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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-07-23 05:43:49 UTC |
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HMDB ID | HMDB0000008 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Hydroxybutyric acid |
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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 ). |
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Structure | |
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Synonyms | Value | Source |
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2-Hydroxybutanoic acid | ChEBI | alpha-Hydroxybutanoic acid | ChEBI | alpha-Hydroxybutyric acid | ChEBI | 2-Hydroxybutanoate | Generator | a-Hydroxybutanoate | Generator | a-Hydroxybutanoic acid | Generator | alpha-Hydroxybutanoate | Generator | Α-hydroxybutanoate | Generator | Α-hydroxybutanoic acid | Generator | a-Hydroxybutyrate | Generator | a-Hydroxybutyric acid | Generator | alpha-Hydroxybutyrate | Generator | Α-hydroxybutyrate | Generator | Α-hydroxybutyric acid | Generator | 2-Hydroxybutyrate | Generator | (RS)-2-Hydroxybutyrate | HMDB | (RS)-2-Hydroxybutyric acid | HMDB | 2-Hydroxy-butanoate | HMDB | 2-Hydroxy-butanoic acid | HMDB | 2-Hydroxy-DL-butyrate | HMDB | 2-Hydroxy-DL-butyric acid | HMDB | 2-Hydroxy-N-butyrate | HMDB | 2-Hydroxy-N-butyric acid | HMDB | a-Hydroxy-N-butyrate | HMDB | a-Hydroxy-N-butyric acid | HMDB | alpha-Hydroxy-N-butyrate | HMDB | alpha-Hydroxy-N-butyric acid | HMDB | DL-2-Hydroxybutanoate | HMDB | DL-2-Hydroxybutanoic acid | HMDB | DL-a-Hydroxybutyrate | HMDB | DL-a-Hydroxybutyric acid | HMDB | DL-alpha-Hydroxybutyrate | HMDB | DL-alpha-Hydroxybutyric acid | HMDB | 2-Hydroxybutyric acid, (R)-isomer | HMDB | 2-Hydroxybutyric acid, monosodium salt | HMDB | 2-Hydroxybutyric acid, (+-)-isomer | HMDB | 2-Hydroxybutyric acid, monosodium salt, (+-)-isomer | HMDB | (+/-)a-hydoxy butyrate | HMDB | (+/-)a-hydoxy butyric acid | HMDB | (+/-)alpha-hydoxy butyrate | HMDB | (+/-)α-hydoxy butyrate | HMDB | (+/-)α-hydoxy butyric acid | HMDB | 2-Hydroxybutyric acid | MeSH |
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Chemical Formula | C4H8O3 |
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Average Molecular Weight | 104.1045 |
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Monoisotopic Molecular Weight | 104.047344122 |
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IUPAC Name | 2-hydroxybutanoic acid |
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Traditional Name | α-hydroxybutyric acid |
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CAS Registry Number | 600-15-7 |
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SMILES | CCC(O)C(O)=O |
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InChI Identifier | InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) |
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InChI Key | AFENDNXGAFYKQO-UHFFFAOYSA-N |
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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 44.2 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| 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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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Sweat
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 8.00-80.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 26.9(32.92) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 8.00-80.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Blood | Detected but not Quantified | | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 54.0 (8.0-80.0) uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 40.0 +/- 24.0 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 85.0 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 37 +/- 21 (10 - 76) uM | Children (1-13 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 35.0 +/- 24.0 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 10.42 +/- 9.20 uM | Adult (>18 years old) | Female | Normal | | details | Sweat | Detected but not Quantified | | Adult | Both | Normal | | details | Urine | Detected and Quantified | 0.31-0.69 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 2.445 (0-4.89) umol/mmol creatinine | Not Specified | Both | Normal | | details | Urine | Detected and Quantified | 3.29 +/- 3.529 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 2.8 (1.2-6.9) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 5.0 (0.0-10.0) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.26-0.53 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 26.96 +/- 13.11 uM | Adult (>18 years old) | Female | Pregnancy with fetuses with trisomy 18 | | details | Blood | Detected and Quantified | 16.93 +/- 8.17 uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 21.4 (5.6) uM | Adult (>18 years old) | Female | Early preeclampsia | | details | Blood | Detected and Quantified | 19.5 (7.4) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Blood | Detected and Quantified | 17.13 (7.48) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 16.69 (6.25) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 28.0 (14.4) uM | Adult (>18 years old) | Female | Late-onset preeclampsia | | details | Blood | Detected and Quantified | 4.14(10.18) uM | Adult (>18 years old) | Both | Heart failure with reduced ejection fraction | | details | Blood | Detected and Quantified | 21.2 (7.5) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Schizophrenia | | details | Blood | Detected and Quantified | 23.1 (14.1) uM | Adult (>18 years old) | Female | Down syndrome pregnancy | | details | Blood | Detected and Quantified | 15.0 (7.4) uM | Adult (>18 years old) | Female | Pregnancy | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Saliva | Detected and Quantified | 7.26 +/- 4.47 uM | Adult (>18 years old) | Male | Alzheimer's disease | | details | Saliva | Detected and Quantified | 7.30 +/- 1.32 uM | Adult (>18 years old) | Male | Frontotemporal lobe dementia | | details | Saliva | Detected and Quantified | 8.12 +/- 5.32 uM | Adult (>18 years old) | Both | Lewy body disease | | details | Urine | Detected and Quantified | >25.0 umol/mmol creatinine | Adult (>18 years old) | Both | Pyruvate dehydrogenase deficiency | | details | Urine | Detected and Quantified | 8.699 +/- 10.366 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Schizophrenia | | details | Urine | Detected and Quantified | 248.732 umol/mmol creatinine | Infant (0-1 year old) | Male | Dihydrolipoamide Dehydrogenase Deficiency | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal adenoma | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Schizophrenia |
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- Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
| Early preeclampsia |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
| Pregnancy |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
- Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Late-onset preeclampsia |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
| Alzheimer's disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Frontotemporal dementia |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Lewy body disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Pyruvate dehydrogenase deficiency |
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- (). OMIM 238331. .
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
| Dihydrolipoamide Dehydrogenase Deficiency |
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- Kuhara T, Shinka T, Inoue Y, Matsumoto M, Yoshino M, Sakaguchi Y, Matsumoto I: Studies of urinary organic acid profiles of a patient with dihydrolipoyl dehydrogenase deficiency. Clin Chim Acta. 1983 Sep 30;133(2):133-40. [PubMed:6688766 ]
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Associated OMIM IDs | - 114500 (Colorectal cancer)
- 181500 (Schizophrenia)
- 104300 (Alzheimer's disease)
- 600274 (Frontotemporal dementia)
- 312170 (Pyruvate dehydrogenase deficiency)
- 610247 (Eosinophilic esophagitis)
- 246900 (Dihydrolipoamide Dehydrogenase Deficiency)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB021867 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 10792 |
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KEGG Compound ID | C05984 |
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BioCyc ID | Not Available |
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BiGG ID | 47130 |
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Wikipedia Link | 2-Hydroxybutyric_acid |
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METLIN ID | 3783 |
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PubChem Compound | 11266 |
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PDB ID | Not Available |
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ChEBI ID | 1148 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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References |
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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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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. [PubMed:8257730 ]
- 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 ]
- (). Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 548D. .
- (). Mori, K. et al., Tetrahedron, 1979, 35, 1601. .
- (). Levene, P.A. et al., J. Biol. Chem., 1941, 141, 391. .
- (). Duvillier, E., Ann. Chim. Phys., 1879, 17, 532. .
- (). Chenault, H.K. et al., J.O.C., 1987, 52, 2608. .
- (). Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 854B. .
- (). Horn, D.H.S. et al., J.C.S., 1954, 1460. .
- (). Wong, C.H. et al., J.O.C., 1985, 50, 1992. .
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