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Molecules 2010, 15(3), 1103-1112; doi:10.3390/molecules15031103
Article

Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers

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Received: 4 December 2009; in revised form: 21 February 2010 / Accepted: 21 February 2010 / Published: 26 February 2010
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Abstract: Compoundswith two phenolic OH groups like curcumin possess efficient antioxidant and anti-inflammatory activity. We synthesized p-cresol dimer (2,2'-dihydroxy-5,5'-dimethylbiphenol, 2a) and p-methoxyphenol dimer (2,2'-dihydroxy-5,5'-dimethoxybiphenol, 2b) by ortho-ortho coupling reactions of the parent monomers, p-cresol (1a) and p-methoxyphenol (1b), respectively. Their antioxidant activity was determined using the induction period method, and their cytotoxicity towards RAW 264.7 cells was also investigated using a cell counting kit. The stoichiometric factors n (number of free radicals trapped by one mole of antioxidant moiety) for 2a and 2b were 3 and 2.8, respectively, being greater than those for 1a and 1b. The ratio of the rate constant of inhibition to that of propagation (kinh/kp) for 2a and 2b was similar to that for 2-t-butyl-4-methoxyphenol (BHA), a conventional food antioxidant. The 50% inhibitory dose (ID50) declined in the order 1b > 1a >> 2b > 2a > BHA. The cytotoxicity for 2a and 2b was significantly greater than that for the parent monomers (p < 0.001), but smaller than that for BHA (p < 0.01). Compounds 2a and 2b may be useful as food antioxidants.
Keywords: p-cresol dimer; p-methoxyphenol dimer; antioxidant; cytotoxicity p-cresol dimer; p-methoxyphenol dimer; antioxidant; cytotoxicity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Kadoma, Y.; Murakami, Y.; Ogiwara, T.; Machino, M.; Yokoe, I.; Fujisawa, S. Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers. Molecules 2010, 15, 1103-1112.

AMA Style

Kadoma Y, Murakami Y, Ogiwara T, Machino M, Yokoe I, Fujisawa S. Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers. Molecules. 2010; 15(3):1103-1112.

Chicago/Turabian Style

Kadoma, Yoshinori; Murakami, Yukio; Ogiwara, Takako; Machino, Mamoru; Yokoe, Ichiro; Fujisawa, Seiichiro. 2010. "Radical-Scavenging Activity and Cytotoxicity of p-Methoxyphenol and p-Cresol Dimers." Molecules 15, no. 3: 1103-1112.


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