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Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-13 11:52:01 UTC |
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Update Date | 2023-02-21 17:29:05 UTC |
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HMDB ID | HMDB0041992 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pivalic acid |
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Description | Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. Relative to esters of most carboxylic acids, esters of pivalic acid are unusually resistant to hydrolysis. Some applications result from this thermal stability. Polymers derived from pivalate esters of vinyl alcohol are highly reflective lacquers. The pivaloyl (abbreviated piv or pv) group is a protective group for alcohols in organic synthesis. |
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Structure | InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7) |
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Synonyms | Value | Source |
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2,2-Dimethylpropionic acid | ChEBI | Acide 2,2-dimethylpropanoique | ChEBI | Acide pivalique | ChEBI | Acido pivalico | ChEBI | alpha,alpha-Dimethylpropionic acid | ChEBI | Dimethylpropionic acid | ChEBI | Neopentanoic acid | ChEBI | Pivalinsaeure | ChEBI | Tert-pentanoic acid | ChEBI | Trimethylacetic acid | ChEBI | 2,2-Dimethylpropionate | Generator | a,a-Dimethylpropionate | Generator | a,a-Dimethylpropionic acid | Generator | alpha,alpha-Dimethylpropionate | Generator | Α,α-dimethylpropionate | Generator | Α,α-dimethylpropionic acid | Generator | Dimethylpropionate | Generator | Neopentanoate | Generator | Tert-pentanoate | Generator | Trimethylacetate | Generator | Pivalate | Generator | 2,2-Dimethyl-propanoic acid | HMDB | 2,2-Dimethyl-propionic acid | HMDB | 2,2-Dimethylpropanoic acid | HMDB | Kyselina 2,2-dimethylpropionova | HMDB | Kyselina pivalova | HMDB | Neovaleric acid | HMDB | Pivalic acid (acd/name 4.0) | HMDB | Pivalinsaure | HMDB | Tert-C4H9COOH | HMDB | Trimethyl-acetic acid | HMDB | Versatic 5 | HMDB | Pivalic acid, sodium salt | HMDB |
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Chemical Formula | C5H10O2 |
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Average Molecular Weight | 102.1317 |
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Monoisotopic Molecular Weight | 102.068079564 |
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IUPAC Name | 2,2-dimethylpropanoic acid |
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Traditional Name | pivalic acid |
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CAS Registry Number | 75-98-9 |
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SMILES | CC(C)(C)C(O)=O |
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InChI Identifier | InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7) |
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InChI Key | IUGYQRQAERSCNH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. |
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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 | Carboxylic acids |
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Direct Parent | Carboxylic acids |
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Alternative Parents | |
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Substituents | - Monocarboxylic 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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Pivalic acid EI-B (Non-derivatized) | splash10-0a4i-9000000000-e957b65f703c5d0a437e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Pivalic acid CI-B (Non-derivatized) | splash10-0udi-4900000000-230e0140d18957e6c133 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Pivalic acid EI-B (Non-derivatized) | splash10-0a4i-9000000000-e957b65f703c5d0a437e | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Pivalic acid CI-B (Non-derivatized) | splash10-0udi-4900000000-230e0140d18957e6c133 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pivalic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9100000000-9c9424249e591db177fb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pivalic acid GC-MS (1 TMS) - 70eV, Positive | splash10-0abl-9100000000-d0ef6bd0ff990f0e982a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pivalic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 10V, Positive-QTOF | splash10-0udi-3900000000-2fa44ebd114efa84c1eb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 20V, Positive-QTOF | splash10-0a4i-9200000000-50d93d8a6c80fafb7314 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 40V, Positive-QTOF | splash10-0a4l-9000000000-f9cb2c03b6c1d9852f83 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 10V, Negative-QTOF | splash10-0udi-0900000000-22a1ac6f3a1952ac0e52 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 20V, Negative-QTOF | splash10-0udi-0900000000-6c14e98fce7c91ecf298 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 40V, Negative-QTOF | splash10-0udr-9500000000-17d0ccd01dbbf5d59427 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 10V, Negative-QTOF | splash10-0udi-0900000000-4c159e60dacc58e6ba98 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 20V, Negative-QTOF | splash10-0udi-0900000000-4c159e60dacc58e6ba98 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 40V, Negative-QTOF | splash10-0k9l-9200000000-6005f4b54f4cd522cb5d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 10V, Positive-QTOF | splash10-0a4i-9000000000-87a9e3b6de2688f21ca9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 20V, Positive-QTOF | splash10-0a4i-9000000000-9290e064976d791d3ebf | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pivalic acid 40V, Positive-QTOF | splash10-0a4i-9000000000-1398b3c94c7e4a370a6b | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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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 | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB111687 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 6177 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Pivalic_acid |
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METLIN ID | Not Available |
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PubChem Compound | 6417 |
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PDB ID | Not Available |
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ChEBI ID | 45133 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1293561 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Basso B, Ullrich-Eberius CI: Membrane Potential and Proton Cotransport of Alanine and Phosphate as Affected by Permeant Weak Acids in Lemna gibba. Plant Physiol. 1987 Nov;85(3):674-8. [PubMed:16665758 ]
- Deutsch CJ, Holian A, Holian SK, Daniele RP, Wilson DF: Transmembrane electrical and pH gradients across human erythrocytes and human peripheral lymphocytes. J Cell Physiol. 1979 Apr;99(1):79-93. [PubMed:37251 ]
- Ovcharenko V, Fursova E, Romanenko G, Eremenko I, Tretyakov E, Ikorskii V: Synthesis, structure, and magnetic properties of (6-9)-nuclear Ni(II) trimethylacetates and their heterospin complexes with nitroxides. Inorg Chem. 2006 Jul 10;45(14):5338-50. [PubMed:16813397 ]
- Brass EP: Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev. 2002 Dec;54(4):589-98. [PubMed:12429869 ]
- Li C, Benet LZ, Grillo MP: Enantioselective covalent binding of 2-phenylpropionic Acid to protein in vitro in rat hepatocytes. Chem Res Toxicol. 2002 Nov;15(11):1480-7. [PubMed:12437340 ]
- Deutsch C, Drown C, Rafalowska U, Silver IA: Synaptosomes from rat brain: morphology, compartmentation, and transmembrane pH and electrical gradients. J Neurochem. 1981 Jun;36(6):2063-72. [PubMed:7241148 ]
- Xiang TX, Anderson BD: Influence of chain ordering on the selectivity of dipalmitoylphosphatidylcholine bilayer membranes for permeant size and shape. Biophys J. 1998 Dec;75(6):2658-71. [PubMed:9826590 ]
- Kaljuste K, Unden A: New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase. Int J Pept Protein Res. 1993 Aug;42(2):118-24. [PubMed:8407105 ]
- Li C, Grillo MP, Benet LZ: In vitro studies on the chemical reactivity of 2,4-dichlorophenoxyacetyl-S-acyl-CoA thioester. Toxicol Appl Pharmacol. 2003 Mar 1;187(2):101-9. [PubMed:12649042 ]
- Yamada H, Kato C: Solvent and steric effects on the extraction of copper(II) with pivalic acid. Talanta. 1993 Jul;40(7):1049-57. [PubMed:18965747 ]
- Choi KY, Kim DW, Kim CS, Hong CP, Ryu H, Lee YI: Formation and dissociation kinetics of triaza-crown-alkanoic acid complexes of transition metal(II) and lanthanide (III). Talanta. 1997 Apr;44(4):527-34. [PubMed:18966771 ]
- Lyubinetsky I, Deskins NA, Du Y, Vestergaard EK, Kim DJ, Dupuis M: Adsorption states and mobility of trimethylacetic acid molecules on reduced TiO(2)(110) surface. Phys Chem Chem Phys. 2010 Jun 21;12(23):5986-92. doi: 10.1039/b921921h. Epub 2010 May 21. [PubMed:20490397 ]
- Burov SV, Iablokova TV, Dorosh MIu, Shkarubskaia ZP, Blank M, Epshtein N, Fridkin M: [Luliberin analogues exhibiting a cytotoxic effect on tumor cells in vitro]. Bioorg Khim. 2006 Sep-Oct;32(5):459-66. [PubMed:17042263 ]
- Deutsch C, Erecinska M, Werrlein R, Silver IA: Cellular energy metabolism, trans-plasma and trans-mitochondrial membrane potentials, and pH gradients in mouse neuroblastoma. Proc Natl Acad Sci U S A. 1979 May;76(5):2175-9. [PubMed:36613 ]
- Ruff LJ, Brass EP: Metabolic effects of pivalate in isolated rat hepatocytes. Toxicol Appl Pharmacol. 1991 Sep 1;110(2):295-302. [PubMed:1891775 ]
- Li C, Grillo MP, Benet LZ: In vivo mechanistic studies on the metabolic activation of 2-phenylpropionic acid in rat. J Pharmacol Exp Ther. 2003 Apr;305(1):250-6. [PubMed:12649376 ]
- Xiang TX, Anderson BD: Phase structures of binary lipid bilayers as revealed by permeability of small molecules. Biochim Biophys Acta. 1998 Mar 6;1370(1):64-76. [PubMed:9518554 ]
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