Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:26 UTC |
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Update date | 2019-11-26 02:57:39 UTC |
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Primary ID | FDB002590 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | m-Coumaric acid |
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Description | m-Coumaric acid, also known as 3-coumarate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. m-Coumaric acid exists in all living organisms, ranging from bacteria to humans. m-Coumaric acid is found, on average, in the highest concentration within a few different foods, such as olives (Olea europaea), pears (Pyrus communis), and beer and in a lower concentration in corns (Zea mays). m-Coumaric acid has also been detected, but not quantified in, several different foods, such as grapes (Vitis), spinaches (Spinacia oleracea), arabica coffees (Coffea arabica), garden tomato (var.), and anatidaes (Anatidae). This could make m-coumaric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on m-Coumaric acid. |
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CAS Number | 588-30-7 |
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Structure | |
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Synonyms | Synonym | Source |
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(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid | ChEBI | (2E)-3-(3-Hydroxyphenyl)acrylic acid | ChEBI | (e)-3-(3-Hydroxyphenyl)-2-propenoic acid | ChEBI | m-Hydroxycinnamic acid | ChEBI | trans-3-Hydroxycinnamate | ChEBI | trans-3-Hydroxycinnamic acid | ChEBI | (2E)-3-(3-Hydroxyphenyl)prop-2-enoate | Kegg | (2E)-3-(3-Hydroxyphenyl)-2-propenoate | Generator | (2E)-3-(3-Hydroxyphenyl)acrylate | Generator | (e)-3-(3-Hydroxyphenyl)-2-propenoate | Generator | 3-Coumarate | Generator | m-Hydroxycinnamate | Generator | (2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid | Generator | m-Coumarate | Generator | 3'-Hydroxycinnamate | HMDB | 3'-Hydroxycinnamic acid | HMDB | 3-(3-Hydroxyphenyl)-2-propenoate | HMDB | 3-(3-Hydroxyphenyl)-2-propenoic acid | HMDB | 3-(3-Hydroxyphenyl)acrylate | HMDB | 3-(3-Hydroxyphenyl)acrylsaeure | HMDB | 3-(3-Hydroxyphenyl)prop-2-enoate | HMDB | 3-(3-Hydroxyphenyl)prop-2-enoic acid | HMDB | 3-Hydroxycinnamate | HMDB | 3-Hydroxycinnamic acid | HMDB | m-Hydroxy-cinnamate | HMDB | m-Hydroxy-cinnamic acid | HMDB | 3-Coumaric acid, (e)-isomer | MeSH, HMDB | Meta-coumaric acid | MeSH, HMDB | (E)-3-(3-Hydroxyphenyl)acrylic acid | HMDB | (E)-3-Hydroxycinnamic acid | HMDB | trans-3-(m-Hydroxyphenyl)-2-propenoic acid | HMDB | trans-m-Coumaric acid | HMDB | trans-m-Hydroxycinnamic acid | HMDB | trans-3-Coumarate | HMDB | (2e)-3-(3-Hydroxyphenyl)acrylate | Generator | 3-(3-Hydroxyphenyl)acrylic acid | HMDB | 3-Coumaric acid | ChEBI | m-Coumaric acid | db_source | m-Cumaric acid | db_source |
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Predicted Properties | |
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Chemical Formula | C9H8O3 |
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IUPAC name | (2E)-3-(3-hydroxyphenyl)prop-2-enoic acid |
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InChI Identifier | InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ |
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InChI Key | KKSDGJDHHZEWEP-SNAWJCMRSA-N |
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Isomeric SMILES | OC(=O)\C=C\C1=CC=CC(O)=C1 |
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Average Molecular Weight | 164.158 |
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Monoisotopic Molecular Weight | 164.047344122 |
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Classification |
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Description | Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
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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 | Hydroxycinnamic acids |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Coumaric acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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Disposition | Route of exposure: Biological location: Source: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: 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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 65.85%; H 4.91%; O 29.24% | DFC |
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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 | 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 | 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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-03xr-7900000000-61ee2ad0ad164a1f7550 | 2015-03-01 | View Spectrum | GC-MS | m-Coumaric acid, 2 TMS, GC-MS Spectrum | splash10-0udl-1691000000-331053d0d0b85549ac0b | Spectrum | GC-MS | m-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-0udl-1691000000-331053d0d0b85549ac0b | Spectrum | GC-MS | m-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-0udi-1891000000-049e1d80dd47b23e8c28 | Spectrum | Predicted GC-MS | m-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-02t9-2900000000-91ffd4c10eaed6a17632 | Spectrum | Predicted GC-MS | m-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00y3-6390000000-f1a30e2fb9cd1fb11341 | Spectrum | Predicted GC-MS | m-Coumaric acid, 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 - Quattro_QQQ 10V, Negative (Annotated) | splash10-03xr-0900000000-4259219e89806dfe2602 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-014i-4900000000-2157a17ec65ead35585e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00kf-9300000000-3325dd31a734dd4659bb | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-0900000000-be33d196fbb525019f07 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03di-0900000000-be33d196fbb525019f07 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-1900000000-87be0242c9f5b426f6b8 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-014l-9000000000-9e4128fa078e73e71cba | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0006-9100000000-1865c168df491277a4d3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0006-9000000000-296d14129321002679a3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00kf-9700000000-6d29cdde66b32806de5f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-9da76da83e0462c48acf | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-bf33c5b8f5901c60b332 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-014i-2900000000-11ae76e2fe36da1dfbe6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-b6bf0b46b2fa8324cf71 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-00kb-0900000000-1065251e7cf92f343533 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-004i-9000000000-0a87c81608b3fbcee7c9 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0900000000-b5ad37fb931b464df7d5 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-1900000000-c66c146ee9509bf8a413 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvi-9700000000-fcc332df0fcb818fe0e0 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-408ac0dd815354188750 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-146bae2da386ca2d4f1a | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014m-3900000000-235b38f342376d1c9f90 | 2017-06-28 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 553147 |
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ChEMBL ID | CHEMBL98521 |
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KEGG Compound ID | C12621 |
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Pubchem Compound ID | 637541 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 47925 |
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Phenol-Explorer ID | 463 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB01713 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMP64-S:CMP64-S |
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EAFUS ID | Not Available |
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Dr. Duke ID | M-COUMARIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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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 | Coumaric_acid |
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Phenol-Explorer Metabolite ID | 463 |
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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 | show |
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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. — 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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