Butylated methyl caffeate: a novel antioxidant
Keywords:Antioxidant activity, Butylated methyl caffeate, Caffeic acid derivatives, Free radical scavenging, Frying and emulsions
A novel caffeic acid derivative, butylated methyl caffeate (BMC), was synthesized via esterification between butylated caffeic acid (BCA) and methanol. Its antioxidant activity was investigated and compared to TBHQ, caffeic acid (CA), methyl caffeate (MC) and BCA through deep-frying, an oven test in oil-in-water emulsions and DPPH radical scavenging. BMC showed the strongest antioxidant activity among the five antioxidants in emulsions and its antioxidant activity was almost as strong as BCA in frying. Its soybean oil-water partition coefficient was 9.18 due to its ester and tert-butyl groups, far greater than those of MC (4.82), BCA (2.41), CA (0.84) and TBHQ (3.22). This meant that it was much more soluble in the lipid phase than the other four antioxidants in emulsions. The DPPH radical scavenging activity of BMC was near TBHQ, lower than the other three because of its steric hindrance and less functional phenolic hydroxyl groups compared to others when their masses were the same.
Amorati R, Valgimigli L. 2014. Advantages and limitations of common testing methods for antioxidants. Free Radical Res. 49, 633-649. https://doi.org/10.3109/10715762.2014.996146 PMid:25511471
Boilet L, Cornard JP, Lapouge C. 2005. Determination of the chelating site preferentially involved in the complex of lead (II) with caffeic acid: a spectroscopic and structural study. J. Phys. Chem. A 109, 1952-1960. https://doi.org/10.1021/jp047703d PMid:16833529
Catel Y, Aladedunye F, Przybylski R. 2010. Synthesis, radical scavenging activity, protection during storage, and frying by novel antioxidants. J. Agric. Food. Chem. 58, 11081-11089. https://doi.org/10.1021/jf102287h PMid:20923149
Choudhary M, Grover K, Javed, M. 2015. Effect of deep-fat frying on fatty acid composition and iodine value of rice bran oil blends. Proc. Natl. Acad. Sci., India, Sect. B 85, 211-218. https://doi.org/10.1007/s40011-014-0324-9
Cisneros FH, Paredes D, Arana A, Cisneros-Zevallos L. 2014. Chemical composition, oxidative stability and antioxidant capacity of oil extracted from roasted seeds of sacha-inchi (Plukenetia volubilis L.). J. Agric. Food. Chem. 62, 5191-5197. https://doi.org/10.1021/jf500936j PMid:24823227
Cui L, Mcclements DJ, Decker EA. 2015. Impact of phosphatidylethanolamine on the antioxidant activity of α-tocopherol and trolox in bulk oil. J. Agric. Food. Chem. 63, 3288-3294. https://doi.org/10.1021/acs.jafc.5b00243 PMid:25768290
Firestone D. 1998. Official method Cd 8-53. Peroxide Value, in Firestone D (Ed) Official Methods and Recommended Practices of the American Oil Chemists Society 5th ed. American Oil Chemists' Society, Champaign, III.
Garrido J, Gaspar A, Garrido EM, Miri R, Tavakkoli M, Pourali S, Saso L, Borges F, Firuzi O. 2012. Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress. Biochimie 94, 961-967. https://doi.org/10.1016/j.biochi.2011.12.015 PMid:22210493
Gray J. 1978. Measurement of lipid oxidation: A review. J. Am. Oil Chem. Soc. 55, 539-546. https://doi.org/10.1007/BF02668066
Haidasz EA, Van Kessel ATM, Pratt DAA. 2016. A continuous visible light spectrophotometric approach to accurately determine the reactivity of radical-trapping antioxidants. J. Org. Chem. 81, 737-744. https://doi.org/10.1021/acs.joc.5b02183 PMid:26529543
Hammouda IB, Triki M, Matthäus B, Bouaziz M. 2018. A comparative study on formation of polar components, fatty acids and sterols during frying of refined olive pomace oil pure and its blend coconut oil. J. Agric. Food. Chem. 66, 3514-3523. https://doi.org/10.1021/acs.jafc.7b05163 PMid:29526090
Hao DC, Gu XJ, Xiao PG. 2015. Phytochemical and biological research of Salvia medicinal resources, in Hao DC(Ed.) Medicinal Plants. Woodhead Publishing, Cambridge, pp. 587-639. https://doi.org/10.1016/B978-0-08-100085-4.00014-1
Homma R, Suzuki K, Cui L, McClements DJ, Decker EA. 2015. Impact of association colloids on lipid oxidation in triacylglycerols and fatty acid ethyl esters. J. Agric. Food Chem. 63, 10161-10169. https://doi.org/10.1021/acs.jafc.5b03807 PMid:26506263
Huang Y, Jiang ZW, Liao XY, Hou JP, Weng XC. 2014. Antioxidant activities of two novel synthetic methylbenzenediol derivatives. Czech. J. Food Sci. 32, 348-353. https://doi.org/10.17221/283/2013-CJFS
Jia HC, Shin JA, Lee KT. 2015. Effects of caffeic acid phenethyl ester and 4-Vinylcatechol on the stabilities of oil-in-water emulsions of stripped soybean oil. J. Agric. Food. Chem. 63, 10280−10286. https://doi.org/10.1021/acs.jafc.5b02423 PMid:26492097
Karadag A, Ozcelik B, Saner S. 2009. Review of methods to determine antioxidant capacities. Food Anal. Meth. 2, 41-60. https://doi.org/10.1007/s12161-008-9067-7
Kiralan SS, Dogu-Baykut E, Kittipongpittaya K, Mcclements DJ, Decker EA. 2014. Increased antioxidant efficacy of tocopherols by surfactant solubilization in oil-in-water emulsions. J. Agric. Food. Chem. 62, 10561-10566. https://doi.org/10.1021/jf503115j PMid:25299347
Lisete-Torres P, Losada-Barreiro S, Albuquerque H, Sánchez- Paz V, Paiva-Martins F, Bravo-Díaz C. 2012. Distribution of hydroxytyrosol and hydroxytyrosol acetate in olive oil emulsions and their antioxidant efficiency. J. Agric. Food. Chem. 60, 7318-7325. https://doi.org/10.1021/jf301998s PMid:22720906
Liu SC, Lin JT, Hu CC, Shen BY, Chen TY, Chang YL, Shih CH, Yang DJ. 2017. Phenolic compositions and antioxidant attributes of leaves and stems from three inbred varieties of Lycium chinense Miller harvested at various times. Food Chem. 215, 284-291. https://doi.org/10.1016/j.foodchem.2016.06.072 PMid:27542477
Masuda T, Yamada K, Akiyama J, Someya T, Odaka Y, Takeda Y, Tori M, Nakashima K, Maeka-wa T, Sone Y. 2008. Antioxidation mechanism studies of caffeic acid: identification of antioxidation products of methyl caffeate from lipid oxidation. J. Agric. Food. Chem. 56, 5947-5952. https://doi.org/10.1021/jf800781b PMid:18558705
Mcclements DJ, Decker EA. 2000. Lipid oxidation in oil-in-water emulsions: impact of molecular environment on chemical reactions in heterogeneous food systems. J. Food Sci. 65, 1270-1282. https://doi.org/10.1111/j.1365-2621.2000.tb10596.x
Moon J, Terao J. 1998. Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food. Chem. 46, 5062-5065. https://doi.org/10.1021/jf9805799
Okubanjo SS, Loveday MS, Ye A, Wilde JP, Singh H. 2019. Droplet-stabilized oil-in-water emulsions protect unsaturated lipids from oxidation. J. Agric. Food Chem. 67, 2626-2636. https://doi.org/10.1021/acs.jafc.8b02871 PMid:30608676
Oreopoulou V, Krokida M, Marinos-Kouris D. 2006. Frying of foods, in Mujumdar AS (Ed) Handbook of industrial drying. CRC Press, Boca Raton, pp. 1204-1223. https://doi.org/10.1201/9781420017618.ch52
Paquot C. 1979. Standard methods for the analysis of oils, fats and derivatives. 6th Ed. Pergamon Press, Oxford UK. https://doi.org/10.1016/B978-0-08-022379-7.50009-7
Pekkarinen SS, Stockmann H, Schwarz K, Heinonen IM, Hopia AI. 1999. Antioxidant activity and partitioning of phenolic acids in bulk and emulsified methyl linoleate. J. Agric. Food. Chem. 47, 3036-3043. https://doi.org/10.1021/jf9813236 PMid:10552604
Phonsatta N, Deetae P, Luangpituksa P, Grajeda-Iglesias C, Figueroa-Espinoza MC, Le Comte J, Villeneuve P, Decker EA, Visessanguan W, Panya A. 2017. Comparison of antioxidant evaluation assays for investigating antioxidative activity of gallic acid and its alkyl esters in different food matrices. J. Agric. Food Chem. 65, 7509-7518. https://doi.org/10.1021/acs.jafc.7b02503 PMid:28750167
Samdani GK, Mcclements DJ, Decker EA. 2018. Impact of phospholipids and tocopherols on the oxidative stability of soybean oil-in-water emulsions. J. Agric. Food. Chem. 66, 3939-3948. https://doi.org/10.1021/acs.jafc.8b00677 PMid:29629560
Sanchez-Moreno C, Larrauri JA, Saura-Calixto F. 1998. A procedure to measure the anti-radical efficiency of polyphenols. J. Sci. Food Agric. 76, 270-276. https://doi.org/10.1002/(SICI)1097-0010(199802)76:2<270::AID-JSFA945>3.0.CO;2-9
Shi GS, Liao XY, Olajide TM, Liu JJ, Jiang XY, Weng XC. 2017. Butylated caffeic acid: an efficient novel antioxidant. Grasas Aceites 68, e201. https://doi.org/10.3989/gya.1278162
Sinadinovic-Fiser S, Jankovic M. 2007. Prediction of the partition coefficient for acetic acid in a two-phase system soybean oil-water. J. Am. Oil Chem. Soc. 84, 669-674. https://doi.org/10.1007/s11746-007-1079-8
SoRensen ADM, Durand E, Laguerre M, Bayrasy C, Lecomte J, Villeneuve P, Jacobsen C. 2014. Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates. J. Agric. Food Chem., 62, 12553-12562. https://doi.org/10.1021/jf500588s PMid:25457614
Yue X, Zhu W, Ma S, Yu S, Wang J, Wang YR, Zhang DH, Wang JL. 2016. Highly sensitive and selective determination of tertiary butylhydroquinone in edible oils by competitive reaction induced "on-off-on" fluorescent switch. J. Agric. Food Chem. 64, 706-713. https://doi.org/10.1021/acs.jafc.5b05340 PMid:26746696
How to Cite
Copyright (c) 2020 Consejo Superior de Investigaciones Científicas (CSIC)
This work is licensed under a Creative Commons Attribution 4.0 International License.© CSIC. Manuscripts published in both the printed and online versions of this Journal are the property of Consejo Superior de Investigaciones Científicas, and quoting this source is a requirement for any partial or full reproduction.
All contents of this electronic edition, except where otherwise noted, are distributed under a “Creative Commons Attribution 4.0 International” (CC BY 4.0) License. You may read here the basic information and the legal text of the license. The indication of the CC BY 4.0 License must be expressly stated in this way when necessary.
Self-archiving in repositories, personal webpages or similar, of any version other than the published by the Editor, is not allowed.