Erythrosine: Difference between revisions

{{Short description|Iodo-derivative of fluorone used as a pink dye}}

{{use dmy dates |date=November 2023}}

{{redirect|Red 3|the techno release called Red Three|Dave Clarke (DJ)}}

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| verifiedrevid =

| Name = Erythrosine

| ImageFile = Erythrosine.svg

| ImageSize = 230px

| ImageName = Erythrosine

| IUPACName = 2-(6-Hydroxy-2,4,5,7-tetraiodo-3-oxo-xanthen-9-yl)benzoic acid

|Section1={{Chembox Identifiers

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

| = {{||}}

| =

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 8TL7LH93FM

| CASNo = 16423-68-0

| SMILES = ((I)(O)()(I)

| PubChem = 3259

|Section2={{Chembox Properties

| Formula = C₂₀H₆I₄Na₂O₅

| MolarMass = 879.86 g/mol

| Density =

| MeltingPtC = 142 to 144

| MeltingPt_ref = <ref>{{cite web | title = Erythrosine B product description | url = http://www.chemicalbook.com/ChemicalProductProperty_US_CB0393696.aspx | work = The Chemical Book }}</ref>

| BoilingPt =

|Section3={{Chembox Hazards

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

}}

'''Erythrosine''', also known as Red No. 3, is an [[organoiodine compound]], specifically a derivative of [[fluorone]]. It is pink primarily used for [[food coloring]].<ref name=Ullmann>Phyllis A. Lyday Iodine and Iodine Compounds Ullmann's Encyclopedia of Industrial Chemistry 2005 Wiley-VCH Weinheim</ref> It is the disodium [[salt (chemistry)|salt]] of 2,4,5,7-tetraiodo[[fluorescein]]. Its maximum absorbance is at 530&nbsp;[[nanometer|nm]]<ref>http://wwwchem.uwimona.edu.jm:1104/lectures/ecode.html Food Color Additives<!-- Bot generated title --></ref> in an aqueous solution, and it is subject to [[photodegradation]].

It is used as a [[food coloring]],<ref>{{cite journal | vauthors = Chequer FM, Venâncio VP, Bianchi ML, Antunes LM | title = Genotoxic and mutagenic effects of erythrosine B, a xanthene food dye, on HepG2 cells | journal = Food and Chemical Toxicology | volume = 50 | issue = 10 | pages = 3447–51 | date = October 2012 | pmid = 22847138 | doi = 10.1016/j.fct.2012.07.042 | doi-access = free }}</ref> [[printing]] ink,<ref>{{cite book |title=Synthetic Dyes in Biology, Medicine And Chemistry |last=Gurr |first=Edward | name-list-style = vanc |publisher=elsevier|year=2012|pages=197, 198}}</ref> biological stain,<ref name=":0" /> [[dental plaque]] disclosing agent,<ref>{{cite journal | vauthors = Wood S, Metcalf D, Devine D, Robinson C | title = Erythrosine is a potential photosensitizer for the photodynamic therapy of oral plaque biofilms | journal = The Journal of Antimicrobial Chemotherapy | volume = 57 | issue = 4 | pages = 680–4 | date = April 2006 | pmid = 16464894 | doi = 10.1093/jac/dkl021 | doi-access = free }}</ref> [[radiodensity|radiopaque]] medium,<ref name=":0">{{cite book |title=Dictionary of Analytical Reagents |publisher=CRC Press |year=1993 |isbn= 978-0-412-35150-1 |pages=474 }}</ref> sensitizer for [[orthochromatic]] photographic films, and visible light photoredox catalyst.<ref>{{cite journal | vauthors = Rogers DA, Brown RG, Brandeburg ZC, Ko EY, Hopkins MD, LeBlanc G, Lamar AA | title = N-Bromosuccinimide | journal = ACS Omega | volume = 3 | issue = 10 | pages = 12868–12877 | date = October 2018 | pmid = 31458011 | pmc = 6644467 | doi = 10.1021/acsomega.8b02320 }}</ref>

Erythrosine is commonly used in sweets such as some candies and [[Ice pop|ice pops]], and even more widely used in cake-decorating gels. It was also used to color [[pistachio]] shells.<ref>{{Cite web |last=Day |first=Chris |date=2023-01-16 |title=The Almost-Forgotten Era Of Red Pistachios |url=https://www.thedailymeal.com/1168708/the-almost-forgotten-era-of-red-pistachios/ |access-date=2023-11-17 |website=The Daily Meal |language=en-US}}</ref> As a food additive, it has the [[E number]] E127.

==Regulation and prevalence==

Erythrosine is banned as a food additive in the European Union, Japan, China, the United Kingdom,<ref>{{cite news |url=https://www.npr.org/2021/10/15/1046348573/sprinklegate-sinks-a-u-k-bakerys-top-sellers-after-topping-is-found-to-be-illega |title='Sprinklegate' sinks a U.K. bakery's top sellers after topping is found to be illegal |date=October 15, 2021 |first=Bill |last=Chappell |access-date=29 November 2023 }}</ref> Australia, and New Zealand.<ref>{{cite news |last1=Hernandez |first1=Joe |title=California becomes the first state to ban 4 food additives linked to disease |url=https://www.npr.org/2023/10/10/1204839281/california-ban-food-additives-red-dye-3-propylparaben-candy |work=NPR |date=October 10, 2023}}</ref><ref>{{cite news |last1=Magazine |first1=Smithsonian |last2=Osborne |first2=Margaret |title=What to Know About California's New Law Banning Food Additives, Including Red Dye No. 3 |url=https://www.smithsonianmag.com/smart-news/california-bans-food-additives-including-red-dye-no-3-180983082/ |work=Smithsonian Magazine |date=October 17, 2023 |language=en}}</ref> Erythrosine can be used in colored food and ingested drugs in the U.S. without any restriction; however, its use is banned in cosmetics and [[topical]] drugs. It is less commonly used in the United States because [[Allura Red AC]] (Red #40) is generally used instead.<ref>{{cite web | url=https://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm106626.htm | title=Color Additive Status List | work=Food & Drug Administration | date=December 2015 | access-date=May 16, 2016}}</ref> The [[Lake pigment|lake]] variant is also banned from use in the United States.

The [[European Food Safety Authority]] only allows erythrosine in processed cherries<ref>{{cite journal |last1=EFSA |title=Scientific Opinion on the re-evaluation of Erythrosine (E 127) as a food additive |journal=EFSA Journal |date=2011 |volume=9 |issue=1 |page=1854 |doi=10.2903/j.efsa.2011.1854|url=https://phaidra.univie.ac.at/o:245195 |author1-link=EFSA }}

Erythrosine is exclusively authorised for use in cocktail and candied cherries, and Bigarreaux cherries</ref> and pet foods.<ref>{{cite journal |last1=EFSA |title=Update of the Scientific Opinion on the safety and efficacy of erythrosine in feed for cats, dogs, reptiles and ornamental fish |journal=EFSA Journal |date=2015 |volume=13 |issue=9 |page=4233 |doi=10.2903/j.efsa.2015.4233|author1-link=EFSA |doi-access=free |hdl=2434/559021 |hdl-access=free }}</ref><ref>{{cite journal |last1=EFSA|title=Safety of erythrosine for ornamental fish |journal=EFSA Journal |date=2019 |volume=17 |issue=5 |page=5699 |doi=10.2903/j.efsa.2019.5699|pmid=32626322 | pmc=7009114 |author1-link=EFSA }}</ref>

===United States===

As a result of efforts begun in the 1970s, in 1990, the U.S. [[Food and Drug Administration]] (FDA) instituted a partial ban on erythrosine, citing research that high doses cause cancer in rats.<ref>[https://www.washingtonpost.com/archive/politics/1990/02/07/fda-red-dyes-reluctant-regulator/04320829-9727-4d2e-b3d5-53e9bbbca0dd/ FDA: Red Dye's Reluctant Regulator; Partial Ban Points to Limitations of 30-Year-Old Delaney Clause], ''The Washington Post'', February 7, 1990</ref> A 1990 study concluded that "chronic erythrosine ingestion may promote thyroid tumor formation in rats via chronic stimulation of the thyroid by TSH." with 4% of total daily dietary intake consisting of erythrosine B.<ref>{{cite journal | vauthors = Jennings AS, Schwartz SL, Balter NJ, Gardner D, Witorsch RJ | title = Effects of oral erythrosine (2',4',5',7'-tetraiodofluorescein) on the pituitary-thyroid axis in rats | journal = Toxicology and Applied Pharmacology | volume = 103 | issue = 3 | pages = 549–56 | date = May 1990 | pmid = 2160137 | doi = 10.1016/0041-008x(90)90327-q | doi-access = free }}</ref> A series of toxicology tests combined with a review of other reported studies concluded that erythrosine is non-[[genotoxic]] and any increase in tumors is caused by a non-genotoxic mechanism.<ref>{{cite journal | vauthors = Lin GH, Brusick DJ | title = Mutagenicity studies on FD&C red No.3 | journal = Mutagenesis | volume = 1 | issue = 4 | pages = 253–9 | date = July 1986 | pmid = 2457780 | doi = 10.1093/mutage/1.4.253 }}</ref>

In June 2008, the [[Center for Science in the Public Interest]] (CSPI) petitioned the FDA for a complete ban on erythrosine in the United States,<ref>{{cite web|url=http://www.cbsnews.com/stories/2008/06/03/health/main4151092.shtml|title=FDA Urged To Ban Some Food Dyes|publisher=CBS News|date=June 3, 2008|archive-url=https://web.archive.org/web/20120827181228/http://www.cbsnews.com/stories/2008/06/03/health/main4151092.shtml|archive-date=2012-08-27|access-date=2022-11-14|url-status=dead}}</ref> but the FDA has not taken any further action.

As of May 2023, the U.S. state of [[New York (state)|New York]] is considering banning the use of Red Dye No. 3 in foods (it was already banned from cosmetics as of 1990) because it has been shown to cause cancer in animals and because of claims that it, and other synthetic food dyes, may contribute to child behavioral problems such as hyperactivity.<ref name=NJTimesMay2023>[https://www.nytimes.com/2023/04/13/well/eat/food-additive-ban.html Two States Have Proposed Bans on Common Food Additives Linked to Health Concerns] by Dana G. Smith, April 13, 2023 on the New York Times website. Last access 5/23/2023.</ref> [[California]] plans to ban the manufacture, sale, and distribution of foods containing Red Dye No. 3 starting in 2027, following a bill signed into law in October 2023 that also bans three other food additives: [[propylparaben]], [[potassium bromate]], and [[brominated vegetable oil]].<ref>{{cite web|title = California becomes first US state to ban 4 potentially harmful chemicals in food | work = CNN | url = https://www.cnn.com/2023/10/09/health/california-governor-bans-red-dye-no-3-wellness/index.html | date = October 10, 2023}}</ref><ref>{{cite web|url=https://leginfo.legislature.ca.gov/faces/billCompareClient.xhtml?bill_id=202320240AB418&showamends=false|title=AB-418 The California Food Safety Act.|publisher=[[ca.gov]]|lang=en}}</ref><ref>[https://www.washingtonpost.com/wellness/2023/10/11/california-skittles-ban-chemicals-food/ California isn’t banning Skittles, but four additives will be removed] by Marlene Cimons, Washington Post, Oct. 11, 2023. The article notes that Red dye No. 3, bromated vegetable oil, potassium bromate and propyl paraben all have been linked to risk of cancer and hyperactivity in children.</ref>

==Synonyms==

Erythrosine B; Erythrosin B; Acid Red 51; C.I. 45430; FD&C Red No.3; E127;

2',4',5',7'-Tetraiodo-3',6'-dihydroxy-spiro[3H-isobenzofuran-1,9'-xanthen]-3-one disodium salt; Tetraiodofluorescein ; Calcoid Erythrosine N; 2,4,5,7-Tetraiodo-3,6-dihydroxyxanthene-9-spiro-1'-3H-isobenzofuran-3'-one disodium salt; 2',4',5',7'-Tetraiodofluorescein, disodium salt; C.I.Food Red 14; Aizen Erythrosine; Tetraiodifluorescein, disodium salt; Spiro[isobenzofuran- 1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt.<ref>[http://www.usca.edu/chemistry/spectra/erythrosin.htm Erythrosin B], University of South Carolina</ref><ref>[http://chemicalland21.com/lifescience/foco/ERYTHROSINE%20B.htm Erythrosine], chemicalland21.com</ref>

* [[ Indian Standards]] No. 1697

==References==

==External links==

* [http://www.bis.org.in/cert/man.htm Bureau of Indian Standards: List of Indian Standards under mandatory certification]

[[Category:]]

[[Category:Salts of carboxylic acids]]

[[Category:Triarylmethane dyes]]

[[Category:Organic sodium salts]]

[[Category:E-number additives]]