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Improving the Aqueous Solubility of Triclosan by Solubilization, Complexation, and in Situ Salt Formation

Improving the Aqueous Solubility of Triclosan by Solubilization, Complexation, and in Situ Salt Formation

Christine Grove, Wilna Liebenberg, Jan L du Preez, Wenzhan Yang, Melgardt M de Villiers

J Cosmet Sci. Nov-Dec 2003;54(6):537-50.

PMID: 14730370

Abstract:

Triclosan, an antimicrobial, although widely incorporated into many skin care products, toothpastes, and liquid soaps, presents formulation difficulties because it is practically insoluble in water. The objective of this study was to improve the aqueous solubility of triclosan through solubilization, complexation, and salt formation. The solubility of triclosan in distilled water and in phosphate buffers (pH 7.4) was determined at 30 degrees C. The order of solubilizing performance of the solubilizers was: N-methylglucamine> or =L-arginine>sodium lauryl sulfate>beta-cyclodextrin> or =hydroxypropyl-beta-cyclodextrin>ethanolamine>sodium benzoate>sodium methyl 4-hydroxybenzoate>triethanolamine> or =diethanolamine. These solubilizers increased the solubility of triclosan from 80- to 6000-fold. Micellar solubilization and the formation of either salts or complexes are postulated as possible mechanisms for the increase in the solubility of triclosan by the surfactant sodium lauryl sulphate, the cyclic sugar derivatives beta-cyclodextrin and 2-hydropropyl-beta-cyclodextrin, the amino acid L-arginine, and the amino sugar alcohol N-methylglucamine. Furthermore, although the bacteriostatic efficacy of triclosan was significantly increased when solubilized with N-methylglucamine, L-arginine, and ethanolamine, increased solubilization did not increase the effectiveness of triclosan for all solubilizers tested.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP199684612	β-Cyclodextrin phosphate sodium salt		199684-61-2	Price

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