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
  • 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 OOjs UI icon edit-ltr-progressive.svg
E number E129 (colours)
PubChem CID
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+;; Yes check.svgY
    Key: CEZCCHQBSQPRMU-LLIZZRELSA-L Yes check.svgY
  • 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
AppearanceRed powder
Melting point >300 °C (572 °F; 573 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 Strawberry soda.jpg
Allura Red AC in strawberry soft drink
Allura Red AC in confectionery 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.

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 has previously been banned in Denmark, Belgium, France, Switzerland, and Sweden. [14] This changed in 2008, when the EU adopted a common framework for authorising food additives, [15] under which Allura Red AC is not currently banned. [13] 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. [16] Chronic exposure to the dye has been shown to increase susceptibility to bowel disorders in mice. [17]

Related Research Articles

<span class="mw-page-title-main">Food coloring</span> Substance used to color food or drink

Food coloring, or color additive, is any dye, pigment, or substance that imparts color when it is added to food or drink. They can be supplied as liquids, powders, gels, or pastes. Food coloring is used in both commercial food production and domestic cooking. Food colorants are also used in a variety of non-food applications, including cosmetics, pharmaceuticals, home craft projects, and medical devices. Colorings may be natural or artificial/synthetic.

<span class="mw-page-title-main">Quinoline Yellow WS</span> "Mixture of water-soluble organic compounds from Quinoline Yellow dye"

Quinoline Yellow WS is a mixture of organic compounds derived from the dye Quinoline Yellow SS. Owing to the presence of sulfonate groups, the WS dyes are water-soluble (WS). It is a mixture of disulfonates (principally), monosulfonates and trisulfonates of 2-(2-quinolyl)indan-1,3-dione with a maximum absorption wavelength of 416 nm.p. 119

Carmine – also called cochineal, cochineal extract, crimson lake, or carmine lake – is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid. Specific code names for the pigment include natural red 4, C.I. 75470, or E120. Carmine is also a general term for a particularly deep-red color.

<span class="mw-page-title-main">Annatto</span> Orange-red condiment and food coloring derived from the seeds of the achiote tree

Annatto is an orange-red condiment and food coloring derived from the seeds of the achiote tree, native to tropical parts of the Americas. It is often used to impart a yellow to red-orange color to foods, but sometimes also for its flavor and aroma. Its scent is described as "slightly peppery with a hint of nutmeg" and flavor as "slightly nutty, sweet and peppery".

<span class="mw-page-title-main">Tartrazine</span> Chemical compound

Tartrazine is a synthetic lemon yellow azo dye primarily used as a food coloring. It is also known as E number E102, C.I. 19140, FD&C Yellow 5, Yellow 5 Lake, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatophenylazo)-5-pyrazolone-3-carboxylate.

<span class="mw-page-title-main">Sunset yellow FCF</span> Chemical compound used as colorant

Sunset yellow FCF is a petroleum-derived orange azo dye with a pH dependent maximum absorption at about 480 nm at pH 1 and 443 nm at pH 13 with a shoulder at 500 nm. When added to foods sold in the United States it is known as FD&C Yellow 6; when sold in Europe, it is denoted by E Number E110.

<span class="mw-page-title-main">Acid dye</span> Dye applied to low pH textile

An acid dye is a dye that is typically applied to a textile at low pH. They are mainly used to dye wool, not cotton fabrics. Some acid dyes are used as food colorants, and some can also be used to stain organelles in the medical field.

<span class="mw-page-title-main">Haw flakes</span> Confectionery

Haw flakes are Chinese sweets made from the fruit of the Chinese hawthorn. The pale/dark pink candy is usually formed into discs two millimeters thick, and packaged in cylindrical stacks with label art resemblant of Chinese fireworks. The sweet and tangy snack is usually served to guests along with tea or as a treat for children. It is sometimes consumed with bitter Chinese herbal medicine to aid digestion.

<span class="mw-page-title-main">Brilliant blue FCF</span> Chemical compound

Brilliant blue FCF is a synthetic organic compound used primarily as a blue colorant for processed foods, medications, dietary supplements, and cosmetics. It is classified as a triarylmethane dye and is known under various names, such as FD&C Blue No. 1 or acid blue 9. It is denoted by E number E133 and has a color index of 42090. It has the appearance of a blue powder and is soluble in water and glycerol, with a maximum absorption at about 628 nanometers. It is one of the oldest FDA-approved color additives and is generally considered nontoxic and safe.

<span class="mw-page-title-main">Erythrosine</span> Iodo-derivative of fluorone used as a pink dye

Erythrosine, also known as Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is a pink dye which is primarily used for food coloring. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation.

<span class="mw-page-title-main">Ponceau 4R</span> Chemical compound

Ponceau 4R is a synthetic colourant that may be used as a food colouring. It is denoted by E Number E124. Its chemical name is 1-(4-sulfo-1-napthylazo)-2-napthol-6,8-disulfonic acid, trisodium salt. Ponceau is the generic name for a family of azo dyes.

<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group but there are some that contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

<span class="mw-page-title-main">Sudan II</span> Chemical compound

Sudan II (Solvent Orange 7, C.I. 12140, C18H16N2O) is a lysochrome (fat-soluble dye) azo dye used for staining of triglycerides in frozen sections, and some protein bound lipids and lipoproteins on paraffin sections. It has the appearance of red powder with melting point 156–158 °C and maximum absorption at 493(420) nm.

<span class="mw-page-title-main">Azorubine</span> Chemical compound

Azorubine is an azo dye consisting of two naphthalene subunits. It is a red solid. It is mainly used in foods that are heat-treated after fermentation. It has E number E122.

<span class="mw-page-title-main">Amaranth (dye)</span> Chemical compound

Amaranth, FD&C Red No. 2, E123, C.I. Food Red 9, Acid Red 27, Azorubin S, or C.I. 16185 is a modified red azo dye used as a food dye and to color cosmetics. The name was taken from amaranth grain, a plant distinguished by its red color and edible protein-rich seeds.

The Feingold diet is an elimination diet initially devised by Benjamin Feingold following research in the 1970s that appeared to link food additives with hyperactivity; by eliminating these additives and various foods the diet was supposed to alleviate the condition.

<span class="mw-page-title-main">Ingredients of cosmetics</span> Ingredients used in makeup

Cosmetics ingredients come from a variety of sources but, unlike the ingredients of food, are often not considered by most consumers. Cosmetics often use vibrant colors that are derived from a wide variety of sources, ranging from crushed insects to rust.

Numerous governmental and non-governmental organizations have criticized the U. S. Food and Drug Administration for alleged excessive and/or insufficient regulation. The U.S. Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for the safety regulation of most types of foods, dietary supplements, drugs, vaccines, biological medical products, blood products, medical devices, radiation-emitting devices, veterinary products, and cosmetics. The FDA also enforces section 361 of the Public Health Service Act and the associated regulations, including sanitation requirements on interstate travel as well as specific rules for control of disease on products ranging from animals sold as pets to donations of human blood and tissue.

<span class="mw-page-title-main">Acid orange 20</span> Chemical compound

Acid orange 20 is an organic compound and an azo dye. It is one of the first water soluble dyes to be commercialized, and one of seven original food dyes allowed under the U.S. Pure Food and Drug Act of June 30, 1906. It is analyzed by HPLC.

References

  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. ↑ Zvi Rappoport, ed. (2004). The Chemistry of Phenols. Chichester: John Wiley & Sons. ISBN   9780470869451.
  3. ↑ PubChem. "Allura Red AC". pubchem.ncbi.nlm.nih.gov. Retrieved 21 October 2021.
  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. Bibcode:2011JChEd..88...24S. doi:10.1021/ed100545v.
  5. ↑ "Human Metabolome Database: Showing metabocard for Allura red AC (HMDB0032884)". Human Metabolome Database. 11 September 2012. Retrieved 22 November 2022.
  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. Retrieved 12 November 2023.
  8. ↑ 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. doi:10.1016/j.toxrep.2023.08.006. ISSN   2214-7500. PMC   10502305 . 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. PMC   4882322 . PMID   27303385.
  10. 1 2 3 4 5 6 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.
  11. 1 2 3 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. 1 2 "Refined exposure assessment for Allura Red AC (E 129) | European Food". Efsa.europa.eu. 13 February 2015. Retrieved 8 September 2018.
  14. ↑ 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.
  15. ↑ "Food additives - EU Framework". Archived from the original on 6 February 2024. Retrieved 6 March 2024.
  16. ↑ "Norwegian Food Safety Authority". Archived from the original on 4 August 2012. Retrieved 9 July 2007.
  17. ↑ 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.
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