Grasas y Aceites, Vol 65, No 2 (2014)

Synthesis and antioxidant activity of two novel tetraphenolic compounds derived from toluhydroquinone and tertiary butylhydroquinone

Z. W. Jiang
School of Life Sciences, Shanghai University, China

X. C. Weng
School of Life Sciences, Shanghai University, China

Y. Huang
School of Life Sciences, Shanghai University, China

J. P. Hou
School of Life Sciences, Shanghai University, China

X. Y. Liao
School of Life Sciences, Shanghai University, China


Two novel compounds bearing four hydroxyphenyl groups were synthesized by the acid-catalyzed condensation reaction of glyoxal with toluhydroquinone (THQ) or tertiary butylhydroquinone (TBHQ), respectively. The antioxidant activity of the newly synthesized compounds was assessed by the Rancimat test, a 2,2-diphenyl 1-picrylhydrazyl (DPPH) assay and reducing power assay. In the Rancimat antioxidant test using lard oil as substrate, the performance of two newly synthesized compounds was superior to TBHQ at 140 °C. It was suggested that two newly synthesized compounds can be used to improve the oxidative stability of lipid products during high temperature processing. With regard to the DPPH radical scavenging activity and reducing power, the performance of synthesized compounds was inferior to their mother compounds, respectively. The results show that the DPPH radical scavenging activity and reducing power of a compound did not correlate with its ability to retard lipid oxidation.


Antioxidant activity; Condensation reaction; DPPH; TBHQ; THQ

Full Text:



Bauer RS, Dangayach KCB. 1992. Process for preparing lowchlorine epoxy resi ns. Patent No. US 5098964.

Hamama AA, Nawar WW. 1991. Thermal decomposition of some phenolic antioxidants. J. Agric. Food Chem. 39, 1063–1069.

Huang D, Ou B, Prior RL. 2005. The chemistry behind antioxidant capacity assays. J. Agric. Food Chem. 53, 1841–1856. PMid:15769103

Li JY, Wang T, Wu H, Ho CT, Weng XC. 2006. 1,1-Di- (2,5-dihydroxy-4-tertbutylphenyl)ethane: a novel antioxidant. J. Food Lipids 13, 331–340.

Li SMK. 1992. Process for preparing tetraphenolic compounds. Patent No. US 5146006.

Marmesat S, Morales A, Velasco J, Dobarganes MC. 2010. Action and fate of natural and synthetic antioxidants during frying. Grasas Aceites 61, 333–340.

Molyneux P. 2004. The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J. Sci. Technol. 26, 211–219.

Oyaizu M. 1986. Studies on products of browning reactions: antioxidative activities of products of browning reaction prepared from glucosamine. Jpn. J. Nutr. 44, 307–315.

Proestos C, Boziaris IS, Nychas GJE, Komaitis M. 2006. Analysis of flavonoids and phenolic acids in Greek aromatic plants: Investigation of their antioxidant capacity and antimicrobial activity. Food Chem. 95, 664–671.

Shahidi F, Zhong Y. 2010. Lipid oxidation and imroving the oxidative stability. Chem. Soc. Rev. 39, 4067–4079. PMid:20617249

Shimada K, Fujikawa K, Yahara K, Nakamura T. 1992. Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion. J. Agric. Food Chem. 40, 945–948.

Silva FAM, Borges F, Ferreira MA. 2001. Effects of phenolic propyl esters on the oxidative stability of refined sunflower oil. J. Agric. Food Chem. 49, 3936–3941. PMid:11513692

Tseng YH, Yang JH, Mau JL. 2008. Antioxidant properties of polysaccharides from Ganoderma tsugae. Food Chem. 107, 732–738.

Zhang CX, Wu H, Weng XC. 2004. Two novel synthetic antioxidants for deep frying oils. Food Chem. 84, 219–222.

Copyright (c) 2014 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Contact us

Technical support