Synthesis and Anti Lipid-Peroxidation Activity of Hydroquinone Monoalkyl Ethers

Yasunori NIHRO; Haruhiro FURUKAWA; Satoshi SOGAWA; Tzer Chuan WANG; Hideki MIYATAKA; Hitoshi MATSUMOTO; Tokutaro MIKI; Toshio SATOH

doi:10.1248/cpb.42.576

Yasunori NIHRO, Haruhiro FURUKAWA, Satoshi SOGAWA, Tzer Chuan WANG, Hideki MIYATAKA, Hitoshi MATSUMOTO, Tokutaro MIKI, Toshio SATOH

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Keywords: hydroquinone monoalkyl ether, 4-hexyloxy-2, 3, 6-trimethylphenol, antioxidant, lipid peroxidation

JOURNAL FREE ACCESS

1994 Volume 42 Issue 3 Pages 576-579

DOI https://doi.org/10.1248/cpb.42.576

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Abstract

A series of hydroquinone monoalkyl ethers was synthesized and evaluated for anti lipid-peroxidation activity in rat liver microsomes. 4-Hexyloxy-2, 3, 6-trimethylphenol (9), having a low redox potential, as well as ascorbic acid exhibited the strongest anti lipid-peroxidation activity (IC₅₀=4.2×10^-7M). Structure-activity relationship studies demonstrated that the inhibitory effect of hydroquinone monoalkyl ethers on lipid peroxidation was increased by the acquisition of an optimum hydrophobicity and decreased by an insufficient or excessive hydrophobicity.

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