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International Journal of Food Properties Volume 5, 2002 - Issue 2
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Original Articles

THE ANTIOXIDANT ETHOXYQUIN AND ITS ANALOGUES: A REVIEW

Adrianus J. de Koning CSIR, Division of Food, Biological, and Chemical Technologies, FST Programme (incorporating FIRI), 15 Lower Hope Road, Rosebank, Cape Town, 7700, South Africa
Pages 451-461 | Received 10 Jul 2001, Accepted 10 Oct 2001, Published online: 06 Feb 2007

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Huijuan Jia, Huifeng Ren, Chuanzong Deng, Hisanori Kato & Hideaki Endo. (2012) Effects of Chinese Parsley (Coriandrum sativum) On Oxidative Stabilities of Diet During Storage as Compared with a Synthetic Antioxidant. International Journal of Food Properties 15:6, pages 1394-1407.
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A. Błaszczyk & J. Skolimowski. (2007) Evaluation of the genotoxic and antioxidant effects of two novel feed additives (ethoxyquin complexes with flavonoids) by the comet assay and micronucleus test. Food Additives & Contaminants 24:6, pages 553-560.
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Matthias Schreiner. (2006) Optimization of Solvent Extraction and Direct Transmethylation Methods for the Analysis of Egg Yolk Lipids. International Journal of Food Properties 9:3, pages 573-581.
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Tomonori Tadokoro, Masataka Ikeda, Ko Abe, Tomomi Ide, Hiroko Deguchi Miyamoto, Shun Furusawa, Kosei Ishimaru, Masatsugu Watanabe, Akihito Ishikita, Shouji Matsushima, Tomoko Koumura, Ken-ichi Yamada, Hirotaka Imai & Hiroyuki Tsutsui. (2022) Ethoxyquin is a Competent Radical-Trapping Antioxidant for Preventing Ferroptosis in Doxorubicin Cardiotoxicity. Journal of Cardiovascular Pharmacology 80:5, pages 690-699.
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Giovanni M. Turchini, David S. Francis, Zhen-Yu Du, Rolf E. Olsen, Einar Ringø & Douglas R. Tocher. 2022. Fish Nutrition. Fish Nutrition 303 467 .
Wei Zhao, Jiaolong Li, Tong Xing, Lin Zhang & Feng Gao. (2021) Effects of guanidinoacetic acid and complex antioxidant supplementation on growth performance, meat quality, and antioxidant function of broiler chickens. Journal of the Science of Food and Agriculture 101:9, pages 3961-3968.
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T.S. Guldberg, M. Sandrød, J.B. Øiaas, T. Holten, K. Zahlsen & H.F. Kvitvang. (2021) Analysis of synthetic antioxidants in salmon silage using QuEChERS extraction method followed by determination by LC-MS/MS; a single-laboratory validation study. Journal of Chromatography B 1174, pages 122715.
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Asier Carral-Menoyo, Nuria Sotomayor & Esther Lete. (2020) Palladium-catalysed Heck-type alkenylation reactions in the synthesis of quinolines. Mechanistic insights and recent applications. Catalysis Science & Technology 10:16, pages 5345-5361.
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Abraham Pucheta, Aarón Mendieta, Damián A. Madrigal, Roberto I. Hernández-Benitez, Liseth Romero, Leticia Garduño-Siciliano, Catalina Rugerio-Escalona, María C. Cruz-López, Fabiola Jiménez, Alejandra Ramírez-Villalva, Aydeé Fuentes-Benites, Carlos González-Romero, Omar Gómez-García, Julio López, Miguel A. Vázquez, Blanca Rosales-Acosta, Lourdes Villa-Tanaca, Alfonso Sequeda-Juárez, Eva Ramón-Gallegos, Germán Chamorro-Cevallos, Francisco Delgado & Joaquín Tamariz. (2020) Synthesis and biological activity of fibrate-based acyl- and alkyl-phenoxyacetic methyl esters and 1,2-dihydroquinolines. Medicinal Chemistry Research 29:3, pages 459-478.
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Andreas Kranawetvogl & Paul W. Elsinghorst. (2019) Determination of the Synthetic Antioxidant Ethoxyquin and Its Metabolites in Fish and Fishery Products Using Liquid Chromatography–Fluorescence Detection and Stable-Isotope Dilution Analysis–Liquid Chromatography–Tandem Mass Spectrometry. Journal of Agricultural and Food Chemistry 67:23, pages 6650-6657.
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HuaTao Li, SiYi Tang, WenHao Du, Jun Jiang, PeiYuan Peng, Ping Yuan, YiHong Liao, Jiao Long & SiShun Zhou. (2018) The effects of ethoxyquin and Angelica sinensis extracts on lipid oxidation in fish feeds and growth, digestive and absorptive capacities and antioxidant status in juvenile red carp (Cyprinus carpio var. xingguonensis): a comparative study. Fish Physiology and Biochemistry 45:1, pages 43-61.
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Annette Bernhard, Josef D. Rasinger, Monica B. Betancor, Maria José Caballero, Marc H. G. Berntssen, Anne-Katrine Lundebye & Robin Ørnsrud. (2019) Tolerance and dose-response assessment of subchronic dietary ethoxyquin exposure in Atlantic salmon (Salmo salar L.). PLOS ONE 14:1, pages e0211128.
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A.C. Fanatico, K. Arsi, I. Upadhyaya, J. Morales Ramos, D. Donoghue & A.M. Donoghue. (2018) Sustainable Fish and Invertebrate Meals for Methionine and Protein Feeds in Organic Poultry Production. Journal of Applied Poultry Research 27:4, pages 437-448.
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Annette Bernhard, Josef D. Rasinger, Helene Wisløff, Øyvor Kolbjørnsen, Lene Secher Myrmel, Marc H.G. Berntssen, Anne-Katrine Lundebye, Robin Ørnsrud & Lise Madsen. (2018) Subchronic dietary exposure to ethoxyquin dimer induces microvesicular steatosis in male BALB/c mice. Food and Chemical Toxicology 118, pages 608-625.
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Mohammad Aklakur. (2018) Natural antioxidants from sea: a potential industrial perspective in aquafeed formulation. Reviews in Aquaculture 10:2, pages 385-399.
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R. Rodríguez-Gómez, Marie Vandeput, A. Zafra-Gómez & Jean-Michel Kauffmann. (2018) Liquid chromatography-electrochemical detection for the determination of ethoxyquin and its dimer in pear skin and salmon samples. Talanta 177, pages 157-162.
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Noelia Negreira, Jorge Regueiro, Stig Valdersnes, Marc H.G. Berntssen & Robin Ørnsrud. (2017) Comprehensive characterization of ethoxyquin transformation products in fish feed by traveling-wave ion mobility spectrometry coupled to quadrupole time-of-flight mass spectrometry. Analytica Chimica Acta 965, pages 72-82.
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Ivana Tartaro Bujak, Chryssostomos Chatgilialoglu, Carla Ferreri, Luca Valgimigli, Riccardo Amorati & Branka Mihaljević. (2016) The effect of aromatic amines and phenols in the thiyl-induced reactions of polyunsaturated fatty acids. Radiation Physics and Chemistry 124, pages 104-110.
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. (2015) Safety and efficacy of ethoxyquin (6‐ethoxy‐1,2‐dihydro‐2,2,4‐trimethylquinoline) for all animal species. EFSA Journal 13:11.
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Kun Shen, Xiuling Han, Guoqin Xia & Xiyan Lu. (2015) Cationic Pd( ii )-catalyzed cyclization of N-tosyl-aniline tethered alkynyl ketones initiated by hydropalladation of alkynes: a facile way to 1,2-dihydro or 1,2,3,4-tetrahydroquinoline derivatives . Organic Chemistry Frontiers 2:2, pages 145-149.
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T. Lu, A.F. Harper, J. J. Dibner, J. M. Scheffler, B. A. Corl, M. J. Estienne, J. Zhao & R. A. Dalloul. (2014) Supplementing antioxidants to pigs fed diets high in oxidants: II. Effects on carcass characteristics, meat quality, and fatty acid profile1. Journal of Animal Science 92:12, pages 5464-5475.
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T. Lu, A. F. Harper, J. Zhao, M. J. Estienne & R. A. Dalloul. (2014) Supplementing antioxidants to pigs fed diets high in oxidants: I. Effects on growth performance, liver function, and oxidative status1. Journal of Animal Science 92:12, pages 5455-5463.
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T. Lu, A.F. Harper, J. Zhao, B.A. Corl, T. LeRoith & R.A. Dalloul. (2014) Effects of a dietary antioxidant blend and vitamin E on fatty acid profile, liver function, and inflammatory response in broiler chickens fed a diet high in oxidants. Poultry Science 93:7, pages 1658-1666.
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Unai Martínez-Estíbalez, Oihane García-Calvo, Verónica Ortiz-de-Elguea, Nuria Sotomayor & Esther Lete. (2013) Intramolecular Mizoroki-Heck Reaction in the Regioselective Synthesis of 4-Alkylidene-tetrahydroquinolines. European Journal of Organic Chemistry 2013:15, pages 3013-3022.
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Alina Błaszczyk, Aleksandra Augustyniak & Janusz Skolimowski. (2013) Ethoxyquin: An Antioxidant Used in Animal Feed. International Journal of Food Science 2013, pages 1-12.
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D. D. Boler, D. M. Fernández-Dueñas, L. W. Kutzler, J. Zhao, R. J. Harrell, D. R. Campion, F. K. McKeith, J. Killefer & A. C. Dilger. (2012) Effects of oxidized corn oil and a synthetic antioxidant blend on performance, oxidative status of tissues, and fresh meat quality in finishing barrows. Journal of Animal Science 90:13, pages 5159-5169.
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HUIJUAN JIA, HUIFENG REN, CHUANZONG DENG, HISANORI KATO & HIDEAKI ENDO. (2012) ANTIOXIDANT POTENTIAL OF WESTERN PARSLEY ( PETROSELINUM CRISPUM ) EXTRACT AND ITS EFFECTS ON OXIDATIVE STABILITIES OF FOOD DURING STORAGE . Journal of Food Biochemistry 36:6, pages 739-747.
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Vladimir V. Kouznetsov, Carlos M. Meléndez Gómez, Luz K. Luna Parada, John H. Bermudez, Leonor Y. Vargas Méndez & Amner Muñoz Acevedo. (2011) Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl3-catalyzed three-component Povarov reaction, using N-vinylamides. Molecular Diversity 15:4, pages 1007-1016.
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Cristina W. Nogueira & João B. T. Rocha. (2011) Toxicology and pharmacology of selenium: emphasis on synthetic organoselenium compounds. Archives of Toxicology 85:11, pages 1313-1359.
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Jean Fotie, Marcel Kaiser, Dawn A. Delfín, Joshua Manley, Carolyn S. Reid, Jean-Marc Paris, Tanja Wenzler, Louis Maes, Kiran V. Mahasenan, Chenglong Li & Karl A. Werbovetz. (2010) Antitrypanosomal Activity of 1,2-Dihydroquinolin-6-ols and Their Ester Derivatives. Journal of Medicinal Chemistry 53:3, pages 966-982.
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Naohiro Gotoh, Yosuke Noguchi, Akiko Ishihara, Kaita Yamaguchi, Hoyo Mizobe, Toshiharu Nagai, Ikuko Otake, Kenji Ichioka & Shun Wada. (2010) Highly Unsaturated Fatty Acid might Act as an Antioxidant in Emulsion System Oxidized by Azo Compound. Journal of Oleo Science 59:12, pages 631-639.
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D.R. Berdahl, R.I. Nahas & J.P. Barren. 2010. Oxidation in Foods and Beverages and Antioxidant Applications. Oxidation in Foods and Beverages and Antioxidant Applications 272 320 .
Alina Błaszczyk, Janusz Skolimowski & Alicja Materac. (2006) Genotoxic and antioxidant activities of ethoxyquin salts evaluated by the comet assay. Chemico-Biological Interactions 162:3, pages 268-273.
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Sangit Kumar & Lars Engman. (2006) Microwave-Assisted Copper-Catalyzed Preparation of Diaryl Chalcogenides. The Journal of Organic Chemistry 71:14, pages 5400-5403.
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Alina Błaszczyk & Janusz Skolimowski. (2006) Comparative analysis of cytotoxic, genotoxic and antioxidant effects of 2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline and ethoxyquin on human lymphocytes. Chemico-Biological Interactions 162:1, pages 70-80.
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. 2005. Handbook of Food Science, Technology, and Engineering - 4 Volume Set. Handbook of Food Science, Technology, and Engineering - 4 Volume Set 1604 1629 .
Anup G. Shah, John A. Pierson & Spyros G. Pavlostathis. (2005) Fate and effect of the antioxidant ethoxyquin on a mixed methanogenic culture. Water Research 39:17, pages 4251-4263.
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A. Błaszczyk, R. Osiecka & J. Skolimowski. (2003) Induction of chromosome aberrations in cultured human lymphocytes treated with ethoxyquin. Mutation Research/Genetic Toxicology and Environmental Mutagenesis 542:1-2, pages 117-128.
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