Record Information |
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Version | 1.0 |
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Created at | 2006-05-22 15:12:37 UTC |
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Updated at | 2020-11-24 22:12:04 UTC |
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NP-MRD ID | NP0000007 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Canthaxanthin |
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Description | Canthaxanthin, also known as carophyll red or e 161G, belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Thus, canthaxanthin is considered to be an isoprenoid lipid molecule. Canthaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | |
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Synonyms | Value | Source |
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4,4'-Dioxo-beta-carotene | ChEBI | all-trans-beta-Carotene-4,4'-dione | ChEBI | Carophyll red | ChEBI | e 161g | ChEBI | FOOD Orange 8 | ChEBI | Orobronze | ChEBI | 4,4'-Dioxo-b-carotene | Generator | 4,4'-Dioxo-β-carotene | Generator | all-trans-b-Carotene-4,4'-dione | Generator | all-trans-Β-carotene-4,4'-dione | Generator | 4,4'-Diketo-b-carotene | HMDB | 4,4'-Diketo-beta-carotene | HMDB | all-trans,beta-Carotene-4,4'-dione | HMDB | beta,beta-Carotene-4,4'-dione | HMDB | Cantaxanthin | HMDB | Cantaxanthine | HMDB | Canthaxanthine | HMDB | L-Orange 7 | HMDB | Roxanthin red 10 | HMDB |
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Chemical Formula | C40H52O2 |
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Average Molecular Weight | 564.854 |
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Monoisotopic Molecular Weight | 564.396730914 |
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IUPAC Name | 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-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one |
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Traditional Name | canthaxanthin |
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CAS Registry Number | 514-78-3 |
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SMILES | C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C |
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InChI Identifier | 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+ |
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InChI Key | FDSDTBUPSURDBL-DKLMTRRASA-N |
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Spectra |
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| | Species of Origin |
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Species | Animalia; Plantae |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Tetraterpenoids |
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Direct Parent | Xanthophylls |
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Alternative Parents | |
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Substituents | - Xanthophyll
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Paetau I, Chen H, Goh NM, White WS: Interactions in the postprandial appearance of beta-carotene and canthaxanthin in plasma triacylglycerol-rich lipoproteins in humans. Am J Clin Nutr. 1997 Nov;66(5):1133-43. [PubMed:9356530 ]
- Meyer JC, Grundmann HP, Seeger B, Schnyder UW: Plasma concentrations of beta-carotene and canthaxanthin during and after stopping intake of a combined preparation. Dermatologica. 1985;171(2):76-81. [PubMed:3930305 ]
- Rollman O, Vahlquist A: Psoriasis and vitamin A. Plasma transport and skin content of retinol, dehydroretinol and carotenoids in adult patients versus healthy controls. Arch Dermatol Res. 1985;278(1):17-24. [PubMed:4096526 ]
- Bluhm R, Branch R, Johnston P, Stein R: Aplastic anemia associated with canthaxanthin ingested for 'tanning' purposes. JAMA. 1990 Sep 5;264(9):1141-2. [PubMed:2117075 ]
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