Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:53 UTC |
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Update date | 2019-11-26 03:05:43 UTC |
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Primary ID | FDB011907 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Dehydroascorbic acid |
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Description | Dehydroascorbic acid, also known as dehydroascorbate, is a member of the class of compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Dehydroascorbic acid can be found in a number of food items such as white cabbage, gram bean, mexican groundcherry, and common pea, which makes dehydroascorbic acid a potential biomarker for the consumption of these food products. Dehydroascorbic acid may be a unique E.coli metabolite. Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids . |
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CAS Number | 490-83-5 |
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Structure | |
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Synonyms | Synonym | Source |
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Dehydroascorbate | ChEBI | Dehydroascorbates | ChEBI | threo-2,3-Hexodiulosono-1,4-lactone, 9CI, 8CI | db_source |
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Predicted Properties | |
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Chemical Formula | C6H6O6 |
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IUPAC name | 5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione |
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InChI Identifier | InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2 |
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InChI Key | SBJKKFFYIZUCET-UHFFFAOYSA-N |
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Isomeric SMILES | OCC(O)C1OC(=O)C(=O)C1=O |
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Average Molecular Weight | 174.1082 |
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Monoisotopic Molecular Weight | 174.016437924 |
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Classification |
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Description | Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactones |
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Sub Class | Gamma butyrolactones |
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Direct Parent | Gamma butyrolactones |
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Alternative Parents | |
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Substituents | - 3-furanone
- Gamma butyrolactone
- Tetrahydrofuran
- 1,2-diol
- Carboxylic acid ester
- Cyclic ketone
- Secondary alcohol
- Ketone
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Primary alcohol
- Organooxygen compound
- 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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Ontology | No ontology term |
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Physico-Chemical Properties |
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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 41.39%; H 3.47%; O 55.14% | DFC |
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Melting Point | Not Available | |
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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 | 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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Predicted GC-MS | Dehydroascorbic acid, TMS_1_1, 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 | splash10-056r-1900000000-9e9b54697233d78ff471 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-2900000000-e7da2430489db635dea0 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9200000000-decb0d5cef54ccf67907 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0229-1900000000-c546ba0f061c1d25a934 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0mbc-2900000000-254c596333e32143329f | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-08fr-9700000000-c03aa7ab2f0113898ab3 | 2015-09-15 | View Spectrum |
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NMR | Not Available |
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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 | Not Available |
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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 | HBR64-G:HBR64-G |
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EAFUS ID | Not Available |
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Dr. Duke ID | DEHYDROASCORBIC-ACID |
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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 | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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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 | Not Available |
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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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