Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:37 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003154
Secondary Accession Numbers
  • HMDB03154
Metabolite 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?1582752264
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
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
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+258.27830932474
DeepCCS[M-H]-256.45330932474
DeepCCS[M-2H]-289.69530932474
DeepCCS[M+Na]+263.88430932474
AllCCS[M+H]+252.032859911
AllCCS[M+H-H2O]+250.232859911
AllCCS[M+NH4]+253.632859911
AllCCS[M+Na]+254.132859911
AllCCS[M-H]-225.132859911
AllCCS[M+Na-2H]-228.332859911
AllCCS[M+HCOO]-232.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CanthaxanthinC\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)C5761.4Standard polar33892256
CanthaxanthinC\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)C4918.2Standard non polar33892256
CanthaxanthinC\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)C4913.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Canthaxanthin,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O4783.5Semi standard non polar33892256
Canthaxanthin,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O4448.4Standard non polar33892256
Canthaxanthin,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O4555.3Standard polar33892256
Canthaxanthin,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C4646.8Semi standard non polar33892256
Canthaxanthin,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C4280.2Standard non polar33892256
Canthaxanthin,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C4526.0Standard polar33892256
Canthaxanthin,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O5005.6Semi standard non polar33892256
Canthaxanthin,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O4641.7Standard non polar33892256
Canthaxanthin,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O4645.6Standard polar33892256
Canthaxanthin,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C5082.5Semi standard non polar33892256
Canthaxanthin,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C4641.4Standard non polar33892256
Canthaxanthin,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C4668.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Canthaxanthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1213290000-9719da4262f6293664402017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOFsplash10-016u-2920000000-bf9cf6df0a7dd95006af2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOFsplash10-03xr-1951160000-000e09c523a6561e27072012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin Linear Ion Trap , positive-QTOFsplash10-0ika-0296420000-b19acaaf1afb00cf9fc12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin Linear Ion Trap , positive-QTOFsplash10-0002-0001910000-a35bcbebdd90994a2f3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin Linear Ion Trap , positive-QTOFsplash10-01pc-0025970000-423e791499171562736f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin 40V, Positive-QTOFsplash10-001i-0920000000-639f9f3228c4c2396f902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin 20V, Positive-QTOFsplash10-0ue9-0892000000-742de39d976dca6ca15d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canthaxanthin 10V, Positive-QTOFsplash10-0gb9-0492060000-fef850b3839e240973422021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 10V, Positive-QTOFsplash10-014i-0322390000-eee87729039394ef22422017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 20V, Positive-QTOFsplash10-03dj-0596730000-20a001319fad4fff32bf2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 40V, Positive-QTOFsplash10-0hft-1598720000-1c73c717692c059716802017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 10V, Negative-QTOFsplash10-03di-0000090000-3323cd427776bc3215332017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 20V, Negative-QTOFsplash10-03di-0000090000-3a19aa461bcf5ed2f3a52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 40V, Negative-QTOFsplash10-0002-1454390000-1441e3b85e17841ccd5b2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 10V, Positive-QTOFsplash10-07bs-0372890000-a2aa999a4582f599bbd72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 20V, Positive-QTOFsplash10-000b-0465940000-6e2f92273172d86d6e7d2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 40V, Positive-QTOFsplash10-0fvs-0124900000-ddb1b9f3fe5c49bcb8262021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 10V, Negative-QTOFsplash10-03di-0001090000-3588cb304de167acfcd72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 20V, Negative-QTOFsplash10-08fr-0215290000-5a34259c64d9108eece62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canthaxanthin 40V, Negative-QTOFsplash10-0002-0229020000-8b0c64a50d1fea3655ef2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1365301
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 ]
  5. Mayne ST, Parker RS: Antioxidant activity of dietary canthaxanthin. Nutr Cancer. 1989;12(3):225-36. doi: 10.1080/01635588909514022. [PubMed:2505240 ]