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Allura Red AC

April 12, 2024

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

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.

Allura Red AC
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
  • 25956-17-6 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL174821 N
ChemSpider
  • 11588224 Y
ECHA InfoCard 100.043.047
E number E129 (colours)
  • 6093299
UNII
  • WZB9127XOA Y
  • DTXSID4024436
  • 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+;; Y
    Key: CEZCCHQBSQPRMU-LLIZZRELSA-L Y
  • 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)
Health 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 YN ?)

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 edit

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 edit

 
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 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]

References edit

  1. ^ . Archived from the original on 15 January 2008. Retrieved 4 June 2008. . 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. ^ a b c d e f FDA (30 March 2011). (PDF). Food and Drug Administration. Archived from the original (PDF) on 2 May 2017.
  11. ^ 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]
  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. ^ a b "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. ^ . 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.

External links edit

  • Allura Red AC on PubChem
  • International Programme on Chemical Safety
  • List of Foods and Drugs containing Red Dye #40

April 12, 2024
allura, e129, redirects, here, train, e129, series, that, goes, several, names, including, used, food, number, e129, namespreferred, iupac, name, disodium, hydroxy, methoxy, methyl, sulfonatophenyl, diazenyl, naphthalene, sulfonateother, names, disodium, hydro. E129 redirects here For the train see E129 series Allura Red AC is a red azo dye that goes by several names including FD amp C Red 40 1 It is used as a food dye and has the E number E129 Allura Red AC NamesPreferred IUPAC name Disodium 7 hydroxy 5 2 methoxy 5 methyl 4 sulfonatophenyl diazenyl naphthalene 2 sulfonateOther names Disodium 6 hydroxy 5 2 methoxy 5 methyl 4 sulfophenyl azo 2 naphthalenesulfonateAllura RedFood Red 17C I 16035FD amp C Red 40E1402 Naphthalenesulfonic acid 6 hydroxy 5 2 methoxy 5 methyl 4 sulfophenyl azo disodium saltIdentifiersCAS Number 25956 17 6 Y3D model JSmol Interactive imageChEMBL ChEMBL174821 NChemSpider 11588224 YECHA InfoCard 100 043 047E number E129 colours PubChem CID 6093299UNII WZB9127XOA YCompTox Dashboard EPA DTXSID4024436InChI 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 YKey CEZCCHQBSQPRMU LLIZZRELSA L YInChI 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 JGGVBICHBNSMILES Na Na COc3cc c C cc3 N N c1c2ccc cc2ccc1O S O O O S O O OPropertiesChemical formula C 18H 14N 2Na 2O 8S 2Molar mass 496 42 g mol 1Appearance Red powderMelting point gt 300 C 572 F 573 K HazardsNFPA 704 fire diamond 110Except 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 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 amp 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 Contents 1 Use as a consumable coloring agent 2 Studies on safety 3 References 4 External linksUse as a consumable coloring agent editAllura 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 edit nbsp Allura Red AC in strawberry soft drink nbsp Allura Red AC in confectioneryAllura 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 References edit 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 Zvi Rappoport ed 2004 The Chemistry of Phenols Chichester John Wiley amp Sons ISBN 9780470869451 PubChem Allura Red AC pubchem ncbi nlm nih gov Retrieved 21 October 2021 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 Human Metabolome Database Showing metabocard for Allura red AC HMDB0032884 Human Metabolome Database 11 September 2012 Retrieved 22 November 2022 European Parliament and Council Directive 94 36 EC of 30 June 1994 on colours for use in foodstuffs FD amp C Red No 40 Inactive Ingredient drugs com Retrieved 12 November 2023 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 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 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 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 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 a b Refined exposure assessment for Allura Red AC E 129 European Food Efsa europa eu 13 February 2015 Retrieved 8 September 2018 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 Food additives EU Framework Archived from the original on 6 February 2024 Retrieved 6 March 2024 Norwegian Food Safety Authority Archived from the original on 4 August 2012 Retrieved 9 July 2007 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 External links editAllura Red AC on PubChem International Programme on Chemical Safety List of Foods and Drugs containing Red Dye 40 Retrieved from https en wikipedia org w index php title Allura Red AC amp oldid 1215582675, wikipedia, wiki, book, books, library,

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