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Record Information
Version4.0
Creation Date2006-05-22 15:12:37 UTC
Update Date2017-09-25 17:29:23 UTC
HMDB IDHMDB0003154
Secondary Accession Numbers
  • HMDB03154
StatusDetected and Quantified
Metabolite Identification
Common NameCanthaxanthin
DescriptionXanthophyll. A trans-carotenoid pigment widely distributed in nature. The compound is used as an oral suntanning agent and as a food and drug coloring agent. Oral ingestion of the compound causes canthaxanthin retinopathy. -- Pubchem; Canthaxanthin is a food additive used for farmed salmon raised in environments where astaxanthin sources are not available. Canthaxanthin gives salmon a pink color similar to pink/red species of wild salmon, while at the same time acting as an antibiotic. It has E number E161g. -- Wikipedia; The analysis of canthaxanthin content in salmon is a scientifically-accepted method to determine the origin of salmons. -- Wikipedia.
Structure
Thumb
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 Molecular Weight564.854
Monoisotopic Molecular Weight564.396730914
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
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
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
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Source:
Route of exposure:
Subcellular:
Enteral:
Biofluid and excreta:
Organ and components:
Role
Industrial application:
Process
Naturally occurring process:
Biological process:
Cellular process:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000461 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity193 m3·mol-1ChemAxon
Polarizability72.16 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-016u-2920000000-bf9cf6df0a7dd95006afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-03xr-1951160000-000e09c523a6561e2707View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ika-0296420000-b19acaaf1afb00cf9fc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0001910000-a35bcbebdd90994a2f3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01pc-0025970000-423e791499171562736fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Skin
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.07 +/- 0.06 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00900 +/- 0.0150 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0100 +/- 0.0130 uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB015890
KNApSAcK IDC00000922
Chemspider ID4444639
KEGG Compound IDC08583
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCanthaxanthin
NuGOwiki LinkHMDB0003154
METLIN ID3597
PubChem Compound5281227
PDB IDNot Available
ChEBI ID3362
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]