Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:23 UTC |
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Update date | 2019-11-26 03:04:24 UTC |
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Primary ID | FDB010971 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4-Hydroxy-2H-1-benzopyran-2-one |
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Description | 4-Hydroxy-2H-1-benzopyran-2-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 4-Hydroxy-2H-1-benzopyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxy-2H-1-benzopyran-2-one is found, on average, in the highest concentration within grape wines and beers. This could make 4-hydroxy-2H-1-benzopyran-2-one a potential biomarker for the consumption of these foods. |
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CAS Number | 1076-38-6 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Hydroxy-4H-1-benzopyran-4-one | db_source | 2-Hydroxychromone | db_source | 2H-1-Benzopyran-2-one, 4-hydroxy- | biospider | 2H-1-Benzopyran-2,4(3H)-dione | db_source | 3-(4-Hydroxyphenyl)-1-propane | HMDB | 3-OHPP | HMDB | 4-Coumarinol | manual | 4-Hydroxy-2H-chromen-2-one | biospider | 4-Hydroxycinnamyl alcohol | ChEBI | 4-Hydroxycoumarin | db_source | 4-Hydroxycoumarine | biospider | Benzotetronate | biospider | Benzotetronic acid | db_source | Coumarin, 4-hydroxy- | biospider | Hydroxy coumarin | HMDB | P-Coumaryl alcohol | ChEBI |
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Predicted Properties | |
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Chemical Formula | C9H6O3 |
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IUPAC name | 2-hydroxy-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,11H |
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InChI Key | OWBBAPRUYLEWRR-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC(=O)C2=CC=CC=C2O1 |
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Average Molecular Weight | 162.144 |
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Monoisotopic Molecular Weight | 162.031694053 |
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Classification |
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Description | Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Not Available |
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Direct Parent | Coumarins and derivatives |
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Alternative Parents | |
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Substituents | - Chromone
- Coumarin
- Benzopyran
- 1-benzopyran
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 66.67%; H 3.73%; O 29.60% | DFC |
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Melting Point | Mp 232-233° | DFC |
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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 | 262 (e 11900) (EtOH) (Derep) | 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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Predicted GC-MS | 4-Hydroxy-2H-1-benzopyran-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-045c-3900000000-4a2fc840ec22a83d909e | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-9975e24c3ae0661c2ee6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-6fff3bff2c39de5e55e0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0229-7900000000-aa26a1d2ff6b75b366a9 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-700569317f85cc30b3b1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-842ec05607fb73b39974 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9400000000-d57d27787cee8ff65bd0 | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4444166 |
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ChEMBL ID | CHEMBL109034 |
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KEGG Compound ID | C02646 |
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Pubchem Compound ID | 5280535 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 642 |
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DrugBank ID | DB03410 |
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HMDB ID | HMDB03654 |
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CRC / DFC (Dictionary of Food Compounds) ID | FXG77-L:FXG77-L |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 2299830 |
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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 | 4-Hydroxycoumarins |
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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 | Name | Gene Name | UniProt ID |
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Peroxiredoxin-6 | PRDX6 | P30041 |
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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.
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