Canthaxanthin: Difference between revisions
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| MeltingPt=211–212 °C (decomposition)<ref>{{cite journal|last=Petracek|first=F. J.|coauthors=Zechmeister, L.|title=Reaction of beta- |
| 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=[[Journal of the American Chemical Society]] |year=1956 |volume=78 |issue=7 |pages=1427–1434 |doi=10.1021/ja01588a044}}</ref> |
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'''Canthaxanthin''' ({{IPAc-en|audio=canthaxanthin-pronunciation.ogg|ˌ|k|æ|n|θ|ə|ˈ|z|æ|n|θ|ɪ|n}}) is a [[carotenoid]] pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as [[terpenoid]]s. The chemical formula of canthaxanthin is C<SUB>40</SUB>H<SUB>52</SUB>O<SUB>2</SUB>.<ref name="eulink">[http://ec.europa.eu/food/fs/sc/scan/out81_en.pdf#search=%22Canthaxanthin%22 Opinion on the use of canthaxanthin in feedingstuffs for salmon ...]</ref> It has [[E number]] E161g and is approved for use in the EU and USA<ref>US FDA:{{cite web |url=http://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm106626.htm |title=Colour Additive Status List |accessdate=2011-10-27}}</ref>. |
'''Canthaxanthin''' ({{IPAc-en|audio=canthaxanthin-pronunciation.ogg|ˌ|k|æ|n|θ|ə|ˈ|z|æ|n|θ|ɪ|n}}) is a [[carotenoid]] pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as [[terpenoid]]s. The chemical formula of canthaxanthin is C<SUB>40</SUB>H<SUB>52</SUB>O<SUB>2</SUB>.<ref name="eulink">[http://ec.europa.eu/food/fs/sc/scan/out81_en.pdf#search=%22Canthaxanthin%22 Opinion on the use of canthaxanthin in feedingstuffs for salmon ...]</ref> It has [[E number]] E161g and is approved for use in the EU and USA<ref>US FDA:{{cite web |url=http://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm106626.htm |title=Colour Additive Status List |accessdate=2011-10-27}}</ref> however it is not approved for usage in Australia and New Zealand.<ref>Australia New Zealand Food Standards Code{{cite web |url=http://www.comlaw.gov.au/Details/F2011C00827 |title=Standard 1.2.4 - Labelling of ingredients |accessdate=2011-10-27}}</ref> |
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It was first isolated in edible mushrooms. It has also been found in [[green |
It was first isolated in edible mushrooms. It has also been found in [[green alga]]e, [[bacteria]], [[crustacean]]s, and [[fish]] such as [[carp]], [[golden mullet]], [[seabream]] and [[trush wrasse]].<ref name="eulink"/> |
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In the [[European Union|EU]], canthaxanthin is allowed by law to be added to sausages of Strasbourg (mainly to those exported to France), as well as [[trout]] 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 [[European Union]] limit is 80 mg/kg of feedstuffing,<ref name="eulink"/> 8 mg/kg in feed for egg laying hens and 25 mg/kg in feed for other poultry and salmonids. |
In the [[European Union|EU]], canthaxanthin is allowed by law to be added to sausages of Strasbourg (mainly to those exported to France), as well as [[trout]] 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 [[European Union]] limit is 80 mg/kg of feedstuffing,<ref name="eulink"/> 8 mg/kg in feed for egg laying hens and 25 mg/kg in feed for other poultry and salmonids. |
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== Presence in birds == |
== Presence in birds == |
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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= |
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=British Poultry Science |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. |
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== Effects on human pigmentation == |
== Effects on human pigmentation == |
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When ingested for the purpose of simulating a tan, its deposition in the [[panniculus]] 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 [[panniculus]] 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}} |
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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 [[Joint FAO/WHO Expert Committee on Food Additives]] (JECFA) of an Acceptable Daily Intake (ADI) for canthaxanthin of 0.03 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. |
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 [[Joint FAO/WHO Expert Committee on Food Additives]] (JECFA) of an Acceptable Daily Intake (ADI) for canthaxanthin of 0.03 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 [[Food and Drug Administration]] (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>{{Cite web |url=http://www.cfsan.fda.gov/~dms/coscanth.html |archiveurl=http://web.archive.org/web/20090528184331/http://www.cfsan.fda.gov/~dms/coscanth.html |archivedate=May 28, 2009 |title=Warning Letters Cite Cosmetics as Adulterated Due to Violative Use of the Color Additive Canthaxanthin |date=April 5, 2005 |accessdate=May 13, 2012}}</ref> |
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According to the FDA,<ref>{{cite web |url=http://www.fda.gov/cdrh/fdaandyou/issue03.html#4 |archiveurl=http://web.archive.org/web/20090119142356/http://www.fda.gov/cdrh/fdaandyou/issue03.html#4 |archivedate=Janaury 19, 2009 |work=FDA & You, Issue #3 |date=Spring/Summer 2003 |title=Sun Safety: Protect the Skin You’re In! |publisher=[[Food and Drug Administration]]}}</ref> |
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:<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 [[urticaria]], according to the [[American Academy of Dermatology|AAD]].</blockquote> |
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== References == |
== References == |
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{{reflist|32em}} |
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<references/> |
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{{Carotenoids}} |
{{Carotenoids}} |
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Revision as of 07:34, 13 May 2012
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| Names | |
|---|---|
| IUPAC name
β,β-Carotene-4,4'-dione
| |
| Other names
Cantaxanthin, Cantaxanthine, Canthaxanthine, Carophyll Red, Roxanthin Red 10, L-Orange 7g, C.I. Food Orange 8, E161g, 2,4,4-Trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1-cyclohex-2-enone
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.007.444 |
| E number | E161g (colours) |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C40H52O2 | |
| Molar mass | 564.82 g/mol |
| Appearance | Violet crystals |
| Melting point | 211–212 °C (decomposition)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Canthaxanthin (/ˌkænθəˈzænθɪn/ ) is a carotenoid pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. The chemical formula of canthaxanthin is C40H52O2.[3] It has E number E161g and is approved for use in the EU and USA[4] however it is not approved for usage in Australia and New Zealand.[5]
It was first isolated in edible mushrooms. It has also been found in green algae, bacteria, crustaceans, and fish such as carp, golden mullet, seabream and trush wrasse.[3]
In the EU, canthaxanthin is allowed by law to be added to sausages of Strasbourg (mainly to those exported to France), as well as trout feed, salmon feed and poultry feed.[6] The European Union limit is 80 mg/kg of feedstuffing,[3] 8 mg/kg in feed for egg laying hens and 25 mg/kg in feed for other poultry and salmonids.
Presence in fish
Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon.[3] Canthaxanthin is used in farm-raised trout.[3] Canthaxanthin is used in combination with astaxanthin for some salmon feeds.[3]
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.[7] 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.
Effects on human pigmentation
When ingested for the purpose of simulating a tan, its deposition in the panniculus imparts a golden orange hue to the skin.[8]: 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 Joint FAO/WHO Expert Committee on Food Additives (JECFA) of an Acceptable Daily Intake (ADI) for canthaxanthin of 0.03 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 Food and Drug Administration (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))."[9]
According to the FDA,[10]
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 urticaria, according to the AAD.
References
- ^ Merck Index, 11th Edition, 1756.
- ^ Petracek, F. J. (1956). "Reaction of beta-carotene with N-bromosuccinimide: the formation and conversions of some polyene ketones". Journal of the American Chemical Society. 78 (7): 1427–1434. doi:10.1021/ja01588a044.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ a b c d e f Opinion on the use of canthaxanthin in feedingstuffs for salmon ...
- ^ US FDA:"Colour Additive Status List". Retrieved 2011-10-27.
- ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
- ^ Food Standards Agency UK (Monday 12 April 2010). "Canthaxanthin - your questions answered". Retrieved 7 July 2011.
{{cite web}}: Check date values in:|date=(help) - ^ Surai, A. P. (2003). "Effect of canthaxanthin content of the maternal diet on the antioxidant system of the developing chick". British Poultry Science. 44 (4): 612–619. doi:10.1080/00071660310001616200.
{{cite journal}}:|access-date=requires|url=(help); Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ James, William; Berger, Timothy; Elston, Dirk (2005). Andrews' Diseases of the Skin: Clinical Dermatology. (10th ed.). Saunders. ISBN 0-7216-2921-0.
- ^ "Warning Letters Cite Cosmetics as Adulterated Due to Violative Use of the Color Additive Canthaxanthin". April 5, 2005. Archived from the original on May 28, 2009. Retrieved May 13, 2012.
- ^ "Sun Safety: Protect the Skin You're In!". FDA & You, Issue #3. Food and Drug Administration. Spring/Summer 2003. Archived from the original on Janaury 19, 2009.
{{cite web}}: Check date values in:|date=and|archivedate=(help)