Lutein (YMDB01519)

Identification
YMDB IDYMDB01519
NameLutein
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLutein 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. Based on a literature review very few articles have been published on Lutein.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (3R,3'R,6'R)-Lutein
  • (3R,3'R,6S)-4,5-DIDEHYDRO-5,6-DIHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
  • (3R,3'R)-Beta,Beta-Carotene-3,3'-Diol, Lutein
  • 3,3'-Dihydroxy-alpha-carotene
  • 4,5-Didehydro-5,6-dihydro-beta,beta-carotene-3,3'-diol
  • all-trans-(+)-Xanthophyll
  • all-trans-Lutein
  • all-trans-Xanthophyll
  • beta,epsilon-Carotene-3,3'-diol
  • Carotenoid
  • Lutein
  • Lutein ester
  • Lutein, all-trans-
  • Luteine
  • Phylloxanthin
  • trans-Lutein
  • Vegetable lutein
  • Vegetable luteol
  • Xanthophyll
  • Xanthophyll, all-trans-(+ )-
  • bo-Xan
  • Lutein F
  • Lutein g
  • Lutein, gamma
  • gamma Lutein
CAS number127-40-2
WeightAverage: 568.8714
Monoisotopic: 568.428031036
InChI KeyKBPHJBAIARWVSC-JZBIMEDVSA-N
InChIInChI=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+/m1/s1
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 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
Chemical FormulaC40H56O2
SMILESO[C@@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(C)C=CC=C(C)C=C[C@H]2C(C)=CC(O)CC2(C)C)C(C)(C)C1
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
Physical Properties
StateSolid
Charge0
Melting point196 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.105 ± 0.0 µM grape juiceanaerobicBrewer's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-1000190000-79574985e26da720cbd6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3100039000-baee6b30a2822c061477JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0043490000-6587386703e49b5ed9a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gz0-0656890000-78ff1269d16692ec007aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1030-0546900000-f40ee2500358463a4322JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-7d1de7a1b619e7f7ad6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0342490000-0b5700b22b94c921a096JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02a9-0649570000-12d271b2950633507bacJSpectraViewer
References
References:
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28838
HMDB IDHMDB03233
Pubchem Compound ID6433159
Kegg IDC08601
ChemSpider ID24748311
FOODB IDFDB007276
Wikipedia IDNot Available
BioCyc IDCPD1F-119