Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:01 UTC

Update Date

2023-02-21 17:29:05 UTC

HMDB ID

HMDB0041992

Secondary Accession Numbers

HMDB41992

Metabolite Identification

Common Name

Pivalic acid

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
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

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

2,2-dimethylpropanoic acid

Traditional Name

pivalic acid

CAS Registry Number

75-98-9

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 Key

IUGYQRQAERSCNH-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain saturated fatty acid (CHEBI:45133 )
methyl-branched fatty acid (CHEBI:45133 )
short-chain fatty acid (CHEBI:45133 )
Branched fatty acids (LMFA01020073 )

Ontology

Not Available

Endogenous (HMDB: HMDB0041992)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	35 °C	Not Available
Boiling Point	164.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	21.7 mg/mL at 20 °C	Not Available
LogP	1.48	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	56.9 g/L	ALOGPS
logP	1.37	ALOGPS
logP	1.58	ChemAxon
logS	-0.25	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.35 m³·mol⁻¹	ChemAxon
Polarizability	10.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	121.05	31661259
DarkChem	[M-H]-	114.275	31661259
DeepCCS	[M+H]+	125.579	30932474
DeepCCS	[M-H]-	122.78	30932474
DeepCCS	[M-2H]-	159.214	30932474
DeepCCS	[M+Na]+	133.939	30932474
AllCCS	[M+H]+	124.2	32859911
AllCCS	[M+H-H2O]+	120.1	32859911
AllCCS	[M+NH4]+	128.2	32859911
AllCCS	[M+Na]+	129.3	32859911
AllCCS	[M-H]-	123.5	32859911
AllCCS	[M+Na-2H]-	127.6	32859911
AllCCS	[M+HCOO]-	132.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pivalic acid	CC(C)(C)C(O)=O	1472.9	Standard polar	33892256
Pivalic acid	CC(C)(C)C(O)=O	758.1	Standard non polar	33892256
Pivalic acid	CC(C)(C)C(O)=O	782.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pivalic acid,1TMS,isomer #1	CC(C)(C)C(=O)O[Si](C)(C)C	851.1	Semi standard non polar	33892256
Pivalic acid,1TBDMS,isomer #1	CC(C)(C)C(=O)O[Si](C)(C)C(C)(C)C	1090.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Deposition Date	Source	View
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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111687

KNApSAcK ID

Not Available

Chemspider ID

6177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pivalic_acid

METLIN ID

Not Available

PubChem Compound

6417

PDB ID

Not Available

ChEBI ID

45133

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1293561

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Showing metabocard for Pivalic acid (HMDB0041992)

MOL for HMDB0041992 (Pivalic acid)

3D MOL for HMDB0041992 (Pivalic acid)

3D SDF for HMDB0041992 (Pivalic acid)

3D-SDF for HMDB0041992 (Pivalic acid)

PDB for HMDB0041992 (Pivalic acid)

3D PDB for HMDB0041992 (Pivalic acid)

SMILES for HMDB0041992 (Pivalic acid)

INCHI for HMDB0041992 (Pivalic acid)

Structure for HMDB0041992 (Pivalic acid)

3D Structure for HMDB0041992 (Pivalic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra