Azorubine: Difference between revisions

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			{{Redirect\|E122\|the chemical element\|unbibium}}

			{{Use dmy dates\|date=June 2020}}
	{{chembox		{{chembox
	\| Verifiedfields = changed		\| Verifiedfields = changed
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~399535906~~		\| verifiedrevid = 458267480
	\|ImageFile=Azorubine.svg		\| ImageFile=Azorubine.svg
			\| ImageFile1=Carmoisine ball-and-stick.png
	\|IUPACName=disodium 4-hydroxy-2-naphthalene-1-sulfonate
			\| IUPACName=disodium 4-hydroxy-2-naphthalene-1-sulfonate
	\|OtherNames=''carmoisine'',<br />''Food Red 3'',<br />''Azorubin S'',<br />''Brillantcarmoisin O'',<br />''Acid Red 14'', or<br />''C.I. 14720''
			\| OtherNames={{Unbulleted list\|carmoisine\|Food Red 3\|Azorubin S\|Brillantcarmoisin O\|Acid Red 14\|C.I. 14720}}
	\|Section1= {{Chembox Identifiers
			\|Section1={{Chembox Identifiers
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}

	\| ChemSpiderID = 11588223
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| 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
			\| ChemSpiderID = 11588225
	\| InChIKey = YSVBPNGJESBVRM-NUQVWONBAX
			\| SMILES = c1ccc2c(c1)c(ccc2S(=O)(=O))/N=N/c3cc(c4ccccc4c3O)S(=O)(=O)..
	\| 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+;;
			\| 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+;;
	\| InChIKey1 = YFRYFMYYBODLLA-DGPRXMBVBB
			\| InChIKey = YSVBPNGJESBVRM-DGPRXMBVBS
	\| SMILES1 = ..S(=O)(=O)c4ccc(/N=N/c1cc(O)c2ccccc2c1S()(=O)=O)c3ccccc34
	\| StdInChI_Ref = {{stdinchicite\|~~correct~~\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
	\| 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+;;		\| 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\|~~correct~~\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChIKey = ~~YFRYFMYYBODLLA~~-ZPZFBZIMSA-L		\| StdInChIKey = YSVBPNGJESBVRM-ZPZFBZIMSA-L

	\| CASNo_Ref = {{cascite\|correct\|??}}
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = <!-- blanked - oldvalue: 3567-69-9 -->
	\| ~~EINECS~~=~~217~~-~~699~~-5		\| CASNo=3567-69-9
			\| EINECS=217-699-5
	\| PubChem=6321394
			\| PubChem=19118
	\| KEGG_Ref = {{keggcite\|changed\|kegg}}		\| KEGG_Ref = {{keggcite\|changed\|kegg}}
	\| KEGG = ~~<!-- blanked - oldvalue:~~ C19358 ~~-->~~		\| KEGG = C19358
	\| ~~UNII_Ref~~ = {{~~fdacite~~\|changed\|~~FDA~~}}		\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 1552837
			\| ChEMBL2_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL2 = 1624506
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = DR4641L47F		\| UNII = DR4641L47F
	\| SMILES = ..S(=O)(=O)c4ccc(N=Nc2cc(c1ccccc1c2O)S()(=O)=O)c3ccccc34
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula=~~C20H12N2Na2O7S2~~		\| Formula=
			\| C=20 \| H=12 \| N=2 \| Na=2 \| O=7 \| S=2
	\| MolarMass=502.44
			\| MolarMass=502.44
	\| Appearance=red powder
			\| Appearance=red powder
	\| Density=
			\| Density=
	\| MeltingPt=>300 C
			\| MeltingPt=>{{convert\|300\|C}}
	\| BoilingPt=
			\| BoilingPt=
	\| Solubility=Soluble (120g/l)
			\| 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.

	==~~Other names~~==		==Uses==
			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>
	'''Chemical names''': 2-(4-Sulfo-1-naphthylazo)-1-naphthol-4-sulfonic acid disodium; 4-Hydroxy-3-((4-sulpho-1-naphthalenyl)azo)-1-naphthalenesulphonic acid disodium; Disodium 4-hydroxy-3-((4-sulphonatonaphthyl)azo)naphthalenesulphonate

			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}}
	'''Color index''': EEC No.: E122, C.I. 14720, C.I. Acid Red 14, C.I. Acid Red 14 disodium salt, C.I. Food Red 3

			There are no provisions for azorubine in the ].<ref> Accessed 6 December 2014</ref>
	'''Other names''': Azorubine; Brillantcarmoisin O, Schultz Nr. 208; Solar Rubine; Solochrome Blue FB; Standacol carmoisine; Tertracid Red CA; Tertrochrome Blue FB; omega Chrome Blue FB; Nylomine Acid Red P4B; Omega Chrome Blue FB; Poloxal Red 2B; Java Rubine N; Karmesin; Kenachrome Blue 2R; Kiton Crimson 2R; Kiton Rubine R; Cerven kysela 14; Cerven potravinarska 3; Chrome Fast Blue 2R; Chromotrope FB; Cilefa Rubine R; Crimson 2EMBL; Diadem Chrome Blue G; Atul Acid Crystal Red; Acid Brilliant Rubine 2G<ref>http://chemicalland21.com/lifescience/foco/CARMOISINE.htm</ref>

			==Safety==
	==Possible health effects==
			Azorubine has shown no evidence of mutagenic or carcinogenic properties and an ] (ADI) of 0–4 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.
	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.

			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>
	It is one of the colourants that the ] recommends be eliminated from the diet of children.

	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.

	On 6 September 2007, the British ] revised advice on certain artificial food additives, including E122.

	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.<ref>EFSA 24 November 2009</ref>

	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}}
	<references/>

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Latest revision as of 06:12, 18 December 2024

"E122" redirects here. For the chemical element, see unbibium.

Azorubine
Names


IUPAC name disodium 4-hydroxy-2-naphthalene-1-sulfonate
Other names carmoisine Food Red 3 Azorubin S Brillantcarmoisin O Acid Red 14 C.I. 14720
Identifiers
CAS Number	3567-69-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1552837 ChEMBL1624506
ChemSpider	11588225
ECHA InfoCard	100.020.598
EC Number	217-699-5
E number	E122 (colours)
KEGG	C19358
PubChem CID	19118
UNII	DR4641L47F
CompTox Dashboard (EPA)	DTXSID3021225
InChI InChI=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+;;Key: YSVBPNGJESBVRM-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+;;Key: YSVBPNGJESBVRM-DGPRXMBVBS
SMILES c1ccc2c(c1)c(ccc2S(=O)(=O))/N=N/c3cc(c4ccccc4c3O)S(=O)(=O)..
Properties
Chemical formula	C₂₀H₁₂N₂Na₂O₇S₂
Molar mass	502.44
Appearance	red powder
Melting point	>300 °C (572 °F)
Solubility in water	Soluble (120g/L)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

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.

Uses

In the US, this color was listed in 1939 as 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.

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, and is permitted for use as an excipient in medications.

There are no provisions for azorubine in the Codex Alimentarius.

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. 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 food intolerance and ADHD-like behavior in children. It is possible that certain food coloring may act as a trigger in those who are genetically predisposed, but the evidence is weak.

References

Klaus Hunger; Peter Mischke; Wolfgang Rieper; et al. (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.
Pubchem entry
Regulatory Status of Color Additives: Ext. D&C Red No. 10
^ FDA. 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. Food and Drug Administration, Compliance Program Guidance Manual, Chapter 03 - Foodborne Biological Hazards p37
Azorubine entry in EU Food Additive Database Archived 11 December 2014 at the Wayback Machine Accessed 6 December 2014
EU. 19 June 2007 Guideline on Excipients in the Dossier for Application for Marketing Authorisation of a Medicinal Product
Directive 94/36/EC - European Commission
Azorubine (Carmoisine) (122) in the GSFA Online Database Accessed 6 December 2014
WHO, 1983. Evaluation of certain food additives and contaminants. Linked from WHO listing here
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
Millichap JG; Yee MM (February 2012). "The diet factor in attention-deficit/hyperactivity disorder". Pediatrics. 129 (2): 330–337. doi:10.1542/peds.2011-2199. PMID 22232312. S2CID 14925322.

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