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4‐(1‐Phenylethyl)1,3‐Benzenediol: A New, Highly Efficient Lightening Agent
Author(s) -
Vielhaber G.,
Schmaus G.,
Jacobs K.,
Franke H.,
Lange S.,
Herrmann M.,
Joppe H.,
Koch O.
Publication year - 2007
Publication title -
international journal of cosmetic science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.532
H-Index - 62
eISSN - 1468-2494
pISSN - 0142-5463
DOI - 10.1111/j.1467-2494.2007.00355_6.x
Subject(s) - kojic acid , chemistry , tyrosinase , mtt assay , melanin , cytotoxicity , stereochemistry , in vitro , biochemistry , enzyme
There is an increasing world‐wide demand for skin lightening active ingredients. Many common lightening ingredients on the market are either unsafe or ineffective at low concentrations. We therefore screened a series of hydroxy‐stilbene derivatives for tyrosinase inhibitory activity. By chemical synthesis, the structures were optimized for efficacy and stability. The final candidate, 4‐(1‐phenylethyl)1,3‐benzenediol, was found to be stable and to inhibit mushroom tyrosinase 22 times more effectively than kojic acid. In an assay with B16V melanoma cells, 4‐(1‐phenylethyl)1,3‐benzenediol was the most potent inhibitor of melanin synthesis with an IC 50 of 2 μM among the compounds investigated. The lightening effect of 4‐(1‐phenylethyl)1,3‐benzenediol was not due to cytotoxicity as proved by an MTT assay on B16V cells. On pigmented 3D epidermis models, 0.1% of 4‐(1‐phenylethyl)1,3‐benzenediol led to an almost complete suppression of melanin synthesis after 14 days of incubation. Finally, an in vivo test on Asian subjects proved that 4‐(1‐phenylethyl)1,3‐benzenediol efficiently lightens human skin at 0.5% dosage. Optimal results are achieved when 4‐(1‐phenylethyl)1,3‐benzenediol is applied in formulations with low oil content. In summary, we have demonstrated that 4‐(1‐phenylethyl)1,3‐benzenediol is a potent, stable and safe skin lightener.