Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 03:17:09 UTC |
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Update Date | 2023-02-21 17:28:50 UTC |
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HMDB ID | HMDB0041592 |
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Secondary Accession Numbers | - HMDB0062655
- HMDB41592
- HMDB62655
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Metabolite Identification |
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Common Name | Coumarinic acid |
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Description | Coumarinic acid, also known as cis-o-coumaric acid or cis-o-hydroxycinnamic acid, is a hydroxy derivative of cinnamic acid. Cinnamic acid and its derivatives are used as important components in flavours, perfumes, synthetic indigo, and pharmaceuticals. There are three isomers of coumaric acid: o-coumaric acid, m-coumaric acid, and p-coumaric acid. These isomers differ by the position of the hydroxy substitution. p-Coumaric acid is the most abundant isomer in nature (Wikipedia ). Coumarinic acid is found in pomegranate. |
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Structure | OC(=O)\C=C/C1=C(O)C=CC=C1 InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5- |
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Synonyms | Value | Source |
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(2Z)-3-(2-Hydroxyphenyl)acrylic acid | ChEBI | 2-Coumarinate | ChEBI | cis-2-Hydroxy cinnamate | ChEBI | cis-2-Hydroxycinnamic acid | ChEBI | (2Z)-3-(2-Hydroxyphenyl)acrylate | Generator | 2-Coumarinic acid | Generator | cis-2-Hydroxy cinnamic acid | Generator | cis-2-Hydroxycinnamate | Generator | Coumarinate | Generator | Coumarate | Generator, HMDB | (Z)-Form | HMDB | 3-(2-Hydroxyphenyl)-(2Z)-2-propenoic acid | HMDB | 3-(2-Hydroxyphenyl)-(Z)-2-propenoic acid | HMDB | 3-(2-Hydroxyphenyl)-2-propenoic acid, 9ci | HMDB | Cinnamic acid, O-hydroxy-, (Z)- (8ci) | HMDB | cis-O-Coumaric acid | HMDB | cis-O-Hydroxycinnamic acid | HMDB | Coumarinic acid | HMDB | cis-2-Coumarate | Generator, HMDB | (2Z)-3-(2-Hydroxyphenyl)-2-propenoic acid | HMDB | (Z)-2-Hydroxycinnamic acid | HMDB | (Z)-3-(2-Hydroxyphenyl)acrylic acid | HMDB | (Z)-o-Hydroxycinnamic acid | HMDB | 2-Coumaric acid | HMDB | 2-Hydroxycinnamic acid | HMDB | 3-(2-Hydroxyphenyl)-2-propenoic acid | HMDB | cis-o-Coumaric acid | HMDB | cis-o-Hydroxycinnamic acid | HMDB | o-Coumaric acid | HMDB | o-Hydroxy-cis-cinnamic acid | HMDB | o-Hydroxycinnamic acid | HMDB |
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Chemical Formula | C9H8O3 |
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Average Molecular Weight | 164.158 |
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Monoisotopic Molecular Weight | 164.047344122 |
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IUPAC Name | (2Z)-3-(2-hydroxyphenyl)prop-2-enoic acid |
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Traditional Name | 2-coumarinate |
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CAS Registry Number | 495-79-4 |
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SMILES | OC(=O)\C=C/C1=C(O)C=CC=C1 |
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InChI Identifier | InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5- |
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InChI Key | PMOWTIHVNWZYFI-WAYWQWQTSA-N |
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Chemical Taxonomy |
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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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Coumarinic acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)/C=C\C1=CC=CC=C1O | 1834.0 | Semi standard non polar | 33892256 | Coumarinic acid,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=CC=C1/C=C\C(=O)O | 1787.8 | Semi standard non polar | 33892256 | Coumarinic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)/C=C\C1=CC=CC=C1O[Si](C)(C)C | 1833.2 | Semi standard non polar | 33892256 | Coumarinic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=CC=C1O | 2068.0 | Semi standard non polar | 33892256 | Coumarinic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=CC=C1/C=C\C(=O)O | 2077.8 | Semi standard non polar | 33892256 | Coumarinic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=CC=C1O[Si](C)(C)C(C)(C)C | 2300.4 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Coumarinic acid GC-MS (2 TMS) | splash10-01ox-1941000000-85dd77bfea7f6b8125b7 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Coumarinic acid GC-MS (Non-derivatized) | splash10-01ox-1941000000-85dd77bfea7f6b8125b7 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Coumarinic acid GC-EI-TOF (Non-derivatized) | splash10-0002-1910000000-73438ba0cdf6f364fa48 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Coumarinic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-1900000000-6663bcef745d1f3aa724 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Coumarinic acid GC-MS (2 TMS) - 70eV, Positive | splash10-00y3-6390000000-a82ff5bd6498e3c478ea | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Coumarinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Coumarinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 10V, Positive-QTOF | splash10-014j-0900000000-ba0915b2f87da989c92b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 20V, Positive-QTOF | splash10-014i-2900000000-fd2da9ac5865a50fc50c | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 40V, Positive-QTOF | splash10-0gdu-9300000000-3baee6b4124fba79677e | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 10V, Negative-QTOF | splash10-03di-0900000000-69f05779283af436427d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 20V, Negative-QTOF | splash10-03xr-1900000000-0bc76f24c2abf6670fc0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 40V, Negative-QTOF | splash10-0006-9600000000-a2981a5342a71b94ce69 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 10V, Positive-QTOF | splash10-014j-0900000000-d75d91b3944a2cbb443c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 20V, Positive-QTOF | splash10-014i-1900000000-4cc760aa4a932aabf83e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 40V, Positive-QTOF | splash10-0ftf-9300000000-3a6e7e80a1f918c0bb34 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 10V, Negative-QTOF | splash10-014i-0900000000-972f865a96261dcb891a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 20V, Negative-QTOF | splash10-014j-0900000000-dfdb5072d39445a67f3a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Coumarinic acid 40V, Negative-QTOF | splash10-014i-8900000000-badf365b10d631e59196 | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021703 |
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KNApSAcK ID | C00019207 |
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Chemspider ID | 4444389 |
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KEGG Compound ID | C05838 |
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BioCyc ID | CPD-7418 |
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BiGG ID | Not Available |
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Wikipedia Link | Coumaric acid |
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METLIN ID | Not Available |
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PubChem Compound | 5280841 |
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PDB ID | Not Available |
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ChEBI ID | 28873 |
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Food Biomarker Ontology | Not Available |
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VMH ID | 2COUM |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1559231 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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