Record Information
Version1.0
Creation date2010-04-08 22:13:48 UTC
Update date2018-05-29 01:37:36 UTC
Primary IDFDB018591
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCalthaxanthin
DescriptionIsolated from plants and animals (e.g. Potamon dehaari, Yellowtail Fish) (3R,3'S,6'R)-Carotene-3,3'-diol 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)
CAS Number52842-48-5
Structure
Thumb
Synonyms
SynonymSource
(3R,3'r)-beta,beta-Carotene-3,3'-diol, luteinHMDB
(3R,3'r,6'r)-LuteinHMDB
(3R,3'r,6S)-4,5-didehydro-5,6-dihydro-beta,beta-Carotene-3,3'-diolHMDB
4,5-didehydro-5,6-dihydro-beta,beta-Carotene-3,3'-diolHMDB
all-trans-(+)-XanthophyllHMDB
all-trans-LuteinHMDB
all-trans-XanthophyllHMDB
beta,epsilon-Carotene-3,3'-diolHMDB
LuteinHMDB
Lutein esterHMDB
LuteineHMDB
PhylloxanthinHMDB
trans-LuteinHMDB
Vegetable luteinHMDB
Vegetable luteolHMDB
Lutein FMeSH
Lutein gMeSH
Lutein, gammaMeSH
gamma LuteinMeSH
(3R,3'S,6'R)-beta,epsilon-Carotene-3,3'-diolmanual
3'-Epiluteindb_source
Calthaxanthindb_source
Lutein Bmanual
Predicted Properties
PropertyValueSource
Water Solubility0.00073 g/LALOGPS
logP8.29ALOGPS
logP8.55ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.06 m³·mol⁻¹ChemAxon
Polarizability72.79 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O2
IUPAC name4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol
InChI IdentifierInChI=1S/C40H56O2/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/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
InChI KeyKBPHJBAIARWVSC-DKLMTRRASA-N
Isomeric SMILESC\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/C1=C(C)CC(O)CC1(C)C
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
Classification
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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.45%; H 9.92%; O 5.62%DFC
Melting PointMp 162-163°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +88 (EtOH)DFC
Spectroscopic UV Data472 () (no solvent reported)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3100190000-5e12a00cf3eb938ca3ddJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2000049000-9b0de00895c35dcdc2d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-56a7b3ad9850d88a093aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0729640000-fa9f79f8a73fa60b8abfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2439510000-8c70ee5c9af7440a4672JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-e64043a148b331ba05a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-a48901fc52e8e64be250JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0522590000-ed879e2e3d350ac0e502JSpectraViewer
ChemSpider ID17220873
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID16061195
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03415
CRC / DFC (Dictionary of Food Compounds) IDKCN64-A:LLS65-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00022872
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference