Erythrosine

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Erythrosine
Erythrosine Erythrosine.svg
Erythrosine
Names
IUPAC name
2-(6-Hydroxy-2,4,5,7-tetraiodo-3-oxo-xanthen-9-yl)benzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.036.390 OOjs UI icon edit-ltr-progressive.svg
E number E127 (colours)
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: OALHHIHQOFIMEF-UHFFFAOYSA-N Yes check.svgY
  • 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
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
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 ?)

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]

Contents

History

The colorant was discovered by Swiss chemist Karl Kussmaul at the University of Basel in 1876 and soon commercialized by local Bindschedler & Busch company for dyeing wool and silk. [4] [5]

Its use as a food dye was legalized in the US by the Pure Food and Drug Act of 1906. [6] By early 1920s, it was produced mainly for the food industry, [7] with 2,170 pounds (0.98 t) made in America in 1924, [8] rising to 9,468 pounds (4.29 t) in 1938 [9] and approximately 50 tons in 1967. [10]

Production

Erythrosine is synthesized from phenol 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, [11] printing ink, [12] biological stain, [13] dental plaque disclosing agent, [14] radiopaque medium, [13] sensitizer for orthochromatic photographic films, and visible light photoredox catalyst. [15]

Erythrosine is commonly used in sweets, such as some candies, ice pops and cherries, and in cake-decorating gels. [16] It was also used to color pistachio shells. [17] As a food additive, it has the E number E127. [18]

Safety assessment and regulation

Concerns were raised by laboratory studies in the late 20th century that "chronic erythrosine ingestion may promote thyroid tumor formation in rats via chronic stimulation of the thyroid by TSH" occurring with 4% erythrosine. [19] [20] 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. [16] [21]

In the United States, laboratory evidence of carcinogenicity by 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. [16] [22]

Throughout the early 21st century, the World Health Organization and several national food safety agencies permitted use of erythrosine as a color additive under restrictions that it be 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. [18] [22] [23] [24] [25]

Since 1994, [26] the European Food Safety Authority only allows erythrosine in processed cherries [18] and pet foods. [27] [28] It is also allowed in toothpaste up to 25 ppm. [29] In the United Kingdom, erythrosine is also allowed for coloring eggshells. It is not permitted to be sold directly to consumers. [30]

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. [31] 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. [16] 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. [32]

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." [24]

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:

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References

  1. ↑ "Erythrosine B product description". The Chemical Book.
  2. 1 2 3 "Erythrosine sodium anhydrous". PubChem, US National Library of Medicine. 11 January 2025. Retrieved 17 January 2025.
  3. ↑ Lyday, Phyllis A; Kaiho, Tatsuo. "Iodine and Iodine Compounds". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_381.pub2. ISBN   978-3-527-30673-2.
  4. ↑ Le Moniteur scientifique du Docteur Quesneville: journal des sciences pures et appliquées (in French). Le Moniteur scientifique. 1878. p. 1171.
  5. ↑ A Dictionary of the Coal Tar Colours. Heywood and Company. 1892. p. 48.
  6. ↑ Deshpande, S. S. (29 August 2002). Handbook of Food Toxicology. CRC Press. p. 227. ISBN   978-0-203-90896-9.
  7. ↑ The Emergency Tariff and Its Effect on Cattle and Beef, Sheep and Mutton, Wool, Pork, and Miscellaneous Meats. U.S. Government Printing Office. 1922.
  8. ↑ 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.
  9. ↑ Taylor, J.N. (13 July 1940). "Organic Chemicals". World Trade Notes on Chemicals and Allied Products. Vol. 14, no. 28. Washington, D.C.: Department of Commerce Chemical Division. p. 456. Retrieved 17 January 2025.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ Gurr E (2012). Synthetic Dyes in Biology, Medicine And Chemistry. elsevier. pp. 197, 198.
  13. 1 2 Dictionary of Analytical Reagents. CRC Press. 1993. p. 474. ISBN   978-0-412-35150-1.
  14. ↑ 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.
  15. ↑ 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.
  16. 1 2 3 4 "FD&C Red No. 3". US Food and Drug Administration. 15 January 2025. Retrieved 15 January 2025.
  17. ↑ Day, Chris (16 January 2023). "The Almost-Forgotten Era Of Red Pistachios". The Daily Meal. Retrieved 17 November 2023.
  18. 1 2 3 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
  19. ↑ 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.
  20. ↑ 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.
  21. ↑ 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.
  22. 1 2 "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.
  23. ↑ "FD and C RED No. 3". Joint FAO/WHO Expert Committee on Food Additives, World Health Organization. 2018. Retrieved 17 January 2025.
  24. 1 2 "Red dye No. 3 banned from foods, U.S. regulator says". CBC News. The Associated Press. 15 January 2025. Retrieved 17 January 2025.
  25. ↑ "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.
  26. ↑ 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
  27. ↑ 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 .
  28. ↑ 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.
  29. ↑ 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.
  30. ↑ 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.
  31. ↑ "FDA Bans Some Uses of Red No. 3 Additive". Los Angeles Times . Associated Press. 29 January 1990. Retrieved 15 January 2025.
  32. ↑ Gabriel, Jesse; et al. (2023) [Approved by Governor 7 October 2023]. The California Food Safety Act (AB 418). California State Legislature.
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