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			{{Short description|Chemical compound}}
	{{Otheruses|Amaranth (disambiguation)}}		{{Other uses|Amaranth (disambiguation)}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 401797408		| verifiedrevid = 443304690
	|ImageFile=Amaranth new.png		| ImageFile = Amaranth new.png
	|ImageSize=200px		| ImageSize =
⚫	|IUPACName=trisodium (4''E'')-3-oxo-4-naphthalene-<br>2,7-disulfonate
			| ImageFile1 = Amaranth (dye) ball-and-stick.png
⚫	|OtherNames=FD&C Red No. 2,<br>E123,<br>C.I. Food Red 9,<br>Acid Red 27,<br>Azorubin S,<br>C.I. 16185
			| ImageSize1 =
⚫	|Section1= {{Chembox Identifiers
		⚫	| Name = Amaranth
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| IUPACName = Trisodium (4''E'')-3-oxo-4-naphthalene-2,7-disulfonate
		⚫	| OtherNames = {{Unbulleted list|FD&C Red No. 2|E123|C.I. Food Red 9|Acid Red 27|Azorubin S|C.I. 16185}}
		⚫	|Section1={{Chembox Identifiers
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 21169821		| ChemSpiderID = 21169821
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 37RBV3X49K		| UNII = 37RBV3X49K
			| EC_number = 213-022-2
			| DTXSID = DTXSID2021232
			| ChEBI = 34533
			| ChEMBL = 2104005
			| KEGG = C14760
	| InChI = 1/C20H14N2O10S3.3Na/c23-20-18(35(30,31)32)10-11-9-12(33(24,25)26)5-6-13(11)19(20)22-21-16-7-8-17(34(27,28)29)15-4-2-1-3-14(15)16;;;/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32);;;/q;3*+1/p-3		| InChI = 1/C20H14N2O10S3.3Na/c23-20-18(35(30,31)32)10-11-9-12(33(24,25)26)5-6-13(11)19(20)22-21-16-7-8-17(34(27,28)29)15-4-2-1-3-14(15)16;;;/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32);;;/q;3*+1/p-3
	| InChIKey = WLDHEUZGFKACJH-DFZHHIFOAW		| InChIKey = WLDHEUZGFKACJH-DFZHHIFOAW
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	| StdInChIKey = WLDHEUZGFKACJH-UHFFFAOYSA-K		| StdInChIKey = WLDHEUZGFKACJH-UHFFFAOYSA-K
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=915-67-3		| CASNo =915-67-3
	| PubChem=6093196		| PubChem =13506
	| SMILES = ...S(=O)(=O)c4ccc(N=Nc1c2ccc(cc2cc(c1O)S()(=O)=O)S()(=O)=O)c3ccccc34		| SMILES = ...S(=O)(=O)c4ccc(N=Nc1c2ccc(cc2cc(c1O)S()(=O)=O)S()(=O)=O)c3ccccc34
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>20</sub>H<sub>11</sub>N<sub>2</sub>Na<sub>3</sub>O<sub>10</sub>S<sub>3</sub>		| Formula =C<sub>20</sub>H<sub>11</sub>N<sub>2</sub>Na<sub>3</sub>O<sub>10</sub>S<sub>3</sub>
	| MolarMass=604.47305		| MolarMass =604.47305
	| Appearance=Dark red solid		| Appearance =Dark red solid
	| Density=		| Density =
			| MeltingPtC = 120
	| MeltingPt=120 °C (decomposes)
			| MeltingPt_notes = (decomposes)
	| BoilingPt=
			| BoilingPt =
	| Solubility=
			| Solubility =
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=
			| MainHazards =
	| FlashPt=
			| FlashPt =
	| Autoignition=
			| AutoignitionPt =
	| RPhrases = {{R36/37/38}}
	| SPhrases = {{S36/37/39}}		| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
⚫	}}
			| HPhrases = {{H-phrases|315|319|335}}
			| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
		⚫	}}
	}}		}}
			'''Amaranth''', '''FD&C Red No. 2''', '''E123''', '''C.I. Food Red 9''', '''Acid Red 27''', '''Azorubin S''', or '''C.I. 16185''' is a modified ] ] used as a ] and to color ]. The name was taken from ], a plant distinguished by its red color and edible protein-rich seeds.
	'''Amaranth''', '''FD&C Red No. 2''', '''E123''', '''C.I. Food Red 9''', '''Acid Red 27''', '''Azorubin S''', or '''C.I. 16185''', is a dark red to purple ] once used as a ] and to color ], but since 1976 it has been banned in the United States by the ] (FDA) as it is a suspected ].<ref>"The following color additives are not authorized for use in food products in the United States: (1) Amaranth (C.I. 16185, EEC No. E123, formerly certifiable as FD&C red No. 2);" </ref> It usually comes as a trisodium ]. It has the appearance of reddish-brown, dark red to purple water-soluble powder that decomposes at 120 °C without melting. Its water solution has absorption maximum at about 520&nbsp;nm.<ref></ref> Amaranth is an anionic dye. It can be applied to natural and synthetic ]s, ], ], and ]s. As a ] it has ] E123. Like all azo dyes, Amaranth was, during the middle of the 20th century, made from ]; modern synthetics are more likely to be made from petroleum byproducts.<ref></ref><ref></ref> Amaranth's use is still legal in some countries, notably in the ] where it is most commonly used to give ] their distinctive colour. Its name was taken from ], a plant distinguished by its red color and edible protein-rich seeds.
			Amaranth is an anionic dye. It can be applied to natural and synthetic ]s, ], ], and ]s. As a ] it has ] E123. Amaranth usually comes as a trisodium ]. It has the appearance of reddish-brown, dark red to purple water-soluble powder that decomposes at 120&nbsp;°C without melting. Its water solution has an absorption maximum of about 520&nbsp;nm. Like all azo dyes, Amaranth was, during the middle of the 20th century, made from ]; modern synthetics are more likely to be made from petroleum byproducts.<ref>{{cite web | url = http://www.lookcut.com/tools/food-additives/amaranth-e123.html | title = Amaranth E123 | publisher = LOOKCUT, INC. | date = 2004–2010 | accessdate = August 15, 2014}}</ref><ref>{{cite web | url = http://www.craftsman-style.info/finishing/014-aniline.htm | work = Craftsman Style | title = Aniline Wood Dye, Coal Tar Dyes | date = 2005–2012 | publisher = International Styles Network | accessdate = August 15, 2014}}</ref>
	==History==
⚫	After an incident in 1954 involving ],<ref></ref><ref name=Toxicology/> the FDA retested food colors. In 1960 the FDA was given jurisdiction over color additives, limiting the amounts that could be added to foods and requiring producers of food color to ensure safety and proper labeling of colors. Permission to use food additives was given on a provisional basis, which could be withdrawn should safety issues arise.<ref name=Toxicology/> The FDA gave "]" (GRAS) provisional status to substances already in use, and extended Red No. 2's provisional status 14 times.
			Since 1976, amaranth dye has been banned in the United States by the ] (FDA)<ref>{{citation | quote = Be aware that the following color additives are not on the list for use in food products in the United States. a. Amaranth (C.I. 16185, EEC No E123, formerly certifiable as FD&C Red No 2) | url = https://www.fda.gov/downloads/Food/GuidanceComplianceRegulatoryInformation/ComplianceEnforcement/ucm072848.pdf | title = Compliance Program Guidance Manual: Domestic Food Safety (FY07-08) | page = 6 | publisher = ] | date = November 9, 2008}}</ref> as a suspected ].<ref>{{citation | title = Color Additives Fact Sheet | publisher = ]'s Center for Food Safety and Applied Nutrition | date = July 30, 2001 | url = http://www.cfsan.fda.gov/~dms/cos-221.html | archive-url = https://web.archive.org/web/20011117164702/http://www.cfsan.fda.gov/~dms/cos-221.html | archive-date = November 17, 2001}}</ref><ref>{{citation | title = Overview of Food Color Additives, Prepared for the USDA National Organic Program and the National Organic Standards Board | date = October 14, 2005 | pages = 1 and 7 | publisher = ] (]) | url = http://www.ams.usda.gov/AMSv1.0/getfile?dDocName=STELPRDC5057347 | accessdate = August 15, 2014 | archive-date = March 9, 2010 | archive-url = https://web.archive.org/web/20100309133752/http://www.ams.usda.gov/AMSv1.0/getfile?dDocName=STELPRDC5057347 | url-status = dead }}</ref> Its use is still legal in some countries, notably in the ] where it is most commonly used to give ] their distinctive color.
⚫	In 1971 a Russian study linked cancer to the dye.<ref name=Toxicology>{{cite book |url= http://books.google.com/books?id=zqLLa-MI8k0C&printsec=frontcover&dq=Toxicology+Omaye&hl=en&ei=bdsaTMehNtONnQf1ye20Cw&sa=X&oi=book_result&ct=result&resnum=1&ved=0CC8Q6AEwAA#v=onepage&q=Amaranth&f=false | title= Food and nutritional toxicology |author= Stanley T. Omaye}}</ref> By 1976 over 1 million pounds of the dye worth $5 million was used as a colorant in $10 billion worth of foods, drugs and cosmetics.<ref name=time/> ] in the ], perturbed by what they perceived as collusion between the FDA and food conglomerates,<ref name=NewSci/> put pressure on the FDA to ban it.<ref name=time/> FDA Commissioner ] defended the dye, as he had earlier defended the FDA against collusion accusations in his 1975 book,<ref name=NewSci>{{cite book |url= http://books.google.com/books?id=0C1mPFyQYloC&pg=PA600&dq=Alexander+Schmidt+FDA+no+evidence&hl=en&ei=neUaTOf9GdnsnQfFvpC1Cw&sa=X&oi=book_result&ct=result&resnum=1&ved=0CCgQ6AEwAA#v=onepage&q=Alexander%20Schmidt%20FDA%20no%20evidence&f=false |title= FDA in difficulties |work=Washington View |publisher=New Scientist |date= Dec 1975}}</ref> stating that the FDA found "no evidence of a public health hazard".<ref name=time/> Testing by the FDA found no undeniable proof of a health hazard, but did find a statistically significant increase in the incidence of malignant tumors in female rats given a high doage of the dye,<ref name=Toxicology/> and concluded that since there could also no longer be a presumption of safety, that use of the dye should be discontinued.<ref name=Toxicology/> The FDA banned FD&C Red No. 2 in 1976.<ref name=time>{{cite news |first= |last= |authorlink= |coauthors= |title=Death of a Dye |url=http://www.time.com/time/magazine/article/0,9171,945520,00.html |work=] |date=February 2, 1976 |accessdate=2009-07-07 }}</ref><ref>{{cite news |first= |last= |authorlink= |coauthors= |title=Burger Backs Red Dye Ban Pending Rule |url= http://pqasb.pqarchiver.com/courant/access/959307712.html?dids=959307712:959307712&FMT=ABS&FMTS=ABS:AI&date=Feb+14%2C+1976&author=&pub=The+Hartford+Courant&desc=Burger+Backs+Red+Dye+Ban+Pending+Rule&pqatl=google |work=] |date=February 14, 1976 |accessdate=2009-07-07 }}</ref> ] (Allura Red AC) replaced the banned Red No. 2.
			==History and health effects==
⚫	==References==
		⚫	After an incident in the 1950s involving ]<ref>{{cite book | url = https://books.google.com/books?id=ob4PAAAAIAAJ&q=FD%26C+Orange+number+1+Halloween+candy | title = Science News Letter, Volumes 65-66 | publisher = Science Service | date = January 30, 1954 | page = 95}}</ref><ref name=Toxicology/> in Clover brand "Spooky Lozenges" and other orange and red candies manufactured at that time, the FDA retested food colors. Later, in 1960, the FDA was given jurisdiction over color additives, limiting the amounts that could be added to foods and requiring producers of food color to ensure the safety and proper labeling of colors. Permission to use food additives was given on a provisional basis, which could be withdrawn should safety issues arise.<ref name=Toxicology/> The FDA gave "]" (GRAS) provisional status to substances already in use, and extended Red No. 2's provisional status 14 times.
⚫	{{reflist|2}}
		⚫	In 1971, a Soviet study linked the dye to cancer.<ref>{{cite web |url=https://priceonomics.com/why-red-mandms-disappeared-for-a-decade/ |title=Why Red M&M's Disappeared for a Decade |date=12 May 2014 |accessdate=2016-08-16 |publisher=Pricenomics }}</ref><ref name=Toxicology>{{cite book |url= https://books.google.com/books?id=zqLLa-MI8k0C&q=Amaranth | title= Food and Nutritional Toxicology | first = Stanley T. | last = Omaye | page = 257 | publisher = CRC Press LLC | year = 2004 | isbn = 0-203-48530-0}}</ref><!-- need Soviet study citation --> By 1976, over {{convert|1000000|lb}} of the dye worth $5 million was used as a colorant in $10 billion worth of foods, drugs and cosmetics.<ref name=time/> ] in the United States, perturbed by what they perceived as collusion between the FDA and food conglomerates,<ref name=NewSci>{{cite journal |url= https://books.google.com/books?id=0C1mPFyQYloC&q=Alexander%20Schmidt%20FDA%20no%20evidence&pg=PA600 |title= Washington View: FDA in difficulties | journal=New Scientist | volume = 64 | issue = 978 | date= 4 December 1975 | first = Dan | last = Greenberg | page = 600 | publisher = New Science Publications | location = London}}</ref> put pressure on the FDA to ban it.<ref name=time/> FDA Commissioner ] defended the agency's stance, as he had earlier defended the FDA against collusion accusations in his 1975 book, stating that the FDA found "no evidence of a public health hazard".{{verificationneeded|date=May 2016}}<!--Please verify that the source says "Schmidt defended the dye despite all the evidence, as he had earlier defended the FDA against collusion accusations in his 1975 book"--><ref name=time/> However testing by the FDA found a statistically significant increase in the incidence of malignant tumors in female ]s given a high dosage of the dye,<ref name=Toxicology/> and concluded that since there could also no longer be a presumption of safety, that use of the dye should be discontinued.<ref name=Toxicology/> The FDA banned FD&C Red No. 2 in 1976.<ref name=time>{{cite magazine |title=Death of a Dye |url=http://www.time.com/time/magazine/article/0,9171,945520,00.html |archive-url=https://web.archive.org/web/20050111223907/http://www.time.com/time/magazine/article/0,9171,945520,00.html |url-status=dead |archive-date=January 11, 2005 |magazine=] |date=February 2, 1976 |accessdate=2009-07-07 }}</ref><ref>{{cite news |title=Burger Backs Red Dye Ban Pending Rule |url=https://pqasb.pqarchiver.com/courant/access/959307712.html?dids=959307712:959307712&FMT=ABS&FMTS=ABS:AI&date=Feb+14%2C+1976&author=&pub=The+Hartford+Courant&desc=Burger+Backs+Red+Dye+Ban+Pending+Rule&pqatl=google |work=] |date=February 14, 1976 |accessdate=2009-07-07 |archive-date=2012-10-21 |archive-url=https://web.archive.org/web/20121021133151/http://pqasb.pqarchiver.com/courant/access/959307712.html?dids=959307712:959307712&FMT=ABS&FMTS=ABS:AI&date=Feb+14,+1976&author=&pub=The+Hartford+Courant&desc=Burger+Backs+Red+Dye+Ban+Pending+Rule&pqatl=google |url-status=dead }}</ref> ] (Allura Red AC) replaced the banned Red No. 2, as its toxicity was determined to be significantly less than Red No. 2 due to the removal of one sodium sulfonate functional group, among other molecular adjustments to furthermore reduce the immediate toxicity of the specific azo dye upon consumption.
	==See also==		==See also==
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		⚫	==References==
		⚫	{{reflist|30em}}
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