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Record Information
Version1.0
Created at2006-05-22 15:12:37 UTC
Updated at2021-08-19 20:22:27 UTC
NP-MRD IDNP0000007
Secondary Accession NumbersNone
Natural Product Identification
Common NameCanthaxanthin
DescriptionCanthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240 ). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4' of the beta carotene molecule.
Structure
Data?1628564076
Synonyms
ValueSource
4,4'-Dioxo-beta-caroteneChEBI
all-trans-beta-Carotene-4,4'-dioneChEBI
Carophyll redChEBI
e 161gChEBI
FOOD Orange 8ChEBI
OrobronzeChEBI
4,4'-Dioxo-b-caroteneGenerator
4,4'-Dioxo-β-caroteneGenerator
all-trans-b-Carotene-4,4'-dioneGenerator
all-trans-Β-carotene-4,4'-dioneGenerator
4,4'-Diketo-b-caroteneHMDB
4,4'-Diketo-beta-caroteneHMDB
all-trans,beta-Carotene-4,4'-dioneHMDB
beta,beta-Carotene-4,4'-dioneHMDB
CantaxanthinHMDB
CantaxanthineHMDB
CanthaxanthineHMDB
L-Orange 7HMDB
Roxanthin red 10HMDB
Chemical FormulaC40H52O2
Average Mass564.8540 Da
Monoisotopic Mass564.39673 Da
IUPAC Name2,4,4-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
Traditional Namecanthaxanthin
CAS Registry Number514-78-3
SMILES
[H]/C(=C(/[H])\C(\[H])=C(\C(\[H])=C(/[H])\C(\[H])=C(\C(\[H])=C(/[H])C1=C(C(=O)C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])/C([H])([H])[H])/C([H])([H])[H])/C(/[H])=C(/C(/[H])=C(\[H])/C(/[H])=C(/C(/[H])=C(\[H])C1=C(C(=O)C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H]
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+
InChI KeyFDSDTBUPSURDBL-DKLMTRRASA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anabaena flos-aquaeKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Corbicula japonicaKNApSAcK Database
Corbicula sandaiKNApSAcK Database
Solanum tuberosumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Agrobacterium aurantiacumKNApSAcK Database
Alcaligenes PC1KNApSAcK Database
Cantharellus cinnabarinusKNApSAcK Database
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211 - 212 °Chttps://en.wikipedia.org/wiki/Canthaxanthin
Boiling Point717.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.5e-10 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.526 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.00046 g/LALOGPS
logP8.71ALOGPS
logP9.79ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity193 m³·mol⁻¹ChemAxon
Polarizability72.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0003154
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015890
KNApSAcK IDC00000922
Chemspider ID4444639
KEGG Compound IDC08583
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCanthaxanthin
METLIN ID3597
PubChem Compound5281227
PDB IDNot Available
ChEBI ID3362
Good Scents IDrw1365301
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Rosa AP, Scher A, Sorbara JO, Boemo LS, Forgiarini J, Londero A: Effects of canthaxanthin on the productive and reproductive performance of broiler breeders. Poult Sci. 2012 Mar;91(3):660-6. doi: 10.3382/ps.2011-01582. [PubMed:22334741 ]
  6. Mayne ST, Parker RS: Antioxidant activity of dietary canthaxanthin. Nutr Cancer. 1989;12(3):225-36. doi: 10.1080/01635588909514022. [PubMed:2505240 ]