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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:52:01 UTC
Update Date2017-12-07 04:30:05 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
Thumb
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
PivalateGenerator
a,a-DimethylpropionateGenerator
a,a-Dimethylpropionic acidGenerator
alpha,alpha-DimethylpropionateGenerator
α,α-dimethylpropionateGenerator
α,α-dimethylpropionic acidGenerator
DimethylpropionateGenerator
NeopentanoateGenerator
Tert-pentanoateGenerator
TrimethylacetateGenerator
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 saltMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These 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
Disposition

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.7 mg/mL at 20 °CNot Available
LogP1.48Not Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-e957b65f703c5d0a437eView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-4900000000-230e0140d18957e6c133View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-e957b65f703c5d0a437eView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-4900000000-230e0140d18957e6c133View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-9c9424249e591db177fbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0abl-9100000000-d0ef6bd0ff990f0e982aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-2fa44ebd114efa84c1ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-50d93d8a6c80fafb7314View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-f9cb2c03b6c1d9852f83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-22a1ac6f3a1952ac0e52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-6c14e98fce7c91ecf298View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-9500000000-17d0ccd01dbbf5d59427View in MoNA
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6177
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPivalic_acid
METLIN IDNot Available
PubChem Compound6417
PDB IDPIV
ChEBI ID45133
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 ]