Canthaxanthin

Canthaxanthin[1]
Skeletal formula of canthaxanthin
Space-filling model of the canthaxanthin molecule
Names
IUPAC name
β,β-Carotene-4,4′-dione
Systematic IUPAC name
3,3′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,4,4-trimethylcyclohex-2-en-1-one)
Other names
  • 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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.444 Edit this at Wikidata
E number E161g (colours)
UNII
  • InChI=1S/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+ checkY
    Key: FDSDTBUPSURDBL-OQWFGLAJSA-N checkY
  • 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+
    Key: FDSDTBUPSURDBL-OQWFGLAJBT
  • 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
Properties
C40H52O2
Molar mass 564.82 g/mol
Appearance Violet crystals
Melting point 211 to 212 °C (412 to 414 °F; 484 to 485 K) (decomposition)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Canthaxanthin /ˌkænθəˈzænθɪn/ ⓘ is a keto-carotenoid[3] pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. The chemical formula of canthaxanthin is C40H52O2.[4] It was first isolated in edible mushrooms. It has also been found in green algae, bacteria, crustaceans, and bioaccumulates in fish such as carp, golden grey mullet, seabream and trush wrasse.[4]

Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States[5] and the EU;[6] however, it is not approved for use in Australia and New Zealand.[7] It is generally authorized for feed applications in at least the following countries: US,[8] Canada,[9] EU.[10] In the EU, canthaxanthin is allowed by law to be added to trout feed, salmon feed and poultry feed.[11] The European Union limit is 80 mg/kg of feedstuffs,[4] 8 mg/kg in feed for egg laying hens and 25 mg/kg in feed for other poultry and salmonids.

Canthaxanthin is a potent lipid-soluble antioxidant.[12][13] 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.[14]

  1. ^ Merck Index, 11th Edition, 1756.
  2. ^ Petracek, F. J.; Zechmeister, L. (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.
  3. ^ 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
  4. ^ "Colour Additive Status List". Food and Drug Administration. Retrieved 2011-10-27.
  5. ^ "Current EU approved additives and their E Numbers". Food Standards Agency. 14 March 2012. Retrieved Dec 19, 2012.
  6. ^ "Standard 1.2.4 - Labelling of ingredients". Australia New Zealand Food Standards Code. 8 September 2011. Retrieved 2011-10-27.
  7. ^ "Code of Federal Regulations Title 21, 1 April 2012". Food and Drug Administration. Retrieved 2013-06-21.
  8. ^ "Feeds Regulations, 1983 (SOR/83-593)". Justice Laws, Canada. Archived from the original on 2013-06-28. Retrieved 2013-06-21.
  9. ^ "European Union Register of Feed Additives, Revision 162 released 7 June 2013" (PDF). European Commission. Retrieved 2013-06-21.
  10. ^ Food Standards Agency UK (12 April 2010). "Canthaxanthin - your questions answered". Archived from the original on 23 March 2013. Retrieved 19 December 2012.
  11. ^ Surai, P.F. (2012). "The Antioxidant Properties of Canthaxanthin and Its Potential Effects in the Poultry Eggs and on Embryonic Development of the Chick, Part 1". World's Poultry Science Journal. 68 (3): 465–476. doi:10.1017/S0043933912000578. S2CID 92297763.
  12. ^ Surai, P.F. (2012). "The Antioxidant Properties of Canthaxanthin and Its Potential Effects in the Poultry Eggs and on Embryonic Development of the Chick, Part 2". World's Poultry Science Journal. 68 (4): 717–726. doi:10.1017/S0043933912000840. S2CID 86113041.
  13. ^ Surai, A.P.; Surai, P.F.; Steinberg, W.; Wakeman, W.G.; Speake, B.K.; Sparks, N.H.C. (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. PMID 14584852. S2CID 42795189.