XANTHOPHYLL (CHEM007850)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:30:57 UTC
Update Date2016-10-28 10:02:51 UTC
Accession NumberCHEM007850
Identification
Common NameXANTHOPHYLL
ClassSmall Molecule
DescriptionLutein is a xanthophyll carotenoid abundant in green leafy vegetables such as spinach and kale, but also found in other organisms. Lutein is used as an antioxidant and for blue light absorption. [Biocyc PWY-5947]
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,3'-Dihydroxy-alpha-caroteneHMDB
all-trans-(+)-XanthophyllHMDB
all-trans-LuteinHMDB
beta,epsilon-Carotene-3,3'-diolHMDB
bo-XanHMDB
Lutein esterHMDB
LuteineHMDB
trans-LuteinHMDB
Vegetable luteinHMDB
Vegetable luteolHMDB
Lutein FMeSH, HMDB
Lutein gMeSH, HMDB
Lutein, gammaMeSH, HMDB
gamma LuteinMeSH, HMDB
Chemical FormulaC40H56O2
Average Molecular Mass568.886 g/mol
Monoisotopic Mass568.428 g/mol
CAS Registry Number127-40-2
IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
Traditional Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
SMILESC\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C
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+/t35-,36+,37-/m0/s1
InChI KeyKBPHJBAIARWVSC-RGZFRNHPSA-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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.00073 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
Polarizability73.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-1000190000-79574985e26da720cbd6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3100039000-baee6b30a2822c061477Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-56a7b3ad9850d88a093aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0729640000-fa9f79f8a73fa60b8abfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2439510000-8c70ee5c9af7440a4672Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-e64043a148b331ba05a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-a48901fc52e8e64be250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0522590000-ed879e2e3d350ac0e502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0043490000-6587386703e49b5ed9a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gz0-0656890000-78ff1269d16692ec007aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1030-0546900000-f40ee2500358463a4322Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-7d1de7a1b619e7f7ad6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0342490000-0b5700b22b94c921a096Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02a9-0649570000-12d271b2950633507bacSpectrum
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 IDHMDB0303013
FooDB IDFDB007276
Phenol Explorer IDNot Available
KNApSAcK IDC00003774
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4938343
ChEBI IDNot Available
PubChem Compound ID6433159
Kegg Compound IDNot Available
YMDB IDYMDB01519
ECMDB IDM2MDB005297
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available