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{{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)}}
{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 402021515 | verifiedrevid = 442926733
| Name = Erythrosine | Name = Erythrosine
| ImageFile = Erythrosine.svg | ImageFile = Erythrosine.svg
| ImageSize = 230px | ImageSize = 230px
| ImageName = Erythrosine | ImageName = Erythrosine
| IUPACName = 2-(6-Hydroxy-2,4,5,7-tetraiodo-3-oxo-xanthen-9-yl)benzoic acid | IUPACName = 2-(6-Hydroxy-2,4,5,7-tetraiodo-3-oxo-xanthen-9-yl)benzoic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3144 | ChemSpiderID = 3144
| UNII_Ref = {{fdacite|correct|FDA}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| UNII = PN2ZH5LOQY | ChEMBL = 1332616
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 8TL7LH93FM
| InChI = 1/C20H8I4O5/c21-11-5-9-17(13(23)15(11)25)28-18-10(6-12(22)16(26)14(18)24)20(9)8-4-2-1-3-7(8)19(27)29-20/h1-6,25-26H | InChI = 1/C20H8I4O5/c21-11-5-9-17(13(23)15(11)25)28-18-10(6-12(22)16(26)14(18)24)20(9)8-4-2-1-3-7(8)19(27)29-20/h1-6,25-26H
| InChIKey = OALHHIHQOFIMEF-UHFFFAOYAB | InChIKey = OALHHIHQOFIMEF-UHFFFAOYAB
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| StdInChIKey = OALHHIHQOFIMEF-UHFFFAOYSA-N | StdInChIKey = OALHHIHQOFIMEF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 16423-68-0 | CASNo = 16423-68-0
| SMILES = Ic5cc4c(Oc1c(cc(I)c(O)c1I)C43OC(=O)c2ccccc23)c(I)c5O | SMILES = C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C1C=C(I)C()=C2I..
| PubChem = 3259 | PubChem = 3259
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>20</sub>H<sub>6</sub>I<sub>4</sub>Na<sub>2</sub>O<sub>5</sub> | Formula = C<sub>20</sub>H<sub>6</sub>I<sub>4</sub>Na<sub>2</sub>O<sub>5</sub>
| MolarMass = 879.86 g/mol | MolarMass = 879.86 g/mol
| Density = | Density =
| MeltingPtC = 142 to 144
| MeltingPt =
| 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 = | BoilingPt =
}} }}
|Section3={{Chembox Hazards
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
}}
}} }}


'''Erythrosine''', also known as Red No. 3, is an ], specifically a derivative of ]. It is cherry-pink synthetic, primarily used for ].<ref name=Ullmann>Phyllis A. Lyday "Iodine and Iodine Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim</ref> It is the disodium ] of 2,4,5,7-tetraiodo]. Its maximum absorbance is at 530&nbsp;]<ref></ref> in an aqueous solution, and it is subject to ].{{Citation needed|date=February 2007}} '''Erythrosine''', also known as '''Red No. 3''', is an ], specifically a derivative of ]. It is a pink dye which is primarily used for ].<ref name=Ullmann>{{cite book | first = Phyllis A. | last = Lyday | name-list-style = vanc | chapter = Iodine and Iodine Compounds | title = Ullmann's Encyclopedia of Industrial Chemistry | date = 2005 | publisher = Wiley-VCH | location = Weinheim }}</ref> It is the disodium ] of 2,4,5,7-tetraiodo]. Its maximum absorbance is at 530&nbsp;]<ref>{{cite web | first = Robert John | last = Lancashire | name-list-style = vanc | publisher = Department of Chemistry, University of the West Indies |url= http://wwwchem.uwimona.edu.jm:1104/lectures/ecode.html |title=Food Color Additives<!-- Bot generated title --> |access-date=2007-01-29 | archive-url= https://web.archive.org/web/20070128165006/http://wwwchem.uwimona.edu.jm:1104/lectures/ecode.html |archive-date=2007-01-28 |url-status=dead }}</ref> in an aqueous solution, and it is subject to ].


==Uses== ==Uses==
It is used as a ],<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> ] 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" /> ] 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> ] 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 ] 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>
It is used as a ], in ] inks, as a biological stain, a ] disclosing agent and a ] medium. Erythrosine is commonly used in sweets such as some candies and popsicles, and even more widely used in cake-decorating gels. It is also used to color ] shells.<ref></ref><ref>Blue Diamond Ultra Premium Blend Mixed Nuts, distributed by Diamond Foods, Inc. Stockton, CA</ref> As a food additive, it has the ] E127.


Erythrosine is commonly used in sweets such as some candies and ], and even more widely used in cake-decorating gels. It was also used to color ] 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 ] E127.
While commonly used in many countries of the world, erythrosine is less commonly used in the United States (the second least used after ]) because ] (Red #40) is generally used instead. However, Allura Red AC is banned in many European countries because it is an ], despite the fact that it has fewer known health risks than erythrosine.{{Citation needed|date=April 2010}}


==Regulation and prevalence==
As a result of efforts begun in the 1970s, in 1990 the U.S. FDA had instituted a partial ban on erythrosine, citing research that high doses have been found to cause cancer in rats.<ref>, ''The Washington Post'', February 7, 1990</ref> In June of 2008, the ] (CSPI) petitioned the FDA for a complete ban on erythrosine in the United States.<ref>, CBS News, June 3, 2008</ref>
Erythrosine is restricted as a food additive in the European Union, China, and 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> Its usage is limited in Australia, and New Zealand.<ref>{{Citation |last=FSANZ |title=Australia New Zealand Food Standards Code – Schedule 8 – Food additive names and code numbers (for statement of ingredients) |date=2021-03-26 |url=https://www.legislation.gov.au/F2015L00478/latest/text |access-date=2024-09-19 |publisher=Office Parliamentary Counsel; Locked Bag 30 Kingston ACT 2604}}</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 ] drugs. It is less commonly used in the United States because ] (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 ] variant is also banned from use in the United States.


The ] 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 }}
A series of toxicology tests combined with a review of other reported studies concluded that erythrosine is non-].<ref>{{Cite journal | doi = 10.1093/mutage/1.4.253 | title = Mutagenicity studies on FD&C Red No.3 | year = 1986 | last1 = Lin | first1 = George H. Y. | last2 = Brusick | first2 = David J. | journal = Mutagenesis | volume = 1 | issue = 4 | pages = 253–259 | pmid = 2457780}}</ref> Up to now, erythrosine can be used in colored food in USA without any restriction ().


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>
⚫ ==Synonyms==

⚫ Erythrosine B; Erythrosin B; Acid Red 51; C.I. 45430; FD & C Red No.3; E127;
===United States===
⚫ 2',4',5',7'-Tetraiodo-3',6'-dihydroxy-spiro-3-one disodium salt; Tetraiodofluorescein Sodium Salt; 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; Spiroxanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt.<ref>, University of South Carolina</ref><ref>, chemicalland21.com</ref>
As a result of efforts begun in the 1970s, in 1990, the U.S. ] (FDA) instituted a partial ban on erythrosine, citing research that high doses cause cancer in rats.<ref>, ''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-] 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 ] (CSPI) petitioned the FDA for a complete ban on erythrosine in the United States,<ref>{{cite web|url=https://www.cbsnews.com/news/fda-urged-to-ban-some-food-dyes/|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=live}}</ref> but the FDA has not taken any further action.

As of May 2023, the U.S. state of ] 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> by Dana G. Smith, April 13, 2023 on the New York Times website. Last access 5/23/2023.</ref> ] 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: ], ], and ].<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=]|lang=en}}</ref><ref> 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-3-one disodium salt; Tetraiodofluorescein sodium salt; 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; Spiroxanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt.<ref> {{Webarchive|url=https://web.archive.org/web/20100317184306/http://www.usca.edu/chemistry/spectra/erythrosin.htm |date=2010-03-17 }}, University of South Carolina</ref><ref>, chemicalland21.com</ref>


==Classification== ==Classification==
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* ] E127 (Food Red 14) * ] E127 (Food Red 14)
* ] no. 45430 (Acid Red 51) * ] no. 45430 (Acid Red 51)
* ] No. 1697 * ] No. 1697


==References== == References ==
{{reflist}} {{reflist}}


==External links== == External links ==
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* *


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