Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:13:15 UTC |
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Update date | 2019-11-26 03:15:05 UTC |
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Primary ID | FDB017705 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Gallocatechin |
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Description | (+)-Gallocatechin, also known as gallocatechol, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety (+)-Gallocatechin is a bitter tasting compound (+)-Gallocatechin is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), green tea, and black tea and in a lower concentration in cottonseeds (Gossypium), chestnuts (Castanea), and pomegranates (Punica granatum) (+)-Gallocatechin has also been detected, but not quantified in, several different foods, such as guavas (Psidium guajava), cauliflowers (Brassica oleracea var. botrytis), yellow wax beans (Phaseolus vulgaris), custard apples (Annona reticulata), and common wheats (Triticum aestivum). This could make (+)-gallocatechin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (+)-Gallocatechin. |
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CAS Number | 970-73-0 |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C15H14O7 |
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IUPAC name | (2R,3S)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
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InChI Identifier | InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1 |
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InChI Key | XMOCLSLCDHWDHP-SWLSCSKDSA-N |
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Isomeric SMILES | O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C(O)=C1 |
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Average Molecular Weight | 306.27 |
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Monoisotopic Molecular Weight | 306.073952791 |
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Classification |
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Description | Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavans |
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Direct Parent | Epigallocatechins |
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Alternative Parents | |
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Substituents | - Epigallocatechin
- 3'-hydroxyflavonoid
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- 1-benzopyran
- Chromane
- Benzopyran
- Pyrogallol derivative
- Benzenetriol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Ether
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | 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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 58.83%; H 4.61%; O 36.57% | DFC |
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Melting Point | Mp 189-191° | 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]D +14.7 (Me2CO aq.) | 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 | Gallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-0940000000-7217377fccff4c30649e | Spectrum | Predicted GC-MS | Gallocatechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-3110049000-8b1040defcae8063c769 | Spectrum | Predicted GC-MS | Gallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Gallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-002r-0900000000-c1cd10a5867d444bd1d3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00n0-0910000000-06ff48cb1edb79736ede | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0a4i-0019000000-83d961b9674b7b1b2a65 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00p0-0941000000-47f58a4dd33c3125d051 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-0729000000-fffbd456b9b51c7d0274 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0911000000-203a6a86214265bc09e4 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00ds-2900000000-023b154fc2d731ecee10 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0219000000-db1826421845ecab1485 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05n0-0922000000-86fb5a0b2fc660815604 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-2910000000-2375ce05cd5da757763c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0019000000-b20f152234d6d77dcaa2 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0894000000-05dea610b2f972a7651e | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1930000000-7c643c8857e1259ab4fc | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0029000000-3578b95ca9c1d3f41df2 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05n0-0902000000-291e12c32e9cfe57384b | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1920000000-c1afce079042673ae394 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 58594 |
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ChEMBL ID | CHEMBL125743 |
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KEGG Compound ID | C12127 |
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Pubchem Compound ID | 65084 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 126 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB38365 |
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CRC / DFC (Dictionary of Food Compounds) ID | KZF28-J:KZF38-M |
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EAFUS ID | Not Available |
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Dr. Duke ID | GALLOCATECHOL|(+)-GALLOCATECHOL|(+)-GALLOCATECHIN|GALLOCATECHIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00035626 |
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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 | Gallocatechol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | |
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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 | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | Not Available |
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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 | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — 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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