Butylmalonic Acid Research Articles

Dipodal Tetraamide Derivatives of 1,10-Diaza-18-Crown-6 and Alkylmalonic Acids-Synthesis and Use as Ionophores in Ion Selective Membrane Electrodes.

Novel dipodal derivatives of an 18-membered diaza-crown ether with two diamide chains featuring methylmalonic or butylmalonic acid residues were obtained and tested as ionophores in ion-selective plasticized membrane electrodes. The objective of the study was to identify measurement conditions which ensure the most favorable performance for magnesium ion-selective electrodes. The relationship between the molar lipophilic anion salt-to-ionophore ratio and selectivity of electrodes was examined. The best result was obtained for the conventional electrode containing Mg2 ionophore. Calculated selectivity coefficients were as follows: logKMg/Ca = −2.77, logKMg/Na = −3.46 and logKMg.K = −2.24 (SSM, 1M).

Transporter-Mediated Mitochondrial GSH Depletion Leading to Mitochondrial Dysfunction and Rescue with αB Crystallin Peptide in RPE Cells.

Mitochondrial glutathione (mGSH) is critical for cell survival. We recently reported the localization of OGC (SLC25A11) and DIC (SLC25A10) in hRPE. Herein, we investigated the suppression of OGC and DIC and the effect of αB crystallin chaperone peptide co-treatment on RPE cell death and mitochondrial function. Non-polarized and polarized human RPE were co-treated for 24 h with phenyl succinic acid (PS, 5 mM) or butyl malonic acid (BM, 5 mM) with or without αB cry peptide (75 µg/mL). mGSH levels, mitochondrial bioenergetics, and ETC proteins were analyzed. The effect of mGSH depletion on cell death and barrier function was determined in polarized RPE co-treated with PS, OGC siRNA or BM and αB cry peptide. Inhibition of OGC and DIC resulted in a significant decrease in mGSH and increased apoptosis. mGSH depletion significantly decreased mitochondrial respiration, ATP production, and altered ETC protein expression. αB cry peptide restored mGSH, attenuated apoptosis, upregulated ETC proteins, and improved mitochondrial bioenergetics and biogenesis. mGSH transporters exhibited differential polarized localization: DIC (apical) and OGC (apical and basal). Inhibition of mGSH transport compromised barrier function which was partially restored by αB cry peptide. Our findings suggest mGSH augmentation by its transporters may be a valuable approach in AMD therapy.

Synthesis, structure, and ESR spectra of the new heteronuclear complex {Li4(VO)2[(OOC)2C(H)Bu]4(H2O)8}·H2O

The reaction of an aqueous solution of vanadyl sulfate VOSO4·3H2O, butylmalonic acid (H2Bumal = C4H10(COOH)2), and lithium carbonate at pH ∼4–5 gave crystals of the complex Li4(VO)2(Bumal)4(H2O)8]·H2O (1). The structure of complex 1 was established by X-ray diffraction analysis. The molecule of complex 1 consists of two mononuclear bischelate dianionic units {VO(Bumal)2(H2O)} linked by four lithium ions to form the hexanuclear heterometallic {V2Li4} structure. The crystals and an ethanolic solution of compound 1 were studied by ESR spectroscopy.

Ethylmalonic acid impairs brain mitochondrial succinate and malate transport

Tissue accumulation and high urinary excretion of ethylmalonic acid (EMA) occur in ethylmalonic encephalopathy (EE) and short chain acyl-CoA dehydrogenase deficiency (SCADD). Although these autosomal recessive disorders are clinically characterized by neurological abnormalities, the mechanisms underlying the brain damage are poorly known. Considering that little is known about the neurotoxicity of EMA and that hyperlacticacidemia occurs in EE and SCADD, we evaluated the effects of this metabolite on important parameters of oxidative metabolism in isolated rat brain mitochondria. EMA inhibited either ADP-stimulated or uncoupled mitochondrial respiration supported by succinate and malate, but not by glutamate plus malate. In addition, EMA mildly stimulated oxygen consumption by succinate-respiring mitochondria in resting state. Methylmalonic acid (MMA), malonic acid (MA) and butylmalonic acid (BtMA) had a similar effect on ADP-stimulated or uncoupled respiration. Furthermore, EMA-, MMA- and BtMA-induced inhibitory effects on succinate oxidation were significantly minimized by nonselective permeabilization of the mitochondrial membranes by alamethicin, whereas MA inhibitory effect was not altered. In addition, MA was the only tested compound that reduced succinate dehydrogenase activity. We also observed that EMA markedly inhibited succinate and malate transport through the mitochondrial dicarboxylate carrier. Mitochondrial membrane potential was also reduced by EMA and MA, but not by MMA, using succinate as electron donor, whereas none of these compounds was able to alter the membrane potential using glutamate plus malate as electron donors. Taken together, our results strongly indicate that EMA impairs succinate and malate uptake through the mitochondrial dicarboxylate carrier.

Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) butylmalonate

The title compound, C27H50N2O4, was prepared from butylmalonic acid and 1,2,2,6,6-pentamethyl-4-hydroxypiperidine by transesterification. In the molecule, both piperidine rings adopt chair conformations.

Standard Enthalpies, Entropies, and Gibbs Functions of Sublimation of Four Alkyl-Substituted Malonic Acids

The Knudsen mass-loss effusion technique was used to measure the vapor pressures at different temperatures of the following crystalline dicarboxylic acids: methylmalonic acid, between 341.13 K and 354.74 K, dimethylmalonic acid, between 347.18 K and 363.26 K, ethylmalonic acid, between 347.52 K and 362.34 K and butylmalonic acid, between 348.20 K and 362.18 K. From the temperature dependence of the vapor pressure, the standard molar enthalpies of sublimation were derived by the Clausius−Clapeyron equation and the molar entropies of sublimation at equilibrium pressures were calculated. Using estimated values for the heat capacity differences between the gas and the crystal phases of the studied compounds the standard (pressure p0 = 105 Pa) molar enthalpies, entropies and Gibbs functions of sublimation at T = 298.15 K, were derived.

Chemical and Electrochemical Synthesis of Transition Metal Complexes of Butylmalonic Acid Dihydrazide and its Salicyloyl Hydrazone

Iron, cobalt, nickel and copper complexes of butylmalonic acid dihydrazide (H2BMD) and its salicyloylhydrazone (H4BMS) have been prepared by interaction of the ligands with the metal salt solutions or by direct electrochemical oxidation of the metal in acetone solution of the ligand. Higher yields (85-90%) were obtained by the electrochemical method. IR spectra show that H2BMD and H4BMS behave as neutral or binegative ligands binding in a bidentate, tridentate and/or tetradentate manner, depending on the preparative conditions. Different (octahedral, tetrahedral and square-planar) geometries are suggested for the isolated complexes based on magnetic and electronic spectral studies. The ligand field parameters of the Co(II) and Ni(II) complexes were calculated and the variation of their values with the change of coordination sites is discussed.

Kinetic study of the Ce(III)- or ferroin-catalyzed Belousov-Zhabotinsky reaction with ethyl- or butyl-malonic acid

In a stirred batch experiment, ferroin (Fe(phen)32+) behaves differently from Ce(III) as a catalyst for the Belousov-Zhabotinsky reaction with ethyl- or n-butyl-malonic acid (EtMA or BuMA) The effects of bromate ion, organic substrate, metal-ion catalyst, and sulfuric acid on the oscillating pattern were investigated. The kinetics of the reactions of methylmalonic acid (MeMA), bromomethyl-malonic acid (BrMeMA), EtMA, bromoethylmalonic acid (BrEtMA), BuMA, bromo(n-butyl)malonic acid (BrBuMA) with Ce(IV) or Fe(phen)33+ ion were studied. Under aerobic or anaerobic conditions, the order of reactivity toward Ce(IV) oxidation is MeMA > EtMA > BuMA > BrMeMA >> (BrEtMA, BrBuMA). Under aerobic conditions, the order of reactivity toward reacting with Fe(phen)33+ ion is MeMA > (BuMA, EtMA) >> (BrMeMA, BrEtMA, BrBuMA). The experimental results are rationalized. © 1996 John Wiley & Sons, Inc.

The kinetics of the decarboxylation of n‐butylmalonic acid in alkanols and amines

AbstractRate constants and activation parameters are reported for the decarboxylation of n‐butylmalonic acid in four normal alkanols (hexanol1, octanol1, decanol1, and dodecanol1) and in five amines (aniline, N‐methylaniline, N‐ethylaniline, N‐n‐propylaniline, and N‐n‐butylaniline). Both ΔH‡ and ΔS‡ of the reaction in both homologous series decrease regularly with increasing length of the hydrocarbon chain of solvent. If we compare data for the reaction in alkanol–amine pairs containing the same total number of carbon atoms in the molecule, we find that the ΔH‡ values are identical, but that the value of ΔS‡ is 0.8 eu/mole higher for the reaction in the amines as compared with the alcohol. The rate constant, at all temperatures, is 1.5 times as large in the amine as it is in the corresponding alcohol. Empirical equations are deduced relating the parameters ΔH‡ ΔS‡ ΔG‡ and k of the reaction to the parameters n and T, where n is the total number of carbon atoms in the solvent molecule and T is the absolute temperature. The results reported herein are compared with previously reported data for malonic acid.

Hydrolysis equilibrium of phenylbutazone (Butazolidin)

AbstractPhenylbutazone (I) forms in aqueous and partially aqueous solution butylmalonic acid mono (N, N′‐diphenylhydrazide) (II) by a reversible reaction. The reaction rate and the position of equilibrium depend on the solvent but practically not on the pH. The temperature dependence is given for several media. Substituents affect the reaction rate when they are in 4‐position but not in 4′‐ or 4″‐position. Based on the kinetic data, a reaction mechanism is proposed. Methods for the analysis of I in mixtures with II are presented. The preparation of II is described.

The Effects of Certain Psychopharmacologic Drugs on Conditioning in the Rat I : Avoidance-Escape Conditioning

This study compares the effects on conditioning of well-known classes of tranquilizers both with themselves and with other centrally active drugs. On the basis of certain chemical structure relationships, 2-ethyl-2-(3-methyl)-butylmalondiamide, 2-ethyl-2-(3-methyl)-butylmalonic acid diethylester, and ethyl-2,4-toluene dicarbamate were included for study. The results which were analyzed statistically by means of an analysis of variance technique and t tests demonstrated significant differences between drugs and between drugs and controls from both dosage and trial aspects. Because of the nature of the test, these differences cannot be ascribed only to an interference with normal motor activity.

The Preparation of t-Butylmalonic Acid from Neopentyl Chloride

The Preparation of <i>t</i>-Butylmalonic Acid from Neopentyl Chloride

The Preparation of t-Butylmalonic Acid and Some of its Derivatives

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Preparation of t-Butylmalonic Acid and Some of its DerivativesMilton T. BushCite this: J. Am. Chem. Soc. 1939, 61, 3, 637–638Publication Date (Print):March 1, 1939Publication History Published online1 May 2002Published inissue 1 March 1939https://doi.org/10.1021/ja01872a027RIGHTS & PERMISSIONSArticle Views70Altmetric-Citations2LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (231 KB) Get e-Alerts Get e-Alerts