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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2019-07-23 05:45:22 UTC
HMDB IDHMDB0002193
Secondary Accession Numbers
  • HMDB02193
Metabolite Identification
Common NameE,e-Carotene-3,3'-dione
DescriptionCarotene-3,3'-dione is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048 , 15003396 ).
Structure
Data?1563860722
SynonymsNot Available
Chemical FormulaC40H52O2
Average Molecular Weight564.8397
Monoisotopic Molecular Weight564.396730908
IUPAC Name3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one
Traditional Namee,e-carotene-3,3'-dione
CAS Registry Number28840-14-4
SMILES
C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC(=O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1C(C)=CC(=O)CC1(C)C
InChI Identifier
InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-26,37-38H,27-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
InChI KeyIMFOMPZKWQBDLQ-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.0005 g/LALOGPS
logP8.49ALOGPS
logP9.57ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity193.38 m³·mol⁻¹ChemAxon
Polarizability71.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9313370000-589e472f03c0920eb503Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0222390000-6ae994395029f382f398Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0586930000-2a209a7e354b1a6d24caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1376910000-fade15ac03834455d1ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-1319b532b991390aac3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000090000-3f76a4a1a487715d7f82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0222590000-a4c220a5309e1cb6372bSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)FemaleNormal details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015932
KNApSAcK IDNot Available
Chemspider ID4581802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5471691
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSliwka, Hans-Richard; Liaaen-Jensen, Synnove. Selenium carotenoids. 2 Synthesis of e,e-carotene-3,3'-dione from rhodoxanthin. Acta Chemica Scandinavica (1995), 49(11), 856-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. [PubMed:1416048 ]
  2. Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. [PubMed:15003396 ]