|Created at||2005-11-16 15:48:42 UTC|
|Updated at||2022-01-17 18:53:24 UTC|
| NP-MRD ID||NP0000052|
|Secondary Accession Numbers||None|
|Natural Product Identification|
|Common Name||2-Hydroxybutyric acid|
|Description||2-Hydroxybutyric acid (alpha-hydroxybutyrate) is an organic acid derived from alpha-ketobutyrate. Alpha-Ketobutyrate is produced by amino acid catabolism (threonine and methionine) and glutathione anabolism (cysteine formation pathway) and is metabolized to propionyl-CoA and carbon dioxide (PMID: 20526369 ). 2-Hydroxybutyric acid is formed as a by-product of the formation of alpha-ketobutyrate via a reaction catalyzed by lactate dehydrogenase (LDH) or alpha-hydroxybutyrate dehydrogenase (alphaHBDH). Alpha-Hydroxybutyric acid is primarily produced in mammalian hepatic tissues that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification of xenobiotics in the liver can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway (which forms methionine) into the transsulfuration pathway (which forms cystathionine). 2-Hydroxybutyrate is released as a byproduct when cystathionine is cleaved into cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate. 2-Hydroxybutyrate is an early marker for both insulin resistance and impaired glucose regulation that appears to arise due to increased lipid oxidation and oxidative stress (PMID: 20526369 ). 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.G. Birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early-stage type II diabetes (PMID: 19166731 ). It was concluded from studies done in the mid-1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydroxybutyric acid (PMID: 168632 ).|
|Average Mass||104.1045 Da|
|Monoisotopic Mass||104.04734 Da|
|IUPAC Name||(2S)-2-hydroxybutanoic acid|
|Traditional Name||(S)-2-hydroxybutyric acid|
|CAS Registry Number||600-15-7|
|Spectrum Type||Description||Depositor ID||Depositor Organization||Depositor||Deposition Date||View|
|1D NMR||1H NMR Spectrum (1D, 700 MHz, H2O, simulated)||Ahselim||2022-01-17||View Spectrum|
|1D NMR||1H NMR Spectrum (1D, 700 MHz, H2O, experimental)||Ahselim||2022-01-17||View Spectrum|
|1D NMR||1H NMR Spectrum (1D, 600 MHz, H2O, experimental)||Wishart Lab||Wishart Lab||David Wishart||2021-06-20||View Spectrum|
|2D NMR||[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)||Wishart Lab||Wishart Lab||David Wishart||2021-06-20||View Spectrum|
|Chemical Shift Submissions|
|Species of Origin|
|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.|
|Kingdom||Organic compounds |
|Super Class||Organic acids and derivatives |
|Class||Hydroxy acids and derivatives |
|Sub Class||Alpha hydroxy acids and derivatives |
|Direct Parent||Alpha hydroxy acids and derivatives |
- 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
- Aliphatic acyclic compound
|Molecular Framework||Aliphatic acyclic compounds|
|Melting Point||44.2 °C||Not Available|
|Boiling Point||118-120 °C||Not Available|
|Water Solubility||Not Available||Not Available|
|LogP||Not Available||Not Available|
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- Landaas S, Pettersen JE: Clinical conditions associated with urinary excretion of 2-hydroxybutyric acid. Scand J Clin Lab Invest. 1975 May;35(3):259-66. [PubMed:168632 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Li X, Xu Z, Lu X, Yang X, Yin P, Kong H, Yu Y, Xu G: Comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry for metabonomics: Biomarker discovery for diabetes mellitus. Anal Chim Acta. 2009 Feb 9;633(2):257-62. doi: 10.1016/j.aca.2008.11.058. Epub 2008 Dec 3. [PubMed:19166731 ]
- Gall WE, Beebe K, Lawton KA, Adam KP, Mitchell MW, Nakhle PJ, Ryals JA, Milburn MV, Nannipieri M, Camastra S, Natali A, Ferrannini E: alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population. PLoS One. 2010 May 28;5(5):e10883. doi: 10.1371/journal.pone.0010883. [PubMed:20526369 ]
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