Canthaxanthin

Basic Info

Common NameCanthaxanthin(F05739)
2D Structure
FRCD IDF05739
CAS Number514-78-3
PubChem CID5281227
FormulaC40H52O2
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-oxocyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one

InChI Key

FDSDTBUPSURDBL-DKLMTRRASA-N

InChI

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+

Canonical SMILES

CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)CCC2(C)C)C)C)C

Isomeric SMILES

CC1=C(C(CCC1=O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C(=O)CCC2(C)C)C)\C)\C)/C)/C

Synonyms
        
            Cantaxanthin
        
            Canthaxanthin
        
            514-78-3
        
            Canthaxanthine
        
            Orobronze
        
            Carophyll Red
        
            beta,beta-Carotene-4,4'-dione
        
            Food orange 8
        
            Cantaxanthine
        
            Roxanthin Red 10
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassTetraterpenoids
Intermediate Tree NodesCarotenoids
Direct ParentXanthophylls
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsXanthophyll - Cyclohexenone - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight564.854
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count10
Complexity1270
Monoisotopic Mass564.397
Exact Mass564.397
XLogP11.4
Formal Charge0
Heavy Atom Count42
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count9
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9261
Human Intestinal AbsorptionHIA+0.9971
Caco-2 PermeabilityCaco2+0.7950
P-glycoprotein SubstrateSubstrate0.5280
P-glycoprotein InhibitorInhibitor0.8592
Non-inhibitor0.6769
Renal Organic Cation TransporterNon-inhibitor0.7542
Distribution
Subcellular localizationMitochondria0.7381
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8037
CYP450 2D6 SubstrateNon-substrate0.8752
CYP450 3A4 SubstrateSubstrate0.7204
CYP450 1A2 InhibitorNon-inhibitor0.8436
CYP450 2C9 InhibitorNon-inhibitor0.8125
CYP450 2D6 InhibitorNon-inhibitor0.8848
CYP450 2C19 InhibitorNon-inhibitor0.6046
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7390
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8886
Non-inhibitor0.8527
AMES ToxicityNon AMES toxic0.9206
CarcinogensNon-carcinogens0.8109
Fish ToxicityHigh FHMT0.7632
Tetrahymena Pyriformis ToxicityHigh TPT0.8680
Honey Bee ToxicityHigh HBT0.8005
BiodegradationNot ready biodegradable0.7419
Acute Oral ToxicityIII0.7546
Carcinogenicity (Three-class)Non-required0.5149
Model Value Unit
Absorption
Aqueous solubility-2.8643LogS
Caco-2 Permeability1.9906LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0722LD50, mol/kg
Fish Toxicity1.1319pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2883pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pig,FatJapan0.1ppm
Cattle,FatJapan0.1ppm
Other Terrestrial Mammals,FatJapan0.1ppm
HoneyJapan0.1ppm
Other Aquatic AnimalJapan0.1ppm
CrustaceansJapan0.1ppm
Shelled MolluscasJapan0.1ppm
Other FishJapan0.1ppm
PerciformesJapan0.1ppm
AnguilliformesJapan0.1ppm
Other Poultry,EggsJapan0.1ppm
Other Poultry Animals,Edible OffalJapan0.1ppm
Other Poultry Animals,KidneyJapan0.1ppm
Other Poultry Animals,LiverJapan0.1ppm
Other Poultry Animals,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
MilkJapan0.1ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Pig,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.1ppm

References

TitleJournalDatePubmed ID
Exploration of interaction of canthaxanthin with human serum albumin byspectroscopic and molecular simulation methods.Luminescence2018 Mar29251407
A meta-analysis on the effect of canthaxanthin on egg production in brown egglayers.Poult Sci2018 Jan 129077922
Canthaxanthin: From molecule to function.Mol Nutr Food Res2017 Jun27687695
HPLC Quantification of astaxanthin and canthaxanthin in Salmonidae eggs.Biomed Chromatogr2017 Apr27615726
Effects of recombinant lycopene dietary supplement on the egg quality and bloodcharacteristics of laying quails.J Biosci Bioeng2015 Nov26100321
Inclusion of Palmaria palmata (red seaweed) in Atlantic salmon diets: effects on the quality, shelf-life parameters and sensory properties of fresh and cookedsalmon fillets.J Sci Food Agric2015 Mar 3024852938
Response surface methodology toward the optimization of high-energy carotenoidextraction from Aristeus antennatus shrimp.Anal Chim Acta2015 Jun 226002215
Canthaxanthin biosynthesis by Dietzia natronolimnaea HS-1: effects of inoculationand aeration rate.Braz J Microbiol2014 Aug 2925242927
Determination of egg yolk xanthophylls by isocratic high-performance liquidchromatography.J Chromatogr A2013 Nov 2924139505
Astaxanthin and canthaxanthin (xanthophyll) as supplements in rainbow trout diet:in vivo assessment of residual levels and contributions to human health.J Agric Food Chem2013 Nov 2024156372
[Determination of canthaxanthin and astaxanthin in egg yolks by reversed phasehigh performance liquid chromatography with diode array detection].Sichuan Da Xue Xue Bao Yi Xue Ban2012 Jan22455145
Use of response surface methodology in a fed-batch process for optimization oftricarboxylic acid cycle intermediates to achieve high levels of canthaxanthinfrom Dietzia natronolimnaea HS-1.J Biosci Bioeng2010 Apr20226378
Interactions between canthaxanthin and lipid membranes--possible mechanisms of canthaxanthin toxicity.Cell Mol Biol Lett200919214394
Use of Tween 40 and Tween 80 to deliver a mixture of phytochemicals to human colonic adenocarcinoma cell (CaCo-2) monolayers.Br J Nutr2004 May15137928
Nickel peroxide induced oxidation of canthaxanthin.J Agric Food Chem1999 May10552466
Isolation and identification of a major urinary canthaxanthin metabolite in rats.Int J Vitam Nutr Res1999 Jul10450532
Dietary fiber reduces the antioxidative effect of a carotenoid andalpha-tocopherol mixture on LDL oxidation ex vivo in humans.Eur J Nutr1999 Dec10784384
Relative stability of carotenoid radical cations and homologue tocopheroxylradicals. A real time kinetic study of antioxidant hierarchy.FEBS Lett1997 Nov 179409729
Occurrence of birefringent retinal inclusions in cynomolgus monkeys after highdoses of canthaxanthin.Invest Ophthalmol Vis Sci1997 Mar9071228
Neonatal immune response and growth performance of chicks hatched from singlecomb White Leghorn breeders fed diets supplemented with beta-carotene,canthaxanthin, or lutein.Poult Sci1995 May7603961