Allura Red AC

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"E129" redirects here. For the train, see E129 series.

Allura Red AC
File:Allura Red AC Structural Formula V1.svg
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
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UNII
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  • 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)

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1
1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 

Production

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Allura Red AC is manufactured by azo coupling between diazotized cresidinesulfonic acid and 2-naphthol-6-sulfonic acid.[4] Nitrosamines (like NDMA) are usually not tested in batches of food dyes, even though they're a known risk in diazotization chemistry.

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 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] until subsequent changes in the 2000s. 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, candy, cherry-flavored products, children's medications, and dairy products. It is occasionally used to dye medicinal tablets to help with identification, such as with fexofenadine, an antihistamine.[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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File:Strawberry soda.jpg
Allura Red AC is the coloring additive in this strawberry soft drink.
File:Sweet allura red close.jpg
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, dubbed the "Southampton 6" (tartrazine, Allura Red, Ponceau 4R, Quinoline Yellow, sunset yellow, carmoisine), 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. 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, Germany, Austria, 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]

In April 2025, the US FDA officially announced its plan to phase out Allura Red AC along with other petroleum-based dyes by the end of the year as part of the administration and Health and Human Services Secretary Robert F. Kennedy Jr.'s Make America Healthy Again initiative. [20]

References

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  7. ^ European Parliament and Council Directive 94/36/EC of 30 June 1994 on colours for use in foodstuffs
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  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
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