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Revision as of 16:11, 29 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 06:12, 18 December 2024 edit undoApril Arcus (talk | contribs)Extended confirmed users1,613 edits →Uses 
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{{Redirect|E122|the chemical element|unbibium}}

{{Use dmy dates|date=June 2020}}
{{chembox {{chembox
| Verifiedfields = changed
|ImageFile=Azorubine.svg
| Watchedfields = changed
|IUPACName=disodium 4-hydroxy-2-naphthalene-1-sulfonate
| verifiedrevid = 458267480
|OtherNames=''carmoisine'',<br />''Food Red 3'',<br />''Azorubin S'',<br />''Brillantcarmoisin O'',<br />''Acid Red 14'', or<br />''C.I. 14720''
| ImageFile=Azorubine.svg
|Section1= {{Chembox Identifiers
| ImageFile1=Carmoisine ball-and-stick.png
| ChemSpiderID = 11588223
| IUPACName=disodium 4-hydroxy-2-naphthalene-1-sulfonate
| 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
| OtherNames={{Unbulleted list|carmoisine|Food Red 3|Azorubin S|Brillantcarmoisin O|Acid Red 14|C.I. 14720}}
| InChIKey = YSVBPNGJESBVRM-NUQVWONBAX
|Section1={{Chembox Identifiers
| InChI1 = 1/C20H14N2O7S2.2Na/c23-18-11-17(20(31(27,28)29)15-8-4-2-6-13(15)18)22-21-16-9-10-19(30(24,25)26)14-7-3-1-5-12(14)16;;/h1-11,23H,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2/b22-21+;;

| InChIKey1 = YFRYFMYYBODLLA-DGPRXMBVBB
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| SMILES1 = ..S(=O)(=O)c4ccc(/N=N/c1cc(O)c2ccccc2c1S()(=O)=O)c3ccccc34
| ChemSpiderID = 11588225
| StdInChI = 1S/C20H14N2O7S2.2Na/c23-18-11-17(20(31(27,28)29)15-8-4-2-6-13(15)18)22-21-16-9-10-19(30(24,25)26)14-7-3-1-5-12(14)16;;/h1-11,23H,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2/b22-21+;;
| SMILES = c1ccc2c(c1)c(ccc2S(=O)(=O))/N=N/c3cc(c4ccccc4c3O)S(=O)(=O)..
| StdInChIKey = YFRYFMYYBODLLA-ZPZFBZIMSA-L
| 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 | CASNo=3567-69-9
| EINECS=217-699-5 | EINECS=217-699-5
| PubChem=6321394 | PubChem=19118
| KEGG_Ref = {{keggcite|changed|kegg}}
| SMILES = ..S(=O)(=O)c4ccc(N=Nc2cc(c1ccccc1c2O)S()(=O)=O)c3ccccc34
| 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 |Section2={{Chembox Properties
| Formula= | Formula=
| C=20 | H=12 | N=2 | Na=2 | O=7 | S=2
| MolarMass=
| MolarMass=502.44
| Appearance=
| Appearance=red powder
| Density=
| MeltingPt= | Density=
| MeltingPt=>{{convert|300|C}}
| BoilingPt=
| Solubility= | BoilingPt=
| Solubility=Soluble (120g/L)
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Azorubine''' is an ] consisting of two ] subunits.<ref name=Ullmann>{{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}}</ref> It is a red solid. It is mainly used in foods that are heat-treated after fermentation. It has ] E122.<ref></ref>
'''Azorubine''', '''carmoisine''', '''Food Red 3''', '''Azorubin S''', '''Brillantcarmoisin O''', '''Acid Red 14''', or '''C.I. 14720''' is a synthetic red ] from the ] group. It usually comes as a disodium salt. It is a red to maroon powder. It is used for the purposes where the food is heat-treated after fermentation. It has ] E122. Some of the foods it can be present in are ], ], ], ]s, ]s, ]s, ], ]s, and ] mixes. It is also present in ] Mouthwash.


==Uses==
==Possible health effects==
In the US, this color was listed in 1939 as '''Ext. D&C Red No. 10<ref></ref>''' 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.<ref name=FDAdyecomm>FDA. </ref><ref name="FDA">FDA. 9 November 2008. p37</ref>
It appears to cause ] or intolerance reactions, particularly amongst those with an ] intolerance. Other reactions can include a rash similar to ] and skin ]. ]tics sometimes react badly to it.


In the EU, azorubine is known as ] '''E122''', and is authorized for use in certain foods and beverages, such as cheeses, dried fruit, and some alcoholic beverages,<ref> {{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</ref> and is permitted for use as an ] in medications.<ref>EU. 19 June 2007 </ref>{{rp|4}}<ref></ref>{{rp|16}}
It is one of the colourants that the ] recommends be eliminated from the diet of children.


There are no provisions for azorubine in the ].<ref> Accessed 6 December 2014</ref>
Azo dyes generally have been known to be carcinogenic for over 60 years <ref>{{cite journal |author=McLean P, Reid E, Gurney MW |title=Effect of azo-dye carcinogenesis on enzymes concerned with urea synthesis in rat liver |journal=Biochem. J. |volume=91 |issue=3 |pages=464–73 |year=1964 |month=June |pmid=4284639 |pmc=1202978 }}</ref> and are linked, particularly, to bladder cancer.


==Safety==
On 6 September 2007, the British ] revised advice on certain artificial food additives, including E122.
Azorubine has shown no evidence of mutagenic or carcinogenic properties and an ] (ADI) of 0–4&nbsp;mg/kg was established in 1983 by the WHO.<ref>WHO, 1983. . Linked from </ref>{{rp|19}} In rare instances, it may cause skin and respiratory allergic reactions even to FDA approved dosages.


No evidence supports broad claims that food coloring causes ] and ]-like behavior in children.<ref>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}}</ref>{{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.<ref name=FDAdyecomm/><ref name=Peds2012>{{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 }}</ref>
Professor Jim Stevenson from Southampton University, and author of the report, said: "This has been a major study investigating an important area of research. The results suggest that consumption of certain mixtures of artificial food colours and sodium benzoate preservative are associated with increases in hyperactive behaviour in children.

"However, parents should not think that simply taking these additives out of food will prevent hyperactive disorders. We know that many other influences are at work but this at least is one a child can avoid."

The following additives were tested in the research:

* Sunset yellow (]) (FD&C Yellow #6) - Colouring found in squashes
* Carmoisine (E122) - Red colouring in jellies
* Tartrazine (]) (FD&C Yellow #5) - Yellow colouring
* Ponceau 4R (]) - Red colouring
* Sodium benzoate (]) - Preservative
* Quinoline yellow (]) - Food colouring
* Allura red AC (]) (FD&C Red #40) - Orange / red food dye<ref></ref>

On 10 April 2008, the Foods Standard Agency called for a voluntary removal of the colours (but not sodium benzoate) by 2009.<ref>BBC 10 April 2008</ref> In addition, it recommended that there should be action to phase them out in food and drink in the European Union (EU) over a specified period.<ref>FSA 10 April 2008</ref>

The EFSA (European Food Standards Agency) has reviewed the Southampton Study and determined that the results are inconclusive and warrant no action at this time in the EU pending the outcome of further testing.{{Citation needed|date=April 2008}}

UK ministers have agreed that the six colourings will be phased out by 2009.<ref>BBC 12 November 2008</ref>

Azorubine is commonly used in the ] and in several other countries in a popular brand of soda and in children's medicine ],<ref name=Calpol>{{cite news|url=http://www.theecologist.org/green_green_living/behind_the_label/346400/behind_the_label_calpol.html|title=Behind the Label: Calpol|author=Pat Thomas|date=29th October|publisher=The Ecologist}}</ref> but it is a prohibited food additive in ], ], ], ] and the ].<ref>{{cite news| url=http://www.cbc.ca/news/background/foodsafety/additives.html | work=CBC News | title=Food additives | date=29 September 2008}}</ref>


==References== ==References==
{{reflist}}
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