Use of cyclodextrins as a cosmetic delivery system for fragrance materials: Linalool and benzyl acetate

Abstract

The aim of this study was to increase the stability and water solubility of fragrance materials, to provide controlled release of these compounds, and to convert these substances from liquid to powder form by preparing their inclusion complexes with cyclodextrins (CDs). For this purpose, linalool and benzyl acetate were chosen as the fragrance materials. The use of beta-cyclodextrin (beta CD) and 2-hydroxypropyl-beta-cyclodextrin (2-HP beta CD) for increasing the solubility of these 2 fragrance materials was studied. Linalool and benzyl acetate gave a B-type diagram with beta CD, whereas they gave an A(L)-type diagram with 2-HP beta CD. Therefore, complexes of fragrance materials with 2-HP beta CD at 1:1 and 1:2 molar ratios (guest:host) were prepared. The formation of inclusion complexes was confirmed using proton nuclear magnetic resonance ((1)H-NMR) spectroscopy and circular dichroism spectroscopy. The results of the solubility studies showed that preparing the inclusion complex with 2-HP beta CD at a 1:1 molar ratio increased the solubility of linalool 5.9-fold and that of benzyl acetate 4.2-fold, whereas the complexes at a 1:2 molar ratio increased the solubility 6.4- and 4.5-fold for linalool and benzyl acetate, respectively. The stability and in vitro release studies were performed on the gel formulations prepared using uncomplexed fragrance materials or inclusion complexes of fragrance materials at a 1:1 molar ratio. It was observed that the volatility of both fragrance materials was decreased by preparing the inclusion complexes with 2-HP beta CD. Also, in vitro release data indicated that controlled release of fragrances could be possible if inclusion complexes were prepared.

Encapsulation of yarrow essential oil in hydroxypropyl-beta-cyclodextrin: physiochemical characterization and evaluation of bio-efficacies

“…Statistical significance of the results was evaluated by one-way analysis of variance (ANOVA) with Duncan's multiple range tests (p < 0.05) using the Statistical Package for Social Sciences (SPSS) version software 10. Haiyee et al, 2009;Jiang, Tan, Tan, & Li, 2016;Kfoury, Auezova, Fourmentin, & GreigeGerges, 2014;Kfoury et al, 2016;Numanoǧlu et al, 2007;Tao, Hill, Peng, & Gomes, 2014). These components then competed with the major compound for inclusion complex formations with the HPβCD.…”

A review on cyclodextrin encapsulation of essential oils and volatiles

“…insignificant improvement in solubility) and very stable complexes result in a retarded or an incomplete release of the guest and consequently absorption is hindered; using this concept, modified release, especially slow release control, may be reached for drugs [37] and fragrances. [59] However, in some cases, even with small KS values, complexation conferred better physicochemical, pharmaco-technical and biopharmaceutical properties of drugs and/or other molecules.…”

Electrospinning of cyclodextrin/linalool-inclusion complex nanofibers: Fast-dissolving nanofibrous web with prolonged release and antibacterial activity

“…Linalool can form ICs with many CD types a-CD, b-CD, c-CD, HPbCD, and HPcCD (Ciobanu et al, 2012). There are studies dealing with the IC formation with CDs, aiming to overcome the limitations of linalool, including low solubility and stability (Bonetti, de Moraes, Zanin, & de Cássia Bergamasco, 2016;Numanoglu et al, 2007). Fast-dissolving drugs and food supplements became important since they can rapidly disintegrate in the oral cavity without the need of water; in addition they show enhanced solubility and bioavailability.…”