A simple and convenient procedure for chemoselectively protecting the amino groups of chitosan has been developed to provide N-phthaloyl-chitosan that is indispensable as a soluble N-protected precursor for further controlled modification reactions of chitosan. Although the conventional N-phthaloylation of chitosan in N,N-dimethylformamide was accompanied by partial phthaloylation of the hydroxy groups, the addition of a small amount of hydroxy-containing compounds effectively suppressed the O-phthaloylation. Of some compounds examined, water proved particularly suitable, resulting in the formation of chemoselectively N-phthaloylated chitosan without any appreciable O-phthaloyl groups. The resulting N-phthaloyl-chitosan was found to be crystalline despite the presence of a bulky substituent. A solubility test indicated that N-phthaloyl-chitosan exhibited considerable affinity for organic solvents.
A highly viscous substance was prepared by evaporating an ethanol solution containing two hydrophilic vitamins; vitamin C, and vitamin B6. The viscous substance and physical mixture of the two vitamins were tested using a differential scanning calorimeter and an X-ray diffractometer. The highly viscous substance was found to be a liquid crystal (LC) made of these two hydrophilic vitamins. Determination by proton nuclear magnetic resonance measurement suggested that intramolecular hydrogen bonding in vitamin B6 was eliminated by the LC formation. This LC compound showed high solubility in 1,3-butanediol (almost 87%). Much higher skin permeation of both vitamin C and B6 was also observed from the LC compound than that from the physical mixture. The present LC compound containing vitamin C and vitamin B6 may be useful for pharmaceutical and cosmeceutical applications.
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