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Allura Red AC

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(Redirected from C18H14N2Na2O8S2)
"E129" redirects here. For the train, see E129 series.

Allura Red AC
Names
Preferred IUPAC name
Disodium 6-hydroxy-5-[(2-methoxy-5-methyl-4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate
Other names
  • Disodium 6-hydroxy-5-[(2-methoxy-5-methyl-4-sulfophenyl)azo]-2-naphthalenesulfonate
  • Allura Red
  • Food Red 17
  • C.I. 16035
  • FD&C Red 40
  • E129
  • 2-Naphthalenesulfonic acid, 6-hydroxy-5-((2-methoxy-5-methyl-4-sulfophenyl)azo)-, disodium salt
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.043.047 Edit this at Wikidata
E number E129 (colours)
UNII
  • InChI=1S/C18H16N2O8S2.2Na/c1-10-7-14(16(28-2)9-17(10)30(25,26)27)19-20-18-13-5-4-12(29(22,23)24)8-11(13)3-6-15(18)21;;/h3-9,21H,1-2H3,(H,22,23,24)(H,25,26,27);;/q;2*+1/p-2/b20-19+;; checkY
    Key: CEZCCHQBSQPRMU-LLIZZRELSA-L checkY
  • InChI=1/C18H16N2O8S2.2Na/c1-10-7-14(16(28-2)9-17(10)30(25,26)27)19-20-18-13-5-4-12(29(22,23)24)8-11(13)3-6-15(18)21;;/h3-9,21H,1-2H3,(H,22,23,24)(H,25,26,27);;/q;2*+1/p-2/b20-19+;;
    Key: CEZCCHQBSQPRMU-JGGVBICHBN
  • [Na+].[Na+].COc3cc(c(C)cc3/N=N/c1c2ccc(cc2ccc1O)S([O-])(=O)=O)S([O-])(=O)=O
Properties
C18H14N2Na2O8S2
Molar mass 496.42 g·mol−1
Appearance Red powder
Melting point > 300 °C (572 °F; 573 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Allura Red AC, also known as FD&C Red 40 or E129, is a red azo dye commonly used in food. It was developed in 1971 by the Allied Chemical Corporation, who gave the substance its name.[1][2]

It is usually supplied as its red sodium salt but can also be used as the calcium and potassium salts. These salts are soluble in water. In solution, its maximum absorbance lies at about 504 nm.[3]: 921 

Allura Red AC is manufactured by coupling diazotized 5-amino-4-methoxy-2-toluenesulfonic acid with 6-hydroxy-2-naphthalene sulfonic acid in an azo coupling reaction.[4]

Use as a consumable coloring agent

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Allura Red AC is a popular dye used worldwide. Annual production in 1980 was greater than 2.3 million kilograms.[5] It was originally introduced as a replacement for amaranth in the United States.[6]

The European Union approved Allura Red AC as a food colorant in 1994, but EU countries' local laws banning food colorants were preserved.[7] In the United States, Allura Red AC is approved by the FDA for use in cosmetics, drugs, and food. When prepared as a lake pigment it is disclosed as Red 40 Lake or Red 40 Aluminum Lake. It is used in some tattoo inks and is used in many products, such as cotton candy, soft drinks, cherry-flavored products, children's medications, and dairy products. It is occasionally used to dye medicinal pills, such as the antihistamine fexofenadine, for purely aesthetic reasons.[8] It is by far the most commonly used red dye in the United States,[9] completely replacing amaranth (Red 2) and also replacing erythrosine (Red 3) in most applications due to the negative health effects of those two dyes.[10]

Studies on safety

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Allura Red AC in strawberry soft drink
Allura Red AC in confectionery

Allura Red has been heavily studied by food safety groups in North America and Europe, and remains in wide use. However, chronic exposure to the dye has been shown to increase susceptibility to bowel disorders in mice.[11] The dye has been shown to damage the DNA of mice.[12]

The UK's Food Standards Agency commissioned a study of six food dyes (tartrazine, Allura red, Ponceau 4R, Quinoline Yellow, sunset yellow, carmoisine (dubbed the "Southampton 6")), and sodium benzoate (a preservative) on children in the general population, who consumed them in beverages.[13][14] The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children;[13][14] the advisory committee to the FSA that evaluated the study also determined that because of study limitations, the results could not be extrapolated to the general population, and further testing was recommended.[13]

The European Food Safety Authority (EFSA), with a stronger emphasis on the precautionary principle, required labelling and temporarily reduced the acceptable daily intake (ADI) for the food colorings; the UK FSA called for voluntary withdrawal of the colorings by food manufacturers.[13][14] However, in 2009, the EFSA re-evaluated the data at hand and determined that "the available scientific evidence does not substantiate a link between the color additives and behavioral effects",[13] and in 2014, after further review of the data, the EFSA restored the prior ADI levels.[15] In 2015, the EFSA found that the exposure estimates did not exceed the ADI of 7 mg/kg per day in any population.[16]

The US FDA did not make changes following the publication of the Southampton study, but following a citizen petition filed by the Center for Science in the Public Interest in 2008, requesting the FDA ban several food additives, the FDA commenced a review of the available evidence, but found no evidence to justify changes.[13]

Allura Red AC has previously been banned in Denmark, Belgium, France, Switzerland, and Sweden.[17] This changed in 2008, when the EU adopted a common framework for authorizing food additives,[18] under which Allura Red AC is not currently banned.[16] In Norway and Iceland, it was banned between 1978 and 2001, a period in which azo dyes were only legally used in alcoholic beverages and some fish products.[19]

References

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  1. ^ "From Shampoo to Cereal: Seeing to the Safety of Color Additives". Archived from the original on 15 January 2008. Retrieved 4 June 2008. "Food Color Facts". Archived from the original on 1 October 2007. Retrieved 18 August 2006.
  2. ^ Barrows, Julie N. (2016). Wallin, Harriet (ed.). "Allura Red AC". 82nd Joint FAO/WHO Expert Committee on Food Additives (JECFA) - Chemical and Technical Assessment (CTA) – via Food and Agriculture Organization of the United Nations.
  3. ^ Zvi Rappoport, ed. (2004). The Chemistry of Phenols. Chichester: John Wiley & Sons. ISBN 9780470869451.
  4. ^ PubChem. "Allura Red AC". pubchem.ncbi.nlm.nih.gov. Retrieved 21 October 2021.
  5. ^ Sharma, Vinita; McKone, Harold T.; Markow, Peter G. (2011). "A Global Perspective on the History, Use, and Identification of Synthetic Food Dyes". Journal of Chemical Education. 88 (1): 24–28. Bibcode:2011JChEd..88...24S. doi:10.1021/ed100545v.
  6. ^ "Human Metabolome Database: Showing metabocard for Allura red AC (HMDB0032884)". Human Metabolome Database. 11 September 2012. Retrieved 22 November 2022.
  7. ^ European Parliament and Council Directive 94/36/EC of 30 June 1994 on colours for use in foodstuffs
  8. ^ "FD&C Red No. 40 (Inactive Ingredient)". drugs.com. Retrieved 12 November 2023.
  9. ^ Zhang, Qi; Chumanevich, Alexander A.; Nguyen, Ivy; Chumanevich, Anastasiya A.; Sartawi, Nora; Hogan, Jake; Khazan, Minou; Harris, Quinn; Massey, Bryson; Chatzistamou, Ioulia; Buckhaults, Phillip J.; Banister, Carolyn E.; Wirth, Michael; Hebert, James R.; Murphy, E. Angela (2023). "The synthetic food dye, Red 40, causes DNA damage, causes colonic inflammation, and impacts the microbiome in mice". Toxicology Reports. 11: 221–232. Bibcode:2023ToxR...11..221Z. doi:10.1016/j.toxrep.2023.08.006. ISSN 2214-7500. PMC 10502305. PMID 37719200.
  10. ^ Rovina, Kobun; Siddiquee, Shafiquzzaman; Shaarani, Sharifudin M. (2016). "Extraction, Analytical and Advanced Methods for Detection of Allura Red AC (E129) in Food and Beverages Products". Frontiers in Microbiology. 7: 798. doi:10.3389/fmicb.2016.00798. ISSN 1664-302X. PMC 4882322. PMID 27303385.
  11. ^ Kwon, Yun Han; Banskota, Suhrid; Wang, Huaqing; Rossi, Laura; Grondin, Jensine A.; Syed, Saad A.; Yousefi, Yeganeh; Schertzer, Jonathan D.; Morrison, Katherine M.; Wade, Michael G.; Holloway, Alison C.; Surette, Michael G.; Steinberg, Gregory R.; Khan, Waliul I. (20 December 2022). "Chronic exposure to synthetic food colorant Allura Red AC promotes susceptibility to experimental colitis via intestinal serotonin in mice". Nature Communications. 13 (1): 7617. Bibcode:2022NatCo..13.7617K. doi:10.1038/s41467-022-35309-y. ISSN 2041-1723. PMC 9768151. PMID 36539404.
  12. ^ Zhang, Qi; Chumanevich, Alexander; Nguyen, Ivy; Chumanevich, Anastasiya; Sartawi, Nora; Hogan, Jake; Khazan, Minou; Harris, Quinn; Massey, Bryson; Chatzistamou, Ioulia; Buckhaults, Phillip; Banister, Carolyn; Wirth, Michael; Herbert, James; Hofsetha, Lorne (19 March 2024). "The synthetic food dye, Red 40, causes DNA damage, causes colonic inflammation, and impacts the microbiome in mice". Toxicology Reports. 11: 221–232. Bibcode:2023ToxR...11..221Z. doi:10.1016/j.toxrep.2023.08.006. ISSN 0195-315X. PMC 10502305. PMID 37719200.
  13. ^ a b c d e f FDA (30 March 2011). "Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children:date" (PDF). Food and Drug Administration. Archived from the original (PDF) on 2 May 2017.
  14. ^ a b c Sarah Chapman of Chapman Technologies on behalf of Food Standards Agency in Scotland. March 2011 [Guidelines on approaches to the replacement of Tartrazine, Allura Red, Ponceau 4R, Quinoline Yellow, Sunset Yellow and Carmoisine in food and beverages]
  15. ^ EFSA Panel on Food Additives and Nutrient Sources added to food (ANS) Reconsideration of the temporary ADI and refined exposure assessment for Sunset Yellow FCF (E 110) EFSA Journal 2014;12(7):3765 . doi:10.2903/j.efsa.2014.3765
  16. ^ a b "Refined exposure assessment for Allura Red AC (E 129) | European Food". Efsa.europa.eu. 13 February 2015. Retrieved 8 September 2018.
  17. ^ Esmaeili, Sajjad; Ashrafi-Kooshk, Mohammad Reza; Khaledian, Koestan; Adibi, Hadi; Rouhani, Shohre; Khodarahmi, Reza (15 December 2016). "Degradation products of the artificial azo dye, Allura red, inhibit esterase activity of carbonic anhydrase II: A basic in vitro study on the food safety of the colorant in terms of enzyme inhibition". Food Chemistry. 213: 494–504. doi:10.1016/j.foodchem.2016.06.078. ISSN 0308-8146. PMID 27451209.
  18. ^ "Food additives - EU Framework". Archived from the original on 6 February 2024. Retrieved 6 March 2024.
  19. ^ "Norwegian Food Safety Authority". Archived from the original on 4 August 2012. Retrieved 9 July 2007.
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