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Showing NP-Card for Canthaxanthin (NP0000007)

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Record Information
Version1.0
Created at2006-05-22 15:12:37 UTC
Updated at2020-09-11 01:32:46 UTC
NP-MRD IDNP0000007
Secondary Accession NumbersNone
Natural Product Identification
Common NameCanthaxanthin
DescriptionCanthaxanthin, also known as carophyll red or e 161G, 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. Thus, canthaxanthin is considered to be an isoprenoid lipid molecule. Canthaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Plantae
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
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 Solubility0.00046 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
User Submitted Data
Not Available
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
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 ]