Abstract
There is a growing interest for aromatic and biological properties of essential oils as alternatives to synthetic chemicals and drugs. However, essential oils and their components are poorly soluble in aqueous systems and are highly sensitive to degradation and evaporation. These drawbacks can be overcome by encapsulation into cyclodextrins, which are non-toxic cyclic oligosaccharides obtained from the enzymatic degradation of starch. Cyclodextrins inclusion complexes offer solutions to many limitations of the use of essential oils in the food, pharmaceutical and cosmetic industries. This article reviews essential oils encapsulation in cyclodextrins. The strength of binding between cyclodextrins and essential oils components covers a wide range of formation constants with values ranging from 13 to 166,338 M−1. The encapsulation in cyclodextrins can increase the aqueous solubility of essential oils up to 16-fold and reduce their photodegradation rates up to 44-fold, while ensuring a gradual release. We also discuss the effect of encapsulation on biological activities, such as antimicrobial and antioxidant properties of essential oils. Finally, we present novel cyclodextrin-based approaches in the sectors of textiles and nanofibres.
This is a preview of subscription content, access via your institution.
(Adapted from Dima and Dima 2015)
Reprinted with permission from Kfoury et al. (2016g)
Reprinted with permission from Kfoury et al. 2015b
Notes
FDA: Code Fed. Regul. (CFR). Title 21 Food Drugs. Chapter I—Food Drug Adm. Dep. Heal. Hum. Serv. Subchapter B—Food Hum. Consum. (Continued), Part 182–Subst. Gen. Recognized as Safe (GRAS). 2016.
Essential Oil Market Analysis By Product (Orange, Corn Mint, Eucalyptus, Citronella, Peppermint, Lemon, Clove Leaf, Lime, Spearmint), By Application (Medical, Food & Beverage, Spa & Relaxation, Cleaning & Home) And Segment Forecasts To 2024.
See Vraz Kresevic et al. (2008).
References
Amidon GL, Lennernäs H, Shah VP, Crison JR (1995) A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 12:413–420. https://doi.org/10.1023/A:1016212804288
Arana-Sánchez A, Estarrón-Espinosa M, Obledo-Vázquez EN, Padilla-Camberos E, Silva-Vázquez R, Lugo-Cervantes E (2010) Antimicrobial and antioxidant activities of Mexican oregano essential oils (Lippia graveolens H. B. K.) with different composition when microencapsulated in β-cyclodextrin. Lett Appl Microbiol 50(6):585–590. https://doi.org/10.1111/j.1472-765X.2010.02837.x
Astray G, Gonzalez-Barreiro C, Mejuto JC, Rial-Otero R, Simal-Gándara J (2009) A review on the use of cyclodextrins in foods. Food Hydrocoll 23(7):1631–1640. https://doi.org/10.1016/j.foodhyd.2009.01.001
Astray G, Mejuto JC, Morales J, Rial-Otero R, Simal-Gandara J (2010) Factors controlling flavors binding constants to cyclodextrins and their applications in foods. Food Res Int 43(4):1212–1218. https://doi.org/10.1016/j.foodres.2010.02.017
Ayala-Zavala JF, Soto-Valdez H, Gonzalez-Leon A, Alvarez-Parrilla E, Martin-Belloso O, Gonzalez-Aguilar GA (2008) Microencapsulation of cinnamon leaf (Cinnamomum zeylanicum) and garlic (Allium sativum) oils in β-cyclodextrin. J Incl Phenom Macrocycl Chem 60:359–368. https://doi.org/10.1007/s10847-007-9385-1
Aytac Z, Yildiz ZI, Kayaci-Senirma F, KeskinNO San, Kusku SI, Durgun E, Tekinay T, Uyat T (2016a) Fast-dissolving, prolonged release, and antibacterial cyclodextrin/limonene-inclusion complex nanofibrous webs via polymer-free electrospinning. J Agric Food Chem 64(39):7325–7334. https://doi.org/10.1021/acs.jafc.6b02632
Aytac Z, Yildiz ZI, Kayaci-Senirmak F, San Keskin NO, Tekinayde T, Uyar T (2016b) Electrospinning of polymer-free cyclodextrin/geraniol-inclusion complex nanofibers: enhanced shelf-life of geraniol with antibacterial and antioxidant properties. RSC Adv 6(52):46089–46099. https://doi.org/10.1039/c6ra07088d
Bai Y, Yu B, Xu X, Jin Z, Tian Y, Lu L (2010) Comparison of encapsulation properties of major garlic oil components by hydroxypropyl β-cyclodextrin. Eur Food Res Technol 231(4):519–524. https://doi.org/10.1007/s00217-010-1307-6
Bakkali F, Averbeck S, Averbeck D, Idaomar M (2008) Biological effects of essential oils—a review. Food Chem Toxicol 46:446–475. https://doi.org/10.1016/j.fct.2007.09.106
Baránková E, Dohnal V (2016) Effect of additives on volatility of aroma compounds from dilute aqueous solutions. Fluid Phase Equilib 407:217–223. https://doi.org/10.1016/j.fluid.2015.05.038
Bertaut E, Landy D (2014) Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments. Beilstein J Org Chem 10:2630–2641. https://doi.org/10.3762/bjoc.10.275
Brasil IM, Gomes C, Puerta-gomez A, Castell-perez ME, Moreira RG (2012) Polysaccharide-based multilayered antimicrobial edible coating enhances quality of fresh-cut papaya. Food Sci Technol 47(1):39–45. https://doi.org/10.1016/j.lwt.2012.01.005
Brewster ME, Loftsson T (2007) Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59(7):645–666. https://doi.org/10.1016/j.addr.2007.05.012
Budryn G, Zaczyńska D, Rachwał-Rosiak D, Oracz J (2015) Changes in properties of food proteins after interaction with free and β encapsulated hydroxycinnamic acids. Eur Food Res Technol 240:1157–1166. https://doi.org/10.4315/0362-028X-68.5.919
Burt S (2004) Essential oils: their antibacterial properties and potential applications in foods—a review. Int J Food Microbiol 94:223–253. https://doi.org/10.1016/j.ijfoodmicro.2004.03.022
Burt SA, Vlielander R, Haagsman HP, Veldhuizen EJA (2005) Increase in activity of essential oil components carvacrol and thymol against Escherichia coli O157:h7 by addition of food stabilizers. J Food Prot 68(5):919–926. https://doi.org/10.4315/0362-028X-68.5.919
Carrier RL, Miller LA, Ahmed I (2007) The utility of cyclodextrins for enhancing oral bioavailability. J Control Release 123:78–99. https://doi.org/10.1016/j.jconrel.2007.07.018
Celebioglu A, Kayaci-Senirmak F, İpek S, Durgunab E, Uyar T (2016) Polymer-free nanofibers from vanillin/cyclodextrin inclusion complexes: high thermal stability, enhanced solubility and antioxidant property. Food Funct 7:3141–3153. https://doi.org/10.1039/C6FO00569A
Chen H, Ji H, Zhou X, Wang L (2010) Green synthesis of natural benzaldehyde from cinnamon oil catalyzed by hydroxypropyl-β-cyclodextrin. Tetrahedron 66(52):9888–9893. https://doi.org/10.1016/j.tet.2010.10.063
Ciobanu A, Mallard I, Landy D, Brabie G, Nistor D, Fourmentin S (2012) Inclusion interactions of cyclodextrins and crosslinked cyclodextrin polymers with linalool and camphor in Lavandula angustifolia essential oil. Carbohydr Polym 87(3):1963–1970. https://doi.org/10.1016/j.carbpol.2011.10.005
Ciobanu A, Landy D, Fourmentin S (2013) Complexation efficiency of cyclodextrins for volatile flavor compounds. Food Res Int 53(1):110–114. https://doi.org/10.1016/j.foodres.2013.03.048
Costa P, Medronho B, Gonc S, Romano A (2015) Cyclodextrins enhance the antioxidant activity of essential oils from three Lamiaceae species. Ind Crops Prod 70:341–346. https://doi.org/10.1016/j.indcrop.2015.03.065
Costa G, Gidaro MC, Vulla D, Supuran CT, Alcaro S (2016) Active components of essential Oils as anti-obesity potential drugs investigated by in silico techniques. J Agric Food Chem 64(26):5295–5300. https://doi.org/10.1021/acs.jafc.6b02004
Crini G (2014) Review: a history of cyclodextrins. Chem Rev 114(21):10940–10975. https://doi.org/10.1021/cr500081p
da Silveira E, Sá RDC, Andrade LN, De Oliveira RDRB, De Sousa DP (2014) A review on anti-inflammatory activity of phenylpropanoids found in essential oils. Molecules 19(2):1459–1480. https://doi.org/10.3390/molecules19021459
Decock G, Fourmentin S, Surpateanu GG, Landy D, Decock P, Surpateanu G (2006) Experimental and theoretical study on the inclusion compounds of aroma components with β-cyclodextrins. Supramol Chem 18(6):477–482. https://doi.org/10.1080/10610270600665749
Decock G, Landy D, Surpateanu G, Fourmentin S (2008) Study of the retention of aroma components by cyclodextrins by static headspace gas chromatography. J Incl Phenom Macrocycl 62:297–302
Del Valle EMM (2004) Cyclodextrins and their uses: a review. Process Biochem 39(9):1033–1046. https://doi.org/10.1016/S0032-9592(03)00258-9
Demian BA (2000) Correlation of the solubility of several aromatics and terpenes in aqueous hydroxypropyl-β-cyclodextrin with steric and hydrophobicity parameters. Carbohydr Res 328:635–639. https://doi.org/10.1016/S0008-6215(00)00139-7
Dima C, Dima S (2015) Essential oils in foods: extraction, stabilization, and toxicity. Curr Opin Food 5:29–35. https://doi.org/10.1016/j.cofs.2015.07.003
Dima C, Cotarlet M, Tiberius B, Bahrim G, Alexe P, Dima S (2014) Encapsulation of coriander essential oil in beta-cyclodextrin: antioxidant and antimicrobial properties evaluation. Rom Biotechnol Lett 19(2):9128–9141. https://doi.org/10.1016/j.foodhyd.2016.11.014
Donze C, Coleman W (1993) β-CD inclusion complexes: relative selectivity of terpene and aromatic guest molecules studied by competitive inclusion experiments. J Incl Phenom Macrocycl Chem 62(3–4):297–302. https://doi.org/10.1007/BF00708758
Eftink MR, Andy ML, Bystrom K, Perlmutter HD, Kristol DS (1989) Cyclodextrin inclusion complexes: studies of the variation in the size of alicyclic guests. J Am Chem Soc 111(17):6765–6772. https://doi.org/10.1021/ja00199a041
Fenyvesi E, Gruiz K, Verstichel S, De Wilde B, Leitgib L, Csabai K, Szaniszlo N (2005) Biodegradation of cyclodextrins in soil. Chemosphere 60:1001–1008. https://doi.org/10.1016/j.chemosphere.2005.01.026
Fenyvesi E, Szemán J, Csabai K, Malanga M, Szente L (2014) Methyl-beta-cyclodextrins: the role of number and types of substituents in solubilizing power. J Pharm Sci 103(5):1443–1452. https://doi.org/10.1002/jps.23917
Ferrazza R, Rossi B, Guella G (2014) DOSY-NMR and Raman investigations on the self-aggregation and cyclodextrin complexation of vanillin. J Phys Chem B 118(25):7147–7155
Fourmentin S, Ciobanu A, Landy D, Wenz G (2013) Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests. Beilstein J Org Chem 9:1185–1191. https://doi.org/10.3762/bjoc.9.133
Gould S, Scott RC (2005) 2-Hydroxypropyl-β-cyclodextrin (HP- β-CD): a toxicology review. Food Chem Toxicol 43(10):1451–1459. https://doi.org/10.1016/j.fct.2005.03.007
Griffin S, Wyllie SG, Markham J (1999) Determination of octanol—water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. J Chromatogr A 864:221–228. https://doi.org/10.1016/S0021-9673(99)01009-2
Hǎdǎrugǎ NG, Hǎdǎrugǎ DI, Isengard HD (2012) Water content of natural cyclodextrins and their essential oil complexes : a comparative study between Karl Fischer titration and thermal methods. Food Chem 132:1741–1748. https://doi.org/10.1016/j.foodchem.2011.11.003
Hernandez-Sanchez P, Lopez-Miranda S, Lucas-Abellan C, Nunez-Delicado E (2012) Complexation of eugenol (EG), as main component of clove oil and as pure compound, with β- and HP-β-CDs. Food Nutr Sci 3:716–723. https://doi.org/10.4236/fns.2012.36097
Hernández-Sánchez P, López-Miranda S, Guardiola L, Serrano-Martínez A, Gabaldón JA, Nuñez-Delicado E (2017) Optimization of a method for preparing solid complexes of essential clove oil with β-cyclodextrins. J Sci Food Agric 97(2):420–426. https://doi.org/10.1002/jsfa.7781
Higuchi T, Connors KA (1965) Phase-solubility techniques. Adv Anal Chem Instrum 4:117–212
Hill LE, Gomes C, Taylor TM (2013) Characterization of beta-cyclodextrin inclusion complexes containing essential oils (trans -cinnamaldehyde, eugenol, cinnamon bark, and clove bud extracts) for antimicrobial delivery applications. Food Sci Technol 51(1):86–93. https://doi.org/10.1016/j.lwt.2012.11.011
Ho BT, Joyce DC, Bhandari BR (2011) Release kinetics of ethylene gas from ethylene–α-cyclodextrin inclusion complexes. Food Chem 129(2):259–266. https://doi.org/10.1016/j.foodchem.2011.04.035
Hyldgaard M, Mygind T, Meyer RL, Debabov D (2012) Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Front Microbiol 3:1–24. https://doi.org/10.3389/fmicb.2012.00012
Jiang S, Li JN, Jiang ZT (2010) Inclusion reactions of β-cyclodextrin and its derivatives with cinnamaldehyde in Cinnamomum loureirii essential oil. Eur Food Res Technol 230(4):543–550. https://doi.org/10.1007/s00217-009-1192-z
Kamimura JA, Santos EH, Hill LE, Gomes CL (2014) Antimicrobial and antioxidant activities of carvacrol microencapsulated in hydroxypropyl-beta-cyclodextrin. Food Sci Technol 57(2):701–709. https://doi.org/10.1016/j.lwt.2014.02.014
Kapetanakou AE, Skandamis PN (2016) Applications of active packaging for increasing microbial stability in foods: natural volatile antimicrobial compounds. Curr Opin Food Sci 12:1–12. https://doi.org/10.1016/j.cofs.2016.06.001
Karapinar M, Aktuǧ SE (1987) Inhibition of foodborne pathogens by thymol, eugenol, menthol and anethole. Int J Food Microbiol 4(2):161–166. https://doi.org/10.1016/0168-1605(87)90023-7
Kfoury M, Landy D, Auezova L, Greige-Gerges H, Fourmentin S (2014a) Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity. Beilstein J Org Chem 10:2322–2331. https://doi.org/10.3762/bjoc.10.241
Kfoury M, Auezova L, Greige-Gerges H, Ruellan S, Fourmentin S (2014b) Cyclodextrin, an efficient tool for trans-anethole encapsulation: chromatographic, spectroscopic, thermal and structural studies. Food Chem 164:454–461. https://doi.org/10.1016/j.foodchem.2014.05.052
Kfoury M, Auezova L, Fourmentin S, Greige-Gerges H (2014c) Investigation of monoterpenes complexation with hydroxypropyl-beta-cyclodextrin. J Incl Phenom Macrocycl Chem 80:51–60. https://doi.org/10.1007/s10847-014-0385-7
Kfoury M, Balan R, Landy D, Nistor D, Fourmentin S (2015a) Investigation of the complexation of essential oil components with cyclodextrins. Supramol Chem 27(9):1–10. https://doi.org/10.1080/10610278.2015.1051977
Kfoury M, Auezova L, Ruellan S, Greige-Gerges H, Fourmentin S (2015b) Complexation of estragole as pure compound and as main component of basil and tarragon essential oils with cyclodextrins. Carbohydr Polym 118:156–164. https://doi.org/10.1016/j.carbpol.2014.10.073
Kfoury M, Auezova L, Greige-Gerges H, Fourmentin S (2015c) Promising applications of cyclodextrins in food: improvement of essential oils retention, controlled release and antiradical activity. Carbohydr Polym 131:264–272. https://doi.org/10.1016/j.carbpol.2015.06.014
Kfoury M, Lounès-Hadj Sahraoui A, Bourdon N, Laruelle F, Fontaine J, Auezova L, Greige-Gerges H, Fourmentin S (2016a) Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins. Food Chem 196:518–525. https://doi.org/10.1016/j.foodchem.2015.09.078
Kfoury M, Borgie M, Verdin A, Ledoux F, Courcot D, Auezova L, Fourmentin S (2016b) Essential oil components decrease pulmonary and hepatic cells inflammation induced by air pollution particulate matter. Environ Chem Lett 14:345–351. https://doi.org/10.1007/s10311-016-0572-4
Kfoury M, Hadaruga NG, Hadaruga DI, Fourmentin S (2016c) Cyclodextrins as encapsulation material for flavors and aroma. A volume in nanotechnology in the agri-food industry. ISBN: 978-0-12-804307-3
Kfoury M, Landy D, Ruellan S, Auezova L, Greige-Gerges H, Fourmentin S (2016d) Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol. Beilstein J Org Chem 12(12):29–42. https://doi.org/10.3762/bjoc.12.5
Kfoury M, Landy D, Ruellan S, Auezova L, Greige-gerges H, Fourmentin S (2016e) Nootkatone encapsulation by cyclodextrins : effect on water solubility and photostability. Food Chem 236:41–48. https://doi.org/10.1016/j.foodchem.2016.12.086
Kfoury M, Auezova L, Greige-Gerges H, Larsen KL, Fourmentin S (2016f) Release studies of trans-anethole from β-cyclodextrin solid inclusion complexes by multiple headspace extraction. Carbohydr Polym 151:1245–1250. https://doi.org/10.1016/j.carbpol.2016.06.079
Kfoury M, Auezova L, Greige-Gerges H, Fourmentin S (2016g) Development of a total organic carbon method for the quantitative determination of solubility enhancement by cyclodextrins : application to essential oils. Anal Chim Acta 918:21–25. https://doi.org/10.1016/j.aca.2016.03.013
Kfoury M, Pipkin JD, Antle V, Fourmentin S (2017) Captisol®: an efficient carrier and solubilizing agent for essential oils and their components. Flavour Fragr J 32(5):340–346. https://doi.org/10.1002/ffj.3395
Kfoury M, Auezova L, Greige-Gerges H, Fourmentin S (2018a) Cyclodextrins for essential oils applications. Fundamentals and applications of cyclodextrins. In: Fourmentin S, Crini G, Lichtfouse E (eds) Environmental chemistry for a sustainable world, vol 1. Springer, Berlin, pp 81–123. https://doi.org/10.1007/978-3-319-76159-6_4
Kfoury M, Landy D, Fourmentin S (2018b) Characterization of cyclodextrin/volatile inclusion complexes: a review. Molecules 23:1204–1226. https://doi.org/10.3390/molecules23051204
Kurkov SV, Loftsson T (2013) Cyclodextrins. Int J Pharm 453(1):167–180. https://doi.org/10.1016/j.ijpharm.2012.06.055
Landy D, Fourmentin S, Salome M, Surpateanu G (2000) Analytical improvement in measuring formation constants of inclusion complexes between β-cyclodextrin and phenolic compounds. J Incl Phenom 38(1–4):187–198. https://doi.org/10.1023/A:1008156110999
Landy D, Tetart F, Truant E, Blach F, Fourmentin S, Surpateanu G (2007) Development of a competitive continuous variation plot for the determination of inclusion compounds stoichiometry. J Incl Phenom Macrocycl Chem 57:409–413. https://doi.org/10.1007/s10847-006-9226-7
Lee JH, Lee J, Song KB (2015) Development of a chicken feet protein film containing essential oils. Food Hydrocoll 46:208–215. https://doi.org/10.1016/j.foodhyd.2014.12.020
Lipinski CA (2000) Drug-like properties and the cause of poor solubility and poor permeability. J Pharmacol Toxicol Methods 44:235–249. https://doi.org/10.1016/S1056-8719(00)00107-6
Lipinski CA (2004) Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov Today Technol 1:337–341. https://doi.org/10.1016/j.ddtec.2004.11.007
Liu L, Guo QX (2002) The driving forces in the inclusion complexation of cyclodextrins. J Incl Phenom Macrocycl Chem 42(1):1–14. https://doi.org/10.1023/A:1014520830813
Loftsson T, Brewster ME (2010) Pharmaceutical applications of cyclodextrins: basic science and product development. J Pharm Pharmacol 62(11):1607–1621. https://doi.org/10.1111/j.2042-7158.2010.01030.x
Loftsson T, Duchêne D (2007) Cyclodextrins and their pharmaceutical applications. Int J Pharm 329:1–11. https://doi.org/10.1016/j.ijpharm.2006.10.044
Lopez-Nicolas JM, Perez-Lopez AJ, Carbonell-Barrachina A, Garcia-Carmona F (2007) Use of natural and modified cyclodextrins as inhibiting agents of peach juice enzymatic browning. J Agric Food Chem 55(13):5312–5319. https://doi.org/10.1021/jf070499h
Lopez-Nicolas JM, Andreu-Sevilla AJ, Carbonell-Barrachina ÁA, García-Carmona F (2009) Effects of addition of α-cyclodextrin on the sensory quality, volatile compounds, and color parameters of fresh pear juice. J Agric Food Chem 57(20):9668–9675. https://doi.org/10.1021/jf901919t
Lopez-Nicolas JM, Rodríguez-Bonilla P, García-Carmona F (2014) Cyclodextrins and antioxidants. Crit Rev Food Sci 54(2):251–276. https://doi.org/10.1080/10408398.2011.582544
Lu Z, Cheng B, Hu Y, Zhang Y, Zou G (2009) Complexation of resveratrol with cyclodextrins: solubility and antioxidant activity. Food Chem 113(1):17–20. https://doi.org/10.1016/j.foodchem.2008.04.042
Lucas-Abellán C, Mercader-Ros MT, Zafrilla MP, Fortea MI, Gabaldon JA, Nunez-Delicado E (2008) ORAC-fluorescein assay to determine the oxygen radical absorbance capacity of resveratrol complexed in cyclodextrins. J Agric Food Chem 56:2254–2259. https://doi.org/10.1021/jf0731088
Marques HMC (2010) A review on cyclodextrin encapsulation of essential oils and volatiles. Flavour Fragr J 25(5):313–326. https://doi.org/10.1002/ffj.2019
Martina K, Binello A, Lawson D, Jicsinszky L, Cravotto G (2013) Recent applications of cyclodextrins as food additives and in food processing. Curr Nutr Food Sci 9(3):167–179. https://doi.org/10.2174/1573401311309030001
Mazzobre MF, dos Santos CI, Buera M (2011) Solubility and stability of β- cyclodextrin-terpineol inclusion complex as affected by water. Food Biophys 6(2):274–280. https://doi.org/10.1007/s11483-011-9208-1
Miguel MG, Dandlen SA, Figueiredo AC, Pedro LG, Barroso JG, Marques MH (2010) Comparative evaluation of the antioxidant activities of thymol and carvacrol and the corresponding β-cyclodextrin complexes. Acta Hort 853:363–368. https://doi.org/10.17660/ActaHortic.2010.853.44
Miller LA, Carrier RL, Ahmed I (2007) Practical considerations in development of solid dosage forms that contain cyclodextrin. J Pharm Sci 96(7):1691–1707. https://doi.org/10.1002/jps.20831
Moreira SM, de Carvalho W, Alexandrino AC, de Paula HCB, Rodrigues MCP, de Figueiredo RW, Maia GA, de Figueiredo EMAT, Brasil IM (2014) Int J Food Sci Technol 49(10):2192–2203. https://doi.org/10.1111/ijfs.12535
Mura P (2014) Analytical techniques for characterization of cyclodextrin complexes in aqueous solution : a review. J Pharm Biomed Anal 101:238–250. https://doi.org/10.1016/j.jpba.2014.02.022
Mura P (2015) Analytical techniques for characterization of cyclodextrin complexes in the solid state : a review. J Pharm Biomed Anal 113:226–238. https://doi.org/10.1016/j.jpba.2015.01.058
Nazzaro F, Fratianni F, Martino LD (2013) Effect of essential oils on pathogenic bacteria. Pharmaceuticals 6(12):1451–1474. https://doi.org/10.3390/ph6121451
Nieddu M, Rassu G, Boatto G, Bosi P, Trevisi P, Giunchedi P, Carta A, Gavini E (2014) Improvement of thymol properties by complexation with cyclodextrins: in vitro and in vivo studies. Carbohydr Polym 102:393–399. https://doi.org/10.1016/j.carbpol.2013.10.084
Numanoglu U, Şen T, Tarimci N, Kartal M, Koo OMY, Önyüksel H (2007) Use of cyclodextrins as a cosmetic delivery system for fragrance materials: linalool and benzyl acetate. AAPS PharmSciTech 8(4):85. https://doi.org/10.1208/pt0804085
Nunez-Delicado E, Sanchez-Ferrer A, Garcia-Carmona F (1997) Cyclodextrins as secondary antioxidants: synergism with ascorbic acid. J Agric Food Chem 45(8):2830–2835. https://doi.org/10.1021/jf9609800
Papajani V, Haloci E, Goci E, Shkreli R, Manfredini S (2015) Evaluation of antifungal activity of Origanum vulgare and Rosmarinus officinalis essential oil before and after inclusion in β-cyclodextrin. Int J Pharm Pharm Sci 7(5):5–8
Pavela R, Benelli G (2016) Essential oils as ecofriendly biopesticides ? Challenges and constraints. Trends Plant Sci 21(12):1000–1007. https://doi.org/10.1016/j.tplants.2016.10.005
Pinho E, Grootveld M, Soares G, Henriques M (2014) Cyclodextrins as encapsulation agents for plant bioactive compounds. Carbohydr Polym 101:121–135. https://doi.org/10.1016/j.carbpol.2013.08.078
Prakash B, Kedia A, Mishra PK, Dubey NK (2015) Plant essential oils as food preservatives to control moulds, mycotoxin contamination and oxidative deterioration of agri-food commodities—potentials and challenges. Food Control 47:381–391. https://doi.org/10.1016/j.foodcont.2014.07.023
Radu CD, Parteni O, Ochiuz L (2016) Applications of cyclodextrins in medical textiles—review. J Control Release 224:146–157. https://doi.org/10.1016/j.jconrel.2015.12.046
Rakmai J, Cheirsilp B, Torrado-agrasar A, Simal Gandara J, Mejuto JC, Torrado-agrasar A (2017) Encapsulation of yarrow essential oil in hydroxypropyl-beta-cyclodextrin: physiochemical characterization and evaluation of bio-efficacies. CyTA Journal of Food. https://doi.org/10.1080/19476337.2017.1286523
Rakshit R (2011) Skin care textiles - A review. Man-Made Textiles in India 39(3):81–85
Rashed AA, Mohd Nawi MN, Sulaiman K (2017) Assessment of essential oil as a potential anti- obesity agent: a narrative review Assessment of essential oil as a potential anti- obesity agent: a narrative review. J Essent Oil Res 29(1):1–10. https://doi.org/10.1080/10412905.2016.1213668
Raut JS, Karuppayil SM (2014) A status review on the medicinal properties of essential oils. Ind Crops Prod 62:250–264. https://doi.org/10.1016/j.indcrop.2014.05.055
Reineccius TA, Reineccius GA, Peppard TL (2004) Utilization of β-cyclodextrin for improved flavor retention in thermally processed foods. J Food Sci 69(1):58–62. https://doi.org/10.1111/j.1365-2621.2004.tb17856.x
Ribeiro-Santos R, Andrade M, Sanches-Silva A (2017) Application of encapsulated essential oils as antimicrobial agents in food packaging. Curr Opin Food Sci 14:78–84. https://doi.org/10.1016/j.cofs.2017.01.012
Sherry M, Charcosset C, Fessi H, Greige-Gerges H (2013) Essential oils encapsulated in liposomes: a review. J Liposome Res 23(4):268–275. https://doi.org/10.3109/08982104.2013.819888
Szejtli J (2003) Cyclodextrins in the textile industry. Starch 55(5):191–196. https://doi.org/10.1002/star.200390050
Szejtli J (2004) Past, present and future of cyclodextrin research. Pure Appl Chem 76:1825–1844
Szejtli J, Szente L (2005) Elimination of bitter, disgusting tastes of drugs and foods by cyclodextrins. Eur J Pharm Biopharm 61(3):115–125. https://doi.org/10.1016/j.ejpb.2005.05.006
Szente L, Szejtli J (2004) Cyclodextrins as food ingredients. Trends Food Sci Technol 15(3–4):137–142. https://doi.org/10.1016/j.tifs.2003.09.019
Tanemura I, Saito Y, Ueda H, Sato T (1998) Solubility method using static head-space gas chromatography for determination of the stability constants of fragrance materials with 2- hydroxypropyl-β-cyclodextrin. Chem Pharm Bull 46(3):540–541
Tao F, Hill LE, Peng Y, Gomes CL (2014) Synthesis and characterization of β-cyclodextrin inclusion complexes of thymol and thyme oil for antimicrobial delivery applications. Food Sci Technol 59(1):247–255. https://doi.org/10.1016/j.lwt.2014.05.037
Tian XN, Jiang ZT, Li R (2008) Inclusion interactions and molecular microcapsule of Salvia sclarea L. essential oil with β-cyclodextrin derivatives. Eur Food Res Technol 227(4):1001–1007. https://doi.org/10.1007/s00217-007-0813-7
Tisserand R, Young R (2014) Essential oil safety. A guide for health care professionals, 2nd edn. Churchill Livingstone, London, pp 23–38
Turek C, Stintzing FC (2013) Stability of essential oils: a review. Compr Rev Food Sci Food Saf 12(1):40–53. https://doi.org/10.1111/1541-4337.12006
Uyar T, Hacaloglu J, Besenbacher F (2009) Reactive & functional polymers electrospun polystyrene fibers containing high temperature stable volatile fragrance/flavor facilitated by cyclodextrin inclusion complexes. React Funct Polym 69(3):145–150. https://doi.org/10.1016/j.reactfunctpolym.2008.12.012
Voncina B, Vivod V (2013) Cyclodextrins in textile finishing. Cyclodextrins in textile finishing. In: Günay M (ed) Textile dyeing. InTech, Tijeka, Chapter 3, p 53 https://doi.org/10.5772/53777
Vraz Kresevic S, Voncina B, Gersak J (2008) Insect resistant and eco-friendly textile materials. In: Dragcevic Zvonko (ed) 4th International textile, clothing & design conference: magic world of textiles: book of proceedings, ITC&DC, 05–08 October, 2008, Faculty of Textile Technology, University of Zagreb, Dubrovnik, Croatia. Zagreb, 2008
Waleczek KJ, Marques HMC, Hempel B, Schmidt PC (2003) Phase solubility studies of pure (–)—α-bisabolol and camomile essential oil with β–cyclodextrin. Eur J Pharm Biopharm 55:247–251. https://doi.org/10.1016/S0939-6411(02)00166-2
Wang J, Cao Y, Sun B, Wang C (2011) Physicochemical and release characterisation of garlic oil-β-cyclodextrin inclusion complexes. Food Chem 127(4):1680–1685. https://doi.org/10.1016/j.foodchem.2011.02.036
Yamamoto C, Neoh TL, Honbou H, Yoshii H, Furuta T (2012) Kinetic analysis and evaluation of controlled release of D-limonene encapsulated in spray-dried cyclodextrin powder under linearly ramped humidity. Drying Technol 30(11–12):1283–1291. https://doi.org/10.1080/07373937.2012.681089
Yang Z, Xiao Z, Ji H (2015) Solid inclusion complex of terpinen-4-ol/β-cyclodextrin: kinetic release, mechanism and its antibacterial activity. Flavour Frag J 30(2):179–187. https://doi.org/10.1002/ffj.3229
Zeng Z, Fang Y, Jin H (2012) Side chain influencing the interaction between β-cyclodextrin and vanillin. Flavour Fragr J 27:378–385. https://doi.org/10.1002/ffj.3115
Acknowledgements
Authors thank Marc Fourmentin from the University of the Littoral Opal Coast (ULCO), France, for the illustrations.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kfoury, M., Auezova, L., Greige-Gerges, H. et al. Encapsulation in cyclodextrins to widen the applications of essential oils. Environ Chem Lett 17, 129–143 (2019). https://doi.org/10.1007/s10311-018-0783-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10311-018-0783-y