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 | 2020-09-17 15:31:12 UTC |
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Primary ID | FDB002593 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | p-Coumaric acid |
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Description | trans-4-Coumaric acid or (e)-p-Coumaric acid, the trans-isomer of 4-coumaric acid, also known as 4-hydroxycinnamic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid is a neutral compound. 4-Hydroxycinnamic acid exists in all living species, from bacteria to humans. 4-Hydroxycinnamic acid is found in highest concentrations in pepper (c. frutescens), pineapples, and sunflowers and in lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected in wild rices, soursops, garden onions, hyssops, and avocado. This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods. |
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CAS Number | 7400-08-0 |
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Structure | |
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Synonyms | Synonym | Source |
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(2E)-3-(4-Hydroxyphenyl)acrylic acid | ChEBI | (e)-3-(4-Hydroxyphenyl)-2-propenoic acid | ChEBI | (e)-p-Coumaric acid | ChEBI | (e)-p-Hydroxycinnamic acid | ChEBI | 4'-HYDROXYCINNAMIC ACID | ChEBI | Naringeninic acid | ChEBI | p-Coumaric acid | ChEBI | trans-p-Coumaric acid | ChEBI | trans-p-Coumarinic acid | ChEBI | trans-p-Hydroxycinnamate | ChEBI | trans-p-Hydroxycinnamic acid | ChEBI | trans-4-Hydroxycinnamate | Kegg | 4-Hydroxycinnamate | Kegg | (2E)-3-(4-Hydroxyphenyl)acrylate | Generator | (e)-3-(4-Hydroxyphenyl)-2-propenoate | Generator | (e)-p-Coumarate | Generator | (e)-p-Hydroxycinnamate | Generator | 4'-HYDROXYCINNAMate | Generator | Naringeninate | Generator | p-Coumarate | Generator | trans-p-Coumarate | Generator | trans-p-Coumarinate | Generator | 4-Coumaric acid, (e)-isomer | MeSH | 4-Coumaric acid, (Z)-isomer | MeSH | 4-Coumaric acid, disodium salt | MeSH | p-Coumaryl alcohol | MeSH | p-Hydroxycinnamic acid | MeSH | Para-coumaric acid | MeSH | trans-3-(4'-Hydroxyphenyl)-2-propenoic acid | MeSH | trans-HPPA | MeSH | 3-(4-Hydroxyphenyl)-2-propenoate | HMDB | 3-(4-Hydroxyphenyl)-2-propenoic acid | HMDB | 3-(4-Hydroxyphenyl)acrylate | HMDB | 3-(4-Hydroxyphenyl)acrylic acid | HMDB | 4-Coumarate | HMDB | 4-Hydroxy cinnamate | HMDB | 4-Hydroxy cinnamic acid | HMDB | 4-Hydroxyphenylpropenoate | HMDB | 4-Hydroxyphenylpropenoic acid | HMDB | b-[4-Hydroxyphenyl]acrylate | HMDB | b-[4-Hydroxyphenyl]acrylic acid | HMDB | beta-[4-Hydroxyphenyl]acrylate | HMDB | beta-[4-Hydroxyphenyl]acrylic acid | HMDB | cis-P-Coumarate | HMDB | Hydroxycinnamate | HMDB | Hydroxycinnamic acid | HMDB | P-Cumarate | HMDB | P-Cumaric acid | HMDB | P-Hydroxycinnamate | HMDB | P-Hydroxyphenylacrylate | HMDB | P-Hydroxyphenylacrylic acid | HMDB | Para coumarate | HMDB | Para coumaric acid | HMDB | Para-coumarate | HMDB | 4-Hydroxycinnamic acid | ChEBI | trans-4-Coumarate | Generator, HMDB | (2E)-3-(4-Hydroxyphenyl)-2-propenoic acid | HMDB | (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid | HMDB | (E)-3-(4-Hydroxyphenyl)acrylic acid | HMDB | (E)-4-Hydroxycinnamic acid | HMDB | 4’-Hydroxycinnamic acid | HMDB | p-Cumaric acid | HMDB | p-Hydroxy-trans-cinnamic acid | HMDB | p-Hydroxyphenylacrylic acid | HMDB | p-trans-Coumaric acid | HMDB | trans-3-(4-Hydroxyphenyl)-2-propenoic acid | HMDB | trans-4-Coumaric acid | HMDB | β-[4-Hydroxyphenyl]acrylic acid | HMDB | (2e)-3-(4-Hydroxyphenyl)acrylate | Generator | (2e)-3-(4-Hydroxyphenyl)acrylic acid | ChEBI | (e)-P-Coumarate | Generator | (e)-P-Hydroxycinnamate | Generator | 4-Coumaric acid | biospider | p-Cumarate | biospider | p-Hydroxy-cinnamic acid | biospider | p-Hydroxycinnamate | biospider | P-Hydroxycinnamic acid | HMDB | p-Hydroxycinnamic acid, 8CI | db_source | p-Hydroxyphenylacrylate | biospider | para-Coumarate | biospider | para-Coumaric acid | biospider | trans-P-Coumarinate | Generator |
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Predicted Properties | |
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Chemical Formula | C9H8O3 |
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IUPAC name | (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid |
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InChI Identifier | InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ |
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InChI Key | NGSWKAQJJWESNS-ZZXKWVIFSA-N |
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Isomeric SMILES | OC(=O)\C=C\C1=CC=C(O)C=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-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: Source: Biological location: |
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Role | Biological role: Industrial application: |
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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 | 211.5 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 1.79 | SANGSTER (1994) |
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Experimental pKa | 4.64 | |
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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-6900000000-348f5c7c030570e0612f | 2015-03-01 | View Spectrum | GC-MS | p-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-014m-1981000000-e7648e85764a445a919c | Spectrum | GC-MS | p-Coumaric acid, 2 TMS, GC-MS Spectrum | splash10-066v-3791000000-a5712bbe8401ef499b5a | Spectrum | GC-MS | p-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-03di-8900000000-3bb023f80c1f54a16adc | Spectrum | GC-MS | p-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-03xr-5900000000-a364c62c9122c0fbe6de | Spectrum | GC-MS | p-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-014m-1981000000-e7648e85764a445a919c | Spectrum | GC-MS | p-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-066v-3791000000-a5712bbe8401ef499b5a | Spectrum | GC-MS | p-Coumaric acid, non-derivatized, GC-MS Spectrum | splash10-014m-1891000000-d8804981d3918cac534d | Spectrum | Predicted GC-MS | p-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014j-2900000000-7075c3e10f9df528109e | Spectrum | Predicted GC-MS | p-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00xu-6390000000-3110f0f6eb462a38bb64 | Spectrum | Predicted GC-MS | p-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 - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-0900000000-b58aab08954c973df04e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-014i-0900000000-3ddb41572ba36a950e37 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-014i-0900000000-ccac7f071084bc660095 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-014i-3900000000-5dc8af06da0120779cff | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-00kf-9500000000-9187edc4498ab4345e5a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-014i-0900000000-3d831c6acd9d3188de2f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-0900000000-fbb6439b7d012045f3a8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0002-0900000000-9e18d43a8d86f9b9e72b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Negative | splash10-014i-0900000000-c45397049a7ba500b332 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-0900000000-b58aab08954c973df04e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-3ddb41572ba36a950e37 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-ccac7f071084bc660095 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-3900000000-5dc8af06da0120779cff | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00kf-9500000000-9187edc4498ab4345e5a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0900000000-3d831c6acd9d3188de2f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03di-0900000000-fbb6439b7d012045f3a8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0900000000-9e18d43a8d86f9b9e72b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-c6491d0aaba639e3ae07 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0002-0900000000-9e18d43a8d86f9b9e72b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-014i-0900000000-a183cce49af676c95d4e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-1f13fa0e7a24be298cfb | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-206402014014906dbe29 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive | splash10-03di-8900000000-3bb023f80c1f54a16adc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00kb-3900000000-1118928776a5a6e213db | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-0002-0900000000-c5faa58d353ca1466c3c | 2017-09-14 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, DMSO, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, DMSO, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | 553148 |
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ChEMBL ID | CHEMBL66879 |
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KEGG Compound ID | C00811 |
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Pubchem Compound ID | 637542 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 500 |
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DrugBank ID | DB04066 |
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HMDB ID | HMDB02035 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMP73-U:CMP73-U |
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EAFUS ID | Not Available |
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Dr. Duke ID | 4-HYDROXYCINNAMIC-ACID|P-COUMARIC-ACID|P-HYDROXYCINNAMIC-ACID |
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BIGG ID | 36077 |
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KNApSAcK ID | C00000152 |
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HET ID | HC4 |
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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 | 454 |
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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 | Descriptor | ID | Definition | Reference |
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aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | allelopathic | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti clastogen | | | DUKE | anti fertility | | | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti nitrosaminic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti peroxidant | | | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | chemopreventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | choleretic | | | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | diaphoretic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | prostaglandigenic | | | DUKE | prostaglandin synthesis inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | tyrosinase inhibitor | 59997 | Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals. | 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 | 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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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