Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:46 UTC |
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Update date | 2019-11-26 02:59:02 UTC |
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Primary ID | FDB003360 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | 3-Hydroxy-4,5-dimethyl-2(5H)-furanone |
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Description | 3-Hydroxy-4,5-dimethyl-2(5H)-furanone belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone is a strong, extremely sweet, and burnt tasting compound. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), robusta coffees (Coffea canephora), fenugreeks (Trigonella foenum-graecum), herbs and spices, and evergreen blackberries (Rubus laciniatus). This could make 3-hydroxy-4,5-dimethyl-2(5H)-furanone a potential biomarker for the consumption of these foods. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, with regard to humans, has been linked to the inborn metabolic disorder maple syrup urine disease. Based on a literature review very few articles have been published on 3-Hydroxy-4,5-dimethyl-2(5H)-furanone. |
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CAS Number | 28664-35-9 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C6H8O3 |
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IUPAC name | 3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one |
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InChI Identifier | InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3 |
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InChI Key | UNYNVICDCJHOPO-UHFFFAOYSA-N |
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Isomeric SMILES | CC1OC(=O)C(O)=C1C |
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Average Molecular Weight | 128.1259 |
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Monoisotopic Molecular Weight | 128.047344122 |
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Classification |
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Description | Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Dihydrofurans |
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Sub Class | Furanones |
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Direct Parent | Butenolides |
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Alternative Parents | |
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Substituents | - 2-furanone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Lactone
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Enol
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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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 | 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-9100000000-7fdd65bce51735b71d12 | Spectrum | Predicted GC-MS | 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05i0-9700000000-43cc2ff6f95044077419 | Spectrum | Predicted GC-MS | 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Hydroxy-4,5-dimethyl-2(5H)-furanone, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-9300000000-4d5cfb96c51ba990b353 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zi0-9200000000-3e0b5f2cf3a4e88018fa | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfr-9000000000-ac732b4b21400d1500e7 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-3900000000-26b4264da2affe2f394b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-3900000000-eb2c54bf2d77e47495b9 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0api-9000000000-1a81a14f56906486c81c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-5900000000-a9b9f4b7467f05d32c85 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0aos-9100000000-15b07a7cfd09c718a188 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-8bba3e142b490d9cfb12 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-1900000000-32e912844db31429eab0 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dl-9000000000-186c5ec73109434e3baa | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-7185ebac9651271eeeee | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 56569 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 62835 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB31306 |
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CRC / DFC (Dictionary of Food Compounds) ID | CWG65-S:CWG65-S |
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EAFUS ID | 994 |
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Dr. Duke ID | SOTOLONE |
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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 | 28664-35-9 |
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GoodScent ID | rw1029011 |
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SuperScent ID | 62835 |
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Wikipedia ID | Sotolon |
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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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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 | |
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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).
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