Captisol®: an efficient carrier and solubilizing agent for essential oils and their components

Abstract

Essential oils (EOs) and their individual components have several biological properties and are used in cosmetics, food and pharmaceutical industries. However, their application still presents a challenge owing mainly to their volatility and their poor aqueous solubility and stability. The aim of this study was to evaluate, for the first time, the ability of Captisol® (sulfobutylether-β-cyclodextrin, SBE-β-CD) and Captisol-G® (sulfobutylether-γ-cyclodextrin, SBE-γ-CD) to encapsulate the main volatile components of six essential oils (EOs), to enhance the aqueous solubility of these EOs and to generate controlled release systems. The performance of these CDs was compared to hydroxypropyl-β-cyclodextrin (HP-β-CD) and γ-cyclodextrin (γ-CD), respectively. The most common native CDs are α-, β-and γ-CDs and are made up of six, seven and eight glucosyl units, respectively (Figure 1).Incorporating EOs as inclusion complexes in cosmetic, food or pharmaceutical formulations present several advantages. CDs might enhance the solubility of EOs and their components thus higher concentrations could be used, 8,9 produce easy measurable dosage forms, facilitate their dispersion and protect them from interactions --------------------------------------------------------------------------------------------------------------------------------This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review

“…This is for example the case of essential oils. Kfoury et al successfully applied this method for the determination of the K f values of aroma compounds with different CD in a wide variety of essential oils [ 9 , 52 ]. Table 2 represents the data collected from the literature on the determination of K f values using SH-GC.…”

“… CD: cyclodextrin; CRYSMEB: low methylated-β-cyclodextrin; RAMEB: randomly methylated-β-cyclodextrin; HP-β-CD: 2-hydroxypropyl-β-cyclodextrin; SBE-β-CD: sulfobutylether-β-cyclodextrin. a [ 2 ], b [ 45 ], c [ 53 ], d [ 51 ], e [ 54 ], f [ 55 ], g [ 43 ], h [ 49 ], i [ 56 ], j [ 57 ], k [ 44 ], l [ 58 ], m [ 47 ], n [ 50 ], o [ 17 ], p [ 52 ], q [ 49 ], r [ 59 ], s [ 60 ]. …”

pH‐activated polymeric profragrances for dual‐controllable perfume release

“…However, such precursor strategy is significantly limited by unreliable controllability, inadequate reproducibility, and inefficient release. Current research studies mainly stress on direct physical encapsulation to construct nanoscale profragrances with nanocarriers involving polymers, 8‐16 macromolecules, 17,18 inorganic materials, 19,20 and other functional nanocarriers 21‐25 . With the assistance of these nanocapsules, profragrances behave more temperate scent and prolonged retention effect than free fragrances.…”

Interactions between Bio-Based Compounds and Cyclodextrins

“…Also from group II, surface tension has also been used to follow the effect of CDs on the aggregation and interfacial properties of surfactants in CD-surfactant-containing solutions [74] Phase solubility studies Cabreuva essential oil + HP-β-CD [74] Phase solubility studies β-caryophyllene + HP-β-CD [76] UV-vis Black pepper essential oil + HP-β-CD [76] Phase solubility studies CDs 1 + PPs 2 [77] Phase solubility studies, NMR, TGA, DSC β-CD + estragole [78] NMR β-CD + eugenol [27] NMR β-CD + rosmarinic acid [75] NMR Cyclohexylacetic acid + β-CD Phase solubility studies, NMR, HPLC Polymethoxyflavones + HP-β-CD [93] GC, total organic carbon, phase-solubility studies SBE-β-CD, SBE-γ-CD and HP-β-CD + EOS 6 [94,95] 1 CDs: alpha-cyclodextrin (α-CD), beta-cyclodextrin (β-CD), gamma-cyclodextrin (γ-CD), 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), randomly methylated-beta-cyclodextrins (RAMEB), low methylated beta-cyclodextrin (CRYSMEB), and sulfobutylether β-cyclodextrin (SBE-β-CD) 2 PPs: trans-anethole, estragole, eugenol, isoeugenol (phenylpropenes), caffeic acid, p-coumaric acid, and ferulic acid (hydroxycinnamic acids) 3 UAS: ultrasonic attenuation spectroscopy APGs: glucopyranosides (octyl G8, decyl G10, dodecyl G12, tetradecyl G14) and two maltosides (decyl M10, dodecyl M12) 5 EOs: essential oils of cedarwood, clove, eucalyptus, and peppermint 6 EOS: essential oils of Artemisia dracunculus, Citrus reticulata Blanco, Citrus aurantifolia, Melaleuca alternifolia, Melaleuca quinquenervia, and Rosmarinus officinalis cineoliferum Table 2. Compilation of the most relevant techniques used to study the interactions between CDs and bio-based compounds.…”

“…On the other hand, phase-solubility profiles for the encapsulation of polymethoxyflavones, obtained from mandarin EO, into HP-β-CD were obtained by using HPLC [93]. Kfoury et al have used gas chromatography to study the ability of sulfobutylether-β-and sulfobutylether-γ-CD to encapsulate EOs components, such as limonene, estragole, and α-and β-pinene; their solubility in water was improved more than one order of magnitude [94]. It is worth noticing that, recently, a technique based on the total organic carbon determination has been reported and validated to follow the solubility improvement of EOs when increasing the concentration of CD [95].…”