Butylated caffeic acid: An efficient novel antioxidant

Authors

DOI:

https://doi.org/10.3989/gya.1278162

Keywords:

Antioxidant capacity, Butylated caffeic acid, Deep frying

Abstract


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.

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References

Akoh CC, Min DB. 2008. Food lipids: chemistry, nutrition, and biotechnology: CRC press. https://doi.org/10.1201/9781420046649 PMCid:PMC2695922

Baum B, Perun A. 1962. Antioxidant efficiency versus structure. Polym. Eng. Sci. 2, 250-259. https://doi.org/10.1002/pen.760020314

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. https://doi.org/10.1021/jp060147y PMid:16737266

Chen CW, Ho CT. 1995. Antioxidant properties of polyphenols extracted from green and black teas. J. Food Lipids 2, 35-46. https://doi.org/10.1111/j.1745-4522.1995.tb00028.x

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. https://doi.org/10.1300/J030v01n01_10

Hsieh, Y-TL, Regenstein JM. 1991. Factors affecting quality of fish oil mayonnaise. J. Food Sci. 56, 1298-1301. https://doi.org/10.1111/j.1365-2621.1991.tb04757.x

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. https://doi.org/10.1007/s11746-013-2204-5

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. https://doi.org/10.1186/1749-8546-6-25 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. https://doi.org/10.4236/fns.2014.54036

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. https://doi.org/10.1016/j.foodchem.2016.07.083 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. https://doi.org/10.1111/j.1750-3841.2007.00335.x 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. https://doi.org/10.1039/C1CE06010D

Shahidi F, Janitha P, Wanasundara P. 1992. Phenolic antioxidants. Critical Reviews Food Sci. Nutrit. 32, 67-103. https://doi.org/10.1080/10408399209527581 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. https://doi.org/10.1021/jf010193p PMid:11513692

Van Esch GJ. 1986. Toxicology of tert-butylhydroquinone (TBHQ). Food Chem. Toxicol. 24, 1063-1065. https://doi.org/10.1016/0278-6915(86)90289-9

Wang Q, Yang Y, Li Y, Yu W, Hou ZJ. 2006. An efficient method for the synthesis of lignans. Tetrahedron Lett. 62, 6107- 6112. https://doi.org/10.1016/j.tet.2006.03.111

Zhang CX, Wu H, Weng XC. 2004. Two novel synthetic antioxidants for deep frying oils. Food Chem. 84, 219-222. https://doi.org/10.1016/S0308-8146(03)00205-X

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. https://doi.org/10.1002/mrc.4369

Zuta P, Simpson B, Zhao, X, Leclerc L. 2007. The effect of ?-tocopherol on the oxidation of mackerel oil. Food Chem. 100, 800-807. https://doi.org/10.1016/j.foodchem.2005.11.003

Published

2017-09-30

How to Cite

1.
Shi G, Liao X, Olajide TM, Liu J, Jiang X, Weng X. Butylated caffeic acid: An efficient novel antioxidant. Grasas aceites [Internet]. 2017Sep.30 [cited 2024Mar.19];68(3):e201. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1668

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Research

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