azorubine
{{Redirect|E122|the chemical element|unbibium}}
{{Use dmy dates|date=June 2020}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458267480
| ImageFile=Azorubine.svg
| ImageFile1=Carmoisine ball-and-stick.png
| IUPACName=disodium 4-hydroxy-3-[(E)-(4-sulfonato-1-naphthyl)diazenyl]naphthalene-1-sulfonate
| OtherNames={{Unbulleted list|carmoisine|Food Red 3|Azorubin S|Brillantcarmoisin O|Acid Red 14|C.I. 14720}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 11588225
| SMILES = c1ccc2c(c1)c(ccc2S(=O)(=O)[O-])/N=N/c3cc(c4ccccc4c3O)S(=O)(=O)[O-].[Na+].[Na+]
| InChI = 1/C20H14N2O7S2.2Na/c23-20-15-8-4-3-7-14(15)19(31(27,28)29)11-17(20)22-21-16-9-10-18(30(24,25)26)13-6-2-1-5-12(13)16;;/h1-11,23H,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2/b22-21+;;
| InChIKey = YSVBPNGJESBVRM-DGPRXMBVBS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C20H14N2O7S2.2Na/c23-20-15-8-4-3-7-14(15)19(31(27,28)29)11-17(20)22-21-16-9-10-18(30(24,25)26)13-6-2-1-5-12(13)16;;/h1-11,23H,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2/b22-21+;;
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YSVBPNGJESBVRM-ZPZFBZIMSA-L
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=3567-69-9
| EINECS=217-699-5
| PubChem=19118
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19358
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1552837
| ChEMBL2_Ref = {{ebicite|changed|EBI}}
| ChEMBL2 = 1624506
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DR4641L47F
}}
|Section2={{Chembox Properties
| Formula=
| C=20 | H=12 | N=2 | Na=2 | O=7 | S=2
| MolarMass=502.44
| Appearance=red powder
| Density=
| MeltingPt=>{{convert|300|C}}
| BoilingPt=
| Solubility=Soluble (120g/L)
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
Azorubine, also known as carmoisine, is an azo dye consisting of two naphthalene subunits.{{Ullmann|author1=Klaus Hunger|author2=Peter Mischke|author3=Wolfgang Rieper|author4=Roderich Raue|author5=Klaus Kunde|author6=Aloys Engel|display-authors=3|title=Azo Dyes|year=2005|doi=10.1002/14356007.a03_245}} It is a red solid. It is mainly used in foods that are heat-treated after fermentation. It has E number E122.[https://pubchem.ncbi.nlm.nih.gov/compound/19118?from=summary Pubchem entry]
Uses
In the US, this color was listed in 1939 as Ext. D&C Red No. 10[https://hfpappexternal.fda.gov/scripts/fdcc/index.cfm?set=ColorAdditives&id=ExtDCRed10 Regulatory Status of Color Additives: Ext. D&C Red No. 10] for use in externally applied drugs and cosmetics. It was delisted in 1963 because no party was interested in supporting the studies needed to establish safety. It was not used in food in the US.FDA. [https://web.archive.org/web/20110331210358/http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/FoodAdvisoryCommittee/UCM248549.pdf Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children: March 30-31, 2011]FDA. 9 November 2008. [https://www.fda.gov/downloads/Food/GuidanceComplianceRegulatoryInformation/ComplianceEnforcement/ucm072848.pdf Food and Drug Administration, Compliance Program Guidance Manual, Chapter 03 - Foodborne Biological Hazards]{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}} p37
In the EU, azorubine is known as E number E122, and is authorized for use in certain foods and beverages, such as cheeses, dried fruit, and some alcoholic beverages,[https://webgate.ec.europa.eu/sanco_foods/main/index.cfm?event=substance.view&identifier=11 Azorubine entry in EU Food Additive Database] {{Webarchive|url=https://web.archive.org/web/20141211094754/https://webgate.ec.europa.eu/sanco_foods/main/index.cfm?event=substance.view&identifier=11 |date=11 December 2014 }} Accessed 6 December 2014 and is permitted for use as an excipient in medications.EU. 19 June 2007 [http://www.ema.europa.eu/docs/en_GB/document_library/Scientific_guideline/2009/09/WC500003382.pdf Guideline on Excipients in the Dossier for Application for Marketing Authorisation of a Medicinal Product]{{rp|4}}[http://ec.europa.eu/food/fs/sfp/addit_flavor/flav08_en.pdf Directive 94/36/EC - European Commission]{{rp|16}}
There are no provisions for azorubine in the Codex Alimentarius.[https://web.archive.org/web/20060610005124/http://www.codexalimentarius.net/gsfaonline/additives/details.html?id=91 Azorubine (Carmoisine) (122) in the GSFA Online Database] Accessed 6 December 2014
Safety
Azorubine has shown no evidence of mutagenic or carcinogenic properties and an acceptable daily intake (ADI) of 0–4 mg/kg was established in 1983 by the WHO.WHO, 1983. [http://whqlibdoc.who.int/trs/WHO_TRS_696.pdf Evaluation of certain food additives and contaminants]. Linked from [http://apps.who.int/food-additives-contaminants-jecfa-database/chemical.aspx?chemINS=122 WHO listing here]{{rp|19}} In rare instances, it may cause skin and respiratory allergic reactions even to FDA approved dosages.[https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6759534/#ref4]
No evidence supports broad claims that food coloring causes food intolerance and ADHD-like behavior in children.Tomaska LD and Brooke-Taylor, S. Food Additives - General pp 449-454 in Encyclopedia of Food Safety, Vol 2: Hazards and Diseases. Eds, Motarjemi Y et al. Academic Press, 2013. {{ISBN|9780123786135}}{{rp|452}} It is possible that certain food coloring may act as a trigger in those who are genetically predisposed, but the evidence is weak.{{cite journal |author1=Millichap JG |author2=Yee MM |title=The diet factor in attention-deficit/hyperactivity disorder|journal=Pediatrics |volume=129 |issue=2 | pages=330–337 |date=February 2012 |pmid=22232312|doi=10.1542/peds.2011-2199 |s2cid=14925322 }}