Showing metabocard for Zeaxanthin (BMDB0002789)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:38 UTC
Update Date2020-06-04 20:38:44 UTC
MCDB ID BMDB0002789
Secondary Accession Numbers
  • BMDB02789
Metabolite Identification
Common NameZeaxanthin
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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3R,3'r)-Dihydroxy-beta,beta-caroteneChEBI
all-trans-beta-Carotene-3,3'-diolChEBI
all-trans-ZeaxanthinChEBI
AnchovyxanthinChEBI
beta,beta-Carotene-3,3'-diolChEBI
(3R,3'r)-beta,beta-Carotene-3,3'-diolKegg
(3R,3'r)-Dihydroxy-b,b-caroteneGenerator
(3R,3'r)-Dihydroxy-β,β-caroteneGenerator
all-trans-b-Carotene-3,3'-diolGenerator
all-trans-Β-carotene-3,3'-diolGenerator
b,b-Carotene-3,3'-diolGenerator
Β,β-carotene-3,3'-diolGenerator
(3R,3'r)-b,b-Carotene-3,3'-diolGenerator
(3R,3'r)-Β,β-carotene-3,3'-diolGenerator
3R,3'r ZeaxanthinMeSH
3R,3'r-ZeaxanthinMeSH
Beta Carotene 3,3' diolMeSH
ZeaxanthinsMeSH
beta-Carotene-3,3'-diolMeSH
(3R,3'r)-ZeaxanthinHMDB
all-trans-AnchovyxanthinHMDB
Xanthophyll 3HMDB
ZeaxantholHMDB
(3R,3'R)-Dihydroxy-beta-caroteneHMDB
(3R,3'R)-Dihydroxy-β-caroteneHMDB
(3R,3'R)-ZeaxanthinHMDB
(3R,3’R)-Dihydroxy-β-caroteneHMDB
(3R,3’R)-ZeaxanthinHMDB
(3R,3’R)-β,β-Carotene-3,3’-diolHMDB
all-E-ZeaxanthinHMDB
all-trans-3R,3'R-ZeaxanthinHMDB
all-trans-3R,3’R-ZeaxanthinHMDB
Chemical FormulaC40H56O2
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
IUPAC Name(1R)-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-3-en-1-ol
Traditional Namezeaxanthin
CAS Registry Number144-68-3
SMILES
C\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 Identifier
InChI=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 Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability73.47 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2000190000-2cc8481518a3532682532017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e4572017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Zeaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QIT 20V, positivesplash10-0xsi-0000490000-61514ff28dff7d7222e12020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QIT 1V, positivesplash10-0udi-0000290000-09f7ca5714961ff8f77e2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00or-0930100000-c29159f503dad4260c042020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00or-0960430000-8996d3474c2f84178dd02020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0aba-0930000000-8b9aa98251b44f2236fa2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-0930030000-987a65a5fdcee38163382020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-b50e7afd480c604277302021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-82e2fd12101c0f8a5aa32021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-376dfbe507c212fad75c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-7a03386b81c0af2daaae2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-63535133943f458f56192021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-18da3552a389eec494702021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-97b603fc0db5c5d1268c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-a5be07cc9aa560c7ad052021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-247f26afe81a420dd3292021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-a6da820e1ac88487b3542021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-a3e4a4d0d67ea298da492016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0649330000-191e0ac14dcad154b4b32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0449130000-5644e7cc2bbfa6ef09f02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8f8c6909e2b7e1022ce92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-421f46802deab60d756d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0553390000-883720ed84543eb475e22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001090000-762864ffd0f72009c6882021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0104290000-79f130816293d1629a5c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-0229210000-8aa487c6a883739666a22021-09-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00176 uM
  • International Dai...
 details
Detected and Quantified0.01 +/- 0.002 uM
  • International Dai...
 details
HMDB IDHMDB0002789
DrugBank IDDB11176
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023113
KNApSAcK IDC00000931
Chemspider ID4444421
KEGG Compound IDC06098
BioCyc IDCPD1F-130
BiGG IDNot Available
Wikipedia LinkZeaxanthin
METLIN IDNot Available
PubChem Compound5280899
PDB IDNot Available
ChEBI ID27547
References
Synthesis ReferencePaus, Joachim; Kriegl, Wolfgang. Process for the preparation of zeaxanthin and its intermediates. Eur. Pat. Appl. (1998), 19 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. M.S Havemose, Martin Riis Weisbjerg, Wender L.P Bredie, J.H Nielsen (2004). International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570. International Dairy Journal.