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Revision as of 04:46, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475318953 of page Allura_Red_AC for the Chem/Drugbox validation project (updated: '').  Latest revision as of 09:43, 16 December 2024 edit 38.49.72.163 (talk) →Studies on safety: rmv improperly editorial "but" per MOS:OPEDTags: Mobile edit Mobile web edit 
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{{redirect|E129|the train|E129 series}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{use dmy dates |date=November 2023}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 454148548
| Watchedfields = changed
⚫ |ImageFile=Allura Red AC.png
⚫ | verifiedrevid = 477314436
|IUPACName=disodium 6-hydroxy-5-((2-methoxy-5-methyl-4-sulfophenyl)azo)-2-naphthalenesulfonate
⚫ |ImageFile=Allura Red AC Structural Formula V1.svg
|OtherNames=Allura Red, Food Red 17, C.I. 16035, FD&C Red 40, E129, 2-naphthalenesulfonic acid disodium salt
|ImageFile1=
|PIN = Disodium 6-hydroxy-5-naphthalene-2-sulfonate
|OtherNames={{Unbulleted list|Disodium 6-hydroxy-5--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}}
|Section1= {{Chembox Identifiers |Section1= {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WZB9127XOA | UNII = WZB9127XOA
| 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+;; | 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+;;
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=25956-17-6 | CASNo=25956-17-6
| EINECS= | EINECS=
| PubChem=6093299 | PubChem=6093299
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | SMILES = ..COc3cc(c(C)cc3/N=N/c1c2ccc(cc2ccc1O)S()(=O)=O)S()(=O)=O
| ChEMBL = 174821
⚫ | SMILES = ..COc3cc(c(C)cc3/N=N/c1c2ccc(cc2ccc1O)S()(=O)=O)S()(=O)=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=11588224 | ChemSpiderID=11588224
}} }}
|Section2= {{Chembox Properties |Section2= {{Chembox Properties
| C=18 | H=14 | N=2 | Na=2| O=8 | S=2 | C=18 | H=14 | N=2 | Na=2 | O=8 | S=2
| Appearance= red powder | Appearance= Red powder
| Density= | Density=
| MeltingPt= >300°C | MeltingPt= >
| MeltingPtC = 300
| BoilingPt=
| Solubility= | BoilingPt=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3= {{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
}} }}
}} }}
'''Allura Red AC''', also known as '''] Red 40''' or ''']129''', is a ] ] commonly used in food. It was developed in 1971 by the ], who gave the substance its name.<ref>{{cite web|url=http://www.cfsan.fda.gov/~dms/col-221.html |title=From Shampoo to Cereal: Seeing to the Safety of Color Additives |access-date=2008-06-04 |url-status=dead |archive-url=https://web.archive.org/web/20080115194446/http://www.cfsan.fda.gov/~dms/col-221.html |archive-date=2008-01-15 }}
{{cite web|url=http://www.cfsan.fda.gov/~lrd/colorfac.html |title=Food Color Facts |access-date=2006-08-18 |url-status=dead |archive-url=https://web.archive.org/web/20071001050645/http://www.cfsan.fda.gov/~lrd/colorfac.html |archive-date=2007-10-01 }}</ref><ref>{{Cite journal |last=Barrows |first=Julie N. |date=2016 |editor-last=Wallin |editor-first=Harriet |title=Allura Red AC |url=https://openknowledge.fao.org/server/api/core/bitstreams/c9b6bd7c-05d8-4de7-a816-6859bceef71b/content |journal=82nd Joint FAO/WHO Expert Committee on Food Additives (JECFA) - Chemical and Technical Assessment (CTA) |via=Food and Agriculture Organization of the United Nations}}</ref>

It is usually supplied as its red ] ] but can also be used as the ] and ] salts. These salts are soluble in ]. In ], its maximum ] lies at about 504&nbsp;nm.<ref>{{cite book|title=The Chemistry of Phenols|year=2004|publisher=John Wiley & Sons|location=Chichester|isbn=9780470869451|editor=Zvi Rappoport}}</ref>{{rp|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 ] reaction.<ref>{{Cite web|last=PubChem|title=Allura Red AC|url=https://pubchem.ncbi.nlm.nih.gov/compound/33258|access-date=2021-10-21|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>

==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.<ref>{{cite journal|title=A Global Perspective on the History, Use, and Identification of Synthetic Food Dyes|author1=Sharma, Vinita|author2=McKone, Harold T.|author3=Markow, Peter G.|journal=Journal of Chemical Education|year=2011|volume=88|issue=1 |pages=24–28|doi=10.1021/ed100545v|bibcode=2011JChEd..88...24S }}</ref> It was originally introduced as a replacement for ] in the United States.<ref name="Human Metabolome Database 2012">{{cite web | title=Human Metabolome Database: Showing metabocard for Allura red AC (HMDB0032884) | website=Human Metabolome Database | date=2012-09-11 | url=https://hmdb.ca/metabolites/HMDB0032884 | access-date=2022-11-22}}</ref>

The ] approved Allura Red AC as a food colorant in 1994, but EU countries' local laws banning food colorants were preserved.<ref>European Parliament and Council Directive 94/36/EC of 30 June 1994 on colours for use in foodstuffs</ref>
In the United States, Allura Red AC is approved by the FDA for use in ], drugs, and food. When prepared as a ] 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 ], ]s, ]-flavored products, children's medications, and ] products. It is occasionally used to dye medicinal pills, such as the ] ], for purely aesthetic reasons.<ref>{{Cite web|url=https://www.drugs.com/inactive/fd-c-red-no-40-251.html |work=drugs.com |access-date=12 November 2023 |title=FD&C Red No. 40 (Inactive Ingredient)}}</ref> It is by far the most commonly used red dye in the United States,<ref>{{Cite journal |last1=Zhang |first1=Qi |last2=Chumanevich |first2=Alexander A. |last3=Nguyen |first3=Ivy |last4=Chumanevich |first4=Anastasiya A. |last5=Sartawi |first5=Nora |last6=Hogan |first6=Jake |last7=Khazan |first7=Minou |last8=Harris |first8=Quinn |last9=Massey |first9=Bryson |last10=Chatzistamou |first10=Ioulia |last11=Buckhaults |first11=Phillip J. |last12=Banister |first12=Carolyn E. |last13=Wirth |first13=Michael |last14=Hebert |first14=James R. |last15=Murphy |first15=E. Angela |year=2023 |title=The synthetic food dye, Red 40, causes DNA damage, causes colonic inflammation, and impacts the microbiome in mice |journal=Toxicology Reports |volume=11 |pages=221–232 |doi=10.1016/j.toxrep.2023.08.006 |issn=2214-7500 |pmid=37719200|pmc=10502305 |bibcode=2023ToxR...11..221Z }}</ref> completely replacing ] and also replacing ] in most applications due to the negative health effects of those two dyes.<ref>{{Cite journal |last1=Rovina |first1=Kobun |last2=Siddiquee |first2=Shafiquzzaman |last3=Shaarani |first3=Sharifudin M. |date=2016 |title=Extraction, Analytical and Advanced Methods for Detection of Allura Red AC (E129) in Food and Beverages Products |journal=Frontiers in Microbiology |volume=7 |pages=798 |doi=10.3389/fmicb.2016.00798 |issn=1664-302X |pmc=4882322 |pmid=27303385 |doi-access=free }}</ref>

==Studies on safety==
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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.<ref>{{Cite journal |last1=Kwon |first1=Yun Han |last2=Banskota |first2=Suhrid |last3=Wang |first3=Huaqing |last4=Rossi |first4=Laura |last5=Grondin |first5=Jensine A. |last6=Syed |first6=Saad A. |last7=Yousefi |first7=Yeganeh |last8=Schertzer |first8=Jonathan D. |last9=Morrison |first9=Katherine M. |last10=Wade |first10=Michael G. |last11=Holloway |first11=Alison C. |last12=Surette |first12=Michael G. |last13=Steinberg |first13=Gregory R. |last14=Khan |first14=Waliul I. |date=2022-12-20 |title=Chronic exposure to synthetic food colorant Allura Red AC promotes susceptibility to experimental colitis via intestinal serotonin in mice |journal=] |language=en |volume=13 |issue=1 |pages=7617 |doi=10.1038/s41467-022-35309-y |pmid=36539404 |pmc=9768151 |bibcode=2022NatCo..13.7617K |issn=2041-1723|doi-access=free }}</ref> The dye has been shown to damage the DNA of mice.<ref>{{Cite journal |last1=Zhang |first1=Qi |last2=Chumanevich |first2=Alexander |last3=Nguyen |first3=Ivy |last4=Chumanevich |first4=Anastasiya |last5=Sartawi |first5=Nora |last6=Hogan |first6=Jake |last7=Khazan |first7=Minou |last8=Harris |first8=Quinn |last9=Massey |first9=Bryson |last10=Chatzistamou |first10=Ioulia |last11=Buckhaults |first11=Phillip |last12=Banister |first12=Carolyn |last13=Wirth |first13=Michael |last14=Herbert |first14=James |last15=Hofsetha |first15=Lorne |date=2024-03-19 |title=The synthetic food dye, Red 40, causes DNA damage, causes colonic inflammation, and impacts the microbiome in mice |volume=11 |pages=221–232 |journal=Toxicology Reports |language=English |doi=10.1016/j.toxrep.2023.08.006 |issn=0195-315X |doi-access=free|pmid=37719200 |pmc=10502305 |bibcode=2023ToxR...11..221Z }}</ref>

The UK's ] commissioned a study of six food dyes (], Allura red, ], ], ], ] (dubbed the "Southampton 6")), and ] (a preservative) on children in the general population, who consumed them in beverages.<ref name="FDAdyecomm">{{cite web|author=FDA|title=Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children:date|website=]|url=https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248549.pdf|url-status=dead|archive-url=https://web.archive.org/web/20170502145045/https://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248549.pdf|archive-date=2017-05-02|date=March 30, 2011}}</ref><ref name=FSAguideline>Sarah Chapman of Chapman Technologies on behalf of Food Standards Agency in Scotland. March 2011 </ref> The study found "a possible link between the consumption of these artificial colours and a sodium benzoate preservative and increased hyperactivity" in the children;<ref name=FDAdyecomm /><ref name=FSAguideline /> 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.<ref name=FDAdyecomm />

The ] (EFSA), with a stronger emphasis on the ], required labelling and temporarily reduced the ] (ADI) for the food colorings; the UK FSA called for voluntary withdrawal of the colorings by food manufacturers.<ref name=FDAdyecomm /><ref name=FSAguideline /> 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",<ref name=FDAdyecomm /> and in 2014, after further review of the data, the EFSA restored the prior ADI levels.<ref name=EFSA2014>EFSA Panel on Food Additives and Nutrient Sources added to food (ANS) EFSA Journal 2014;12(7):3765 . doi:10.2903/j.efsa.2014.3765</ref> In 2015, the EFSA found that the exposure estimates did not exceed the ADI of 7&nbsp;mg/kg per day in any population.<ref name=EFSAreaAC>{{cite web|url=http://www.efsa.europa.eu/en/efsajournal/pub/4007 |title=Refined exposure assessment for Allura Red AC (E 129) &#124; European Food |date=13 February 2015 |publisher=Efsa.europa.eu |access-date=2018-09-08}}</ref>

The US FDA did not make changes following the publication of the Southampton study. Following a citizen petition filed by the ] 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.<ref name=FDAdyecomm />

Allura Red AC has previously been banned in ], ], ], ], and ].<ref>{{Cite journal |last1=Esmaeili |first1=Sajjad |last2=Ashrafi-Kooshk |first2=Mohammad Reza |last3=Khaledian |first3=Koestan |last4=Adibi |first4=Hadi |last5=Rouhani |first5=Shohre |last6=Khodarahmi |first6=Reza |date=2016-12-15 |title=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 |url=https://www.sciencedirect.com/science/article/pii/S0308814616309712 |journal=Food Chemistry |volume=213 |pages=494–504 |doi=10.1016/j.foodchem.2016.06.078 |pmid=27451209 |issn=0308-8146}}</ref> This changed in 2008, when the EU adopted a common framework for authorizing food additives,<ref>{{cite web|url=https://www.efsa.europa.eu/en/topics/topic/food-additives#eu-framework|title= Food additives - EU Framework|access-date=2024-03-06|archive-url=https://web.archive.org/web/20240206203429/https://www.efsa.europa.eu/en/topics/topic/food-additives|archive-date=2024-02-06}}</ref> under which Allura Red AC is not currently banned.<ref name=EFSAreaAC /> In ] and ], it was banned between 1978 and 2001, a period in which azo dyes were only legally used in alcoholic beverages and some fish products.<ref>{{cite web|url=http://www.mattilsynet.no/mat/mattrygghet/tilsetningsstoffer/norway_and_food_additives_34434|title=Norwegian Food Safety Authority|access-date=2007-07-09|archive-url=https://archive.today/20120804205754/http://www.mattilsynet.no/mat/mattrygghet/tilsetningsstoffer/norway_and_food_additives_34434|archive-date=2012-08-04|url-status=dead}}</ref>

==References==
{{Reflist|30em}}

==External links==
* on PubChem
*
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{{Food colorings}}

{{DEFAULTSORT:Allura Red Ac}}
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