Zeaxanthin (CED0002449)

Record Information
Version1.0
Creation Date2016-05-22 05:58:07 UTC
Update Date2026-05-14 19:07:36 UTC
Accession NumberCHEM019267
Identification
Common NameZeaxanthin
ClassSmall Molecule
Description
Zeaxanthin (C40H56O2) belongs to the tetraterpenoids, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 568.89 g/mol, Zeaxanthin is a heavy molecule. This compound serves as an industrial and biological antioxidant (PMC12157995) and is utilized industrially as a food additive (PMC13340296). Zeaxanthin is found in five recorded sources, including electrical and electronic equipment such as video games, as well as food, food processing, and cookware, specifically in the processing of fish and the preparation of malt, vinegar, and wine or sparkling wine. Regarding health effects, Zeaxanthin is associated with a decrease in cases of obesity (PMC12732708) and breast cancer (PMC10220911), though it is associated with an increase in atherosclerosis (PMC4626686). It has been observed to decrease in the blood of individuals with diabetes mellitus (PMC5793074). Furthermore, the compound exhibits therapeutic effects on lung cancer (PMC11729017) and diabetic retinopathy (PMC5793074).
Contaminant TypeNot Available
Chemical Structure
SynonymsNot Available
Chemical FormulaC40H56O2
Average Molecular Mass568.886 g/mol
Monoisotopic Mass568.428 g/mol
CAS Registry Number144-68-3
IUPAC Name(1R)-4-[(1E,3E,5E,7Z,9Z,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-3-en-1-ol
Traditional Name(1R)-4-[(1E,3E,5E,7Z,9Z,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-3-en-1-ol
SMILESC\C(\C=C\C=C(/C)\C=C\C1=C(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/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
InChI KeyJKQXZKUSFCKOGQ-QAYBQHTQSA-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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability72.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udi-2000190000-2cc8481518a353268253Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-3000049000-45b1b78e4b208f89e457Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0xsi-0000490000-61514ff28dff7d7222e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000290000-09f7ca5714961ff8f77eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0930100000-c29159f503dad4260c04Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0960430000-8996d3474c2f84178dd0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aba-0930000000-8b9aa98251b44f2236faNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0930030000-987a65a5fdcee3816338Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aba-0930000000-b50e7afd480c60427730Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0950320000-82e2fd12101c0f8a5aa3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0950420000-376dfbe507c212fad75cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0930030000-7a03386b81c0af2daaaeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aba-0930000000-63535133943f458f5619Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0930030000-18da3552a389eec49470Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0950420000-97b603fc0db5c5d1268cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aba-0930000000-a5be07cc9aa560c7ad05Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aba-0930000000-247f26afe81a420dd329Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0950320000-a6da820e1ac88487b354Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gb9-0111190000-a3e4a4d0d67ea298da49Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0frt-0649330000-191e0ac14dcad154b4b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000b-0449130000-5644e7cc2bbfa6ef09f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000090000-8f8c6909e2b7e1022ce9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000090000-421f46802deab60d756dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxr-0553390000-883720ed84543eb475e2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0001090000-762864ffd0f72009c688Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0104290000-79f130816293d1629a5cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003b-0229210000-8aa487c6a883739666a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0132890000-50be05fa861115532d66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0215950000-140f155070c122eab02cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0v00-0039600000-2725b4335e7d4d6e49c2Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
8797.0Log mg/kg[4900:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
lung cancerhas_therapeutic_effect_onNot AvailablePMC11729017
breast cancerassociated_withdecreasePMC10220911
diabetes mellitusdecreased_in_blood_indecreasePMC5793074
obesityassociated_withdecreasePMC12732708
atherosclerosisassociated_withincreasePMC4626686
diabetic retinopathyhas_therapeutic_effect_onNot AvailablePMC5793074
macular degenerationassociated_withNot AvailablePMC3269679
Exposure Sources
Source IDSourceSectorReference
539Video GamesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
597ChemosterilantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAldehyde dehydrogenase 1A1P27463Gallus gallusPredicted (SEA)0.155698
Click to view 3D structureRetinoic acid receptor alphaP11416Mus musculusPredicted (SEA)0.544945
Click to view 3D structureRetinoic acid receptor gammaP18911Mus musculusPredicted (SEA)0.467095
Click to view 3D structureRetinoic acid receptor betaP22605Mus musculusPredicted (SEA)0.622794
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)8.79696
Retinoic acid receptor gamma structureClick to view 3D structureRetinoic acid receptor gammaP13631HumansPredicted (SEA)5.91654
Prosaposin structureClick to view 3D structureProsaposinP07602HumansPredicted (SEA)0.311397
Click to view 3D structureRetinoic acid receptor RXR-alphaP28700Mus musculusPredicted (SEA)1.86838
Click to view 3D structureCellular retinoic acid-binding protein 1P62965Mus musculusPredicted (SEA)0.467095
Click to view 3D structureCellular retinoic acid-binding protein 2P22935Mus musculusPredicted (SEA)0.467095
Click to view 3D structureBeta-lactoglobulinP02754Bos taurusPredicted (SEA)0.311397
Retinoic acid receptor beta structureClick to view 3D structureRetinoic acid receptor betaP10826HumansPredicted (SEA)4.9045
Retinoic acid receptor alpha structureClick to view 3D structureRetinoic acid receptor alphaP10276HumansPredicted (SEA)9.41976
Click to view 3D structureCellular retinoic acid-binding protein 1P40220Gallus gallusPredicted (SEA)0.389246
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)38.6132
Retinoic acid receptor RXR-gamma structureClick to view 3D structureRetinoic acid receptor RXR-gammaP48443HumansPredicted (SEA)3.50322
Retinoic acid receptor RXR-beta structureClick to view 3D structureRetinoic acid receptor RXR-betaP28702HumansPredicted (SEA)4.04816
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)3.89246
Click to view 3D structureRetinoic acid receptor RXR-gammaP28705Mus musculusPredicted (SEA)4.67095
Click to view 3D structureRetinoic acid receptor RXR-betaP28704Mus musculusPredicted (SEA)5.3716
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)57.1413
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)784.02
Click to view 3D structureSphingolipid delta(4)-desaturase DES1Q5XIF5Rattus norvegicusPredicted (SEA)0.311397
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)428.093
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)1434.22
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZeaxanthin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477766
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDM2MDB005230
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Paus, Joachim; Kriegl, Wolfgang. Process for the preparation of zeaxanthin and its intermediates. Eur. Pat. Appl. (1998), 19 pp.
2. International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570