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Revision as of 22:25, 12 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[...← Previous edit		Latest revision as of 14:28, 11 September 2024 edit undoCitation bot (talk | contribs)Bots5,424,088 edits Add: bibcode, date. | Use this bot. Report bugs. | Suggested by Abductive | Category:E-number additives | #UCB_Category 29/313
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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 446025541
			| Watchedfields = changed
⚫	|Reference=<ref>'']'', 11th Edition, '''1756'''.</ref>
		⚫	| verifiedrevid = 455281518
⚫	|ImageFile=Canthaxanthin.svg
		⚫	| Reference =<ref>'']'', 11th Edition, '''1756'''.</ref>
⚫	|ImageSize=250px
		⚫	| ImageFile =Canthaxanthin.svg
⚫	|IUPACName= β,β-Carotene-4,4'-dione
		⚫	| ImageSize =275
	|OtherNames=Cantaxanthin, Cantaxanthine, Canthaxanthine, Carophyll Red, Roxanthin Red 10, L-Orange 7g, C.I. Food Orange 8, E161g, 2,4,4-Trimethyl-3--1-cyclohex-2-enone
			| ImageAlt = Skeletal formula of canthaxanthin
			| ImageFile1 = Canthaxanthin 3D spacefill.png
			| ImageSize1 =275
			| ImageAlt1 = Space-filling model of the canthaxanthin molecule
		⚫	| IUPACName = β,β-Carotene-4,4′-dione
			| SystematicName = 3,3′-bis(2,4,4-trimethylcyclohex-2-en-1-one)
			| OtherNames = {{Unbulleted list
			| Cantaxanthin
			| Cantaxanthine
		⚫	| Canthaxanthine
			| Lucantin red (BASF)
			| Lucantin Red CWD (BASF)
			| Carophyll Red (DSM)
			| Roxanthin Red 10 (Adisseo)
			| L-Orange 7g
			| C.I. Food Orange 8
		⚫	| E161g
			}}
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4447582		| ChemSpiderID = 4447582
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 4C3C6403MU		| UNII = 4C3C6403MU
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1329004
	| InChI = 1/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+		| InChI = 1/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
	| InChIKey = FDSDTBUPSURDBL-OQWFGLAJBT		| InChIKey = FDSDTBUPSURDBL-OQWFGLAJBT
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	| StdInChIKey = FDSDTBUPSURDBL-OQWFGLAJSA-N		| StdInChIKey = FDSDTBUPSURDBL-OQWFGLAJSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=514-78-3		| CASNo =514-78-3
	| PubChem=5281227		| PubChem =5281227
			| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫	| SMILES = CC(CC1)(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(C(C)(C)CC2)=C(C)C2=O)=C(C)C1=O
			| ChEBI = 3362
		⚫	| SMILES = CC(CC1)(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(C(C)(C)CC2)=C(C)C2=O)=C(C)C1=O
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	|C=40|H=52|O=2		| C=40 | H=52 | O=2
	| MolarMass=564.82 g/mol		| MolarMass =564.82 g/mol
	| Appearance=Violet crystals		| Appearance =Violet crystals
	| Density=		| Density =
			| MeltingPtC = 211 to 212
	| MeltingPt=211-212 °C (decomposition)<ref>{{cite journal|last=Petracek|first=F. J.|coauthors=Zechmeister, L.|title=Reaction of beta-Carotene with N-Bromosuccinimide: The Formation and Conversions of Some Polyene Ketones|journal=J. Am. Chem. Soc.|year=1956|volume=78|issue=7|pages=1427–1434|doi=10.1021/ja01588a044|accessdate=7 July 2011}}</ref>		| MeltingPt_notes = (decomposition)<ref>{{cite journal |last=Petracek |first=F. J. |author2=Zechmeister, L. |title=Reaction of beta-carotene with N-bromosuccinimide: the formation and conversions of some polyene ketones |journal=] |year=1956 |volume=78 |issue=7 |pages=1427–1434 |doi=10.1021/ja01588a044}}</ref>
	| BoilingPt=
			| BoilingPt =
	| Solubility=
			| Solubility =
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards =
	| FlashPt=		| FlashPt =
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
	'''Canthaxanthin''' ({{IPAc-en|audio=canthaxanthin-pronunciation.ogg|ˌ|k|æ|n|θ|ə|ˈ|z|æ|n|θ|ɪ|n}}) is a ] pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as ]s. The chemical formula of canthaxanthin is C<SUB>40</SUB>H<SUB>52</SUB>O<SUB>2</SUB>.<ref name="eulink"></ref> It has ] E161g.		'''Canthaxanthin''' {{IPAc-en|audio=En-canthaxanthin.oga|ˌ|k|æ|n|θ|ə|ˈ|z|æ|n|θ|ɪ|n}} is a ]<ref>Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene. Seyoung Choi and Sangho Koo, J. Org. Chem., 2005, 70 (8), pages 3328–3331, {{doi|10.1021/jo050101l}}</ref> pigment widely distributed in nature. ] belong to a larger class of phytochemicals known as ]s. The chemical formula of canthaxanthin is C<SUB>40</SUB>H<SUB>52</SUB>O<SUB>2</SUB>.<ref name="eulink"></ref> It was first isolated in edible mushrooms. It has also been found in ]e, ], ]s, and ]s in fish such as ], ], ] and ].<ref name="eulink"/>
			Canthaxanthin is associated with ] E161g and is approved for use as a food coloring agent in different countries, including the United States<ref>{{cite web |url=https://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm106626.htm |title=Colour Additive Status List |publisher = ]| access-date=2011-10-27}}</ref> and the EU;<ref>{{cite web | url = http://www.food.gov.uk/policy-advice/additivesbranch/enumberlist | title = Current EU approved additives and their E Numbers | publisher = ] | date = 14 March 2012 | access-date = Dec 19, 2012}}</ref> however, it is not approved for use in Australia and New Zealand.<ref>{{cite web |url=http://www.comlaw.gov.au/Details/F2011C00827 |title=Standard 1.2.4 - Labelling of ingredients |date=8 September 2011 |access-date=2011-10-27 | publisher = Australia New Zealand Food Standards Code }}</ref> It is generally authorized for feed applications in at least the following countries: US,<ref>{{cite web |url=http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=73.75 |title=Code of Federal Regulations Title 21, 1 April 2012 |publisher = ]| access-date=2013-06-21}}</ref> Canada,<ref>{{cite web|url=http://laws-lois.justice.gc.ca/eng/regulations/sor-83-593/FullText.html |title=Feeds Regulations, 1983 (SOR/83-593) |publisher=Justice Laws, Canada |access-date=2013-06-21 |url-status=dead |archive-url=https://web.archive.org/web/20130628030401/http://www.laws-lois.justice.gc.ca/eng/regulations/SOR-83-593/FullText.html |archive-date=2013-06-28 }}</ref> EU.<ref>{{cite web |url= http://ec.europa.eu/food/food/animalnutrition/feedadditives/comm_register_feed_additives_1831-03.pdf |title=European Union Register of Feed Additives, Revision 162 released 7 June 2013 | publisher = European Commission | access-date=2013-06-21}}</ref> In the ], canthaxanthin is allowed by law to be added to ] feed, salmon feed and poultry feed.<ref>{{cite web|last=Food Standards Agency UK|title=Canthaxanthin - your questions answered|url=http://www.food.gov.uk/business-industry/farmingfood/animalfeed/animalfeedlegislation/canthaxanthin_qanda/|access-date=19 December 2012|date=12 April 2010|archive-date=23 March 2013|archive-url=https://web.archive.org/web/20130323071916/http://food.gov.uk/business-industry/farmingfood/animalfeed/animalfeedlegislation/canthaxanthin_qanda/|url-status=dead}}</ref> The ] limit is 80&nbsp;mg/kg of feedstuffs,<ref name="eulink"/> 8&nbsp;mg/kg in feed for egg laying hens and 25&nbsp;mg/kg in feed for other poultry and salmonids.
	It was first isolated in edible mushrooms. It has also been found in ], ], ], and ] such as ], ], ] and ].<ref name="eulink"/>
			Canthaxanthin is a potent lipid-soluble antioxidant.<ref name="Surai2012-1">{{cite journal|last= Surai|first= P.F.|title= The Antioxidant Properties of Canthaxanthin and Its Potential Effects in the Poultry Eggs and on Embryonic Development of the Chick, Part 1|journal= World's Poultry Science Journal|year= 2012|volume= 68|issue= 3|pages= 465–476|doi= 10.1017/S0043933912000578|s2cid= 92297763}}</ref><ref name="Surai2012-2">{{cite journal|last= Surai|first= P.F.|title= The Antioxidant Properties of Canthaxanthin and Its Potential Effects in the Poultry Eggs and on Embryonic Development of the Chick, Part 2|journal= World's Poultry Science Journal|year= 2012|volume= 68|issue= 4|pages= 717–726|doi= 10.1017/S0043933912000840|s2cid= 86113041}}</ref> The biological functions of canthaxanthin are related, at least in part, to its ability to function as an antioxidant (free radical scavenging/vitamin E sparing) in animal tissues.<ref>{{cite journal|last= Surai|first= A.P.|author2= Surai, P.F.|author3= Steinberg, W.|author4= Wakeman, W.G.|author5= Speake, B.K.|author6= Sparks, N.H.C.|title= Effect of canthaxanthin content of the maternal diet on the antioxidant system of the developing chick|journal= British Poultry Science|year= 2003|volume= 44|issue= 4|pages= 612–619|doi= 10.1080/00071660310001616200|pmid= 14584852|s2cid= 42795189}}<!--|access-date= 7 July 2011--></ref>
	In the ], canthaxanthin is allowed by law to be added to sausages of Strasbourg (mainly to those exported to France), as well as ] feed, salmon feed and poultry feed.<ref>{{cite web|last=Food Standards Agency UK|title=Canthaxanthin - your questions answered|url=http://www.food.gov.uk/multimedia/webpage/canthaxanthin_qanda/|accessdate=7 July 2011|date=Monday 12 April 2010}}</ref> The ] limit is 80&nbsp;mg/kg of feedstuffing,<ref name="eulink"/> 8&nbsp;mg/kg in feed for egg laying hens and 25&nbsp;mg/kg in feed for other poultry and salmonids.
			== Biosynthesis ==
			Due to the commercial value of carotenoids, their biosynthesis has been studied extensively in both natural producers, and non-natural (heterologous) systems such as the bacteria ''Escherichia coli'' and yeast ''Saccharomyces cerevisiae''. Canthaxanthin biosynthesis proceeds from beta-carotene via the action of a single protein, known as a beta-carotene ketolase, that is able to add a ] group to carbon 4 and 4' of the beta carotene molecule.
			Although functionally identical, several distinct beta-carotene ketolase proteins are known. That is to say they differ from an evolutionary perspective in their primary amino acid/protein sequence. They are different proteins that complete the same function. Thus, bacterial (CrtW) and micro-algal beta-carotene ketolase proteins such as ''BKT'' isolated from '']''<ref>{{cite journal|last= Lotan|first= T|author2= Hirschberg, J|title= Cloning and expression in Escherichia coli of the gene encoding beta-C-4-oxygenase, that converts beta-carotene to the ketocarotenoid canthaxanthin in Haematococcus pluvialis|journal= FEBS Letters|date= May 8, 1995|volume= 364|issue= 2|pages= 125–8|pmid= 7750556|doi= 10.1016/0014-5793(95)00368-J|s2cid= 25187964|doi-access= free|bibcode= 1995FEBSL.364..125L}}</ref> are known.
			Due to the nature of canthaxanthin, relative to ] (a carotenoid of significant commercial value) these beta-carotene ketolase proteins have been studied extensively.<ref>{{cite journal|last= Scaife|first= M.A.|author2= Burja, A.M.|author3= Wright, P.C.|title= Characterization of cyanobacterial beta-carotene ketolase and hydroxylase genes in Escherichia coli, and their application for astaxanthin biosynthesis|journal= Biotechnology and Bioengineering|date= 1 August 2009|volume= 103|issue= 5|pages= 944–55|pmid= 19365869|doi= 10.1002/bit.22330|s2cid= 10425589}}</ref><ref>{{cite journal|last= Fraser|first= P.D.|author2= Miura, Y.|author3= Misawa, N.|title= In vitro characterization of astaxanthin biosynthetic enzymes|journal= The Journal of Biological Chemistry|date= 7 March 1997|volume= 272|issue= 10|pages= 6128–35|pmid= 9045623|doi= 10.1074/jbc.272.10.6128|doi-access= free}}</ref> An ''E. coli'' based production system has been developed, that achieved canthanaxanthin production at 170&nbsp;mg/L in lab scale fermentation.<ref>{{cite journal|last=Scaife|first=Mark A.|author2=Ma, Cynthia A. |author3=Norman, Andrew |author4= Armenta, Roberto E. |title=Progress toward an Escherichia coli canthaxanthin bioprocess|journal=Process Biochemistry|date=1 October 2012|volume=47|issue=12|pages=2500–2509|doi=10.1016/j.procbio.2012.10.012}}</ref>
	== Presence in fish ==		== Presence in fish ==
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	== Presence in birds ==		== Presence in birds ==
	Canthaxanthin is a potent radical scavenger and nature’s most powerful lipid-soluble antioxidant. The biological functions of canthaxanthin will be related, at least in part, to its ability to function as an anti-oxidant (free radical scavenging / vitamin E sparing) in animal tissues.<ref>{{cite journal|last=Surai|first=A. P.|coauthors=Surai, P. F.; Steinberg, W.; Wakeman, W. G.; Speake, B. K.; Sparks, N. H. C.|title=Effect of canthaxanthin content of the maternal diet on the antioxidant system of the developing chick|journal=Br. Poult. Sci.|year=2003|volume=44|issue=4|pages=612–619|doi=10.1080/00071660310001616200|accessdate=7 July 2011}}</ref> The anti-oxidant characteristics of canthaxanthin have been studied by a number of authors and experiments have shown that the presence of canthaxanthin can potentially help to reduce oxidation in a number of tissues including broiler meat and the chick embryo. In the egg, canthaxanthin is transferred from yolk to the developing embryo where it might help to protect the developing bird against oxidative damage, particularly during the sensitive periods of hatching and early posthatch life.		The antioxidant characteristics of canthaxanthin have been studied by a number of authors and experiments have shown that the presence of canthaxanthin can potentially help to reduce oxidation in a number of tissues including broiler meat and the chick embryo. In the egg, canthaxanthin is transferred from yolk to the developing embryo where it might help to protect the developing bird against oxidative damage, particularly during the sensitive periods of hatching and early posthatch life.<ref name="Surai2012-1"/><ref name="Surai2012-2"/> Flamingos are known to produce crop milk containing canthaxanthin for this purpose.
	== Effects on human pigmentation ==		== Effects on human pigmentation and health ==
	When ingested for the purpose of simulating a tan, its deposition in the ] imparts a golden orange hue to the skin.<ref name="Andrews">James, William; Berger, Timothy; Elston, Dirk (2005). ''Andrews' Diseases of the Skin: Clinical Dermatology''. (10th ed.). Saunders. ISBN 0-7216-2921-0.</ref>{{rp|860}}		When ingested for the purpose of simulating a tan, its deposition in the ] imparts a golden orange hue to the skin.<ref name="Andrews">James, William; Berger, Timothy; Elston, Dirk (2005). ''Andrews' Diseases of the Skin: Clinical Dermatology''. (10th ed.). Saunders. {{ISBN|0-7216-2921-0}}.</ref>{{rp|860}}
	In the late 1980s, the safety of canthaxanthin as a feed and a food additive was drawn into question as a result of a completely un-related use of the same carotenoid. A reversible deposition of canthaxanthin crystals was discovered in the retina of a limited number of people who had consumed very high amounts of canthaxanthin via sun-tanning pills – after stopping the pills, the deposits disappeared and the health of those people affected was fully recovered. However, the level of canthaxanthin intake in the affected individuals was many times greater than that which could ever be consumed via poultry products - to reach a similar intake, an individual would have to eat daily more than 50 eggs produced by layers fed practical levels of canthaxanthin in their diets. Although this incidence was totally unrelated and very different to the feed or food use of canthaxanthin, as a link had been drawn between canthaxanthin and human health, it was important that the use of canthaxanthin as a feed and food additive should be reviewed in detail by the relevant authorities, both in the EU and at an international level. The first stage of this review process was completed in 1995 with the publication by JECFA (Joint Experts Committee on Food Additives – a joint WHO/FAO committee) of an Acceptable Daily Intake (ADI) for canthaxanthin of 0.03&nbsp;mg/kg bodyweight. The work of JECFA was subsequently reviewed and accepted within the EU by the SCF (EU Scientific Committee for Food) in 1997. The conclusion of both these committees was that canthaxanthin is safe for humans. Recently (2010), the EFSA Panel on Food Additives and Nutrient sources added to food (ANS) published a revised version of the safety assessment of Canthaxanthin, reconfirming the already set ADI. The FDA has no "tanning pills" approved for sale in the United States. In spite of this, there are companies that continue to market such products, some of which contain canthaxanthin. The FDA considers such items "adulterated cosmetics" and as a result sent "Warning Letters" to the firms citing such products as containing "a color additive that is unsafe within the meaning of section 721(a) of the FD&C Act (FD&C Act, sec. 601(e))."<ref></ref>		In the late 1980s, the safety of canthaxanthin as a feed and a ] was drawn into question as a result of a completely un-related use of the same carotenoid. A reversible deposition of canthaxanthin crystals was discovered in the retina of a limited number of people who had consumed very high amounts of canthaxanthin via sun-] – after stopping the pills, the deposits disappeared and the health of those people affected was fully recovered. However, the level of canthaxanthin intake in the affected individuals was many times greater than that which could ever be consumed via poultry products - to reach a similar intake, an individual would have to consume more than 50 eggs per day, produced by hens fed practical levels of canthaxanthin in their diets. Moreover, it was demonstrated by Hueber et al. that ingestions of canthaxanthin cause no long-term adverse effects, and that the phenomenon of crystal deposition on the retina is reversible and does not result in morphological changes.<ref>{{cite web| url=https://www.riotanningtablets.co.uk |title= Sun less Tanning }} Monday, 26 August 2019</ref><ref>{{cite journal|last=Hueber|first=A.|author2=Rosentreter, A. |author3=Severin, M. |title=Canthaxanthin Retinopathy: Long-Term Observations|journal=Ophthalmic Research|year=2011|volume=46|issue=2|pages=103–106|doi=10.1159/000323813|pmid=21346389|s2cid=7495247}}</ref> Although this incidence was totally unrelated and very different from the feed or food use of canthaxanthin, as a link had been drawn between canthaxanthin and human health, it was important that the use of canthaxanthin as a feed and food additive should be reviewed in detail by the relevant authorities, both in the EU and at an international level. The first stage of this review process was completed in 1995 with the publication by ] (JECFA) of an Acceptable Daily Intake (ADI) for canthaxanthin of 0.03&nbsp;mg/kg bodyweight. The work of JECFA was subsequently reviewed and accepted within the EU by the SCF (EU Scientific Committee for Food) in 1997. The conclusion of both these committees was that canthaxanthin is safe for humans. Recently (2010), the EFSA Panel on Food Additives and Nutrient sources added to food (ANS) published a revised version of the safety assessment of Canthaxanthin, reconfirming the already set ADI. The ] (FDA) has no "tanning pills" approved for sale in the United States. In spite of this, there are companies that continue to market such products, some of which contain canthaxanthin. The FDA considers such items "adulterated cosmetics" and as a result sent ] to the firms citing such products as containing "a color additive that is unsafe within the meaning of section 721(a) of the FD&C Act (FD&C Act, sec. 601(e))."<ref>{{Cite web |url=http://www.cfsan.fda.gov/~dms/coscanth.html |archive-url=https://web.archive.org/web/20090528184331/http://www.cfsan.fda.gov/~dms/coscanth.html |archive-date=May 28, 2009 |title=Warning Letters Cite Cosmetics as Adulterated Due to Violative Use of the Color Additive Canthaxanthin |date=April 5, 2005 |access-date=May 13, 2012}}</ref>
			According to the FDA,<ref>{{cite web |url=https://www.fda.gov/cdrh/fdaandyou/issue03.html#4 |archive-url=https://web.archive.org/web/20090119142356/https://www.fda.gov/cdrh/fdaandyou/issue03.html#4 |archive-date=January 19, 2009 |work=FDA & You, Issue #3 |date=Spring–Summer 2003 |title=Sun Safety: Protect the Skin You're In! |publisher=]}}</ref>
	According to the FDA:
	:<blockquote>Tanning pills have been associated with health problems, including an eye disorder called ''canthaxanthin'' retinopathy, which is the formation of yellow deposits on the eye's retina. ''Canthaxanthin'' has also been reported to cause liver injury and a severe itching condition called ], according to the ].<ref>From ''Issue #3 - Spring/Summer 2003 - Sun Safety: Protect the Skin You’re In!''</ref></blockquote>		:{{blockquote|Tanning pills have been associated with health problems, including an eye disorder called ], which is the formation of yellow deposits on the eye's retina. Canthaxanthin has also been reported to cause liver injury and a severe itching condition called ], according to the ].}}
	== References ==		== References ==
			{{reflist|32em}}
	<references/>
	{{Carotenoids}}		{{Carotenoids}}
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