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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:52:01 UTC
Update Date2023-02-21 17:29:05 UTC
HMDB IDHMDB0041992
Secondary Accession Numbers
  • HMDB41992
Metabolite Identification
Common NamePivalic acid
DescriptionPivalic 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.
Structure
Data?1677000545
Synonyms
ValueSource
2,2-Dimethylpropionic acidChEBI
Acide 2,2-dimethylpropanoiqueChEBI
Acide pivaliqueChEBI
Acido pivalicoChEBI
alpha,alpha-Dimethylpropionic acidChEBI
Dimethylpropionic acidChEBI
Neopentanoic acidChEBI
PivalinsaeureChEBI
Tert-pentanoic acidChEBI
Trimethylacetic acidChEBI
2,2-DimethylpropionateGenerator
a,a-DimethylpropionateGenerator
a,a-Dimethylpropionic acidGenerator
alpha,alpha-DimethylpropionateGenerator
Α,α-dimethylpropionateGenerator
Α,α-dimethylpropionic acidGenerator
DimethylpropionateGenerator
NeopentanoateGenerator
Tert-pentanoateGenerator
TrimethylacetateGenerator
PivalateGenerator
2,2-Dimethyl-propanoic acidHMDB
2,2-Dimethyl-propionic acidHMDB
2,2-Dimethylpropanoic acidHMDB
Kyselina 2,2-dimethylpropionovaHMDB
Kyselina pivalovaHMDB
Neovaleric acidHMDB
Pivalic acid (acd/name 4.0)HMDB
PivalinsaureHMDB
Tert-C4H9COOHHMDB
Trimethyl-acetic acidHMDB
Versatic 5HMDB
Pivalic acid, sodium saltHMDB
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name2,2-dimethylpropanoic acid
Traditional Namepivalic acid
CAS Registry Number75-98-9
SMILES
CC(C)(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)
InChI KeyIUGYQRQAERSCNH-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling Point164.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21.7 mg/mL at 20 °CNot Available
LogP1.48Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility56.9 g/LALOGPS
logP1.37ALOGPS
logP1.58ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.35 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.0531661259
DarkChem[M-H]-114.27531661259
DeepCCS[M+H]+125.57930932474
DeepCCS[M-H]-122.7830932474
DeepCCS[M-2H]-159.21430932474
DeepCCS[M+Na]+133.93930932474
AllCCS[M+H]+124.232859911
AllCCS[M+H-H2O]+120.132859911
AllCCS[M+NH4]+128.232859911
AllCCS[M+Na]+129.332859911
AllCCS[M-H]-123.532859911
AllCCS[M+Na-2H]-127.632859911
AllCCS[M+HCOO]-132.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pivalic acidCC(C)(C)C(O)=O1472.9Standard polar33892256
Pivalic acidCC(C)(C)C(O)=O758.1Standard non polar33892256
Pivalic acidCC(C)(C)C(O)=O782.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pivalic acid,1TMS,isomer #1CC(C)(C)C(=O)O[Si](C)(C)C851.1Semi standard non polar33892256
Pivalic acid,1TBDMS,isomer #1CC(C)(C)C(=O)O[Si](C)(C)C(C)(C)C1090.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pivalic acid EI-B (Non-derivatized)splash10-0a4i-9000000000-e957b65f703c5d0a437e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pivalic acid CI-B (Non-derivatized)splash10-0udi-4900000000-230e0140d18957e6c1332017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pivalic acid EI-B (Non-derivatized)splash10-0a4i-9000000000-e957b65f703c5d0a437e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pivalic acid CI-B (Non-derivatized)splash10-0udi-4900000000-230e0140d18957e6c1332018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pivalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-9c9424249e591db177fb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pivalic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0abl-9100000000-d0ef6bd0ff990f0e982a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pivalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 10V, Positive-QTOFsplash10-0udi-3900000000-2fa44ebd114efa84c1eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 20V, Positive-QTOFsplash10-0a4i-9200000000-50d93d8a6c80fafb73142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-f9cb2c03b6c1d9852f832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 10V, Negative-QTOFsplash10-0udi-0900000000-22a1ac6f3a1952ac0e522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 20V, Negative-QTOFsplash10-0udi-0900000000-6c14e98fce7c91ecf2982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 40V, Negative-QTOFsplash10-0udr-9500000000-17d0ccd01dbbf5d594272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 10V, Negative-QTOFsplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 20V, Negative-QTOFsplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 40V, Negative-QTOFsplash10-0k9l-9200000000-6005f4b54f4cd522cb5d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 10V, Positive-QTOFsplash10-0a4i-9000000000-87a9e3b6de2688f21ca92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-9290e064976d791d3ebf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pivalic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-1398b3c94c7e4a370a6b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111687
KNApSAcK IDNot Available
Chemspider ID6177
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPivalic_acid
METLIN IDNot Available
PubChem Compound6417
PDB IDNot Available
ChEBI ID45133
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1293561
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Brass EP: Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev. 2002 Dec;54(4):589-98. [PubMed:12429869 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. Ruff LJ, Brass EP: Metabolic effects of pivalate in isolated rat hepatocytes. Toxicol Appl Pharmacol. 1991 Sep 1;110(2):295-302. [PubMed:1891775 ]
  16. 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 ]
  17. 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 ]