Diglycerides of natural organic acids and phenols were synthesized regio-selectively. Diglycerides are structurally similar to cell membranes and are expected to exhibit cell affinity and permeability. The flexible glycerol linkers allow the diglycerides to exhibit not only the physiological activities of each constituent organic acid but also the synergistic effects, allowing them to be utilized as multifunctional cosmetic raw materials.

Abstract

Biologically active organic acids and natural phenols were combined with a flexible glycerol linker to generate 1,3-diglycerides and 1,2-diglycerides in a regioselective manner. The biological activities of the individual organic acids were still expressed in the glyceride form, with retinoic acid increasing collagen production and kojic acid decreasing melanin production. 1,3-Diglycerides of two different biologically active organic acids were then synthesized to impart their respective biological activities and synergistic effects. Many of them showed excellent wrinkle improvement, whitening, and moisturizing effects, as demonstrated by bioassays for tyrosinase inhibition tests, collagen production tests in human dermal fibroblasts, and hyaluronic acid production tests in human keratinocytes.