Record Information |
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Version | 1.0 |
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Creation date | 2011-04-08 19:48:08 UTC |
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Update date | 2019-11-26 03:20:53 UTC |
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Primary ID | FDB021797 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3-Hydroxybutanoic acid |
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Description | 3-Hydroxybutanoic acid is a ketone body. It is a chiral compound having two enantiomers. The concentration of beta-hydroxybutyrate, like that of other ketone bodies, is increased in ketosis. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA in a reaction catalyzed by the enzyme beta-hydroxybutyrate dehydrogenase and can be used as an energy source by the brain when blood glucose is low. Diabetic patients can have their ketone levels tested via urine or blood to indicate diabetic ketoacidosis. In alcoholic ketoacidosis, this ketone body is produced in greatest concentration. Both types of ketoacidosis result in an increasebeta-hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle stalling and shifting of glucose towards ketone body production. [Wikipedia] |
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CAS Number | 300-85-6 |
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Structure | |
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Synonyms | Synonym | Source |
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(1)-3-Hydroxybutyric acid | ChEBI | 3 HBA | ChEBI | 3-Hydroxybuttersaeure | ChEBI | 3-OH-Butyric acid | ChEBI | beta-Hydroxy-N-butyric acid | ChEBI | beta-Hydroxybutanoic acid | ChEBI | beta-Hydroxybuttersaeure | ChEBI | beta-Hydroxybutyric acid | ChEBI | BHBA | ChEBI | DL-beta-Hydroxybutyric acid | ChEBI | (1)-3-Hydroxybutyrate | Generator | 3-OH-Butyrate | Generator | b-Hydroxy-N-butyrate | Generator | b-Hydroxy-N-butyric acid | Generator | beta-Hydroxy-N-butyrate | Generator | Β-hydroxy-N-butyrate | Generator | Β-hydroxy-N-butyric acid | Generator | b-Hydroxybutanoate | Generator | b-Hydroxybutanoic acid | Generator | beta-Hydroxybutanoate | Generator | Β-hydroxybutanoate | Generator | Β-hydroxybutanoic acid | Generator | b-Hydroxybuttersaeure | Generator | Β-hydroxybuttersaeure | Generator | b-Hydroxybutyrate | Generator | b-Hydroxybutyric acid | Generator | beta-Hydroxybutyrate | Generator | Β-hydroxybutyrate | Generator | Β-hydroxybutyric acid | Generator | DL-b-Hydroxybutyrate | Generator | DL-b-Hydroxybutyric acid | Generator | DL-beta-Hydroxybutyrate | Generator | DL-Β-hydroxybutyrate | Generator | DL-Β-hydroxybutyric acid | Generator | 3-Hydroxybutyrate | Generator | 3-Hydroxy-butanoate | HMDB | 3-Hydroxy-butanoic acid | HMDB | 3-Hydroxy-butyrate | HMDB | 3-Hydroxy-butyric acid | HMDB | 3-Hydroxybutanoate | HMDB | 3-Hydroxybutanoic acid | HMDB | Biopol | HMDB | DL-3-Hydroxybutyrate | HMDB | DL-3-Hydroxybutyric acid | HMDB | beta Hydroxybutyric acid | HMDB | 3 Hydroxybutyric acid | HMDB | beta Hydroxybutyrate | HMDB | (+ -)-3-Hydroxybutyric acid | HMDB | 3 Hydroxybutyrate | HMDB | 3-Hydroxybutyric acid | manual | DL-β-hydroxybutyrate | Generator | DL-β-hydroxybutyric acid | Generator | β-hydroxy-N-butyrate | Generator | β-hydroxy-N-butyric acid | Generator | β-hydroxybutanoate | Generator | β-hydroxybutanoic acid | Generator | β-hydroxybuttersaeure | Generator | β-hydroxybutyrate | Generator | β-hydroxybutyric acid | Generator |
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Predicted Properties | |
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Chemical Formula | C4H8O3 |
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IUPAC name | 3-hydroxybutanoic acid |
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InChI Identifier | InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) |
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InChI Key | WHBMMWSBFZVSSR-UHFFFAOYSA-N |
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Isomeric SMILES | CC(O)CC(O)=O |
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Average Molecular Weight | 104.1045 |
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Monoisotopic Molecular Weight | 104.047344122 |
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Classification |
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Description | Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Beta hydroxy acids and derivatives |
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Direct Parent | Beta hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Short-chain hydroxy acid
- Beta-hydroxy acid
- Fatty acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Physico-Chemical Properties |
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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 | Not Available | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0007-9000000000-7fc414806153ebd8822c | 2014-09-20 | View Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-92be5c49a099fe1d9865 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-01ot-1920000000-c93138bf9d35643fef30 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, 2 TMS, GC-MS Spectrum | splash10-00dj-8900000000-e632e14fb4be28bdb786 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, 2 TMS, GC-MS Spectrum | splash10-014l-1900000000-e192caba63f034040624 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-92be5c49a099fe1d9865 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-01ot-1920000000-c93138bf9d35643fef30 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-00dj-8900000000-e632e14fb4be28bdb786 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-014l-1900000000-e192caba63f034040624 | Spectrum | GC-MS | 3-Hydroxybutanoic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-d06c5ac1a3733a38ea05 | Spectrum | Predicted GC-MS | 3-Hydroxybutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0007-9000000000-63f261a4dc876e264246 | Spectrum | Predicted GC-MS | 3-Hydroxybutanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01ei-9710000000-2652bd46b41e50defdb0 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0a4i-9200000000-4156904e7472b5e97249 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-9300000000-505ae46abb0c49c78b1e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0zfr-9600000000-dfed69c37c1a4d794440 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0zfr-4900000000-537084557f5986f16b31 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0zfr-4900000000-537084557f5986f16b31 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-000i-9000000000-7f0ec480b3c3c3911acd | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-9100000000-05c4623b015ff4300a6d | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05n0-9000000000-cbe0653845ffe4dc6ad4 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-e55d47308c7464e4cb22 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0zfr-8900000000-06dfbf939f6d19983ebe | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-9200000000-48b6e9b8656d41bff9cf | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-f7d61596ff4428fe6b09 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 428 |
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ChEMBL ID | CHEMBL1162496 |
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KEGG Compound ID | C01089 |
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Pubchem Compound ID | 441 |
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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 | HMDB00357 |
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CRC / DFC (Dictionary of Food Compounds) ID | GZG28-W:GZG28-W |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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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 | Beta-Hydroxybutyric_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 | Name | SMPDB Link | KEGG Link |
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Fatty Acid Biosynthesis | SMP00456 | 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 | |
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