| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-08-09 09:16:11 -0600 |
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| Update Date | 2015-09-13 12:56:16 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | 3-Hydroxybutyric acid |
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| Description | 3-Hydroxybutyric acid or beta-hydroxybutyrate belongs to a group of compounds known as ketone bodies. Other ketone bodies include acetoacetate and acetone. 3-hydroxybutyric acid is chiral and so it has 2 enantiomeric forms. (Wikipedia) In some strains of E. coli, such as E. coli O8 IAI1, the enzyme 3-hydroxybutyrate dehydrogenase (EC:1.1.1.30) catalyzes a reversible redox reaction that converts 3-hydroxybutyric acid to acetoacetate, which can then be converted into acetoacetyl-CoA and participate in fatty acid metabolism. (KEGG). Hydroxybutyrate can also serve as a substrate for short-chain acylCo-A ligase and become a precursor for lipid synthesis. |
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| Structure | |
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| Synonyms: | - β-hydroxybutyrate
- β-hydroxybutyric acid
- (R)-3-Hydroxybutanoate
- (R)-3-hydroxybutanoic acid
- (R)-3-Hydroxybutyrate
- (R)-3-hydroxybutyric acid
- 3-hydroxy-butanoate
- 3-hydroxy-butanoic acid
- 3-hydroxy-butyrate
- 3-hydroxy-butyric acid
- 3-Hydroxybutanoate
- 3-Hydroxybutanoic acid
- 3-Hydroxybutyrate
- 3-OH-Butyrate
- 3-OH-butyric acid
- B-Hydroxy-n-butyrate
- B-Hydroxy-n-butyric acid
- B-Hydroxybutanoate
- B-Hydroxybutanoic acid
- b-Hydroxybuttersaeure
- B-Hydroxybutyrate
- B-hydroxybutyric acid
- Beta-Hydroxy-n-butyrate
- Beta-Hydroxy-n-butyric acid
- Beta-Hydroxybutanoate
- Beta-Hydroxybutanoic acid
- Beta-Hydroxybuttersaeure
- Beta-Hydroxybutyrate
- Beta-Hydroxybutyric acid
- Biopol
- D-β-hydroxybutyrate
- D-β-hydroxybutyric acid
- D-3-hydroxybutyrate
- D-3-Hydroxybutyric acid
- DL-3-Hydroxybutyrate
- DL-3-Hydroxybutyric acid
- DL-b-Hydroxybutyrate
- DL-b-Hydroxybutyric acid
- DL-beta-Hydroxybutyrate
- DL-beta-Hydroxybutyric acid
- DL-β-Hydroxybutyrate
- DL-β-Hydroxybutyric acid
- β-Hydroxy-N-butyrate
- β-Hydroxy-N-butyric acid
- β-Hydroxybutanoate
- β-Hydroxybutanoic acid
- β-Hydroxybuttersaeure
- β-Hydroxybutyrate
- β-Hydroxybutyric acid
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| Chemical Formula: | C4H8O3 |
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| Weight: | Average: 104.1045
Monoisotopic: 104.047344122 |
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| InChI Key: | WHBMMWSBFZVSSR-UHFFFAOYSA-N |
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| InChI: | InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) |
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| CAS number: | 300-85-6 |
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| IUPAC Name: | 3-hydroxybutanoic acid |
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| Traditional IUPAC Name: | 3 hydroxybutyrate |
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| SMILES: | CC(O)CC(O)=O |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State: | Solid |
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| Charge: | -1 |
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| Melting point: | 46 °C |
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| Experimental Properties: | | Property | Value | Source |
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| Water Solubility: | 444 mg/mL [HMP experimental] | PhysProp |
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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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0900000000-92be5c49a099fe1d9865 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-01ot-1920000000-c93138bf9d35643fef30 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00dj-8900000000-e632e14fb4be28bdb786 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-014l-1900000000-e192caba63f034040624 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-92be5c49a099fe1d9865 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-01ot-1920000000-c93138bf9d35643fef30 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00dj-8900000000-e632e14fb4be28bdb786 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014l-1900000000-e192caba63f034040624 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-d06c5ac1a3733a38ea05 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-9000000000-63f261a4dc876e264246 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-01ei-9710000000-2652bd46b41e50defdb0 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0a4i-9200000000-4156904e7472b5e97249 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-9300000000-505ae46abb0c49c78b1e | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0zfr-9600000000-dfed69c37c1a4d794440 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0zfr-4900000000-537084557f5986f16b31 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0zfr-4900000000-537084557f5986f16b31 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-000i-9000000000-7f0ec480b3c3c3911acd | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-9100000000-05c4623b015ff4300a6d | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05n0-9000000000-cbe0653845ffe4dc6ad4 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-e55d47308c7464e4cb22 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0zfr-8900000000-06dfbf939f6d19983ebe | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-9200000000-48b6e9b8656d41bff9cf | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-f7d61596ff4428fe6b09 | View in MoNA |
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| MS | Mass Spectrum (Electron Ionization) | splash10-0007-9000000000-7fc414806153ebd8822c | 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 | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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| References |
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- Blomqvist G, Alvarsson M, Grill V, Von Heijne G, Ingvar M, Thorell JO, Stone-Elander S, Widen L, Ekberg K: Effect of acute hyperketonemia on the cerebral uptake of ketone bodies in nondiabetic subjects and IDDM patients. Am J Physiol Endocrinol Metab. 2002 Jul;283(1):E20-8. Pubmed: 12067838
- Frenkel G, Peterson RN, Freund M: Oxidative and glycolytic metabolism of semen components by washed guinea pig spermatozoa. Fertil Steril. 1975 Feb;26(2):144-7. Pubmed: 1126459
- Geary N, Grotschel H, Scharrer E: Blood metabolites and feeding during postinsulin hypophagia. Am J Physiol. 1982 Sep;243(3):R304-11. Pubmed: 7051864
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
- Kamijo T, Indo Y, Souri M, Aoyama T, Hara T, Yamamoto S, Ushikubo S, Rinaldo P, Matsuda I, Komiyama A, Hashimoto T: Medium chain 3-ketoacyl-coenzyme A thiolase deficiency: a new disorder of mitochondrial fatty acid beta-oxidation. Pediatr Res. 1997 Nov;42(5):569-76. Pubmed: 9357925
- Krotkiewski M: Value of VLCD supplementation with medium chain triglycerides. Int J Obes Relat Metab Disord. 2001 Sep;25(9):1393-400. Pubmed: 11571605
- Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. Pubmed: 15363641
- Pan JW, Rothman TL, Behar KL, Stein DT, Hetherington HP: Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis. J Cereb Blood Flow Metab. 2000 Oct;20(10):1502-7. Pubmed: 11043913
- Pan JW, Telang FW, Lee JH, de Graaf RA, Rothman DL, Stein DT, Hetherington HP: Measurement of beta-hydroxybutyrate in acute hyperketonemia in human brain. J Neurochem. 2001 Nov;79(3):539-44. Pubmed: 11701757
- Plecko B, Stoeckler-Ipsiroglu S, Schober E, Harrer G, Mlynarik V, Gruber S, Moser E, Moeslinger D, Silgoner H, Ipsiroglu O: Oral beta-hydroxybutyrate supplementation in two patients with hyperinsulinemic hypoglycemia: monitoring of beta-hydroxybutyrate levels in blood and cerebrospinal fluid, and in the brain by in vivo magnetic resonance spectroscopy. Pediatr Res. 2002 Aug;52(2):301-6. Pubmed: 12149510
- Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
- Teresinski G, Buszewicz G, Madro R: The influence of ethanol on the level of ketone bodies in hypothermia. Forensic Sci Int. 2002 Jun 25;127(1-2):88-96. Pubmed: 12098531
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
- Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. Pubmed: 3884391
- Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834
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| Synthesis Reference: | Not Available |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| Links |
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| External Links: | |
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