Chemistry:Allura Red AC

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Allura Red AC
Allura Red AC Structural Formula V1.svg
Names
Preferred IUPAC name
Disodium 7-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
E140
2-Naphthalenesulfonic acid, 6-hydroxy-5-((2-methoxy-5-methyl-4-sulfophenyl)azo)-, disodium salt
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
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)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
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 ☑Y☒N ?)
Infobox references

Allura Red AC is a red azo dye that goes by several names, including FD&C Red 40.[1] It is used as a food dye and has the E number E129.

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.[2]:921

Allura Red, FD&C Red No. 40 is manufactured by coupling diazotized 5-amino-4-methoxy-2-toluenesulfonic acid with 6-hydroxy-2-naphthalene sulfonic acid in an azo coupling reaction.[3]

Use as a consumable coloring agent

Allura Red AC is a popular dye used worldwide. Annual production in 1980 was greater than 2.3 million kilograms.[4] It was originally introduced as a replacement for amaranth in the United States.[5]

The European Union approves Allura Red AC as a food colorant, but EU countries' local laws banning food colorants are preserved.[6] 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.[7] It is by far the most commonly used red dye in the United States,[8] completely replacing amaranth (Red 2) and also replacing erythrosine (Red 3) in most applications due to the negative health effects of those two dyes.[9]

Studies on safety

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.

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.[10][11] The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children;[10][11] 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.[10]

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.[10][11] 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",[10] and in 2014, after further review of the data, the EFSA restored the prior ADI levels.[12] In 2015, the EFSA found that the exposure estimates did not exceed the ADI of 7 mg/kg per day in any population.[13]

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.[10]

Allura Red AC is banned in Denmark , Belgium, France , Switzerland , and Sweden.[14] 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.[15] Chronic exposure to the dye has been shown to increase susceptibility to bowel disorders in mice. [16]

References

  1. ↑ "From Shampoo to Cereal: Seeing to the Safety of Color Additives". http://www.cfsan.fda.gov/~dms/col-221.html.  "Food Color Facts". http://www.cfsan.fda.gov/~lrd/colorfac.html. 
  2. ↑ Zvi Rappoport, ed (2004). The Chemistry of Phenols. Chichester: John Wiley & Sons. ISBN 9780470869451. 
  3. ↑ PubChem. "Allura Red AC" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/33258. 
  4. ↑ 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. doi:10.1021/ed100545v. Bibcode: 2011JChEd..88...24S. 
  5. ↑ "Human Metabolome Database: Showing metabocard for Allura red AC (HMDB0032884)". 2012-09-11. https://hmdb.ca/metabolites/HMDB0032884. 
  6. ↑ European Parliament and Council Directive 94/36/EC of 30 June 1994 on colours for use in foodstuffs
  7. ↑ "FD&C Red No. 40 (Inactive Ingredient)". drugs.com. https://www.drugs.com/inactive/fd-c-red-no-40-251.html. 
  8. ↑ Zhang, Qi; Chumanevich, Alexander A.; Nguyen, Ivy; Chumanevich, Anastasiya A.; Sartawi, Nora; Hogan, Jake; Khazan, Minou; Harris, Quinn et al. (2023). "The synthetic food dye, Red 40, causes DNA damage, causes colonic inflammation, and impacts the microbiome in mice". Toxicology Reports 11: 221–232. doi:10.1016/j.toxrep.2023.08.006. ISSN 2214-7500. PMID 37719200. 
  9. ↑ 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. PMID 27303385. 
  10. ↑ 10.0 10.1 10.2 10.3 10.4 10.5 FDA (March 30, 2011). "Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children:date". https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248549.pdf. 
  11. ↑ 11.0 11.1 11.2 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]
  12. ↑ 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
  13. ↑ "Refined exposure assessment for Allura Red AC (E 129) | European Food". Efsa.europa.eu. 13 February 2015. http://www.efsa.europa.eu/en/efsajournal/pub/4007. 
  14. ↑ Esmaeili, Sajjad; Ashrafi-Kooshk, Mohammad Reza; Khaledian, Koestan; Adibi, Hadi; Rouhani, Shohre; Khodarahmi, Reza (2016-12-15). "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. https://www.sciencedirect.com/science/article/pii/S0308814616309712. 
  15. ↑ "Norwegian Food Safety Authority". http://www.mattilsynet.no/mat/mattrygghet/tilsetningsstoffer/norway_and_food_additives_34434. 
  16. ↑ Kwon, Yun Han; Banskota, Suhrid; Wang, Huaqing; Rossi, Laura; Grondin, Jensine A.; Syed, Saad A.; Yousefi, Yeganeh; Schertzer, Jonathan D. et al. (2022-12-20). "Chronic exposure to synthetic food colorant Allura Red AC promotes susceptibility to experimental colitis via intestinal serotonin in mice" (in en). Nature Communications 13 (1): 7617. doi:10.1038/s41467-022-35309-y. ISSN 2041-1723. PMID 36539404. Bibcode: 2022NatCo..13.7617K. 

External links



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