3,5,7,9,11,13,15,17,19-Eicosanonaen-2-one, 5,9,14,18-tetramethyl-20-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E,5E,7E,9E,11E,13E,15E,17E,19E)- (CHEM012006)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:48:19 UTC
Update Date2016-11-09 01:14:29 UTC
Accession NumberCHEM012006
Identification
Common Name3,5,7,9,11,13,15,17,19-Eicosanonaen-2-one, 5,9,14,18-tetramethyl-20-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E,5E,7E,9E,11E,13E,15E,17E,19E)-
ClassSmall Molecule
DescriptionCitranaxanthin is found in citrus. Citranaxanthin is a constituent of Sinton citrangequat (a Citrus-Poncirus-Fortunella hybrid) Citranaxanthin is a carotenoid pigment used as a food additive under the E number E161i as a food coloring. There are natural sources of citranaxanthin, but it is generally prepared synthetically. It is used as an animal feed additive to impart a yellow color to chicken fat and egg yolks.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5',6'-dihydro-5'-apo-18'-Nor-beta,psi-caroten-6'-oneHMDB
6'-Methyl-6'-apo-b-caroten-6'-oneHMDB
Chemical FormulaC33H44O
Average Molecular Mass456.702 g/mol
Monoisotopic Mass456.339 g/mol
CAS Registry Number3604-90-8
IUPAC Name(3E,5E,7E,9E,11E,13E,15E,17Z,19E)-5,9,14,18-tetramethyl-20-(2,6,6-trimethylcyclohex-1-en-1-yl)icosa-3,5,7,9,11,13,15,17,19-nonaen-2-one
Traditional Name(3E,5E,7E,9E,11E,13E,15E,17Z,19E)-5,9,14,18-tetramethyl-20-(2,6,6-trimethylcyclohex-1-en-1-yl)icosa-3,5,7,9,11,13,15,17,19-nonaen-2-one
SMILESCC(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI IdentifierInChI=1S/C33H44O/c1-26(16-11-18-28(3)21-23-31(6)34)14-9-10-15-27(2)17-12-19-29(4)22-24-32-30(5)20-13-25-33(32,7)8/h9-12,14-19,21-24H,13,20,25H2,1-8H3/b10-9+,16-11+,17-12+,23-21+,24-22+,26-14+,27-15+,28-18+,29-19-
InChI KeyPRDJTOVRIHGKNU-OZVHZJNCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.00066 g/LALOGPS
logP8.3ALOGPS
logP8.47ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)19.71ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity161.5 m³·mol⁻¹ChemAxon
Polarizability59.79 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0006-3110900000-535a0ce08b61b6b82651Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0224900000-a7046a9c26cd96ce3323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lb-0559100000-d6b0ad10fff92c819a35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002e-3449100000-ac1a1e58b354873f35f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-095b3b99e7814b919f9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-c2c522d71253bd7de068Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2333900000-6f65a7f64d8b7095203bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pds-1359600000-bb4229a052cc354c229dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q4-2619000000-d561c3becef4d8f28abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-3943100000-b2fe58f1cb6911a19650Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0006900000-8a21d96954a1d944e697Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6517900000-1cfad0a238bef00d710dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1119100000-ebb715728ee6fa1dd9ccSpectrum
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 IDHMDB0036883
FooDB IDFDB015841
Phenol Explorer IDNot Available
KNApSAcK IDC00023104
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCitranaxanthin
Chemspider ID30777172
ChEBI IDNot Available
PubChem Compound ID131752078
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM