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Record Information
Version2.0
Created at2022-09-04 13:46:41 UTC
Updated at2022-09-04 13:46:42 UTC
NP-MRD IDNP0195838
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r)-4-[(1z,3z,5z,7z,9z,11z,13z,15z,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
DescriptionCis-Zeaxanthin 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. (1r)-4-[(1z,3z,5z,7z,9z,11z,13z,15z,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 was first documented in 2006 (PMID: 16571067). Based on a literature review a significant number of articles have been published on cis-Zeaxanthin (PMID: 34507741) (PMID: 20734986) (PMID: 19126445) (PMID: 17927948) (PMID: 17227674).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H56O2
Average Mass568.8860 Da
Monoisotopic Mass568.42803 Da
IUPAC Name(1R)-4-[(1Z,3Z,5Z,7Z,9Z,11Z,13Z,15Z,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-[(1Z,3Z,5Z,7Z,9Z,11Z,13Z,15Z,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
CAS Registry NumberNot Available
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-XDWPESMJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.35ChemAxon
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
Polarizability71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102008443
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Fernandes AS, Nascimento TC, Pinheiro PN, Vendruscolo RG, Wagner R, de Rosso VV, Jacob-Lopes E, Zepka LQ: Bioaccessibility of microalgae-based carotenoids and their association with the lipid matrix. Food Res Int. 2021 Oct;148:110596. doi: 10.1016/j.foodres.2021.110596. Epub 2021 Jul 10. [PubMed:34507741 ]
  2. Abdel-Aal el-SM, Young JC, Akhtar H, Rabalski I: Stability of lutein in wholegrain bakery products naturally high in lutein or fortified with free lutein. J Agric Food Chem. 2010 Sep 22;58(18):10109-17. doi: 10.1021/jf102400t. [PubMed:20734986 ]
  3. Widomska J, Kostecka-Gugala A, Latowski D, Gruszecki WI, Strzalka K: Calorimetric studies of the effect of cis-carotenoids on the thermotropic phase behavior of phosphatidylcholine bilayers. Biophys Chem. 2009 Mar;140(1-3):108-14. doi: 10.1016/j.bpc.2008.12.002. Epub 2008 Dec 24. [PubMed:19126445 ]
  4. Widomska J, Subczynski WK: Transmembrane localization of cis-isomers of zeaxanthin in the host dimyristoylphosphatidylcholine bilayer membrane. Biochim Biophys Acta. 2008 Jan;1778(1):10-9. doi: 10.1016/j.bbamem.2007.08.021. Epub 2007 Sep 6. [PubMed:17927948 ]
  5. Wang Y, Connor SL, Wang W, Johnson EJ, Connor WE: The selective retention of lutein, meso-zeaxanthin and zeaxanthin in the retina of chicks fed a xanthophyll-free diet. Exp Eye Res. 2007 Mar;84(3):591-8. doi: 10.1016/j.exer.2006.11.013. Epub 2007 Jan 16. [PubMed:17227674 ]
  6. Dreuw A: Influence of geometry relaxation on the energies of the S1 and S2 states of violaxanthin, zeaxanthin, and lutein. J Phys Chem A. 2006 Apr 6;110(13):4592-9. doi: 10.1021/jp057385y. [PubMed:16571067 ]
  7. LOTUS database [Link]