Synthesis of L-Ascorbic Acid Derivative Including 3-Aminopropane Phosphoric Acid as a Novel Whitening Agent

Abstract

A stable derivative of L-ascorbic acid, 2-O-[(3-aminopropyl)phosphinooxy]-L-ascorbic acid (LAAP), was synthesized in moderate yield and its chemical stability and effects on melanin synthesis were investigated. L-Ascorbic acid was decomposed completely within about 1 hour, while 93% of LAAP remained even after 10 days. Treatment of L-ascorbic acid and LAAP decreased melanin content in normal human melanocytes to 33.8% and 49.1% of control at 2 mM, respectively. Considering chemical instability of L-ascorbic acid, LAAP is a much better whitening agent.