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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 | 2020-02-26 21:22:19 UTC |
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HMDB ID | HMDB0000549 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | gamma-Butyrolactone |
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Description | gamma-Butyrolactone, also known as 1,4-butanolide or 1,4-lactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, gamma-butyrolactone is considered to be a fatty ester lipid molecule. gamma-Butyrolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Butyrolactone exists in all living species, ranging from bacteria to humans. gamma-Butyrolactone is a sweet, caramel, and creamy tasting compound. Outside of the human body, gamma-Butyrolactone has been detected, but not quantified in, several different foods, such as pepper (c. annuum), yellow bell peppers, orange bell peppers, soy beans, and evergreen blackberries. This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. Hypothermia has been reported in adults and children following exposure (T36). gamma-Butyrolactone is a potentially toxic compound. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent. One of the FURANS with a carbonyl thereby forming a cyclic lactone. |
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Structure | |
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Synonyms | Value | Source |
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1,2-Butanolide | ChEBI | 1,4-Butanolide | ChEBI | 1,4-Lactone | ChEBI | 4-Butyrolactone | ChEBI | 4-Deoxytetronic acid | ChEBI | 4-Hydroxybutyric acid lactone | ChEBI | Butyrolactone | ChEBI | Dihydro-2(3H)-furanone | ChEBI | gamma-Butanolactone | ChEBI | gamma-Hydroxybutyric acid lactone | ChEBI | gamma-Hydroxybutyrolactone | ChEBI | Tetrahydrofuran-2-one | ChEBI | 4-Deoxytetronate | Generator | 4-Hydroxybutyrate lactone | Generator | g-Butanolactone | Generator | Γ-butanolactone | Generator | g-Hydroxybutyrate lactone | Generator | g-Hydroxybutyric acid lactone | Generator | gamma-Hydroxybutyrate lactone | Generator | Γ-hydroxybutyrate lactone | Generator | Γ-hydroxybutyric acid lactone | Generator | g-Hydroxybutyrolactone | Generator | Γ-hydroxybutyrolactone | Generator | g-Butyrolactone | Generator | Γ-butyrolactone | Generator | 1-Oxacyclopentan-2-one | HMDB | 2,3,4,5-Tetrahydro-2-furanone | HMDB | 2-Oxolanone | HMDB | 2-Oxotetrahydrofuran | HMDB | 4,5-Dihydro-2(3H)-furanone | HMDB | 4-Butanolide | HMDB | 4-Hydroxy-butanoate | HMDB | 4-Hydroxy-butanoic acid | HMDB | 4-Hydroxy-butanoic acid g-lactone | HMDB | 4-Hydroxybutanoate | HMDB | 4-Hydroxybutanoic acid | HMDB | 4-Hydroxybutanoic acid lactone | HMDB | Butyric acid lactone | HMDB | g-Butalactone | HMDB | g-Butyryllactone | HMDB | gamma-Butalactone | HMDB | gamma-Butyryllactone | HMDB | GBL | HMDB | Paint clean g | HMDB | Tetrahydro-2-furanone | HMDB | 4 Butyrolactone | HMDB | gamma Butyrolactone | HMDB | Furanone, tetrahydro 2 | HMDB | 1,4 Butanolide | HMDB | 4 Hydroxybutyric acid lactone | HMDB | Lactone, 4-hydroxybutyric acid | HMDB | gamma-Butyrolactone | MeSH |
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Chemical Formula | C4H6O2 |
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Average Molecular Weight | 86.0892 |
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Monoisotopic Molecular Weight | 86.036779436 |
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IUPAC Name | oxolan-2-one |
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Traditional Name | butyrolactone |
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CAS Registry Number | 96-48-0 |
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SMILES | O=C1CCCO1 |
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InChI Identifier | InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 |
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InChI Key | YEJRWHAVMIAJKC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactones |
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Sub Class | Gamma butyrolactones |
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Direct Parent | Gamma butyrolactones |
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Alternative Parents | |
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Substituents | - Gamma butyrolactone
- Tetrahydrofuran
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Industrial application: |
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Physical Properties |
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State | Liquid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | -45 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000 mg/mL | Not Available | LogP | -0.64 | HANSCH,C ET AL. (1995) |
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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 - EI-B (Non-derivatized) | splash10-004l-9000000000-500445dc73cb69119e6b | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-002f-9000000000-d3df175d3315ed446e14 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004l-9000000000-500445dc73cb69119e6b | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-002f-9000000000-d3df175d3315ed446e14 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-9000000000-bd4b413f20907d13a107 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9000000000-4a6de93563809aa51a33 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9000000000-4a6de93563809aa51a33 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-b5163f6eb1e8004e61a9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-004l-9000000000-1066d349a6023c66dd64 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-002f-9000000000-d3df175d3315ed446e14 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9000000000-507998514018a44c4cf0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000l-9000000000-d4ec4947321dfb11fab4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-b2a1436205f5365513b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-fb7c9ada825a0c62979f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000l-9000000000-95fda8a898d02f7e71ff | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-9000000000-c8282365f175b61ca8c0 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-004l-9000000000-2fc3f4165b5808b41e93 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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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 | 0.28 +/- 0.16 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB04699 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003392 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7029 |
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KEGG Compound ID | C01770 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Gamma-Butyrolactone |
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METLIN ID | 5533 |
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PubChem Compound | 7302 |
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PDB ID | Not Available |
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ChEBI ID | 42639 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Zhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang. Process for preparation of g-butyrolactone with high yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 13 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Fukui Y, Matsusima E, Muramoto K, Nagai N, Ohama K, Yamashita K: Validation of a simple gas chromatographic-mass spectrometric method for the determination of gamma-butyrolactone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):73-80. [PubMed:12535840 ]
- Thupari JN, Landree LE, Ronnett GV, Kuhajda FP: C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9498-502. Epub 2002 Jun 11. [PubMed:12060712 ]
- Wood M, Laloup M, Samyn N, Morris MR, de Bruijn EA, Maes RA, Young MS, Maes V, De Boeck G: Simultaneous analysis of gamma-hydroxybutyric acid and its precursors in urine using liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2004 Nov 12;1056(1-2):83-90. [PubMed:15595536 ]
- Quintanilla RA, Orellana DI, Gonzalez-Billault C, Maccioni RB: Interleukin-6 induces Alzheimer-type phosphorylation of tau protein by deregulating the cdk5/p35 pathway. Exp Cell Res. 2004 Apr 15;295(1):245-57. [PubMed:15051507 ]
- Knust U, Hull WE, Spiegelhalder B, Bartsch H, Strowitzki T, Owen RW: Analysis of enterolignan glucuronides in serum and urine by HPLC-ESI-MS. Food Chem Toxicol. 2006 Jul;44(7):1038-49. Epub 2006 Feb 20. [PubMed:16488523 ]
- Selmaoui B, Aymard N, Lambrozo J, Touitou Y: Evaluation of the nocturnal levels of urinary biogenic amines in men exposed overnight to 50-Hz magnetic field. Life Sci. 2003 Oct 31;73(24):3073-82. [PubMed:14550848 ]
- Oshima I, Saito S, Shiota K, Miyake A, Oka Y, Nakayama R: Kinetic study on disappearance of gamma-butyrolactone-gamma-carbonyl-L-histidyl-L-prolinamide (DN-1417) from plasma using a radioimmunoassay for DN-1417 isobutylamide. J Pharmacobiodyn. 1983 Mar;6(3):202-8. [PubMed:6410041 ]
- Yeatman DT, Reid K: A study of urinary endogenous gamma-hydroxybutyrate (GHB) levels. J Anal Toxicol. 2003 Jan-Feb;27(1):40-2. [PubMed:12587682 ]
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