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 |
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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 | Descriptor | ID | Definition | Reference |
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Anti-cancer | 35610 | An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Colorant | 37958 | A substance that imparts color, with no inherent biological role. Therapeutically, colorants are used to enhance visual appeal and identification of medications. Medically, they are used in diagnostic imaging, such as contrast agents, and in ophthalmic applications to aid in vision correction and protection. | DUKE | Hepatoprotective | 62868 | An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities. | DUKE | Quinone-reductase inducer | | An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | CHEBI |
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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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