Record Information
Version1.0
Creation date2010-04-08 22:11:52 UTC
Update date2018-05-29 01:19:09 UTC
Primary IDFDB015471
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLutein
DescriptionPigment from egg yolk and leaves. Found in all higher plants. Nutriceutical with anticancer and antioxidation props. Potentially useful for the treatment of age-related macular degeneration (AMD) of the eye Lutein is a xanthophyll and one of 600 known naturally-occurring carotenoids. The principal natural stereoisomer of lutein is (3R,3?R,6?R)-beta,epsilon-carotene-3,3?-diol.
CAS Number127-40-2
Structure
Thumb
Synonyms
SynonymSource
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diolChEBI
Bo-xanChEBI
e 161bChEBI
XanthophyllChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diolGenerator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diolGenerator
gamma LuteinMeSH
Lutein FMeSH
Lutein gMeSH
Lutein, gammaMeSH
(all-E)-Luteinbiospider
3,3'-Dihydroxy-alpha-carotenebiospider
All-trans-(+)-xanthophyllbiospider
All-trans-luteinbiospider
b,e-Carotene-3,3'-dioldb_source
beta,epsilon-Carotene-3,3'-diolbiospider
beta,epsilon-Carotene-3,3'-diol, (3R,3'R,6'R)-biospider
Lutein esterHMDB
Lutein, all-trans-biospider
LuteineHMDB
Trans-luteinbiospider
Vegetable luteinHMDB
Vegetable luteolHMDB
Xanthophyll, all-trans-(+)-biospider
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
Polarizability74.26 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O2
IUPAC name(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-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+/t35-,36+,37-/m0/s1
InChI KeyKBPHJBAIARWVSC-RGZFRNHPSA-N
Isomeric 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
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
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 Descriptors
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 196°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18643.9 +160 (CHCl3)DFC
Spectroscopic UV Data472 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID4938343
ChEMBL IDNot Available
KEGG Compound IDC08601
Pubchem Compound ID6433159
Pubchem Substance IDNot Available
ChEBI ID28838
Phenol-Explorer IDNot Available
DrugBank IDDB00137
HMDB IDHMDB03233
CRC / DFC (Dictionary of Food Compounds) IDKCN64-A:KCN64-A
EAFUS ID3880
Dr. Duke IDXANTHOPHYLL|LUTEIN
BIGG IDNot Available
KNApSAcK IDC00003776
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLutein
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti maculiticDUKE
anti nyctalopicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti proliferantDUKE
anti radicularDUKE
anti retiniticDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
bruchifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
colorant37958 DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prooxidantDUKE
quinone-reductase inducerDUKE
retinoprotectantDUKE
ubiquiotDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.