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, 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 bitter tasting compound (-)-Epigallocatechin is found, on average, in the highest concentration within a few different foods, such as cocoa beans (Theobroma cacao), green tea, and black tea and in a lower concentration in herbal tea, peanuts (Arachis hypogaea), and pomegranates (Punica granatum) (-)-Epigallocatechin has also been detected, but not quantified in, several different foods, such as common beets (Beta vulgaris), pine nuts (Pinus), common mushrooms (Agaricus bisporus), red bell peppers (Capsicum annuum), and allia (Allium). This could make (-)-epigallocatechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (-)-Epigallocatechin. |
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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-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 | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Epigallocatechin, non-derivatized, GC-MS Spectrum | splash10-0a4i-0978700000-567c7251027c80e91a01 | Spectrum | GC-MS | Epigallocatechin, non-derivatized, GC-MS Spectrum | splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6 | Spectrum | GC-MS | Epigallocatechin, non-derivatized, GC-MS Spectrum | splash10-0a4i-0978700000-567c7251027c80e91a01 | Spectrum | GC-MS | Epigallocatechin, non-derivatized, GC-MS Spectrum | splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6 | Spectrum | Predicted GC-MS | Epigallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-0940000000-a9630fe8d1a042f59c2a | Spectrum | Predicted GC-MS | Epigallocatechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-3110049000-8b1040defcae8063c769 | Spectrum | Predicted GC-MS | Epigallocatechin, 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 - ESI-TOF 10V, Negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0pb9-0019003000-c4d2b02a82d1cf14714e | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0pb9-0019003000-c4d2b02a82d1cf14714e | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-002r-0910000000-8dfe0ba4e2ec1225213f | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0pb9-0019003000-c4d2b02a82d1cf14714e | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-00p0-0951000000-95142c4b42b35c4bdac9 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-000i-0900000000-4e9ebbe814af2f8c284d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Negative | splash10-05r0-0913000000-be7d3c4d9b40f51414e7 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0529000000-0036b0386a7ade78fcac | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00vi-0690000000-702c5a1e065692895b3a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00vi-0690000000-7844ed1a917693a67b37 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-002r-0910000000-8dfe0ba4e2ec1225213f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-00p0-0951000000-95142c4b42b35c4bdac9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0900000000-c79003b472daf421e492 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000i-0910000000-f92cf1606a46a5b16f4f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000i-0910000000-2026f33ac95d368b5268 | 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 |
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NMR | Not Available |
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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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