Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:12:51 UTC |
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Update date | 2019-11-26 03:14:15 UTC |
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Primary ID | FDB017126 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | ent-Epicatechin |
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Description | (+)-Epicatechin, also known as ent-epicatechin, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol (+)-Epicatechin is found, on average, in the highest concentration within pears (Pyrus communis) (+)-Epicatechin has also been detected, but not quantified in, several different foods, such as star fruits (Averrhoa carambola), red tea, common buckwheats (Fagopyrum esculentum), apples (Malus pumila), and asian pears (Pyrus pyrifolia). This could make (+)-epicatechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (+)-Epicatechin. |
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CAS Number | 35323-91-2 |
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Structure | |
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Synonyms | Synonym | Source |
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(2S,3S)-3',4',5,7-Tetrahydroxyflavan-3-ol | ChEBI | (2S,3S)-3,3',4',5,7-Pentahydroxyflavan | ChEBI | ent-Epicatechin | ChEBI | (+)-cis-3,3',4',5,7-Pentahydroxyflavan | HMDB | (+)-Epicatechol | HMDB | (2S,3S)-(+)-Epicatechin | HMDB | (2S-cis)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol | HMDB | Catechin C | HMDB | D-Epicatechin | HMDB | (+)-Epicatechin | manual | (2S-cis)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-Benzopyran-3,5,7-triol | manual | 3,3',4',5,7-Pentahydroxyflavan; (+)-cis-form | db_source | 3,3',4',5,7-Pentahydroxyflavan; (2S,3S)-form | db_source | d-Epicatechin | manual |
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Predicted Properties | |
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Chemical Formula | C15H14O6 |
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IUPAC name | (2S,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
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InChI Identifier | InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m0/s1 |
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InChI Key | PFTAWBLQPZVEMU-ZFWWWQNUSA-N |
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Isomeric SMILES | O[C@H]1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C=C(O)C=C2O |
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Average Molecular Weight | 290.2681 |
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Monoisotopic Molecular Weight | 290.07903818 |
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Classification |
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Description | Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. |
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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 | Catechins |
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Alternative Parents | |
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Substituents | - Catechin
- 3'-hydroxyflavonoid
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromane
- Benzopyran
- 1-benzopyran
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Ether
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- 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 - 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 62.07%; H 4.86%; O 33.07% | DFC |
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Melting Point | Mp 235-237° | 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]20D +59 (c, 2 in 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 | Epicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-0940000000-635a87e4fbbe005b1b88 | Spectrum | Predicted GC-MS | Epicatechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-3130069000-ca0968505fc89dd82640 | Spectrum | Predicted GC-MS | Epicatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Epicatechin, 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-QTOF , negative | splash10-052r-0980000000-b5cee6aae1e7952a7d9f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0079-0900000000-9a4ec6a24f97ad3fd9f2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00di-0900000000-c152f224fc3c49acdeb5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-007c-0920000000-91de0a80259cfbc0113b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00dr-0900000000-437372b0d194754905ce | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0g6r-0900000000-5069537b6f392aae0fe1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0590000000-516859cd7060b2bf898b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-000i-0910000000-7236013988c20252d8c7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0079-0900000000-9afe75272afab175f889 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-01bi-2900000000-56fefff3a8f788f1a1ca | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0006-0490000000-1b85894a81aba913bda3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0490000000-80c202adef30df74053b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0910000000-fd8f0d6d6ee1a117d994 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-007c-0920000000-ca2ff9eca6136f481a1d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0690000000-31f869b582ff052495f7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0079-0910000000-7c1c4c01e56414dde318 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0006-0590000000-b3372a9dc6a409ae8998 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0079-0900000000-9731a6caadd423aea0a1 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0290000000-52e8123f5ed55bc47962 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0940000000-cfcd9b4e416f64a26916 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a6r-2910000000-be77474275eeee51824b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-f6afeb92914fea4cf8de | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-0690000000-76f0c4a6b193c78824c1 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dr-1940000000-cc596c4cbd5f45583cb1 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0590000000-aff1c3cc94786f87cacf | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 158494 |
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ChEMBL ID | CHEMBL129482 |
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KEGG Compound ID | C09728 |
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Pubchem Compound ID | 182232 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 147 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB37954 |
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CRC / DFC (Dictionary of Food Compounds) ID | CML31-M:KWF80-Y |
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EAFUS ID | Not Available |
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Dr. Duke ID | (+)-EPICATECHIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000957 |
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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 | Catechin |
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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 | Not Available |
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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 | 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 | — 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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