Grasas y Aceites, Vol 68, No 3 (2017)

Butylated caffeic acid: An efficient novel antioxidant

G. Shi
School of Life Sciences, Shanghai University 333, China

X. Liao
School of Life Sciences, Shanghai University 333, China

T. M. Olajide
School of Life Sciences, Shanghai University 333, China

J. Liu
School of Life Sciences, Shanghai University 333, China

X. Jiang
School of Life Sciences, Shanghai University 333, China

X. Weng
School of Life Sciences, Shanghai University 333, China


A novel antioxidant, butylated caffeic acid (BCA) was rationally designed by adding a tert-butyl group to caffeic acid, which was synthesized at a high yield (36.2%) from 2-methoxy-4-methylphenol by a four-step reaction including Friedel-Crafts alkylation, bromine oxidation, ether bond hydrolysis and Knoevenagel condensation. Its antioxidant capacity was much stronger than common commercial antioxidant tert-butyl hydroquinone (TBHQ) and its mother compound, caffeic acid, in both rancimat and deep frying tests. When investigated via the DPPH method, the antioxidant capacity of BCA was almost equal to TBHQ, but lower than caffeic acid. BCA could be a potentially strong antioxidant, especially for food processing at high temperatures such as deep frying and baking.


Antioxidant capacity; Butylated caffeic acid; Deep frying

Full Text:



Akoh CC, Min DB. 2008. Food lipids: chemistry, nutrition, and biotechnology: CRC press. PMCid:PMC2695922

Baum B, Perun A. 1962. Antioxidant efficiency versus structure. Polym. Eng. Sci. 2, 250-259.

Cornard JP, Lapouge C. 2006. Absorption spectra of caffeic acid, caffeate and their 1:1 complex with Al (III): density functional theory and time-dependent density functional theory investigations. J. Phys. Chem. A. 110, 7159-7166. PMid:16737266

Chen CW, Ho CT. 1995. Antioxidant properties of polyphenols extracted from green and black teas. J. Food Lipids 2, 35-46.

Emerton V, Choi E. 2008. Essential guide to food additives. Leatherhead Food International, RSC, Cambridge, UK.

Glende EA, Recknagel RO. 1994. 33-Spectrophotometric Detection of Lipid-Conjugated Dienes A2-Tyson, Charles A. In Vitro Toxicity Indicators, Frazier, J. M., Ed. Academic Press, inc., pp. 400-406.

Gülçin ?. 2006. Antioxidant activity of caffeic acid (3, 4-dihydroxycinnamic acid). Toxicology 217, 213-220.

Handbook of Food Analysis, 2nd ed, vol 1. Marcel Dekker, Inc., New York.

Hsieh Y-TL, Regenstein JM. 1992. Storage stability of fish oil, soy oil, and corn oil mayonnaises as measured by various chemical indices. J. Aquat. Food Prod. 1, 97-106.

Hsieh, Y-TL, Regenstein JM. 1991. Factors affecting quality of fish oil mayonnaise. J. Food Sci. 56, 1298-1301.

Huang Y, Jiang Z, Liao X. 2014. Antioxidant activities of two novel synthetic methylbenzenediol derivatives. Czech J. Food Sci. 32, 348-353.

Hwang H-S, Winkler-Moser JK, Bakota EL, Berhow MA, Liu SX. 2013. Antioxidant activity of sesamol in soybean oil under frying conditions. J. Agric. Food Chem. 90, 659-666.

Jeong CH, Jeong HR, Choi GN, Kim DO, Lee UK, Heo HJ. 2011. Neuroprotective and antioxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chinese Med. 6, 25. PMid:21702896 PMCid:PMC3145603

Liu C, Zhao Y, Li X. 2014. Antioxidant capacities and main reducing substance contents in 110 fruits and vegetables eaten in China. Food Nutr Sci. 5, 293.

Paquot C, Hautfenne A. 1987. Standard methods for the analysis of oils, fats, and derivatives. Analytica Chimica Acta, 7th ed, vol 201. Blackwell, Inc., Oxford, pp. 373.

Piang-Siong W, De Caro P, Marvilliers A, Chasseray X. 2017. Contribution of trans-aconitic acid to DPPH scavenging ability in different media. Food Chem. 214, 447-452. PMid:27507497

Rojas M, Brewer M. 2007. Effect of natural antioxidants on oxidative stability of cooked, refrigerated beef and pork. J. Food Sci. 72, 282-288. PMid:17995791

Saiz-Poseu J, Alcón I, Alibés R. 2012. Self-assembly of alkylcatechols on HOPG investigated by scanning tunneling microscopy and molecular dynamics simulations. Cryst. Eng. Comm. 14, 264-271.

Shahidi F, Janitha P, Wanasundara P. 1992. Phenolic antioxidants. Critical Reviews Food Sci. Nutrit. 32, 67-103. PMid:1290586

Silva FA, 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

Van Esch GJ. 1986. Toxicology of tert-butylhydroquinone (TBHQ). Food Chem. Toxicol. 24, 1063-1065.

Wang Q, Yang Y, Li Y, Yu W, Hou ZJ. 2006. An efficient method for the synthesis of lignans. Tetrahedron Lett. 62, 6107- 6112.

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

Zhou LL, Li C, Weng XC. 2016. A novel method for quantitative analysis of acetylacetone and ethyl acetoacetate by fluorine-19 nuclear magnetic spectroscopy. Magn. Reson. 54, 222-226.

Zuta P, Simpson B, Zhao, X, Leclerc L. 2007. The effect of ?-tocopherol on the oxidation of mackerel oil. Food Chem. 100, 800-807.

Copyright (c) 2017 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