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 | Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. m-Coumaric acid is found in many foods, some of which are corn, garden tomato (variety), grape wine, and beer. |
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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 | HMDB | Meta-coumaric acid | 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 | 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 |
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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 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-014i-4900000000-2157a17ec65ead35585e | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00kf-9300000000-3325dd31a734dd4659bb | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-0900000000-be33d196fbb525019f07 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03di-0900000000-be33d196fbb525019f07 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0900000000-d256885fb0f35d3d6680 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0900000000-b5ad37fb931b464df7d5 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-1900000000-c66c146ee9509bf8a413 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fvi-9700000000-fcc332df0fcb818fe0e0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-408ac0dd815354188750 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-146bae2da386ca2d4f1a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014m-3900000000-235b38f342376d1c9f90 | Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum | | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | | 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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