Record Information |
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Version | 2.0 |
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Creation Date | 2012-07-30 14:55:21 -0600 |
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Update Date | 2015-06-03 17:21:11 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | gamma-Hydroxybutyrate |
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Description | Gamma-hydroxybutyrate (GHB) is also known as 4-hydroxybutanoic acid. It is a carboxylic acid with an attached alcohol (hydroxyl) group. GHB can be produced as a result of fermentation, and so is found in small quantities in some beers and wines. (Wikipedia, PMID 15939164) In E. coli, 4-hydroxybutanoate can be produced from the reduction of succinate semialdehyde by the enzyme 4-hydroxybutanoate dehydrogenase. (EcoCyc, PMID: 19372223) |
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Structure | |
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Synonyms: | - γ-hydroxybutyrate
- γ-hydroxybutyric acid
- 3-Carboxypropoxy acid
- 4-Hydroxy-Butanoate
- 4-Hydroxy-Butanoic acid
- 4-Hydroxy-butyrate
- 4-Hydroxy-butyric acid
- 4-Hydroxybutanoate
- 4-Hydroxybutanoic acid
- 4-Hydroxybutyrate
- 4-Hydroxybutyrate monosodium salt
- 4-Hydroxybutyrate sodium
- 4-Hydroxybutyric acid
- 4-Hydroxybutyric acid monosodium salt
- 4-Hydroxybutyric acid sodium
- 4-OH-but
- g Hydroxybutyrate
- g Hydroxybutyric acid
- g-Hydroxy butyrate
- g-Hydroxy butyric acid
- g-Hydroxy sodium butyrate
- g-Hydroxy sodium butyric acid
- G-Hydroxybutyrate
- g-Hydroxybutyrate sodium
- G-Hydroxybutyric acid
- g-Hydroxybutyric acid sodium
- Gamma Hydroxybutyrate
- Gamma Hydroxybutyric Acid
- Gamma-Hydroxy butyrate
- Gamma-Hydroxy butyric acid
- Gamma-Hydroxy sodium butyrate
- Gamma-Hydroxy sodium butyric acid
- Gamma-Hydroxybutyrate
- Gamma-Hydroxybutyrate sodium
- Gamma-Hydroxybutyric acid
- Gamma-Hydroxybutyric acid sodium
- GHB
- Hydroxybutyrate
- Hydroxybutyric acid
- Juice
- Liquid Ecstasy
- Monosodium salt
- Oxy-N-butyrate
- Oxy-N-butyric acid
- Oxybate sodium
- Oxybic acid sodium
- Sodium g-hydroxybutyrate
- Sodium g-hydroxybutyric acid
- Sodium g-oxybutyrate
- Sodium g-oxybutyric acid
- Sodium gamma-hydroxybutyrate
- Sodium gamma-hydroxybutyric acid
- Sodium gamma-oxybutyrate
- Sodium gamma-oxybutyric acid
- Sodium oxybate
- Sodium oxybic acid
- Sodium γ-hydroxybutyrate
- Sodium γ-hydroxybutyric acid
- Sodium γ-oxybutyrate
- Sodium γ-oxybutyric acid
- Xyrem
- γ Hydroxybutyrate
- γ Hydroxybutyric acid
- γ-Hydroxy butyrate
- γ-Hydroxy butyric acid
- γ-Hydroxy sodium butyrate
- γ-Hydroxy sodium butyric acid
- γ-Hydroxybutyrate
- γ-Hydroxybutyrate sodium
- γ-Hydroxybutyric acid
- γ-Hydroxybutyric acid sodium
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Chemical Formula: | C4H8O3 |
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Weight: | Average: 104.1045 Monoisotopic: 104.047344122 |
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InChI Key: | SJZRECIVHVDYJC-UHFFFAOYSA-N |
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InChI: | InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) |
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CAS number: | 591-81-1 |
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IUPAC Name: | 4-hydroxybutanoic acid |
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Traditional IUPAC Name: | gamma hydroxybutyric acid |
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SMILES: | OCCCC(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Hydroxy fatty acids |
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Alternative Parents | |
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Substituents | - Short-chain hydroxy acid
- Hydroxy fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- 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: | -1 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0159-2920000000-131f94186a93d0aa315d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0159-2920000000-131f94186a93d0aa315d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0910000000-7240955b6b16291cf793 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a5c-9000000000-915d32c0dbd6e6d19a55 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00di-9610000000-52e5254f6eba257ad184 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - QqQ 10V, positive | splash10-14ii-9400000000-77378d9d837f1823ed37 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, negative | splash10-0udi-0900000000-ca02549abb7c7402b481 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-0udi-0900000000-942af3cd327a2dd39887 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-0udi-1900000000-671c45f3bda2eabba3c1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-0udi-1900000000-36fabc35679210a4621a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-0udi-2900000000-146b4ca6698f6c40d476 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-0udi-4900000000-32e86ae76401d830a8a1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-0udi-8900000000-07fc17585cf5e8d2ba9b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0pbi-9400000000-70777a3c6521e72b59b4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 7V, negative | splash10-0a4i-9000000000-cad0cc415c906a783cfc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0zg0-9500000000-9dfcd62aeff3ff1e731d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0pb9-9300000000-0e1b3056ef85c0fbe59d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0a4i-9200000000-144d4f05dfc0b2dbd827 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-0a4i-9100000000-5a807248d180fcc738ee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-0a4i-9000000000-aeb70e18a8467ef1b4b1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-0a4i-9000000000-50691ede3dffed6a4afb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, negative | splash10-0a4i-9000000000-13adfaf490932a7c0fb9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 7V, negative | splash10-000i-9000000000-3051dc4fe82b4abf5478 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 0V, positive | splash10-0002-0900000000-8f691ae372d6f1d18226 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9100000000-80636ab7e3cb47d4d58f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05n4-9000000000-71899633e269029ab7f9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-910235f5bc92bcca7469 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-8900000000-5890f0a527dd16d9ac75 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0k9i-9200000000-241210fedf9304168090 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-21d09118dfcfcb093f8d | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0006-9000000000-d55d971a361b41564681 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. Pubmed: 3126356
- Elliott, S., Burgess, V. (2005). "The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages." Forensic Sci Int 151:289-292. Pubmed: 15939164
- Ergezinger K, Jeschke R, Frauendienst-Egger G, Korall H, Gibson KM, Schuster VH: Monitoring of 4-hydroxybutyric acid levels in body fluids during vigabatrin treatment in succinic semialdehyde dehydrogenase deficiency. Ann Neurol. 2003 Nov;54(5):686-9. Pubmed: 14595661
- Gibson KM, Aramaki S, Sweetman L, Nyhan WL, DeVivo DC, Hodson AK, Jakobs C: Stable isotope dilution analysis of 4-hydroxybutyric acid: an accurate method for quantification in physiological fluids and the prenatal diagnosis of 4-hydroxybutyric aciduria. Biomed Environ Mass Spectrom. 1990 Feb;19(2):89-93. Pubmed: 2407302
- Gibson KM, Baumann C, Ogier H, Rossier E, Vollmer B, Jakobs C: Pre- and postnatal diagnosis of succinic semialdehyde dehydrogenase deficiency using enzyme and metabolite assays. J Inherit Metab Dis. 1994;17(6):732-7. Pubmed: 7707697
- Kankaanpaa A, Liukkonen R, Ariniemi K: Determination of gamma-hydroxybutyrate (GHB) and its precursors in blood and urine samples: a salting-out approach. Forensic Sci Int. 2007 Aug 6;170(2-3):133-8. Epub 2007 Jul 20. Pubmed: 17658710
- LeBeau MA, Montgomery MA, Morris-Kukoski C, Schaff JE, Deakin A, Levine B: A comprehensive study on the variations in urinary concentrations of endogenous gamma-hydroxybutyrate (GHB). J Anal Toxicol. 2006 Mar;30(2):98-105. Pubmed: 16620539
- Saito, N., Robert, M., Kochi, H., Matsuo, G., Kakazu, Y., Soga, T., Tomita, M. (2009). "Metabolite profiling reveals YihU as a novel hydroxybutyrate dehydrogenase for alternative succinic semialdehyde metabolism in Escherichia coli." J Biol Chem 284:16442-16451. Pubmed: 19372223
- Shinka T, Inoue Y, Ohse M, Ito A, Ohfu M, Hirose S, Kuhara T: Rapid and sensitive detection of urinary 4-hydroxybutyric acid and its related compounds by gas chromatography-mass spectrometry in a patient with succinic semialdehyde dehydrogenase deficiency. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 25;776(1):57-63. Pubmed: 12127325
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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