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 03:15:04 UTC |
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Primary ID | FDB017700 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Epigallocatechin |
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Description | (-)-Epigallocatechin, also known as epigallocatechol or antiscurvy factor C2, 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 (-)-Epigallocatechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (-)-Epigallocatechin is a bitter tasting compound (-)-Epigallocatechin is found, on average, in the highest concentration within a few different foods, such as cocoa beans, tea, and prunus (cherry, plum) and in a lower concentration in common grapes, sweet cherries, and almonds (-)-Epigallocatechin has also been detected, but not quantified in, several different foods, such as figs, blackcurrants, rices, sweet bay, and cauliflowers. This could make (-)-epigallocatechin a potential biomarker for the consumption of these foods. |
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CAS Number | 970-74-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-3,3',4',5,5',7-Flavanhexol | ChEBI | (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol | ChEBI | 2,3-cis-Epigallocatechin | ChEBI | Epigallocatechol | ChEBI | l-Epigallocatechin | ChEBI | (-)-cis-3,3',4',5,5',7-Hexahydroxyflavan | HMDB | (-)-cis-3,3',4',5,5',7-Hexahydroxyflavane | HMDB | (-)-Epigallocatechol | HMDB | Antiscurvy factor C2 | HMDB | EGC | HMDB | Epigallocatechin | HMDB, MeSH | l-Epigallocatechol | HMDB | Gallocatechol, (2R-trans)-isomer | MeSH, HMDB | Gallocatechol | MeSH, HMDB | Gallocatechol, (2R-cis)-isomer | MeSH, HMDB | Gallocatechin | MeSH, HMDB | (-)-3,3’,4’,5,5’,7-Flavanhexol | HMDB | (-)-Epigallocatechin | HMDB | (-)-epi-Gallocatechin | HMDB | (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychroman | HMDB | (2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol | HMDB | 1-epi-3',4',5',5,7-Pentahydroxy-3-flavanol | HMDB | 1-epi-3’,4’,5’,5,7-Pentahydroxy-3-flavanol | HMDB | 3,3',4',5,5',7-Flavanhexol | HMDB | 3,3’,4’,5,5’,7-Flavanhexol | HMDB | Galloepicatechin | HMDB | epi-Gallocatechin | HMDB | 3,3',4',5,5',7-Hexahydroxyflavan; (-)-cis-form | db_source | L-Epigallocatechin | biospider | L-Epigallocatechol | biospider |
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Predicted Properties | |
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Chemical Formula | C15H14O7 |
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IUPAC name | (2R,3R)-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-/m1/s1 |
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InChI Key | XMOCLSLCDHWDHP-IUODEOHRSA-N |
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Isomeric SMILES | O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O |
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Average Molecular Weight | 306.2675 |
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Monoisotopic Molecular Weight | 306.073952802 |
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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 | Industrial application: Biological role: |
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Foods | Cocoa and cocoa products Nuts and legumes: Fruits and vegetables: Beverages: |
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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 | 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 219-221° dec. | 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 -60.3 (c, 0.3 in EtOH) | 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 | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0978700000-567c7251027c80e91a01 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0978700000-567c7251027c80e91a01 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-0940000000-a9630fe8d1a042f59c2a | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-0udi-3110049000-8b1040defcae8063c769 | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0pb9-0019003000-c4d2b02a82d1cf14714e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0pb9-0019003000-c4d2b02a82d1cf14714e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-002r-0910000000-8dfe0ba4e2ec1225213f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0pb9-0019003000-c4d2b02a82d1cf14714e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-00p0-0951000000-95142c4b42b35c4bdac9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-000i-0900000000-4e9ebbe814af2f8c284d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Negative | splash10-05r0-0913000000-be7d3c4d9b40f51414e7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0529000000-0036b0386a7ade78fcac | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00vi-0690000000-702c5a1e065692895b3a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00vi-0690000000-7844ed1a917693a67b37 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-002r-0910000000-8dfe0ba4e2ec1225213f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00p0-0951000000-95142c4b42b35c4bdac9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0900000000-c79003b472daf421e492 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000i-0910000000-f92cf1606a46a5b16f4f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000i-0910000000-2026f33ac95d368b5268 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-0729000000-fffbd456b9b51c7d0274 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0911000000-203a6a86214265bc09e4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00ds-2900000000-023b154fc2d731ecee10 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0219000000-db1826421845ecab1485 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05n0-0922000000-86fb5a0b2fc660815604 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-2910000000-2375ce05cd5da757763c | JSpectraViewer |
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External Links |
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ChemSpider ID | 65231 |
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ChEMBL ID | CHEMBL47386 |
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KEGG Compound ID | C12136 |
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Pubchem Compound ID | 72277 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 42255 |
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Phenol-Explorer ID | 127 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB38361 |
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CRC / DFC (Dictionary of Food Compounds) ID | KZF28-J:KZF29-K |
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EAFUS ID | Not Available |
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Dr. Duke ID | EPIGALLOCATECHOL|(-)-EPI-GALLO-CATECHOL|(-)-EPIGALLOCATECHIN|EPIGALLOCATECHIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00008818 |
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HET ID | EGT |
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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 | Not Available |
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Phenol-Explorer Metabolite ID | 127 |
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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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angiotensin converting enzyme inhibitor | 35457 | An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). | DUKE | aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | anti acne | 50177 | A drug used to treat or prevent skin disorders or for the routine care of skin. | DUKE | anti amebic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti carcinogenic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti caries | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti giardial | | | DUKE | anti mutagenic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti radicular | | | DUKE | anti streptococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | beta-adrenergic receptor blocker | 37962 | Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter. | DUKE | catechol O-methyltransferase inhibitor | 48406 | An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6). | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | neuroprotective | 63726 | Any compound that can be used for the treatment of neurodegenerative disorders. | DUKE | peroxynitrite scavenger | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | protisticide | | | DUKE | xanthine oxidase inhibitor | 35634 | An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2). | DUKE |
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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. — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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