Inclusion Complexation of p-Hydroxybenzoic Acid Esters with 2-Hydroxypropyl-β-cyclodextrins. On Changes in Solubility and Antimicrobial Activity

概要

論文の詳細を見る
To obtain a transparent and effective solution of p-hydroxybenzoic acid esters (parabens), the use of 2-hydroxypropyl-β-cyclodextrins (2-HP-β-CyDs) as solubilizers with different degrees of substitution (D.S.) was surveyed. 2-HP-β-CyDs significantly increased the aqueous solubility of four kinds of parabens (methyl<ethyl<propyl<butyl esters), where the solubilizing ability decreased with an increase in the D.S. of the 2-hydroxypropyl group in β-CyD. The antimicrobial activity of the parabens tended to decrease by complexation with 2-HP-β-CyDs. However, the activity could be maintained by lengthening the alkyl chain of the parabens. ^1H-and ^<13>C-nuclear magnetic resonance and circular dichroism spectroscopic studies suggest that the hydrophobic alkyl moiety of butyl paraben is preferably included in the cavity, and the phenol group extrudes from the cavity. The present results suggest that a suitable combination of 2-HP-β-CyDs and hydrophobic, longer alkyl parabens is useful for the preservation of liquid formulations.
公益社団法人日本薬学会の論文
1993-08-15