.org/10.1007/s10973-015-4498-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-015-4498-z