Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:14:38 UTC |
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Update date | 2019-11-26 03:17:57 UTC |
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Primary ID | FDB019865 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (3R,3'R, all-E)-Zeaxanthin |
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Description | Constituent of crustaceans, fish, barley, maize (Zea mays), tomatoes, paprika pods, hen egg yolk, fruits and numerous green vegetables. Potential nutriceutical for treatment of age-related macular degeneration of the eye (AMD) [DFC]
Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye. Within the central macula, zeaxanthin is the dominant component, whereas in the peripheral retina, lutein predominates. The principal natural form of zeaxanthin is (3R,3'R)-zeaxanthin. As a food additive, zeaxanthin is a food dye with E number E161h. [Wikipedia]. (3R,3'R, all-E)-Zeaxanthin is found in many foods, some of which are green vegetables, cottonseed, tamarind, and common beet. |
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CAS Number | 144-68-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(3S,3's)-b,b-Carotene-3,3'-diol | Generator | (3S,3's)-Β,β-carotene-3,3'-diol | Generator | (3S,3's)-Zeaxanthin | HMDB | (3S,3'S)-Zeaxanthin | HMDB | (3S,3'S)-beta,beta-Carotene-3,3'-diol | HMDB | (3S,3'S,all-E)-Zeaxanthin | HMDB | (3S,3’S)-Zeaxanthin | HMDB | (3S,3’S)-β,β-Carotene-3,3’-diol | HMDB | (3S,3’S,all-E)-Zeaxanthin | HMDB | (3R,3'R)-beta,beta-carotene-3,3'-diol | biospider | (3R,3'R)-dihydroxy-b,b-carotene | Generator | (3R,3'R)-dihydroxy-beta,beta-carotene | ChEBI | (3R,3'R)-dihydroxy-β,β-carotene | Generator | (3R,3'R)-Zeaxanthin | biospider | 3R,3'R-Zeaxanthin | biospider | all-trans-Anchovyxanthin | HMDB | all-trans-b-Carotene-3,3'-diol | Generator | all-trans-beta-Carotene-3,3'-diol | ChEBI | all-trans-Zeaxanthin | HMDB | all-trans-β-carotene-3,3'-diol | Generator | Anchovyxanthin | ChEBI | Xanthophyll 3 | HMDB | Zeaxanthin | ChEBI | β,β-carotene-3,3'-diol | Generator |
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Predicted Properties | |
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Chemical Formula | C40H56O2 |
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IUPAC name | (1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-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 |
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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-/m0/s1 |
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InChI Key | JKQXZKUSFCKOGQ-ANDPMPNWSA-N |
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Isomeric SMILES | O[C@H]1CC(C)=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[C@H](O)CC2(C)C)C(C)(C)C1 |
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Average Molecular Weight | 568.8714 |
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Monoisotopic Molecular Weight | 568.428031036 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Tetraterpenoids |
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Direct Parent | Xanthophylls |
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Alternative Parents | |
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Substituents | - Xanthophyll
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 84.45%; H 9.92%; O 5.62% | DFC |
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Melting Point | Mp 215.5° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]20656.3 -44 (c, 0.2 in CHCl3) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | (3R,3'R, all-E)-Zeaxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-1000090000-5a745596c3e750ed2edf | Spectrum | Predicted GC-MS | (3R,3'R, all-E)-Zeaxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-3000049000-45b1b78e4b208f89e457 | Spectrum | Predicted GC-MS | (3R,3'R, all-E)-Zeaxanthin, "(3S,3'S)-beta,beta-Carotene-3,3'-diol,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (3R,3'R, all-E)-Zeaxanthin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (3R,3'R, all-E)-Zeaxanthin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (3R,3'R, all-E)-Zeaxanthin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gb9-0211190000-6cb18e6d42002a2d6718 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0928330000-e7a615b9bbf109db7c31 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kb-2349220000-b00e41420925c8709737 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000090000-cbb0d37d0ab268305e5e | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0000090000-c36bec0a178ebda0a233 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uxr-0353390000-369de129def79fa1c692 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0001090000-762864ffd0f72009c688 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0104290000-79f130816293d1629a5c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003b-0229210000-8aa487c6a883739666a2 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0132890000-50be05fa861115532d66 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-0215950000-140f155070c122eab02c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0v00-0039600000-2725b4335e7d4d6e49c2 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4444421 |
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ChEMBL ID | CHEMBL2359248 |
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KEGG Compound ID | C06098 |
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Pubchem Compound ID | 5280899 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 27547 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB02789 |
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CRC / DFC (Dictionary of Food Compounds) ID | JVG59-L:MDP33-D |
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EAFUS ID | Not Available |
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Dr. Duke ID | TRANS-ZEAXANTHIN|ZEAXANTHIN|BETA-BETA-CAROTENE-3-DIOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000931 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Zeaxanthin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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