Synthesis and Characterization of New Ascorbic Derivative: Sodium Isostearyl 2-O-L-Ascorbyl Phosphate

Abstract

A novel alkyl ester of Vitamin C derivative, originated in a stable ascorbate derivative, sodium L-ascorbic acid 2-phosphate (VCP-Na), was chemically synthesized. The thermal stability, surface tension, distribution between organic and water phase, and in vitro skin permeability were evaluated. This monoalkyl ester derivative was identified as sodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-Na) by UV spectra, infrared spectra, mass spectra, and nuclear magnetic resonance spectroscopy. The reaction afforded VCP-IS-Na in a high yield (60%). VCP-IS-Na exhibited satisfactory stability in neutral solution comparable to that of a typical stable derivative, VCP-Na. Increased skin permeability was superior to those of VCP-Na and ascorbic acid (VC). VCP-IS-Na that is susceptible to the enzymatic hydrolysis by tissue esterase and/or phosphatase released VC in the skin tissues. Thus, these characteristics indicate that the novel Vitamin C derivative presented here, VCP-IS-Na, may be effective pro-Vitamin C for skin care application. © 2005, Japan Oil Chemists' Society. All rights reserved.