Dimethyl Succinate Research Articles

The study of catalyst effects on the complexation of arenes with Cr(CO) 6. An overview

The results from our thorough investigation of different catalystic effects on the rate and yields of complexation of arenes with Cr(CO) are presented with a short review of the subject. With decalin as solvent the following substances were found to be the best catalysts: butyl acetate, ethyl formate, and dimethyl succinate. Butyl acetate proved to be the catalyst also in-di-n-butyl ether. Special attention was paid to the complexation of naphthalene, and chlorobenzene. Some unsuccessful attempts at asymmetric induction of complexation are also described.

Deposition of dibasic esters in the upper respiratory tract of the male and female Sprague-Dawley rat

Inhalation exposure of the male and female rat to high concentrations of a mixture of the dibasic esters dimethyl succinate (DMS), dimethyl glutarate (DMG), and dimethyl adipate (DMA) results in mild olfactory toxicity. This response is thought to be due to the in situ formation of acidic metabolites via nasal carboxylesterases. The current study was designed to provide inhalation dosimetric information for these vapors. Deposition of DMS, DMG, and DMA was measured in the surgically isolated upper respiratory tracts (URT) of ketamine-xylazine-anesthetized male and female rats under constant velocity flow conditions at a flow rate of 100 ml/min. Deposition of acetone was measured in both genders for comparative purposes. URT deposition efficiencies in excess of 98.3% were observed for DMS, DMG, and DMA in animals exposed to each vapor individually. No gender differences in deposition efficiency were observed for these vapors or for acetone. Deposition of DMS, DMG, and DMA was also measured in animals exposed to all three vapors simultaneously. Deposition efficiency under simultaneous exposure conditions ranged between 97.3 and 98.5%. These values were slightly lower (about 1%) than those obtained under individual exposure conditions ( p < 0.0001). The reduced deposition efficiency may have resulted from competitive inhibition of nasal metabolism due to the simultaneous presence of all three carboxylesterase substrate vapors in nasal tissues. If so, inhalation of dibasic ester vapors would be expected to inhibit the uptake of other carboxylesterase substrate vapors without influencing uptake of vapors which are not substrates for this enzyme. Such was observed in studies using DMS, ethyl acetate (the substrate vapor), and isoamyl alcohol (the nonsubstrate vapor). Specifically, simultaneous exposure to DMS markedly inhibited uptake of ethyl acetate without altering uptake of isoamyl alcohol. Gender differences were not observed in URT deposition of any of the six vapors used in the current study, DMS, DMG, DMA, ethyl acetate, isoamyl alcohol, or acetone, suggesting that gender differences in URT deposition may not be widespread among vapors. The high URT deposition efficiencies of the dibasic esters are consistent with the olfactory toxicity resulting from inhalation exposure to these vapors.

Carboxylesterase-dependent cytotoxicity of dibasic esters (DBE) in rat nasal explants

Dibasic esters (DBE) are a solvent mixture of dimethyl adipate (DMA), dimethyl glutarate (DMG), and dimethyl succinate (DMS) used in the paint and coating industry. Subchronic inhalation toxicity studies have demonstrated that DBE induce a mild degeneration of the olfactory, but not the respiratory, epithelium of the rat nasal cavity. Carboxylesterase-mediated hydrolysis of the individual dibasic esters is more efficient in olfactory than in respiratory mucosal homogenates. In the present study, an in vitro system of cultured rat nasal explants was utilized to determine if DBE toxicity is dependent on a metabolic activation by nonspecific carboxylesterase. Explants from both the olfactory and the respiratory regions of the female rat nasal cavity were incubated for 2 hr in Williams' medium E containing 10–100 m m DMA, DMG, or DMS. DBE caused a dose-related increase in nasal explant acid phosphatase release, a biochemical index of cytotoxicity. HPLC analysis demonstrated parallel increases in the carboxylesterase-mediated formation of monomethyl ester metabolites. Diacid metabolite production in the nasal explant system was not entirely concentration-dependent. Metabolite concentrations and acid phosphatase release were generally greater in olfactory than respiratory tissues. DBE-induced cytotoxicity and acid metabolite production were markedly attenuated in nasal tissue excised from rats which were pretreated with bis ( p-nitrophenyl)phosphate, a carboxylesterase inhibitor. This study presents a viable in vitro method for assessing organic ester cytotoxicity in the rat nasal cavity. It was shown that DBE are weak nasal toxicants under the conditions of this system. It was further demonstrated that DBE toxicity is dependent on a carboxylesterase-mediated activation. A similar mechanism was proposed for the nasal toxicity induced by other organic esters following inhalation exposure.

Lignanes, 11. Preparation de la (R)-(+)-β-Vanillyl γ-butyrolactone et Son Utilisation dans la Synthese Totale de Lignanes Naturels

Condensation of vanillin with dimethyl succinate (using LiOMe) gave the ethylenic hemiester 3. Hydrogenation of 3 gave (R,S)-4. The latter was resolved into both its enantiomers by means of (+)-α-methylbenzylamine. Ca(BH 4 ) 2 reduction of (R)-(+)-4 and (S)-(−)-4 gave the corresponding β-vanillyl-γ-butyrolactones (R)-(+)-1 and (S)-(−)-1, respectively. The lactone (R)-(+)-1 was used for the total syntheses of five naturally occurring and optically active lignans such as (−)-anhydrosecoisolariciresinol and (+)-isolariciresinol

Participation of Glucokinase Inactivation in Inhibition of Glucose-Induced Insulin Secretion by 2-Cyclohexen-1-One

We assessed our speculation that 2-cyclohexen-1-one (CHX) impairs glucose-induced insulin secretion through inactivation of glucokinase. Treatment of pancreatic islets with CHX at concentrations (0-5 mM) that caused a dose-dependent inactivation of glucokinase activity similarly inhibited glucose-induced insulin secretion. Another glucose-phosphorylating enzyme (hexokinase) in pancreatic islets was little affected by CHX. CHX-induced inactivation of glucokinase was blocked by the presence of its substrates (glucose and mannose) and an inhibitor (N-acetylglucosamine), all of which also protected against the inhibitory effect of the drug on glucose-induced insulin secretion. CHX also impaired insulin secretion induced by D-glyceraldehyde and dimethyl succinate, which are believed to stimulate the release of the hormone by being directly oxidized by glyceraldehyde-3-phosphate dehydrogenase, by entering the midstream of the glycolytic pathway as glyceraldehyde 3-phosphate, or by entering the tricarboxylic acid cycle in mitochondria after intracellular hydrolysis. The inhibitory effect of CHX on glucose-induced insulin secretion, however, was far more marked than that on insulin secretion evoked by D-glyceraldehyde and dimethyl succinate at any CHX concentrations used. Our study revealed that the inhibitory action of CHX on glucose-induced insulin secretion is exerted mainly, but not solely, through inactivation of glucokinase. This conclusion supports the view that glucokinase is a key enzyme in the recognition of glucose as an insulin secretagogue in pancreatic islets.

ChemInform Abstract: Transformation of Diethyl Phosphite in the Presence of Mn2(CO)10.

AbstractHeating of diethyl phosphite (I) with methyl bromoacetate (II) in the presence of dimanganese decacarbonyl gives triethyl phosphate (III), diethyl ethylphosphonate (IV), methyl acetate (V), and dimethyl succinate (VI).

Hydrogenolysis of dimethyl succinate over Raney copper catalyst: a correction

Presentation de nouvelles donnees experimentales pour l'energie libre et l'enthalpie de formation de tous les reactifs et produits et etude de la cinetique de la reaction

Studies on ruthenium-tin boride catalysts II. Hydrogenation of fatty acid esters to fatty alcohols

Hydrogenation of methyl hexadecanoate, methyl-9-octadecenoate, and dimethyl succinate was studied as a function of catalyst composition as well as various reaction parameters. It was found that an atomic ratio of Ru to Sn of 1 : 1 gave maximum activity and selectivity for alcohol formation from methyl hexadecanoate and dimethyl succinate. Methyl-9-octadecenoate gave the best yield of 9-octadecen-1-ol (the unsaturated alcohol) at an atomic ratio of Ru to Sn of 1 : 2. The hydrogenation of dimethyl succinate was found to depend delicately on the temperature of the reaction, with the diol yields reaching a maximum at 200°C. Based on the characterization of the catalysts and the catalytic activity data, the nature of the active species responsible for the selective hydrogenation and the mode of activation of the ester are discussed.

Crystal structures of dimethylsuccinate and dimethyloxalate: Carbonyl group orientation for C13 chemical shielding tensor studies

The crystal structures of dimethylsuccinate (DMS) and dimethyloxalate (DMO) have been determined to facilitate the determination of the C-13 chemical shielding tensors of the carbonyl carbon in esters. Crystals of DMS are monoclinic, space groupC2/c,Z=4,a=13.154(4),b=6.156(1),c=9.363(4)A,β=98.53(3)°. The structure was solved by direct methods and refined by leastsquares procedures to giveR=0.071 for 932 observed data. Crystals of DMO are monoclinic space group,P21/n,Z=2, witha=3.891(1),b=11.879(2),c=6.213(2) A,β=103.32(2)°. The structure is the same (within experimental error) as that reported by Dougill and Jeffrey (1953) and refined to giveR=0.074 for 395 observed data.

Effect of esters of succinic acid and other citric acid cycle intermediates on insulin release and inositol phosphate formation by pancreatic islets

Esters of carboxylic acids are permeable to cells and once inside the cell are hydrolyzed to carboxylic acids. Methyl and ethyl esters of succinate and other citric acid cycle intermediates were tested to find out whether they are insulin secretagogues. Monomethyl succinate stimulated insulin release from pancreatic islets in a concentration-dependent manner with maximal release attained at a concentration of 10 m m. Dimethyl succinate (10 m m) was as effective as monomethyl succinate, but pyruvate methyl ester, monoethyl succinate, and dimethyl fumarate were ineffective as primary secretagogues. However, dimethyl fumarate potentiated both leucine- and leucine-plus-glutamine-induced insulin release. Glucose, leucine, leucine plus glutamine, and monomethyl succinate increased inositol tris-, bis- and monophosphate formation in pancreatic islets and antimycin A inhibited this formation. Since mitochondrial metabolism is probably essential for glucose-induced insulin release and the metabolism of succinate and leucine (without or with glutamine) involves mitochondrial respiration exclusively, these results might indicate that mitochondrial metabolism generates conditions or factors that are transmitted to the cytosol to increase inositol trisphosphate formation and thus calcium mobilization and insulin release. Since succinate is believed to enter metabolism at site II of the mitochondrial respiratory chain, it is interesting that rotenone, an inhibitor of NADH dehydrogenase and site I of the respiratory chain, was a potent inhibitor of monomethyl succinate-induced insulin released. Rotenone also inhibited leucine (plus or minus glutamine)-induced insulin release. These results indicate that β cell metabolism of monomethyl succinate and leucine, like glucose, influences dehydrogenases that produce NADH.

ChemInform Abstract: Formation of Imidazoline Derivatives from Dimethyl (2,2‐Dimethylhydrazino)succinate and Allyl or Phenyl Isothiocyanate.

AbstractInstead of the expected thiosemicarbazides, the imidazoline derivatives (III) and (IV) are formed during the reaction of the hydrazinosuccinate (I) with the isothiocyanates (II).

Formation of imidazolidine derivatives from dimethyl (2,2-dimethylhydrazino)succinate in reactions with allyl and phenyl isothiocyanates

The reaction of (2,2-dimethylhydrazino)succinic acid ester with allyl and phenyl isothiocyanates leads to esters of 1-substituted (3-dimethylamino-5-oxo-2-thioxo-4-imidazolidinyl)acetic acids, which in protic solvents undergo a slight degree of elimination of dimethylamine to give esters of 1-substituted (5-oxo-2-thioxoimidazolidin-4-ylidene)acetic acids. The structure of methyl (1-allyl-5-oxo-2-thioxoimidazolidin-4-ylidene)acetate was proved by x-ray diffraction analysis.

Reaction kinetics and selectivity of dimethyl succinate hydrogenolysis over copper-based catalysts

Reaction kinetics and selectivity of dimethyl succinate hydrogenolysis over copper-based catalysts

Carbanion Rearrangements. Collision-Induced Reactions of Enolate Negative Ions Derived From Dimethyl Succinates and Hexane-2,5-Dione

Enolate ion MeOCOCHCH2CO2Me fragments through the intermediacy of two ion complexes [ MeOCO (CH2=CHCO2Me)] and [ MeO-(O=C=CHCH2CO2Me)]. The major fragmentations produce CH2=C=C( OMe )O-+HCO2Me and O=C=CH- CH=C( OMe ). Similar ion complexes are formed from methyl-substituted succinates , but their fragmentations are often different from those outlined above: e.g. MeOCOC (Me)C(Me)2CO2Me - [ MeOCO (M2C=CmeCO2Me)] → CH2(Me)C=C(Me)CO2- Me+HCO2Me. The corresponding enolate from hexane-2,s-dione (MeCOCHCH2COMe) fragments through the acetyl anion complex [ MeCO (CH2=CHCO2Me)].

Enantioselective hydrolysis of racemic diesters by porcine pancreatic lipase

Porcine pancreatic lipase catalysed hydrolysis of dimethyl succinates, aspartates, and glutamate provides (R) and (S) methyl esters enantioselectively.

PCILO and CNDO calculations on the specific interaction in two model analogs of BPA‐polycarbonate and a linear aliphatic polyster

AbstractPrevious investigations have given evidence of the existence of specific chemical interactions between poly(bisphenol‐A carbonate) (PC) and a number of linear aliphatic polyesters, with the consequent formation of compatible polymer alloys. Here we address the particular kind of specific interaction that takes place in these systems by performing a quantum‐mechanical study of the apparently most reasonable types of molecular interactions occurring in model compounds of the above polymers. Complete neglect of diffential overlap, (CNDO), in its CNDMEX version, and perturbative configuration using localized orbitals (PCILO) were the calculation schemes used on diphenyl carbonate (DPC) and dimethyl succinate (DMS), selected as models. It was found that, on a one‐to‐one basis, the DPC‐DMS system is energetically more stable than the individual separate molecules; on examination of the possible interaction sites for the two chemical species, the interaction between the ester group oxygen in one DMS molecule with one of the phenyl rings in DPC appears to be the most favorable type of molecular interrelation, even though hydrogen bond formation is also possible between the oxygen atoms in DPC and the methylene hydrogens in DMS. (The former interaction decreases the total energy of the system by 0.12 kcal/mol, more than the latter.)

Attractants for Oryzaephilus surinamensis (L.) (Coleoptera: Cucujidae): dimethyl succinate, glutarate, and adipate

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAttractants for Oryzaephilus surinamensis (L.) (Coleoptera: Cucujidae): dimethyl succinate, glutarate, and adipateKenneth L. Mikolajczak, Bruce W. Zilkowski, M. Zainul, A. Khan, Cecil R. Smith, and Wendell E. BurkholderCite this: J. Agric. Food Chem. 1985, 33, 6, 1029–1032Publication Date (Print):November 1, 1985Publication History Published online1 May 2002Published inissue 1 November 1985https://doi.org/10.1021/jf00066a005RIGHTS & PERMISSIONSArticle Views77Altmetric-Citations1LEARN 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 (571 KB) Get e-Alerts Get e-Alerts

Mutagenic investigation of flavourings: Dimethyl succinate, ethyl pyruvate and aconitic acid are negative in theSalmonella/mammalian‐microsome test

Three flavourings: dimethyl succinate, ethyl pyruvate and aconitic acid, commonly used in candy, beverages, and baked goods, were tested in the Salmonella/mammalian-microsome test. Tester strains were TA 1535, TA 100, TA 1537 and TA 98 and doses were 32, 160, 800, 4000 and 20 000 micrograms per plate. All tests were performed with and without the S9 fraction from Aroclor induced rat liver. None of the flavourings showed mutagenic potential. These results support the classification made by the Council of Europe, List I (1981).

Gluconeogenesis in rat hepatocytes from monomethyl succinate and other esters

Although little glucose is formed from succinate in rat hepatocytes, the rate of gluconeogenesis from monomethyl succinate approaches that from l-lactate. Dimethyl succinate is as good as monomethyl succinate at 5 m m, but not at 20 m m. Monoethyl fumarate and 4-methyl malate are only fair glucogenic substrates, but 1-methyl malate is another good substrate at high concentrations. The esters are apparently taken up either directly through the cell membrane, or by monocarboxylate transporters, and then hydrolyzed intracellularly by some esterase(s). This approach may permit the use of a wider range of substrates and inhibitors for the study of liver cell metabolism.

Purification and some properties of intracellular esterase from Pseudomonas fluorescens.

A novel esterase was found in Pseudomonas fluorescens cells and purified to homogeneity as determined by polyacrylamide gel electrophoresis. The esterase was extracted from the cells by freeze-thawing and hypotonic treatment. Purification was achieved by ammonium sulfate precipitation, followed by successive chromatographies on DEAE-cellulose and benzylamine-agarose and then electrophoresis. The enzyme catalyzed the hydrolysis of methyl esters, such as methyl butyrate, but its hydrolyzing activity decreased with increase in the chain length of the alcohol moiety, and it did not catalyze the hydrolysis of triacylglycerols, such as triacetin. In contrast, the enzyme acted on various acyl residues in a series of methyl esters, such as dimethyl succinate, methyl methacrylate, and dimethyl malate. The optimum pH for activity of this enzyme with methyl butyrate was 7.0-8.5. The enzyme was inhibited by phenylmethylsulfonylfluoride. Its molecular weight was estimated as 48,000 by molecular sieve electrophoresis and gel filtration on Sephadex G-150.