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    Drugs solubilization in ascorbyl-decanoate micellar solutions

    Year: 2003

    Journal: Colloids and Surfaces A: Physicochem. Eng. Aspects 212 (2003) 163-173, 20111221

    Authors: Santiago Palma , Ruben Hilario Manzo , Daniel Allemandi , Laura Fratoni , Pierandrea Lo Nostro

    Organizations: a Departamento de Farmacia, Fac. de Ciencias Quimicas, Universidad Nacional de Cordoba, Ciudad Universitaria, 5000 Cordoba, Argentina b Dipartimento di Chimica, Universite di Firenze, via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze, Italy

    Alkanoyl-6-O-ascorbic acid esters are obtained upon esterification of ascorbic acid's primary hydroxyl groups with fatty acids. Being more hydrophobic than vitamin C, they dissolve in lipophilic media, and behave as surfactants in water, where they produce micellar aggregates or spreading monolayers, depending on the side chain length. These amphiphiles keep the same antioxidant activity of vitamin C, and can be used for solubilization and protection of hydrophobic species from oxidative degradation. In this paper we report a study on the micellar aggregates formed by decanoyl-6-O-ascorbic acid in water, through surface tension, conductivity, and solubility experiments, and on its coagels produced at low temperatures, by means of differential scanning calorimetry and scanning electron microscopy. Solubilization of some hydrophobic molecules (phenacetin, danthron, and griseofulvin) in ascorbyl-decanoate (ASC10) micelles confirms that the supramolecular assemblies significantly enhance the solubility of these drugs in the liquid phase.