2-Hydroxypropylated Cyclodextrins as a Sustained-Release Carrier for Fragrance Materials

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The potential use of three kinds of 2-hydroxypropylated cyclodextrins [HP-CyDs : 2-hydroxypropyl-α-cyclodextrin (HP-α-CyD), 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) and 2-hydroxypropyl-γ-cyclodextrin(HP-γ-CyD)] in the solubilizing of fragrance materials and the retarding of their release rates was examined. Of the HP-CyDs, HP-β-CyD significantly increased the solubility of six fragrance materials in water, and the apparent 1 : 1 stability constant of the HP-β-CyD complexes was higher than those of the HP-α-CyD and HP-γ-CyD complexes. Ultraviolet, circular dichroism and unclear magnetic resonance spectroscopic studies suggested that the inclusion mode of eugenol is different between the HP-β-CyD complex and the HP-α- or HP-γ-CyD complexes. The release rates of d-camphor and 3-l-methoxypropane 1,2-diol from water were remarkably decreased by the addition of HP-CyDs, where the rate of decrease was in agreement with that of the stability constant ranking of the complexes, i.e., fragrance materials alone<HP-α-CyD<HP-γ-CyD<HP-β-CyD. In order to retard the transport of fragrance materials to skin, the suppressive effect of HP-CyDs was examined in vitro. The mean transit time for eugenol through the skin barrier increased in the order of eugenol alone<HP-γ-CyD<HP-α-CyD<HP-β-CyD, and the suppressive effects of HP-α-CyD and HP-β-CyD were remarkably greater than that of the nonionic surfactant, HCO-60. The present data suggest that HP-β-CyD has a significant advantage over the other HP-CyDs and HCO-60 with respect to providing high aqueous solubility and the sustained release of fragrance materials while maintaining a lack of toxicity in topical liquid preparations of fragrance materials.
公益社団法人日本薬学会の論文
1996-02-15

2-Hydroxypropylated Cyclodextrins as a Sustained-Release Carrier for Fragrance Materials

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