Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative

A new hybrid, retinyl retinoate 1, was synthesized with a condensing reaction between retinol and retinoic acid to improve the photo-stability, and the in vitro biological activity of the hybrid was analyzed. This retinol derivative had enhanced thermal stability and decreased photosensitivity, and exhibited decreased cell toxicity compared to that of retinol. In addition, RAR activity analysis showed that retinyl retinoate 1 had higher inhibitory activity against c-Jun than retinol and showed superior effects on collagen synthesis compared to retinol. Thus, retinyl retinoate 1 may have the potential to be conveniently used as an additive in cosmetics for prevention and improvement of skin aging and medicines for the treatment of skin troubles due to its excellent stability under severe and accelerated conditions.

Synthesis of the hybrid retinyl retinoate 1 via esterification to form an ester bond between retinol (which has a hydroxyl end group) and retinoic acid (which has a carboxyl end group).Figure optionsDownload as PowerPoint slide