CANTHAXANTHIN (CHEM004988)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:57:02 UTC
Update Date2016-11-09 01:09:27 UTC
Accession NumberCHEM004988
Identification
Common NameCANTHAXANTHIN
ClassSmall Molecule
DescriptionA carotenone that consists of beta,beta-carotene bearing two oxo substituents at positions 4 and 4'.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass564.854 g/mol
Monoisotopic Mass564.397 g/mol
CAS Registry Number514-78-3
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
SMILESC\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 IdentifierInChI=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
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 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1213290000-9719da4262f629366440Spectrum
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-016u-2920000000-bf9cf6df0a7dd95006afSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-03xr-1951160000-000e09c523a6561e2707Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0ika-0296420000-b19acaaf1afb00cf9fc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0001910000-a35bcbebdd90994a2f3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01pc-0025970000-423e791499171562736fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-0920000000-639f9f3228c4c2396f90Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0892000000-742de39d976dca6ca15dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0492060000-fef850b3839e24097342Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0322390000-eee87729039394ef2242Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0596730000-20a001319fad4fff32bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hft-1598720000-1c73c717692c05971680Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-3323cd427776bc321533Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000090000-3a19aa461bcf5ed2f3a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1454390000-1441e3b85e17841ccd5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07bs-0372890000-a2aa999a4582f599bbd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0465940000-6e2f92273172d86d6e7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvs-0124900000-ddb1b9f3fe5c49bcb826Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001090000-3588cb304de167acfcd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-0215290000-5a34259c64d9108eece6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0229020000-8b0c64a50d1fea3655efSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003154
FooDB IDFDB015890
Phenol Explorer IDNot Available
KNApSAcK IDC00000922
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3597
PDB IDNot Available
Wikipedia LinkCanthaxanthin
Chemspider ID4444639
ChEBI ID3362
PubChem Compound ID5281227
Kegg Compound IDC08583
YMDB IDNot Available
ECMDB IDM2MDB005231
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22334741
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22353211
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22366116
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22418926
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22428120
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22451081
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22455145
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24097248
9. 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.
10. 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.
11. 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.
12. 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.