Ethoxyquin: Difference between revisions

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| Reference=<ref>''[[Merck Index]]'', 11th Edition, '''3710'''</ref>

| Name = Ethoxyquin

| ImageFile = Ethoxyquin.svg

| ImageSize = 200px

| ImageName = Ethoxyquin

| PIN = 6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 77323

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| CASNo_Ref = {{cascite|correct|CAS}}

| SMILES = O(c2ccc1c(\C(=C/C(N1)(C)C)C)c2)CC

|Section2={{Chembox Properties

| C=14 | H=19 | N=1 | O=1

| MeltingPt = <

| MeltingPtC = 25

| BoilingPtC = 123–125

| BoilingPt_notes = at 2 mmHg

'''Ethoxyquin''' (EMQ) is a [[quinoline]]-based [[antioxidant]] used as a [[food preservative]] in certain countries and originally to control [[pear scald|scald]] on pears after harvest (under commercial names such as "Stop-Scald").<ref name=efsa>[https://efsa.onlinelibrary.wiley.com/doi/abs/10.2903/j.efsa.2013.3231 EFSA Ethoxiquin]</ref> It is used as a preservative in some pet foods to slow the development of [[rancidification|rancidity]] of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural [[carotenoid]] pigments.<ref name="EPA R.E.D. Facts: Ethoxyquin">{{cite web |url=https://archive.epa.gov/pesticides/reregistration/web/pdf/0003fact.pdf |title=R.E.D. FACTS Ethoxyquin |website=United States Environmental Protection Agency |id=EPA-738-F-04-006 |date=November 2004}}</ref>

==Regulation==

Ethoxyquin was developed by Armand Bajrami the king in the 1950s.{{citation needed|date=March 2019}} 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.<ref name="EPA R.E.D. Facts: Ethoxyquin"/>

As an antioxidant to control the browning of pears, ethoxyquin is approved in the United States<ref name="EPA R.E.D. Facts: Ethoxyquin"/> and in the European Union.<ref name=efsa/>

In the United States, it is approved for use as an animal [[feed additive]]<ref>{{CodeFedReg|21|573|380}}</ref> and is limited as a [[food additive]] to use only in the spices chili powder, paprika, and ground chili.<ref>{{CodeFedReg|21|172|140}}</ref> Ethoxyquin is not permitted for use as food additive in Australia{{citation needed|date=February 2018}} nor within the European Union.<ref>{{cite web | url = http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32017R0962&from=EN | title = 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 | publisher = European Union}}</ref>

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]].<ref>{{cite journal|vauthors=Lundebye AK, Hove H, Måge A, Bohne VJ, Hamre K|title=Levels of synthetic antioxidants (ethoxyquin, butylated hydroxytoluene and butylated hydroxyanisole) in fish feed and commercially farmed fish|pmid=20931417|doi=10.1080/19440049.2010.508195|volume=27|issue=12|pages=1652–7|journal=Food Addit Contam Part a Chem Anal Control Expo Risk Assess|year=2010|s2cid=20657642}}</ref>

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.<ref>{{ cite web | url = https://www.mattilsynet.no/dyr_og_dyrehold/for/bruk_av_ethoxyquin_eq_som_tilsetningsstoff_i_for_er_faset_ut.25269 | title = Use of ehtoxyquin as an additive is suspended | publisher = Mattilsynet}}</ref>

Ethoxyquin is used in pellets fed to chickens on chicken farms.<ref>{{cite journal | pmid=9611377 | journal = Australasian Journal of Dermatology | date = May 1998 | volume = 39 | issue = 2 | pages = 89–91 | title = Allergic contact dermatitis to ethoxyquin in a farmer handling chicken feeds | vauthors = Rubel DM, Freeman S | doi=10.1111/j.1440-0960.1998.tb01255.x| s2cid = 45388222 }}</ref>

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.<ref>{{cite web |url=https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32017R0962 |title = EUR-Lex - 32017R0962 - EN - EUR-Lex}}</ref>

==Safety==

Some speculation exists that ethoxyquin in pet foods might be responsible for multiple health problems. To date, the [[Food and Drug Administration (United States)|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.<ref name="FDA">{{cite web | url = https://www.fda.gov/animal-veterinary/animal-health-literacy/pet-food-labels-general | title = Pet Food Labels - General | publisher = [[U.S. Food and Drug Administration]] | date = October 13, 2017 | access-date = August 16, 2019}}</ref> In 1997, the Center for Veterinary Medicine asked pet food manufacturers to voluntarily limit ethoxyquin levels to 75 [[Parts per million|ppm]] until further evidence is reported.<ref name="FDA"/> However, most pet foods that contain ethoxyquin have never exceeded this amount.<ref name="FDA"/> 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.<ref>{{Citation|title=Farmed Norwegian Salmon World's Most Toxic Food|url=https://www.youtube.com/watch?v=RYYf8cLUV5E |archive-url=https://ghostarchive.org/varchive/youtube/20211221/RYYf8cLUV5E |archive-date=2021-12-21 |url-status=live|language=en|access-date=2019-11-20}}{{cbignore}}</ref> 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).<ref>{{cite journal | title = Ethoxyquin: An Antioxidant Used in Animal Feed |journal=International Journal of Food Science |author=Alina Błaszczyk |author2=Aleksandra Augustyniak |author3=Janusz Skolimowski |volume=2013|page=585931|date=15 January 2013|doi = 10.1155/2013/585931|pmid = 26904606|pmc = 4745505|doi-access=free }}</ref>

===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.<ref name=efsa2>{{cite web| url= http://www.efsa.europa.eu/en/press/news/151118| title=Ethoxyquin: EFSA safety assessment inconclusive| publisher=EFSA| date=November 15, 2015| access-date=December 14, 2016}}</ref> The agency found one of its [[metabolite]]s, ethoxyquin quinone imine, to be possibly genotoxic, and [[p-Phenetidine|''p''-phenetidine]], an impurity that could be present from the manufacturing process, to be possibly mutagenic.<ref name=efsa/> In response, feed manufacturers have taken steps to significantly reduce the amount of ''p''-phenetidine in their products.<ref>{{cite web |url=https://www.feednavigator.com/Article/2016/03/10/What-is-the-future-of-ethoxyquin-in-the-EU |title=What is the future of ethoxyquin in the EU? |website=FeedNavigator}}</ref>

[[Category:Phenol ethers]]

[[Category:Ethoxy compounds]]