Record Information
Version1.0
Creation date2010-04-08 22:14:38 UTC
Update date2018-05-29 01:43:38 UTC
Primary IDFDB019865
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3R,3'R, all-E)-Zeaxanthin
DescriptionConstituent of crustaceans, fish, barley, maize (Zea mays), tomatoes, paprika pods, hen egg yolk, fruits and numerous green vegetables. Potential nutriceutical for treatment of age-related macular degeneration of the eye (AMD) [DFC] Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye. Within the central macula, zeaxanthin is the dominant component, whereas in the peripheral retina, lutein predominates. The principal natural form of zeaxanthin is (3R,3'R)-zeaxanthin. As a food additive, zeaxanthin is a food dye with E number E161h. [Wikipedia]. (3R,3'R, all-E)-Zeaxanthin is found in many foods, some of which are green vegetables, cottonseed, tamarind, and common beet.
CAS Number144-68-3
Structure
Thumb
Synonyms
SynonymSource
(3S,3's)-ZeaxanthinHMDB
(3S,3'S)-beta,beta-Carotene-3,3'-diolHMDB
(3S,3'S)-β,β-Carotene-3,3'-diolHMDB
(3S,3'S,all-E)-ZeaxanthinHMDB
(3S,3’S)-ZeaxanthinHMDB
(3S,3’S)-β,β-Carotene-3,3’-diolHMDB
(3S,3’S,all-E)-ZeaxanthinHMDB
(3R,3'R)-beta,beta-carotene-3,3'-diolbiospider
(3R,3'R)-dihydroxy-b,b-caroteneGenerator
(3R,3'R)-dihydroxy-beta,beta-caroteneChEBI
(3R,3'R)-dihydroxy-β,β-caroteneGenerator
(3R,3'R)-Zeaxanthinbiospider
3R,3'R-Zeaxanthinbiospider
all-trans-AnchovyxanthinHMDB
all-trans-b-Carotene-3,3'-diolGenerator
all-trans-beta-Carotene-3,3'-diolChEBI
all-trans-ZeaxanthinHMDB
all-trans-β-carotene-3,3'-diolGenerator
AnchovyxanthinChEBI
Xanthophyll 3HMDB
ZeaxanthinChEBI
β,β-carotene-3,3'-diolGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP8.3ALOGPS
logP8.35ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity194.95 m³·mol⁻¹ChemAxon
Polarizability73.76 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O2
IUPAC name(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-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-3-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/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m0/s1
InChI KeyJKQXZKUSFCKOGQ-ANDPMPNWSA-N
Isomeric SMILESO[C@H]1CC(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C2=C(C)C[C@H](O)CC2(C)C)C(C)(C)C1
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
Classification
DescriptionThis compound 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
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
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 215.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20656.3 -44 (c, 0.2 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1000090000-5a745596c3e750ed2edfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0211190000-6cb18e6d42002a2d6718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0928330000-e7a615b9bbf109db7c31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2349220000-b00e41420925c8709737View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-cbb0d37d0ab268305e5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-c36bec0a178ebda0a233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0353390000-369de129def79fa1c692View in MoNA
ChemSpider ID4444421
ChEMBL IDCHEMBL2359248
KEGG Compound IDC06098
Pubchem Compound ID5280899
Pubchem Substance IDNot Available
ChEBI ID27547
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02789
CRC / DFC (Dictionary of Food Compounds) IDJVG59-L:MDP33-D
EAFUS IDNot Available
Dr. Duke IDTRANS-ZEAXANTHIN|ZEAXANTHIN|BETA-BETA-CAROTENE-3-DIOL
BIGG IDNot Available
KNApSAcK IDC00000931
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDZeaxanthin
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 cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
colorant37958 DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
quinone-reductase inducerDUKE
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.CHEBI
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.