Record Information |
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Version | 2.0 |
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Creation Date | 2012-08-09 09:16:12 -0600 |
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Update Date | 2015-09-13 15:15:33 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Glutaric acid |
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Description | Glutaric acid is a simple five-carbon linear dicarboxylic acid. It is a substrate inhibitor for glutamate decarboxylase. In many organisms it is involved in lysine degradation. |
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Structure | |
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Synonyms: | - 1,3-Propanedicarboxylate
- 1,3-Propanedicarboxylic acid
- 1,5-Pentanedioate
- 1,5-Pentanedioic acid
- Glutarate
- Pentandioate
- Pentandioic acid
- Pentanedioate
- Pentanedioic acid
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Chemical Formula: | C5H8O4 |
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Weight: | Average: 132.1146 Monoisotopic: 132.042258744 |
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InChI Key: | JFCQEDHGNNZCLN-UHFFFAOYSA-N |
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InChI: | InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) |
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CAS number: | 110-94-1 |
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IUPAC Name: | pentanedioic acid |
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Traditional IUPAC Name: | glutaric acid |
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SMILES: | OC(=O)CCCC(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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: | -2 |
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Melting point: | 95.8 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 1600.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP: | -0.29 [HANSCH,C ET AL. (1995)] | 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: | |
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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) (2 TMS) | splash10-0f6t-2940000000-9f099473c4a6eb94d4be | 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) | splash10-0002-1920000000-4ade63738a1c00460a63 | 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) | splash10-0002-1910000000-743df9571fee7baa3417 | 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) | splash10-00fs-9710000000-ba958e52b1424e5d4840 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0cgj-3930000000-298fe512c6b58220ee33 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052o-9000000000-663deab1ce6413c4859d | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-0920000000-56bce366cac24cd6773f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0f6t-2940000000-9f099473c4a6eb94d4be | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-1920000000-4ade63738a1c00460a63 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-1910000000-743df9571fee7baa3417 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00fs-9710000000-ba958e52b1424e5d4840 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0cgj-3930000000-298fe512c6b58220ee33 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0910000000-86fbcf8f1c72fbb2ffd0 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01q3-9200000000-fcbc36fd55a7945d3f25 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-05g3-9610000000-07394eb05b518a4e3bf4 | 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 (TMS_1_1) - 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_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-0019-9500000000-9db56ca3a541f0ce07d1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-052r-9100000000-991f69d0892976558f85 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0536-9300000000-20fb2c8dd136e4924aca | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-001i-0900000000-8eb90c15915f014713ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9200000000-2ffdc08c49952e135a86 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-8884b857c9582288f35a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-052f-9000000000-7d2c0333bdce4dbabbc6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-9ab2a948083302641628 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-000i-9400000000-c5ec3115706f6041b868 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-001i-0900000000-8eb90c15915f014713ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9200000000-2ffdc08c49952e135a86 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-8884b857c9582288f35a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-052f-9000000000-7d2c0333bdce4dbabbc6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-9ab2a948083302641628 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-9400000000-c5ec3115706f6041b868 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-9000000000-89029b221f83859b721c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-014r-9000000000-ec63d377e53acd0b3f82 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-9000000000-1778c9be6683c7aaea83 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 6V, Negative | splash10-001r-7900000000-88fa19a8b55a2221ac33 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-64994bb5102d568ae3ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9300000000-087a8bb0014a4b98f216 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9100000000-be7bb3a98fa2fe29624c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-ee7e50d3e19afde6d997 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-052o-9000000000-663deab1ce6413c4859d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-1900000000-2ccd8e2a515cf328e787 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-052o-9000000000-f308daa4e82c16019e0d | View in MoNA |
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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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1D NMR | 13C 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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References: | - Baric I, Wagner L, Feyh P, Liesert M, Buckel W, Hoffmann GF: Sensitivity and specificity of free and total glutaric acid and 3-hydroxyglutaric acid measurements by stable-isotope dilution assays for the diagnosis of glutaric aciduria type I. J Inherit Metab Dis. 1999 Dec;22(8):867-81. Pubmed: 10604139
- Bishop FS, Liu JK, McCall TD, Brockmeyer DL: Glutaric aciduria type 1 presenting as bilateral subdural hematomas mimicking nonaccidental trauma. Case report and review of the literature. J Neurosurg. 2007 Mar;106(3 Suppl):222-6. Pubmed: 17465389
- Goodman SI, Gallegos DA, Pullin CJ, Halpern B, Truscott RJ, Wise G, Wilcken B, Ryan ED, Whelen DT: Antenatal diagnosis of glutaric acidemia. Am J Hum Genet. 1980 Sep;32(5):695-9. Pubmed: 6893520
- Goodman SI, Stein DE, Schlesinger S, Christensen E, Schwartz M, Greenberg CR, Elpeleg ON: Glutaryl-CoA dehydrogenase mutations in glutaric acidemia (type I): review and report of thirty novel mutations. Hum Mutat. 1998;12(3):141-4. Pubmed: 9711871
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
- 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
- Hoffmann GF, Trefz FK, Barth PG, Bohles HJ, Biggemann B, Bremer HJ, Christensen E, Frosch M, Hanefeld F, Hunneman DH, et al.: Glutaryl-coenzyme A dehydrogenase deficiency: a distinct encephalopathy. Pediatrics. 1991 Dec;88(6):1194-203. Pubmed: 1956737
- Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7. Pubmed: 6698061
- Muller E, Kolker S: Reduction of lysine intake while avoiding malnutrition--major goals and major problems in dietary treatment of glutaryl-CoA dehydrogenase deficiency. J Inherit Metab Dis. 2004;27(6):903-10. Pubmed: 15505398
- 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
- Singh I: Biochemistry of peroxisomes in health and disease. Mol Cell Biochem. 1997 Feb;167(1-2):1-29. Pubmed: 9059978
- 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. Pubmed: 19212411
- 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
- Whelan DT, Hill R, Ryan ED, Spate M: L-Glutaric acidemia: investigation of a patient and his family. Pediatrics. 1979 Jan;63(1):88-93. Pubmed: 440804
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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Synthesis Reference: | Petrova, E. G.; Kasumova, N. M.; Kagramanova, N. A.; Dadasheva, A. D. Mechanism of glutaric acid synthesis. Issledovaniya v Oblasti Kinetiki, Modelirovaniya i Optimizatsii Khimicheskikh Protsessov (1974), 2 277-89. |
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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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