Methyl 3-(2,4-dihydroxyphenyl)propionate is a novel vitamin E derivative that inhibits tyrosinase, which is an antioxidant and inhibits UV-B-induced hyperpigmentation, with potential whitening effects.

Methods: A novel vitamin E derivative, (6"-hydroxy-2",5",7",8"-tetramethylchroman-2"-yl)methyl 3-(2,4-dihydroxyphenyl)propionate (TM4R), which has a chromanoxy ring and a 4-substituted resorcinol moiety, was synthesized and evaluated for its inhibitory activity against tyrosinase, antioxidant capacity, and lightening effect on ultraviolet B (UVB)-induced hyperpigmentation.
Results: Methyl 3-(2,4-dihydroxyphenyl)propionate exhibited potent inhibitory activity against tyrosinase, the rate-limiting enzyme in melanogenesis. The scavenging activity of methyl 3-(2,4-dihydroxyphenyl)propionate against 1,1-diphenyl-2-picrylhydrazyl and hydroxyl radicals was found to be almost the same as that of α-tocopherol. Furthermore, an effective whitening effect was observed after topical application of methyl 3-(2,4-dihydroxyphenyl)propionate on UVB-stimulated pigmented dorsal skin of brown guinea pigs. Conclusion: These Results suggest that methyl 3-(2,4-dihydroxyphenyl)propionate may be an effective skin-whitening agent, possibly by inhibiting tyrosinase activity and biological responses induced by reactive oxygen species.[1]