| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:29 UTC |
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| Update date | 2019-11-26 02:54:35 UTC |
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| Primary ID | FDB000243 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Caffeic acid ethyl ester |
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| Description | Caffeic acid ethyl ester, also known as (E)-ethyl 3,4-dihydroxycinnamate or (E)-ethyl caffeate, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Caffeic acid ethyl ester is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeic acid ethyl ester can be found in eggplant and vinegar, which makes caffeic acid ethyl ester a potential biomarker for the consumption of these food products. Ethyl caffeate is an ester of an hydroxycinnamic acid, a naturally occurring organic compound . |
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| CAS Number | 102-37-4 |
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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 | C11H12O4 |
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| IUPAC name | ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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| InChI Identifier | InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+ |
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| InChI Key | WDKYDMULARNCIS-GQCTYLIASA-N |
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| Isomeric SMILES | CCOC(=O)\C=C\C1=CC(O)=C(O)C=C1 |
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| Average Molecular Weight | 208.2106 |
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| Monoisotopic Molecular Weight | 208.073558872 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Cinnamic acids and derivatives |
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| Sub Class | Hydroxycinnamic acids and derivatives |
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| Direct Parent | Coumaric acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Coumaric acid or derivatives
- Cinnamic acid ester
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Fatty acid ester
- Fatty acyl
- Benzenoid
- Monocyclic benzene moiety
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Ontology | No ontology term |
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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 | Not Available | |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | 2.56 | HANSCH,C ET AL. (1995) |
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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 | Not Available | |
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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 | Caffeic acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03g0-2900000000-c16a5811eae4cc57741a | 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 | splash10-0a4i-1890000000-bac15703d62d288bae8b | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08fr-3910000000-851348d6ede682401375 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-9800000000-447a54bed40ab435643f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0bt9-2790000000-8a20e8b5192c8f9ba3f1 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fr-3920000000-a5cfde27b3fb97857e9e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03dj-4900000000-1f4744d8c108b7f47fc0 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08fr-0950000000-d2c1d1796989e2b3fe1a | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08g1-0910000000-a4f99bb22be28136622c | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rj-6900000000-94a781fc016decb68ef5 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0390000000-70f10da8be018d1b5add | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-2900000000-7ab4f3330a50bf996fba | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001u-2900000000-86fade974acbd7c34700 | 2021-10-21 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C10484 |
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| Pubchem Compound ID | 5317238 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 473 |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | ETHYL-CAFFEATE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00030221 |
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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 | Not Available |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.
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