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(3R,3'R, all-E)-Zeaxanthin (FDB019865)

Record Information
Version1.0
Creation date2010-04-08 22:14:38 UTC
Update date2019-11-26 03:17:57 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(3R,3'R, all-E)-Zeaxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1000090000-5a745596c3e750ed2edfSpectrum
Predicted GC-MS(3R,3'R, all-E)-Zeaxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457Spectrum
Predicted GC-MS(3R,3'R, all-E)-Zeaxanthin, "(3S,3'S)-beta,beta-Carotene-3,3'-diol,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3R,3'R, all-E)-Zeaxanthin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3R,3'R, all-E)-Zeaxanthin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3R,3'R, all-E)-Zeaxanthin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0211190000-6cb18e6d42002a2d67182017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0928330000-e7a615b9bbf109db7c312017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2349220000-b00e41420925c87097372017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-cbb0d37d0ab268305e5e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-c36bec0a178ebda0a2332017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0353390000-369de129def79fa1c6922017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001090000-762864ffd0f72009c6882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0104290000-79f130816293d1629a5c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-0229210000-8aa487c6a883739666a22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0132890000-50be05fa861115532d662021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0215950000-140f155070c122eab02c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-0039600000-2725b4335e7d4d6e49c22021-09-24View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH 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— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— 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.