Pivalic acid

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H10O2
Molecular Weight	102.1317
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C(O)=O

InChI

InChIKey=IUGYQRQAERSCNH-UHFFFAOYSA-N

InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)

HIDE SMILES / InChI

Molecular Formula	C5H10O2
Molecular Weight	102.1317
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
The P2Y(1) and P2Y(12) receptors mediate autoinhibition of transmitter release in sympathetic innervated tissues.	2009-12	19447154
Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2.	2009-08-14	19539806
Tridecanuclear [Mn(III)5Ln(III)8] complexes derived from N-(t)butyl-diethanolamine: synthesis, structures, and magnetic properties.	2009-07-20	19530694
Effect of MK-886 on Ca2+ level and viability in PC3 human prostate cancer cells.	2009-06	19371256
Family of heterometallic semicircular Mn(III)2Ln(III)3 strands.	2009-04-20	19317423
Establishment of broadly applicable reaction conditions for the palladium-catalyzed direct arylation of heteroatom-containing aromatic compounds.	2009-03-06	19206211
C-H bonds as ubiquitous functionality: a general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition.	2009-03-04	19206533
Tetra-, tri-, and mononuclear manganese(II/III) complexes of a phenol-based N2O2 capping ligand: use of carboxylates as ancillary ligands in tuning the nuclearity of the complexes.	2009-03-02	19235946
Development of selective agonists and antagonists of P2Y receptors.	2009-03	18600475
Children's toxicology from bench to bed--Liver injury (1): Drug-induced metabolic disturbance--toxicity of 5-FU for pyrimidine metabolic disorders and pivalic acid for carnitine metabolism.	2009	19571472
C(aryl)-O activation of aryl carboxylates in nickel-catalyzed biaryl syntheses.	2009	19280618
Phosphine-free, palladium-catalyzed arylation of heterocycles through C-H bond activation with pivalic acid as a cocatalyst.	2009	19115287
Novel multifunctional acyloxyalkyl ester prodrugs of 5-aminolevulinic acid display improved anticancer activity independent and dependent on photoactivation.	2008-12-11	19007111
Cross-coupling reactions of aryl pivalates with boronic acids.	2008-11-05	18839946
An expedient route to Montanine-type Amaryllidaceae alkaloids: total syntheses of (-)-brunsvigine and (-)-manthine.	2008-10-03	18781802
Enantioselective formation of ibuprofen-S-acyl-glutathione in vitro in incubations of ibuprofen with rat hepatocytes.	2008-09	18680316
Scanning tunneling microscopy study of black dye and deoxycholic acid adsorbed on a rutile TiO2(110).	2008-08-05	18590297
Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: reaction development and scope.	2008-07-04	18543991
Effectiveness of UV-based advanced oxidation processes for the remediation of hydrocarbon pollution in the groundwater: a laboratory investigation.	2008-04-15	17890002
Pivaloyloxymethyl-modified isoprenoid bisphosphonates display enhanced inhibition of cellular geranylgeranylation.	2008-04-01	18308574
Fluoxetine (Prozac) augments platelet activation mediated through protease-activated receptors.	2008-04	18194419
Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates.	2008-03-26	18311985
Ion-pair interaction in pyridinium carboxylate solutions.	2008-02-07	18189374
Protic ionic liquids: physicochemical properties and behavior as amphiphile self-assembly solvents.	2008-01-24	18166036
Mixed valence complexes involving MM quadruple bonds (M=Mo or W).	2008-01-13	17846014
Cross-coupling of aryl/alkenyl pivalates with organozinc reagents through nickel-catalyzed C-O bond activation under mild reaction conditions.	2008	19016280
Role of Na+/L-carnitine transporter (OCTN2) in renal handling of pivaloylcarnitine and valproylcarnitine formed during pivalic acid-containing prodrugs and valproic acid treatment.	2008	18762717
Epigenetic treatment of myelodysplastic syndromes and acute myeloid leukemias.	2008	18537607
Inhibitory purinergic transmission in mouse caecum: role for P2Y1 receptors as prejunctional modulators of ATP release.	2007-12-12	17997228
Toward a magnetostructural correlation for a family of Mn6 SMMs.	2007-10-17	17887755
Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid.	2007-09	17724113
5(6)-carboxyfluorescein revisited: new protecting group, separation of isomers, and their spectral properties on oligonucleotides.	2007-08-19	17696491
Tixocortol pivalate: what is the right concentration?	2007-07	17577357
Pivalate lowers litter sizes and weights in female rats independent of its effect on carnitine status.	2007-07	17482425
Investigating the mechanistic basis for hepatic toxicity induced by an experimental chemokine receptor 5 (CCR5) antagonist using a compendium of gene expression profiles.	2007-06	17654398
Conformational enantiomeric disorder in tripivaloylmethane.	2007-06	17551202
Evidence that ATP or a related purine is an excitatory neurotransmitter in the longitudinal muscle of mouse distal colon.	2007-05	17351663
Chromium-catalyzed arylmagnesiation of alkynes.	2007-04-12	17352489
Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.	2006-12-27	17177387
Studies of a molecular hourglass: synthesis and magnetic characterisation of a cyclic dodecanuclear {Cr10Cu2} complex.	2006-11-06	17009364
[Luliberin analogues exhibiting a cytotoxic effect on tumor cells in vitro].	2006-10-18	17042263
Pyrones to pyrans: enantioselective radical additions to acyloxy pyrones.	2006-10-18	17031933
1D helical polymeric chain with a pseudo-5(3) screw axis formed by cuprophilicity. synthesis and crystal structure of copper(I) pivalate.	2006-09-18	16961347
Induction of parturition in dairy cattle and its effects on health and subsequent lactation and reproductive performance.	2006-09	16958626
Involvement of recognition and interaction of carnitine transporter in the decrease of L-carnitine concentration induced by pivalic acid and valproic acid.	2006-08	16826461
Antiplasmodial and antitrypanosomal activity of new esters and ethers of 4-dialkylaminobicyclo[2.2.2]octan-2-ols.	2006-08	16713699
Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst.	2006-07-21	16839166
Synthesis, structure, and magnetic properties of (6-9)-nuclear Ni(II) trimethylacetates and their heterospin complexes with nitroxides.	2006-07-10	16813397
Synthesis, reactivities, and magnetostructural properties of FeIII, FeIII-O-FeIII, and ZnIIFeIII-O-FeIIIZnII complexes of a tetraiminodiphenolate macrocycle.	2006-06-12	16749848
Hypocarnitinaemia induced by sodium pivalate in the rat is associated with left ventricular dysfunction and impaired energy metabolism.	2006	16752941

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:24:39 GMT 2025` Edited by `admin` on `Mon Mar 31 21:24:39 GMT 2025`
Record UNII	813RE8BX41
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2,2-DIMETHYLPROPANOIC ACID

Preferred Name

English

Pivalic acid

Systematic Name

English

2,2-DIMETHYLPROPANOIC ACID [HSDB]

Common Name

English

NEOPENTANOIC ACID

Systematic Name

English

NSC-65449

Code

English

PIVALIC ACID [MI]

Common Name

English

TRIMETHYLACETIC ACID

Systematic Name

English

Code System Code Type Description

FDA UNII

813RE8BX41