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 02:57:40 UTC |
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Primary ID | FDB002594 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | trans-p-Coumaric acid |
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Description | Widespread in plants, e.g. peel of black cherry (Prunus serotina), lentil seeds and from red clover (Trifolium pratense). Found by Bate-Smith in 48% of investigated dicotyledonous and 55% of monocotyledonous subspecies
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. trans-p-Coumaric acid is found in many foods, some of which are common buckwheat, radish, sweet orange, and avocado. |
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CAS Number | 501-98-4 |
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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 | (E)-p-Coumaric acid | biospider | (E)-p-Hydroxycinnamic acid | biospider | 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (E)- | biospider | Cinnamic acid, p-hydroxy-, (E)- | biospider | p-Coumaric acid, trans | biospider | trans-4-Hydroxycinnamic acid | biospider |
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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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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 | C 65.85%; H 4.91%; O 29.24% | DFC |
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Melting Point | Mp 210-213° | DFC |
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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 | pKa2 9.45 (25°) | DFC |
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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 | 286 (e 19000) (EtOH) (Berdy) | DFC |
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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 | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 498 |
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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 | CMP73-U:CMP74-V |
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EAFUS ID | Not Available |
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Dr. Duke ID | TRANS-P-COUMARIC-ACID|COUMARIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000580 |
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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 | 501-98-4 |
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GoodScent ID | rw1203781 |
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SuperScent ID | Not Available |
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Wikipedia ID | Coumaric_acid |
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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 | Flavor | Citations |
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balsamic |
- 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
| balsam |
- 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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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