Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:56 UTC |
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Update date | 2019-11-26 03:05:56 UTC |
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Primary ID | FDB012002 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Ethyl cinnamate |
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Description | Ethyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Ethyl cinnamate is a sweet, balsam, and berry tasting compound. Ethyl cinnamate is found, on average, in the highest concentration within red wine. Ethyl cinnamate has also been detected, but not quantified in, several different foods, such as ceylon cinnamons (Cinnamomum verum), evergreen blackberries (Rubus laciniatus), tamarinds (Tamarindus indica), blackberries (Rubus), and tarragons (Artemisia dracunculus). This could make ethyl cinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Ethyl cinnamate. |
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CAS Number | 4192-77-2 |
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Structure | |
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Synonyms | Synonym | Source |
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Ethyl cinnamic acid | Generator | (e)-Ethyl cinnamate | HMDB | 3-Phenyl-ethyl ester(e)-2-propenoic acid | HMDB | Ethyl (2E)-3-phenyl-2-propenoate | HMDB | Ethyl (2E)-3-phenylacrylate | HMDB | Ethyl (e)-cinnamate | HMDB | Ethyl cinnamate, trans | HMDB | Ethyl trans-cinnamate | HMDB | FEMA 2430 | HMDB | trans-Ethyl cinnamate | HMDB | Ethyl (2Z)-3-phenylprop-2-enoic acid | Generator | (e)-ethyl cinnamate | biospider | 2-Propenoic acid, 3-phenyl-, ethyl ester, (E)- | biospider | Trans-ethyl cinnamate | biospider |
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Predicted Properties | |
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Chemical Formula | C11H12O2 |
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IUPAC name | ethyl (2Z)-3-phenylprop-2-enoate |
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InChI Identifier | InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8- |
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InChI Key | KBEBGUQPQBELIU-HJWRWDBZSA-N |
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Isomeric SMILES | CCOC(=O)\C=C/C1=CC=CC=C1 |
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Average Molecular Weight | 176.2118 |
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Monoisotopic Molecular Weight | 176.083729628 |
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Classification |
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Description | Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. |
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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 | Cinnamic acid esters |
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Direct Parent | Cinnamic acid esters |
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Alternative Parents | |
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Substituents | - Cinnamic acid ester
- Styrene
- Fatty acid ester
- Monocyclic benzene moiety
- Benzenoid
- Fatty acyl
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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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 | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 74.98%; H 6.86%; O 18.16% | DFC |
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Melting Point | Mp 12° | DFC |
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Boiling Point | Bp24 159° | DFC |
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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 | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d2525 1.05 | DFC |
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Refractive Index | n20D 1.5590 | DFC |
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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 | Ethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fai-3900000000-a8d987a548c9fa6c7f2d | Spectrum | Predicted GC-MS | Ethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Ethyl cinnamate, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-061762de8ea8d97b5cfa | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-4900000000-c561bd073358d027fd92 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufu-9500000000-f3a99db2bb06534a646b | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-b7e60492dd7bc9500be1 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2900000000-2240e17326bb0662c91c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fba-3900000000-0d609d9bc26a486298ca | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-ba8ba15dbd02ca4eec9e | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-1900000000-935e6ce292933740c493 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufr-6900000000-f309c938a129dc5470f6 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-d4773b1f6c6f68c13fae | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1900000000-002df14c18a57d0f27a0 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fb9-9500000000-502a9fa131a679c46ac9 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4447700 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 5284656 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB33834 |
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CRC / DFC (Dictionary of Food Compounds) ID | HCV54-E:HCL40-Z |
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EAFUS ID | 1162 |
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Dr. Duke ID | CINNAMIC-ACID-ETHYL-ESTER|ETHYL-CINNAMATE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00035614 |
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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 | 4192-77-2 |
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GoodScent ID | rw1014811 |
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SuperScent ID | 637758 |
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Wikipedia ID | Ethyl_cinnamate |
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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 | Descriptor | ID | Definition | Reference |
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cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | 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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flower |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| honey |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| cinnamon |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| plum |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| balsam |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fruity |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| powdery |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| berry |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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).
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