Tartaric acid

Low Molecular Weight Organic Acid Complexation Affects Antimony(III) Adsorption by Granular Ferric Hydroxide.[Pubmed:30969111]

Environ Sci Technol. 2019 Apr 10.

Antimony(III) mobility in natural aquatic environments is generally enhanced by dissolved organic matter. Tartaric acid is often used to form complexes with and stabilize dissolved Sb(III) in adsorption studies. However, competition between such low molecular organic acid complexation and adsorption of Sb(III) has received little attention, which prompted us to measure Sb(III) adsorption by iron oxyhydroxide adsorbents commonly used in water treatment plants. Sb K-edge X-ray absorption fine structure (EXAFS) spectra gave Sb-O and Sb-Fe distances and coordinations compatible with a bidentate binuclear inner-sphere complex with trigonal Sb(O,OH)3 polyhedra sharing corners with Fe(O,OH)6 octahedra, and a bidentate mononuclear inner-sphere complex but with Sb(O,OH)4 tetrahedra at alkaline pH. Experimental batch titration data were fitted using the charge-distribution multi-site surface complexation (CD-MUSIC) model, constrained by the EXAFS molecular level information and taking competitive effects by the organic ligand into consideration. The proportion adsorbed at acid-neutral pH decreased as the Sb(III) concentration increased. The CD-MUSIC adsorption model indicates that this was solely caused by strong competition from tartrate complexation in solution, which leads to adsorption constants higher than those derived without taking this competition into account. The adsorption model results allow for calculating a pe-pH predominance diagram using the USGS PhreePlot code. The study provides consistent surface complexation stability constants, allowing the new database to be used also to model reliably adsorption of toxic oxyanions in anoxic aqueous environments, for example to accurately simulate competition between Sb(III) and As(III).

Effect of sodium sulfite, tartaric acid, tannin, and glucose on rheological properties, release of aroma compounds, and color characteristics of red wine.[Pubmed:30956851]

Food Sci Biotechnol. 2018 Oct 15;28(2):395-403.

In this study, we evaluated the effect of addition of non-volatile compounds (sodium sulfite, Tartaric acid, tannin, and glucose) on the rheological properties, release of aroma compounds, and color of the red wine. While determining the rheological properties of the supplemented samples, non-Newtonian fluidic and shear-thinning behavior of samples was noticed. The viscosity of these samples was found in negative correlation with the dose of addition of various non-volatile substances. The aroma profile of red wine after additions showed the change in the release of the nine key aroma compounds. Among them ethyl hexanoate, phenylethyl alcohol, octanoic acid, diethyl succinate, and ethyl octanoate were profoundly increased. Further, the color of red wines was improved in the presence of Tartaric acid and tannin. Overall, supplementation of various substances during storage period of three different wines could enormously affect the sensory characteristics in a dose dependent manner.

(1)H NMR and LC-MS-based metabolomic approach for evaluation of the seasonality and viticultural practices in wines from Sao Francisco River Valley, a Brazilian semi-arid region.[Pubmed:30955648]

Food Chem. 2019 Aug 15;289:558-567.

Sao Francisco River Valley (SFRV) is a wine-producing semi-arid region in Brazil. Therefore, we used a (1)H NMR and UPLC-MS-based metabolomic approach coupled to chemometrics to evaluate the variability in Chenin Blanc and Syrah wines for two harvest seasons, two vine training system and six rootstocks. Overall, the secondary metabolites were influenced by the three factors studied, whereas the primary metabolites were only by the seasonality. Chenin Blanc wines made in December presented higher content of an unidentified carbohydrate. In Syrah wines, glycerol, Tartaric acid, succinic acid and 2,3-butanediol were greater in December, while proline and lactic acid were more abundant in July. For training system, caffeic acid derivatives were increased in wines produced from espalier. Lyre system increased phenolic compounds, organic acids and apocarotenoids. The effect of the rootstocks was less pronounced, affecting basically caffeic acid derivatives. Thus, we expect that our results may assist the winemakers to improve the SFRV wine quality.

Dual mode chip enantioselective express discrimination of chiral amines by the wettability-based mobile app and portable SERS measurements.[Pubmed:30945845]

ACS Sens. 2019 Apr 4.

Dual-mode functional chip for chiral sensing based on the mobile phone wettability measurements and portable Surface-enhanced Raman spectroscopy (SERS) is reported. The plasmon-active regular gold grating surface was covalently grafted with chiral recognition moieties, L- or D-enantiomers of Tartaric acid making possible stereoselective discrimination of chiral amines. Chiral sensing of amines includes two modes of analysis, performed subsequently on the one chip surface with portable instruments (mobile phone equipped with a camera and developed app <>, and portative Raman spectrometer). Firstly, the wettability changes, caused by enantioselective entrapping of chiral amines, are monitored and analyzed by our mobile phone app, allowing detection of the optical configuration and concentration of enantiomers with one order of magnitude accuracy. Secondly, SERS measurement on the same chip provides information about the chemical structure of entrapped amines and allows calculating the enantiomeric excess with great accuracy. The applicability of the developed chip is demonstrated on the variety of chiral amines, including the tyrosine, cysteine, dopamine (DOPA) and dextromethorphan in analytical solutions and in commercially available DOPA-containing drug. Moreover, we demonstrate that the chips could be regenerated and used repeatedly for at least 5 cycles.

Antioxidant Activities, Phenolic Profiles, and Organic Acid Contents of Fruit Vinegars.[Pubmed:30934715]

Antioxidants (Basel). 2019 Mar 27;8(4). pii: antiox8040078.

Fruit vinegars are popular condiments worldwide. Antioxidants and organic acids are two important components of the flavors and health benefits of fruit vinegars. This study aimed to test the antioxidant activities, phenolic profiles, and organic acid contents of 23 fruit vinegars. The results found that the 23 fruit vinegars varied in ferric-reducing antioxidant power (FRAP, 0.15(-)23.52 mumol Fe(II)/mL), Trolox equivalent antioxidant capacity (TEAC, 0.03(-)7.30 mumol Trolox/mL), total phenolic content (TPC, 29.64(-)3216.60 mg gallic acid equivalent/L), and total flavonoid content (TFC, 2.22(-)753.19 mg quercetin equivalent/L) values. Among the 23 fruit vinegars, the highest antioxidant activities were found in balsamic vinegar from Modena (Galletti), Aceto Balsamico di Modena (Monari Federzoni), red wine vinegar (Kuhne), and red wine vinegar (Galletti). In addition, polyphenols and organic acids might be responsible for the antioxidant activities of fruit vinegars. The most widely detected phenolic compounds in fruit vinegars were gallic acid, protocatechuic acid, chlorogenic acid, caffeic acid, and p-coumaric acid, with Tartaric acid, malic acid, lactic acid, citric acid, and succinic acid the most widely distributed organic acids. Overall, fruit vinegars are rich in polyphenols and organic acids and can be a good dietary source of antioxidants.

Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function.[Pubmed:30906077]

Tetrahedron Lett. 2018 Dec 26;59(52):4571-4573.

Linoleate triol esters are intermediates along the pathway of formation of the mammalian skin permeability barrier. In connection with the study of their involvement in barrier formation we required access to isomerically pure and defined samples of four linoleate triol esters. A common synthetic strategy was developed starting from isomeric alkynols derived from d-Tartaric acid and 2-deoxy-d-ribose.

Aggregation and dissolution of engineering nano Ag and ZnO pretreated with natural organic matters in the simulated lung biological fluids.[Pubmed:30903842]

Chemosphere. 2019 Mar 16;225:668-677.

The increasing application of engineered nanoparticles such as silver nanoparticles (nAg) and zinc oxide nanoparticles (nZnO), results in their accumulation in environmental media. The environmental natural organic matter (NOM) adsorbed by these nanoparticles may have great effects on the aggregation and dissolution of metall ions, which are interesting and important for the assessment of the inhalation risks of these airborne suspended NOM-coated nanoparticles to humans. Therefore, the aggregation and dissolution of nAg and nZnO pretreated with citric acid (CA), Tartaric acid (TA) and fulvic acid (FA) in simulated lung biological fluids (artificial lysosomal fluid (ALF) and Gamble Solution) were investigated. The surface properties, morphology and size of the NOM-treated ENPs changed, but the crystalline phase was relatively stable when observed using surface-enhanced Raman scattering, transmission electron microscope, and X-ray diffraction. NOM treatment had no significant influence on the particle size of NOM-treated nAg and nZnO except for a decrease in the size of CA-treated nAg, and it could not promote the aggregation of NOM-treated nAg and nZnO except for the aggregation of TA-treated nAg in Gamble Solution or TA-treated nZnO in ALF. CA- and FA-treatments promoted the release of Zn(2+) and Ag(+), respectively, while no promotion was observed after TA-treatment. Therefore, NOM affects the release of Zn(2+) and Ag(+) from NOM-treated nAg and nZnO but does not promote the aggregation of NOM-treated nAg and nZnO, which influences the inhalation risk-based assessment.

Functionalizing the surface of hydroxyapatite drug carrier with carboxylic acid groups to modulate the loading and release of curcumin nanoparticles.[Pubmed:30889767]

Mater Sci Eng C Mater Biol Appl. 2019 Jun;99:929-939.

This study has evaluated the effect of functionalizing surface charges of hydroxyapatite on the modulation of loading and release of curcumin nanoparticles. The increase in loading and release of curcumin nanoparticles indirectly translates to enhanced anti-cancer effect. Owing to the hydrophobic characteristics of curcumin which have resulted in low bioavailability in cancer cells, the engineering curcumin into nanoparticles is therefore a viable solution to overcomes its limitation. In order to maintain a sustained release profile of curcumin nanoparticles, curcumin nanoparticles were loaded (Cur-NPs) onto hydroxyapatite (HA) via physical adsorption. To regulate the adsorption capacity of Cur-NPs onto HA, we functionalized HA with different carboxylic acids (lactic acid, Tartaric acid and citric acid). The presence of carboxylic groups on HA significantly affected the binding and the release profile of Cur-NPs. The effects of Cur-NPs loaded HA were evaluated on breast cancer cell line (MCF-7), which included cell proliferation, cellular uptake of Cur-NPs, apoptosis and cell cycle analysis. The results showed that carboxylic acid-functionalized HA demonstrated higher anti-proliferating activity and time dependent cytoplasmic uptake of Cur-NPs in MCF-7 cells compared to unmodified HA. In addition, Cur-NPs loaded on functionalized HA induced higher apoptosis and cell cycle arrest in MCF-7 cells compared to unmodified HA. The present study indicates that the delivery of Cur-NPs to breast cancer using carboxylic acid-functionalized HA carrier could improve their anti-cancer activities.

Indirect synchronous fluorescence spectroscopy and direct high-performance thin-layer chromatographic methods for enantioseperation of zopiclone and determination of chiral-switching eszopiclone: Evaluation of thermodynamic quantities of chromatographic separation.[Pubmed:30859633]

Chirality. 2019 Mar 12.

Economic and enantioselective synchronous fluorescence spectroscopy and high-performance thin-layer chromatography methods have been developed and validated as per ICH guidelines for the separation of zopiclone enantiomers using L-(+)-Tartaric acid as a chiral selector, followed by determination of the chiral-switching eszopiclone. Synchronous fluorescence spectroscopy was successfully applied for chiral recognition of R & S enantiomers of zopiclone at lambda = 110 nm based on creating of diastereomeric complexes with 0.06M Tartaric acid in an aqueous medium containing 0.2M disodium hydrogen orthophosphate. Synchronous fluorescence intensities of eszopiclone were recorded at 296 nm in concentration range 0.2- to 4-mug/mL eszopiclone. High-performance thin-layer chromatography method depends on resolution of zopiclone enantiomers on achiral HPTLC silica-gel plates using acetonitrile:methanol:water (8:2:0.25, v/v/v) containing L-(+)-Tartaric acid as a chiral mobile-phase additive followed by densitometric measurements at 304 nm in concentration range of 1 to 10 mug/band of eszopiclone. The effect of chiral-selector concentration, pH, and temperature on the resolution have been studied and optimized for the proposed methods. The cited procedures were successfully applied to determine eszopiclone in commercial tablets of pure and racemic forms. Enantiomeric excess was evaluated using optical purity test and integrated peak area to describe the enantiomeric ratio. Thermodynamics of chromatographic separation, enthalpy, and entropy were evaluated using the Van't Hoff equation. The proposed methods were found to be selective for identification and determination of the eutomer in drug substances and products.

Low-molecular-weight organic acids impede the degradation of naphthol in iron oxides/persulfate systems: Implications for research experiments in pure conditions.[Pubmed:30852260]

Chemosphere. 2019 Feb 22;225:1-8.

Naphthols are industrial contaminants occurring widely in soils and waters. Remediation of organic pollutants can be done by chemical oxidation using persulfate. However, most research experiments testing degradation of organic pollutants have been done in ideal conditions, e.g. using a pure compound in pure water, and thus are weakly representative of real natural conditions where pollutants occur in complex mixtures of numerous organic compounds. Therefore we tested here the effect of the presence of small organic acids, as typical compounds occurring in natural media, on the degradation of 1-napthol with persulfate and iron oxides. Results show that organic acids decreased naphthol transformation by 3.7% for malic acid, 53.2% for Tartaric acid, 72.3% for citric acid and 77% for oxalic acids, in a magnetite/persulfate system during 10h. Meanwhile, the dissolved Fe species increased gradually with the reaction time; the highest concentration of Fe ions reached to approximately 18muML(-1) in aqueous phase. Electron paramagnetic resonance technique was applied to determine reactive oxygen species (ROS). The spin density of .OH, detected as the main ROS, decreased initially, followed by gradually increase, suggesting that organic acids might inhibit the degradation of 1-naphthol by competing with .OH. These findings disclose the high inhibition of the transformation by organic acids, and thus, more generally, imply that studies using only pure contaminants are weakly representative for remediation of real, natural samples.

Enantiomeric Tartaric Acid Production Using cis-Epoxysuccinate Hydrolase: History and Perspectives.[Pubmed:30841503]

Molecules. 2019 Mar 5;24(5). pii: molecules24050903.

Tartaric acid is an important chiral chemical building block with broad industrial and scientific applications. The enantioselective synthesis of l(+)- and d(-)-Tartaric acids has been successfully achieved using bacteria presenting cis-epoxysuccinate hydrolase (CESH) activity, while the catalytic mechanisms of CESHs were not elucidated clearly until very recently. As biocatalysts, CESHs are unique epoxide hydrolases because their substrate is a small, mirror-symmetric, highly hydrophilic molecule, and their products show very high enantiomeric purity with nearly 100% enantiomeric excess. In this paper, we review over forty years of the history, process and mechanism studies of CESHs as well as our perspective on the future research and applications of CESH in enantiomeric Tartaric acid production.

Concomitant cocrystal and salt: no interconversion in the solid state.[Pubmed:30833526]

Acta Crystallogr C Struct Chem. 2019 Mar 1;75(Pt 3):313-319.

A cocrystal and a molecular salt of beta-alanine and DL-Tartaric acid, C3H8NO2(+).C4H4O6(-), of the same chemical composition, were studied over a wide temperature range by single-crystal and powder X-ray diffraction. Neither the interconversion between the two phases nor any polymorphic transitions were observed in the temperature range from 100 K to the melting points. This contrasts with the solvent-mediated phase transition from the salt to the cocrystal in a slurry that has been documented earlier.

Quality characteristics of pork loin cured with green nitrite source and some organic acids.[Pubmed:30827821]

Meat Sci. 2019 Jun;152:141-145.

This study was conducted to improve the quality characteristics of cured meat with natural nitrite. Control and treatment were conducted as follows: nitrite free, marinated with sodium nitrite and ascorbic acid, marinated with only fermented spinach (FS), and marinated with FS adding ascorbic acid, malic acid, citric acid, and Tartaric acid. Treatments were pickled with regulated brine (8% salt and 0.08% nitrite). Cured meat with FS adding ascorbic acid, malic acid, and citric acid had higher redness values than sodium nitrite with ascorbic acid on cooked meat. There was a positive effect on lipid oxidation except for citric acid. Protein degradation appeared more in malic acid and Tartaric acid treatment than others. Residual nitrite level was lower when adding organic acids. Among various organic acid, ascorbic acid had the highest efficient on quality properties of cured meat. Thus, ascorbic acid was a proper ingredient when curing meat product.

Application of time-intensity analysis in model system submitted to homogenization.[Pubmed:30808232]

Food Sci Technol Int. 2019 Feb 26:1082013219833228.

The use of the high pressure homogenizer has been studied in fruit juices, but researches in model system for application in fruit nectar are scarce. Therefore, it is necessary to evaluate the application of these technologies and how the homogenization pressure (PH) can interfere in the sensorial profile of the samples. To prepare the solutions we used guar gum (0.1%), organic acids (0.3%), and sucrose (10%), which were later homogenized (0-control, 25 and 50 MPa) at 25 . The rheological behavior and the temporal profile of the samples were evaluated. The model systems presented pseudoplastic behavior without residual tension and were fitted to the Ostwald-de Waele model. The consistency index reduced and the flow behavior index increased with processing. Apparent viscosity also decreased due to homogenization. In the time-intensity sensorial analysis, it was observed that the samples differed among the evaluated parameters, demonstrating that the samples with Tartaric acid presented higher intensity for the sour taste. However, for sweetness, no change was observed. In the viscosity attribute, the model systems presented similar temporal profiles. Therefore, it was noted that the homogenization process favored a greater temporal profile of sour taste, making sensory perception more lasting in a model system for fruit nectar.

Effects of low-molecular weight organic acids on the transport of graphene oxide nanoparticles in saturated sand columns.[Pubmed:30798247]

Sci Total Environ. 2019 May 20;666:94-102.

The impact of low-molecular weight organic acids (LMWOAs) on the transport of graphene oxide (GO) nanoparticles in saturated quartz sand was investigated. The different LMWOAs such as acetic acid, glycolic acid, malonic acid, and Tartaric acid were used in experiments. The effects of LMWOAs on the transport of GO were markedly dependent upon organic acid species. In general, the transport enhancement effects followed the order of Tartaric acid>malonic acid>glycolic acid>acetic acid, the regular pattern might be related to amount and type of functional groups of LMWOAs. Additionally, the different enhanced ability of LMWOAs was determined by their molecular weight. In the presence of Na(+), the main deposition mechanism was ascribed to steric hindrance and competition between LMWOA and GO for deposition sites on grain surfaces under acidic conditions (i.e., pH4.0 and 5.0). Batch adsorption experiments indicated the extents of competitive adsorption between LMWOAs and GO on quartz sand. In addition, the DLVO theory was not applicable to describe the transport of GO in the presence of LMWOAs at pH5.0. Nevertheless, electrostatic and steric repulsion, existing between GO and sand grains, were the most important deposition mechanisms under the neutral condition (i.e., pH7.0). When Ca(2+) was the main cation in the background solution, the transport enhancement effects followed quite similar order to those of Na(+), mainly due to different complexing strength of organic acids.