Erythrosine

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Erythrosine
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Names
IUPAC name
2-(6-Hydroxy-2,4,5,7-tetraiodo-3-oxo-xanthen-9-yl)benzoic acid
Identifiers
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3D model (JSmol)
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  • InChI=1S/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 checkY
    Key: OALHHIHQOFIMEF-UHFFFAOYSA-N checkY
  • 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
    Key: OALHHIHQOFIMEF-UHFFFAOYAB
  • [O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C1C=C(I)C([O-])=C2I.[Na+].[Na+]
Properties
C20H6I4Na2O5
Molar mass 879.86 g/mol
Melting point 142 to 144 °C (288 to 291 °F; 415 to 417 K)[1]
Hazards
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2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Erythrosine, also known as E127 and Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is a red-pink dye used for food coloring, cosmetics, hair coloring, pet products, and diverse industrial colorings.[2][3] It is the disodium salt of 2,4,5,7-tetraiodofluorescein.[2]

History

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The colorant was discovered by the Swiss chemist Karl Kussmaul at the University of Basel in 1876 and soon commercialized by the local Bindschedler & Busch company for dyeing wool and silk.[4][5] Its use as a textile dye was soon superseded due to its propensity to fade in sunlight.[6][7]

Its use as a food dye was legalized in the US by the Pure Food and Drug Act of 1906.[8] By early 1920s, it was produced mainly for the food industry,[9] with 2,170 pounds (0.98 t) made in America in 1924,[10] rising to 9,468 pounds (4.29 t) in 1938[11] and approximately 50 tons in 1967.[12]

Production

Erythrosine is synthesized from resorcinol and phthalic anhydride, which are processed into fluorescein. Fluorescein then undergoes iodination, producing the bright red dye.

Uses

It is used as a food coloring,[13] printing ink,[14] biological stain,[15] dental plaque disclosing agent,[16] radiopaque medium,[15] sensitizer for orthochromatic photographic films, and visible light photoredox catalyst.[17]

Erythrosine is commonly used in sweets, such as some candies, ice pops and cherries, and in cake-decorating gels.[18] It was also used to color pistachio shells.[19] As a food additive, it has the E number E127.[20]

Safety assessment and regulation

Laboratory studies in the late 20th century suggested that "chronic erythrosine ingestion may promote thyroid tumor formation in rats via chronic stimulation of the thyroid by TSH" at concentrations of 4% erythrosine.[21][22] Toxicology tests combined with a review of other reported studies concluded that erythrosine is non-genotoxic and any tumor growth results from a non-genotoxic mechanism.[18][23]

In the United States, laboratory evidence of carcinogenicity of extremely high doses of erythrosine renders it as "unsafe" under federal law by a provision called the Delaney Clause, despite conclusions by the federal Center for Food Safety and Applied Nutrition and Cancer Assessment Committee that the risk of developing cancer in humans is unlikely at the low erythrosine levels consumed as a food color.[18][24]

Throughout the early 21st century, the World Health Organization and several national food safety agencies permitted use of erythrosine as a color additive when used in amounts below acceptable daily intake levels for certain foods, such as for packaged cherries; countries having restricted-use provisions were the European Union, United States, Canada, and Australia/New Zealand.[20][24][25][26][27]

Since 1994,[28] the European Food Safety Authority has only allowed erythrosine in processed cherries,[20] pet foods,[29][30] and up to 25 ppm in toothpaste.[31] In the United Kingdom, it is also allowed for coloring eggshells. It may not be sold directly to consumers.[32]

In the United States, the use of erythrosine in cosmetics, topical drugs, some foods, and in all uses as its lake variant have been banned by the Food and Drug Administration (FDA) since 1990.[33] In January 2025, the FDA banned the use of erythrosine in all foods and ingested drugs, with enforcement beginning on 15 January 2027 and 18 January 2028, respectively.[18] An October 2023 bill passed in the state of California also banned the use of erythrosine in foods (along with brominated vegetable oil, potassium bromate, and propylparaben), with enforcement beginning on 1 January 2027.[34]

In 2025, Health Canada stated that erythrosine "does not pose a health risk to the general Canadian population at the levels set out in the List of Permitted Food Colours."[26]

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 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; Spiro[isobenzofuran- 1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt.[2]

Classification

It is listed under the following number systems:

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Erythrosine B product description". The Chemical Book.
  2. ^ a b c Page Module:Citation/CS1/styles.css has no content."Erythrosine sodium anhydrous". PubChem, US National Library of Medicine. 11 January 2025. Retrieved 17 January 2025.
  3. ^ Script error: No such module "Template wrapper".
  4. ^ Page Module:Citation/CS1/styles.css has no content.Le Moniteur scientifique du Docteur Quesneville: journal des sciences pures et appliquées (in français). Le Moniteur scientifique. 1878. p. 1171.
  5. ^ Page Module:Citation/CS1/styles.css has no content.A Dictionary of the Coal Tar Colours. Heywood and Company. 1892. p. 48.
  6. ^ Page Module:Citation/CS1/styles.css has no content."Erythrosine - CAMEO". cameo.mfa.org. Retrieved 21 December 2025.
  7. ^ Page Module:Citation/CS1/styles.css has no content."Dye - Synthetic, Organic, Colorants | Britannica". Encyclopedia Britannica. Archived from the original on 9 August 2025. Retrieved 21 December 2025.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Deshpande, S. S. (29 August 2002). Handbook of Food Toxicology. CRC Press. p. 227. ISBN 978-0-203-90896-9.
  9. ^ Page Module:Citation/CS1/styles.css has no content.The Emergency Tariff and Its Effect on Cattle and Beef, Sheep and Mutton, Wool, Pork, and Miscellaneous Meats. U.S. Government Printing Office. 1922.
  10. ^ Page Module:Citation/CS1/styles.css has no content.United States Tariff Commission (1925). Census of Dyes and Other Synthetic Organic Chemicals. Tariff Information Series. Washington, D.C.: Government Printing Office. p. 64. Retrieved 17 January 2025.
  11. ^ Template:Cite periodical
  12. ^ Page Module:Citation/CS1/styles.css has no content.Gunther, Francis A. (11 May 1983). Residue Reviews: Residues of Pesticides and Other Contaminants in the Total Environment. Springer New York. ISBN 978-0-387-90851-9.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Chequer FM, Venâncio VP, Bianchi ML, Antunes LM (October 2012). "Genotoxic and mutagenic effects of erythrosine B, a xanthene food dye, on HepG2 cells". Food and Chemical Toxicology. 50 (10): 3447–51. doi:10.1016/j.fct.2012.07.042. PMID 22847138.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Gurr E (2012). Synthetic Dyes in Biology, Medicine And Chemistry. elsevier. pp. 197, 198.
  15. ^ a b Page Module:Citation/CS1/styles.css has no content.Dictionary of Analytical Reagents. CRC Press. 1993. p. 474. ISBN 978-0-412-35150-1.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Wood S, Metcalf D, Devine D, Robinson C (April 2006). "Erythrosine is a potential photosensitizer for the photodynamic therapy of oral plaque biofilms". The Journal of Antimicrobial Chemotherapy. 57 (4): 680–4. doi:10.1093/jac/dkl021. PMID 16464894.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Rogers DA, Brown RG, Brandeburg ZC, Ko EY, Hopkins MD, LeBlanc G, Lamar AA (October 2018). "Organic Dye-Catalyzed, Visible-Light Photoredox Bromination of Arenes and Heteroarenes Using N-Bromosuccinimide". ACS Omega. 3 (10): 12868–12877. doi:10.1021/acsomega.8b02320. PMC 6644467. PMID 31458011.
  18. ^ a b c d Page Module:Citation/CS1/styles.css has no content."FD&C Red No. 3". US Food and Drug Administration. 15 January 2025. Archived from the original on 18 January 2024. Retrieved 15 January 2025.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Day, Chris (16 January 2023). "The Almost-Forgotten Era Of Red Pistachios". The Daily Meal. Retrieved 17 November 2023.
  20. ^ a b c Page Module:Citation/CS1/styles.css has no content.EFSA Panel on Additives and Products or Substances used in Animal Feed (January 2011). "Scientific Opinion on the re-evaluation of Erythrosine (E 127) as a food additive". EFSA Journal. 9 (1): 1854. doi:10.2903/j.efsa.2011.1854. Erythrosine is exclusively authorised for use in cocktail and candied cherries, and Bigarreaux cherries
  21. ^ Page Module:Citation/CS1/styles.css has no content.Jennings AS, Schwartz SL, Balter NJ, Gardner D, Witorsch RJ (May 1990). "Effects of oral erythrosine (2′,4′,5′,7′-tetraiodofluorescein) on the pituitary-thyroid axis in rats". Toxicology and Applied Pharmacology. 103 (3): 549–56. doi:10.1016/0041-008x(90)90327-q. PMID 2160137.
  22. ^ Page Module:Citation/CS1/styles.css has no content.Borzelleca JF, Capen CC, Hallagan JB (October 1987). "Lifetime toxicity/carcinogenicity study of FD & C Red No. 3 (erythrosine) in rats". Food and Chemical Toxicology. 25 (10): 723–33. doi:10.1016/0278-6915(87)90226-2. PMID 2824305.
  23. ^ Page Module:Citation/CS1/styles.css has no content.Lin GH, Brusick DJ (July 1986). "Mutagenicity studies on FD&C red No.3". Mutagenesis. 1 (4): 253–9. doi:10.1093/mutage/1.4.253. PMID 2457780.
  24. ^ a b Page Module:Citation/CS1/styles.css has no content."Color Additive Petition From Center for Science in the Public Interest, et al.; Request To Revoke Color Additive Listing for Use of FD&C Red No. 3 in Food and Ingested Drugs". Federal Register, US Food and Drug Administration. 15 January 2025. Retrieved 17 January 2025.
  25. ^ Page Module:Citation/CS1/styles.css has no content."FD and C RED No. 3". Joint FAO/WHO Expert Committee on Food Additives, World Health Organization. 2018. Retrieved 17 January 2025.
  26. ^ a b Page Module:Citation/CS1/styles.css has no content."Red dye No. 3 banned from foods, U.S. regulator says". CBC News. The Associated Press. 15 January 2025. Retrieved 17 January 2025.
  27. ^ Page Module:Citation/CS1/styles.css has no content."Australia New Zealand Food Standards Code – Schedule 8 – Food additive names and code numbers (for statement of ingredients)". Office Parliamentary Counsel; Locked Bag 30 Kingston ACT 2604, Food Standards Australia New Zealand. 26 March 2021. Retrieved 19 September 2024.
  28. ^ Page Module:Citation/CS1/styles.css has no content.European Parliament and Council Directive 94/36/EC of 30 June 1994 on colours for use in foodstuffs, vol. 237, 30 June 1994, retrieved 16 January 2025
  29. ^ Page Module:Citation/CS1/styles.css has no content.EFSA Panel on Additives and Products or Substances used in Animal Feed (2015). "Update of the Scientific Opinion on the safety and efficacy of erythrosine in feed for cats, dogs, reptiles and ornamental fish". EFSA Journal. 13 (9): 4233. doi:10.2903/j.efsa.2015.4233. hdl:2434/559021.
  30. ^ Page Module:Citation/CS1/styles.css has no content.EFSA Panel on Additives and Products or Substances used in Animal Feed (2019). "Safety of erythrosine for ornamental fish". EFSA Journal. 17 (5): 5699. doi:10.2903/j.efsa.2019.5699. PMC 7009114. PMID 32626322.
  31. ^ Page Module:Citation/CS1/styles.css has no content.SCCS (Scientific Committee on Consumer Safety) (22 January 2010). Opinion on CI 45 430 (erythrosine) (PDF) (Report). European Commission. doi:10.2772/24102. ISBN 978-92-79-12741-0. ISSN 1831-4767. ND-AQ-09-013-EN-N.
  32. ^ Page Module:Citation/CS1/styles.css has no content.Chappell, Bill (15 October 2021). "'Sprinklegate' sinks a U.K. Bakery's top sellers after topping is found to be illegal". NPR. Retrieved 20 January 2025.
  33. ^ Page Module:Citation/CS1/styles.css has no content."FDA Bans Some Uses of Red No. 3 Additive". Los Angeles Times. Associated Press. 29 January 1990. Retrieved 15 January 2025.
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