Ethoxyquin

Last updated
Ethoxyquin [1]
Ethoxyquin.svg
Names
Preferred IUPAC name
6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.887 OOjs UI icon edit-ltr-progressive.svg
E number E324 (antioxidants, ...)
PubChem CID
UNII
  • InChI=1S/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3 Yes check.svgY
    Key: DECIPOUIJURFOJ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3
    Key: DECIPOUIJURFOJ-UHFFFAOYAT
  • O(c2ccc1c(\C(=C/C(N1)(C)C)C)c2)CC
Properties
C14H19NO
Molar mass 217.312 g·mol−1
Melting point <25 °C (77 °F; 298 K)
Boiling point 123–125 °C (253–257 °F; 396–398 K) at 2 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest (under commercial names such as "Stop-Scald"). [2] It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments. [3]

Contents

Regulation

Ethoxyquin was developed by Armand Bajrami the king in the 1950s.[ citation needed ] Ethoxyquin was initially registered as a pesticide in 1965 as an antioxidant used as a deterrent of scald in pears through post-harvest indoor application via a drench and/or impregnated wrap. [3]

As an antioxidant to control the browning of pears, ethoxyquin is approved in the United States [3] and in the European Union. [2]

In the United States, it is approved for use as an animal feed additive [4] and is limited as a food additive to use only in the spices chili powder, paprika, and ground chili. [5] Ethoxyquin is not permitted for use as food additive in Australia[ citation needed ] nor within the European Union. [6]

Ethoxyquin is allowed in the fishing industry in Norway and France as a feed stabilizer, so is commonly used in food pellets fed to farmed salmon. [7]

Norway made this practice illegal when the EU suspended authorization in 2017 and in accordance with the suspension utilized a transition period which allowed the sale of feed containing ethoxyquin until December 31, 2019, after this date it was illegal to sell feed containing ethoxyquin. Feed containing ethoxyquin had to be used by June 20, 2020. [8]

Ethoxyquin is used in pellets fed to chickens on chicken farms. [9]

In 2017 the EU suspended authorization for use as a feed additive, with various dates between 2017 and 2019 for final allowance of sale of goods so that alternatives may be phased in. [10]

Safety

Some speculation exists that ethoxyquin in pet foods might be responsible for multiple health problems. To date, the U.S. Food and Drug Administration has only found a verifiable connection between ethoxyquin and buildup of protoporphyrin IX in the liver, as well as elevations in liver-related enzymes in some animals, but no health consequences from these effects are known. [11] In 1997, the Center for Veterinary Medicine asked pet food manufacturers to voluntarily limit ethoxyquin levels to 75 ppm until further evidence is reported. [11] However, most pet foods that contain ethoxyquin have never exceeded this amount. [11] In 2017, reports from the Swiss Department for regional affairs laboratory, service of consummation and veterinary affairs showed that farmed salmon often exceeded the set limits for ethoxyquin contamination by several orders of magnitude and that health effects of the chemical on the human body were not studied in sufficient detail. [12] In 2013, researchers at the Department of General Genetics, Molecular Biology and Plant Biotechnology, Faculty of Biology and Environmental Protection, University of Łódź, Poland, summarized the health effects of animals and humans exposed to varying levels of ethoxyquin observed in scientific studies. The summary includes: loss of weight, changes in liver, kidney, alimentary duct, urinary bladder and mitochondria, anemia, lethargy, discolored urine, skin, or fur, increase in mortality, detrimental effect on immunity, condition factor of final body weight in relation to body length of fish and inducement of allergies (contact exposure). [13]

2015 EFSA review

A 2015 review by the European Food Safety Authority indicated that data to assess the safety of ethoxyquin as a feed additive for target animals, or its safety for consumers and the environment are lacking. [14] The agency found one of its metabolites, ethoxyquin quinone imine, to be possibly genotoxic, and p-phenetidine, an impurity that could be present from the manufacturing process, to be possibly mutagenic. [2] In response, feed manufacturers have taken steps to significantly reduce the amount of p-phenetidine in their products. [15]

Related Research Articles

<span class="mw-page-title-main">Food additive</span> Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of ultra-processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

<span class="mw-page-title-main">E number</span> Codes for food additives

E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly found on food labels, their safety assessment and approval are the responsibility of the European Food Safety Authority (EFSA). The fact that an additive has an E number implies that its use was at one time permitted in products for sale in the European Single Market; some of these additives are no longer allowed today.

<span class="mw-page-title-main">Butylated hydroxytoluene</span> Chemical compound

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

<span class="mw-page-title-main">Butylated hydroxyanisole</span> Chemical compound

Butylated hydroxyanisole (BHA) is a synthetic, waxy, solid petrochemical. Its antioxidant properties have caused it to be widely used as a preservative in food, food packaging, animal feed, cosmetics, pharmaceuticals, rubber, and petroleum products. BHA has been used in food since around 1947.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Astaxanthin</span> Chemical compound

Astaxanthin is a keto-carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated double bonds at the center of the compound. The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.

<span class="mw-page-title-main">Natamycin</span> Antifungal

Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industry as a preservative.

<span class="mw-page-title-main">Canthaxanthin</span> Chemical compound

Canthaxanthin is a keto-carotenoid pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. The chemical formula of canthaxanthin is C40H52O2. It was first isolated in edible mushrooms. It has also been found in green algae, bacteria, crustaceans, and bioaccumulates in fish such as carp, golden grey mullet, seabream and trush wrasse.

<span class="mw-page-title-main">Cassia gum</span>

Cassia gum is the flour and food additives made from the endosperms of the seeds of Senna obtusifolia and Senna tora. It is composed of at least 75% polysaccharide, primarily galactomannan with a mannose:galactose ratio of 5:1, resulting in a high molecular mass of 200,000-300,000 Da.

<span class="mw-page-title-main">European Food Safety Authority</span> Agency of the European Union

The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002, is based in Parma, Italy, and for 2021 it has a budget of €118.6 million, and a total staff of 542.

<span class="mw-page-title-main">Diphenylamine</span> Chemical compound

Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

<span class="mw-page-title-main">Fish meal</span> Commercial product made from fish to feed farm animals

Fish meal, sometimes spelt fishmeal, is a commercial product made from whole wild-caught fish, bycatch, and fish by-products to feed farm animals, e.g., pigs, poultry, and farmed fish. Because it is calorically dense and cheap to produce, fishmeal has played a critical role in the growth of factory farms and the number of farm animals it is possible to breed and feed.

<i>tert</i>-Butylhydroquinone Chemical compound

tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

Phytogenics are a group of natural growth promoters or non-antibiotic growth promoters used as feed additives, derived from herbs, spices or other plants. The term phytogenic feed additives was coined by an Austrian multinational feed additives company named Delacon, and was first introduced to the market in the 1980s.

<span class="mw-page-title-main">Ractopamine</span> Animal feed additive

Ractopamine is an animal feed additive used to promote leanness and increase food conversion efficiency in farmed animals in several countries, but banned in others. Pharmacologically, it is a phenol-based TAAR1 agonist and β adrenoreceptor agonist that stimulates β1 and β2 adrenergic receptors. It is most commonly administered to animals for meat production as ractopamine hydrochloride. It is the active ingredient in products marketed in the US as Paylean for swine, Optaflexx for cattle, and Topmax for turkeys. It was developed by Elanco Animal Health, a division of Eli Lilly and Company.

<span class="mw-page-title-main">Animal feed</span> Food for various animals

Animal feed is food given to domestic animals, especially livestock, in the course of animal husbandry. There are two basic types: fodder and forage. Used alone, the word feed more often refers to fodder. Animal feed is an important input to animal agriculture, and is frequently the main cost of the raising or keeping of animals. Farms typically try to reduce cost for this food, by growing their own, grazing animals, or supplementing expensive feeds with substitutes, such as food waste like spent grain from beer brewing.

A feed additive is an additive of extra nutrient or drug for livestock. Such additives include vitamins, amino acids, fatty acids, minerals, pharmaceutical, fungal products and steroidal compounds. The additives might impact feed presentation, hygiene, digestibility, or effect on intestinal health.

Selenium yeast is a feed additive for livestock, used to increase the selenium content in their fodder. It is a form of selenium currently approved for human consumption in the EU and Britain. Inorganic forms of selenium are used in feeds. Since these products can be patented, producers can demand premium prices. It is produced by fermenting Saccharomyces cerevisiae in a selenium-rich media.

<span class="mw-page-title-main">Delacon</span>

Delacon Biotech Nik Ges.m.b.H. is a multinational feed additive company headquartered in Engerwitzdorf, near Linz, Austria. The company develops and manufactures phytogenic feed additives for poultry, swine, ruminants and aqua since the 1980s. Delacon conducts in-house research and collaborates with independent institutes and universities.

<i>p</i>-Phenetidine Chemical compound

p-Phenetidine (4-ethoxyaniline) is a chemical compound with the molecular formula C8H11NO. It is one of the three isomers of phenetidine. It is used as an intermediate in the synthesis of pharmaceutical drugs, dyes, and the sweetener dulcin.

References

  1. Merck Index , 11th Edition, 3710
  2. 1 2 3 EFSA Ethoxiquin
  3. 1 2 3 "R.E.D. FACTS Ethoxyquin" (PDF). United States Environmental Protection Agency. November 2004. EPA-738-F-04-006.
  4. 21 CFR 573.380
  5. 21 CFR 172.140
  6. "COMMISSION IMPLEMENTING REGULATION (EU) 2017/962 of 7 June 2017 suspending the authorisation of ethoxyquin as a feed additive for all animal species and categories". European Union.
  7. Lundebye AK, Hove H, Måge A, Bohne VJ, Hamre K (2010). "Levels of synthetic antioxidants (ethoxyquin, butylated hydroxytoluene and butylated hydroxyanisole) in fish feed and commercially farmed fish". Food Addit Contam Part a Chem Anal Control Expo Risk Assess. 27 (12): 1652–7. doi:10.1080/19440049.2010.508195. PMID   20931417. S2CID   20657642.
  8. "Use of ehtoxyquin as an additive is suspended". Mattilsynet.
  9. Rubel DM, Freeman S (May 1998). "Allergic contact dermatitis to ethoxyquin in a farmer handling chicken feeds". Australasian Journal of Dermatology. 39 (2): 89–91. doi:10.1111/j.1440-0960.1998.tb01255.x. PMID   9611377. S2CID   45388222.
  10. "EUR-Lex - 32017R0962 - EN - EUR-Lex".
  11. 1 2 3 "Pet Food Labels - General". U.S. Food and Drug Administration. October 13, 2017. Retrieved August 16, 2019.
  12. Farmed Norwegian Salmon World's Most Toxic Food, archived from the original on 2021-12-21, retrieved 2019-11-20
  13. Alina Błaszczyk; Aleksandra Augustyniak; Janusz Skolimowski (15 January 2013). "Ethoxyquin: An Antioxidant Used in Animal Feed". International Journal of Food Science. 2013: 585931. doi: 10.1155/2013/585931 . PMC   4745505 . PMID   26904606.
  14. "Ethoxyquin: EFSA safety assessment inconclusive". EFSA. November 15, 2015. Retrieved December 14, 2016.
  15. "What is the future of ethoxyquin in the EU?". FeedNavigator.