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Identification |
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YMDB ID | YMDB00441 |
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Name | 2-hydroxybutyric acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | 2-Hydroxybutyric acid, also known as a-hydroxybutyrate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. 2-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound. |
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Structure | |
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Synonyms | - (RS)-2-Hydroxybutyrate
- (RS)-2-Hydroxybutyric acid
- 1-Hydroxypropane
- 1-Propanol
- 1-Propyl alcohol
- 2-hydroxy-Butanoate
- 2-hydroxy-Butanoic acid
- 2-hydroxy-DL-Butyrate
- 2-hydroxy-DL-Butyric acid
- 2-Hydroxy-n-butyrate
- 2-Hydroxy-n-butyric acid
- 2-Hydroxybutanoate
- 2-Hydroxybutanoic acid
- 2-Hydroxybutyrate
- 2-Hydroxybutyric acid
- a-Hydroxy-n-butyrate
- a-Hydroxy-n-butyric acid
- a-Hydroxybutanoate
- a-Hydroxybutanoic acid
- a-Hydroxybutyrate
- a-Hydroxybutyric acid
- alpha-hydroxy-n-butyrate
- alpha-hydroxy-n-butyric acid
- alpha-Hydroxybutanoate
- alpha-Hydroxybutanoic acid
- alpha-Hydroxybutyrate
- alpha-Hydroxybutyric acid
- Butanoic acid, 2-hydroxy-
- Butyric acid, 2-hydroxy-
- DL-2-Hydroxybutanoate
- DL-2-Hydroxybutanoic acid
- DL-a-Hydroxybutyrate
- DL-a-Hydroxybutyric acid
- DL-alpha-Hydroxybutyrate
- DL-alpha-Hydroxybutyric acid
- Ethylcarbinol
- n-Propan-1-ol
- n-Propanol
- n-Propyl alcohol
- n-Propyl alkohol
- Optal
- Osmosol extra
- Propan-1-ol
- Propanol
- Propanol-1
- Propyl alcohol
- Propylan-propyl alcohol
- Propylic alcohol
- Α-hydroxybutanoate
- Α-hydroxybutanoic acid
- Α-hydroxybutyrate
- Α-hydroxybutyric acid
- 2-Hydroxybutyric acid, (R)-isomer
- 2-Hydroxybutyric acid, monosodium salt
- 2-Hydroxybutyric acid, (+-)-isomer
- 2-Hydroxybutyric acid, monosodium salt, (+-)-isomer
- (+/-)a-hydoxy butyrate
- (+/-)a-hydoxy butyric acid
- (+/-)alpha-hydoxy butyrate
- (+/-)α-hydoxy butyrate
- (+/-)α-hydoxy butyric acid
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CAS number | 71-23-8 |
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Weight | Average: 104.1045 Monoisotopic: 104.047344122 |
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InChI Key | AFENDNXGAFYKQO-UHFFFAOYSA-N |
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InChI | InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) |
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IUPAC Name | 2-hydroxybutanoic acid |
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Traditional IUPAC Name | α-hydroxybutyric acid |
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Chemical Formula | C4H8O3 |
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SMILES | CCC(O)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. |
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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 | Alpha hydroxy acids and derivatives |
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Direct Parent | Alpha hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Fatty acid
- Alpha-hydroxy 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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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 44.2 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)] | PhysProp | LogP | 0.25 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Not Available |
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KEGG Pathways | |
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SMPDB Reactions | Not Available |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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1725 ± 86 µM | YEB media with 0.5 mM glucose | aerobic | Baker's yeast | Experimentally Determined Not Available | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-001j-0900000000-44dd1bf8072e5731bac4 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00e9-9700000000-93eba027d5343e3d6ce1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-001i-1910000000-3bc9898b26df33cad244 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-9000000000-4d935da8e593ec61fd96 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-001j-0900000000-44dd1bf8072e5731bac4 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00e9-9700000000-93eba027d5343e3d6ce1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-1910000000-3bc9898b26df33cad244 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6u-9000000000-0d95c1179b1b00650601 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00v0-9520000000-598a2bd61c303327bd8f | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4j-9200000000-e3b371c29b9ebed3199b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0zfs-9700000000-bccfada2c97e04d34417 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0a4i-9000000000-4d935da8e593ec61fd96 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-0udi-2900000000-3c7915ea71886873f024 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0zfr-7900000000-d91c840306a06d4ea513 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-9500000000-8f04a5941997004743d2 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9100000000-cef703dc6f30af7834a8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-1e7e6e8a895c4c1d51db | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-4900000000-d0907a0b08e0d829ceca | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-9200000000-d826b54f814ac185b4db | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-3727124ed618f038b514 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
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Synthesis Reference: | Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374. |
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