Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties

Kuniyoshi Shimizu, Ryuichiro Kondo, Kokki Sakai, Norio Takeda, Tetsuji Nagahata, Takayuki Oniki

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59 Citations (Scopus)


A novel vitamin E derivative, (6″-hydroxy-2″,5″, 7″,8″tetramethylchroman-2″-yl)methyl 3-(2′,4′-dihydroxyphenyl)propionate (TM4R), which has a chromanoxyl ring and 4-substituted resorcinol moieties, was synthesized; and its inhibitory effects on tyrosinase, antioxidant ability, and lightening effect of ultraviolet B (UVB)-induced hyperpigmentation were estimated. TM4R showed potent inhibitory activity on tyrosinase, which is the rate-limiting enzyme in melanogenesis. The scavenging activities of TM4R on 1, 1-diphenyl-2-picrylhydrazyl and hydroxyl radicals were found to be nearly the same as those of α-tocopherol. Furthermore, an efficient lightening effect was observed following topical application of TM4R to UVB-stimulated hyperpigmented dorsal skin of brownish guinea pigs. These results suggest that TM4R may be a candidate for an efficient whitening agent, possibly by inhibiting tyrosinase activity and biological reactions caused by reactive oxygen species.

Original languageEnglish
Pages (from-to)1321-1326
Number of pages6
Issue number12
Publication statusPublished - Jan 1 2001


All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Cell Biology

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