Zeaxanthin (CHEM019267)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:58:07 UTC
Update Date2016-11-09 01:15:57 UTC
Accession NumberCHEM019267
Identification
Common NameZeaxanthin
ClassSmall Molecule
DescriptionZeaxanthin 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. Zeaxanthin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Zeaxanthin exists in all living organisms, ranging from bacteria to humans.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2000190000-2cc8481518a353268253Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0211190000-6cb18e6d42002a2d6718Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0928330000-886cfc527b85b399d1ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2349120000-9d5fa2a6cc5c98c2dfa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-cbb0d37d0ab268305e5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-c36bec0a178ebda0a233Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0353390000-369de129def79fa1c692Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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