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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:06:32 UTC
Update Date2021-10-13 06:59:59 UTC
HMDB IDHMDB0036922
Secondary Accession Numbers
  • HMDB36922
Metabolite Identification
Common NameIsozeaxanthin
DescriptionIsozeaxanthin 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. Based on a literature review a small amount of articles have been published on Isozeaxanthin.
Structure
Data?1563862950
Synonyms
ValueSource
4,4'-dihydro-β,β-caroteneMetaCyc, HMDB
AphanicolHMDB
b,b-Carotene-4,4'-diolHMDB
beta,beta-Carotene-4,4'-diolHMDB
Lactam-based compound, 12DHMDB
Chemical FormulaC40H56O2
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
IUPAC Name3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-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]-2,4,4-trimethylcyclohex-2-en-1-ol
Traditional Name3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-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]-2,4,4-trimethylcyclohex-2-en-1-ol
CAS Registry Number29065-03-0
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)CCC1(C)C
InChI Identifier
InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24,37-38,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
InChI KeyGYZWNQLEQAGWGD-DKLMTRRASA-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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point149 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.4e-11 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00058 g/LALOGPS
logP10(8.49) g/LALOGPS
logP10(8.66) g/LChemAxon
logS10(-6) g/LALOGPS
pKa (Strongest Acidic)18.18ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity194.64 m³·mol⁻¹ChemAxon
Polarizability73.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+248.66431661259
DarkChem[M-H]-247.66631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsozeaxanthinC\C(\C=C\C=C(/C)\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)CCC1(C)C5966.8Standard polar33892256
IsozeaxanthinC\C(\C=C\C=C(/C)\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)CCC1(C)C4736.4Standard non polar33892256
IsozeaxanthinC\C(\C=C\C=C(/C)\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(O)CCC1(C)C4529.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isozeaxanthin,1TMS,isomer #1CC1=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(O[Si](C)(C)C)CCC2(C)C)C(C)(C)CCC1O4758.8Semi standard non polar33892256
Isozeaxanthin,2TMS,isomer #1CC1=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(O[Si](C)(C)C)CCC2(C)C)C(C)(C)CCC1O[Si](C)(C)C4678.4Semi standard non polar33892256
Isozeaxanthin,1TBDMS,isomer #1CC1=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(O[Si](C)(C)C(C)(C)C)CCC2(C)C)C(C)(C)CCC1O4952.0Semi standard non polar33892256
Isozeaxanthin,2TBDMS,isomer #1CC1=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(O[Si](C)(C)C(C)(C)C)CCC2(C)C)C(C)(C)CCC1O[Si](C)(C)C(C)(C)C5096.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isozeaxanthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4000290000-a06883676cc3229803812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isozeaxanthin GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3000029000-d5662ace8fb2f3ea93d52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isozeaxanthin GC-MS ("Isozeaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isozeaxanthin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isozeaxanthin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isozeaxanthin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 10V, Positive-QTOFsplash10-0gb9-0201190000-2d877b1f52da6c82a5bd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 20V, Positive-QTOFsplash10-0f6t-0829340000-065db8adb78e5fdc3a212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 40V, Positive-QTOFsplash10-000b-2449510000-1c8371e2e130642d11c12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 10V, Negative-QTOFsplash10-014i-0000090000-f28ac43a9d6323d163bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 20V, Negative-QTOFsplash10-014i-0000090000-47cda22692eb4df312b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 40V, Negative-QTOFsplash10-0uxr-1564390000-86af17eebdaf09723d362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 10V, Positive-QTOFsplash10-0f89-0000290000-9642ab729cc1304f23272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 20V, Positive-QTOFsplash10-01q9-0619730000-7e345380682f80d0a0342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 40V, Positive-QTOFsplash10-0gdr-0117900000-016e16b1853a073effa02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 10V, Negative-QTOFsplash10-014i-0000090000-21cb07adfb565b5450462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 20V, Negative-QTOFsplash10-014i-0103390000-659b6eb33a0a11c4b44c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isozeaxanthin 40V, Negative-QTOFsplash10-0fca-0119330000-5c7a750b9c93ac4ad4762021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015889
KNApSAcK IDC00022868
Chemspider ID9932404
KEGG Compound IDNot Available
BioCyc IDCPD-7853
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11757703
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1858151
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.