WorldWideScience

Sample records for benzaldehyde

  1. Direct Spectrophotometric Assay for Benzaldehyde Lyase Activity

    Directory of Open Access Journals (Sweden)

    Dessy Natalia

    2011-01-01

    Full Text Available Benzaldehyde lyase from Pseudomonas fluorescens Biovar I. (BAL, EC 4.1.2.38 is a versatile catalyst for the organic synthesis of chiral α-hydroxy ketones. To allow fast assessment of enzyme activity, a direct spectrophotometric assay is desirable. Here, a new robust and easy-to-handle assay based on UV absorption is presented. The assay developed is based on the ligation of the α-hydroxy ketone (R-2,2′-furoin from 2-furaldehyde. A robust assay with direct monitoring of the product is facilitated with a convenient concentration working range minimising experimental associated with low concentrations.

  2. Adsorption, mobility, and dimerization of benzaldehyde on Pt(111)

    DEFF Research Database (Denmark)

    Rasmussen, Anton Michael Havelund; Hammer, Bjørk

    2012-01-01

    Building on results for the adsorption of benzene on Pt(111), the adsorption of benzaldehyde is investigated using density functional theory. Benzaldehyde is found to chemisorb preferentially with its aromatic ring in the flat-lying bridge geometry that is also preferred for benzene. Across the i...

  3. Benzaldehyde suppresses murine allergic asthma and rhinitis.

    Science.gov (United States)

    Jang, Tae Young; Park, Chang-Shin; Kim, Kyu-Sung; Heo, Min-Jeong; Kim, Young Hyo

    2014-10-01

    To evaluate the antiallergic effects of oral benzaldehyde in a murine model of allergic asthma and rhinitis, we divided 20 female BALB/c mice aged 8-10 weeks into nonallergic (intraperitoneally sensitized and intranasally challenged to normal saline), allergic (intraperitoneally sensitized and intranasally challenged to ovalbumin), and 200- and 400-mg/kg benzaldehyde (allergic but treated) groups. The number of nose-scratching events in 10 min, levels of total and ovalbumin-specific IgE in serum, differential counts of inflammatory cells in bronchoalveolar lavage (BAL) fluid, titers of Th2 cytokines (IL-4, IL-5, IL-13) in BAL fluid, histopathologic findings of lung and nasal tissues, and expressions of proteins involved in apoptosis (Bcl-2, Bax, caspase-3), inflammation (COX-2), antioxidation (extracellular SOD, HO-1), and hypoxia (HIF-1α, VEGF) in lung tissue were evaluated. The treated mice had significantly fewer nose-scratching events, less inflammatory cell infiltration in lung and nasal tissues, and lower HIF-1α and VEGF expressions in lung tissue than the allergic group. The number of eosinophils and neutrophils and Th2 cytokine titers in BAL fluid significantly decreased after the treatment (Pbenzaldehyde exerts antiallergic effects in murine allergic asthma and rhinitis, possibly through inhibition of HIF-1α and VEGF.

  4. Benzaldehyde dehydrogenase from chitosan-treated Sorbus aucuparia cell cultures.

    Science.gov (United States)

    Gaid, Mariam M; Sircar, Debabrata; Beuerle, Till; Mitra, Adinpunya; Beerhues, Ludger

    2009-09-01

    Cell cultures of Sorbus aucuparia respond to the addition of chitosan with the accumulation of the biphenyl phytoalexin aucuparin. The carbon skeleton of this inducible defense compound is formed by biphenyl synthase (BIS) from benzoyl-CoA and three molecules of malonyl-CoA. The formation of benzoyl-CoA proceeds via benzaldehyde as an intermediate. Benzaldehyde dehydrogenase (BD), which converts benzaldehyde into benzoic acid, was detected in cell-free extracts from S. aucuparia cell cultures. BD and BIS were induced by chitosan treatment. The preferred substrate for BD was benzaldehyde (K(m)=49 microM). Cinnamaldehyde and various hydroxybenzaldehydes were relatively poor substrates. BD activity was strictly dependent on the presence of NAD(+) as a cofactor (K(m)=67 microM).

  5. The determination of furaldehyde and benzaldehyde in plum brandy

    Directory of Open Access Journals (Sweden)

    Rajković Miloš B.

    2005-01-01

    Full Text Available Among all alcohol liqueurs, brandies from drupaceous plants are characterized with the highest level of hydro cyanic acid, benzaldehyde and ethylcarbamate. In fruit brandies ethylcarbamate mainly originates from hydro cyanic acid during the processes of alcohol fermentation of crushed fruit and its preservation, distillation and ripening of the brandy. Hydro cyanic acid and benzaldehyde arise from the hydrolysis of amygdaline that is found exist in the heart of fruit stones and seeds, as well as from the hydrolysis of prunasine from the skin and flesh of drupaceous plants. The content of amygdaline and prunazine depends on the type of fruit, which corresponds to the potential content of hydro cyanic acid and benzaldehyde in the brandy that corresponds the stoichiometric ratio 1:3.94. The content of the aldehydes: furfural and benzaldehyde in plum brandy, strong plum brandy, young brandy, of domestic production in the various regions of Serbia were analyzed in this paper.

  6. Involvement of snapdragon benzaldehyde dehydrogenase in benzoic acid biosynthesis.

    Science.gov (United States)

    Long, Michael C; Nagegowda, Dinesh A; Kaminaga, Yasuhisa; Ho, Kwok Ki; Kish, Christine M; Schnepp, Jennifer; Sherman, Debra; Weiner, Henry; Rhodes, David; Dudareva, Natalia

    2009-07-01

    Benzoic acid (BA) is an important building block in a wide spectrum of compounds varying from primary metabolites to secondary products. Benzoic acid biosynthesis from L-phenylalanine requires shortening of the propyl side chain by two carbons, which can occur via a beta-oxidative pathway or a non-beta-oxidative pathway, with benzaldehyde as a key intermediate. The non-beta-oxidative route requires benzaldehyde dehydrogenase (BALDH) to convert benzaldehyde to BA. Using a functional genomic approach, we identified an Antirrhinum majus (snapdragon) BALDH, which exhibits 40% identity to bacterial BALDH. Transcript profiling, biochemical characterization of the purified recombinant protein, molecular homology modeling, in vivo stable isotope labeling, and transient expression in petunia flowers reveal that BALDH is capable of oxidizing benzaldehyde to BA in vivo. GFP localization and immunogold labeling studies show that this biochemical step occurs in the mitochondria, raising a question about the role of subcellular compartmentalization in BA biosynthesis.

  7. Fluorescence Quenching of Benzaldehyde in Water by Hydrogen Atom Abstraction.

    Science.gov (United States)

    Fletcher, Katharyn; Bunz, Uwe H F; Dreuw, Andreas

    2016-09-01

    We computed the mechanism of fluorescence quenching of benzaldehyde in water through relaxed potential energy surface scans. Time-dependent density functional theory calculations along the protonation coordinate from water to benzaldehyde reveal that photoexcitation to the bright ππ* (S3 ) state is immediately followed by ultrafast decay to the nπ* (S1 ) state. Evolving along this state, benzaldehyde (BA) abstracts a hydrogen atom, resulting in a BAH(.) and OH(.) radical pair. Benzaldehyde does not act as photobase in water, but abstracts a hydrogen atom from a nearby solvent molecule. The system finally decays back to the ground state by non-radiative decay and an electron transfers back to the OH(.) radical. Proton transfer from BAH(+) to OH(-) restores the initial situation, BA in water.

  8. Adsorption of Benzaldehyde on Granular Activated Carbon: Kinetics, Equilibrium, and Thermodynamic

    OpenAIRE

    Rajoriya, R.K.; Prasad, B; Mishra, I.M.; Wasewar, K. L.

    2007-01-01

    Adsorption isotherms of benzaldehyde from aqueous solutions onto granular activated carbon have been determined and studied the effect of dosage of granular activated carbon, contact time, and temperature on adsorption. Optimum conditions for benzaldehyde removal were found adsorbent dose 4 g l–1 of solution and equilibrium time t 4 h. Percent removal of benzaldehyde increases with the increase in adsorbent dose for activated carbon, however, it decreases with increase in benzaldehyde m...

  9. The Kinetic Behavior of Benzaldehyde under Hydrothermal Conditions

    Science.gov (United States)

    Fecteau, K.; Gould, I.; Hartnett, H. E.; Williams, L. B.; Shock, E.

    2013-12-01

    Aldehydes represent an intermediate redox state between alcohols and carboxylic acids and are likely intermediates in the transformation of organic compounds in natural systems. We have conducted kinetic studies of a model aldehyde, benzaldehyde, in high-temperature water (250-350 °C, saturation pressure) in clear fused quartz (CFQ) autoclaves. Under these conditions, benzaldehyde is observed to undergo a disproportionation reaction to benzyl alcohol and benzoic acid reminiscent of the base-catalyzed Cannizzaro reaction known to occur at cooler temperatures. Benzene is also produced via decarbonylation of the aldehyde. We have obtained pseudo second-order rate constants for the decomposition of benzaldehyde at 250, 300, and 350 °C. Rates derived via repeated heating phases and subsequent quantitative 13C-NMR spectroscopy of a single NMR-compatible CFQ tube containing isotopically labeled benzaldehyde are consistent with those obtained by analysis of product suites from individual timed experiments via gas chromatography. Arrhenius parameters for these rate constants are consistent with published values for the reaction under supercritical conditions from one study (Tsao et al. 1992) yet the pre-exponential factor is approximately 7 orders of magnitude smaller than that derived from another study (Ikushima et al. 2001). Moreover, fitting our rate constants with the Eyring equation yields an entropy of activation (ΔS‡) of -26.6 kcal mol-1 K-1, which is consistent for a bimolecular transition state at the rate-limiting step. In contrast, the rates of Ikushima et al. yield a positive value of ΔS‡, which is inconsistent with the putative mechanism for the reaction. The linear Arrhenius behavior of the decomposition of benzaldehyde from high-temperature liquid to supercritical conditions demonstrates the potential for extrapolating experimentally derived rates of reactions for organic functional group transformations to conditions where diagenesis, alteration

  10. Infrared Spectra and Hydrogen Bonds of Biologically Active Benzaldehydes

    Science.gov (United States)

    Tolstorozhev, G. B.; Skornyakov, I. V.; Belkov, M. V.; Shimko, A. N.; Shadyro, O. I.; Brinkevich, S. D.; Samovich, S. N.

    2013-09-01

    IR-Fourier spectra of solutions and crystals of biologically active benzaldehyde derivatives were studied. Specific features of the formation of intra- and intermolecular hydrogen bonds were analyzed. Spectral signatures that characterized participation of the hydroxyl OH group and also the OCH3 and C=O groups in the formation of intramolecular hydrogen bonds of the three different types O-H···O-H, O-H···O-CH3, and O-H···O=C were revealed. Intramolecular hydrogen bonds of the types O-H···O-H and O-H···O-CH3 were absent for benzaldehyde derivatives in the crystal phase. Only hydroxyl and carbonyl groups participated in intermolecular interactions. This resulted in the formation of linear intermolecular dimers. Seven various configurations of the linear dimers were identified in solutions and crystals.

  11. Biomass pyrolysis: Thermal decomposition mechanisms of furfural and benzaldehyde

    Science.gov (United States)

    Vasiliou, AnGayle K.; Kim, Jong Hyun; Ormond, Thomas K.; Piech, Krzysztof M.; Urness, Kimberly N.; Scheer, Adam M.; Robichaud, David J.; Mukarakate, Calvin; Nimlos, Mark R.; Daily, John W.; Guan, Qi; Carstensen, Hans-Heinrich; Ellison, G. Barney

    2013-09-01

    The thermal decompositions of furfural and benzaldehyde have been studied in a heated microtubular flow reactor. The pyrolysis experiments were carried out by passing a dilute mixture of the aromatic aldehydes (roughly 0.1%-1%) entrained in a stream of buffer gas (either He or Ar) through a pulsed, heated SiC reactor that is 2-3 cm long and 1 mm in diameter. Typical pressures in the reactor are 75-150 Torr with the SiC tube wall temperature in the range of 1200-1800 K. Characteristic residence times in the reactor are 100-200 μsec after which the gas mixture emerges as a skimmed molecular beam at a pressure of approximately 10 μTorr. Products were detected using matrix infrared absorption spectroscopy, 118.2 nm (10.487 eV) photoionization mass spectroscopy and resonance enhanced multiphoton ionization. The initial steps in the thermal decomposition of furfural and benzaldehyde have been identified. Furfural undergoes unimolecular decomposition to furan + CO: C4H3O-CHO (+ M) → CO + C4H4O. Sequential decomposition of furan leads to the production of HC≡CH, CH2CO, CH3C≡CH, CO, HCCCH2, and H atoms. In contrast, benzaldehyde resists decomposition until higher temperatures when it fragments to phenyl radical plus H atoms and CO: C6H5CHO (+ M) → C6H5CO + H → C6H5 + CO + H. The H atoms trigger a chain reaction by attacking C6H5CHO: H + C6H5CHO → [C6H6CHO]* → C6H6 + CO + H. The net result is the decomposition of benzaldehyde to produce benzene and CO.

  12. [A new benzaldehyde from aerial part of Rehmannia glutinosa].

    Science.gov (United States)

    Zou, Yan; Zhang, Lei; Xu, Jie-kun; Cheng, Qian; Ye, Xian-sheng; Li, Ping; Zhang, Wei-ku; Li, Yong-ji

    2015-04-01

    A new benzaldehyde, 3-hydroxy-4-(4-(2-hydroxyethyl) phenoxy) henzaldehyde(1), together with six known compounds, including isovanillic acid(2), pyrocatechol(3), glutinosalactone A(4), chrysoeriol(5), apigenin(6) and luteolin(7) were isolated from aerial part of Rehmannia glutinosa. The compounds were isolated by macroporous resin, silica gel, Sephadex LH-20 and HPLC chromatographies. The chemical structures of 1-7 were elucidated on the basis of spectral analysis (MS, 1D NMR and 2D NMR).

  13. Biomass pyrolysis: thermal decomposition mechanisms of furfural and benzaldehyde.

    Science.gov (United States)

    Vasiliou, AnGayle K; Kim, Jong Hyun; Ormond, Thomas K; Piech, Krzysztof M; Urness, Kimberly N; Scheer, Adam M; Robichaud, David J; Mukarakate, Calvin; Nimlos, Mark R; Daily, John W; Guan, Qi; Carstensen, Hans-Heinrich; Ellison, G Barney

    2013-09-14

    The thermal decompositions of furfural and benzaldehyde have been studied in a heated microtubular flow reactor. The pyrolysis experiments were carried out by passing a dilute mixture of the aromatic aldehydes (roughly 0.1%-1%) entrained in a stream of buffer gas (either He or Ar) through a pulsed, heated SiC reactor that is 2-3 cm long and 1 mm in diameter. Typical pressures in the reactor are 75-150 Torr with the SiC tube wall temperature in the range of 1200-1800 K. Characteristic residence times in the reactor are 100-200 μsec after which the gas mixture emerges as a skimmed molecular beam at a pressure of approximately 10 μTorr. Products were detected using matrix infrared absorption spectroscopy, 118.2 nm (10.487 eV) photoionization mass spectroscopy and resonance enhanced multiphoton ionization. The initial steps in the thermal decomposition of furfural and benzaldehyde have been identified. Furfural undergoes unimolecular decomposition to furan + CO: C4H3O-CHO (+ M) → CO + C4H4O. Sequential decomposition of furan leads to the production of HC≡CH, CH2CO, CH3C≡CH, CO, HCCCH2, and H atoms. In contrast, benzaldehyde resists decomposition until higher temperatures when it fragments to phenyl radical plus H atoms and CO: C6H5CHO (+ M) → C6H5CO + H → C6H5 + CO + H. The H atoms trigger a chain reaction by attacking C6H5CHO: H + C6H5CHO → [C6H6CHO]* → C6H6 + CO + H. The net result is the decomposition of benzaldehyde to produce benzene and CO.

  14. Serotonin mediates a learned increase in attraction to high concentrations of benzaldehyde in aged C. elegans.

    Science.gov (United States)

    Tsui, David; van der Kooy, Derek

    2008-11-01

    We utilized olfactory-mediated chemotaxis in Caenorhabditis elegans to examine the effect of aging on information processing and animal behavior. Wild-type (N2) young adults (day 4) initially approach and eventually avoid a point source of benzaldehyde. Aged adult animals (day 7) showed a stronger initial approach and a delayed avoidance to benzaldehyde compared with young adults. This delayed avoidance is due to an increased attraction rather than a decreased avoidance to benzaldehyde because (1) aged odr-3 mutants that are defective in odor attraction showed no delayed benzaldehyde avoidance, and (2) the delay in avoidance was also observed with another attractant diacetyl, but not the repellent octanol. Interestingly, the stronger expression of attractive behavior was only observed at benzaldehyde concentrations of 1% or higher. When worms were grown on nonbacterial growth media instead of Escherichia coli, thus removing the contingency between odors released from the food and the food itself, the increase in attraction to benzaldehyde disappeared. The increased attraction recovered after reinitiating the odor-food contingency by returning animals to E. coli food or supplementing axenic media with benzaldehyde. Moreover, serotonin-deficient mutants showed a deficit in the age-enhanced attraction. These results suggest that the increased attraction to benzaldehyde in aged worms is (1) serotonin mediated, (2) specific to high concentration of odorants, and (3) dependent on a learned association of odor metabolites with the presence of food. We propose that associative learning may selectively modify pathways at or downstream from a low-affinity olfactory receptor.

  15. Cherry-flavoured electronic cigarettes expose users to the inhalation irritant, benzaldehyde.

    Science.gov (United States)

    Kosmider, Leon; Sobczak, Andrzej; Prokopowicz, Adam; Kurek, Jolanta; Zaciera, Marzena; Knysak, Jakub; Smith, Danielle; Goniewicz, Maciej L

    2016-04-01

    Many non-cigarette tobacco products, including e-cigarettes, contain various flavourings, such as fruit flavours. Although many flavourings used in e-cigarettes are generally recognised as safe when used in food products, concerns have been raised about the potential inhalation toxicity of these chemicals. Benzaldehyde, which is a key ingredient in natural fruit flavours, has been shown to cause irritation of respiratory airways in animal and occupational exposure studies. Given the potential inhalation toxicity of this compound, we measured benzaldehyde in aerosol generated in a laboratory setting from flavoured e-cigarettes purchased online and detected benzaldehyde in 108 out of 145 products. The highest levels of benzaldehyde were detected in cherry-flavoured products. The benzaldehyde doses inhaled with 30 puffs from flavoured e-cigarettes were often higher than doses inhaled from a conventional cigarette. Levels in cherry-flavoured products were >1000 times lower than doses inhaled in the workplace. While e-cigarettes seem to be a promising harm reduction tool for smokers, findings indicate that using these products could result in repeated inhalation of benzaldehyde, with long-term users risking regular exposure to the substance. Given the uncertainty surrounding adverse health effects stemming from long-term inhalation of flavouring ingredients such as benzaldehyde, clinicians need to be aware of this emerging risk and ask their patients about use of flavoured e-cigarettes.

  16. Polycondensation of pyrrole and benzaldehyde catalyzed by Maghnite–H+

    Directory of Open Access Journals (Sweden)

    2007-07-01

    Full Text Available Rapid synthesis of poly[(pyrrole-2,5-diyl-co-(benzylidene] was achieved under microwave irradiation via the condensation of pyrrole and benzaldehyde in 1,2-dichloroethane using acid exchanged montmorillonite clay called Maghnite–H+ (Mag–H+ as an efficient catalyst. The effect of the amount of catalyst and of time on the polymerization yield and on the viscosity of the polymers was studied. Compared with conventional static interfacial polymerization, the microwave-radiation polymerization reaction proceeded rapidly and was completed within 35 s. The conjugated polymer was characterized by means of 1H-NMR, X-ray diffraction, FT-IR spectroscopy and AFM. The X-ray data showed the presence of a backbone form of the [(pyrrole-2,5-diyl-co-(benzylidene] formed.

  17. Explorations of Crystalline Effects on 4-(Benzyloxy)Benzaldehyde Properties

    Science.gov (United States)

    Harismah, Kun; Ozkendir, O. Murat; Mirzaei, Mahmoud

    2015-12-01

    The properties of 4-(benzyloxy)benzaldehyde (BBA), as a pharmaceutically important compound, have been investigated through the density functional theory (DFT) calculations. The properties of original crystalline and optimised gaseous structures have been evaluated to recognise the crystalline effects. In addition to the structural properties, nuclear magnetic resonance (NMR) properties have also been evaluated for both investigated systems to better detect the effects in atomic levels. The results indicated that the structural shape of BBA is significantly changed in the optimised gaseous system, showing significant crystalline effects on the geometrical positions. Moreover, the magnitudes for energies and dipole moments indicate notable effects on the electronic properties. The evaluated NMR properties also show that the atoms of aromatic systems detect significant changes more than the atoms of aliphatic systems in the investigated BBA. And finally, the oxygen bridge atom plays a dominant role in combining two benzene rings of BBA.

  18. Bioproduction of benzaldehyde in a solid-liquid two-phase partitioning bioreactor using Pichia pastoris.

    Science.gov (United States)

    Jain, Ashu N; Khan, Tanya R; Daugulis, Andrew J

    2010-11-01

    The bioproduction of benzaldehyde from benzyl alcohol using Pichia pastoris was examined in a solid-liquid two-phase partitioning bioreactor (TPPB) to reduce substrate and product inhibition. Rational polymer selection identified Elvax 40W as an effective sequestering phase, possessing partition coefficients for benzyl alcohol and benzaldehyde of 3.5 and 35.4, respectively. The use of Elvax 40W increased the overall mass of benzaldehyde produced by approx. 300% in a 5 l bioreactor, relative to a single phase biotransformation. The two-phase system had a molar yield of 0.99, indicating that only minor losses occurred. These results provide a promising starting point for solid-liquid TPPBs to enhance benzaldehyde production, and suggest that multiple, targeted polymers may provide relief for transformations characterized by multiple inhibitory substrates/product/by-products.

  19. Benzaldehyde as an insecticidal, antimicrobial, and antioxidant compound produced by Photorhabdus temperata M1021.

    Science.gov (United States)

    Ullah, Ihsan; Khan, Abdul Latif; Ali, Liaqat; Khan, Abdur Rahim; Waqas, Muhammad; Hussain, Javid; Lee, In-Jung; Shin, Jae-Ho

    2015-02-01

    The Photorhabdus temperata M1021 secretes toxic compounds that kill their insect hosts by arresting immune responses. Present study was aimed to purify the insecticidal and antimicrobial compound(s) from the culture extract of P. temperata M1021 through bioassay guided fractionation. An ethyl acetate (EtOAc) extract of the P. temperata M1021 exhibited 100% mortality in Galleria mellonella larvae within 72 h. In addition, EtOAc extract and bioactive compound 1 purified form the extract through to column chromatography, showed phenol oxidase inhibition up to 60% and 80% respectively. The analysis of (1)H and (13)C NMR spectra revealed the identity of pure compound as "benzaldehyde". The benzaldehyde showed insecticidal activity against G. mellonella in a dose-dependent manner and 100% insect mortality was observed at 108 h after injection of 8 mM benzaldehyde. In a PO inhibition assay, 4, 6, and 8 mM concentrations of benzaldehyde were found to inhibit PO activity about 15%, 42%, and 80% respectively. In addition, nodule formation was significantly (P benzaldehyde as compare to control. Moreover, benzaldehyde was found to have great antioxidant activity and maximum antioxidant activity was 52.9% at 8 mM benzaldehyde as compare to control. Antimicrobial activity was assessed by MIC values ranged from 6 mM 10 mM for bacterial strains and 8 mM to 10 mM for fungal strains. The results suggest that benzaldehyde could be applicable for developing novel insecticide for agriculture use.

  20. Influence of Photosensitive Group Concentration on Birefringence Induced in Benzaldehyde Polymers

    Science.gov (United States)

    Mahilny, U. V.; Stankevich, A. I.; Trofimova, A. V.

    2014-01-01

    Induction of optical anisotropy in benzaldehyde polymer layers by linearly polarized UV radiation was investigated experimentally. Negative dichroism in absorption spectra and strong negative birefringence (-2 · 10-3) were related to the presence of an oriented ensemble of residual benzaldehyde groups. The thermal stability of photoinduced birefringence at high photosensitive group concentration was associated with a high density of photocross-links formed between macromolecules.

  1. Mechanism of benzaldehyde lyase studied via thiamin diphosphate-bound intermediates and kinetic isotope effects.

    Science.gov (United States)

    Chakraborty, Sumit; Nemeria, Natalia; Yep, Alejandra; McLeish, Michael J; Kenyon, George L; Jordan, Frank

    2008-03-25

    Direct spectroscopic observation of thiamin diphosphate-bound intermediates was achieved on the enzyme benzaldehyde lyase, which carries out reversible and highly enantiospecific conversion of ( R)-benzoin to benzaldehyde. The key enamine intermediate could be observed at lambda max 393 nm in the benzoin breakdown direction and in the decarboxylase reaction starting with benzoylformate. With benzaldehyde as substrate, no intermediates could be detected, only formation of benzoin at 314 nm. To probe the rate-limiting step in the direction of ( R)-benzoin synthesis, the (1)H/ (2)H kinetic isotope effect was determined for benzaldehyde labeled at the aldehyde position and found to be small (1.14 +/- 0.03), indicating that ionization of the C2alphaH from C2alpha-hydroxybenzylthiamin diphosphate is not rate limiting. Use of the alternate substrates benzoylformic and phenylpyruvic acids (motivated by the observation that while a carboligase, benzaldehyde lyase could also catalyze the slow decarboxylation of 2-oxo acids) enabled the observation of the substrate-thiamin covalent intermediate via the 1',4'-iminopyrimidine tautomer, characteristic of all intermediates with a tetrahedral C2 substituent on ThDP. The reaction of benzaldehyde lyase with the chromophoric substrate analogue ( E)-2-oxo-4(pyridin-3-yl)-3-butenoic acid and its decarboxylated product ( E)-3-(pyridine-3-yl)acrylaldehyde enabled the detection of covalent adducts with both. Neither adduct underwent further reaction. An important finding of the studies is that all thiamin-related intermediates are in a chiral environment on benzaldehyde lyase as reflected by their circular dichroism signatures.

  2. delta(13)C and delta(2)H isotope ratios in amphetamine synthesized from benzaldehyde and nitroethane.

    Science.gov (United States)

    Collins, Michael; Salouros, Helen; Cawley, Adam T; Robertson, James; Heagney, Aaron C; Arenas-Queralt, Andrea

    2010-06-15

    Previous work in these laboratories and by Butzenlechner et al. and Culp et al. has demonstrated that the delta(2)H isotope value of industrial benzaldehyde produced by the catalytic oxidation of toluene is profoundly positive, usually in the range +300 per thousand to +500 per thousand. Synthetic routes leading to amphetamine, methylamphetamine or their precursors and commencing with such benzaldehyde may be expected to exhibit unusually positive delta(2)H values. Results are presented for delta(13)C and delta(2)H isotope values of 1-phenyl-2-nitropropene synthesized from an industrial source of benzaldehyde, having a positive delta(2)H isotope value, by a Knoevenagel condensation with nitroethane. Results are also presented for delta(13)C and delta(2)H isotope values for amphetamine prepared from the resulting 1-phenyl-2-nitropropene. The values obtained were compared with delta(13)C and delta(2)H isotope values obtained for an amphetamine sample prepared using a synthetic route that did not involve benzaldehyde. Finally, results are presented for samples of benzaldehyde, 1-phenyl-2-nitropropene and amphetamine that had been seized at a clandestine amphetamine laboratory.

  3. β-Cyclodextrin Promoted Oxidation of Cinnamaldehyde to Natural Benzaldehyde in Water

    Institute of Scientific and Technical Information of China (English)

    陈鸿雁; 纪红兵

    2011-01-01

    A facile and efficient procedure has been developed systematically for the oxidative cleavage of cinna-maldehyde to benzaldehyde by sodium hypochlorite with water as the only solvent in the presence of β-cyclodextrin (abbreviated as β-CD). Different factors influencing cinnamaldehyde oxidation e.g. reaction temperature, the amount of catalyst and oxidant, have been investigated. The yield of benzaldehyde reaches 76% under the optimum conditions (333 K, 4 h, molar ratio of cinnamaldehyde to β-CD is 1:1). Furthermore, a feasible reaction mecha-nism including the formation of benzaldehyde and the two main byproducts (phenylacetaldehyde and epoxide of cinnamaldehyde) has been proposed.

  4. Benzaldehyde in cherry flavour as a precursor of benzene formation in beverages.

    Science.gov (United States)

    Loch, Christine; Reusch, Helmut; Ruge, Ingrid; Godelmann, Rolf; Pflaum, Tabea; Kuballa, Thomas; Schumacher, Sandra; Lachenmeier, Dirk W

    2016-09-01

    During sampling and analysis of alcohol-free beverages for food control purposes, a comparably high contamination of benzene (up to 4.6μg/L) has been detected in cherry-flavoured products, even when they were not preserved using benzoic acid (which is a known precursor of benzene formation). There has been some speculation in the literature that formation may occur from benzaldehyde, which is contained in natural and artificial cherry flavours. In this study, model experiments were able to confirm that benzaldehyde does indeed degrade to benzene under heating conditions, and especially in the presence of ascorbic acid. Analysis of a large collective of authentic beverages from the market (n=170) further confirmed that benzene content is significantly correlated to the presence of benzaldehyde (r=0.61, pbenzaldehyde in combination with ascorbic acid should be avoided.

  5. Adsorption of benzaldehyde at the surface of ice, studied by experimental method and computer simulation.

    Science.gov (United States)

    Petitjean, Mélanie; Hantal, György; Chauvin, Coline; Mirabel, Philippe; Le Calvé, Stéphane; Hoang, Paul N M; Picaud, Sylvain; Jedlovszky, Pál

    2010-06-15

    Adsorption study of benzaldehyde on ice surfaces is performed by combining experimental and theoretical approaches. The experiments are conducted over the temperature range 233-253 K using a coated wall flow tube coupled to a mass spectrometric detector. Besides the experimental way, the adsorption isotherm is also determined by performing a set of grand canonical Monte Carlo simulations at 233 K. The experimental and calculated adsorption isotherms show a very good agreement within the corresponding errors. Besides, both experimental and theoretical studies permit us to derive the enthalpy of adsorption of benzaldehyde on ice surfaces DeltaH(ads), which are in excellent agreement: DeltaH(ads) = -61.4 +/- 9.7 kJ/mol (experimental) and DeltaH(ads) = -59.4 +/- 5.1 kJ/mol (simulation). The obtained results indicate a much stronger ability of benzaldehyde of being adsorbed at the surface of ice than that of small aliphatic aldehydes, such as formaldehyde or acetaldehyde. At low surface coverages the adsorbed molecules exclusively lie parallel with the ice surface. With increasing surface coverage, however, the increasing competition of the adsorbed molecules for the surface area to be occupied leads to the appearance of two different perpendicular orientations relative to the surface. In the first orientation, the benzaldehyde molecule turns its aldehyde group toward the ice phase, and, similarly to the molecules in the lying orientation, forms a hydrogen bond with a surface water molecule. In the other perpendicular orientation the aldehyde group turns to the vapor phase, and its O atom interacts with the delocalized pi system of the benzene ring of a nearby lying benzaldehyde molecule of the second molecular layer. In accordance with this observed scenario, the saturated adsorption layer, being stable in a roughly 1 kJ/mol broad range of chemical potentials, contains, besides the first molecular layer, also traces of the second molecular layer of adsorbed

  6. A kinetic model for toluene oxidation comprising benzylperoxy benzoate ester as reactive intermediate in the formation of benzaldehyde

    NARCIS (Netherlands)

    Hoorn, J.A.A.; Alsters, P. L.; Versteeg, G. F.

    2005-01-01

    During the oxidation of toluene under semibatch conditions, the formation of benzyl alcohol is initially equal to the rate of formation of benzaldehyde. As the overall conversion increases the benzyl alcohol concentration at first decreases much faster than benzaldehyde, but this decrease slows down

  7. A Kinetic Model for Toluene Oxidation Comprising Benzylperoxy Benzoate Ester as Reactive Intermediate in the Formation of Benzaldehyde

    NARCIS (Netherlands)

    Hoorn, J.A.A.; Alsters, P.L.; Versteeg, G.F.

    2005-01-01

    During the oxidation of toluene under semibatch conditions, the formation of benzyl alcohol is initially equal to the rate of formation of benzaldehyde. As the overall conversion increases the benzyl alcohol concentration at first decreases much faster than benzaldehyde, but this decrease slows down

  8. GRAFTED STYRENE-DIVINYLBENZENE COPOLYMERS CONTAINING BENZALDEHYDES AND THEIR WITTIG REACTIONS WITH VARIOUS PHOSPHONIUM SALTS

    Institute of Scientific and Technical Information of China (English)

    Adriana Popa; Gheorghe Ilia; Aurelia Pascariu; Smaranda Iliescu; Nicoleta Plesu

    2005-01-01

    A chloromethylated styrene-divinylbenzene copolymer support system functionalized with 4-benzaldehyde and 2-benzaldehyde was prepared. The degree of functionalization with aldehyde groups is well suited for the subsequent use of the products as Wittig reagents. The polymer bound aldehyde was reacted with Wittig reagents to give olefin groups grafted on styrene-divinylbenzene copolymers. The reactions were carried out in phase transfer catalysis conditions. A simple procedure for the calculation of the degree of functionalization and the statistical modeling of the structural repetitive unit of the copolymer are reported.

  9. Antifungal activity of redox-active benzaldehydes that target cellular antioxidation

    Directory of Open Access Journals (Sweden)

    Mahoney Noreen

    2011-05-01

    Full Text Available Abstract Background Disruption of cellular antioxidation systems should be an effective method for control of fungal pathogens. Such disruption can be achieved with redox-active compounds. Natural phenolic compounds can serve as potent redox cyclers that inhibit microbial growth through destabilization of cellular redox homeostasis and/or antioxidation systems. The aim of this study was to identify benzaldehydes that disrupt the fungal antioxidation system. These compounds could then function as chemosensitizing agents in concert with conventional drugs or fungicides to improve antifungal efficacy. Methods Benzaldehydes were tested as natural antifungal agents against strains of Aspergillus fumigatus, A. flavus, A. terreus and Penicillium expansum, fungi that are causative agents of human invasive aspergillosis and/or are mycotoxigenic. The yeast Saccharomyces cerevisiae was also used as a model system for identifying gene targets of benzaldehydes. The efficacy of screened compounds as effective chemosensitizers or as antifungal agents in formulations was tested with methods outlined by the Clinical Laboratory Standards Institute (CLSI. Results Several benzaldehydes are identified having potent antifungal activity. Structure-activity analysis reveals that antifungal activity increases by the presence of an ortho-hydroxyl group in the aromatic ring. Use of deletion mutants in the oxidative stress-response pathway of S. cerevisiae (sod1Δ, sod2Δ, glr1Δ and two mitogen-activated protein kinase (MAPK mutants of A. fumigatus (sakAΔ, mpkCΔ, indicates antifungal activity of the benzaldehydes is through disruption of cellular antioxidation. Certain benzaldehydes, in combination with phenylpyrroles, overcome tolerance of A. fumigatus MAPK mutants to this agent and/or increase sensitivity of fungal pathogens to mitochondrial respiration inhibitory agents. Synergistic chemosensitization greatly lowers minimum inhibitory (MIC or fungicidal (MFC

  10. Serotonin Mediates a Learned Increase in Attraction to High Concentrations of Benzaldehyde in Aged "C. elegans"

    Science.gov (United States)

    Tsui, David; van der Kooy, Derek

    2008-01-01

    We utilized olfactory-mediated chemotaxis in "Caenorhabditis elegans" to examine the effect of aging on information processing and animal behavior. Wild-type (N2) young adults (day 4) initially approach and eventually avoid a point source of benzaldehyde. Aged adult animals (day 7) showed a stronger initial approach and a delayed avoidance to…

  11. A theoretical study of benzaldehyde derivatives as tyrosinase inhibitors using Ab initio calculated NQCC parameters

    Science.gov (United States)

    Rafiee, Marjan; Javaheri, Masoumeh

    2015-01-01

    Tyrosinase is a multifunctional copper-containing enzyme. It can catalyze two distinct reactions of melanin synthesis and benzaldehyde derivatives, which are potential tyrosinase inhibitors. To find the relationships between charge distributions of benzaldehyde and their pharmaceutical behavior, the present study aimed at investigating nuclear quadrupole coupling constants of quadrupolare nuclei in the functional benzaldehyde group and calculating some its derivatives. In addition, the differences between the electronic structures of various derivatives of this depigmenting drug were examined. All ab initio calculations were carried out using Gaussian 03. The results predicted benzaldehyde derivatives to be bicentral inhibitors; nevertheless, the oxygen or hydrogen contents of the aldehyde group were not found to be the only active sites. Furthermore with the presence of the aldehyde group, the terminal methoxy group in C4 was found to contribute to tyrosinase inhibitory activities. In addition, an oxygen atom with high charge density in the side chain was found to play an important role in its inhibitory effect. PMID:27844007

  12. A theoretical study of benzaldehyde derivatives as tyrosinase inhibitors using Ab initio calculated NQCC parameters

    Directory of Open Access Journals (Sweden)

    Marjan Rafiee

    2015-09-01

    Full Text Available Tyrosinase is a multifunctional copper-containing enzyme. It can catalyze two distinct reactions of melanin synthesis and benzaldehyde derivatives, which are potential tyrosinase inhibitors. To find the relationships between charge distributions of benzaldehyde and their pharmaceutical behavior, the present study aimed at investigating nuclear quadrupole coupling constants of quadrupolare nuclei in the functional benzaldehyde group and calculating some its derivatives. In addition, the differences between the electronic structures of various derivatives of this depigmenting drug were examined. All ab initio calculations were carried out using Gaussian 03. The results predicted benzaldehyde derivatives to be bicentral inhibitors; nevertheless, the oxygen or hydrogen contents of the aldehyde group were not found to be the only active sites. Furthermore with the presence of the aldehyde group, the terminal methoxy group in C4 was found to contribute to tyrosinase inhibitory activities. In addition, an oxygen atom with high charge density in the side chain was found to play an important role in its inhibitory effect.

  13. Deoxygenation of benzoic acid on metal oxides. I. The selective pathway to benzaldehyde

    NARCIS (Netherlands)

    Lange, de M.W.; Ommen, van J.G.; Lefferts, L.

    2001-01-01

    The mechanism of the selective deoxygenation of benzoic acid to benzaldehyde was studied on ZnO and ZrO2. The results show conclusively that the reaction proceeds as a reverse type of Mars and van Krevelen mechanism consisting of two steps: hydrogen activates the oxide by reduction resulting in the

  14. Catalytic Enantioselective Alkylation of Benzaldehyde with Diethylzinc Using Chiral Nonracemic (Thio)-phosphoramidates

    NARCIS (Netherlands)

    Hulst, Ron; Heres, Hero; Fitzpatrick, Kevin; Peper, Nathalie C.M.W.; Kellogg, Richard M.

    1996-01-01

    Two chiral nonracemic γ-amino alcohols, ephedrine thiol and the corresponding (thio)-phosphoramidates have been examined as catalysts for the enantioselective alkylation of benzaldehyde by diethylzinc. Addition of titanium tetraisopropoxide increases the yield as well as the enantioselectivity; 1-ph

  15. Antifungal activity of redox-active benzaldehydes that target cellular antioxidation

    Science.gov (United States)

    Many pathogenic fungi are becoming resistant to currently available drugs. Disruption of cellular antioxidation systems should be an effective method for control of fungal pathogens. Such disruption can be achieved with redox-active compounds. The aim of this study was to identify benzaldehydes that...

  16. Chemo-sensitization of fungal pathogens to antimicrobial agents using benzaldehyde analogs

    Science.gov (United States)

    Activity of conventional antifungal agents, fludioxonil, strobilurin and antimycinA, which target the oxidative and osmotic stress response systems, was elevated by co-application of certain analogs of benzaldehyde. Fungal tolerance to 2,3-dihydroxybenzaldehyde or 2,3-dihydroxybenzoic acid was foun...

  17. FT-IR spectroscopy and DFT calculation study on the solvent effects of benzaldehyde in organic solvents.

    Science.gov (United States)

    Li, Yi; Zhang, Hui; Liu, Qing

    2012-02-01

    FT-IR spectra of benzaldehyde in 11 different organic solvents were recorded and analyzed. The density functional theory (DFT) B3LYP/6-31G* method was chosen to calculate the infrared spectrum of benzaldehyde in gaseous state. The electrostatic effects of different solvents in benzaldehyde solutions were calculated using DFT with the self-consistent isodensity polarizable continuum model (SCI-PCM). Two remarkable carbonyl (C=O) peaks of benzaldehyde were observed by FT-IR in alcohol solvents, which were caused by different hydrogen bond species and explained by ab initio calculation. The results showed that the combination of SCI-PCM model and ab initio calculation could give excellent agreements with FT-IR spectra of title compound in solutions.

  18. Lignin-derived oxygenate reforming on a bimetallic surface: The reaction of benzaldehyde on Zn/Pt(111)

    Science.gov (United States)

    Shi, Daming; Vohs, John M.

    2016-08-01

    Temperature programmed desorption (TPD) and high-resolution electron energy loss spectroscopy (HREELS) were used to characterize the adsorption and reaction of benzaldehyde (C6H5CHO) on hydrogen-covered Pt(111) and Zn-modified Pt(111) surfaces. Benzaldehyde was found to interact with Pt(111) via both the phenyl ring and carbonyl of the aldehyde group. This bonding configuration facilitates unselective decomposition of the benzaldehyde to produce CO, H2, and small hydrocarbon fragments at relatively low temperatures. On the other hand, benzaldehyde was found to bond to Zn-decorated Pt(111) surface exclusively via the carbonyl group in an η2(C, O) configuration, with the phenyl ring tilted away from the surface. This configuration weakens Csbnd O bond in the carbonyl facilitating its cleavage and helps prevent hydrogenation of the phenyl ring.

  19. Feasibility of gas/solid carboligation: conversion of benzaldehyde to benzoin using thiamine diphosphate-dependent enzymes.

    Science.gov (United States)

    Mikolajek, R; Spiess, A C; Büchs, J

    2007-05-10

    A carboligation was investigated for the first time as an enzymatic gas phase reaction, where benzaldehyde was converted to benzoin using thiamine diphosphate (ThDP)-dependent enzymes, namely benzaldehyde lyase (BAL) and benzoylformate decarboxylase (BFD). The biocatalyst was immobilized per deposition on non-porous support. Some limitations of the gas/solid biocatalysis are discussed based on this carboligation and it is also demonstrated that the solid/gas system is an interesting tool for more volatile products.

  20. Oxidation of benzyl alcohol by K2FeO4 to benzaldehyde over zeolites

    Science.gov (United States)

    Wang, Yuan-Yuan; Song, Hua; Song, Hua-Lin; Jin, Zai-Shun

    2016-10-01

    A novel and green procedure for benzaldehyde synthesis by potassium ferrate oxidation of benzyl alcohol employing zeolite catalysts was studied. The prepared oxidant was characterized by SEM and XRD. The catalytic activity of various solid catalysts was studied using benzyl alcohol as a model compound. USY was found to be a very efficient catalyst for this particular oxidation process. Benzaldehyde yields up to 96.0% could be obtained at the following optimal conditions: 0.2 mL of benzyl alcohol, 4 mmol of K2FeO4, 0.5 g of USY zeolite; 20 mL of cyclohexene, 0.3 mL of acetic acid (36 wt %), 30°C temperature, 4 h reaction time.

  1. Kinetics of the Benzaldehyde-Inhibited Oxidation of Sulfite by Chlorine Dioxide.

    Science.gov (United States)

    Pan, Changwei; Gao, Qingyu; Stanbury, David M

    2016-01-04

    There has been steady interest in the aqueous reaction of ClO2• with sulfur(IV) since the 1950s, and a wide variety of rate laws and mechanisms have been proposed. In neutral-to-alkaline media, the reaction is challenging to study because of its great rate. Here it is shown that benzaldehyde can be used as an additive to slow the reaction and make its rates more amenable to study. The rates can be quantitatively modeled by a mechanism that includes reversible binding of sulfur(IV) by benzaldehyde and a rate-limiting mixed second-order reaction of ClO2• with SO3(2-). The latter reaction occurs through parallel electron transfer from SO3(2-) to ClO2• and oxygen-atom transfer from ClO2• to SO3(2-).

  2. Selectivity modulation in the consecutive hydrogenation of benzaldehyde via functionalization of carbon nanotubes

    Institute of Scientific and Technical Information of China (English)

    Yonghua Zhou; Jing Liu; Xingyun Li; Xiulian Pan; Xinhe Bao

    2012-01-01

    Hydrogenation of benzaldehyde is a typical consecutive reaction,since the intermediate benzyl alcohol is apt to be further hydrogenated.Here we demonstrate that the selectivity of benzyl alcohol can be tuned via functionalization of carbon nanotubes (CNTs),which are used as the support of Pd.With the original CNTs,the selectivity of benzyl alcohol is 88% at a 100% conversion of benzaldehyde.With introduction of oxygen-containing groups onto CNTs,it drops to 27%.In contrast,doping CNTs with N atoms,the selectivity reaches 96% under the same reaction conditions.The kinetic study shows that hydrogenation of benzyl alcohol is significantly suppressed,which can be attributed to weakened adsorption of benzyl alcohol.This is most likely related to the modified electronic structure of Pd species via interaction with functionalized CNTs,as shown by XPS characterization.

  3. Proton transfer reactions between nitric acid and acetone, hydroxyacetone, acetaldehyde and benzaldehyde in the solid phase.

    Science.gov (United States)

    Lasne, Jérôme; Laffon, Carine; Parent, Philippe

    2012-12-01

    The heterogeneous and homogeneous reactions of acetone, hydroxyacetone, acetaldehyde and benzaldehyde with solid nitric acid (HNO(3)) films have been studied with Reflection-Absorption Infrared Spectroscopy (RAIRS) under Ultra-High Vacuum (UHV) conditions in the 90-170 K temperature range. In the bulk or at the surface of the films, nitric acid transfers its proton to the carbonyl function of the organic molecules, producing protonated acetone-H(+), hydroxyacetone-H(+), acetaldehyde-H(+) and benzaldehyde-H(+), and nitrate anions NO(3)(-), a reaction not observed when nitric acid is previously hydrated [J. Lasne, C. Laffon and Ph. Parent, Phys. Chem. Chem. Phys., 2012, 14, 697]. This provides a molecular-scale description of the carbonyl protonation reaction in an acid medium, the first step of the acid-catalyzed condensation of carbonyl compounds, fuelling the growth of secondary organic aerosols (SOA) in the atmosphere.

  4. Model studies on the oxygen-induced formation of benzaldehyde from phenylacetaldehyde using pyrolysis GC-MS and FTIR.

    Science.gov (United States)

    Chu, Fong Lam; Yaylayan, Varoujan A

    2008-11-26

    Benzaldehyde, a potent aroma chemical of bitter almond, can also be formed thermally from phenylalanine and may contribute to the formation of off-aroma. To identify the precursors involved in its generation during Maillard reaction, various model systems containing phenylalanine, phenylpyruvic acid, phenethylamine, or phenylacetaldehyde were studied in the presence and absence of moisture using oxidative and nonoxidative Py-GC-MS. Analysis of the data indicated that phenylacetaldehyde, the Strecker aldehyde of phenylalanine, is the most effective precursor and that both air and water significantly enhanced the rate of benzaldehyde formation from phenylacetaldehyde. Phenylpyruvic acid was the most efficient precursor under nonoxidative conditions. Phenethylamine, on the other hand, needed the presence of a carbonyl compound to generate benzaldehyde only under oxidative conditions. On the basis of the results obtained, a free radical initiated oxidative cleavage of the carbon-carbon double bond of the enolized phenylacetaldehyde was proposed as a possible major mechanism for benzaldehyde formation, and supporting evidence was provided through monitoring of the evolution of the benzaldehyde band from heated phenylacetaldehyde in the presence and absence of 1,1'-azobis(cyclohexanecarbonitrile) on the ATR crystal of an FTIR spectrophotometer. In the presence of the free radical initiator, the enol band of the phenylacetaldehyde centered at 1684 cm(-1) formed and increased over time, and after 18 min of heating time the benzaldehyde band centered at 1697 cm(-1) formed and increased at the expense of the enol band of phenylacetaldehyde, indicating a precursor product relationship.

  5. Cu and Boron Doped Carbon Nitride for Highly Selective Oxidation of Toluene to Benzaldehyde.

    Science.gov (United States)

    Han, Hongling; Ding, Guodong; Wu, Tianbin; Yang, Dexin; Jiang, Tao; Han, Buxing

    2015-07-13

    A novel Cu and boron doped graphitic carbon nitride catalyst (Cu-CNB) was synthesized using cheap precursors and systematically characterized. The selective oxidation of toluene proceeded very smoothly over the catalyst at 70 °C using tert-butyl hydroperoxide (TBHP) as the oxidant to exclusively afford benzaldehyde. The catalyst can be used for at least five cycles without decrease in activity and selectivity.

  6. Enhanced benzaldehyde tolerance in Zymomonas mobilis biofilms and the potential of biofilm applications in fine-chemical production.

    Science.gov (United States)

    Li, Xuan Zhong; Webb, Jeremy S; Kjelleberg, Staffan; Rosche, Bettina

    2006-02-01

    Biotransformation plays an increasingly important role in the industrial production of fine chemicals due to its high product specificity and low energy requirement. One challenge in biotransformation is the toxicity of substrates and/or products to biocatalytic microorganisms and enzymes. Biofilms are known for their enhanced tolerance of hostile environments compared to planktonic free-living cells. Zymomonas mobilis was used in this study as a model organism to examine the potential of surface-associated biofilms for biotransformation of chemicals into value-added products. Z. mobilis formed a biofilm with a complex three-dimensional architecture comprised of microcolonies with an average thickness of 20 microm, interspersed with water channels. Microscopic analysis and metabolic activity studies revealed that Z. mobilis biofilm cells were more tolerant to the toxic substrate benzaldehyde than planktonic cells were. When exposed to 50 mM benzaldehyde for 1 h, biofilm cells exhibited an average of 45% residual metabolic activity, while planktonic cells were completely inactivated. Three hours of exposure to 30 mM benzaldehyde resulted in sixfold-higher residual metabolic activity in biofilm cells than in planktonic cells. Cells inactivated by benzaldehyde were evenly distributed throughout the biofilm, indicating that the resistance mechanism was different from mass transfer limitation. We also found that enhanced tolerance to benzaldehyde was not due to the conversion of benzaldehyde into less toxic compounds. In the presence of glucose, Z. mobilis biofilms in continuous cultures transformed 10 mM benzaldehyde into benzyl alcohol at a steady rate of 8.11 g (g dry weight)(-1) day(-1) with a 90% molar yield over a 45-h production period.

  7. Biotransformation of Benzaldehyde to L-Phenylacetylcarbinol (L-PAC by Free Cells of Torulaspora delbrueckii in presence of Beta-Cyclodextrin

    Directory of Open Access Journals (Sweden)

    Vilas. B. Shukla

    2002-09-01

    Full Text Available Studies were carried out to explore the possibility of decreasing the toxic and inhibitory effects of the substrate benzaldehyde during its biotransformation to L-PAC by free cells of Torulaspora delbrueckii using beta -cyclodextrin (beta -CD. Use of various levels of benzaldehyde and acetaldehyde in presence of 2% of beta -CD showed that, in presence of beta -CD, the organism could tolerate higher levels of benzaldehyde and acetaldehyde. Semi-continuous feeding of benzaldehyde and acetaldehyde was found to increase the yield of L-PAC in comparison with one time feeding.

  8. Probing the active center of benzaldehyde lyase with substitutions and the pseudosubstrate analogue benzoylphosphonic acid methyl ester.

    Science.gov (United States)

    Brandt, Gabriel S; Nemeria, Natalia; Chakraborty, Sumit; McLeish, Michael J; Yep, Alejandra; Kenyon, George L; Petsko, Gregory A; Jordan, Frank; Ringe, Dagmar

    2008-07-22

    Benzaldehyde lyase (BAL) catalyzes the reversible cleavage of ( R)-benzoin to benzaldehyde utilizing thiamin diphosphate and Mg (2+) as cofactors. The enzyme is important for the chemoenzymatic synthesis of a wide range of compounds via its carboligation reaction mechanism. In addition to its principal functions, BAL can slowly decarboxylate aromatic amino acids such as benzoylformic acid. It is also intriguing mechanistically due to the paucity of acid-base residues at the active center that can participate in proton transfer steps thought to be necessary for these types of reactions. Here methyl benzoylphosphonate, an excellent electrostatic analogue of benzoylformic acid, is used to probe the mechanism of benzaldehyde lyase. The structure of benzaldehyde lyase in its covalent complex with methyl benzoylphosphonate was determined to 2.49 A (Protein Data Bank entry 3D7K ) and represents the first structure of this enzyme with a compound bound in the active site. No large structural reorganization was detected compared to the complex of the enzyme with thiamin diphosphate. The configuration of the predecarboxylation thiamin-bound intermediate was clarified by the structure. Both spectroscopic and X-ray structural studies are consistent with inhibition resulting from the binding of MBP to the thiamin diphosphate in the active centers. We also delineated the role of His29 (the sole potential acid-base catalyst in the active site other than the highly conserved Glu50) and Trp163 in cofactor activation and catalysis by benzaldehyde lyase.

  9. Synthesis of Aminophosphine Ligands with Binaphthyl Backbones for Silver(I)-catalyzed Enantioselective Allylation of Benzaldehyde

    Institute of Scientific and Technical Information of China (English)

    WANG,Yi(王以); JI,Bao-Ming(吉保明); DING,Kui-Ling(丁奎岭)

    2002-01-01

    A series of aminophosphine ligands was synthesized from 2amino-2′-hydroxy-1,1′-binaphthyl (NOBIN). Their asymmetric induction efficiency was examined for silver(I)catalyzed enantioselective allylation reaction of benzaldehyde with allyltributyltin.Under the optimized reaction conditions,quantitative yield as well as moderate ee value (54.5% ee)of product was achieved by the catalysis with silver(I)/3 complex. The effects of the binaphthyl backbone and the substituted situated at chelating N, Patoms on enantioselectivity of the reaction were also discussed.

  10. A Novel Acetate Selective UV-Vis Chemosensor Containing a Tripodal Benzaldehydic-phenylhydrazone

    Institute of Scientific and Technical Information of China (English)

    QIAO Yan-Hong; LIN Hai; SHAO Jie; LIN Hua-Kuan

    2008-01-01

    A new colorimetric chemosensor 1 based on a tripodal benzaldehydic-phenylhydrazone selectively sensing acetate ion has been synthesized. The highly selective binding ability of receptor I to acetate ion over other studied anions was demonstrated by UV-Vis absorption spectroscopy in DMSO. Compared with other anions studied, its sorption spectrum change has occurred when receptor 1 was treated with other different guest anions (F-, Cl-, Br-,I-, H2PO4- and OH-). The Kass of receptor 1 binding with acetate ion is 1.69×104.

  11. Engineering NiO sensitive materials and its ultra-selective detection of benzaldehyde.

    Science.gov (United States)

    Yang, Fuchao; Guo, Zhiguang

    2016-04-01

    Ongoing interest in oxide semiconductor as components of gas sensing devices is motivated by environmental monitoring and intelligent control. NiO with different precursor solution were synthesized by aqueous chemical deposition and pyrolysis process. Here the method is quite facile, green and free of surfactant. Their morphology, crystal structure and chemical composition have been systemically characterized by various techniques. Interestingly, the microstructures of NiO can be engineered by different nickel salt (nitrate or chloride). These NiO based gas sensors showed substantially enhanced responses to benzaldehyde target analyte and exhibited fast response-recover feature. The observed gas sensing behavior is explained in terms of oxygen ionosorption mechanism.

  12. Crystal structure of 4-(4-meth-oxy-phen-oxy)benzaldehyde.

    Science.gov (United States)

    Schäfer, Andreas; Iovkova-Berends, Ljuba; Gilke, Stefan; Kossmann, Paul; Preut, Hans; Hiersemann, Martin

    2015-12-01

    The title compound, C14H12O3, was synthesized via the nucleophilic addition of 4-meth-oxy-phenol to 4-fluoro-benzaldehyde. The dihedral angle between the least-squares planes of the benzene rings is 71.52 (3)° and the C-O-C angle at the central O atom is 118.82 (8)°. In the crystal, weak C-H⋯O hydrogen bonds link the molecules to generate supra-molecular layers in the bc plane. The layers are linked by weak C-H⋯π inter-actions.

  13. Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(αMe)Phe as catalyst

    NARCIS (Netherlands)

    Hulst, Ron; Broxterman, Quirinus B.; Kamphuis, Johan; Formaggio, Fernando; Crisma, Marco; Toniolo, Claudio; Kellogg, Richard M.

    1997-01-01

    Two cyclo-dipeptides based on His and the unnatural (αMe)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented.

  14. Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(alpha-Me)Phe as catalyst

    NARCIS (Netherlands)

    Hulst, R; Broxterman, QB; Kamphuis, J; Formaggio, F; Crisma, M; Toniolo, C; Kellogg, RM

    1997-01-01

    Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C)

  15. The effect of solvent on the kinetics of the oxidation of benzaldehydes by quinolinium chlorochromate in aqueous organic solvent media

    Directory of Open Access Journals (Sweden)

    G. FATIMA JEYANTHI

    2002-12-01

    Full Text Available The kinetics of the oxidation of benzaldehyde and para-substituted benzaldehydes by quinolinium chlorochromate in water-dimethylformamide mixtures has been studied under pseudo-first-order conditions at 25±0.2°C. The operation of non-specific and specific solvent-solute interactions was explored by correlating the rate data with solvent parameters through a correlation analysis technique. Both electron-releasing and electron-withdrawing substitutents enhance the rate of oxidation and the Hammett plot shows a break in the reactivity order indicating the applicability of a dual mechanism.

  16. Synthesis, spectral and computational analysis of 2-(N-bromoalkoxy)-5-(phenylazo)benzaldehydes and their oximes

    Science.gov (United States)

    Balachander, R.; Manimekalai, A.

    2017-04-01

    2-(N-Bromoalkoxy)-5-(phenylazo)benzaldehydes 1-3, 2-(3-bromomethylbenzyloxy)-5-(phenylazo)benzaldehyde 4 and their oximes 5-8 were synthesized and characterized by FT-IR, GC-MS, 1H, 13C and 2D NMR spectroscopy. The favoured conformations of aldehydes 1-4 and oximes 5-8 were predicted theoretically by geometry optimization and potential energy scan (PES) studies. Selected geometrical parameters and molecular properties such as AIM, NBO, HOMO-LUMO and MEP surfaces were derived from optimized structures. IR, 1H and 13C NMR data were also computed using Gaussian-03 package and compared with the observed values.

  17. Enhancement of reaction rates for catalytic benzaldehyde hydrogenation and sorbitol dehydration in water solvent by addition of carbon dioxide

    Indian Academy of Sciences (India)

    Masayuki Shirai; Osamu Sato; Norihito Hiyoshi; Aritomo Yamaguchi

    2014-03-01

    The effect of pressured carbon dioxide on heterogeneous hydrogenation of benzaldehyde and homogeneous dehydration of sorbitol in water solvent was studied. Initial hydrogenation rates of benzaldehyde over a charcoal-supported palladium catalyst in water at 313 K were enhanced by the addition of carbon dioxide. The initial rate increased with an increase in carbon dioxide pressure and became a maximum at 5 MPa. Dehydration of sorbitol proceeded in water phase at 500 K and initial dehydration rates were enhanced by addition of 30 MPa of carbon dioxide.

  18. Stereocontrol of the Schiff Base of Substituted Benzaldehyde to Staudinger Cycloaddition Reaction

    Institute of Scientific and Technical Information of China (English)

    齐传民; 杨凌春; 孙彭利

    2003-01-01

    Syntheses of 4 novel chiral azetidin-2-one derivatives,which were characterized by 1H NMR,IR,specific rotation and elemental analysis,through Staudinger cycloaddition reaction of Schiff base of benzaldehyde with chlorine substitution at different position in benzene ring,were described.For the first time,this type of 3S,4R configuration azetidin-2-one monocrystals with many chiral centers [(3S,4R)-3-hydroxy-N-[(S)-(1-phenyl)ethyl]-4-(2''-chlorophenyl)-azetidin-2-one monocrystal]were obtained,the structures of which were determined by X-ray diffraction analysis.The effects of Schiff base of benzaldehyde with chlorine substitution at different position in benzene ring on stereoselectivity of Staudinger cycloaddition reaction products were discussed and the results are showed as below:2-chlorophenyl Schiff base favored to yield 3S,4R configuration product,but 4-chlorophenyl Schiff base favored to yield 3R,4S configuration product.The reaction orientation of 2,4-dichlorophenyl Schiff base was determined by corporate effect of 2- and 4-chlorine,and that of the 4-chlorine was more obvious.In contrast to 4-chlorophenyl,although the main product was 3R,4S configuration,3-chlorophenyl owned lower selectivity.

  19. Effect of benzaldehyde on the electrodeposition and corrosion properties of Ni–W alloys

    Institute of Scientific and Technical Information of China (English)

    U. Pramod Kumar; C. Joseph Kennady

    2015-01-01

    The effect of different concentrations of benzaldehyde on the electrodeposition of Ni–W alloy coatings on a mild steel substrate from a citrate electrolyte was investigated in this study. The electrolytic alkaline bath (pH 8.0) contained stoichiometric amounts of nickel sulfate, sodium tungstate, and trisodium citrate as precursors. The corrosion resistance of the Ni–W-alloy-coated specimens in 0.2 mol/L H2SO4 was studied using various electrochemical techniques. Tafel polarization studies reveal that the alloy coatings obtained from the bath containing 50 ppm benzaldehyde exhibit a protection efficiency of 95.33%. The corrosion rate also decreases by 21.5 times compared with that of the blank. A higher charge-transfer resistance of 1159.40?·cm2 and a lower double-layer capacitance of 29.4 μF·cm?2 further confirm the better corrosion resistance of the alloy coating. X-ray diffraction studies reveal that the deposits on the mild steel surface are consisted of nanocrystals. A lower surface roughness value (Rmax) of the deposits is confirmed by atomic force microscopy.

  20. Effect of benzaldehyde on the electrodeposition and corrosion properties of Ni-W alloys

    Science.gov (United States)

    Pramod Kumar, U.; Kennady, C. Joseph

    2015-10-01

    The effect of different concentrations of benzaldehyde on the electrodeposition of Ni-W alloy coatings on a mild steel substrate from a citrate electrolyte was investigated in this study. The electrolytic alkaline bath (pH 8.0) contained stoichiometric amounts of nickel sulfate, sodium tungstate, and trisodium citrate as precursors. The corrosion resistance of the Ni-W-alloy-coated specimens in 0.2 mol/L H2SO4 was studied using various electrochemical techniques. Tafel polarization studies reveal that the alloy coatings obtained from the bath containing 50 ppm benzaldehyde exhibit a protection efficiency of 95.33%. The corrosion rate also decreases by 21.5 times compared with that of the blank. A higher charge-transfer resistance of 1159.40 Ω·cm2 and a lower double-layer capacitance of 29.4 μF·cm-2 further confirm the better corrosion resistance of the alloy coating. X-ray diffraction studies reveal that the deposits on the mild steel surface are consisted of nanocrystals. A lower surface roughness value ( R max) of the deposits is confirmed by atomic force microscopy.

  1. Coupled electron and proton transfer processes in 4-dimethylamino-2-hydroxy-benzaldehyde.

    Science.gov (United States)

    Zgierski, Marek Z; Fujiwara, Takashige; Lim, Edward C

    2011-09-08

    TDDFT calculations, picosecond transient absorption, and time-resolved fluorescence studies of 4-dimethylamino-2-hydroxy-benzaldehyde (DMAHBA) have been carried out to study the electron and proton transfer processes in polar (acetonitrile) and nonpolar (n-hexane) solvents. In n-hexane, the transient absorption (TA) as well as the fluorescence originate from the ππ* state of the keto form (with the carbonyl group in the benzaldehyde ring), which is produced by an intramolecular proton transfer from the initially excited ππ* state of the enol form (OH group in the ring). The decay rate of TA and fluorescence are essentially identical in n-hexane. In acetonitrile, on the other hand, the TA exhibits features that can be assigned to the highly polar twisted intramolecular charge transfer (TICT) states of enol forms, as evidenced by the similarity of the absorption to the TICT-state absorption spectra of the closely related 4-dimethylaminobenzaldehyde (DMABA). As expected, the decay rate of the TICT-state of DMAHBA is different from the fluorescence lifetime of the ππ* state of the keto form. The occurrence of the proton and electron transfers in acetonitrile is in good agreement with the predictions of the TDDFT calculations. The very short-lived (∼1 ps) fluorescence from the ππ* state of the enol form has been observed at about 380 nm in n-hexane and at about 400 nm in acetonitrile.

  2. Purification and characterization of benzyl alcohol- and benzaldehyde- dehydrogenase from Pseudomonas putida CSV86.

    Science.gov (United States)

    Shrivastava, Rahul; Basu, Aditya; Phale, Prashant S

    2011-08-01

    Pseudomonas putida CSV86 utilizes benzyl alcohol via catechol and methylnaphthalenes through detoxification pathway via hydroxymethylnaphthalenes and naphthaldehydes. Based on metabolic studies, benzyl alcohol dehydrogenase (BADH) and benzaldehyde dehydrogenase (BZDH) were hypothesized to be involved in the detoxification pathway. BADH and BZDH were purified to apparent homogeneity and were (1) homodimers with subunit molecular mass of 38 and 57 kDa, respectively, (2) NAD(+) dependent, (3) broad substrate specific accepting mono- and di-aromatic alcohols and aldehydes but not aliphatic compounds, and (4) BADH contained iron and magnesium, while BZDH contained magnesium. BADH in the forward reaction converted alcohol to aldehyde and required NAD(+), while in the reverse reaction it reduced aldehyde to alcohol in NADH-dependent manner. BZDH showed low K (m) value for benzaldehyde as compared to BADH reverse reaction. Chemical cross-linking studies revealed that BADH and BZDH do not form multi-enzyme complex. Thus, the conversion of aromatic alcohol to acid is due to low K (m) and high catalytic efficiency of BZDH. Phylogenetic analysis revealed that BADH is a novel enzyme and diverged during the evolution to gain the ability to utilize mono- and di-aromatic compounds. The wide substrate specificity of these enzymes enables strain to detoxify methylnaphthalenes to naphthoic acids efficiently.

  3. Electropolymerized fluorinated aniline-based fiber for headspace solid-phase microextraction and gas chromatographic determination of benzaldehyde in injectable pharmaceutical formulations.

    Science.gov (United States)

    Mohammadi, Ali; Mohammadi, Somayeh; Bayandori Moghaddam, Abdolmajid; Masoumi, Vahideh; Walker, Roderick B

    2014-10-01

    In this study, a simple method was developed and validated to detect trace levels of benzaldehyde in injectable pharmaceutical formulations by solid-phase microextraction coupled with gas chromatography-flame ionization detector. Polyaniline was electrodeposited on a platinum wire in trifluoroacetic acid solvent by cyclic voltammetry technique. This fiber shows high thermal and mechanical stability and high performance in extraction of benzaldehyde. Extraction and desorption time and temperature, salt effect and gas chromatography parameters were optimized as key parameters. At the optimum conditions, the fiber shows good linearity between peak area ratio of benzaldehyde/3-chlorobenzaldehyde and benzaldehyde concentration in the range of 50-800 ng/mL with percent relative standard deviation values ranging from 0.75 to 8.64% (n = 3). The limits of quantitation and detection were 50 and 16 ng/mL, respectively. The method has the requisite selectivity, sensitivity, accuracy and precision to assay benzaldehyde in injectable pharmaceutical dosage forms.

  4. Benzaldehyde thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Xiu-Ping Ju

    2008-12-01

    Full Text Available The title compound, C8H9N3S, contains two molecules in the asymmetric unit. One molecule is close to being planar (r.m.s. deviation from the mean plane = 0.06 Å for the non-H atoms, while the other exhibits a dihedral angle of 21.7 (1° between the benzene ring and the mean plane of the thiosemicarbazone unit. Intermolecular N—H...S hydrogen bonds link the molecules into layers parallel to the (010 plane.

  5. Production of the flavor compound benzaldehyde by lactic acid bacteria: role of manganese and its transport systems in Lactobacillus plantarum

    NARCIS (Netherlands)

    Nierop Groot, M.N.

    2001-01-01

    One of the aims of the research described in this thesis (Chapter 1 and 2) was to investigate the conversion of phenylalanine to the aromatic flavor compound benzaldehyde in lactic acid bacteria (LAB) (Chapter 3). Lactobacillus plantarum was used as the model organism to study phenylalanine degradat

  6. Quantification of brown dog tick repellents, 2-hexanone and benzaldehyde, and release from tick-resistant beagles, Canis lupus familiaris

    Science.gov (United States)

    We have recently shown that repellency of the tick Rhipicephalus sanguineus sensu lato by the tick resistant dog breed Beagle is mediated by volatile organic compounds 2-hexanone and benzaldehyde present in Beagle dog odour. Ectoparasite location on animal hosts is affected by variation in odour com...

  7. Preparation and characterization of new and improved soluble-starches, -amylose, and -amylopectin by reaction with benzaldehyde/zinc chloride.

    Science.gov (United States)

    Johnston, David A; Mukerjea, Rupendra; Robyt, John F

    2011-12-13

    Seven different starches from potato, rice, maize, waxymaize, amylomaize-VII, shoti, and tapioca, and potato amylose and potato amylopectin have been reacted with benzaldehyde, catalyzed by ZnCl(2), to give new water-soluble starches and water soluble-amylose and soluble-amylopectin. In contrast to the native starches, aqueous solutions of the modified starches could not be precipitated with 2-, 3-, or 4-volumes of ethanol. β-Amylase gave no reaction with the modified starches, in contrast to the native starches, indicating that the modification occurred exclusively at the nonreducing-ends, giving 4,6-benzylidene-D-glucopyranose at the nonreducing-ends. Reactions of α-amylase with native and modified potato and rice starches gave a decrease in the triiodide blue color and an increase in the reducing-value that were similar for the native- and modified-starches, indicating the modified starches had not been significantly altered by the modification. The benzaldehyde-modified starches and benzaldehyde-modified potato amylose and potato amylopectin components, therefore, have a starch structure very much like their native counterparts, in contrast to the Lintner, Small, and the alcohol/acid-hydrolyzed soluble-starches that have undergone acid hydrolysis. The benzaldehyde-modified starches and starch components have significantly higher water solubility than their native counterparts even though the structures of the modified starches had only been slightly altered from the structures of their native counterparts. They all gave crystal-clear solutions that did not retrograde.

  8. Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything?

    Science.gov (United States)

    Natsch, Andreas; Gfeller, Hans; Haupt, Tina; Brunner, Gerhard

    2012-10-15

    Skin sensitizers chemically modify skin proteins rendering them immunogenic. Sensitizing chemicals have been divided into applicability domains according to their suspected reaction mechanism. The widely accepted Schiff base applicability domain covers aldehydes and ketones, and detailed structure-activity-modeling for this chemical group was presented. While Schiff base formation is the obvious reaction pathway for these chemicals, the in silico work was followed up by limited experimental work. It remains unclear whether hydrolytically labile Schiff bases can form sufficiently stable epitopes to trigger an immune response in the living organism with an excess of water being present. Here, we performed experimental studies on benzaldehydes of highly differing skin sensitization potential. Schiff base formation toward butylamine was evaluated in acetonitrile, and a detailed SAR study is presented. o-Hydroxybenzaldehydes such as salicylaldehyde and the oakmoss allergens atranol and chloratranol have a high propensity to form Schiff bases. The reactivity is highly reduced in p-hydroxy benzaldehydes such as the nonsensitizing vanillin with an intermediate reactivity for p-alkyl and p-methoxy-benzaldehydes. The work was followed up under more physiological conditions in the peptide reactivity assay with a lysine-containing heptapeptide. Under these conditions, Schiff base formation was only observable for the strong sensitizers atranol and chloratranol and for salicylaldehyde. Trapping experiments with NaBH₃CN showed that Schiff base formation occurred under these conditions also for some less sensitizing aldehydes, but the reaction is not favored in the absence of in situ reduction. Surprisingly, the Schiff bases of some weaker sensitizers apparently may react further to form stable peptide adducts. These were identified as the amides between the lysine residues and the corresponding acids. Adduct formation was paralleled by oxidative deamination of the parent

  9. Heterocyclyl linked anilines and benzaldehydes as precursors for biologically significant new chemical entities

    Indian Academy of Sciences (India)

    Raman K Verma; Vijay Kumar; Prithwish Ghosh; Lalit K Wadhwa

    2012-09-01

    Benzylidene and benzyl thiazolidinediones, oxazolidinediones, isoxazolidinediones and their acyclic analogs like alpha alkylthio/alkoxy phenylpropanoic acids, beta-keto esters and tyrosine-based compounds possess broad therapeutic potential in general and as Peroxisome Proliferator Activated Receptors (PPARs) agonists in particular in the management of hyperglycemia and hyperlipidaemia for the treatment of Type 2 Diabetes (T2D). We have synthesised and characterized some novel and suitably substituted heterocyclyl linked benzaldehydes and anilines, which can be easily and very readily derivatized to all the above mentioned classes to generate new chemical entities of broader biological significance. Synthesis of their benzylidene thiazolidinedione and diethyl malonate and also benzyl diethyl malonate and alpha-bromoesters derivatives is reported in some of the cases in the present work.

  10. Heats of formation and protonation thermochemistry of gaseous benzaldehyde, tropone and quinone methides

    Science.gov (United States)

    Bouchoux, Guy

    2010-08-01

    Quantum chemistry calculations using composite G3B3, G3MP2B3 and CBS-QB3 methods were performed for benzaldehyde, 1, tropone, 2, ortho-quinone methide, 3, para-quinone methide, 4, their protonated forms 1H+- 4H+ and the isomeric meta-hydroxybenzyl cation 5H+. The G3B3 298 K heats of formation values obtained in this work are: -39, 61, 52, 39, 661, 679, 699, 680 and 733 kJ mol -1 for 1- 4, 1H+- 5H+, respectively. At the same level of theory, computed proton affinities are equal to 834, 916, 887 and 892 kJ mol -1 for molecules 1- 4. These results allow to correct discrepancies on the previously reported thermochemistry of molecules 2- 4 and cations 2H+- 5H+.

  11. STUDY ON THE TREATMENT OF 3—PHENOXY—BENZALDEHYDE INDUSTRIAL WASTEWATER WITH POLYMERIC ADSORBENT

    Institute of Scientific and Technical Information of China (English)

    ZhuShiyun; ChenJinlong; 等

    1998-01-01

    In this paper,the two effluents from PBA (3-phenoxy-benzaldehyde) production process were treated by polymeric adsorbent CHA-111.PBA or PBC (3-phenoxy-benzoic acid) was recovered from the wastewater in the process of neutralization.As a secondary treatment method,adsorption with CHA-111 showed better efficiency than photocatolytic decomposition and solvent extraction.The optimal technological parameters were:adsorption:current velocity:2.0BV/hr(bed volume per hour),room temperature;desorption:current velocity:2.0BV/hr(bed volume per hour),room temperature;desorption:current velocity:1.0 BV/hr,80℃,8% sodium hydroxide aqueous solutions.In conclusion,99.9% COD in the neutralizing wastewater and 98.4% COD in the hydrolysis wastewater are removed successfully.

  12. Antitrypanosomal Activity of Novel Benzaldehyde-Thiosemicarbazone Derivatives from Kaurenoic Acid †

    Directory of Open Access Journals (Sweden)

    Cecília M. A. de Oliveira

    2011-01-01

    Full Text Available A series of new thiosemicarbazones derived from natural diterpene kaurenoic acid were synthesized and tested against the epimastigote forms of Trypanosoma cruzi to evaluate their antitrypanosomal potential. Seven of the synthesized thiosemicarbazones were more active than kaurenoic acid with IC50 values between 2-24.0 mM. The o-nitro-benzaldehyde-thiosemicarbazone derivative was the most active compound with IC50 of 2.0 mM. The results show that the structural modifications accomplished enhanced the antitrypanosomal activity of these compounds. Besides, the thiocyanate, thiosemicarbazide and the p- methyl, p-methoxy, p-dimethylamine, m-nitro and o-chlorobenzaldehyde-thiosemicarbazone derivatives displayed lower toxicity for LLMCK2 cells than kaurenoic acid, exhibing an IC50 of 59.5 mM.

  13. Large-scale synthesis of ultrathin tungsten oxide nanowire networks: an efficient catalyst for aerobic oxidation of toluene to benzaldehyde under visible light.

    Science.gov (United States)

    Bai, Hua; Yi, Wencai; Liu, Jingyao; Lv, Qing; Zhang, Qing; Ma, Qiang; Yang, Haifeng; Xi, Guangcheng

    2016-07-14

    As a very important chemical raw material, the selective formation of benzaldehyde from toluene at preparative or industrial levels requires the use of highly corrosive chlorine and high reaction temperatures, which severely corrodes equipment, pollutes the environment, and consumes a lot of energy. Herein, we report a robust and highly active catalyst for the benzaldehyde evolution reaction that is constructed by the surfactant-free growth of oxygen vacancy-rich W18O49 ultrathin nanowire networks. Under atmospheric pressure and visible-light irradiation, the new catalyst can selectively (92% selectivity) catalyze the aerobic oxidation of toluene to benzaldehyde with yields of above 95%.

  14. Polydopamine-Coated TiO2 Nanotubes for Selective Photocatalytic Oxidation of Benzyl Alcohol to Benzaldehyde Under Visible Light.

    Science.gov (United States)

    Tripathy, Jyotsna; Loget, Gabriel; Altomare, Marco; Schmuki, Patrik

    2016-05-01

    TiO2 nanotube arrays grown by anodization were coated with thin layers of polydopamine as visible light sensitizer. The PDA-coated TiO2 scaffolds were used as photocatalyst for selective oxidation of benzyl alcohol under monochromatic irradiation at 473 nm. Benzaldehyde was selectively formed and no by-products could be detected. A maximized reaction yield was obtained in O2-saturated acetonitrile. A mechanism is proposed that implies firstly the charge carrier generation in polydopamine as a consequence of visible light absorption. Secondly, photo-promoted electrons are injected in TiO2 conduction band, and subsequently transferred to dissolved O2 to form O*2- radicals. These radicals react with benzyl alcohol and lead to its selective dehydrogenation oxidation towards benzaldehyde.

  15. Studies on crystal growth and physical properties of 4-(dimethylamino)benzaldehyde-2,4-dinitroaniline single crystal

    Science.gov (United States)

    Jebin, R. P.; Suthan, T.; Rajesh, N. P.; Vinitha, G.; Dhas, S. A. Britto

    2016-07-01

    The organic material 4-(dimethylamino)benzaldehyde-2,4-dinitroaniline has been grown by slow evaporation technique. Single crystal and Powder X-ray diffraction studies have been carried out to conform the grown crystal. FTIR and FT-Raman spectra were recorded to identify the functional groups present in the crystal. The optical property of the grown crystal was analysed by UV-Vis-NIR measurement. The thermal property of the grown crystal was analysed by thermogravimetric (TG) and differential thermal analyses (DTA). Thermal diffusivity of the grown crystal was analysed by Photo acoustic spectroscopic (PAS) studies. The third order nonlinear optical properties of 4-(dimethylamino)benzaldehyde-2,4-dinitroaniline was measured by the Z-scan technique using 532 nm diode pumped continuous wave (CW) Nd:YAG laser. The mechanical property of the grown crystal was analysed by using microhardness studies.

  16. The Production of Benzaldehyde by Rhizopus oligosporus USM R1 in a Solid State Fermentation (SSF System of Soy Bean Meal: Rice Husks

    Directory of Open Access Journals (Sweden)

    Norliza, A. W.

    2005-01-01

    Full Text Available The cultivation of Rhizopus oligosporus USM R1 for the production of benzaldehyde, a bitter cherry almond flavour was performed using soya bean meal and rice husks as the substrates. The identification of R. oligosporus USM R1 was performed based on the observation made under light microscope and scanning electron microscope (SEM. The optimum conditions for the SSF in a 250-ml Erlenmeyer flask system were 40% (v/w water content, substrate particle size of 0.7 mm; inoculum size of 1 x 10^5 spores/g substrate; incubation temperature of 30C; substrate amount of 7 g and the ratio of soy bean meal: rice husks of 50:50%. A maximum benzaldehyde production was obtained when the substrate was agitated after 48 hour for a 96 hour fermentation time. The highest benzaldehyde production obtained after 96 hour cultivation was 5.47 mg g-1 substrate. The supplementation of carbon and nitrogen sources in the substrate mixture revealed an enhancement in the growth and benzyldehyde production. A maximum production of benzaldehyde was obtained with the supplementation of L-phenylalanine, a precursor for benzaldehyde biosynthesis which gave 38.69 mg benzaldehyde/g substrate. This is approximately 6-folds higher compared to the substrates without the supplementation of L-phenylalanine.

  17. Large-scale synthesis of ultrathin tungsten oxide nanowire networks: an efficient catalyst for aerobic oxidation of toluene to benzaldehyde under visible light

    Science.gov (United States)

    Bai, Hua; Yi, Wencai; Liu, Jingyao; Lv, Qing; Zhang, Qing; Ma, Qiang; Yang, Haifeng; Xi, Guangcheng

    2016-07-01

    As a very important chemical raw material, the selective formation of benzaldehyde from toluene at preparative or industrial levels requires the use of highly corrosive chlorine and high reaction temperatures, which severely corrodes equipment, pollutes the environment, and consumes a lot of energy. Herein, we report a robust and highly active catalyst for the benzaldehyde evolution reaction that is constructed by the surfactant-free growth of oxygen vacancy-rich W18O49 ultrathin nanowire networks. Under atmospheric pressure and visible-light irradiation, the new catalyst can selectively (92% selectivity) catalyze the aerobic oxidation of toluene to benzaldehyde with yields of above 95%.As a very important chemical raw material, the selective formation of benzaldehyde from toluene at preparative or industrial levels requires the use of highly corrosive chlorine and high reaction temperatures, which severely corrodes equipment, pollutes the environment, and consumes a lot of energy. Herein, we report a robust and highly active catalyst for the benzaldehyde evolution reaction that is constructed by the surfactant-free growth of oxygen vacancy-rich W18O49 ultrathin nanowire networks. Under atmospheric pressure and visible-light irradiation, the new catalyst can selectively (92% selectivity) catalyze the aerobic oxidation of toluene to benzaldehyde with yields of above 95%. Electronic supplementary information (ESI) available: Experimental procedure, XRD patterns, TEM and HRTEM images, energy-dispersive X-ray spectra, UV-vis spectra, X-ray photoelectron spectroscopy (XPS), and EDS. See DOI: 10.1039/c6nr02949c

  18. Real-Time Detection of Traces of Benzaldehyde in Benzyl Alcohol as a Solvent by a Flexible Lanthanide Microporous Metal-Organic Framework.

    Science.gov (United States)

    Zhang, Huan; Chen, Diming; Ma, Huili; Cheng, Peng

    2015-10-26

    Luminescent 3D lanthanide metal-organic framework (Ln-MOF) {[Tb2 (TATAB)2 ]⋅4 H2 O⋅6 DMF}n (1) was synthesized under solvothermal conditions by using flexible ligand 4,4',4''-s-triazine-1,3,5-triyltri-p-aminobenzoate (TATAB). A phase transition was observed between low temperature and room temperature. The luminescence of 1 could be enhanced by formaldehyde and quenched efficiently by trace amounts of benzaldehyde in solvents such as benzyl alcohol (0.01-2.0 vol %) and ethanol (0.01-2.5 vol %). This is the first use of a Ln-MOF as chemical sensor for both formaldehyde and benzaldehyde. The high sensitivity and selectivity of the luminescence response of 1 to benzaldehyde allows it to be used as an excellent sensor for identifying benzaldehyde and provides a simple and convenient method for detecting traces of benzaldehyde in benzyl alcohol based injections. This work establishes a new strategy for detection of benzaldehyde in benzyl alcohol by luminescent MOFs.

  19. Benzaldehyde is a precursor of phenylpropylamino alkaloids as revealed by targeted metabolic profiling and comparative biochemical analyses in Ephedra spp.

    Science.gov (United States)

    Krizevski, Raz; Bar, Einat; Shalit, O R; Levy, Asaf; Hagel, Jillian M; Kilpatrick, Korey; Marsolais, Frédéric; Facchini, Peter J; Ben-Shabat, Shimon; Sitrit, Yaron; Lewinsohn, Efraim

    2012-09-01

    Ephedrine and pseudoephedrine are phenylpropylamino alkaloids widely used in modern medicine. Some Ephedra species such as E. sinica Stapf (Ephedraceae), a widely used Chinese medicinal plant (Chinese name: Ma Huang), accumulate ephedrine alkaloids as active constituents. Other Ephedra species, such as E. foeminea Forssk. (syn. E. campylopoda C.A. Mey) lack ephedrine alkaloids and their postulated metabolic precursors 1-phenylpropane-1,2-dione and (S)-cathinone. Solid-phase microextraction analysis of freshly picked young E. sinica and E. foeminea stems revealed the presence of increased benzaldehyde levels in E. foeminea, whereas 1-phenylpropane-1,2-dione was detected only in E. sinica. Soluble protein preparations from E. sinica and E. foeminea stems catalyzed the conversion of benzaldehyde and pyruvate to (R)-phenylacetylcarbinol, (S)-phenylacetylcarbinol, (R)-2-hydroxypropiophenone (S)-2-hydroxypropiophenone and 1-phenylpropane-1,2-dione. The activity, termed benzaldehyde carboxyligase (BCL) required the presence of magnesium and thiamine pyrophosphate and was 40 times higher in E. sinica as compared to E. foeminea. The distribution patterns of BCL activity in E. sinica tissues correlates well with the distribution pattern of the ephedrine alkaloids. (S)-Cathinone reductase enzymatic activities generating (1R,2S)-norephedrine and (1S,1R)-norephedrine were significantly higher in E. sinica relative to the levels displayed by E. foeminea. Surprisingly, (1R,2S)-norephedrine N-methyltransferase activity which is a downstream enzyme in ephedrine biosynthesis was significantly higher in E. foeminea than in E. sinica. Our studies further support that benzaldehyde is the metabolic precursor to phenylpropylamino alkaloids in E. sinica.

  20. Inhibitory Kinetics of p-Substituted Benzaldehydes on Polyphenol Oxidase from the Fifth Instar of Pieris Rapae L.

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Polyphenol oxidase (PPO) is the enzyme responsible for enzymatic browning during the growth of insects. It is also involved in defense reactions and is related with immunities in insects. PPO,a metalloenzyme oxidase, catalyzes the oxidation of o-diphenol to o-quinone. The present paper describes the effects of benzaldehyde and its p-substituted derivatives on the activity of PPO from the fifth instar of Pieris rapae L. PPO from the fifth instar of Pieris rapae L. was purified using ammonium sulfate fractionation and chromatography on Sephadex G-100. The enzyme kinetics was characterized using L-3,4-dihydroxyphenylalanine (L-DOPA) as substrate. The results show that benzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, and p-cyanobenzaldehyde can inhibit the PPO activity for the oxidation of L-DOPA. The inhibitor concentration leading to 50% activity lost, IC50, was estimated to be 5.90, 5.62, 2.83, and 2.91 mmol/L for the four tested inhibitors, respectively. Kinetic analyses show that the inhibitory effects of these compounds are reversible. Benzaldehyde, p-hydroxybenzaldehyde, and p-chlorobenzaldehyde are noncompetitive inhibitors while p-cyanobenzaldehyde is a mixed-type inhibitor. The inhibition constants were determined for all four inhibitors.p-chlorobenzaldehyde and p-cyanobenzaldehyde were more potent inhibitors than the other compounds. These results provide a basis for developing PPO inhibition-based pesticides.

  1. Structure of the ThDP-dependent enzyme benzaldehyde lyase refined to 1.65 Å resolution

    Energy Technology Data Exchange (ETDEWEB)

    Maraite, Andy; Schmidt, Thomas; Ansörge-Schumacher, Marion B. [Department of Biotechnology, Faculty of Natural Sciences, RWTH Aachen University, Worringerweg 1, 52074 Aachen (Germany); Brzozowski, A. Marek; Grogan, Gideon, E-mail: grogan@ysbl.york.ac.uk [Structural Biology Laboratory, Department of Chemistry, University of York, Heslington, York YO10 5YW (United Kingdom); Department of Biotechnology, Faculty of Natural Sciences, RWTH Aachen University, Worringerweg 1, 52074 Aachen (Germany)

    2007-07-01

    The X-ray crystal structure of the ThDP-dependent enzyme benzaldehyde lyase has been refined to 1.65 Å. Benzaldehyde lyase (BAL; EC 4.1.2.38) is a thiamine diphosphate (ThDP) dependent enzyme that catalyses the enantioselective carboligation of two molecules of benzaldehyde to form (R)-benzoin. BAL has hence aroused interest for its potential in the industrial synthesis of optically active benzoins and derivatives. The structure of BAL was previously solved to a resolution of 2.6 Å using MAD experiments on a selenomethionine derivative [Mosbacher et al. (2005 ▶), FEBS J.272, 6067–6076]. In this communication of parallel studies, BAL was crystallized in an alternative space group (P2{sub 1}2{sub 1}2{sub 1}) and its structure refined to a resolution of 1.65 Å, allowing detailed observation of the water structure, active-site interactions with ThDP and also the electron density for the co-solvent 2-methyl-2,4-pentanediol (MPD) at hydrophobic patches of the enzyme surface.

  2. Quantification of brown dog tick repellents, 2-hexanone and benzaldehyde, and release from tick-resistant beagles, Canis lupus familiaris.

    Science.gov (United States)

    de Oliveira Filho, Jaires Gomes; Sarria, André Lucio Franceschini; Ferreira, Lorena Lopes; Caulfield, John C; Powers, Stephen J; Pickett, John A; de León, Adalberto A Pérez; Birkett, Michael A; Borges, Lígia Miranda Ferreira

    2016-06-01

    We have recently shown that repellency of the tick Rhipicephalus sanguineus sensu lato by the tick resistant dog breed, the beagle, is mediated by volatile organic compounds (VOCs) 2-hexanone and benzaldehyde present in beagle odour. Ectoparasite location of animal hosts is affected by variation in these odour components and their ratios. The aim of this study was to quantify the release rate, and the ratio, of 2-hexanone and benzaldehyde from beagles. The odour of three beagles was collected, for four days, over one week (day 0, day 1, day 4 and day 7). The compounds were identified using coupled high-resolution gas chromatography-mass spectrometry (GC-MS), and authentic standards of compounds were used to generate external calibration curves for quantification. Both compounds were found in all dogs on all days. The amount of benzaldehyde was always higher than that of 2-hexanone and so their ratio varied from unity, on average (over time) being 3.128±0.365, 1.902±0.390, 1.670±0.671ngmL(-1) for beagle 1, 2 and 3, respectively. There was no significant (pbenzaldehyde in beagle odour samples covering a 7-day period. This knowledge enables development of repellents to protect dogs from R. sanguineus s. l. infestation.

  3. Polyoxometalate coordinated transition metal complexes as catalysts: Oxidation of styrene to benzaldehyde/benzoic acid

    Indian Academy of Sciences (India)

    Srinivasa Rao Amanchi; Anjali Patel; Samar K Das

    2014-11-01

    Oxidation of styrene is carried out by using heptamolybdate coordinated transition metal (Co2+, Zn2+) complexes, [2-ampH]4[{Co(H2O)5}Mo7O24]·9H2O (1), [3-ampH]4[{Co(H2O)5}Mo7O24]·9H2O (2), [2-ampH]4[{Zn(H2O)5}Mo7O24]·4H2O (3) and [3-ampH]4[{Zn(3-ampy)(H2O)4}Mo7O24]·4H2O (4) as catalysts and H2O2 as an oxidant at 80°C. The leaching study has been carried out to check the quality of catalyst and it has been reused for three times with good percentage of conversion. For the first two catalysts (compounds 1 and 2), the major product obtained is benzaldehyde, and benzoic acid is the major product for next two catalysts (compounds 3 and 4). Stability of the catalysts has been analyzed by IR, UV-spectroscopy and powder X-ray crystallography.

  4. Amorphous metal-aluminophosphate catalysts for aldol condensation of n-heptanal and benzaldehyde to jasminaldehyde

    Institute of Scientific and Technical Information of China (English)

    A. Hamza; N. Nagaraju

    2015-01-01

    Amorphous aluminophosphate (AlP) and metal‐aluminophosphates (MAlPs, where M=2.5 mol%Cu, Zn, Cr, Fe, Ce, or Zr) were prepared by coprecipitation method. Their surface properties and catalytic activity for the synthesis of jasminaldehyde through the aldol condensation of n‐heptanal and benzaldehyde were investigated. The nitrogen adsorption‐desorption isotherms showed that the microporosity exhibited by the aluminophosphate was changed to a mesoporous and macroporous structure which depended on the metal incorporated, with a concomitant change in the surface area. Temperature‐programmed desorption of NH3 and CO2 revealed that the materials possessed both acidic and basic sites. The acidic strength of the material was either increased or decreased depending on the nature of the metal. The basicity was increased compared to AlP. All the materials were X‐ray amorphous and powder X‐ray diffraction studies indicated the absence of metal oxide phases. The Fourier transform infrared analysis confirmed the presence of phosphate groups and also the absence of any M‐O moieties in the materials. The selected organic reaction occurred only in the presence of the AlP and MAlPs. The selectivity for the jasminaldehyde product was up to 75%with a yield of 65%. The best conversion of n‐heptanal with a high selectivity to jasminaldehyde was obtained with FeAlP as the catalyst, and this material was characterized to have less weak acid sites and more basic sites.

  5. Benzaldehyde thiosemicarbazone derived from limonene complexed with copper induced mitochondrial dysfunction in Leishmania amazonensis.

    Directory of Open Access Journals (Sweden)

    Elizandra Aparecida Britta

    Full Text Available BACKGROUND: Leishmaniasis is a major health problem that affects more than 12 million people. Treatment presents several problems, including high toxicity and many adverse effects, leading to the discontinuation of treatment and emergence of resistant strains. METHODOLOGY/PRINCIPAL FINDINGS: We evaluated the in vitro antileishmanial activity of benzaldehyde thiosemicarbazone derived from limonene complexed with copper, termed BenzCo, against Leishmania amazonensis. BenzCo inhibited the growth of the promastigote and axenic amastigote forms, with IC(50 concentrations of 3.8 and 9.5 µM, respectively, with 72 h of incubation. Intracellular amastigotes were inhibited by the compound, with an IC(50 of 10.7 µM. BenzCo altered the shape, size, and ultrastructure of the parasites. Mitochondrial membrane depolarization was observed in protozoa treated with BenzCo but caused no alterations in the plasma membrane. Additionally, BenzCo induced lipoperoxidation and the production of mitochondrial superoxide anion radicals in promastigotes and axenic amastigotes of Leishmania amazonensis. CONCLUSION/SIGNIFICANCE: Our studies indicated that the antileishmania activity of BenzCo might be associated with mitochondrial dysfunction and oxidative damage, leading to parasite death.

  6. Structure and Luminescence Property of a Hexanuclear Silver(Ⅰ) Cluster Containing Benzaldehyde Thiosemicarbazone

    Institute of Scientific and Technical Information of China (English)

    SUN Qiao-Zhen

    2011-01-01

    A new hexanuclear silver (I) compound 2 containing thiosemicarbazone with the group of benzene was synthesized and structurally characterized by single-crystal X-ray diffraction, elemental analysis and fluorescence spectrum. The title compound crystallizes in triclinic, space group P with a = 11.611(3), b = 15.610(5), c = 15.624(7) , α = 113.942(6), β = 104.520(6), γ = 104.230(4)°, V = 2304.1(14) 3, C60H77Ag6N22O4.5S6, Mr = 2018.02, Dc = 1.454 g/cm3, μ(MoKα) = 1.435 mm-1, F(000) = 1005, Z = 1, the final R = 0.0468 and wR = 0.1474 for 6608 observed reflections (I 2σ(I)). In the structure, the S atom of the ligand L2 (L2 = benzaldehyde thiosemicarbazone) served as a triply bridged chelator to connect the six silver atoms into a Ag6L26 cluster. The luminescence property of compound 2 was investigated at room temperature.

  7. Assessment of cytotoxic and apoptotic effects of benzaldehyde using different assays.

    Science.gov (United States)

    Ulker, Z; Alpsoy, L; Mihmanli, A

    2013-08-01

    Benzaldehyde (BA) occurs naturally in a number of plants, including cherry, fig and peach fruit and carnation flowers at therapeutic doses. In addition, it is used in cosmetics, personal care products and food as a preservative. In this study, we aimed to determine the cytotoxic and apoptotic effects of different concentrations of BA on cultured human lymphocytes using lactate dehydrogenase assay, cell proliferation (water-soluble tetrazolium salts-1) assay and terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) test (apoptotic test) as a group of cytotoxicity tests at 6th and 24th h on human lymphocyte cell culture. The cytotoxicity increased when cells were treated with 10, 25 and 50 μg/mL concentrations of BA (p < 0.05). Moreover, treatment of the cells with the same concentrations significantly decreased the cell number at the 6th and 24th hours (p < 0.05). TUNEL assay results also show that the concentration of BA at 10, 25 and 50 μg/mL caused DNA damage significantly (p < 0.05). According to our results, the toxic and genotoxic effects of BA have to be further evaluated before using in cosmetic and food products.

  8. A nanoporous 3D zinc(II) metal–organic framework for selective absorption of benzaldehyde and formaldehyde

    Energy Technology Data Exchange (ETDEWEB)

    Moradpour, Tahereh [School of Chemistry, College of Science, University of Tehran, Tehran (Iran, Islamic Republic of); Abbasi, Alireza, E-mail: aabbassi@khayam.ut.ac.ir [School of Chemistry, College of Science, University of Tehran, Tehran (Iran, Islamic Republic of); Van Hecke, Kristof [XStruct, Department of Inorganic and Physical Chemistry, Ghent University, Krigslaan 281-S3, Ghent B-9000 (Belgium)

    2015-08-15

    A new 3D nanoporous metal–organic framework (MOF), [[Zn{sub 4}O(C{sub 24}H{sub 15}N{sub 6}O{sub 6}){sub 2}(H{sub 2}O){sub 2}]·6H{sub 2}O·DMF]{sub n} (1) based on 4,4′,4″-s-triazine-1,3,5-triyltri-p-aminobenzoate (TATAB) ligand was solvothermally synthesized and characterized by single–crystal X-ray diffraction, Powder X-ray diffraction (PXRD), infrared spectroscopy (IR) and Brunauer–Emmett–Teller (BET) analyses. X-ray single crystal diffraction analysis reveals that 1 exhibits a 3D network with new kvh1 topology. Semi-empirical (AM1) calculations were carried out to obtain stable conformers for TATAB ligand. In addition, the absorption of two typical aldehydes (benzaldehyde and formaldehyde) in the presence of 1 was investigated and the effect of the aldehyde concentration, exposure time and temperature was studied. It was found that compound 1 has a potential for the absorption of aldehydes under mild conditions. - Graphical abstract: Absorption of two typical aldehydes (formaldehyde and benzaldehyde) by solvothermally synthesized of a 3D nano-porous MOF based on TATAB tricarboxylate ligand and Zn (NO{sub 3}){sub 2}·6H{sub 2}O. - Highlights: • We present a 3D Zn(II)-MOF with TATAB linker by solvothermal method. • The framework possesses a new kvh1 topology. • The framework displays formaldehyde and benzaldehyde absorption property. • Conformational analysis was performed to determine the stable linker geometry.

  9. Isolation of liver aldehyde oxidase containing fractions from different animals and determination of kinetic parameters for benzaldehyde

    Directory of Open Access Journals (Sweden)

    Kadam R

    2008-01-01

    Full Text Available Aldehyde oxidase activity containing fractions from rabbit, guinea pig, rat and mouse livers were obtained by heat treatment and ammonium sulfate precipitation. Aldehyde oxidase activity was observed in rabbit and guinea pig livers, while aldehyde oxidase activity was absent in rat and mouse liver fractions. Enzyme kinetic parameters, K m and V max , were determined for the oxidation of benzaldehyde to benzoic acid by rabbit and guinea pig liver fractions, by spectrophotometric method, with potassium ferricyanide as the electron acceptor. The K m values obtained for both animal liver fractions were in the range of 10.3-19.1 µM.

  10. β-cyclodextrin functionalized on glass micro-particles: A green catalyst for selective oxidation of toluene to benzaldehyde

    Science.gov (United States)

    Tahir, M. Nazir; Nielsen, Thorbjørn T.; Larsen, Kim L.

    2016-12-01

    Oxidation of toluene is considered an important process which often requires high temperatures and specific conditions along with heavy-metals based catalysts. In this study, we have developed a green catalyst by functionalizing beta-cyclodextrin onto glass micro-particle surfaces. All surfaces were characterized by X-ray photoelectron spectroscopy and applied to catalyze the selective oxidation of toluene into benzaldehyde (82% yield) at room temperature. The catalyst was stable and could be used repeatedly for several cycles without losing efficiency.

  11. 4-{Phenyl[4-(6-phenyl-2,2′-bipyridin-4-ylphenyl]amino}benzaldehyde

    Directory of Open Access Journals (Sweden)

    Yu-yang Zhang

    2014-08-01

    Full Text Available The title molecule, C35H25N3O, is a triphenylamine derivative with the 4-position substituted by an aldehyde group, and the 4′-position substituted by a 6-phenyl-2,2′-bipyridine group. The whole molecule is non-planar and the dihedral angle between the core benzene and pyridine rings is 36.96 (5°. The dihedral angle between the phenyl and benzaldehyde groups bonded to the amine N atom is 70.86 (5°.

  12. Toluene oxidization to benzaldehyde in subcritical water%近临界水中甲苯氧化生成苯甲醛

    Institute of Scientific and Technical Information of China (English)

    朱宪; 王倩

    2006-01-01

    Effects of reaction parameter on yield of benzaldehyde produced from toluene oxidization using hydrogen peroxide in subcriti cal water are investigated. The experimental results show that if the molar ratio of hydrogen peroxide to toluene is controlled within a reasonable range, the by-products may be neglected. The optimum technology of toluene oxidization to benzaldehyde is reaction time 60 min,reaction temperature 350 ℃, molar ratio of hydrogen peroxide to toluene 3.5. The yield of benzaldehyde can reach 17.2% under the optimum condition. Research results of chemical reaction kinetics show that the consecutive reaction consists of two first-order reaction, and activation energy of these two reactions are 89 kJ· mol-1 and 76 kJ· mol-1 respectively.

  13. Rapid and sensitive determination of benzaldehyde arising from benzyl alcohol used as preservative in an injectable formulation solution using dispersive liquid-liquid microextraction followed by gas chromatography.

    Science.gov (United States)

    Mashayekhi, Hossein Ali; Rezaee, Mohammad; Garmaroudi, Shirin Sadeghi; Montazeri, Naser; Ahmadi, Seyed Javad

    2011-01-01

    A rapid and sensitive method has been developed for the determination of benzaldehyde, a toxic oxidation product of the widely used preservative and co-solvent benzyl alcohol in injectable formulations of non-steroidal anti-inflammatory drugs, diclofenac, vitamin B-complex and Voltaren injection solutions by using dispersive liquid-liquid microextraction followed by gas chromatography. This method involves the use of an appropriate mixture of extraction solvent (43.0 µL 1,2-dichloroethane) and disperser solvent (1.0 mL acetonitrile) for the formation of a cloudy solution in a 5.0-mL aqueous sample containing benzaldehyde. The linear range was 1.0-1000 µg L(-1), and the limit of detection was 0.2 µg L(-1) for benzaldehyde.

  14. 氨基磺酸催化合成苯甲醛乙二醇缩醛%Synthesis of Benzaldehyde Ethylene Glycol Acetal with Aminosulfonic Acid as Catalyst

    Institute of Scientific and Technical Information of China (English)

    王俏; 张玉琦; 魏清勃

    2013-01-01

    The benzaldehyde ethylene glycol acetal was synthesized from benzaldehyde and ethylene glycol in the presence of aminosulfonic acid which was used as catalyst.The effects of molar ratio of benzaldehyde to ethylene glycol,reaction time,amount of catalyst and water carrying agent,etc.on the yield of benzaldehyde ethylene glycol acetal were investigated.The best reaction conditions were found as follows:n(benzaldehyde):n (ethylene glycol)=1:1.5,the mass ratio of aminosulfonic acid was 1.5% of total reactants,the water carrying agent was 16mL (2.18% of total reactants) and the reaction time was 1.5h.Under these conditions,the yield of benzaldehyde ethylene glycol acetal could reach 83.73%.%以氨基磺酸为催化剂合成了苯甲醛乙二醇缩醛,考察了醛醇摩尔比,反应时间,催化剂用量,带水剂用量等因素对苯甲醛乙二醇缩醛收率的影响.结果表明:最适宜的工艺条件是:n(苯甲醛):n(乙二醇)=1:1.5,催化剂用量占反应物总质量的1.5%,带水剂环己烷用量为16mL(占反应物总质量的2.18%),反应时间1.5h,上述条件下,苯甲醛乙二醇缩醛收率可达到83.73%.

  15. Electrical Wiring of the Aldehyde Oxidoreductase PaoABC with a Polymer Containing Osmium Redox Centers: Biosensors for Benzaldehyde and GABA

    Directory of Open Access Journals (Sweden)

    Artavazd Badalyan

    2014-11-01

    Full Text Available Biosensors for the detection of benzaldehyde and g-aminobutyric acid (GABA are reported using aldehyde oxidoreductase PaoABC from Escherichia coli immobilized in a polymer containing bound low potential osmium redox complexes. The electrically connected enzyme already electrooxidizes benzaldehyde at potentials below −0.15 V (vs. Ag|AgCl, 1 M KCl. The pH-dependence of benzaldehyde oxidation can be strongly influenced by the ionic strength. The effect is similar with the soluble osmium redox complex and therefore indicates a clear electrostatic effect on the bioelectrocatalytic efficiency of PaoABC in the osmium containing redox polymer. At lower ionic strength, the pH-optimum is high and can be switched to low pH-values at high ionic strength. This offers biosensing at high and low pH-values. A “reagentless” biosensor has been formed with enzyme wired onto a screen-printed electrode in a flow cell device. The response time to addition of benzaldehyde is 30 s, and the measuring range is between 10–150 µM and the detection limit of 5 µM (signal to noise ratio 3:1 of benzaldehyde. The relative standard deviation in a series (n = 13 for 200 µM benzaldehyde is 1.9%. For the biosensor, a response to succinic semialdehyde was also identified. Based on this response and the ability to work at high pH a biosensor for GABA is proposed by coimmobilizing GABA-aminotransferase (GABA-T and PaoABC in the osmium containing redox polymer.

  16. Electrical Wiring of the Aldehyde Oxidoreductase PaoABC with a Polymer Containing Osmium Redox Centers: Biosensors for Benzaldehyde and GABA.

    Science.gov (United States)

    Badalyan, Artavazd; Dierich, Marlen; Stiba, Konstanze; Schwuchow, Viola; Leimkühler, Silke; Wollenberger, Ulla

    2014-12-01

    Biosensors for the detection of benzaldehyde and γ-aminobutyric acid (GABA) are reported using aldehyde oxidoreductase PaoABC from Escherichia coli immobilized in a polymer containing bound low potential osmium redox complexes. The electrically connected enzyme already electrooxidizes benzaldehyde at potentials below -0.15 V (vs. Ag|AgCl, 1 M KCl). The pH-dependence of benzaldehyde oxidation can be strongly influenced by the ionic strength. The effect is similar with the soluble osmium redox complex and therefore indicates a clear electrostatic effect on the bioelectrocatalytic efficiency of PaoABC in the osmium containing redox polymer. At lower ionic strength, the pH-optimum is high and can be switched to low pH-values at high ionic strength. This offers biosensing at high and low pH-values. A "reagentless" biosensor has been formed with enzyme wired onto a screen-printed electrode in a flow cell device. The response time to addition of benzaldehyde is 30 s, and the measuring range is between 10-150 µM and the detection limit of 5 µM (signal to noise ratio 3:1) of benzaldehyde. The relative standard deviation in a series (n = 13) for 200 µM benzaldehyde is 1.9%. For the biosensor, a response to succinic semialdehyde was also identified. Based on this response and the ability to work at high pH a biosensor for GABA is proposed by coimmobilizing GABA-aminotransferase (GABA-T) and PaoABC in the osmium containing redox polymer.

  17. Polymer characterization and optimization of conditions for the enhanced bioproduction of benzaldehyde by Pichia pastoris in a two-phase partitioning bioreactor.

    Science.gov (United States)

    Craig, Tom; Daugulis, Andrew J

    2013-04-01

    Benzaldehyde, with its apricot and almond-like aroma, is the second most abundantly used molecule in the flavor industry, and is most commonly produced via chemical routes, such as by the oxidation of toluene. Biologically produced benzaldehyde, whether by extraction of plant material or via microbial biotransformation, commands a substantial price advantage, and greater consumer acceptance. Methylotrophic yeast, such as Pichia pastoris, contain the enzyme alcohol oxidase (AOX), which, in the presence of alcohols other than methanol, are able to yield aldehydes as dead-end products, for example, benzaldehyde from benzyl alcohol. In this work, we have determined that benzaldehyde, and not benzyl alcohol, is inhibitory to the transformation reaction by P. pastoris, prompting the development of a selection strategy for identifying sequestering polymers for use in a partitioning bioreactor that was based on the ratio of partition coefficients (PCs) for the two target molecules. Additionally, we have now confirmed for the first time, that the mechanism of solute uptake by amorphous polymers is via absorption, not adsorption. Finally, we have adopted a common strategy used for the production of heterologous proteins by P. pastoris, namely the use of a mixed methanol/glycerol feed for inducing the required AOX enzyme, while reducing the time required for high density biomass generation. All of these components were combined in a final experiment in which 10% of the polymer Kraton D1102K, whose PC ratio of benzaldehyde to benzyl alcohol was 14.9, was used to detoxify the biotransformation in a 5 L partitioning bioreactor, resulting in a 3.4-fold increase in benzaldehyde produced (14.4 g vs. 4.2 g) relative to single phase operation, at more than double the volumetric productivity (97 mg L(-1) h(-1) vs. 41 mg L(-1) h(-1) ).

  18. Effects of HCl and HNO3 on the oxidation of toluene to benzaldehyde by H2O2 over TS-1 modified with Al in aqueous phase

    Directory of Open Access Journals (Sweden)

    Paricha Pongjirawat

    2014-09-01

    Full Text Available This research studies effects of HCl and HNO3 in aqueous solution on the oxidation reaction between toluene and hydrogen peroxide to benzaldehyde over titanium silicalite-1 catalyst modified with Al. The reaction was carried out at reaction temperature 120°C in a pressurized autoclave reactor. The research found that the addition of HCl and HNO3 not only increases the concentration of toluene in the aqueous phase but also increases the formation of benzaldehyde as main product in the reaction.

  19. 2-Phenyl-tetrahydropyrimidine-4(1H-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

    Directory of Open Access Journals (Sweden)

    Markus Nahrwold

    2009-09-01

    Full Text Available Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R-β2-homoaspartate.

  20. Vibrational, NMR and UV-visible spectroscopic investigation and NLO studies on benzaldehyde thiosemicarbazone using computational calculations

    Science.gov (United States)

    Moorthy, N.; Prabakar, P. C. Jobe; Ramalingam, S.; Pandian, G. V.; Anbusrinivasan, P.

    2016-04-01

    In order to investigate the vibrational, electronic and NLO characteristics of the compound; benzaldehyde thiosemicarbazone (BTSC), the XRD, FT-IR, FT-Raman, NMR and UV-visible spectra were recorded and were analysed with the calculated spectra by using HF and B3LYP methods with 6-311++G(d,p) basis set. The XRD results revealed that the stabilized molecular systems were confined in orthorhombic unit cell system. The cause for the change of chemical and physical properties behind the compound has been discussed makes use of Mulliken charge levels and NBO in detail. The shift of molecular vibrational pattern by the fusing of ligand; thiosemicarbazone group with benzaldehyde has been keenly observed. The occurrence of in phase and out of phase molecular interaction over the frontier molecular orbitals was determined to evaluate the degeneracy of the electronic energy levels. The thermodynamical studies of the temperature region 100-1000 K to detect the thermal stabilization of the crystal phase of the compound were investigated. The NLO properties were evaluated by the determination of the polarizability and hyperpolarizability of the compound in crystal phase. The physical stabilization of the geometry of the compound has been explained by geometry deformation analysis.

  1. Thiol and Disulfide Derivatives of Ephedra Alkaloids 2 : A Mechanistic Study of Their Effect on the Addition of Diethyl Zinc to Benzaldehyde

    NARCIS (Netherlands)

    Fitzpatrick, Kevin; Hulst, Ron; Kellogg, Richard M.

    1995-01-01

    Thiol and disulfide derivatives of ephedrine have been shown previously to catalyse in high enantiomeric excess (ee) the reaction of diethyl zinc with benzaldehyde. We find that this reaction involves non-linear correlations between the ee of product and catalyst. Osmotic measurements indicate a hig

  2. Enhanced sensitivity of self-assembled-monolayer-based SPR immunosensor for detection of benzaldehyde using a single-step multi-sandwich immunoassay.

    Science.gov (United States)

    Gobi, K Vengatajalabathy; Matsumoto, Kiyoshi; Toko, Kiyoshi; Ikezaki, Hidekazu; Miura, Norio

    2007-04-01

    This paper describes the fabrication and sensing characteristics of a self-assembled monolayer (SAM)-based surface plasmon resonance (SPR) immunosensor for detection of benzaldehyde (BZ). The functional sensing surface was fabricated by the immobilization of a benzaldehyde-ovalbumin conjugate (BZ-OVA) on Au-thiolate SAMs containing carboxyl end groups. Covalent binding of BZ-OVA on SAM was found to be dependent on the composition of the base SAM, and it is improved very much with the use of a mixed monolayer strategy. Based on SPR angle measurements, the functional sensor surface is established as a compact monolayer of BZ-OVA bound on the mixed SAM. The BZ-OVA-bound sensor surface undergoes immunoaffinity binding with anti-benzaldehyde antibody (BZ-Ab) selectively. An indirect inhibition immunoassay principle has been applied, in which analyte benzaldehyde solution was incubated with an optimal concentration of BZ-Ab for 5 min and injected over the sensor chip. Analyte benzaldehyde undergoes immunoreaction with BZ-Ab and makes it inactive for binding to BZ-OVA on the sensor chip. As a result, the SPR angle response decreases with an increase in the concentration of benzaldehyde. The fabricated immunosensor demonstrates a low detection limit (LDL) of 50 ppt (pg mL(-1)) with a response time of 5 min. Antibodies bound to the sensor chip during an immunoassay could be detached by a brief exposure to acidic pepsin. With this surface regeneration, reusability of the same sensor chip for as many as 30 determination cycles has been established. Sensitivity has been enhanced further with the application of an additional single-step multi-sandwich immunoassay step, in which the BZ-Ab bound to the sensor chip was treated with a mixture of biotin-labeled secondary antibody, streptavidin and biotin-bovine serum albumin (Bio-BSA) conjugate. With this approach, the SPR sensor signal increased by ca. 12 times and the low detection limit improved to 5 ppt with a total response

  3. Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structure-microbicidal activity relationship.

    Science.gov (United States)

    Xia, Lei; Xia, Yu-Fen; Huang, Li-Rong; Xiao, Xiao; Lou, Hua-Yong; Liu, Tang-Jingjun; Pan, Wei-Dong; Luo, Heng

    2015-06-05

    There is an urgent need to develop new antibacterial agents because of multidrug resistance by bacteria and fungi. Schiff bases (aldehyde or ketone-like compounds) exhibit intense antibacterial characteristics, and are therefore, promising candidates as antibacterial agents. To investigate the mechanism of action of newly designed benzaldehyde Schiff bases, a series of high-yielding benzaldehyde Schiff bases were synthesized, and their structures were determined by NMR and MS spectra data. The structure-microbicidal activity relationship of derivatives was investigated, and the antibacterial mechanisms were investigated by gene assays for the expression of functional genes in vitro using Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The active compounds were selective for certain active groups. The polar substitution of the R2 group of the amino acids in the Schiff bases, affected the antibacterial activity against E. coli and S. aureus; specific active group at the R3 or R4 groups of the acylhydrazone Schiff bases could improve their inhibitory activity against these three tested organisms. The antibacterial mechanism of the active benzaldehyde Schiff bases appeared to regulate the expression of metabolism-associated genes in E. coli, hemolysis-associated genes in B. subtilis, and key virulence genes in S. aureus. Some benzaldehyde Schiff bases were bactericidal to all the three strains and appeared to regulate gene expression associated with metabolism, hemolysis, and virulence, in vitro. The newly designed benzaldehyde Schiff bases possessed unique antibacterial activity and might be potentially useful for prophylactic or therapeutic intervention of bacterial infections.

  4. Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety:Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    A series of novel N,O-type chiral ligands derived from enantiopure inherently chiral calix[4]arenes containing quinolin-2-yl-methanol moiety in the cone or partialcone conformation have been synthe-sized and characterized. Moreover,they have been applied to the catalytic asymmetric addition of diethylzinc to benzaldehyde,which represents the first example that the inherently chiral calixarene can be used as the chiral ligands for the catalytic asymmetric synthesis.

  5. Selective liquid phase oxidation of benzyl alcohol to benzaldehyde by tert-butyl hydroperoxide over γ-Al2O3 supported copper and gold nanoparticles

    Science.gov (United States)

    Ndolomingo, Matumuene Joe; Meijboom, Reinout

    2017-03-01

    Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide (TBHP) in the absence of any solvent using γ-Al2O3 supported copper and gold nanoparticles. Li2O and ionic liquids were used as additive and stabilizers for the synthesis of the catalysts. The physico-chemical properties of the catalysts were characterized by atomic absorption spectroscopy (AAS), X-ray diffraction spectroscopy (XRD), N2 absorption/desorption (BET), transmission electron microscopy (TEM), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and temperature programmed reduction (TPR), whereas, the oxidation reaction was followed by gas chromatography with a flame ionization detector (GC-FID). The as prepared catalysts exhibited good catalytic performance in terms of conversion and selectivity towards benzaldehyde. The performance of the Au-based catalysts is significantly higher than that of the Cu-based catalysts. For both Cu and Au catalysts, the conversion of benzyl alcohol increased as the reaction proceeds, while the selectivity for benzaldehyde decreased. Moreover, the catalysts can be easily recycled and reused with neither significant loss of activity nor selectivity. A kinetic study for the Cu and Au-catalyzed oxidation of benzyl alcohol to benzyldehyde is reported. The rate at which the oxidation of benzyl alcohol is occurring as a function of catalyst and oxidant amounts was investigated, with the apparent rate constant, kapp being proportional to the amount of nano catalyst and oxygen present in the system.

  6. Gas Phase Selective Catalytic Oxidation of Toluene to Benzaldehyde on V2O5-Ag2O/η-Al2O3 Catalyst

    Institute of Scientific and Technical Information of China (English)

    Tonglai Zhang; Liqiu Mao; Weihua Liu

    2004-01-01

    Gas phase selective catalytic oxidation of toluene to benzaldehyde was studied on V2O5-Ag2O/η-Al2O3 catalyst prepared by impregnation. The catalyst was characterized by XRD, XPS, TEM,and FT-IR. The catalytic results showed that toluene conversion and selectivity for benzaldehyde on catalyst sample No.4 (V/(V+Ag)=0.68) was higher than other catalysts with different V/Ag ratios. This was attributed to the higher surface area, larger pore volume and pore diameter of the catalyst sample No.4 than the other catalysts. The XRD patterns recorded from the catalyst before and after the oxidation reaction revealed that the new phases were developed, and this suggested that silver had entered the vanadium lattice. XPS results showed that the vanadium on the surface of No.4 and No.5 sample was more than that in the bulk, thus forming a vanadium rich layer on the surface. It was noted that when the catalyst was doped by potassium promoter, the toluene conversion and selectivity for benzaldehyde were higher than those on the undoped catalyst. This was attributed to the disordered structure of V2O5 lattice of the K-doped catalyst and a better interfacial contact between the particles.

  7. Suitable combination of promoter and micellar catalyst for kilo fold rate acceleration on benzaldehyde to benzoic acid conversion in aqueous media at room temperature: a kinetic approach.

    Science.gov (United States)

    Ghosh, Aniruddha; Saha, Rumpa; Ghosh, Sumanta K; Mukherjee, Kakali; Saha, Bidyut

    2013-05-15

    The kinetics of oxidation of benzaldehyde by chromic acid in aqueous and aqueous surfactant (sodium dodecyl sulfate, SDS, alkyl phenyl polyethylene glycol, Triton X-100 and N-cetylpyridinium chloride, CPC) media have been investigated in the presence of promoter at 303 K. The pseudo-first-order rate constants (kobs) were determined from a logarithmic plot of absorbance as a function time. The rate constants were found to increase with introduction of heteroaromatic nitrogen base promoters such as Picolinic acid (PA), 2,2'-bipyridine (bipy) and 1,10-phenanthroline (phen). The product benzoic acid has been characterized by conventional melting point experiment, NMR, HRMS and FTIR spectral analysis. The mechanism of both unpromoted and promoted reaction path has been proposed for the reaction. In presence of the anionic surfactant SDS, cationic surfactant CPC and neutral surfactant TX-100 the reaction can undergo simultaneously in both aqueous and micellar phase with an enhanced rate of oxidation in the micellar phase. Both SDS and TX-100 produce normal micellar effect whereas CPC produce reverse micellar effect in the presence of benzaldehyde. The observed net enhancement of rate effects has been explained by considering the hydrophobic and electrostatic interaction between the surfactants and reactants. SDS and bipy combination is the suitable one for benzaldehyde oxidation.

  8. Synthesis, X-ray structure analysis, thermodynamic and electronic properties of 4-acetamido benzaldehyde using vibrational spectroscopy and DFT calculations

    Science.gov (United States)

    Jeeva Jasmine, N.; Arunagiri, C.; Subashini, A.; Stanley, N.; Thomas Muthiah, P.

    2017-02-01

    Theoretical Spectrograms, namely, FT-Raman (3500-50 cm-1) and FT-Infrared (4000-400 cm-1) spectra have been studied for 4-acetamido benzaldehyde (4ABA) and are assigned to different normal modes of the molecule. Vibrational spectral analysis was compared with the experimental and theoretical, FT-IR and FT-Raman spectra. The effect of polarity on the Harmonic vibrational frequencies, intensities, optimized geometrical parameters and several thermodynamic parameters in the ground state have been computed by the B3LYP method using 6-311 + G(d,p) basis set. The results of the optimized molecular structure is presented and compared with the XRD values. The global chemical reactivity relate to some parameters, such as HOMO, LUMO, gap energy (ΔE) and other parameters, including electronegativity (χ) and global hardness (η). The values of the reactivity descriptors indicated that the interaction between 4ABA molecules reduced its reactivity in comparison with the exhibited in gas phase. In addition, the local reactivity has been analyzed through the Fukui function and condensed softness indices.

  9. Using heavy atom rare gas matrix to control the reactivity of 4-methoxybenzaldehyde: A comparison with benzaldehyde

    Energy Technology Data Exchange (ETDEWEB)

    Kus, Nihal [Department of Chemistry, University of Coimbra, 3004-535 Coimbra (Portugal); Department of Physics, Anadolu University, 26470 Eskisehir (Turkey); Sharma, Archna; Reva, Igor; Fausto, Rui [Department of Chemistry, University of Coimbra, 3004-535 Coimbra (Portugal); Lapinski, Leszek [Institute of Physics, Polish Academy of Sciences, Warsaw (Poland)

    2012-04-14

    Different patterns of photochemical behavior were observed for 4-methoxybenzaldehyde (p-anisaldehyde) isolated in xenon and in argon matrices. Monomers of the compound isolated in solid Xe decarbonylate upon middle ultraviolet irradiation, yielding methoxybenzene (anisole), and CO. On the other hand, p-anisaldehyde isolated in an Ar matrix and subjected to identical irradiation, predominantly isomerizes to the closed-ring isomeric ketene (4-methoxycyclohexa-2,4-dien-1-ylidene) methanone. Experimental detection of a closed-ring ketene photoproduct, generated from an aromatic aldehyde, constitutes a rare observation. The difference between the patterns of photochemical transformations of p-anisaldehyde isolated in argon and xenon environments can be attributed to the external heavy-atom effect, where xenon enhances the rate of intersystem crossing from the singlet to the triplet manifold in which decarbonylation (via p-methoxybenzoyl radical) takes place. The parent compound, benzaldehyde, decarbonylates (to benzene + CO) when subjected to middle ultraviolet irradiation in both argon and xenon matrices. This demonstrates the role of the methoxy p-anisaldehyde substituent in activation of the reaction channel leading to the formation of the ketene photoproduct.

  10. A nanoporous 3D zinc(II) metal-organic framework for selective absorption of benzaldehyde and formaldehyde

    Science.gov (United States)

    Moradpour, Tahereh; Abbasi, Alireza; Van Hecke, Kristof

    2015-08-01

    A new 3D nanoporous metal-organic framework (MOF), [[Zn4O(C24H15N6O6)2(H2O)2]·6H2O·DMF]n (1) based on 4,4‧,4″-s-triazine-1,3,5-triyltri-p-aminobenzoate (TATAB) ligand was solvothermally synthesized and characterized by single-crystal X-ray diffraction, Powder X-ray diffraction (PXRD), infrared spectroscopy (IR) and Brunauer-Emmett-Teller (BET) analyses. X-ray single crystal diffraction analysis reveals that 1 exhibits a 3D network with new kvh1 topology. Semi-empirical (AM1) calculations were carried out to obtain stable conformers for TATAB ligand. In addition, the absorption of two typical aldehydes (benzaldehyde and formaldehyde) in the presence of 1 was investigated and the effect of the aldehyde concentration, exposure time and temperature was studied. It was found that compound 1 has a potential for the absorption of aldehydes under mild conditions.

  11. The cytotoxicity of benzaldehyde nitrogen mustard-2-pyridine carboxylic acid hydrazone being involved in topoisomerase IIα inhibition.

    Science.gov (United States)

    Fu, Yun; Zhou, Sufeng; Liu, Youxun; Yang, Yingli; Sun, Xingzhi; Li, Changzheng

    2014-01-01

    The antitumor property of iron chelators and aromatic nitrogen mustard derivatives has been well documented. Combination of the two pharmacophores in one molecule in drug designation is worth to be explored. We reported previously the syntheses and preliminary cytotoxicity evaluation of benzaldehyde nitrogen mustard pyridine carboxyl acid hydrazones (BNMPH) as extended study, more tumor cell lines (IC50 for HepG2: 26.1 ± 3.5 μM, HCT-116: 57.5 ± 5.3 μM, K562: 48.2 ± 4.0 μM, and PC-12: 19.4 ± 2.2 μM) were used to investigate its cytotoxicity and potential mechanism. In vitro experimental data showed that the BNMPH chelating Fe(2+) caused a large number of ROS formations which led to DNA cleavage, and this was further supported by comet assay, implying that ROS might be involved in the cytotoxicity of BNMPH. The ROS induced changes of apoptosis related genes, but the TFR1 and NDRG1 metastatic genes were not obviously regulated, prompting that BNMPH might not be able to deprive Fe(2+) of ribonucleotide reductase. The BNMPH induced S phase arrest was different from that of iron chelators (G1) and alkylating agents (G2). BNMPH also exhibited its inhibition of human topoisomerase IIα. Those revealed that the cytotoxic mechanism of the BNMPH could stem from both the topoisomerase II inhibition, ROS generation and DNA alkylation.

  12. Growth and characterization of benzaldehyde 4-nitro phenyl hydrazone (BPH) single crystal: A proficient second order nonlinear optical material

    Science.gov (United States)

    Saravanan, M.; Abraham Rajasekar, S.

    2016-04-01

    The crystals (benzaldehyde 4-nitro phenyl hydrazone (BPH)) appropriate for NLO appliance were grown by the slow cooling method. The solubility and metastable zone width measurement of BPH specimen was studied. The material crystallizes in the monoclinic crystal system with noncentrosymmetric space group of Cc. The optical precision in the whole visible region was found to be excellent for non-linear optical claim. Excellence of the grown crystal is ascertained by the HRXRD and etching studies. Laser Damage Threshold and Photoluminescence studies designate that the grown crystal contains less imperfection. The mechanical behaviour of BPH sample at different temperatures was investigated to determine the hardness stability of the grown specimen. The piezoelectric temperament and the relative Second Harmonic Generation (for diverse particle sizes) of the material were also studied. The dielectric studies were executed at varied temperatures and frequencies to investigate the electrical properties. Photoconductivity measurement enumerates consummate of inducing dipoles due to strong incident radiation and also divulge the nonlinear behaviour of the material. The third order nonlinear optical properties of BPH crystals were deliberate by Z-scan method.

  13. Growth and characterization of novel organic 3-Hydroxy Benzaldehyde-N-methyl 4 Stilbazolium Tosylate crystals for NLO applications

    Science.gov (United States)

    Jagannathan, K.; Umarani, P.; Ratchagar, V.; Ramesh, V.; Kalainathan, S.

    2016-01-01

    The 3-Hydroxy Benzaldehyde-N-methyl 4-Stilbazolium Tosylate (3- HBST) is a new organic NLO crystal and it is a new derivative in stilbazolium tosylate family. In this work we have synthesized 3-HBST and the single crystal was grown by conventional slow cooling method. The structure and lattice parameters of the grown crystal were determined by the single crystal X-ray diffraction (XRD) technique and it is exhibiting good crystalline nature which is observed from the powder XRD. In order to check the crystalline quality the rocking curve was recorded using multi crystal X-ray diffractometer. The functional groups were identified from both FTIR and NMR spectral analyses. The π-π* and n-π* optical transition energy levels were estimated from the absorption peaks. The NLO property was confirmed by measuring relative SHG efficiency by Kurtz powder test; it shows 24 times higher SHG efficiency than that of urea. In order to test the mechanical stability the Vickers and Knoop micro hardness measurement were carried out and found that the micro hardness number decreases with increasing load. The melting point was determined from Differential Scanning Colorimetry (DSC).

  14. The Production of Benzaldehyde by Rhizopus oligosporus USM R1 in a Solid State Fermentation (SSF) System of Soy Bean Meal: Rice Husks

    OpenAIRE

    Norliza, A. W.; Ibrahim, C. O.

    2005-01-01

    The cultivation of Rhizopus oligosporus USM R1 for the production of benzaldehyde, a bitter cherry almond flavour was performed using soya bean meal and rice husks as the substrates. The identification of R. oligosporus USM R1 was performed based on the observation made under light microscope and scanning electron microscope (SEM). The optimum conditions for the SSF in a 250-ml Erlenmeyer flask system were 40% (v/w) water content, substrate particle size of 0.7 mm; inoculum size of 1 x 10^5 s...

  15. Influence of basic properties of Mg,Al-mixed oxides on their catalytic activity in knoevenagel condensation between benzaldehyde and phenylsulfonylacetonitrile

    Directory of Open Access Journals (Sweden)

    Caridad Noda Pérez

    2009-01-01

    Full Text Available The catalytic performance of Mg,Al-mixed oxides (MO20, MO25 and MO33 derived from hydrotalcites was evaluated in the Knoevenagel reaction between benzaldehyde and phenylsulfonylacetonitrile at 373 and 383 K. The best results were obtained for the sample MO20 that presented the highest basic sites density and external area and the smallest crystallite sizes. The relative amount of basic sites with weak to intermediate strength also played an important role on catalytic performance. By increasing the catalyst content from 1 to 5 wt.% at 383 K, a complete conversion of the reactants is attained, producing α-phenylsulfonylcinnamonitrile with a selectivity of 100%.

  16. Density, Viscosity, Sound Speed, and Thermoacoustical Parameters of Benzaldehyde with Chlorobenzene or Nitrobenzene at 303.15 K, 308.15 K, and 313.15 K

    Science.gov (United States)

    Lavanya, T. G.; Saravanakumar, K.; Baskaran, R.; Kubendran, T. R.

    2013-07-01

    The values of the density, viscosity, and speed of sound for binary liquid mixtures of benzaldehyde with chlorobenzene or nitrobenzene have been measured over the entire range of composition at (303.15, 308.15, and 313.15) K. These values have been used to calculate the excess molar volume (), and excess free volume (). McAllister's three-body interaction model is used for correlating the kinematic viscosity of binary mixtures. The thermophysical properties (density, viscosity, and ultrasonic velocity) under study were fit to the Jouyban-Acree model.

  17. Pestalols A-E, new alkenyl phenol and benzaldehyde derivatives from endophytic fungus Pestalotiopsis sp. AcBC2 isolated from the Chinese mangrove plant Aegiceras corniculatum.

    Science.gov (United States)

    Sun, Jian-Fan; Lin, Xiuping; Zhou, Xue-Feng; Wan, Junting; Zhang, Tianyu; Yang, Bin; Yang, Xian-Wen; Tu, Zhengchao; Liu, Yonghong

    2014-06-01

    Five alkenyl phenol and benzaldehyde derivatives, pestalols A-E (1-5), as well as seven known compounds (6-12), were isolated from endophytic fungus Pestalotiopsis sp. AcBC2 derived from the Chinese mangrove plant Aegiceras corniculatum. Their structures were determined by spectroscopic analyses. Compounds 2 and 3 showed cytotoxicity against a panel of 10 tumor cell lines. Compounds 1-5, 8, 9, 11, and 12 showed inhibitory activities against Influenza A virus subtype (H3N2) and Swine Flu (H1N1) viruses. Compound 2 also showed inhibitory activity against tuberculosis.

  18. Effect of manganese and potassium addition on CeO2-Al2O3 catalyst for hydrogenation of benzoic acid to benzaldehyde

    Institute of Scientific and Technical Information of China (English)

    CHENG; Dangguo; HOU; Chunyang; CHEN; Fengqiu; ZHAN; Xiaol

    2009-01-01

    A series of Mn/CeO2-Al2O3 and K/CeO2-Al2O3 catalysts for hydrogenation of benzoic acid to benzaldehyde were prepared to in-vestigate the effect of Mn, K addition on CeO2-Al2O3 catalyst. X-ray diffraction (XRD) and H2-temperature-programmed reduction (H2-TPR) results suggested that the interaction between CeO2 and MnOx enhanced the reducibility of catalysts and therefore benzoic acid conversion.The addition of K increased the number of basic number on the catalyst which leads to a high selectivity to benzaldehyde, but excessive addition imposed negative effects on the catalyst performance. A Mn-K/CeO2Al2O3 catalyst was developed and investigated in the reaction. The simul-taneous addition of Mn and K enhanced not only the catalytic activity but also the capacity to resist the coke formation over catalyst.

  19. [Application of gas chromatography-high resolution quadrupole time of flight mass spectrometry to the analysis of benzaldehyde, benzyl alcohol acetophenone and phenylacetaldehyde in complex aromatic samples].

    Science.gov (United States)

    Liu, Junyan; Cao, Zhe; Li, Jiwen; Wang, Zheming; Wang, Chuan; Gu, Songyuan

    2015-02-01

    The study focuses on the quantitative analytical characterization of benzaldehyde, benzyl alcohol, acetophenone and phenylacetaldehyde in complex aromatic samples by gas chromatography-high resolution quadrupole time of flight mass spectrometry (GC-QTOF MS). The four compounds in real sample were accurately qualified and quantified through a comprehensive analysis of the GC retention times and the accurate masses of the ion fragments obtained by the high resolution MS. The new method therefore effectively avoids the interference of the real sample substrate, which reduces the accuracy of the analysis results. The peak area of the characteristic ion fragment for each compound was used for quantitation calculation. The MS signal responses of the four compounds showed good linear relationships with the corresponding mass concentrations and the linear regression coefficients were greater than 0. 99. The method recoveries were 87. 97% - 103.01%. The limits of detection (LODs) were 0. 01, 0. 03, 0. 02 and 0. 01 mg/L for benzaldehyde, benzyl alcohol, acetophenone and phenylacetaldehyde respectively. The contents of the four compounds in three real samples were analyzed. The study provided a new strategy for oxygenate analysis in complex aromatic samples using GC-QTOF MS. By measuring the accurate masses, the new method reduces the reliance on chromatographic separation ability and makes up the shortcomings of the traditional GC-MS methods.

  20. Benzaldehyde thiosemicarbazone monohydrate

    Directory of Open Access Journals (Sweden)

    Sheng-Jiu Gu

    2008-08-01

    Full Text Available In the title compound, C8H9N3S·H2O, intramolecular N—H...N hydrogen bonding contributes to the molecular conformation. Water molecules are involved in intermolecular N—H...O and O—H...S hydrogen bonds, which link the molecules into ribbons extended along the a axis. Weak intermolecular N—H...S hydrogen bonds link these ribbons into layers parallel to the ab plane with the phenyl rings pointing up and down.

  1. Enzymatic reduction of 4-(dimethylamino)benzaldehyde with carrot bits (Daucus carota): a simple experiment for understanding biocatalysis; Reducao enzimatica do 4-(dimetilamino)benzaldeido com pedacos de cenoura (Daucus carota): um experimento simples na compreensao da biocatalise

    Energy Technology Data Exchange (ETDEWEB)

    Omori, Alvaro Takeo; Portas, Viviane Barbosa; Oliveira, Camila de Souza de, E-mail: alvaro.omori@ufabc.edu.br [Centro de Ciencias Naturais e Humanas, Universidade Federal do ABC, SP (Brazil)

    2012-07-01

    The present paper describes a simple, low-costly and environmentally friendly procedure for reduction of 4-(dimethylamino)benzaldehyde using carrot bits in water. This interdisciplinary experiment can be used to introduce the concepts of biocatalysis and green chemistry to undergraduate students. (author)

  2. OZONE REACTION WITH N-ALDEHYDES (N=4-10), BENZALDEHYDE, ETHANOL, ISOPROPANOL, AND N-PROPANOL ADSORBED ON A DUAL-BED GRAPHITIZED CARBON/CARBON MOLECULAR SIEVE ADSORBENT CARTRIDGE

    Science.gov (United States)

    Ozone reacts with n-aldehydes (n = 4 - 10), benzaldehyde, ethanol, isopropanol, and n-propanol adsorbed on a dual-bed graphitized carbon/carbon molecular sieve adsorbent cartridge. Destruction of n-aldehydes increases with n number and with ozone concentration. In some samp...

  3. Synthesis of naphthalene-naphthol-benzaldehyde pitch resin%萘-萘酚-苯甲醛沥青树脂的合成研究

    Institute of Scientific and Technical Information of China (English)

    周广明; 赖仕全; 岳莉; 赵雪飞; 李小侠; 王荣荣

    2012-01-01

    Naphthalene -naphtho]-berzaldlehyde three components pitch resin has been synthesized by cationic polymerization in the presence of concentrated sulfuric acid, in which the naphtho] molecule was introduced lo the molecular chains of naphthalene -benzaldehyde two components pitch resin. The structure of the pitch resin obtained was characterized by Fourier transform infrared spectnoscopy (VI - IR). The effects of synthesis conditions on the properties of the pitch resin such as softening point, coking value and bond strength were investigated by single factor experiments. Experimental results showed that the suitable technology conditions of synthesizing the naphthalene-naphthol-benzaldehyde pilch resin were: the amount of subatance ratio of naphthalene, naphthol and benzaldehyde 0.67*0.33:1, the reaction temperature 160 ℃, the reaction time 300 min and the usage of catalyst 10%. Under the optimal conditions, the pitch resin exhibits the softening point of 87,5 ℃, coking value of 32.1% and the bond strength of 41.1. The naphthalene - naphthol - benzaldehyde three components pilch resin with different bond properties can be obtained by controlling the substance amount of naphthol in reaction system.%在浓硫酸的催化作用下,采用阳离子聚合法在萘-苯甲醛二元组分沥青树脂分子链上引入了萘酚分子,合成了萘-萘酚-苯甲醛三元组分沥青树脂.用FT-IR光谱仪表征了合成树脂的结构.通过单因素实验,考察了合成条件对沥青树脂软化点、结焦值和黏结强度等黏结性能的影响规律.实验结果表明,合成萘-萘酚-苯甲醛沥青树脂适宜的工艺条件:萘、萘酚和苯甲醛的物质的量比为0.67:0.33:1,反应温度为160℃,反应时间为300 min,催化剂用量为10%.在此条件下,合成沥青树脂的软化点为87.5℃,结焦值为32.1%,黏结强度为41.1.改变反应体系中萘酚的物质的量,能获得具有不同黏结性能的萘-萘酚-苯甲醛三元组分沥青树脂.

  4. A closed concept of extractive whole cell microbial transformation of benzaldehyde into L-phenylacetylcarbinol by Saccharomyces cerevisiae in novel polyethylene-glycol-induced cloud-point system.

    Science.gov (United States)

    Wang, Zhilong; Liang, Rui; Xu, Jian-He; Liu, Yubo; Qi, Hanshi

    2010-03-01

    Extractive microbial transformation of benzaldehyde into L-phenylacetylcarbinol (L-PAC) by Saccharomyces cerevisiae (Baker's yeast) has been carried out in a novel polyethylene-glycol-induced cloud-point system (PEG-CPS). The extractive microbial transformation in the PEG-CPS and a downstream process for stripping of the product from the microbial transformation broth with microemulsion extraction are demonstrated. The results indicate that the PEG-CPS maintains the advantage of CPS for in situ extraction of polar product in the microbial transformation. At the same time, the utilization of hydrophilic nonionic surfactant in the PEG-CPS is favorable for stripping of product from the nonionic surfactant in the microbial transformation broth by Winsor I microemulsion extraction. Thus, a closed concept of in situ extraction of polar product in microbial transformation and its downstream process of product recovery are fulfilled at the same time.

  5. MCM-41 supported 12-tungstophosphoric acid mesoporous materials: Preparation, characterization, and catalytic activities for benzaldehyde oxidation with H2O2

    Science.gov (United States)

    Chen, Ya; Zhang, Xiao-Li; Chen, Xi; Dong, Bei-Bei; Zheng, Xiu-Cheng

    2013-10-01

    Mesoporous molecular sieves MCM-41 and bulk 12-tungstophosphoric acid (HPW) were synthesized and employed to prepare 5-45 wt.% HPW/MCM-41 mesoporous materials. Characterization results suggested the good dispersion of HPW within MCM-41 when the loading of HPW was less than 35 wt.% and HPW/MCM-41 retained the typical mesopore structure of the supports. The results of the catalytic oxidation of benzaldehyde to benzoic acid with 30% H2O2, in the absence of any organic solvent and co-catalysts, indicated that HPW/MCM-41 was an efficient catalyst and 30 wt.% HPW/MCM-41 sample exhibited the highest catalytic activity among these materials.

  6. A Helical Polyphenylacetylene Having Amino Alcohol Moieties Without Chiral Side Groups as a Chiral Ligand for the Asymmetric Addition of Diethylzinc to Benzaldehyde.

    Science.gov (United States)

    Liu, Lijia; Long, Qing; Aoki, Toshiki; Zhang, Geng; Kaneko, Takashi; Teraguchi, Masahiro; Zhang, Chunhong; Wang, Yudan

    2015-08-01

    One-handed helical polyphenylacetylenes having achiral amino alcohol moieties, but no chiral side groups, were synthesized by the helix-sense-selective copolymerization of an achiral phenylacetylene having an amino alcohol side group with a phenylacetylene having two hydroxyl groups. Since the resulting helical copolymers were successfully utilized as chiral ligands for the enantioselective alkylation of benzaldehyde with diethylzinc, we can conclude that the main-chain chirality based on the one-handed helical conformation is useful for the chiral catalysis of an asymmetric reaction for the first time. The enantioselectivities of the reaction were controlled by the optical purities of the helical polymer ligands. In addition, the polymer ligands could be easily recovered by precipitation after the reaction.

  7. High efficient photocatalytic selective oxidation of benzyl alcohol to benzaldehyde by solvothermal-synthesized ZnIn{sub 2}S{sub 4} microspheres under visible light irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Chen, Zhixin, E-mail: czx@fzu.edu.cn [State Key Laboratory Breeding Base of Photocatalysis, College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002 (China); Instrumental Measurement and Analysis Center, Fuzhou University, Fuzhou 350002 (China); Xu, Jingjing; Ren, Zhuyun [State Key Laboratory Breeding Base of Photocatalysis, College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002 (China); He, Yunhui; Xiao, Guangcan [State Key Laboratory Breeding Base of Photocatalysis, College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002 (China); Instrumental Measurement and Analysis Center, Fuzhou University, Fuzhou 350002 (China)

    2013-09-15

    Hexagonal ZnIn{sub 2}S{sub 4} samples have been synthesized by a solvothermal method. Their properties have been determined by X-ray diffraction, ultraviolet–visible-light diffuse reflectance spectra, field emission scanning electron microscopy, nitrogen adsorption–desorption and X-ray photoelectron spectra. These results demonstrate that ethanol solvent has significant influence on the morphology, optical and electronic nature for such marigold-like ZnIn{sub 2}S{sub 4} microspheres. The visible light photocatalytic activities of the ZnIn{sub 2}S{sub 4} have been evaluated by selective oxidation of benzyl alcohol to benzaldehyde using molecular oxygen as oxidant. The results show that 100% conversion along with >99% selectivity are reached over ZnIn{sub 2}S{sub 4} prepared in ethanol solvent under visible light irradiation (λ>420 nm) of 2 h, but only 58% conversion and 57% yield are reached over ZnIn{sub 2}S{sub 4} prepared in aqueous solvent. A possible mechanism of the high photocatalytic activity for selective oxidation of benzyl alcohol over ZnIn{sub 2}S{sub 4} is proposed and discussed. - Graphical abstract: Marigold-like ZnIn{sub 2}S{sub 4} microspheres were synthesized by a solvothermal method. The high visible photocatalytic activities of ZnIn{sub 2}S{sub 4} were evaluated by selective oxidation of benzyl alcohol to benzaldehyde under mild conditions. Display Omitted - Highlights: • Marigold-like ZnIn{sub 2}S{sub 4} microspheres were synthesized by a solvothermal method. • The solvents have a remarkably influence on the morphology and properties of samples. • It is the first time to apply ZnIn{sub 2}S{sub 4} for selective oxidation of benzyl alcohol. • ZnIn{sub 2}S{sub 4} shows high photocatalytic activity for selective oxidation of benzyl alcohol.

  8. Structural, spectral, electrochemistry, thermal properties and theoretical studies on 4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone

    Science.gov (United States)

    Lizeng, Liu; Wei, Li; Xianfang, Meng; Dongzhi, Liu; Gongfeng, Xu; Zhengchen, Bai

    2014-11-01

    The title compound 4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone (C28H24ClN3O, Mr = 453.96) was synthesized by the reaction of 4-[N, N-di(4-tolyl)amino] benzaldehyde with 2-chlorobenzohydrazide, and its structure was characterized by IR, 1H NMR, 13H NMR, high-resolution mass spectrometry and single-crystal X-ray diffraction. The crystal belongs to Monoclinic, space group P2(1)/n with a = 12.626(3), b = 12.609(3), c = 15.837(3) Å, β = 90.00(3)°, Z = 5, V = 2512.5(9) Å3, Mr = 453.95, Dc = 1.280 g/cm3, μ = 0.183 mm-1, F(0 0 0) = 1024, R = 0.0432 and wR = 0.1087. X-ray analysis revealed that one of the benzene ring and acylhydrazone were essentially planar, the 2-chloro benzene ring and amide were non-planar, the torsion angles C(1)sbnd C(6)sbnd C(7)sbnd O(1) and C(5)sbnd C(6)sbnd C(7)sbnd O(1) are 61.4(5)° and -114.4(4)°. The thermal stability studies indicate that the title compound is stable up to 341.1 °C. The spectral, electrochemistry properties and theoretical studies show that the title compound is a good candidate for the charge-transporting materials.

  9. Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides.

    Science.gov (United States)

    Čobeljić, Božidar; Milenković, Milica; Pevec, Andrej; Turel, Iztok; Vujčić, Miroslava; Janović, Barbara; Gligorijević, Nevenka; Sladić, Dušan; Radulović, Siniša; Jovanović, Katarina; Anđelković, Katarina

    2016-04-01

    Square-planar azido Ni(II) complex with condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent was synthesized and its crystal structure was determined. Cytotoxic activity of the azido complex and previously synthesized isothiocyanato, cyanato and chlorido Ni(II) complexes with this ligand was examined on six tumor cell lines (HeLa, A549, K562, MDA-MB-453, MDA-MB-361 and LS-174) and two normal cell line (MRC-5 and BEAS-2B). All the investigated nickel(II) complexes were cytotoxic against all tumor cell lines. The newly synthesized azido complex showed selectivity to HeLa and A549 tumor cell lines compared to the normal cells (for A549 IC50 was similar to that of cisplatin). Azido complex interferes with cell cycle phase distribution of A549 and HeLa cells and possesses nuclease activity towards supercoiled DNA. The observed selectivity of the azido complex for some tumor cell lines can be connected with its strong DNA damaging activity.

  10. Crystal Structures of Two Calix[4]arene Isomers with Benzaldehyde Moiety and Their Photophysical Properties with Terbium(Ⅲ) Ions

    Institute of Scientific and Technical Information of China (English)

    王浩; 张衡益; 刘育

    2005-01-01

    Two calix[4]arene isomers with benzaldehyde moieties, i.e., 5,11,17,23-tetra-tert-butyl-25,27-bis[2-(o-formyl-phenoxy)ethoxy]-26,28-dihydroxycalix[4]arene (3) and 5,11,17,23-tetra-tert-butyl-25,27-bis[2-(p-formylphenoxy)-ethoxy]-26,28-dihydroxycalix[4]arene (4), were synthesized according to a newly designed route in high yields, and their crystal structures have been determined by X-ray crystallographic study. The photophysical behavior on complexation of calix[4]arene derivatives 3 and 4 with terbium(Ⅲ) nitrate was investigated in anhydrous acetonitrile at 25℃ by UV-Vis and fluorescence spectroscopies. The crystallographic structure of 3 indicated that the eight oxygen atoms formed a preorganized ionophoric cavity due to intramolecular π-π stacking, which could encapsulate lanthanide ions tightly. In sharp contrast, the compound 4 formed a linear array by intermolecular π-π stacking, hence the oxygen atoms of pendant arms could not coordinate with metal ions, giving a poor binding ability to Tb3+. The absorption spectra of 3 with Tb3+ showed clearly a new broad intense absorption at 385nm. Interestingly, the narrow emission line spectrum has also been observed for compound 3 with Tb3+, and the results obtained were discussed from the viewpoint of energy transfer mechanism between host structures and the properties of lanthanide ions.

  11. Ab-initio and DFT calculations on molecular structure, NBO, HOMO-LUMO study and a new vibrational analysis of 4-(Dimethylamino) Benzaldehyde.

    Science.gov (United States)

    Rocha, Mariana; Di Santo, Alejandro; Arias, Juan Marcelo; Gil, Diego M; Ben Altabef, Aída

    2015-02-05

    The experimental and theoretical study on the molecular structure and a new vibrational analysis of 4-(Dimethylamino) Benzaldehyde (DMABA) is presented. The IR and Raman spectra were recorded in solid state. Optimized geometry, vibrational frequencies and various thermodynamic parameters of the title compound were calculated using DFT methods and are in agreement with the experimental values. A detailed interpretation of the IR and Raman spectra of the title compound were reported. The stability of the molecule arising from hyper-conjugative interactions and charge delocalization has been analyzed using NBO analysis and AIM approach. The HOMO and LUMO analysis were used to determine the charge transfer within the molecule and some molecular properties such as ionization potential, electron affinity, electronegativity, chemical potential, hardness, softness and global electrophilicity index. The TD-DFT approach was applied to assign the electronic transitions observed in the UV-visible spectrum measured experimentally. Molecular electrostatic potential map was performed by the DFT method. According to DSC measurements, the substance presents a melting point of 72.34°C and decomposes at temperatures higher than 193°C.

  12. High efficient photocatalytic selective oxidation of benzyl alcohol to benzaldehyde by solvothermal-synthesized ZnIn2S4 microspheres under visible light irradiation

    Science.gov (United States)

    Chen, Zhixin; Xu, Jingjing; Ren, Zhuyun; He, Yunhui; Xiao, Guangcan

    2013-09-01

    Hexagonal ZnIn2S4 samples have been synthesized by a solvothermal method. Their properties have been determined by X-ray diffraction, ultraviolet-visible-light diffuse reflectance spectra, field emission scanning electron microscopy, nitrogen adsorption-desorption and X-ray photoelectron spectra. These results demonstrate that ethanol solvent has significant influence on the morphology, optical and electronic nature for such marigold-like ZnIn2S4 microspheres. The visible light photocatalytic activities of the ZnIn2S4 have been evaluated by selective oxidation of benzyl alcohol to benzaldehyde using molecular oxygen as oxidant. The results show that 100% conversion along with >99% selectivity are reached over ZnIn2S4 prepared in ethanol solvent under visible light irradiation (λ>420 nm) of 2 h, but only 58% conversion and 57% yield are reached over ZnIn2S4 prepared in aqueous solvent. A possible mechanism of the high photocatalytic activity for selective oxidation of benzyl alcohol over ZnIn2S4 is proposed and discussed.

  13. Ab-initio and DFT calculations on molecular structure, NBO, HOMO-LUMO study and a new vibrational analysis of 4-(Dimethylamino) Benzaldehyde

    Science.gov (United States)

    Rocha, Mariana; Di Santo, Alejandro; Arias, Juan Marcelo; Gil, Diego M.; Altabef, Aída Ben

    2015-02-01

    The experimental and theoretical study on the molecular structure and a new vibrational analysis of 4-(Dimethylamino) Benzaldehyde (DMABA) is presented. The IR and Raman spectra were recorded in solid state. Optimized geometry, vibrational frequencies and various thermodynamic parameters of the title compound were calculated using DFT methods and are in agreement with the experimental values. A detailed interpretation of the IR and Raman spectra of the title compound were reported. The stability of the molecule arising from hyper-conjugative interactions and charge delocalization has been analyzed using NBO analysis and AIM approach. The HOMO and LUMO analysis were used to determine the charge transfer within the molecule and some molecular properties such as ionization potential, electron affinity, electronegativity, chemical potential, hardness, softness and global electrophilicity index. The TD-DFT approach was applied to assign the electronic transitions observed in the UV-visible spectrum measured experimentally. Molecular electrostatic potential map was performed by the DFT method. According to DSC measurements, the substance presents a melting point of 72.34 °C and decomposes at temperatures higher than 193 °C.

  14. Synthesis, spectroscopic investigations and computational study of 4-((9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy)benzaldehyde

    Science.gov (United States)

    Kanaani, A.; Ajloo, D.; Kiyani, H.; Farahani, M.

    2014-04-01

    The molecular structure, vibrational frequencies, corresponding vibrational assignments of 4-((9,10-dioxo-9,10-dihydroanthracen-1-yl)oxy)benzaldehyde in “trans” and “ana” forms have been investigated by UV-Vis, FT-IR and NMR spectroscopy as well as density functional theory (DFT) B3LYP method with 6-311++G(d,p) basis set. The vibrational analysis of the two forms of cited compound was performed by means of infrared absorption spectroscopy in combination with theoretical simulations. The obtained geometrical parameters and wavenumbers of vibrational normal modes from the DFT method were in good consistency with the experimental values. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by GIAO method. Computed molecular orbital and time dependent DFT oscillator renderings agree closely with experimental observations. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. In order to predict the reactive sites, a molecular electrostatic potential map (MEP) for the title compound was obtained. Transition structures were calculated by QST3 and IRC methods which yielded the potential energy surface and activation energy.

  15. 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: rational identification of a new anticancer lead.

    Science.gov (United States)

    Dutta Gupta, Sayan; Revathi, B; Mazaira, Gisela I; Galigniana, Mario D; Subrahmanyam, C V S; Gowrishankar, N L; Raghavendra, N M

    2015-04-01

    Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, (1)H NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents.

  16. 苯甲醛在光催化反应中氧化还原选择性的理论研究%Theoretical Study on the Selective Redox Mechanism of Benzaldehyde in Photo-catalyzed Reaction†

    Institute of Scientific and Technical Information of China (English)

    黄晓; 甘汉麟; 彭亮; 顾凤龙

    2016-01-01

    采用密度泛函理论方法在 M06-2X/6-311G*水平上模拟了不同反应条件下, TiO2对苯甲醛的光催化还原和氧化的反应。计算结果表明,苯甲醛的光催化还原和氧化反应均可在常温下发生;在缺氧但有乙醇存在的条件下,乙醇分子可与氧化性物质发生反应,生成醇自由基,苯甲醛主要发生光催化还原反应生成苯甲醇;在有氧气但无乙醇存在条件下,还原性的光生电子被氧气捕获,避免了苯甲醛被还原,主要发生光催化氧化反应生成苯甲酸。%The photoelectron and photohole could be generated on the surface of TiO2 under the UV irradiation. Some reactive species could be produced indirectly. The photoelectron could be trapped by oxygen leading to yield the superoxide anion radicals, while the photohole can react with the solvent molecules to generate the hydroxyl radical and alcohol radical. The substrate may be reduced by the photoelectron directly, or by alcohol radicals. And it may be oxidized by the photohole directly, or by the reactive species of hydroxyl radicals and superoxide anion radicals. The M06-2X/ 6-311G* method was employed to investigate the selective redox mechanism of benzaldehyde in solution, which was reduced or oxidized by the reactive species generated during the photo-catalyzed process in different reaction conditions. According to the computation results, the photo-redox reaction of benzaldehyde would be happened in room temperature. In oxygen-free ethanol solvent, the ethanol molecules could react with the oxidizing species to yield the alcohol radicals, while benzaldehyde could be mainly reduced to benzyl alcohol. In oxygen-rich without ethanol condition, the reductive photoelectron is trapped by oxygen to prohibit the reduction of benzaldehyde, so benzaldehyde is mainly oxidized to benzoic acid.

  17. Co-ETS-10 and Co-AM-6 as active catalysts for the oxidation of styrene to styrene oxide and benzaldehyde using molecular oxygen

    Institute of Scientific and Technical Information of China (English)

    Shuvo Jit Datta; Kyung Byung Yoon

    2015-01-01

    Pristine ETS-10 and AM-6 and their Co2+-exchanged forms were prepared, and their catalytic activi-ties toward the oxidation of styrene in oxygen atmosphere were studied in dimethylformamide. The catalysts were denoted as Co-E10-n (n=0, 9, 26, 68, 81) and Co-A6-m (m=0, 8, 23, 63, 79), where n and m denote the degree of Co2+exchange. The products of the oxidation process were identified as styrene epoxide (E) and benzaldehyde (B). Both the pristine forms, ETS-10 (Co-E10-0) and AM-6 (Co-A6-0), and Co2+-exchanged forms displayed catalytic activities. With increasing n or m, the con-version, and hence the rate, increased. Specifically, the rates varied from 6.1 to 12.5 mmol·g−1·h−1 with increasing n (Co-E10-n catalysts) and from 5.4 to 12.4 mmol·g−1·h−1 with increasing m (Co-A6-m catalysts). In contrast, the E/B ratio decreased with increasing n or m. More specifically, the E/B ratio decreased from 2.1 to 0.1 with increasing n from 0 to 81 (Co-E10-n catalysts) and from 1.3 to 0.1 with increasing m from 0 to 79 (Co-A6-m catalysts). Co-E10-9 displayed the highest E yield and Co-A6-79 generated the highest B yield. The highest turnover frequency obtained was 36.3 Co−1·h−1, which was the highest one obtained among those obtained for the Co2+-exchanged zeolites and mesoporous silica reference materials studied in this work.

  18. Core-Shell Structural CdS@SnO₂ Nanorods with Excellent Visible-Light Photocatalytic Activity for the Selective Oxidation of Benzyl Alcohol to Benzaldehyde.

    Science.gov (United States)

    Liu, Ya; Zhang, Ping; Tian, Baozhu; Zhang, Jinlong

    2015-07-01

    Core-shell structural CdS@SnO2 nanorods (NRs) were fabricated by synthesizing SnO2 nanoparticles with a solvent-assisted interfacial reaction and further anchoring them on the surface of CdS NRs under ultrasonic stirring. The morphology, composition, and microstructures of the obtained samples were characterized by field-emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, X-ray photoelectron spectroscopy, and nitrogen adsorption-desorption. It was found that SnO2 nanoparticles can be tightly anchored on the surface of CdS NRs, and the thickness of SnO2 shells can be conveniently adjusted by simply changing the addition amount of SnO2 quantum dots. UV-vis diffuse reflectance spectrum indicated that SnO2 shell layer also can enhance the visible light absorption of CdS NRs to a certain extent. The results of transient photocurrents and photoluminescence spectra revealed that the core-shell structure can effectively promote the separation rate of electron-hole pairs and prolong the lifetime of electrons. Compared with the single CdS NRs, the core-shell structural CdS@SnO2 exhibited a remarkably enhanced photocatalytic activity for selective oxidation of benzyl alcohol (BA) to benzaldehyde (BAD) under visible light irradiation, attributed to the more efficient separation of electrons and holes, improved surface area, and enhanced visible light absorption of core-shell structure. The radical scavenging experiments proved that in acetonitrile solution, ·O2- and holes are the main reactive species responsible for BA to BAD transformation, and the lack of ·OH radicals is favorable to obtaining high reaction selectivity.

  19. Effects of the aldehyde dehydrogenase inhibitor disulfiram on the plasma pharmacokinetics, metabolism, and toxicity of benzaldehyde dimethane sulfonate (NSC281612, DMS612, BEN) in mice

    Science.gov (United States)

    Parise, Robert A.; Beumer, Jan H.; Clausen, Dana M.; Rigatti, Lora H.; Ziegler, Judy A.; Gasparetto, Maura; Smith, Clayton A; Eiseman, Julie L.

    2013-01-01

    Purpose Benzaldehyde dimethane sulfonate (DMS612, NSC281612, BEN) is an alkylator with activity against renal cell carcinoma, currently in phase I trials. In blood, BEN is rapidly metabolized into its highly reactive carboxylic acid (BA), presumably the predominant alkylating species. We hypothesized that BEN is metabolized to BA by aldehyde dehydrogenase (ALDH) and aimed to increase BEN exposure in blood and tissues by inhibiting ALDH with disulfiram thereby shifting BA production from blood to tissues. Methods Female CD2F1 mice were dosed with 20 mg/kg BEN iv alone or 24 h after 300 mg/kg disulfiram ip. BEN, BA and metabolites were quantitated in plasma and urine, and toxicities were assessed. Results BEN had a plasma t½ <5 min and produced at least 12 products. The metabolite half-lives were <136 min. Disulfiram increased BEN plasma exposure 368-fold, (AUC0-inf from 0.11 to 40.5 mg/L•min), while plasma levels of BA remained similar. Urinary BEN excretion increased (1.0% to 1.5% of dose) while BA excretion was unchanged. Hematocrit, white blood cells counts and %lymphocytes decreased after BEN administration. Co-administration of disulfiram appeared to enhance these effects. Profound liver pathology was observed in mice treated with disulfiram and BEN. Conclusions BEN plasma concentrations increased after administration of disulfiram, suggesting that ALDH mediates the rapid metabolism of BEN in vivo, which may explain the increased toxicity seen with BEN after administration of disulfiram. Our results suggest that the co-administration of BEN with drugs that inhibit ALDH or to patients that are ALDH deficient may cause liver damage. PMID:24061865

  20. Application of the extended real associated solution (ERAS) theory to excess molar enthalpies of benzaldehyde + 1-alkanols (C{sub 1} to C{sub 5}) at T = 298.15 K

    Energy Technology Data Exchange (ETDEWEB)

    Iloukhani, H., E-mail: iloukhani@basu.ac.ir [Department of Physical Chemistry, Faculty of Chemistry, University of Bu-Ali Sina, Hamedan 65174 (Iran, Islamic Republic of); Fattahi, M. [Department of Physical Chemistry, Faculty of Chemistry, University of Bu-Ali Sina, Hamedan 65174 (Iran, Islamic Republic of)

    2011-11-15

    Highlights: > Enthalpy of binary mixtures of {l_brace}benzaldehyde + 1-alkanols{r_brace} (C{sub 1} to C{sub 5}) determined. > Excess molar enthalpy, partial molar enthalpy, and intermolecular interaction functions were calculated. > Excess molar enthalpy was correlated as a function of mole fraction by using the Redlich-Kister equation. > The experimental results have been used to test the applicability of the ERAS-model, Wilson and NRTL equations. - Abstract: This paper reports excess molar enthalpies, H{sub m}{sup E}, for the binary mixtures of {l_brace}1-alkanols (2), namely, {l_brace}methanol, ethanol, 1-propanol, 1-butanol, and 1-pentanol{r_brace} with benzaldehyde (1){r_brace} at T = 298.15 K at ambient pressure over a whole range of mole fraction. The sign of H{sub m}{sup E} for all systems are positive and the magnitude of H{sub m}{sup E} values with increasing of chain length, increase. The Redlich-Kister polynomial equation was used to correlate H{sub m}{sup E}. The excess partial molar enthalpies of benzaldehyde, H{sub m,1}{sup E}, excess partial molar enthalpies of 1-alkanols (C{sub 1} to C{sub 5}), H{sub m,2}{sup E}, and excess partial molar enthalpies at infinite dilution, H{sub m,i}{sup E,0}, are calculated according to experimental excess molar enthalpies and Redlich-Kister polynomial equation. The extracted date were used to evaluated the so-called intermolecular interaction functions {partial_derivative}H{sub m,i}{sup E}/{partial_derivative}x{sub i} and {partial_derivative}H{sub m,i}{sup E}/{partial_derivative}x{sub j} in terms of enthalpy. The ERAS, Wilson and NRTL models have been applied for describing the H{sub m}{sup E}.

  1. Comparative study of Palladium (II using 4-Hydroxy 3, 5 dimethoxy benzaldehyde 4-hydroxy benzoyl hydrazone and Cinnamaldehyde 4-hydroxy benzoylhydrazone in presence of micellar medium by Spectrophotometry

    Directory of Open Access Journals (Sweden)

    D.Gopala Krishna,

    2010-09-01

    Full Text Available Two simple, sensitive, rapid and selective spectrophotometric methods have been developed for the determination of Palladium (II using newly synthesized reagents 4-Hdroxy3,5dimethoxy benzaldehyde-4-hydroxybenzoylhydrazone (HDMBHBH and Cinnamaldehyde 4-hydroxy benzoylhydrazone (CMHBH in presence of neutral surfactant TritonX-100-5% (micellar medium. Palladium (II forms a brown coluored water-soluble complex with HDMBHBH and CMHBH-in the pH range 1.0-6.0. The Pd (II-HDMBHBH complex shows maximum absorbance at max 373 nm in the pH range 3.0-4.0 and Pd (II-CMHBH shows at max 375 nm in thepH range 4.0-5.0. At these wavelengths (max, the complex shows maximum absorbance while the reagent blanks shows negligible absorbance. Hence, analytical studies were carried out at max 373 nm at pH 3.0 for HDMBHBH and 375 nm at pH 4.0 for CMHBH against reagent blanks. Beer's law is obeyed in the range 0.106-1.064 μg ml-1 and the optimum concentration range from ringbom plot is 0.212-0.957 g/ml of Palladium (II for both reagents. The molar absorptivity and Sandell's sensitivity for the coloured solution were found to be 7.5 x 104 L mol-1 cm-1 and 0.0015-μg. cm-2 for HDMBHBH, 6.0x104L mol-1 cm-1 , and 0.0017 -μg. cm-2 for CMHBH respectively. The interference effects of various diverse ions have been studied. Palladium (II forms 1:1 complex with HDMBHBH and CMHBH stoichiometry with stability constant 7.29 x 106 for HDMBHBH and 3.55 x 106 for CMHBH. The standard deviation in the determination of 0.638-μg ml-1 of Palladium (II is 0.003 for HDMBHBH and 0.008 for CMHBH. The Relative standard deviation is 0.71% for HDMBHBH and 2.5% for CMHBH. First and second order derivative spectroscopic methods were developed at max 422 nm and 444 nm for HDMBHBH and at 402 nm and438 nm for CMHBH respectively, for the determination of Palladium (II, which is more sensitive than the zero order method. The developed method has been employed for the determination of

  2. Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione.

    Science.gov (United States)

    Singh, Ajay K; Pandey, O P; Sengupta, S K

    2013-09-01

    Zn(II) complexes have been synthesized by reacting zinc acetate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/benzaldehyde/indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non electrolytes. Elemental analyses suggest that the complexes have 1:2 metal to ligands stoichiometry of the types [ZnL2(H2O)2](L=monoanionic Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/indoline-2,3-dione) [ZnL2(')(OOCCH3)2(H2O)2](L'=neutral Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde), and they were characterized by IR, (1)H NMR, and (13)C NMR. Particle sizes of synthesized compounds were measured with dynamic light scattering (DLS) analyser which indicates that particle diameter are of the range ca. 100-200nm. All these Schiff bases and their complexes have also been screened for their antibacterial (Bacillus subtilis (B. subtilis), Escherichia coli (E. coli) and antifungal activities (Colletotrichum falcatum (C. falcatum), Aspergillus niger (A. niger), Fusarium oxysporium (F. oxysporium) Curvularia pallescence (C. pallescence). The antimicrobial activities have shown that upon complexation the activity increases.

  3. Ozone reaction with n-aldehydes (n=4-10), benzaldehyde, ethanol, isopropanol, and n-propanol adsorbed on a dual-bed graphitized carbon-carbon molecular sieve adsorbent cartridge.

    Science.gov (United States)

    McClenny, W A; Colón, M; Oliver, K D

    2001-09-21

    Ozone reacts with n-aldehydes (n=4-10), benzaldehyde, ethanol, isopropanol and n-propanol adsorbed on a dual-bed graphitized carbon-carbon molecular sieve adsorbent cartridge. Destruction of n-aldehydes increases with n number and with ozone concentration. In some sampling experiments both generation and destruction of n-aldehydes by ozone are observed. In field experiments the results of sample analysis for n-aldehydes and benzaldehyde are frequently not proportional to sample volume whereas results for toluene and isoprene, and sometimes for total carbon, are. A simple theory is developed to simulate the net result of three processes: the adsorption of compounds from an air stream onto a solid adsorbent, the generation of compounds by reaction of ozone with materials upstream of or on the adsorbent, and the destruction by ozone of pre-existing compounds and compounds adsorbed from the sample stream. The use of distributed volume pairs is recommended as a way to identify loss of sample integrity during air monitoring experiments.

  4. Determination of human serum semicarbazide-sensitive amine oxidase activity via flow injection analysis with fluorescence detection after online derivatization of the enzymatically produced benzaldehyde with 1,2-diaminoanthraquinone.

    Science.gov (United States)

    El-Maghrabey, Mahmoud H; Kishikawa, Naoya; Ohyama, Kaname; Imazato, Takahiro; Ueki, Yukitaka; Kuroda, Naotaka

    2015-06-30

    A fast, simple, and sensitive flow injection analysis method was developed for the measurement of semicarbazide-sensitive amine oxidase (SSAO) activity in human serum. Benzaldehyde, generated by the action of SSAO after incubation of serum with benzylamine, was derivatized with a novel aromatic aldehyde-specific reagent (1,2-diaminoanthraquinone) and the fluorescent product was measured by fluorescence detection at excitation and emission wavelengths of 390 and 570nm, respectively. Serum SSAO activity was defined as benzaldehyde (nmol) formed per milliliter serum per hour. The method was linear over SSAO activity of 0.2-150.0nmolmL(-1)h(-1) with a detection limit of 0.06nmolmL(-1)h(-1). The %RSD of intra-day and inter-day precision did not exceed 9.4% and the accuracy ranged from -6.5 to -0.6%. The method was applied for the determination of the serum SSAO activity in healthy controls (C, n=24) and diabetes mellitus patients (DM, n=18). It was demonstrated that the activity (mean±SE) of SSAO in diabetics sera was significantly higher than that in healthy subjects' ones (DM; 73.3±1.8nmolmL(-1)h(-1)vs C; 58.9±2.2nmolmL(-1)h(-1), P<0.01).

  5. Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione

    Science.gov (United States)

    Singh, Ajay K.; Pandey, O. P.; Sengupta, S. K.

    2013-09-01

    Zn(II) complexes have been synthesized by reacting zinc acetate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/benzaldehyde/indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non electrolytes. Elemental analyses suggest that the complexes have 1:2 metal to ligands stoichiometry of the types [ZnL2(H2O)2](L = monoanionic Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/indoline-2,3-dione) [ZnL2‧(OOCCH3)2(H2O)2](L‧ = neutral Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde), and they were characterized by IR, 1H NMR, and 13C NMR. Particle sizes of synthesized compounds were measured with dynamic light scattering (DLS) analyser which indicates that particle diameter are of the range ca. 100-200 nm. All these Schiff bases and their complexes have also been screened for their antibacterial (Bacillus subtilis (B. subtilis), Escherichia coli (E. coli) and antifungal activities (Colletotrichum falcatum (C. falcatum), Aspergillus niger (A. niger), Fusarium oxysporium (F. oxysporium) Curvularia pallescence (C. pallescence). The antimicrobial activities have shown that upon complexation the activity increases.

  6. The DFT study on the reaction between benzaldehyde and 4-amine-4H-1,2,4-triazole and their derivatives as a source of stable hemiaminals and Schiff bases. Effect of substitution and solvation on the reaction mechanism.

    Science.gov (United States)

    Berski, Slawomir; Gordon, Agnieszka J; Ciunik, Leszek Zbigniew

    2015-03-01

    Reaction mechanism for the benzaldehyde (ald) and 4-amine-4H-1,2,4-triazole (4at) has been investigated at the DFT (B3LYP)/6-31+G(d) computational level. Three transition states (TS) have been identified. The TS1 corresponds to hydrogen transfer from the NH2 group to the C = O bond and nucleophillic attack of the carbon atom from the aldehyde group on the nitrogen atom from the NH2 group in 4at. The result of this reaction is the hemiaminal molecule. The TS2 characterises an internal rearrangement of the benzene and triazole rings in the hemiaminal molecule. The TS3 leads to breaking of the O-H bond, the elimination reaction of the H2O molecule, and formation of the C=N bond. The final product of this reaction is a Schiff base. In order to determine the most favorable conditions for hemiaminal formation, the influence of electronic structure modification on the energetic properties during the reaction of benzaldehyde and 4-amine-4H-1,2,4-triazole has been studied. Thirteen substituents: NH2, OH, OCH3, CH3, F, I, Cl, Br, COH, COOH, CF3, CN, NO2, with different Hammett's constant values (σ = -0.66-+0.78) have been considered. Finally, the reaction mechanism has been investigated in the presence of 1 to 5 water molecules.

  7. Computational studies of ion pairing. 8. Ion pairing of tetraalkylammonium ions to nitrosobenzene and benzaldehyde redox species. A general binding motif for the interaction of tetraalkylammonium ions with benzenoid species.

    Science.gov (United States)

    Fry, Albert J

    2013-06-01

    Very little data is available on the detailed structures of ion pairs in solution, since few general experimental methods are available for obtaining such information. For this reason, computational methods have emerged as the method of choice for determining the structures of organic ion pairs in solution. The present study examines the ion pairs between a series of tetraalkylammonium ions and several redox forms of nitrosobenzene and a series of substituted benzaldehydes. The structures, though previously unexpected, are chemically reasonable and fit into a previous pattern of ion pairing described in previous publications in this series. To date in these studies, a total of 73 ion pairs and related species have in fact been identified having exactly the same unusual orientation of the tetraalkylammonium component with respect to the donor species. The results are pertinent to topics of general current interest, including self-assembly, molecular recognition, and supramolecular assembly.

  8. 对甲基苯甲醛改性煤沥青的改性机理研究%STUDY ON MODIFITION MECHANISM OF THE MODIFIED COAL TAR PITCH WITH 4-METHYL BENZALDEHYDE

    Institute of Scientific and Technical Information of China (English)

    宋士华; 魏健宁; 马明亮

    2007-01-01

    以对甲基苯甲醛(4-methyl benzaldehyde,简称4-MB)为改性剂,在对甲苯磺酸(PTS)的作用下对煤沥青(Coal Tar Pitch)进行了改性研究.采用傅立叶红外光谱(FT-IR)和核磁共振氢谱(1H-NMR)对煤沥青改性机理进行分析;采用扫描电镜(SEM)观察改性后煤沥青的形貌;采用光学显微镜观察改性沥青热解产物的光学结构.实验结果表明,对甲基苯甲醛在酸性催化剂的催化作用下与煤沥青发生亲电取代反应.

  9. Corrosion inhibition of 6061 Al-15 vol. pct. SiC(p) composite and its base alloy in a mixture of sulphuric acid and hydrochloric acid by 4-(N,N-dimethyl amino) benzaldehyde thiosemicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Pinto, Geetha Mable [Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasnagar 575 025, Mangalore, Karnataka (India); Nayak, Jagannath [Department of Metallurgical and Materials Engineering, National Institute of Technology Karnataka, Surathkal, Srinivasnagar 575 025, Karnataka (India); Shetty, A. Nityananda, E-mail: nityashreya@gmail.com [Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasnagar 575 025, Mangalore, Karnataka (India)

    2011-02-15

    Research highlights: {yields} Corrosion inhibition of Al-SiC composite. {yields} DMABT as corrosion inhibitor. {yields} Inhibition through physisorption of DMABT. - Abstract: The corrosion inhibition characteristics of 4-(N,N-dimethylamino) benzaldehyde thiosemicarbazone (DMABT) on the corrosion behavior of 6061 Al-15 vol. pct. SiC(p) composite and its base alloy were studied at different temperatures in acid mixture medium containing varying concentrations of hydrochloric acid and sulphuric acid using Tafel extrapolation technique and ac impedance spectroscopy (EIS). The effect of inhibitor concentration, temperature and concentration of the acid mixture media on the inhibitor action was investigated. It was found that inhibition efficiencies increase with the increase in inhibitor concentration, but decrease with the increase in temperature and with the increase in concentration of the acid media. Thermodynamic parameters for dissolution process were determined. The adsorption of DMABT on both the composite and base alloy was found to be through physisorption obeying Freundlich adsorption isotherm.

  10. Inhibitory Effects of Benzaldehyde Derivatives from the Marine Fungus Eurotium sp. SF-5989 on Inflammatory Mediators via the Induction of Heme Oxygenase-1 in Lipopolysaccharide-Stimulated RAW264.7 Macrophages

    Directory of Open Access Journals (Sweden)

    Kyoung-Su Kim

    2014-12-01

    Full Text Available Two benzaldehyde derivatives, flavoglaucin (1 and isotetrahydro-auroglaucin (2, were isolated from the marine fungus Eurotium sp. SF-5989 through bioassay- and 1H NMR-guided investigation. In this study, we evaluated the anti-inflammatory effects of these compounds in lipopolysaccharide (LPS-stimulated RAW264.7 macrophages. We demonstrated that compounds 1 and 2 markedly inhibited LPS-induced nitric oxide (NO and prostaglandin E2 (PGE2 production by suppressing inducible nitric oxide synthase (iNOS and cyclooxygenase-2 (COX-2 protein expression without affecting cell viability. We also demonstrated that the compounds reduced the secretion of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α, interleukin-1β (IL-1β and interleukin-6 (IL-6. Furthermore, compounds 1 and 2 inhibited LPS-induced nuclear factor-κB (NF-κB activation by suppressing phosphorylation of IkappaB (IκB. These results indicated that the anti-inflammatory effects of these benzaldehyde derivatives in LPS-stimulated RAW264.7 macrophages were due to the inactivation of the NF-κB pathway. In addition, compounds 1 and 2 induced heme oxygenase-1 (HO-1 expression through the nuclear transcription factor-E2–related factor 2 (Nrf2 translocation. The inhibitory effects of compounds 1 and 2 on the production of pro-inflammatory mediators and on NF-κB binding activity were reversed by HO-1 inhibitor tin protoporphyrin (SnPP. Thus, the anti-inflammatory effects of compounds 1 and 2 also correlated with their ability of inducing HO-1 expression.

  11. Inhibitory effects of benzaldehyde derivatives from the marine fungus Eurotium sp. SF-5989 on inflammatory mediators via the induction of heme oxygenase-1 in lipopolysaccharide-stimulated RAW264.7 macrophages.

    Science.gov (United States)

    Kim, Kyoung-Su; Cui, Xiang; Lee, Dong-Sung; Ko, Wonmin; Sohn, Jae Hak; Yim, Joung Han; An, Ren-Bo; Kim, Youn-Chul; Oh, Hyuncheol

    2014-12-19

    Two benzaldehyde derivatives, flavoglaucin (1) and isotetrahydro-auroglaucin (2), were isolated from the marine fungus Eurotium sp. SF-5989 through bioassay- and 1H NMR-guided investigation. In this study, we evaluated the anti-inflammatory effects of these compounds in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. We demonstrated that compounds 1 and 2 markedly inhibited LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production by suppressing inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expression without affecting cell viability. We also demonstrated that the compounds reduced the secretion of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β) and interleukin-6 (IL-6). Furthermore, compounds 1 and 2 inhibited LPS-induced nuclear factor-κB (NF-κB) activation by suppressing phosphorylation of IkappaB (IκB). These results indicated that the anti-inflammatory effects of these benzaldehyde derivatives in LPS-stimulated RAW264.7 macrophages were due to the inactivation of the NF-κB pathway. In addition, compounds 1 and 2 induced heme oxygenase-1 (HO-1) expression through the nuclear transcription factor-E2-related factor 2 (Nrf2) translocation. The inhibitory effects of compounds 1 and 2 on the production of pro-inflammatory mediators and on NF-κB binding activity were reversed by HO-1 inhibitor tin protoporphyrin (SnPP). Thus, the anti-inflammatory effects of compounds 1 and 2 also correlated with their ability of inducing HO-1 expression.

  12. The study of partial and excess molar volumes for binary mixtures of nitrobenzene and benzaldehyde with xylene isomers from T = (298.15 to 318.15 K and P = 0.087 MPa

    Directory of Open Access Journals (Sweden)

    Hamid R. Rafiee

    2016-09-01

    Full Text Available Based on density measurements, partial and excess molar volumes for binary mixtures of nitrobenzene and benzaldehyde with three isomers of xylene have been measured. The whole range of composition and temperatures from T = (298.15 to 318.15 K at ambient pressure 0.087 MPa, has been considered. The excess molar volumes were negative and decreased by increasing temperature for all mixtures which are explained based on intermolecular interactions. Excess molar volumes for solutions including nitrobenzene were absolutely larger than benzaldehyde binary mixtures. The partial and excess molar volumes for each component have been appraised and reported. The excess molar volumes have been successfully fitted to Redlich–Kister equation.

  13. Electronic and vibrational spectra of protonated benzaldehyde-water clusters, [BZ-(H2O)n≤5]H+: evidence for ground-state proton transfer to solvent for n ≥ 3.

    Science.gov (United States)

    Dopfer, Otto; Patzer, Alexander; Chakraborty, Shamik; Alata, Ivan; Omidyan, Reza; Broquier, Michel; Dedonder, Claude; Jouvet, Christophe

    2014-03-28

    Vibrational and electronic photodissociation spectra of mass-selected protonated benzaldehyde-(water)n clusters, [BZ-(H2O)n]H(+) with n ≤ 5, are analyzed by quantum chemical calculations to determine the protonation site in the ground electronic state (S0) and ππ(*) excited state (S1) as a function of microhydration. IR spectra of [BZ-(H2O)n]H(+) with n ≤ 2 are consistent with BZH(+)-(H2O)n type structures, in which the excess proton is localized on benzaldehyde. IR spectra of clusters with n ≥ 3 are assigned to structures, in which the excess proton is located on the (H2O)n solvent moiety, BZ-(H2O)nH(+). Quantum chemical calculations at the B3LYP, MP2, and ri-CC2 levels support the conclusion of proton transfer from BZH(+) to the solvent moiety in the S0 state for hydration sizes larger than the critical value nc = 3. The vibronic spectrum of the S1 ← S0 transition (ππ(*)) of the n = 1 cluster is consistent with a cis-BZH(+)-H2O structure in both electronic states. The large blueshift of the S1 origin by 2106 cm(-1) upon hydration with a single H2O ligand indicates that the proton affinity of BZ is substantially increased upon S1 excitation, thus strongly destabilizing the hydrogen bond to the solvent. The adiabatic S1 excitation energy and vibronic structure calculated at the ri-CC2/aug-cc-pVDZ level agrees well with the measured spectrum, supporting the notion of a cis-BZH(+)-H2O geometry. The doubly hydrated species, cis-BZH(+)-(H2O)2, does not absorb in the spectral range of 23 000-27 400 cm(-1), because of the additional large blueshift of the ππ(*) transition upon attachment of the second H2O molecule. Calculations predict roughly linear and large incremental blueshifts for the ππ(*) transition in [BZ-(H2O)n]H(+) as a function of n. In the size range n ≥ 3, the calculations predict a proton transfer from the (H2O)nH(+) solvent back to the BZ solute upon electronic ππ(*) excitation.

  14. 苯甲醛改性双氰胺环氧固化剂的研究%Researches of benzaldehyde-modified dicyandiamide as curing agent for epoxy resin

    Institute of Scientific and Technical Information of China (English)

    程秀莲; 郭小伟; 杨艳玲

    2015-01-01

    A novel curing agent, the benzaldehyde-modified was prepared. The optimal synthesis conditions and curing conditions were studied. The results showed that the better processing conditions were as follows:pH value was 3-4,the mole ratio of dicyandiamide to benzaldehyde was 1.5:1, the reaction temperature and time were 95℃and 2 h,respectively, and the yield of modified dicyandiamide was up to 65.67%. The curing process and properties were investigated by testing the paint membrane hardness. When the modified dicyandiamide was used as the epoxy resin curing agent, the ratio of modified dicyandiamide to epoxy resin was 1 to 10, the curing temperature and time were 130℃ and 8 h, the paint membrane hardness HV1 was 47.52 and this curing temperature was 30℃ lower than that for dicyandiamide alone(160℃).%用苯甲醛对双氰胺进行改性,制备了一种新型改性双氰胺固化剂。对合成条件进行了优化,并对其固化条件进行了研究。结果表明,苯甲醛改性双氰胺的较佳工艺条件为pH值3~4,苯甲醛与双氰胺物质的量比为1∶1.5,于95℃,反应2 h,收率65.67%。通过测试涂层硬度来考察固化工艺与性能。作为环氧树脂固化剂单独使用时,与环氧树脂的质量比为1∶10,固化温度为130℃固化8 h 涂膜硬度HV1=47.52。比双氰胺体系固化温度(160℃)降低了30℃。

  15. Electronic and vibrational spectra of protonated benzaldehyde-water clusters, [BZ-(H2O)n≤5]H+: Evidence for ground-state proton transfer to solvent for n ≥ 3

    Science.gov (United States)

    Dopfer, Otto; Patzer, Alexander; Chakraborty, Shamik; Alata, Ivan; Omidyan, Reza; Broquier, Michel; Dedonder, Claude; Jouvet, Christophe

    2014-03-01

    Vibrational and electronic photodissociation spectra of mass-selected protonated benzaldehyde-(water)n clusters, [BZ-(H2O)n]H+ with n ≤ 5, are analyzed by quantum chemical calculations to determine the protonation site in the ground electronic state (S0) and ππ* excited state (S1) as a function of microhydration. IR spectra of [BZ-(H2O)n]H+ with n ≤ 2 are consistent with BZH+-(H2O)n type structures, in which the excess proton is localized on benzaldehyde. IR spectra of clusters with n ≥ 3 are assigned to structures, in which the excess proton is located on the (H2O)n solvent moiety, BZ-(H2O)nH+. Quantum chemical calculations at the B3LYP, MP2, and ri-CC2 levels support the conclusion of proton transfer from BZH+ to the solvent moiety in the S0 state for hydration sizes larger than the critical value nc = 3. The vibronic spectrum of the S1 ← S0 transition (ππ*) of the n = 1 cluster is consistent with a cis-BZH+-H2O structure in both electronic states. The large blueshift of the S1 origin by 2106 cm-1 upon hydration with a single H2O ligand indicates that the proton affinity of BZ is substantially increased upon S1 excitation, thus strongly destabilizing the hydrogen bond to the solvent. The adiabatic S1 excitation energy and vibronic structure calculated at the ri-CC2/aug-cc-pVDZ level agrees well with the measured spectrum, supporting the notion of a cis-BZH+-H2O geometry. The doubly hydrated species, cis-BZH+-(H2O)2, does not absorb in the spectral range of 23 000-27 400 cm-1, because of the additional large blueshift of the ππ* transition upon attachment of the second H2O molecule. Calculations predict roughly linear and large incremental blueshifts for the ππ* transition in [BZ-(H2O)n]H+ as a function of n. In the size range n ≥ 3, the calculations predict a proton transfer from the (H2O)nH+ solvent back to the BZ solute upon electronic ππ* excitation.

  16. Variation of transition-state structure as a function of the nucleotide in reactions catalyzed by dehydrogenases. 1. Liver alcohol dehydrogenase with benzyl alcohol and yeast aldehyde dehydrogenase with benzaldehyde.

    Science.gov (United States)

    Scharschmidt, M; Fisher, M A; Cleland, W W

    1984-11-01

    Primary intrinsic deuterium and 13C isotope effects have been determined for liver (LADH) and yeast (YADH) alcohol dehydrogenases with benzyl alcohol as substrate and for yeast aldehyde dehydrogenase (ALDH) with benzaldehyde as substrate. These values have also been determined for LADH as a function of changing nucleotide substrate. As the redox potential of the nucleotide changes from -0.320 V with NAD to -0.258 V with acetylpyridine-NAD, the product of primary and secondary deuterium isotope effects rises from 4 toward 6.5, while the primary 13C isotope effect drops from 1.025 to 1.012, suggesting a trend from a late transition state with NAD to one that is more symmetrical. The values of Dk (again the product of primary and secondary isotope effects) and 13k for YADH with NAD are 7 and 1.023, suggesting for this very slow reaction a more stretched, and thus symmetrical, transition state. With ALDH and NAD, the primary 13C isotope effect on the hydride transfer step lies in the range 1.3-1.6%, and the alpha-secondary deuterium isotope effect on the same step is at least 1.22, but 13C isotope effects on formation of the thiohemiacetal intermediate and on the addition of water to the thio ester intermediate are less than 1%. On the basis of the relatively large 13C isotope effects, we conclude that carbon motion is involved in the hydride transfer steps of dehydrogenase reactions.

  17. 5-Bromo-2-hydroxy-4-methyl-benzaldehyde inhibited LPS-induced production of pro-inflammatory mediators through the inactivation of ERK, p38, and NF-κB pathways in RAW 264.7 macrophages.

    Science.gov (United States)

    Kim, Kil-Nam; Ko, Seok-Chun; Ye, Bo-Ram; Kim, Min-Sun; Kim, Junseong; Ko, Eun-Yi; Cho, Su-Hyeon; Kim, Daekyung; Heo, Soo-Jin; Jung, Won-Kyo

    2016-10-25

    The aim of the present study was to investigate the effects of 5-bromo-2-hydroxy-4-methyl-benzaldehyde (BHMB) on inflammatory responses to lipopolysaccharide (LPS) in RAW 264.7 cells and the associated mechanism of action. BHMB concentration-dependently suppressed protein and mRNA expressions of iNOS and COX-2, thereby inhibiting the production of NO and PGE2 in LPS-stimulated RAW 264.7 cells. BHMB also reduced the mRNA expression of TNF-α, IL-6, and IL-1β in LPS-stimulated RAW 264.7 cells. To elucidate the mechanism underlying the anti-inflammatory activity of BHMB, we investigated the effects of BHMB on the mitogen-activated protein kinase and nuclear factor-kappa B (NF-κB) pathways. BHMB suppressed the phosphorylation and degradation of IκB-α and markedly inhibited the nuclear translocation of p65 and p50 in LPS-stimulated RAW 264.7 cells. The compound also inhibited the LPS-stimulated phosphorylation of ERK and p38. Taken together, these results illustrated that BHMB suppresses pro-inflammatory mediator and cytokine expression in LPS-stimulated RAW 264.7 cells by inhibiting the phosphorylation of ERK and p38 and the activation of NF-κB.

  18. Preparation, characterization and catalytic activity of CoFe2O4 nanoparticles as a magnetically recoverable catalyst for selective oxidation of benzyl alcohol to benzaldehyde and reduction of organic dyes.

    Science.gov (United States)

    Nasrollahzadeh, Mahmoud; Bagherzadeh, Mojtaba; Karimi, Hirbod

    2016-03-01

    The CoFe2O4 nanoparticles (NPs) performance was studied in the oxidation of benzyl alcohol (BzOH) to benzaldehyde (BzH) with hydrogen peroxide as an oxidant under solvent-free conditions. The influences of reaction conditions like the amount of catalyst, the molar ratio of H2O2:BzOH, reaction temperature and times on the oxidation of BzOH by using CoFe2O4 NPs were investigated in details. Under optimum conditions, excellent result, >99% conversation of BzOH to BzH as the only product, was obtained. The nanocatalyst was also used for the reduction of 4-nitrophenol (4-NP), Congo red (CR), Methylene blue (MB) in water at room temperature. The magnetic properties of the catalyst provided a convenient and easy route for the separation of the catalyst from the reaction mixture by an external bar magnet. No obvious loss of activity was observed when the spent catalyst reused in three consecutive runs.

  19. The mechanism of the formation of the hemiaminal and Schiff base from the benzaldehyde and triazole studied by means of the topological analysis of electron localisation function and catastrophe theory

    Science.gov (United States)

    Berski, Slawomir; Zbigniew Ciunik, Leszek

    2015-04-01

    The mechanisms of reaction of benzaldehyde (ald) with 4-amine-4H-1,2,4-triazole (4at), leading to Schiff base (Sch) and water, were investigated using topological analysis of the electron localisation function and catastrophe theory. Two reactions (synthesis of hemiaminal and synthesis of Schiff base) are represented by one catastrophe sequence: ald+4at: 1-14-[FF†F†FFTS1FF†F†FF†F†CF†]-2-9-[C†FFTS3F†F†FFF]-0:Sch+H2O with only fold (F) and cusp (C) catastrophes. The first reaction, in which a molecule of the hemiaminal is formed, consists of 14 steps separated by 13 catastrophes. The mechanism is non-concerted. The covalent bond C-N is formed after the formation of the O-H bond is terminated. The Schiff base formation through the water molecule elimination in the second reaction requires nine steps with eight catastrophes. The mechanism is non-concerted because first the C-O bond is broken and then the proton transfer occurs that results in the O-H bond creation.

  20. Electronic and vibrational spectra of protonated benzaldehyde-water clusters, [BZ-(H{sub 2}O){sub n≤5}]H{sup +}: Evidence for ground-state proton transfer to solvent for n ≥ 3

    Energy Technology Data Exchange (ETDEWEB)

    Dopfer, Otto, E-mail: dopfer@physik.tu-berlin.de; Patzer, Alexander; Chakraborty, Shamik [Institut für Optik und Atomare Physik, Technische Universität Berlin, Hardenbergstrasse 36, 10623 Berlin (Germany); Alata, Ivan; Omidyan, Reza; Broquier, Michel [Institut des Sciences Moleculaires d’Orsay, UMR-CNRS 8214, and Centre Laser de l’Université Paris Sud/LUMAT FR 2764, Batiment 106, l’Université Paris Sud 11, 91405 Orsay Cedex (France); Dedonder, Claude; Jouvet, Christophe [Physique des Interactions Ioniques et Moléculaires, UMR-CNRS 7345 Aix Marseille Université, Avenue Escadrille Normandie-Niémen, 13397 Marseille Cedex 20 (France)

    2014-03-28

    Vibrational and electronic photodissociation spectra of mass-selected protonated benzaldehyde-(water){sub n} clusters, [BZ-(H{sub 2}O){sub n}]H{sup +} with n ≤ 5, are analyzed by quantum chemical calculations to determine the protonation site in the ground electronic state (S{sub 0}) and ππ{sup *} excited state (S{sub 1}) as a function of microhydration. IR spectra of [BZ-(H{sub 2}O){sub n}]H{sup +} with n ≤ 2 are consistent with BZH{sup +}-(H{sub 2}O){sub n} type structures, in which the excess proton is localized on benzaldehyde. IR spectra of clusters with n ≥ 3 are assigned to structures, in which the excess proton is located on the (H{sub 2}O){sub n} solvent moiety, BZ-(H{sub 2}O){sub n}H{sup +}. Quantum chemical calculations at the B3LYP, MP2, and ri-CC2 levels support the conclusion of proton transfer from BZH{sup +} to the solvent moiety in the S{sub 0} state for hydration sizes larger than the critical value n{sub c} = 3. The vibronic spectrum of the S{sub 1} ← S{sub 0} transition (ππ{sup *}) of the n = 1 cluster is consistent with a cis-BZH{sup +}-H{sub 2}O structure in both electronic states. The large blueshift of the S{sub 1} origin by 2106 cm{sup −1} upon hydration with a single H{sub 2}O ligand indicates that the proton affinity of BZ is substantially increased upon S{sub 1} excitation, thus strongly destabilizing the hydrogen bond to the solvent. The adiabatic S{sub 1} excitation energy and vibronic structure calculated at the ri-CC2/aug-cc-pVDZ level agrees well with the measured spectrum, supporting the notion of a cis-BZH{sup +}-H{sub 2}O geometry. The doubly hydrated species, cis-BZH{sup +}-(H{sub 2}O){sub 2}, does not absorb in the spectral range of 23 000–27 400 cm{sup −1}, because of the additional large blueshift of the ππ{sup *} transition upon attachment of the second H{sub 2}O molecule. Calculations predict roughly linear and large incremental blueshifts for the ππ{sup *} transition in [BZ-(H{sub 2}O){sub n

  1. Redox cycling of a copper complex with benzaldehyde nitrogen mustard-2-pyridine carboxylic acid hydrazone contributes to its enhanced antitumor activity, but no change in the mechanism of action occurs after chelation.

    Science.gov (United States)

    Yang, Yinli; Li, Cuiping; Fu, Yun; Liu, Youxun; Zhang, Yu; Zhang, Yanfang; Zhou, Pingxin; Yuan, Yanbin; Zhou, Sufeng; Li, Shaoshan; Li, Changzheng

    2016-03-01

    Many anticancer drugs used in the clinical have potent metal chelating ability. The formed metal complex(es) may exhibit improved (or antagonistic) antitumor activity. However, the underlying mechanism has received limited attention. Therefore, investigation of the mechanism involved in the change upon chelation is required to extend our understanding of the effects of various drugs. In the present study, the proliferation inhibition effect of benzaldehyde nitrogen mustard-2-pyridine carboxylic acid hydrazone (BNMPH) and its copper complex on tumor cell lines was investigated. The copper chelate exhibited almost a 10-fold increase in antitumor activity (with IC50 copper complex induced reactive oxygen species (ROS) generation, and caused upregulation of caspase 8 and Bax as well as the downregulation of Bcl-2, indicating that apoptosis was involved in the cytotoxic effects. DNA fragmentation noted in the comet assay further supported ROS involvement. The present study indicated that BNMPH and its copper complex effectively induced S phase arrest and the cell cycle arrest was associated with the downregulation of cyclin D1. The formation of acidic vesicular organelles (AVOs) and an increase in cleaved LC3-II demonstrated that autophagy occurred in the HepG2 cells treated with the agents. Taken together, BNMPH and its copper complex exhibited proliferation inhibition via apoptosis, cell cycle arrest and autophagy, which was dependent on ROS. The enhanced antitumor activity of the copper complex was due to its redox-cycling ability, but the mechanism was not altered compared to BNMPH. Our findings may significantly contribute to the understanding of the anti-proliferative effect of BNMPH and its copper complex.

  2. 苯甲醛、2-异丁腈与丙二酸二乙酯的三组分Passerini反应%Three components Passerini reactions of Benzaldehyde, 2 -Isobutyronitrile and Diethyl Malonate

    Institute of Scientific and Technical Information of China (English)

    陈懿; 谢兵; 高斌

    2012-01-01

    The paper explores three multieomponent Passerini reactions by using diethyl malonate instead of car- boxylic acid or alcohol. The significant applied value of compounds including double functional group diethyl malonate derivative from benzaldehyde, 2 - isobutyrenitrile and diethyl malonate was synthesized by one - pot in moderate yield by using H2SO4 as catalyst at microwave and heat under free - solvent. The optimized reaction condition follows the aspects: 2mL H2SO4 as catalyst; reaction temperature was 120 ℃, power rating for micrwave was 300 W and reaction time was 40 min.%探索用丙二酸二乙酯替代羧酸或醇进行三组分Passerini反应。在无溶剂条件下,用浓硫酸作为催化剂,苯甲醛、2-异丁腈和丙二酸二乙酯通过微波辅助和加热,一锅法进行三组分Passerini反应,以中等收率得到具有重要应用价值的双官能团化合物丙二酸二乙酯衍生物。该反应的最佳条件为:以浓硫酸为催化剂,催化剂用量为2mL,反应温度为120℃,微波功率为BOOW,反应时间为40min。

  3. Template Synthesis of a Tetraaza Macrocycle Which Involves Benzaldehyde Rather Than Formaldehyde as a Building Block. Isolation and Structure Determination of the Open-Chain Schiff Base Intermediate Complex.

    Science.gov (United States)

    Fabbrizzi, Luigi; Licchelli, Maurizio; Manotti Lanfredi, Anna Maria; Vassalli, Omar; Ugozzoli, Franco

    1996-03-13

    The classical formaldehyde building block has been replaced by the bulkier benzaldehyde in the Cu(II) template synthesis of the cyclam-like tetraaza macrocycle of type 1, in which nitroethane operated as locking fragment. The synthetic pathway involves three distinct steps: (i) Schiff base condensation of the metal-free open-chain tetramine; (ii) Cu(II) coordination and preorientation of the Schiff base; (iii) nucleophilic attack by the deprotonated nitroethane fragment and formation of the macrocyclic complex. Both the Schiff base Cu(II) complex and the Cu(II) macrocyclic complex were isolated in a crystalline form and their molecular structures were determined: {N-[2-((E)-benzylideneamino)ethyl]-N'-[2-((Z)-benzylideneamino)ethyl]propane-1,3-diamine}copper(II) nitrate: triclinic, space group P&onemacr;, with a = 12.296(5) Å, b = 10.787(6) Å, c = 10.547(7) Å, V = 1161(1) Å(3), and Z = 2 (R = 0.055, R(w) = 0.061); [(5R,6S,7S)-6-methyl-6-nitro-5,7-diphenyl-1,4,8,11-tetraazacyclotetradecane]copper(II) perchlorate: monoclinic, space group P2(1)/n, with a = 15.246(5) Å, b = 23240(7) Å, c = 8.540(4) Å, V = 2980(2) Å(3), and Z = 4 (R = 0.095, R(w) = 0.095). This allowed us to define mechanistic details of the macrocyclization process. It is suggested that the same three-step pathway takes place in the much easier and faster one-pot template syntheses of cyclam-like macrocyles, which involve formaldehyde as a building block.

  4. Novel cytochrome p450 bioactivation of a terminal phenyl acetylene group: formation of a one-carbon loss benzaldehyde and other oxidative products in the presence of N-acetyl cysteine or glutathione.

    Science.gov (United States)

    Subramanian, Raju; Tam, Janet; Aidasani, Divesh; Reid, Darren L; Skiles, Gary L

    2011-05-16

    Compounds 1 (N1-(3-ethynylphenyl)-6-methyl-N5-(3-(6-(methylamino)pyrimidin-4-yl)pyridin-2-yl) isoquinoline-1,5-diamine) and 2 (N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine; Erlotinib/Tarceva) are kinase inhibitors that contain a terminal phenyl acetylene moiety. When incubated in the presence of P450 and NADPH, the anticipated phenyl acetic acid metabolite was formed. When 10 mM of N-acetyl-l-cysteine was added to the incubation mixtures, the phenyl acetic acid product was reduced and at 25 mM or higher concentration of NAC, formation of the phenyl acetic acid was abolished. Instead, the phenyl acetylene moiety lost a carbon and formed a benzaldehyde product. Other oxidation products incorporating one or more equivalents of NAC were also observed. The identities of the metabolites were characterized by MS and NMR. Addition of deferoxamine or ascorbic acid diminished the formation of the NAC influenced products. Similar products were also observed when 1 or 2 were incubated in P450 reactions supplemented with GSH, in Fenton reactions supplemented with NAC or GSH, and in peroxidase reactions supplemented with NAC. We propose the thiols act as a pro-oxidant readily undergoing a one-electron oxidation to form thiyl radicals which in turn initiates the formation of other peroxy radicals that drive the reaction to the observed products. These in vitro findings suggest that one-electron oxidation of thiols may promote the cooxidation of xenobiotic substrates.

  5. A novel azo-aldehyde and its Ni(II) chelate; synthesis, characterization, crystal structure and computational studies of 2-hydroxy-5-{(E)-[4-(propan-2-yl)phenyl]diazenyl}benzaldehyde

    Science.gov (United States)

    Eren, Tuğba; Kose, Muhammet; Sayin, Koray; McKee, Vickie; Kurtoglu, Mukerrem

    2014-05-01

    A novel azo-salicylaldeyde, 2-hydroxy-5-{(E)-[4-(propan-2-yl)phenyl]diazenyl} benzaldehyde and its Ni(II) chelate were obtained and characterized by analytical and spectral techniques. Molecular structure of the azo chromophore containing azo-aldehyde was determined by single crystal X-ray crystallography. X-ray data show that the compound crystallizes in the orthorhombic, Pbca space group with unit cell parameters a = 11.2706(9), b = 8.3993(7), c = 28.667(2) Å, V = 2713.7(4) Å3 and Z = 8. There is a strong phenol-aldehyde (OH⋯O) hydrogen bond forming a S(6) hydrogen bonding motif in the structure. There is also a weaker inter-molecular phenol-aldeyhde (OH⋯O) hydrogen bonding resulting in a dimeric structure and generating a D22(4) hydrogen bonding motif. Hydrogen bonded dimers are linked by π-π interactions within the structure. The azo-aldehyde ligand behaved as bidentate, coordinating through the nitrogen atom of the azomethine group and or oxygen atom of phenolic hydroxyl group. Additionally, optimized structures of the three possible tautomers of the compound were obtained using B3LYP method with 6-311++G(d,p), 6-31G and 3-21G basis sets in the gas phase. B3LYP/6-311++G(d,p) level is found to be the best level for calculation. The electronic spectra of the compounds in the 200-800 nm range were obtained in three organic solvents.

  6. Synthesis of Cyclohexanone Ethylene Ketal and Benzaldehyde Ethylene Acetal by Chloroaluminate Ionic Liquid%氯铝酸型离子液体催化合成环己酮(苯甲醛)乙二醇缩酮(醛)

    Institute of Scientific and Technical Information of China (English)

    胡应喜; 张彧; 潘欣欣

    2015-01-01

    Cyclohexanone ethylene ketal and benzaldehyde ethylene acetal were synthesized with chloroalu-minate ionic liquid as catalyst.The effects of catalyst amount,molar ratio of cyclohexanone(benzaldehyde)to ethylene glycol,and water-carrying agent amount on the reaction were investigated.The optimum synthetic con-ditions were obtained as follows:catalyst amount was 1.0 g,the molar ratio of cyclohexanone(benzaldehyde)to ethylene glycol was 1∶1.8,water-carrying agent amount was 30 mL.The physical property and structure of the synthetic product were characterized by elemental analysis,FTIR,refractive index and 1 HNMR.%以氯铝酸型离子液体为催化剂合成了环己酮(苯甲醛)乙二醇缩酮(醛),考察了催化剂用量、酮(醛)醇物质的量比及带水剂用量对反应的影响。确定最优合成条件为:催化剂用量1.0 g、酮(醛)醇物质的量比1∶1.8、带水剂环己烷用量30 mL。通过元素分析、红外光谱、折光率和1 HNMR 对产品进行了物性和结构表征。

  7. STUDY ON THE PERFORMANCE OF Co-SBA-15 CATALYST FOR CATALYTIC OXIDATION OF STYRENE TO BENZALDEHYDE%Co-SBA-15催化苯乙烯氧化制苯甲醛反应性能的研究

    Institute of Scientific and Technical Information of China (English)

    白向向; 沈健

    2011-01-01

    以Co(NO3)2·6H2O为钴源制备Co-SBA-15介孔分子筛,并用XRD、BET方法对Co-SBA-15结构进行表征.结果表明,负载钴的SBA-15具有介孔分子筛的结构特征.以质量分数为30%的H2O2为氧化剂,丙酮为溶剂,对Co-SBA-15催化氧化苯乙烯反应进行研究.在苯乙烯用量5 mL、n(H2O2)∶n(苯乙烯)=2、催化剂焙烧温度500℃、Co(15 %)-SBA-15用量100mg、丙酮用量10mL、反应温度100℃、反应时间4h的条件下,苯乙烯转化率为99.12%,苯甲醛选择性为77.62%,苯甲醛收率为76.94%.%Cobalt-containing mesoporous molecular sieves Co-SBA-15 were prepared using Co(NO3) · 6H2O as cobalt source and the obtained molecular sieves were characterized by XRD and BET. Test results showed that Co-SBA-15 possessed the characteristic structural features of mesoporous molecular sieve. The performance of Co-SBA-15 for catalytic oxidation of styrene was investigated using 30% H2O2 as oxidant and acetone as solvent. Under the conditions of using 5 mL of styrene, 10 mL of acetone, 100 mg Co(15%)-SBA-15 catalyst calcined at 500 ℃ ,H2O2/styrene molar ratio of 2,a reaction temperature of 100 ℃ and a reaction time of 4 h,the conversion of styrene reached 99. 12% ,the selectivity and yield of benzaldehyde was 77. 62% and 76. 94% ,respectively.

  8. Overtone spectroscopy of some benzaldehyde derivatives

    Indian Academy of Sciences (India)

    P K Srivastava; D K Rai; S B Rai

    2001-06-01

    Overtone spectrum of , and -nitrobenzaldehydes and -chlorobenzaldehyde has been studied in 2000–12000 cm-1 region. Vibrational frequencies and anharmonicity constants for aryl as well as alkyl CH stretch vibrations have been determined. We have also determined the internuclear distances for the aryl CH bond in the different molecules. The small variation observed in these distances is an indication of the substitution effect. It is observed that in the case of -disubstituted benzenes, the shift in aryl CH bond is proportional to sum of the Hammet of the substituents. However in the case of -disubstituted benzenes it is only 80% of the para-substituted shift.

  9. 2-[4-(2-Formylphenoxybutoxy]benzaldehyde

    Directory of Open Access Journals (Sweden)

    Aliakbar Dehno Khalaji

    2011-09-01

    Full Text Available In the crystal structure of the title compound, C18H18O4, the full molecule is generated by the application of an inversion centre. The molecule is essentially planar, with an r.m.s. deviation of 0.017 (1 Å for all non-H atoms. The molecules are linked through intermolecular C—H...O interactions to form a molecular sheet parallel to the (overline{1}02 plane.

  10. Spectroscopic studies and structure of 3-methoxy-2 -[(2,4,4,6,6-pentachloro-1,3,5,2{lambda}{sup 5},4{lambda}{sup 5},6{lambda}{sup 5}-triazatriphosphin-2-yl)oxy] benzaldehyde

    Energy Technology Data Exchange (ETDEWEB)

    Oezay, H.; Yildiz, M., E-mail: myildiz@comu.edu.tr [Canakkale Onsekiz Mart University, Department of Chemistry, Faculty of Science and Arts (Turkey); Uenver, H.; Durlu, T. N. [Ankara University, Department of Physics, Faculty of Science (Turkey)

    2013-01-15

    The compound called 3-methoxy-2- [(2,4,4,6,6-pentachloro-1,3,5,2{lambda}{sup 5},4{lambda}{sup 5},6{lambda}{sup 5}-triazatriphosphin-2-yl)oxy] benzaldehyde has been synthesized from the reaction of 2-hydroxy-3-methoxybenzaldehyde with hexachlorocyclotriphosphazene. It has been characterized by elemental analysis, MS, IR, {sup 1}H NMR, {sup 13}C NMR, {sup 31}P NMR and UV-visible spectroscopic techniques. The structure of the title compound has been determind by X-ray analysis. Crystals are orthorhombic, space group P2{sub 1}2{sub 1}2{sub 1}, Z = 4, a = 7.705(1), b = 12.624(1), c = 17.825(2) A, R{sub 1} = 0.0390 and wR{sub 2} = 0.1074 [I > 2{sigma}(I)], respectively.

  11. SBA-15负载的Cu(II)席夫碱配合物催化的苯乙烯氧化反应制备苯甲醛%Catalytic oxidation of styrene to benzaldehyde over a copper Schiff-base/SBA-15 catalyst

    Institute of Scientific and Technical Information of China (English)

    朱学成; 沈如伟; 张利雄

    2014-01-01

    The amino-modified mesoporous material SBA-15 (NH2-SBA-15) was prepared via co-condensation of tetraethylorthosilicate with 3-aminopropyltriethoxysilane in the presence of an amphiphilic triblock copolymer as a pore-directing agent under acidic conditions. The SBA-15-supported Cu Schiff-base complex (Cu-SBA-15) was then synthesized by condensation of salicylaldehyde with NH2-SBA-15, followed by the addition of a solution of Cu(NO3)2. The supported complex was sys-tematically characterized by elemental analysis, inductive coupled high frequency plasma atomic emission spectrometry, powder X-ray diffraction, Fourier transform infrared spectroscopy, ultravi-olet-visible spectroscopy, field scanning electron microscopy, transmission electron microscopy, N2 absorption-desorption, and thermo gravimetric analysis, and was used as the catalyst for the selec-tive oxidation of styrene to benzaldehyde. The influence of the reaction parameters was assessed. The maximum conversion of styrene was 84.4%and the selectivity for benzaldehyde was 83.9%, when the reaction was conducted with a 2:1 molar ratio of H2O2:styrene in the presence of 3.8 wt%catalyst at 100 °C for 8 h. The TOF was 261.1 h-1, and the catalyst could be used three times without significant loss of activity. The uniformly sized pore channels, high specific surface area, and well-distributed active centers of the catalyst may contribute to the high activity.%子筛SBA-15(NH2-SBA-15),再利用其中氨基与水杨醛的缩合反应制备SBA-15固载的席夫碱,该席夫碱与Cu(NO3)2溶液反应最终制成固定于SBA-15的Cu(II)席夫碱配合物多相催化剂Cu-SBA-15.采用X射线衍射、红外光谱仪、紫外可见分光光度计、场发射电镜、透射电镜、N2吸附-脱附、元素分析、原子发射光谱和热重分析对催化剂进行了表征,并将此催化剂用于无有机溶剂条件下催化氧化苯乙烯制备苯甲醛,考察了反应时间、反应温度、H2O2用量、水的用量

  12. 2′-硼酸基苯甲醛-7-(8-羟基-5-磺酸基)喹啉腙衍生物的合成及对Pb2+的识别%Synthesis of 2′-Borono-benzaldehyde-7- (8-hydroxy-5-sulfoacid)Qninoline Hydrazone and Recognition of Pb2 +

    Institute of Scientific and Technical Information of China (English)

    肖敏; 张丽娜; 吴芳英

    2012-01-01

    合成了2 ′,3′和4′-硼酸基苯甲醛-7-(8-羟基-5-磺酸基)喹啉腙衍生物(化合物1~3),研究了硼酸基团取代位置对主体分子识别金属离子客体性能的影响,比较了不同主体分子与Pb2+结合能力的差异.研究结果表明,在pH=7.0的KH2 PO4 -NaOH缓冲溶液中,3种腙衍生物对Pb2+均具有选择性识别作用,主客体分子间形成1∶1型的发光配合物.其中邻位取代的化合物1与Pb2+的结合能力比化合物2和3强,配合物1-P2+的最大发射波长为477 nm,稳定常数为1.1 ×103 L/mol.其它金属离子如Cu2+,Mn2+,Mg2+,Fe2+,Ca2+,C02+,Ni2+,Hg2+,Cd2+和Ag+等对主体分子荧光光谱的影响较小.同时,荧光强度的变化值与p2+浓度在0.36~ 10 μmol/L范围内呈现良好的线性关系,相关系数R=0.9976(n=16),检出限为0.23 μmol/L.将此方法用于环境水样中Pb2+的测定,回收率为92%~108%.%2', 3' and 4'-borono-benzaldehyde-7-( 8-hydroxy-5-sulfoacid) quinoline hydrazone derivatives (1-3) were synthesized. The influences of host molecules with boric acid at different replace positions on the recognition of metal ions was investigated. The combining ability of host compounds with lead ion was compared. Research results showed that 2'-borono benzaldehyde-7-(8-hydroxy-5-sulfoacid) quinoline hydrazone (1) possessed highly selective binding and recognition to Pb.2+in the KH2PO4-NaOH buffer solution with a pH value of 7. 0. The 1 : 1 complexes between host 1 and lead ion formed and they emitted strong fluorescence. The binding ability of host 1 with Pb2+ was the strongest among hosts 1-3. The emission wavelength of complex 1-Pb2+ was 477 nm and the binding constant was 1. l×l03 L/mol. The presence of the other metal ions led fluorescent spectra of hosts 1-3 little change, for example Mn2+ , Cu2+, Mg2+, Fe2+, Ca2+, Co2+, Hg2+, Ni2+, Cd2+, Ag+ and so on. Fluorescence intensity and the concentration of Pb2 + presented good linear relationship from 0. 36 μrnol/L to 10

  13. 磺酸化介孔二氧化硅的合成及催化苯甲醛和乙二醇的加成反应%Preparation of sulfo-functionlized mesoporous silica and its catalytic performance in addition of benzaldehyde and ethylene glycol

    Institute of Scientific and Technical Information of China (English)

    胡建; 夏成波; 彭静; 郑净植

    2011-01-01

    以CTAB为模板剂,通过溶胶-凝胶法制备了介孔二氧化硅,将聚(苯乙烯-二乙烯苯)包覆在介孔二氧化硅表面,并进行磺酸化制备了一种新型的固体酸催化剂;通过FT-IR、TGA、TEM等表征方法对合成的磺酸化介孔二氧化硅进行了表征.结果表明:表面聚合物基团和磺酸根基团成功地引入到了二氧化硅表面,磺酸化的介孔二氧化硅具有较好的孔道有序结构.磺酸化介孔二氧化硅对苯甲醛和乙二醇的加成反应表现出了较高的酸催化性能.%The mesoporous silica was synthesized by sol-gel method using CTAB as template, and then a novel ordered mesoporous solid acid catalyst was prepared by sulfonation of polymers coating on surface of mesoporous silica.The samples were characterized by FT-IR, TGA and TEM.The results indicated that the meso-structure of the sample was retained, and the polymer groups and -SO3H groups had been successfully incorporated on the surface of silica.The sample show high catalytic performance toward the addition reaction of benzaldehyde and ethylene glycol.

  14. O-季铵化-N-(4-十二烷氧基)壳聚糖苯甲醛席夫碱的制备及胶束pH响应性%Preparation and micelle pH response ofO-quaternary ammonium-N-(4-dodecyloxy) chitosan benzaldehyde Schiff’s bass

    Institute of Scientific and Technical Information of China (English)

    林意华; 李明春; 辛梅华; 陈燕燕

    2015-01-01

    制备双亲性的O-季铵化-N-(4-十二烷氧基)壳聚糖苯甲醛席夫碱(QA-CS-DBA),采用FTIR、1H NMR及元素分析对产物进行表征。通过超声法制备QA-CS-DBA载酮洛芬胶束,考察胶束的临界胶束浓度、粒径、Zeta电位、载药量和包封率,并对胶束在不同 pH 值条件下的药物释放行为及 Zeta 电位变化进行研究。结果表明, QA-CS-DBA能将酮洛芬包载于胶束疏水内核,载药量为39.37%,包封率为46.04%,载药胶束粒径为341nm, Zeta电位为30.8mV。胶束Zeta电位及载药胶束的药物释放行为具有pH响应性。%AmphiphilicO-quaternary ammonium-N-(4-dodecyloxy) chitosan benzaldehyde Schiff’s base (QA-CS- DBA) was prepared. FTIR,1H NMR and EA were used to confirm its structure. The micelle of QA-CS-DBA carrying ketoprofen was made by ultrasounding. The CMC,size,Zeta potential,drug loading capacity and encapsulation efficiency were studied,especially the behavior of drug release and the change of Zeta potential in different PBS buffer solution with different pH. The result shows that QA-CS-DBA could form stable drug loading micelles carrying ketoprofen with the size about 341nm. The drug loading capacity and the encapsulation efficiency are 39.37% and 46.04% respectively and the Zeta potential is 30.8mV. With pH changing between 7.40 and 6.50,the micelle shows different Zeta potentials and different behaviors in drug release.

  15. 相转移催化合成4-{2-[N-甲基-N-(2-吡啶基)]氨基乙氧基}苯甲醛%Synthesis of 4- { 2- [ N-methyl-N- (2-pyridyl) ] aminoethoxy } benzaldehyde by phase-transfer catalysis

    Institute of Scientific and Technical Information of China (English)

    秦丙昌; 张高宾; 李俊成; 靳晓宁

    2012-01-01

    以2-氯吡啶(1)、2-甲氨基乙醇(2)和4-氟苯甲醛(4)为主要原料,经2步反应合成了4-{2-[N-甲基-N-(2-吡啶基)氨基乙氧基]}苯甲醛(5).第1步反应n(2)∶n(1)=4∶1,反应温度160℃,反应时间约6h,采用减压蒸馏进行后处理,2-[N-甲基-N-(2-吡啶基)氨基]乙醇(3)的收率在93%以上,过量2的回收率在97%以上,回收的2可以重复使用.第2步反应用氢氧化钠做碱性试剂,用甲苯和水分别做为两相的溶剂,在相转移催化剂CTAB作用下进行,经优化后5的收率可达90%以上.2步反应总收率达83%以上.%4-12-[N-Methyl-N-(2-pyridyl) ] aminoethoxy | benzaldehyde(5)was synthesized by a two-steps process with 2-chloropyr-idine(l) ,2-(methylamino) ethanol(2) ,and 4-fluorobenzaldehyde(4) as principal raw materials. In first step of the process, the mole ratio of 2 to 1 was 4:1 .reaction temperature 160℃ .reaction time about 6 h,and adopted vacuum distillation in work-up procedure. Under such conditions,the yield of 2-[n-methyl-n-(2-pyridyl)amino]ethanol(3) was more than 93% ,the rate of recovery of the excess 2 was more than 97% ,and recovered 2 could be cyclically used. The second step of process was carried out with sodium hydroxide as basic reagent,toluene and water as solvent of two phases respectively ,CTAB as phase-transfer catalyst,gave 5 in more than 90% yield under optimal conditions. The above two steps gave 5 in more than 83% overall yield.

  16. Biocatalytic oxidation of benzyl alcohol to benzaldehyde via hydrogen transfer

    NARCIS (Netherlands)

    Orbegozo, Thomas; Lavandera, Iván; Fabian, Walter M.F.; Mautner, Barbara; Vries, Johannes G. de; Kroutil, Wolfgang

    2009-01-01

    Various types of biocatalysts like oxidases, alcohol dehydrogenases, and microbial cells were tested for the oxidation of benzyl alcohol. Oxidases in combination with molecular oxygen led to low conversion. Alcohol dehydrogenases and microbial cells were tested in a hydrogen transfer reaction employ

  17. 4-{2-[2-(4-Formylphenoxyethoxy]ethoxy}benzaldehyde

    Directory of Open Access Journals (Sweden)

    Zhen Ma

    2011-06-01

    Full Text Available The title compound, C18H18O5, was obtained by the reaction of 4-hydroxybenzaldehyde with bis(2,2-dichloroethyl ether in dimethylformamide. In the crystal, the molecule lies on a twofold rotation axis that passes through the central O atom of the aliphatic chain, thus leading to one half-molecule being present per asymmetric unit. The carbonyl, aryl and O—CH2—CH2 groups are almost coplanar, with an r.m.s. deviation of 0.030 Å. The aromatic rings are approximately perpendicular to each other, forming a dihedral angle of 78.31 sh;H...O hydrogen bonds and C—H...π interactions help to consolidate the three-dimensional network.

  18. Oxidation of Benzaldehyde by Quinolinium Chloro Chromate in Presence of Ctab in Sulphuric Acid Medium

    Directory of Open Access Journals (Sweden)

    Kanchan Kumar Rai

    2013-12-01

    Full Text Available The study of oxidation of organic compounds is of immense importance both from mechanistic and synthetic points of view. It has a bearing on the chemical processes of life also. Investigation of the kinetics and mechanism of redox reactions has attracted the attention of chemists world over and mechanisms of several reactions have been clearly delineated. The mechanism of a chemical reaction cannot be fully described without the determination of its rate. The kinetic study of a wide range of chemical processes is seen to be of essential importance, not only in pure research but increasingly in industrial research, development and, in some instances, in quality control and analysis as well. Kinetic methods have become an essential technique in photochemistry, enzyme chemistry, study of chemical catalysis etc.

  19. Amino acid-catalysed retroaldol condensation: the production of natural benzaldehyde and other flavour compounds

    NARCIS (Netherlands)

    Wolken, W.A.M.; Tramper, J.; Werf, van der M.J.

    2004-01-01

    The amino acid-catalysed retroaldol condensation previously described for citral has been extended to other alpha,beta-unsaturated aldehydes. In the presence of glycine and an elevated pH, six other alpha,beta-unsaturated aldehydes also underwent retroaldol condensation. Crotonaldehyde, as well as i

  20. Amino acid-catalysed retroaldol condensation : the production of natural benzaldehyde and other flavour compounds

    NARCIS (Netherlands)

    Wolken, WAM; Tramper, J; van der Werf, MJ

    2004-01-01

    The amino acid-catalysed retroaldol condensation previously described for citral has been extended to other alpha,beta-unsaturated aldehydes. In the presence of glycine and an elevated pH, six other alpha,beta-unsaturated aldehydes also underwent retroaldol condensation. Crotonaldehyde, as well as i

  1. Amino acid-catalysed retroaldol condensation: The production of natural benzaldehyde and other flavour compounds

    NARCIS (Netherlands)

    Wolken, W.A.M.; Tramper, J.; Werf, M.J. van der

    2004-01-01

    The amino acid-catalysed retroaldol condensation previously described for citral has been extended to other α,β -unsaturated aldehydes. In the presence of glycine and an elevated pH, six other α,β-unsaturated aldehydes also underwent retroaldol condensation. Crotonaldehyde, as well as its proposed i

  2. 4-[4-(1H-Tetrazol-5-ylphenoxy]benzaldehyde

    Directory of Open Access Journals (Sweden)

    Jing Lu

    2011-11-01

    Full Text Available The asymmetric unit of the title compound, C14H10N4O2, contains two independent molecules with similar structures. In one molecule, the tetrazole ring is oriented at dihedral angles of 17.71 (16 and 57.13 (17°, respectively, to the central benzene ring and the terminal benzene ring; in the other molecule, the corresponding dihedral angles are 16.46 (18 and 75.87 (18°. Intermolecular N—H...N hydrogen bonds and weak C—H...O and C—H...N hydrogen bonds occur in the crystal structure.

  3. (E-Benzaldehyde O-{[3-(pyridin-3-ylisoxazol-5-yl]methyl}oxime

    Directory of Open Access Journals (Sweden)

    Rodolfo Moreno-Fuquen

    2012-04-01

    Full Text Available The asymmetric unit of the title compound, C16H13N3O2, contains two independent molecules in which the pyridine and benzene rings form dihedral angles of 81.7 (2 and 79.8 (2°, indicating the twist in the molecules. In the crystal, weak C—H...N interactions link molecules into chains along [100].

  4. NCA nucleophilic radiofluorination on substituted benzaldehydes for the preparation of [18F]fluorinated aromatic amino acids

    Energy Technology Data Exchange (ETDEWEB)

    Wadsak, Wolfgang [Department of Nuclear Medicine, Medical University of Vienna (Austria)]. E-mail: wolfgang.wadsak@meduniwien.ac.at; Wirl-Sagadin, Barbara [Department of Nuclear Medicine, Medical University of Vienna (Austria); Department of Inorganic Chemistry, University of Vienna (Austria); Mitterhauser, Markus [Department of Nuclear Medicine, Medical University of Vienna (Austria); Department of Pharmaceutical Technology and Biopharmaceuticals, University of Vienna (Austria); Hospital Pharmacy of the General Hospital of Vienna (Austria); Mien, Leonhard-Key [Department of Nuclear Medicine, Medical University of Vienna (Austria); Department of Pharmaceutical Technology and Biopharmaceuticals, University of Vienna (Austria); Department of Psychiatry, Medical University of Vienna (Austria); Ettlinger, Dagmar E. [Department of Nuclear Medicine, Medical University of Vienna (Austria); Keppler, Bernhard K. [Department of Inorganic Chemistry, University of Vienna (Austria); Dudczak, Robert [Department of Nuclear Medicine, Medical University of Vienna (Austria); Kletter, Kurt [Department of Nuclear Medicine, Medical University of Vienna (Austria)

    2006-03-15

    Nucleophilic aromatic substitution is a challenging task in radiochemistry. Therefore, a thorough evaluation and optimisation of this step is needed to provide a satisfactory tool for the routine preparation of [{sup 18}F]fluorinated aromatic amino acids. Two methods, already proposed elsewhere, were evaluated and improved. The yields for the radiofluorination were increased whereas activity loss during solid phase extraction was observed. Radiochemical yields for the two methods were 92.7{+-}5.5% (method 1) and 92.1{+-}12.3% (method 2) for conversion and 11.1{+-}2.8% (method 1) and 34.8{+-}0.6% (method 2) for purification, respectively. In total, we demonstrate an optimised method for the preparation of this important class of [{sup 18}F]fluorinated synthons for PET.

  5. Isolation of flavonoids from Aleurites moluccana using chitosan modified with benzaldehyde (CH-Bz) as chromatographic support.

    Science.gov (United States)

    Girardi, L G J; Morsch, M; Cechinel-Filho, V; Meyre-Silva, C; Rodrigues, C A

    2003-09-01

    This paper describes the preparation, characterization and use of a derivative of chitosan as a chromatographic sorbent. Chitosan modified with benzenic ring (CH-Bz) was used to separate two flavonoids, swertisin and 2"-O-rhamnosylswertisin, from ethyl acetate fraction of Aleurites moluccana. The results showed that CH-Bz can be used as a sorbent for the separation of flavonoid compounds. The studies showed that CH-Bz in column chromatography produces goods results, separation of the flavonoid compounds.

  6. Flow Injection Analysis of Mercury Using 4-(Dimethylamino Benzaldehyde-4-Ethylthiosemicarbazone as the Ionophore of a Coated Wire Electrode

    Directory of Open Access Journals (Sweden)

    Sulaiman Ab Ghani

    2012-11-01

    Full Text Available A flow injection analysis (FIA incorporating a thiosemicarbazone-based coated wire electrode (CWE was developed method for the determination of mercury(II. A 0.1 M KNO3 carrier stream with pH between 1 and 5 and flow rate of 1 mL·min−1 were used as optimum parameters. A linear plot within the concentration range of 5 × 10−6–0.1 M Hg(II, slope of 27.8 ± 1 mV per decade and correlation coefficient (R2 of 0.984 were obtained. The system was successfully applied for the determination of mercury(II in dental amalgam solutions and spiked environmental water samples. Highly reproducible measurements with relative standard deviation (RSD < 1% (n = 3 were obtained, giving a typical throughput of 30 samples·h−1.

  7. 21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

    Science.gov (United States)

    2010-04-01

    ... acid (equisetic acid, citridic acid, achilleic acid). Anethole (parapropenyl anisole). Benzaldehyde.... Methyl anthranilate (methyl-2-aminobenzoate). Piperonal (3,4-methylenedioxy-benzaldehyde,...

  8. Antimicrobial Activity and Urease Inhibition of Schiff Bases Derived from Isoniazid and Fluorinated Benzaldehydes and of Their Copper(II Complexes

    Directory of Open Access Journals (Sweden)

    Ladislav Habala

    2016-12-01

    Full Text Available In order to evaluate the influence of substitution on biological properties of Schiff bases and their metal complexes, a series of differently substituted fluorine-containing Schiff bases starting from the drug isoniazid (isonicotinylhydrazide were prepared and their structures were established by single-crystal X-ray diffraction. Also, four copper(II complexes of these Schiff bases were synthesized. The prepared compounds were evaluated for their antimicrobial activity and urease inhibition. Two of the Schiff bases exerted activity against C. albicans. All copper(II complexes showed excellent inhibitory properties against jack bean urease, considerably better than that of the standard inhibitor acetohydroxamic acid.

  9. Antimicrobial Activity and Urease Inhibition of Schiff Bases Derived from Isoniazid and Fluorinated Benzaldehydes and of Their Copper(II) Complexes.

    Science.gov (United States)

    Habala, Ladislav; Varényi, Samuel; Bilková, Andrea; Herich, Peter; Valentová, Jindra; Kožíšek, Jozef; Devínsky, Ferdinand

    2016-12-17

    In order to evaluate the influence of substitution on biological properties of Schiff bases and their metal complexes, a series of differently substituted fluorine-containing Schiff bases starting from the drug isoniazid (isonicotinylhydrazide) were prepared and their structures were established by single-crystal X-ray diffraction. Also, four copper(II) complexes of these Schiff bases were synthesized. The prepared compounds were evaluated for their antimicrobial activity and urease inhibition. Two of the Schiff bases exerted activity against C. albicans. All copper(II) complexes showed excellent inhibitory properties against jack bean urease, considerably better than that of the standard inhibitor acetohydroxamic acid.

  10. A study on the condensation reaction of aryl substituted 4-amine-1,2,4-triazole with benzaldehydes: Structures and spectroscopic properties of schiff bases and stable hemiaminals

    Science.gov (United States)

    Wajda-Hermanowicz, Katarzyna; Pieniążczak, Damian; Wróbel, Robert; Zatajska, Aleksandra; Ciunik, Zbigniew; Berski, Sławomir

    2016-06-01

    A series of stable hemiaminals and Schiff bases containing 3,5-disubstituted 1,2,4-triazole derivatives were synthesized. The structure of the prepared compounds was confirmed by means of 1H NMR, 13C NMR, IR, MS and elemental analysis. The steric and electronic effects of the triazole ring substituents on the hemiaminal formation was also discussed. Single crystal X-ray diffraction studies of hemiaminals obtained from 4-amino-3,5-dipyridyn-2-yl-1,2,4- triazole (4, 5) revealed the formation of centrosymmetric dimers linked by strong O-H … .N1Tr hydrogen bonds. The Schiff bases obtained from the unsymmetrical 3-methyl,5-phenyl-1,2,4-triazole was found to be a different E-conformer which was determined through solution NMR and crystallographic diffraction analysis (13). The molecular geometry of the unsymmetrical triazole derivatives: hemiaminal (12) and Schiff base (13) were also optimized using density functional theory (DFT/M062x) method with the 6-311++G (d,p) basis set in ground state and compared with the experimental data.

  11. Synthesis of Some New Anils: Part 1. Reaction of 2-Hydroxy-benzaldehyde and 2-Hydroxynaphthaldehyde with 2-Aminopyridene and 2-Aminopyrazine

    Directory of Open Access Journals (Sweden)

    Khadija O. Badahdah

    2007-08-01

    Full Text Available New Schiff bases derived from 2-aminopyridene and 2-aminopyrazine have been synthesized. The UV-Visible spectra of the compounds have been investigated in acetonitrile and toluene. The compounds were in tautomeric equilibrium (enol-imine O– H···N, keto-amine O···H–N forms in polar and nonpolar solvents. For some derivatives the keto-amine form was observed in both toluene and acetonitrile. 1H-NMR and IR results showed that all Schiff bases studied favor the enol-imine form over the keto form in a weakly polar solvent such as deuterochloroform.

  12. Electrochemical and theoretical investigation of the inhibitory effect of two Schiff bases of benzaldehyde for the corrosion of aluminium in hydrochloric acid

    Science.gov (United States)

    Naik, U. J.; Jha, P. C.; Lone, M. Y.; Shah, R. R.; Shah, N. K.

    2016-12-01

    The corrosion inhibition effect of o-Aminophenol-N-Benzylidene (o-AmphNB) and o-Anisidene-N-Benzylidene (o-AnsNB) for pure Aluminium in 1 M HCl at different concentrations of two different inhibitors were investigated by means of weight loss, potentiodynamic polarization and electrochemical impedance spectroscopy (EIS). The values of Δ Gadso revealed that the adsorption mechanism of these molecules on aluminium surface is competitive phenomenon between chemical and physical adsorption. Potentiodynamic polarization parameters revealed the mixed mode of inhibition with predominance of cathodic inhibition. The impedance results showed that with increase in concentration of inhibitor, charge transfer resistance increases while double layer capacitance decreases. Quantum chemical calculations based on density functional theory (DFT) method were performed on o-AmphNB and o-AnsNB to determine the relationship between molecular structures and their inhibition efficiencies. Correlation analysis concluded that the inhibition effect of inhibitors could be explained in terms of electronic properties.

  13. Fast and catalyst-free hydrazone ligation via ortho-halo-substituted benzaldehydes for protein C-terminal labeling at neutral pH.

    Science.gov (United States)

    Xu, Yang; Xu, Ling; Xia, Yuan; Guan, Chao-Jian; Guo, Qing-Xiang; Fu, Yao; Wang, Chen; Li, Yi-Ming

    2015-08-28

    Rapid and catalyst-free hydrazone ligation reaction between ortho-halobenzaldehyde derivatives and peptide/protein hydrazides was observed at neutral pH and room temperature. 2-Chlorobenzaldehyde exhibited the fastest reaction and highest conversion rates among the series of ortho-halobenzaldehydes. The resulting hydrazone-containing bioconjugation products were also found to be fairly stable under experimental conditions. The new ligation strategy was successfully used for protein C-terminal labeling and should provide a practical approach for the modification of proteins.

  14. Evaluation of DNA-binding, DNA cleavage, antioxidant and cytotoxic activity of mononuclear ruthenium(II) carbonyl complexes of benzaldehyde 4-phenyl-3-thiosemicarbazones

    Science.gov (United States)

    Sampath, Krishnan; Sathiyaraj, Subbaiyan; Jayabalakrishnan, Chinnasamy

    2013-11-01

    Two 4-phenyl-3-thiosemicarbazone ligands, (E)-2-(2-chlorobenzylidene)-N-phenylhydrazinecarbothioamide (HL1) and (E)-2-(2-nitrobenzylidene)-N-phenylhydrazinecarbothioamide (HL2), and its ruthenium(II) complexes were synthesized and characterized by physico-chemical and spectroscopic methods. The Schiff bases act as bidentate, monobasic chelating ligands with S and N as the donor sites and are preferably found in the thiol form in all the complexes studied. The molecular structure of HL1 and HL2 were determined by single crystal X-ray diffraction method. DNA binding of the compounds was investigated by absorption spectroscopy which indicated that the compounds bind to DNA via intercalation. The oxidative cleavage of the complexes with CT-DNA inferred that the effects of cleavage are dose dependent. Antioxidant study of the ligands and complexes showed significant antioxidant activity against DPPH radical. In addition, the in vitro cytotoxicity of the ligands and complexes assayed against HeLa and MCF-7 cell lines showed higher cytotoxic activity with the lower IC50 values indicating their efficiency in killing the cancer cells even at low concentrations.

  15. Mixed ligand ruthenium(III) complexes of benzaldehyde 4-methyl-3-thiosemicarbazones with triphenylphosphine/triphenylarsine co-ligands: Synthesis, DNA binding, DNA cleavage, antioxidative and cytotoxic activity

    Science.gov (United States)

    Sampath, K.; Sathiyaraj, S.; Raja, G.; Jayabalakrishnan, C.

    2013-08-01

    The new ruthenium(III) complexes with 4-methyl-3-thiosemicarbazone ligands, (E)-2-(2-chlorobenzylidene)-N-methylhydrazinecarbothioamide (HL1) and (E)-2-(2-nitrobenzylidene)-N-methylhydrazinecarbothioamide (HL2), were prepared and characterized by various physico-chemical and spectroscopic methods. The title compounds act as bidentate, monobasic chelating ligands with S and N as the donor sites and are preferably found in the thiol form in all the complexes studied. The molecular structure of HL1 and HL2 were determined by single crystal X-ray diffraction method. DNA binding of the ligands and complexes were investigated by absorption spectroscopy and IR spectroscopy. It reveals that the compounds bind to nitrogenous bases of DNA via intercalation. The oxidative cleavage of the complexes with CT-DNA inferred that the effects of cleavage are dose dependent. Antioxidant study of the ligands and complexes showed the significant antioxidant activity against DPPH radical. In addition, the in vitro cytotoxicity of the ligands and complexes against MCF-7 cell line was assayed which showed higher cytotoxic activity with the lower IC50 values indicating their efficiency in killing the cancer cells even at low concentrations.

  16. 孜然种子提取物枯茗醛和枯茗酸抑菌作用研究%Inhibition of p-isopropyl Benzaldehyde and p-isopropyl Benzoic Acid extracted from Cuminum cyminum against Plant Pathogens

    Institute of Scientific and Technical Information of China (English)

    胡林峰; 陈从珍; 易晓华; 冯俊涛; 张兴

    2008-01-01

    以番茄早疫病菌、棉花黄萎病菌、小麦纹枯病菌、烟草赤星病菌、小麦全蚀病菌、油菜菌核病菌、辣椒疫霉病菌、水稻纹枯病菌、小麦白粉病菌和番茄灰霉病菌等为供试菌种,采用离体与活体相结合的方法系统地测定了枯茗醛和枯茗酸的抑菌活性.离体抑菌活性测定结果表明,枯茗醛和枯茗酸对多种病原菌具有一定的抑制效果,其中对油菜菌核病菌菌丝生长的抑制效果高于其它供试病原菌,有效中浓(EC50)分别为2.1和7.3 mg/L;枯茗醛和枯茗酸对小麦白粉病的防治实验结果表明,供试浓度为1 000 mg/L时,两种药剂的保护防效均高于50%;相同处理浓度下,枯茗酸对油菜菌核病的保护防效与速克灵处理相当,达到57.52%.

  17. 有机介质中固定化面包酵母催化苯甲醛加氢反应%Studies on catalytic hydrogenation of benzaldehyde with immobilized baker's yeast in organic solvents

    Institute of Scientific and Technical Information of China (English)

    钟春龙; 梅乐和; 胡方敏; 姚善泾

    2007-01-01

    研究了活化时间、摇床转速、缓冲液的pH值、反应温度等因素对海藻酸钙固定化面包酵母在有机介质中催化苯甲醛加氢生成苯甲醇的反应活性的影响,并对固定化酵母的重复利用性进行了探讨.结果表明,在pH为10的缓冲液中制备的固定化面包酵母的催化加氢能力最强;活化时间对催化加氢能力有较大的影响;在不同的有机溶剂中,最适的反应温度也不同.

  18. β-环糊精微反应器中苯甲醇氧化制备苯甲醛%Preparation of Benzaldehyde Through Oxidation of Benzyl Alcohol in Microreactor of β-Cyclodextrin

    Institute of Scientific and Technical Information of China (English)

    于红杰; 兰支利; 尹笃林; 欧建雄

    2008-01-01

    以β-环糊精为微反应器,用NBS作为氧化剂,能有效进行催化苯甲醇氧化制备苯甲醛.实验结果表明,β-环糊精微反应器中一锅法合成苯甲醛,具有反应条件温和、无环境污染、操作简单、用水作为溶剂、环糊精可以循环使用等优点.在反应温度为25℃,反应时间为10 h,β-环糊精、苯甲醇、NBS的摩尔比为2:1:2时,苯甲醛的产率可达83.7%.

  19. 固载杂多酸树脂催化合成苯甲醛正己硫醇缩醛香料%Synthesis of Benzaldehyde Hexyl Mercaptal Spice on Supported Heteropoly Acid Catalyst

    Institute of Scientific and Technical Information of China (English)

    聂国朝

    2003-01-01

    以离子交换树脂固载磷钨酸为催化剂合成了苯甲醛正己硫醇缩醛,考察了影响收率的因素.其最优条件为:苯甲醛∶正己硫醇∶催化剂∶二氯甲烷=1mol∶2.15mol∶20g∶350ml,43℃回流下进行,反应时间5.0h,收率可达86.3%,催化剂可重复使用.

  20. Synthesis of benzaldehyde hexyl mercaptal spice on supported heteropolyacid catalyst%固载杂多酸树脂催化合成苯甲醛正己硫醇缩醛

    Institute of Scientific and Technical Information of China (English)

    聂国朝

    2003-01-01

    以离子交换树脂固载磷钨酸为催化剂合成了苯甲醛正己硫醇缩醛.在考察了各种影响收率因素的基础上,得出最优工艺条件为:n(苯甲醛)∶n(正己硫醇)∶m(催化剂)∶V(二氯甲烷)=1 mol∶2.15 mol∶20 g∶350 ml,43 ℃,回流,反应时间5.0 h.在此条件下收率可达86.3%.催化剂可重复使用.

  1. Synthesis, spectral characterization of biologically active compounds derived from oxalyldihydrazide and 5-tert-Butyl-2-hydroxy-3-(3-phenylpent-3-yl benzaldehyde and their Cu(II, Ni(II and Co(II Complexes

    Directory of Open Access Journals (Sweden)

    Rajeev Johari

    2011-02-01

    Full Text Available A series of Schiff base M(II complexes of the type [HLMClH2O] and [HLMOAcH2O], where M =Cu(II, Ni(II and Co(II have been synthesized by condensation of 3-tert-butl-2-hydroxy-3-(3-phenylpent-3-ylbenzaldehyde and oxalyldihydrazide (2:1 in the presence of divalent metal salt in methanolic medium. Thecomplexes have been characterized with the help of elemental analysis, conductance measurements, magneticmeasurements and their structural configuration have been determined by various spectroscopic (electronic, IR,1H NMR, 13C NMR, GCMS techniques. Electronic and magnetic moments of the complexes indicate that thegeometries of the metal centers were octahedral. These metal complexes were also tested for their antimicrobialactivities to assess their inhibiting potential.

  2. Experimental Determination and Modeling of the Phase Behavior for the Selective Oxidation of Benzyl Alcohol in Supercritical CO2

    DEFF Research Database (Denmark)

    Tsivintzelis, Ioannis; Beier, Matthias Josef; Grunwaldt, Jan-Dierk

    2011-01-01

    In this study the phase behavior of mixtures relevant to the selective catalytic oxidation of benzyl alcohol to benzaldehyde by molecular oxygen in supercritical CO2 is investigated. Initially, the solubility of N2 in benzaldehyde as well as the dew points of CO2–benzyl alcohol–O2 and CO2...

  3. Photosensitive Polymers for Liquid Crystal Alignment

    Science.gov (United States)

    Mahilny, U. V.; Stankevich, A. I.; Trofimova, A. V.; Muravsky, A. A.; Murauski, A. A.

    The peculiarities of alignment of liquid crystal (LC) materials by the layers of photocrosslinkable polymers with side benzaldehyde groups are considered. The investigation of mechanism of photostimulated alignment by rubbed benzaldehyde layer is performed. The methods of creation of multidomain aligning layers on the basis of photostimulated rubbing alignment are described.

  4. An Efficient Method For The One-Pot, Four-Component Benzaldehyde Based Synthesis of 3-Methyl-1,4-Diphenyl-7,8-Dihydro-1H-Furo[3,4-E]Pyrazolo[3,4-B]Pyridin-5(4H-Ones Catalyzed by Alum in Environment-Friendly Media.

    Directory of Open Access Journals (Sweden)

    Sadif A. Shirvan

    2014-03-01

    Full Text Available A mild and efficient method for the synthesis of 3-methyl-1,4- diphenyl-7,8-dihydro-1H-furo[3,4-e]pyrazolo[3,4-b]pyridin-5(4H-one derivatives via one-pot, four-component reaction of aromatic aldehydes, tetronic acid, 3-aminobut-2-enenitrile, and phenylhydrazine is described using Alum as catalyst. The features of this procedure are mild reaction conditions, excellent yields, short reaction time, and operational simplicity.

  5. EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF); Scientific Opinion on Flavouring Group Evaluation 20, Revision 3 (FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30

    DEFF Research Database (Denmark)

    Larsen, John Christian; Nørby, Karin Kristiane; Beltoft, Vibe Meister;

    The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to consider in this revision 3 of Flavouring Group Evaluation 20, the SCF Opinion on benzoic acid. Furthermore information on stereoisomeric composition for two substa...

  6. Preparation of soluble and insoluble polymer supported IBX reagents.

    Science.gov (United States)

    Reed, Neal N; Delgado, Mercedes; Hereford, Kristina; Clapham, Bruce; Janda, Kim D

    2002-08-05

    A series of soluble and insoluble polymer supported versions of the versatile oxidizing reagent IBX has been prepared. Each of the reagents were evaluated for their efficiency in the conversion of benzyl alcohol to benzaldehyde. Results from this study were that the soluble, non-crosslinked polystyrene supported IBX reagent gave the best rate of conversion to benzaldehyde, while the macroporous polymer supported IBX resin provided a superior rate of conversion to benzaldehyde when compared with a gel type resin. The macroporous IBX reagent was also shown to convert a series of alcohols to the corresponding aldehydes and ketones.

  7. Photocatalytic oxidation of primary and secondary benzyl alcohol catalyzed by two coenzyme NAD+ models

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Photocatalytic oxidation of primary and secondary benzyl alcohol to corresponding benzaldehyde or acetophenone using Acr+ClO4- or PhAcr+ClO4- as photocatalysts under visible light irradiation at room temperature.

  8. A Rapid and Efficient Synthesis of 2, 4, 6-Triarylpyridines under Microwave Irradiation

    Institute of Scientific and Technical Information of China (English)

    Xian Qiang HUANG; Hong Xia LI; Jin Xian WANG; Xue Feng JIA

    2005-01-01

    An rapid and efficient synthesis of 2, 4, 6-triarylpyridines is reported using substituted benzaldehydes, substituted acetophenones and ammonia as starting materials under microwave irradiation in the presence of PEG-400.

  9. A concise total synthesis of (R)-fluoxetine, a potent and selective serotonin reuptake inhibitor

    Energy Technology Data Exchange (ETDEWEB)

    Fatima, Angelo de; Lapis, Alexandre Augusto M.; Pilli, Ronaldo A. [Universidade Estadual de Campinas, SP (Brazil). Inst. de Quimica]. E-mail: pilli@iqm.unicamp.br

    2005-05-15

    (R)-Fluoxetine, potent and selective serotonin reuptake inhibitor, has been synthesized in six steps, 50% overall yield and 99% ee from benzaldehyde via catalytic asymmetric allylation with Maruoka's catalyst. (author)

  10. Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid Receptors and Cannabinoid Receptors from the Fungus Eurotium repens

    Science.gov (United States)

    Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two benzyl derivatives, repenol A (1) and repenol B (2). Seven known secondary metabolites were also isolated including five benzaldehyde compounds, flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglauci...

  11. Texture of semi-solids : sensory flavor-texture interactions for custard desserts

    NARCIS (Netherlands)

    Wijk, de R.A.; Rasing, F.; Wilkinson, C.L.

    2003-01-01

    Possible interactions between flavor and oral texture sensations were investigated for four flavorants, diacetyl, benzaldehyde, vanillin, and caffeine, added in two concentrations to model vanilla custard desserts. The flavorants affected viscosities and resulted in corresponding changes in perceive

  12. The First Total Synthesis of Isoliquiritin

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A first total synthesis of isoliquiritin was accomplished starting from p-hydroxy- benzaldehyde and 2,4-dihydroxyacetylphenone. The key step is condensation reaction. In synthetic process need not protect the hydroxy group of reacting substance.

  13. The mechanism for the rhodium-catalyzed decarbonylation of aldehydes: A combined experimental and theoretical study

    DEFF Research Database (Denmark)

    Fristrup, Peter; Kreis, Michael; Palmelund, Anders;

    2008-01-01

    The mechanism for the rhodium-catalyzed decarbonylation of aldehydes was investigated by experimental techniques (Hammett studies and kinetic isotope effects) and extended by a computational study (DFT calculations). For both benzaldehyde and phenyl acetaldehyde derivatives, linear Hammett plots ...

  14. Synthesis and Catalytic Activity of Two New Cyclic Tetraaza Ligands

    Directory of Open Access Journals (Sweden)

    Burkhard König

    2003-05-01

    Full Text Available Two new chiral cyclic tetraaza ligands were synthesized and characterized. Their catalytic activity was tested in the asymmetric addition of diethylzinc to benzaldehyde. The expected secondary alcohol was obtained in moderate yields, but with very low enantioselectivity.

  15. A Convenient and Efficient Procedure for Oxime Ethers

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    Acetophenone oxime and benzaldehyde oxime were converted to oxime ethers in the presence of alkyl halide or methyl sulfate and KOH in aqueous DMSO in 5 to 70 min. The yields of oxime ethers were 70 - 96%.

  16. A Convenient and Efficient Procedure fox Oxime Ethers

    Institute of Scientific and Technical Information of China (English)

    ChunBaoLI; MichaelC.K.CHOI; 等

    2002-01-01

    Acetophenone oxime and benzaldehyde oxime were converted to oxime ethers in the presence of alkyl halide or methyl sulfate and KOH in aqueous DMSO in 5 to 70 min. The yields of oxime ethers were 70-96%.

  17. A Sequential Preparation of Organic Compounds for Senior Chemistry Classes

    Science.gov (United States)

    Merrigan, Cecilia; Crotty, Patricia

    1971-01-01

    Describes procedures suitable for student preparation of benzaldehyde, benzoic acid, and ethyl benzoate sequentially from benzyl alcohol. Preparation for benzyl chloride also given. All reagents except benzyl alcohol are common inorganic chemicals. (AL)

  18. A Novel NADPH-Dependent Aldehyde Reductase Gene from Saccharomyces cerevisiae NRRL Y-12632 Involved in the Detoxification of Aldehyde Inhibitors Derived from Lignocellulosic Biomass Conversion

    Science.gov (United States)

    Aldehyde inhibitors such as furfural, 5-hydroxymethylfurfural (HMF), anisaldehyde, benzaldehyde, cinnamaldehyde, and phenylaldehyde are commonly generated during lignocellulosic biomass conversion process for low-cost cellulosic ethanol production that interferes with subsequent microbial growth and...

  19. Synthesis of 1, 4-Dihydropyridine Derivatives using FeCl3 as Catalyst under Solvent-free Condition

    Directory of Open Access Journals (Sweden)

    ABDORRAHMAN KEYHANI

    2013-06-01

    Full Text Available A mixture of ethyl acetoacetate, benzaldehyde and ammonium acetate and in the presence of FeCl3 under solvent-free condition were converted to 1, 4-dihydropyridines with good yields.

  20. Physicochemical Investigations of Th(IV and UO2(VI Complexes with New Schiff Bases Along with their Toxic Effects

    Directory of Open Access Journals (Sweden)

    Sonal Agnihotri

    2010-01-01

    Full Text Available Schiff bases were obtained using p-trimethoxy benzaldehyde, p-hydroxyl benzaldehyde and 2-amino pyridine to prepare new complexes of thorium(IV and dioxouranium(VI metals by various anions. The synthesized ligands and complexes were analytically studied through spectral studies, elemental analysis conductance measurements along with semi empirical and thermogravimetric methods. The complexes were assigned various coordination numbers ranging from 6-10 on the basis of these studies.

  1. Two expedient ‘one-pot’ methods for synthesis of -aryl--mercaptoketones over anhydrous potassium carbonate or amberlyst-15 catalyst

    Indian Academy of Sciences (India)

    Chayan Guha; Rina Mondal; Rammohan Pal; Asok K Mallik

    2013-11-01

    Two expedient one-pot methods have been developed for synthesis of -aryl--mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve microwave irradiation (5min) of 1:1 mixtures of acetophenones and benzaldehydes over neutral alumina supported anhydrous potassium carbonate or amberlyst-15 in the first step, and that is followed by addition of thiol to the resulting material and keeping at room temperature for 1.5 h.

  2. Synthesis and Antibacterial Activity of Some Transition Metal Complexes of Oxime, Semicarbazone and Phenylhydrazone

    Directory of Open Access Journals (Sweden)

    Majed M. Hania

    2009-01-01

    Full Text Available Co, Ni and Cu complexes have been prepared by reacting metal chloride with 4-chlorobenzaldehyde oxime, 4-methylbenzaldehyde oxime, 4-nitrobenzaldehyde oxime, 4-chlorobenzaldehyde semicarbazone, 4-methyl- benzaldehyde semicarbazone, 4-nitrobenzaldehyde semicarbazone, 4-chloro benzaldehyde phenylhydrazone, 4-methylbenzaldehyde phenyl hydrazone and 4-nitrobenzaldehyde phenylhydrazone and their antibacterial activity have been studied and compared with their ligands against E. coli which gave significant results of activity.

  3. Influence of Formazan Derivatives on Corrosion Inhibition of Mild Steel in Hydrochloric Acid Medium

    OpenAIRE

    Venkatesan, P.; Anand, B.; P. Matheswaran

    2009-01-01

    Formazan of benzaldehyde (FB) and formazan of p-dimethyl amino benzaldehyde (FD) were synthesized. These compounds were studied as corrosion inhibitor for mild steel in 1.11 N hydrochloric acid by weight loss method. The result showed that the corrosion inhibition efficiency of these compounds was found to vary with the temperature and acid concentration. Also, it was found that the corrosion inhibition behaviour of FD is greater than that of FB. The kinetic treatment of the results gave firs...

  4. Influence of Electronic Factors on “Solvent-Free and Catalyst-Free Biginelli Reaction

    Directory of Open Access Journals (Sweden)

    Tanay Pramanik

    2013-12-01

    Full Text Available A series of Biginelli condensation were carried out employing urea, ethyl acetoacetate with a series of different derivatives of benzaldehyde. A green synthetic procedure was followed for performing the Biginelli reactions. The reaction conditions were found to be different for electron rich and electron deficient benzaldehydes. So the electronic effect has shown a significant impact on the reaction condition of the Biginelli condensation.

  5. Technical communications

    Energy Technology Data Exchange (ETDEWEB)

    Krueger, D.A.

    Bitter almond oil (benzaldehyde), a flavoring compound used in many foods, was isolated from apricot kernels; 2 synthetic benzaldehyde samples were obtained from commercial sources. All samples were analyzed for radiocarbon (/sup 14/C) content. The natural sample yielded a value consistent with its natural origin (approximately 116% of Modern Standard Activity), while the synthetic samples were devoid of /sup 14/C activity as expected for a petrochemical material. Implications for quality control of bitter almond oil are discussed.

  6. Síntese e hidrólise de azalactonas de Erlenmeyer-Plöchl mediadas por radiação micro-ondas em aparelhos doméstico e dedicado: experimentos de química orgânica para a graduação Synthesis and hydrolysis of Erlenmeyer-Plöchl azalactones mediated by microwave radiation in domestic and dedicated ovens: undergraduate organic chemistry experiments

    Directory of Open Access Journals (Sweden)

    Silvio Cunha

    2013-01-01

    Full Text Available This work describes a green chemistry experiment for the synthesis of Erlenmeyer-Plöchl azalactones mediated by microwave irradiation, employing both dedicated and domestic equipment. Hippuric acid was reacted with equimolar amounts of benzaldehyde, p-chloro-benzaldehyde or p-N,N-dimethyl-benzaldehyde in acetic anhydride as the solvent. Acid hydrolysis of obtained 4-benzylidene-2-phenyloxazol-5(4H-one under microwave and convectional heating afforded Z-α-(benzoylaminocinnamic acid at a 51-61.5% yield. The UV-Vis molecular spectra of 4-benzylidene-2-phenyloxazol-5(4H-one and 4-(4'-N,N-dimethylbenzylidene-2-phenyloxazol-5(4H-one were obtained in ethanol, CH2Cl2 and DMSO and bathochromic shift was observed for the latter azalactone.

  7. The effects of the cherry variety on the chemical and sensorial characteristics of cherry brandy

    Directory of Open Access Journals (Sweden)

    NINOSLAV NIKIĆEVIĆ

    2011-09-01

    Full Text Available The chemical and sensorial characteristics of cherry brandy produced from five cherry varieties (Oblacinska, Celery’s 16, Rexle, Heiman’s Ruby and Heiman’s Conserve grown in Serbia were studied. Gas chromatography and gas chromatography–mass spectrometry analysis of these distillates led to the identification of 32 components, including 20 esters, benzaldehyde, 6 terpenes and 5 acids. The ethyl esters of C8–C18 acids were the most abundant in all samples. The benzaldehyde content was quantified by high performance liquid chromatography with UV detection. The average benzaldehyde concentration in the samples ranged between 2.1 and 24.1 mg L-1. The total sensory scores of the cherry brandies ranged between 17.30 to 18.05, with the cherry brandy produced from the Celery’s 16 variety receiving the highest score (18.05.

  8. [Health effect of volatile aldehyde compounds in photocatalytic oxidation of aromatics compounds].

    Science.gov (United States)

    Zhao, Wei-rong; Liao, Qiu-wen; Yang, Ya-nan; Dai, Jiu-song

    2013-05-01

    Photocatalytic oxidation (PCO) of toluene and benzaldehyde in indoor air by N doped TiO2 (N-TiO2) was conducted under UV irradiation of 254 nm. The intermediates were identified and monitored on real-time by proton transfer reaction-mass spectrometry. The health risks of PCO of toluene and benzaldehyde were assessed based on health risk influence index (eta). Results indicated that both the conversion rate and mineralization rate of toluene and benzaldehyde were relatively high, however, the volatile aldehyde compounds (VAs), including acetaldehyde and formaldehyde generated from ring-opening, significantly influenced the health risks of PCO of toluene and benzaldehyde. Acetaldehyde played a crucial role on health risks, which was inclined to desorb from the surface of catalysts, accumulate in gas-phase, and increase the health risks of PCO of the aromatic compounds. The concentration of formaldehyde kept stable at a relatively low level, however its impact cannot be neglected. In the PCO process of toluene and benzaldehyde, eta reached the maximum values of 8 499.68 and 21.43, with the eta(VAs), contribution of VAs to the health risk influence index of outlet, reaching 99.3% and 98.3%, respectively. The average values of eta in the PCO process of 30 min were 932.86 and 8.52, and for which eta(VAs), reached 98.5% and 98.0%, respectively. When PCO of toluene and benzaldehyde reached steady state, eta were 236.09 and 2.30, and eta(VAs) reached 97.9% and 97.8%, respectively. Hence, eta(VAs), can be taken as a characteristic parameter in assessment of health risks of PCO of aromatic compounds.

  9. Solvent-free Synthesis of Flavanone over New Hybrid Mesoporous Base Catalysts

    Institute of Scientific and Technical Information of China (English)

    WANG Hui; NIU Xiao-di; ZHAO Min; XIAO Xue-bin; WANG Hong-su; WANG Zhong-dong

    2011-01-01

    Benzyl and anthracenemethyl groups were respectively bonded to the N atoms of 3-aminopropyl functionalized mesoporous SBA-15(APS-SBA-15) to obtain two new base catalysts over which the condensation reaction of benzaldehyde and 2′-hydroxyacetophenone was studied.Good catalytic activities and high selectivities for flavanones were obtained in solvent-free reactions,which is attributed to the effect of benzyl and anthracenemetyl groups on the base sites of catalysts and the steric hindrance of futher reaction of flavanone with benzaldehyde.

  10. Condensação de Knoevenagel de aldeídos aromáticos com o ácido de Meldrum em água: uma aula experimental de Química Orgânica Verde

    Directory of Open Access Journals (Sweden)

    Silvio Cunha

    2012-01-01

    Full Text Available This work describes an undergraduate experiment for the synthesis of Knoevenagel adduct of Meldrum's acid with nine aromatic aldehydes, using water as the solvent, in an adaptation of a previously reported synthetic protocol. The synthesis was straightforward, requiring a period of two hours, and is suitable for undergraduate experimental courses on green chemistry. In addition, quantitative analyses of the relative reactivity of p-nitro-benzaldehyde and p-metoxi-benzaldehyde was evaluated through the competitive reaction of equimolar amounts of these aldehydes with one equivalent of Meldrum's acid, using gas chromatography to quantify the composition of the reaction mixture.

  11. Novel synthesis of substituted benzylidenecyclohexanone by microwave assisted organic synthesis

    Science.gov (United States)

    Handayani, Sri; Budimarwanti, Cornelia; Haryadi, Winarto

    2017-03-01

    Benzylidenecyclohexanone derivatives are compounds with wide bioactivity. Usually, it was synthesized from cyclohexanones and benzaldehyde derivatives under base condition. This research presents a rapid and simple method to synthesis substituted benzylidenecyclohexanone. Cyclohexanone was mixed with 4-hydroxybenzaldehyde in acid condition under MAOS for 2 minutes, then it was left to cooled. Brownish purple powder in 81.47% yield was obtained. The product was identified by gas chromatography, then followed by structure elucidation by using NMR spectrophotometer. The novel compound is confirmed as 4-((E)-((1E,3'E)-3'-(4-hydroxybenzylidene)-2'-oxo-[1,1'-bi(cyclohexylidene)]-2,5-dienylidene-4-ylidene) me-thoxy)benzaldehyde.

  12. Influence of Formazan Derivatives on Corrosion Inhibition of Mild Steel in Hydrochloric Acid Medium

    Directory of Open Access Journals (Sweden)

    P. Venkatesan

    2009-01-01

    Full Text Available Formazan of benzaldehyde (FB and formazan of p-dimethyl amino benzaldehyde (FD were synthesized. These compounds were studied as corrosion inhibitor for mild steel in 1.11 N hydrochloric acid by weight loss method. The result showed that the corrosion inhibition efficiency of these compounds was found to vary with the temperature and acid concentration. Also, it was found that the corrosion inhibition behaviour of FD is greater than that of FB. The kinetic treatment of the results gave first order kinetics. The relative corrosion inhibition efficiency of these compounds has been explained on the basis of structure dependent - electron donor properties of the inhibitors.

  13. Solid-phase synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines by stereoselective intramolecular N-carbamyliminium Pictet-Spengler reactions

    DEFF Research Database (Denmark)

    Diness, Frederik; Meldal, Morten

    2006-01-01

    converts into Pictet-Spengler-type products with a variety of C-nucleophiles. Amino aldehydes masked with 3-Boc-(1,3)-oxazinane (Box) have been synthesized from amino acids, amino alcohols, or 2-nitro benzaldehydes. The amino moiety of these masked aldehydes has been converted into pentafluorophenyl...... of other aromatic C-nucleophiles, including substituted indoles, benzenes, pyrene, furan, thiophenes, and benzothiophene with comparable stereoselectivity and purity. Prolonged exposure of the benzaldehyde-derived Pictet-Spengler products to strong acid and air lead to quantitative auto-oxidation which...

  14. A new approach for the preparation of well-defined Rh and Pt nanoparticles stabilized by phosphine-functionalized silica for selective hydrogenation reactions.

    Science.gov (United States)

    Llop Castelbou, J; Szeto, K C; Barakat, W; Merle, N; Godard, C; Taoufik, M; Claver, C

    2017-03-18

    In this work, a new methodology for the synthesis of well-defined metallic nanoparticles supported on silica is described. This methodology is based on the surface control provided by SOMC. The nanoparticles are formed via the organometallic approach and are catalytically active in the hydrogenation of p-xylene, 3-hexyne, 4-phenyl-2 butanone, benzaldehyde, and furfural.

  15. A New Iterative Approach for the Synthesis of Oligo(phenyleneethynediyl) Derivatives and Its Application for the Preparation of Fullerene-Oligo(phenyleneethynediyl) Conjugates as Active Photovoltaic Materials

    NARCIS (Netherlands)

    Nierengarten, Jean-François; Gu, Tao; Hadziioannou, Georges; Tsamouras, Dimitris; Krasnikov, Victor

    2004-01-01

    Disymmetrically substituted oligo(phenyleneethynediyl) (OPE) derivatives were prepared from 2,5-bis(octyloxy)-4-[(triisopropylsilyl)ethynyl]benzaldehyde (5) by an iterative approach using the following reaction sequence: i) Corey-Fuchs dibromoolefination, ii) treatment with an excess of lithium diis

  16. Synthesis and Biological Activities of Substituted Triazolethione Schiff Base

    Institute of Scientific and Technical Information of China (English)

    SUN, Xiao-Hong; TAO, Yan; LIU, Yuan-Fa; CHEN, Bang

    2007-01-01

    Six novel Schiff bases have been synthesized by the condensation reaction of 4-amino-5-(4-pyridyl)-2,4-dihydro-1,2,4-triazole-3-thione with various benzaldehydes. The structures of the compounds have been confirmed by 1H NMR, IR and elemental analysis. The preliminary bioassay indicated that the title compounds possessed good fungicidal activities to several vegetable pathogens.

  17. Synthesis and Catalytic Application of Chiral 1, 1'-Binaphthyl Polymers

    Institute of Scientific and Technical Information of China (English)

    Xu Dong LIU; Meng Xian DING; Lian Xun GAO

    2004-01-01

    The synthesis of a new type of polymers with main chain chirality based on BINOL skeleton is described. Titanium-BINOLate catalysts are easily generated from these polymers and applied to the asymmetric reaction of Et2Zn with benzaldehyde. The products are obtained in good yields with moderate enantioselectivities.

  18. Dye laser. Farbstofflaser

    Energy Technology Data Exchange (ETDEWEB)

    Telle, H.; Schieder, R.; Raue, R.; Eckstein, U.

    1987-02-12

    For a laser radiating in the range of wavelengths from 420 to 480 nm dye solutions are proposed. The dyes are produced by transformation of 4,4'-biphenylene-bis-(methylenoxy-2-benzaldehydes) or their bisaniles in bipolar aprotic solvents adding strongly basic alkali compounds to the benzofurans and subsequent sulfonation.

  19. Dye laser

    Energy Technology Data Exchange (ETDEWEB)

    Telle, H.; Schieder, R.; Raue, R.; Eckstein, U.

    1980-05-22

    For a laser radiating in the range of wavelengths from 420 to 480 nm dye solutions are proposed. The dyes are produced by transformation of 4,4'-biphenylene-bis-(methylenoxy-2-benzaldehydes) or their bisaniles in bipolar aprotic solvents adding strongly basic alkali compounds to the benzofurans and subsequent sulfonation.

  20. Synthesis and Biological Activities of Schiff Bases of 3-Amino-1H-1,2,4-triazole

    Institute of Scientific and Technical Information of China (English)

    SUN,Xiaohong; LIU,Yuanfa; CHEN,Shuzhe; CHEN,Bang; JIA,Yingqi; ZENG,Zhengfang

    2009-01-01

    Eight Schiff bases of 3-amino-1H-1,2,4-triazole have been synthesized by glacial acetic acid catalyzed conden- sation of 3-amino-1H-1,2,4-triazole with substituted benzaldehyde and structurally confirmed by IR, 1H NMR and elemental analysis. The preliminary bioassay showed that the title compounds exhibited good fungicidal activities.

  1. Installation Restoration Program. Remedial Investigation Report. Volk Field Air National Guard, Camp Douglas, Wisconsin. Volume 2

    Science.gov (United States)

    1993-09-01

    lives of 15 minutes and 0.61 days, respectively). Direct photodegradation and removal by rain may also occur. Phenol is not expected to...acid, benzaldehyde, explosives, dyes , and many other organic compounds. Toluene functions as a solvent in products such as wood furniture cleaners

  2. Synthesis of some novel fluoro isoxazolidine and isoxazoline derivatives using -benzyl fluoro nitrone via cycloaddition reaction in ionic liquid

    Indian Academy of Sciences (India)

    Bhaskar Chakraborty; Govinda Prasad Luitel

    2013-09-01

    1-Butyl-3-methylimidazolium-based ionic liquids are found to accelerate significantly the intermolecular 1,3-dipolar cycloaddition of -benzyl-fluoro nitrone derived in situ from 2,6-difluoro benzaldehyde and -benzylhydroxylamine, with activated alkenes and electron deficient alkynes to afford enhanced rates and improved yields of novel isoxazolidines and isoxazolines.

  3. A New Phenolic Compound I solated from SemenCelo si a cristata L.

    Directory of Open Access Journals (Sweden)

    Qiyan Li

    2017-03-01

    Full Text Available A new phenolic compound, named 3-geranyl-2,5-dihydroxy-benzaldehyde (1, together with seven known chalone derivatives (2–8 has been isolated from the seeds of Celosia cristata L. Their chemical structures have been elucidated by spectroscopic analysis. All these compounds (1–8 were isolated from C. cristata for the first time.

  4. Exploring the Stereochemistry of the Wittig Reaction: The Unexpected Influence of a Nominal Spectator Ion

    Science.gov (United States)

    Hanson, John; Dasher, Bill; Scharrer, Eric; Hoyt, Tim

    2010-01-01

    Students in the second-semester organic chemistry laboratory perform a Wittig reaction between butylidenetriphenylphosphorane (an ylide) and benzaldehyde and determine the relative percentages of the cis and trans isomers of the 1-phenyl-1-pentene product. Because of the highly reactive nature of this unstabilized ylide, students are introduced to…

  5. Synthesis of Arylzinc Thiolates Containing Perfluoroalkyl Chains : Model Catalyst Precursors for the Enantioselective Zinc-Mediated 1,2-Addition of Dialkylzincs to Aldehydes in Fluorous Biphase Systems

    NARCIS (Netherlands)

    Koten, G. van; Kleijn, H.; Rijnberg, E.; Jastrzebski, J.T.B.H.

    1999-01-01

    The synthesis of perfluoroalkyl-functionalized arene trimethylsilyl ethers and their conversion to ethylzinc thiolates is described. These compounds have been successfully applied as catalysts in the enantioselective addition of diethylzinc to benzaldehyde. This is the first example of a two-phase o

  6. Activity and Enantioselectivity of the Hydroxynitrile Lyase MeHNL in Dry Organic Solvents

    NARCIS (Netherlands)

    Hanefeld, U.; Paravidino, M.; Sorgedrager, M.; Orru, R.V.A.

    2010-01-01

    Water concentration affects both the enantioselectivity and activity of enzymes in dry organic media. Its influence has been investigated using the hydrocyanation of benzaldehyde catalyzed by hydroxynitrile lyase cross-linked enzyme aggregate (MeHNL-CLEA) as a model reaction. The enzyme displayed hi

  7. Brown dog tick, Rhipicephalus sanguineus sensu lato, infestation ofsusceptible dog hosts is reduced by slow release of semiochemicalsfrom a less susceptible host

    Science.gov (United States)

    Domestic dog breeds are hosts for the tick Rhipicephalus sanguineus sensu lato, but infestation levels vary among breeds. Beagles are less susceptible to tick infestations than English cocker spaniels due to enhanced production of 2-hexanone and benzaldehyde that act as tick repellents. We report th...

  8. Solvent-Free Synthesis of Chalcones

    Science.gov (United States)

    Palleros, Daniel R.

    2004-01-01

    The synthesis of twenty different chalcones in the absence of solvent is presented. The results indicated that out of the twenty different chalcones investigated seventeen can be obtained in a matter of minutes by mixing the corresponding benzaldehyde and acetophenone in the presence of solid NaOH in a mortar with pestle.

  9. Synthetic Studies of Bioactive Substances of 4-Hydroxybenzalhydantoin Derivatives

    Science.gov (United States)

    Hidayat, IW; Sumiarsa, D.; Permatasari, M.; AKania; Riska; Priani, L.

    2017-02-01

    4-hydroxybenzalhydantoin derivatives were synthesized by the condensation reaction between benzaldehydes 12-13 and substituted hydantoins 14-16 under standard conditions of reflux in glacial acetic acid, in the present of sodium acetate and a little amount of acetic anhydride as a catalyst. All compounds were identified by spectral analysis to give 4-hydroxybenzalhydantoins 17-21.

  10. Synthesis of naphthoxazinone derivatives using silica-bonded -sulfonic acid as catalyst under solvent-free conditions

    Indian Academy of Sciences (India)

    Khodabakhsh Niknam; Parisa Abolpour

    2015-07-01

    Silica-bonded -sulfonic acid is employed as a recyclable catalyst for the synthesis of naphthoxazinone derivatives from the reaction of -naphthol, aromatic aldehydes and urea at 150°C under solvent-free conditions. The heterogeneous catalyst was recycled for five runs after the reaction of -naphthol, benzaldehyde and urea without losing its catalytic activity.

  11. Azeotropic Preparation of a "C"-Phenyl "N"-Aryl Imine: An Introductory Undergraduate Organic Chemistry Laboratory Experiment

    Science.gov (United States)

    Silverberg, Lee J.; Coyle, David J.; Cannon, Kevin C.; Mathers, Robert T.; Richards, Jeffrey A.; Tierney, John

    2016-01-01

    Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with "p"-methoxyaniline in toluene to give 4-methoxy-"N"-(phenylmethylene)benzenamine. Water was removed by azeotropic…

  12. Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage

    DEFF Research Database (Denmark)

    Luu, Thi Xuan Thi; Lam, Trinh To; Le, Thach Ngoc;

    2009-01-01

    oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4 center dot 5H(2)O. The assistance by microwave irradiation results in very short reaction times (eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried...

  13. Federal and State Water Quality Standards/Guidelines for Selected Parameters.

    Science.gov (United States)

    1979-02-01

    Arsenic, total Barium Benzaldehyde Benzanthrone Biochemical Oxygen Demand 1-(2-Butoxyethoxy) ethanol Cadmium Calcium 4 SUBSTANCE LIST FOR SIX STATES... styphnate Magnes i um Mercury Mercury fulminate Mercury, total Methylcyclohexane Methylene chloride Methyl isopropyl ketone 2-Methyl-2-pentanol Nemagon...dye (1-Methylaminoanthraquinone) Silver Sodium Sodium styphnate Strontium nitrate Strontium oxalate Strontium peroxide Sulfate Tetrachlorobenzene

  14. Influence of Ionic Liquids on an Iron(III) Catalyzed Three-Component Coupling/Hydroarylation/Dehydrogenation Tandem Reaction.

    Science.gov (United States)

    Muntzeck, Maren; Wilhelm, René

    2016-06-01

    A three-component oxidative dehydrogenation tandem reaction via the coupling and hydroarylation of benzaldehyde, aniline and phenylacetylene to a quinoline derivate was catalyzed by an iron-containing ionic liquid. The reaction was air mediated and could be performed under neat conditions. The iron(III) of the ionic liquid was the oxidizing species.

  15. Field background odour should be taken into account when formulating a pest attractant based on plant volatiles

    Science.gov (United States)

    Cai, Xiaoming; Bian, Lei; Xu, Xiuxiu; Luo, Zongxiu; Li, Zhaoqun; Chen, Zongmao

    2017-01-01

    Attractants for pest monitoring and controlling can be developed based on plant volatiles. Previously, we showed that tea leafhopper (Empoasca onukii) preferred grapevine, peach plant, and tea plant odours to clean air. In this research, we formulated three blends with similar attractiveness to leafhoppers as peach, grapevine, and tea plant volatiles; these blends were composed of (Z)-3-hexenyl acetate, (E)-ocimene, (E)-4,8-dimethyl-1,3,7-nonatriene, benzaldehyde, and ethyl benzoate. Based on these five compounds, we developed two attractants, formula-P and formula-G. The specific component relative to tea plant volatiles in formula-P was benzaldehyde, and that in formula-G was ethyl benzoate. These two compounds played a role in attracting leafhoppers. In laboratory assays, the two attractants were more attractive than tea plant volatiles to the leafhoppers, and had a similar level of attractiveness. However, the leafhoppers were not attracted to formula-P in the field. A high concentration of benzaldehyde was detected in the background odour of the tea plantations. In laboratory tests, benzaldehyde at the field concentration was attractive to leafhoppers. Our results indicate that the field background odour can interfere with a point-releasing attractant when their components overlap, and that a successful attractant must differ from the field background odour. PMID:28150728

  16. Synthesis of Diphenyl α-(Dipropoxyphosphoramido)alkyl phosphonates

    Institute of Scientific and Technical Information of China (English)

    CUI, Zhan-Wei; ZHANG, Jian-Feng; MIAO, Zhi-Wei; CHEN, Ru-Yu

    2007-01-01

    A convenient method has been developed for the synthesis of diphenyl α-(dipropoxyphosphoramido)alkylphosphonates under mild conditions, namely the reaction of dipropyl phosphoramidate (1) with a para-(un)substituted benzaldehyde or cyclicketone (2) and triphenyl phosphite (3) by a one-pot procedure with the aid of acetyl chloride.

  17. Synthesis of 4-aryl-3,4-dihydrocoumarin derivatives catalyzed by NbCl{sub 5}; Sintese de derivados 4-aril-3,4-di-hidrocuraminicos catalisada por NbCl{sub 5}

    Energy Technology Data Exchange (ETDEWEB)

    Santos, Willian Henrique dos; Siqueira, Mayara de Souza; Silva-Filho, Luiz Carlos da, E-mail: lcsilva@fc.unesp.br [Universidade Estadual Paulista Julio de Mesquita Filho (UNESP), Bauru, SP (Brazil). Faculdade de Ciencias

    2013-11-01

    Multicomponent reactions between phenols, {beta}-diesters and benzaldehydes for the synthesis of 4-aryl-3,4-dihydrocoumarin derivatives were carried out under mild conditions (room temperature) and presented moderate yields (38-88%) and reasonable reaction times (2-4 days), using niobium pentachloride as a catalyst. (author)

  18. Sol-gel process preparation and evaluation of the analytical performances of an hydrazine specific chemical sensor; Preparation par procede sol-gel et evaluation des performances analytiques d`un capteur chimique specifique de l`hydrazine

    Energy Technology Data Exchange (ETDEWEB)

    Gojon, C

    1996-12-01

    The realisation of optical fibers active chemical collector to analyze hydrazine in line, in the spent fuel reprocessing process is the subject of this work. The p.dimethyl-amino-benzaldehyde has been chosen as reagent for its chemical and optical properties. 186 refs.

  19. 2-(4-Diethoxymethylphenyl-6-(4-nitrophenyl-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

    Directory of Open Access Journals (Sweden)

    Hamzeh Kiyani

    2012-09-01

    Full Text Available The photochromic compound was obtained from 4-diethoxymethyl-benzaldehyde and trans-2-benzoyl-3-(4-nitrophenylaziridine via a three component reaction. The structure of this compound was characterized by elemental analysis, 1H-NMR, 13C-NMR and UV-Visible spectral data.

  20. Mechanism and electronic effects in nitrogen ylide-promoted asymmetric aziridination reaction.

    Science.gov (United States)

    Rajeev, Ramanan; Sunoj, Raghavan B

    2011-04-07

    The mechanism and stereoselectivity of the aziridination reaction between guanidinium ylide and a series of para-substituted benzaldehydes have been studied by using density functional theory methods. The mechanistic details and analyses of the key elementary steps involved in (a) the addition of nitrogen ylide to benzaldehydes and (b) subsequent fragmentation of the resulting oxaspirocyclic intermediate are presented. The relative energies of important transition states and intermediates are found to be useful toward rationalizing reported diastereoselective product formation. The relative energies of the key transition states could be rationalized on the basis of the differences in steric, electrostatic, and other stabilizing weak interactions. The deformation analysis of the transition state geometries exhibited good correlation with the predicted activation barriers. The changes in cis/trans diastereoselectivity preferences upon changes in the electron donating/withdrawing abilities of the para substituents on benzaldehyde are identified as arising due to vital differences in the preferred pathways. The large value of reaction constant (ρ > 4.8) estimated from the slope of good linear Hammett plots indicated high sensitivity to the electronic nature of substituents on benzaldehyde. The formation of trans-aziridine in the case of strong electron donating groups and cis-aziridines with weakly electron donating/withdrawing group has been explained by the likely changes in the mechanistic course of the reaction. In general, the predicted trends are found to be in good agreement with the earlier experimental reports.

  1. Environ: E00650 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available ohol [CPD:C00556], Salicylaldehyde [CPD:C06202], Benzaldehyde [CPD:C00261] Cinnamomum cassia [TAX:119260] Sa...me as: D06713 Lauraceae (laurel family) Cinnamomum cassia the dried leaves, twigs, and bark Obtained by stea

  2. CeCl_3·7H_2O as an efficient catalyst for one-pot synthesis of β-amino ketones by three-component Mannich reaction

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    Cerium trichloride heptahydrate(CeCl_3·7H_2O) was found to be an efficient and recyclable catalyst for the three-component direct Mannich reaction of anilines and benzaldehydes with acetophenone.This protocol has advantages of high yield,no environmental pollution,mild condition,and simple work-up procedure.

  3. Synthesis of a novel chemotype via sequential metal-catalyzed cycloisomerizations

    Directory of Open Access Journals (Sweden)

    Bo Leng

    2012-08-01

    Full Text Available Sequential cycloisomerizations of diynyl o-benzaldehyde substrates to access novel polycyclic cyclopropanes are reported. The reaction sequence involves initial Cu(I-mediated cycloisomerization/nucleophilic addition to an isochromene followed by diastereoselective Pt(II-catalyzed enyne cycloisomerization.

  4. Solvent- and Catalyst-Free Direct Aldol Reactions

    Institute of Scientific and Technical Information of China (English)

    王宗令; 张成潘; 张春桃; 肖吉昌

    2011-01-01

    Aldol reaction between simple benzaldehydes and ketones successfully happened in solvent- and catalyst-free condition. The desired products were obtained in moderate yield at suitable temperature. Heat was assumed as the driving force for the reaction. This approach has obvious advantages to fully meet the requirement of the principles of green chemistry.

  5. A Better Sunscreen: Structural Effects on Spectral Properties

    Science.gov (United States)

    Huck, Lawrence A.; Leigh, William J.

    2010-01-01

    A modification of the mixed-aldol synthesis of dibenzylideneacetone, prepared from acetone and benzaldehyde, is described wherein acetone is replaced with a series of cyclic ketones with ring sizes of 5-7 carbons. The structural variations in the resulting conjugated ketones produce regular variations in the UV-vis absorption spectra. The choice…

  6. Deoxygenation of benzoic acid on metal oxides. 2. Formation of byproducts.

    NARCIS (Netherlands)

    Lange, de M.W.; Ommen, van J.G.; Lefferts, L.

    2002-01-01

    Benzene, benzophenone, toluene and benzylalcohol are byproducts in the selective deoxygenation of benzoic acid to benzaldehyde on ZnO and ZrO2. In this paper, the pathways to the byproducts are discussed and a complete overview of the reaction network is presented. Benzene and benzophenone are produ

  7. New Chiral Pyridine Prolinol Derivatives and Preliminary Study on Asymmetric Catalytic Reaction

    Institute of Scientific and Technical Information of China (English)

    Xiao CHEN; Yong Xin ZHANG; Da Ming DU; Wen Ting HUA

    2004-01-01

    Two new chiral pyridine prolinol derivatives have been synthesized from N-alkylation of (S)-α,α-diphenyl-2-pyrrolidinemethanol with 2-bromomethylpyridine and 2, 6-dibromo-methyl-pyridine. The catalytic asymmetric borane reduction of prochiral ketones and the asymmetric addition of diethylzinc to benzaldehyde were investigated.

  8. Inhibition of a Gold-Based Catalyst in Benzyl Alcohol Oxidation: Understanding and Remediation

    NARCIS (Netherlands)

    Skupien, E.; Berger, R.J.; Santos, V.P.; Gascon, J.; Makkee, M.; Kreutzer, M.T.; Kooyman, P.J.; Moulijn, J.A.; Kapteijn, F.

    2014-01-01

    Benzyl alcohol oxidation was carried out in toluene as solvent, in the presence of the potentially inhibiting oxidation products benzaldehyde and benzoic acid. Benzoic acid, or a product of benzoic acid, is identified to be the inhibiting species. The presence of a basic potassium salt (K2CO3 or KF)

  9. SUBCHRONIC SENSITIVITY OF ONE-, FOUR-, AND SEVEN-DAY-OLD FATHEAD MINNOW (PIMEPHALES PROMELAS) LARVAE TO FIVE TOXICANTS

    Science.gov (United States)

    The fathead minnow (pimephales promelas) larval survival and growth test was used to evaluate the relative sensitivity of 1-,4-, and 7-d-old larvae to five contaminants, KC1, NaC1, 1-octanol, carbaryl, and benzaldehyde. The no observable effect concentration (NOEC) for survival o...

  10. Synthesis of pterostilbene by Julie Olefination

    Science.gov (United States)

    A simple, stereoselective route for the synthesis of the biologically active compounds trans-pterostilbene and tetramethoxy stilbene from the readily available starting materials 3,5-dimethoxy benzyl alcohol and 4-hydroxy benzaldehyde was developed using Julia olefination as a key reaction....

  11. Aziridino Alcohols as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Kornø, Hanne Tøfting; Guijarro, David;

    1998-01-01

    addition of diethylzinc to benzaldehyde, with up to 90% stereoselectivity. The absolute configuration of the alcohol product is dependent on the substitution pattern of the aziridine ring, and different transition state models are proposed to explain the observed switch in enantioselectivity. The C-2...

  12. Real World of Industrial Chemistry: Organic Chemicals from Carbon Monoxide.

    Science.gov (United States)

    Kolb, Kenneth E.; Kolb, Doris

    1983-01-01

    Carbon Monoxide obtained from coal may serve as the source for a wide variety of organic compounds. Several of these compounds are discussed, including phosgene, benzaldehyde, methanol, formic acid and its derivatives, oxo aldehydes, acrylic acids, and others. Commercial reactions of carbon monoxide are highlighted in a table. (JN)

  13. Witting Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl Trans-Cinnamate

    Science.gov (United States)

    Speed, Traci J.; Mclntyre, Jean P.; Thamattoor, Dasan M.

    2004-01-01

    An instructive experiment for the synthesis of ethyl trans-cinnamate, a pleasant smelling ester used in perfumery and flavoring by the reaction of benzaldehyde with the stable ylid triphenylphosphorane is described. The synthesis, workup and characterization of trans-cinnamate may be accomplished in a single laboratory session with commonly…

  14. Prunasin hydrolases localization during fruit development in sweet and bitter almonds

    DEFF Research Database (Denmark)

    Sánchez Pérez, Raquel; Belmonte, Fara Sáez; Borch-Jensen, Jonas;

    2012-01-01

    , and benzaldehyde by the action of the β-glucosidase prunasin hydrolase (PH) and mandelonitirile lyase or be glucosylated to form amygdalin. The tissue and cellular localization of PHs was determined during fruit development in two sweet and two bitter almond cultivars using a specific antibody toward PHs. Confocal...

  15. A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds

    Science.gov (United States)

    Rosenberg, Robert E.

    2007-01-01

    The guided-inquiry approach is applied to the reactions of sodium borohydride and phenyl magnesium bromide with benzaldehyde, benzophenone, benzoic anhydride, and ethyl benzoate. Each team of four students receives four unknowns. Students identify the unknowns and their reaction products by using the physical state of the unknown, an…

  16. Trapping noctuid moths with synthetic floral volatile lures

    Science.gov (United States)

    Male and female noctuid moths were collected from plastic bucket traps that were baited with different synthetic floral chemicals and placed in peanut fields. Traps baited with phenylacetaldehyde, benzyl acetate, and a blend of phenylacetaldehyde, benzyl acetate, and benzaldehyde collected more soyb...

  17. Reactive mesogen photoalignment on photopolymerizable composite layer

    Science.gov (United States)

    Mahilny, U. V.; Stankevich, A. I.; Trofimova, A. V.

    2016-08-01

    The volume photoanisotropy (photoinduced birefringence) and surface photoanisotropy (LC photoalignment) of compositions of LC monomer - benzaldehyde polymer upon polarized UV radiation have been revealed and investigated. A high quality of photoalignment is confirmed by an extreme value of birefringence and low imperfection of phase plates fabricated on the basis of LC monomer on composite layer.

  18. Methyl 6-Methyl-1-(4-methylphenyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

    Directory of Open Access Journals (Sweden)

    Haiping Wang

    2012-04-01

    Full Text Available Methyl 6-methyl-1-(4-methylphenyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate has been synthesized via the modified Biginelli reaction from benzaldehyde, p-tolylurea, and methyl acetoacetate, promoted with microwave irradiation and catalyzed by TsOH under solvent-free conditions in high yield.

  19. Probing the Rate-Determining Step of the Claisen-Schmidt Condensation by Competition Reactions

    Science.gov (United States)

    Mak, Kendrew K. W.; Chan, Wing-Fat; Lung, Ka-Ying; Lam, Wai-Yee; Ng, Weng-Cheong; Lee, Siu-Fung

    2007-01-01

    Competition experiments are a useful tool for preliminary study of the linear free energy relationship of organic reactions. This article describes a physical organic experiment for upper-level undergraduates to identify the rate-determining step of the Claisen-Schmidt condensation of benzaldehyde and acetophenone by studying the linear free…

  20. Catalytic Hydrogenation of Organic Compounds without H2 Supply: An Electrochemical System

    Science.gov (United States)

    Navarro, Daniela Maria do Amaral Ferraz; Navarro, Marcelo

    2004-01-01

    An experiment developed for an undergraduate organic chemistry laboratory course that can be used to introduce the catalytic hydrogenation reaction, catalysis electrochemical principles and gas chromatography is presented. The organic compounds hydrogenated by the electrocatalytic hydrogenation (ECH) process were styrene, benzaldehyde and…

  1. Molecular docking study, synthesis and biological evaluation of Schiff bases as Hsp90 inhibitors.

    Science.gov (United States)

    Dutta Gupta, Sayan; Snigdha, D; Mazaira, Gisela I; Galigniana, Mario D; Subrahmanyam, C V S; Gowrishankar, N L; Raghavendra, N M

    2014-04-01

    Heat shock protein 90 (Hsp90) is an emerging attractive target for the discovery of novel cancer therapeutic agents. Docking methods are powerful in silico tools for lead generation and optimization. In our mission to rationally develop novel effective small molecules against Hsp90, we predicted the potency of our designed compounds by Sybyl surflex Geom X docking method. The results of the above studies revealed that Schiff bases derived from 2,4-dihydroxy benzaldehyde/5-chloro-2,4-dihydroxy benzaldehyde demonstrated effective binding with the protein. Subsequently, a few of them were synthesized (1-10) and characterized by IR, (1)HNMR and mass spectral analysis. The synthesized molecules were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The anticancer studies were performed by 3-(4,5-dimethythiazol- 2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay method. The software generated results was in satisfactory agreement with the evaluated biological activity.

  2. 1-Amino-2-hydroxy-4-naphthalenesulfonic acid based Schiff bases or naphtho[1,2-d]oxazoles: selective synthesis and photophysical properties.

    Science.gov (United States)

    Atahan, Alparslan; Durmus, Sefa

    2015-06-05

    A series of Schiff base and naphtho[1,2-d]oxazole derivatives were selectively synthesized via condensation reaction of 1-amino-2-hydroxy-4-naphthalenesulfonic acid and benzaldehyde derivatives at same conditions. The synthesized compounds were then characterized by using (1)HNMR, (13)CNMR, FTIR spectroscopies and elemental analyses. It was seen that the Schiff bases generated in the presence of OH group at ortho position of benzaldehyde derivatives. However, the products were naphtho[1,2-d]oxazoles in other cases. Then, the synthesized compounds were photophysically investigated by UV absorption and fluorescence emission spectroscopies. As a result, these Schiff bases have shown long wavelength absorption (λ(max): 386 nm) and emission (λ(max): 429-437 nm) effect while synthesized naphtho[1,2-d]oxazole derivatives have a set of absorption (λ(max): about 296, 308, 320 nm) and emission maxima (λ(max): 378-395 nm) at lower wavelength.

  3. SYNTHESIS AND BIOLOGICAL SCREENING OF BENZIMIDAZOLE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    Ankur Shukla

    2012-03-01

    Full Text Available The synthesis of benzimidazoles derivative involves subsequent synthesis of 4-(2-chloro-ethoxy-benzaldehyde, 4 methyl benzaldehyde followed by benzimidazoles derivative by reaction between amines derivatives and o-phenylenediamine in dimethyl farmamide (DMF as solvent in the presence of iodine as a catalyst. Iodine is a commercial and environmentally benign catalyst. The yield of all benzimidazole derivatives was found to be in the range of 75 – 94%. The purity of the compounds was ascertained by melting point and TLC. The synthesized compounds were characterized by using IR,1H NMR, and MASS spectral data together with elemental analysis. The synthesized benzimidazole compounds were screened for analgesic and anticonvulsant activity in albino rat (100-200gm by using Writhing test and maximal electroshock (MES. Out of all compound studied only PS-3, PS-4, PS-5 and PS-6 showed significant analgesic activities and response against MES test.

  4. Co-Exposure with Fullerene May Strengthen Health Effects of Organic Industrial Chemicals

    DEFF Research Database (Denmark)

    Lehto, M.; Karilainen, T.; Rog, T.;

    2014-01-01

    In vitro toxicological studies together with atomistic molecular dynamics simulations show that occupational co-exposure with C-60 fullerene may strengthen the health effects of organic industrial chemicals. The chemicals studied are acetophenone, benzaldehyde, benzyl alcohol, m-cresol, and toluene...... which can be used with fullerene as reagents or solvents in industrial processes. Potential co-exposure scenarios include a fullerene dust and organic chemical vapor, or a fullerene solution aerosolized in workplace air. Unfiltered and filtered mixtures of C-60 and organic chemicals represent different...... co-exposure scenarios in in vitro studies where acute cytotoxicity and immunotoxicity of C-60 and organic chemicals are tested together and alone by using human THP-1-derived macrophages. Statistically significant co-effects are observed for an unfiltered mixture of benzaldehyde and C-60 that is more...

  5. Synthesis and E/Z Configuration Determination of Novel Derivatives of 3-Aryl-2-(benzothiazol-2'-ylthio Acrylonitrile, 3-(Benzothiazol-2'-ylthio-4-(furan-2''-yl-3-buten-2-one and 2-(1-(Furan-2''-yl-3'-oxobut-1''-en-2-ylthio-3-phenylquinazolin-4(3H-one

    Directory of Open Access Journals (Sweden)

    Adel Abou El-Khair

    2011-07-01

    Full Text Available Knoevenagel condensation of 2-(benzothiazol-2-ylthio acetonitrile (2 with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a–b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c–e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a with either 1-(benzothiazol-2'-ylthio propan-2-one (5 or 2-(2'-oxo propylthio-3-phenyl-quinazolin-4(3H-one (9 leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, 1H-NMR and 13C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.

  6. Initiation Chemistries in Hydrocarbon (Aut)Oxidation.

    Science.gov (United States)

    Sandhiya, Lakshmanan; Zipse, Hendrik

    2015-09-28

    For the (aut)oxidation of toluene to benzyl hydroperoxide, benzyl alcohol, benzaldehyde, and benzoic acid, the thermochemical profiles for various radical-generating reactions have been compared. A key intermediate in all of these reactions is benzyl hydroperoxide, the heat of formation of which has been estimated by using results from CBS-QB3, G4, and G3B3 calculations. Homolytic O-O bond cleavage in this hydroperoxide is strongly endothermic and thus unlikely to contribute significantly to initiation processes. In terms of reaction enthalpies the most favorable initiation process involves bimolecular reaction of benzyl hydroperoxide to yield hydroxy and benzyloxy radicals along with water and benzaldehyde. The reaction enthalpy and free energy of this process is significantly more favorable than those for the unimolecular dissociation of known radical initiators, such as dibenzoylperoxide or dibenzylhyponitrite.

  7. Antioxidant activities of isolated compounds from stems of Mimosa invisa Mart. ex Colla

    Energy Technology Data Exchange (ETDEWEB)

    Aguiar, Rosane M. [Departamento de Quimica e Exatas, Universidade Estadual do Sudoeste da Bahia, Jequie, BA (Brazil); Alves, Clayton Q.; David, Jorge M.; Rezende, Larissa C. de; Lima, Luciano S., E-mail: jmdavid@ufba.br [Instituto de Quimica, Universidade Federal da Bahia, Salvador, BA (Brazil); David, Juceni P. [Faculdade de Farmacia, Universidade Federal da Bahia, Salvador, BA (Brazil); Queiroz, Luciano P. de [Departamento de Ciencias Biologicas, Universidade Estadual de Feira de Santana, BA (Brazil)

    2012-07-01

    This work describes the phytochemical study of stems of Mimosa invisa (Mimosaceae) and the evaluation of the antioxidant potential of isolated compounds. Chromatographic techniques were employed to isolate salicifoliol, pinoresinol, quercetin, quercetin-3-Orhamnopyranosyl, quercetin-3-O-arabinofuranosyl lupeol, -amyrin, sitosterol, p-hydroxy coumaric acid, 4-hydroxy-3-methoxy benzaldehyde (vanillin), 4-hydroxy-3,5-dimethoxy benzaldehyde, 4-hydroxy-3-methoxy benzoic acid and 4',6,7- trimethoxy flavonol. The latter had been previously described but the spectrometric data shown indicated the structure required review. The antioxidant activity of the compounds was evaluated by the DPPH test and capability of NBT reduction by superoxide radicals. Quercetin glycosides showed lower antioxidant potential than quercetin and, salicifoliol was found to be more active than pinoresinol. (author)

  8. Electrolytic reduction of Nantong coal and model compounds with oxygenic functional groups in an aqueous NaCl solution

    Institute of Scientific and Technical Information of China (English)

    ZHAO Wei; YAO Li-ping; LIN Juan; ZONG Zhi-min

    2008-01-01

    Electrolytic reductions of oxygenic functional groups (OFGs) on coal surface and coal model compounds with OFGs in an aqueous NaCl solution are studied by electrochemical methods combined with GC/MS, GC and FTIR analyses. Different elec-trode reactions, their corresponding potentials and dynamic equations during the processes are investigated. The results show that benzoic acid, benzaldehyde, benzalcohol and hypnone are reduced to benzaldehyde and benzalcohol, methoxybenzene and benzal-cohol, toluene and styrene, respectively, at the cathode. The corresponding electrode potentials and dynamic equations are deter-mined. The electrolytic reduction also leads to an increase in the contents of hydroxyl groups and aliphatic moieties and a corre-sponding decrease in those of carboxyl and carbonyl groups in Nantong coal, a high-sulfur coal, an enhancement in the flotation desulfurization of the coal. ER also reduces organic sulfur and FeS2 in the coal.

  9. OH-radical induced degradation of hydroxybenzoic- and hydroxycinnamic acids and formation of aromatic products-A gamma radiolysis study

    Energy Technology Data Exchange (ETDEWEB)

    Krimmel, Birgit; Swoboda, Friederike [University of Vienna, Department of Nutritional Sciences, Section Radiation Biology (Austria); Solar, Sonja, E-mail: sonja.solar@univie.ac.a [University of Vienna, Department of Nutritional Sciences, Section Radiation Biology (Austria); Reznicek, Gottfried [Department of Pharmacognosy, Althanstrasse 14, A-1090 Vienna (Austria)

    2010-12-15

    The OH-radical induced degradation of hydroxybenzoic acids (HBA), hydroxycinnamic acids (HCiA) and methoxylated derivatives, as well as of chlorogenic acid and rosmarinic acid was studied by gamma radiolysis in aerated aqueous solutions. Primary aromatic products resulting from an OH-radical attachment to the ring (hydroxylation), to the position occupied by the methoxyl group (replacement -OCH{sub 3} by -OH) as well as to the propenoic acid side chain of the cinnamic acids (benzaldehyde formations) were analysed by HPLC-UV and LC-ESI-MS. A comparison of the extent of these processes is given for 3,4-dihydroxybenzoic acid, vanillic acid, isovanillic acid, syringic acid, cinnamic acid, 4-hydroxycinnamic acid, caffeic acid, ferulic acid, isoferulic acid, chlorogenic acid, and rosmarinic acid. For all cinnamic acids and derivatives benzaldehydes were significant oxidation products. With the release of caffeic acid from chlorogenic acid the cleavage of a phenolic glycoside could be demonstrated. Reaction mechanisms are discussed.

  10. OH-radical induced degradation of hydroxybenzoic- and hydroxycinnamic acids and formation of aromatic products—A gamma radiolysis study

    Science.gov (United States)

    Krimmel, Birgit; Swoboda, Friederike; Solar, Sonja; Reznicek, Gottfried

    2010-12-01

    The OH-radical induced degradation of hydroxybenzoic acids (HBA), hydroxycinnamic acids (HCiA) and methoxylated derivatives, as well as of chlorogenic acid and rosmarinic acid was studied by gamma radiolysis in aerated aqueous solutions. Primary aromatic products resulting from an OH-radical attachment to the ring (hydroxylation), to the position occupied by the methoxyl group (replacement -OCH 3 by -OH) as well as to the propenoic acid side chain of the cinnamic acids (benzaldehyde formations) were analysed by HPLC-UV and LC-ESI-MS. A comparison of the extent of these processes is given for 3,4-dihydroxybenzoic acid, vanillic acid, isovanillic acid, syringic acid, cinnamic acid, 4-hydroxycinnamic acid, caffeic acid, ferulic acid, isoferulic acid, chlorogenic acid, and rosmarinic acid. For all cinnamic acids and derivatives benzaldehydes were significant oxidation products. With the release of caffeic acid from chlorogenic acid the cleavage of a phenolic glycoside could be demonstrated. Reaction mechanisms are discussed.

  11. Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage

    Directory of Open Access Journals (Sweden)

    Thi X. Thi Luu

    2009-09-01

    Full Text Available Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step “green” reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4·5H2O. The assistance by microwave irradiation results in very short reaction times (<15 minutes. The green conversion of eugenol (4-allyl-2-methoxyphenol into vanillin (4-hydroxy-3-methoxybenzaldehyde has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde by KF/Al2O3 under solvent-free conditions, respectively.

  12. Fast and green microwave-assisted conversion of essential oil allylbenzenes into the corresponding aldehydes via alkene isomerization and subsequent potassium permanganate promoted oxidative alkene group cleavage.

    Science.gov (United States)

    Luu, Thi X Thi; Lam, Trinh To; Le, Thach Ngoc; Duus, Fritz

    2009-09-03

    Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step "green" reaction pathway based on a solventless alkene group isomerization by KF/Al(2)O(3) to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO(4)/CuSO(4).5H(2)O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al(2)O(3) under solvent-free conditions, respectively.

  13. Condensation reactions of glucose and aromatic ring; Glucose to hokokan tono shukugo hanno

    Energy Technology Data Exchange (ETDEWEB)

    Komano, T.; Mashimo, K.; Wainai, T.; Tanaka, C.; Yoshioka, T. [Nihon University, Tokyo (Japan). College of Science and Technology; Sugimoto, Y.; Miki, Y. [National Institute of Materials and Chemical Research, Tsukuba (Japan)

    1996-10-28

    For artificial coalification, condensation reactions of aromatic ring and activated compounds produced by dehydrating reaction of glucose were studied experimentally. In heat treatment experiment in water, three reaction specimens such as glucose, glucose and phenol, and glucose and benzaldehyde were fed into an autoclave together with distilled water, and subjected to reaction at 180{degree}C under spontaneous pressure for 50 hours. In hydrogenation experiment, the specimens were fed into an autoclave together with tetradecane and sulfurization catalyst, and subjected to reaction at 350{degree}C under initial pressure of 9.8MPa for 2 hours for gas chromatography (GC) analysis of products. As the experimental result, the reaction between glucose and aromatic ring in heat treatment in water occurred between aromatic ring and active fragment with a mean carbon number of 4-5 produced by decomposition of glucose. The reactivity was higher in benzaldehyde addition than phenol addition. 3 refs., 4 figs., 1 tab.

  14. Antioxidant activities of isolated compounds from stems of Mimosa invisa Mart. ex Colla

    Directory of Open Access Journals (Sweden)

    Rosane M. Aguiar

    2012-01-01

    Full Text Available This work describes the phytochemical study of stems of Mimosa invisa (Mimosaceae and the evaluation of the antioxidant potential of isolated compounds. Cromatografic techniques were employed to isolate salicifoliol, pinoresinol, quercetin, quercetin-3-O-rhamnopyranosyl, quercetin-3-O-arabinofuranosyl lupeol, β-amyrin, sitosterol, p-hydroxy coumaric acid, 4-hydroxy-3-methoxy benzaldehyde (vanillin, 4-hydroxy-3,5-dimethoxy benzaldehyde, 4-hydroxy-3-methoxy benzoic acid and 4',6,7- trimethoxy flavonol. The latter had been previously described but the spectrometric data shown indicated the structure required review. The antioxidant activity of the compounds was evaluated by the DPPH test and capability of NBT reduction by superoxide radicals. Quercetin glycosides showed lower antioxidant potential than quercetin and, salicifoliol was found to be more active than pinoresinol.

  15. Total Synthesis of Six 3,4-Unsubstituted Coumarins

    Directory of Open Access Journals (Sweden)

    Wenqing Gao

    2013-12-01

    Full Text Available In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins—7-hydroxy-6,8-dimethoxy-coumarin (isofraxidin, 7-hydroxy-6-methoxycoumarin (scopoletin, 6,7,8-trimethoxy-coumarin, 6,7-dimethoxycoumarin (scoparone, and 7,8-dihydroxycoumarin (daphnetin and one synthetic coumarin, 7-hydroxy-6-ethoxycoumarin. Moreover, five important o-hydroxybenzaldehyde intermediates were also obtained, namely 2,4-dihydroxy-3,5-dimethoxybenzaldehyde, 2,4-dihydroxy-5-methoxybenzaldehyde, 5-ethoxy-2,4-dihydroxy-benzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxy-benzaldehyde. The method developed herein involves just three or four steps and allows for the rapid synthesis of these important molecules in excellent yields. This is the first synthesis of 6,7,8-trimethoxycoumarin and 7-hydroxy-6-ethoxycoumarin.

  16. Analysis and optimization of a synthetic milkweed floral attractant for mosquitoes.

    Science.gov (United States)

    Otienoburu, Philip E; Ebrahimi, Babak; Phelan, P Larry; Foster, Woodbridge A

    2012-07-01

    A pentane extract of flowers of common milkweed, Asclepias syriaca (Asclepiadaceae), elicited significant orientation from both male and female Culex pipiens in a dual-port flight olfactometer. Analysis of the extract by gas chromatography-mass spectrometry revealed six major constituents in order of relative abundance: benzaldehyde, (E)-β-ocimene, phenylacetaldehyde, benzyl alcohol, nonanal, and (E)-2-nonenal. Although not all were collected from the headspace profile of live flowers, a synthetic blend of these six compounds, when presented to mosquitoes in the same levels and proportions that occur in the extract, elicited a response comparable to the extract. Subtractive behavioral bioassays demonstrated that a three-component blend consisting of benzaldehyde, phenylacetaldehyde, and (E)-2-nonenal was as attractive as the full blend. These findings suggest the potential use of synthetic floral-odor blends for monitoring or control of both male and female disease-vectoring mosquitoes.

  17. Catalytic scope of the thiamine-dependent multifunctional enzyme cyclohexane-1,2-dione hydrolase.

    Science.gov (United States)

    Loschonsky, Sabrina; Waltzer, Simon; Fraas, Sonja; Wacker, Tobias; Andrade, Susana L A; Kroneck, Peter M H; Müller, Michael

    2014-02-10

    The thiamine diphosphate (ThDP)-dependent enzyme cyclohexane-1,2-dione hydrolase (CDH) was expressed in Escherichia coli and purified by affinity chromatography (Ni-NTA). Recombinant CDH showed the same C-C bond-cleavage and C-C bond-formation activities as the native enzyme. Furthermore, we have shown that CDH catalyzes the asymmetric cross-benzoin reaction of aromatic aldehydes and (decarboxylated) pyruvate (up to quantitative conversion, 92-99 % ee). CDH accepts also hydroxybenzaldehydes and nitrobenzaldehydes; these previously have not (or only in rare cases) been known as substrates of other ThDP-dependent enzymes. On a semipreparative scale, sterically demanding 4-(tert-butyl)benzaldehyde and 2-naphthaldehyde were transformed into the corresponding 2-hydroxy ketone products in high yields. Additionally, certain benzaldehydes with electron withdrawing substituents were identified as potential inhibitors of the ligase activity of CDH.

  18. Wheat bran valorisation: Towards photocatalytic nanomaterials for benzyl alcohol photo-oxidation.

    Science.gov (United States)

    Ouyang, Weiyi; Reina, Jose M; Kuna, Ewelina; Yepez, Alfonso; Balu, Alina M; Romero, Antonio A; Colmenares, Juan Carlos; Luque, Rafael

    2016-07-13

    In this work, we have successfully synthesized a set of titania photocatalytic nanocomposites by the incorporation of different TiO2 content on wheat bran residues. The obtained catalysts were characterized by different techniques including UV-Vis spectroscopy, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and Transmission Electron Microscopy (TEM) while their photocatalytic activity was investigated in the oxidation of benzyl alcohol under UV light irradiation. Benzaldehyde yields were ca. 20%, with conversion in the systems of ca. 33% of benzyl alcohol by using 10%Ti-Bran catalyst, as compared to 33% yield to the target product (quantitative conversion of benzyl alcohol) using commercial pure TiO2 (P-25). The photocatalytic activity results indicate that designed waste-derived nanomaterials with low TiO2 content can efficiently photocatalyze the conversion of benzyl alcohol with relative high selectivity towards benzaldehyde.

  19. In situ extraction of polar product of whole cell microbial transformation with polyethylene glycol-induced cloud point system.

    Science.gov (United States)

    Wang, Zhilong; Xu, Jian-He; Zhang, Wenzhi; Zhuang, Baohua; Qi, Hanshi

    2008-01-01

    A novel polyethylene glycol-induced cloud point system (PEG-CPS) was developed for in situ extraction of moderate polar product by setting a microbial transformation of benzaldehyde into L-phenylacetylcarbinol (L-PAC) with Saccharomyces cerevisiae (baker's yeast) as a model reaction. The biocompatibility of the microorganism in PEG-CPS was comparatively studied with a series of water-organic solvent two-phase partitioning systems. The tolerance of microorganism to the toxic substrate benzaldehyde was increased and the moderate polar product L-PAC was extracted into the surfactant-rich phase in the PEG-CPS. The novel PEG-CPS fills the gap of in situ extraction of polar product in microbial transformation left by water-organic solvent two-phase partitioning system. At the same time, the application of PEG-CPS in a microbial transformation also avoids expensive solvent when compared with that of aqueous two-phase system or CPS.

  20. Structural variation from heterometallic cluster-based 1D chain to heterometallic tetranuclear cluster: Syntheses, structures and magnetic properties

    Science.gov (United States)

    Zhang, Shu-Hua; Zhao, Ru-Xia; Li, He-Ping; Ge, Cheng-Min; Li, Gui; Huang, Qiu-Ping; Zou, Hua-Hong

    2014-08-01

    Using the solvothermal method, we present the comparative preparation of {[Co3Na(dmaep)3(ehbd)(N3)3]·DMF}n (1) and [Co2Na2(hmbd)4(N3)2(DMF)2] (2), where Hehbd is 3-ethoxy-2-hydroxy-benzaldehyde, Hhmbd is 3-methoxy-2-hydroxy-benzaldehyde, and Hdmaep is 2-dimethylaminomethyl-6-ethoxy-phenol, which was synthesized by an in-situ reaction. Complexes 1 and 2 were characterized by elemental analysis, IR spectroscopy, and X-ray single-crystal diffraction. Complex 1 is a novel heterometallic cluster-based 1-D chain and 2 is a heterometallic tetranuclear cluster. The {Co3IINa} and {Co2IINa2} cores display dominant ferromagnetic interaction from the nature of the binding modes through μ1,1,1-N3- (end-on, EO).

  1. An Efficient One-Pot Multicomponent Synthesis of 4-Aza-Podophyllotoxin Derivatives in Ionic Liquid

    Directory of Open Access Journals (Sweden)

    Hossein Naeimi

    2013-01-01

    Full Text Available A simple, green, and efficient procedure for the synthesis of 4-aza-podophyllotoxin derivatives by using a one-pot three-component reaction of benzaldehydes, 1,3-cyclohexanediones, and anilinolactones in the presence of catalytic amount of alum in 1-butyl-3-methylimidazolium triflate as green media is described. This reaction proceeded under mild conditions with the use of an inexpensive and readily available catalyst, high to excellent yields, and simple workup procedure.

  2. Synthesis of Schiff Bases via Environmentally Benign and Energy-Efficient Greener Methodologies

    Directory of Open Access Journals (Sweden)

    Arshi Naqvi

    2009-01-01

    Full Text Available Non classical methods (water based reaction, microwave and grindstone chemistry were used for the preparation of Schiff bases from 3-chloro-4-fluoro aniline and several benzaldehydes. The key raw materials were allowed to react in water, under microwave irradiation and grindstone. These methodologies constitute an energy-efficient and environmentally benign greener chemistry version of the classical condensation reactions for Schiff bases formation.

  3. Ion mobility spectrometry for detection of skin volatiles

    OpenAIRE

    Ruzsanyi, Veronika; Mochalski, Pawel; Schmid, Alex; Wiesenhofer, Helmut; Klieber, Martin; Hinterhuber, Hartmann; Amann, Anton

    2012-01-01

    Volatile organic compounds (VOCs) released by humans through their skin were investigated in near real time using ion mobility spectrometry after gas chromatographic separation with a short multi-capillary column. VOCs typically found in a small nitrogen flow covering the skin are 3-methyl-2-butenal, 6-methylhept-5-en-2-one, sec-butyl acetate, benzaldehyde, octanal, 2-ethylhexanol, nonanal and decanal at volume fractions in the low part per billion-(ppb) range. The technique presented here ma...

  4. A tribute to Stanislao Cannizzaro, chemical informationist and photochemist.

    Science.gov (United States)

    Roth, Heinz D

    2011-12-01

    Stanislao Cannizzaro is known widely for the Cannizzaro reaction, the "disproportionation" of benzaldehyde upon reaction with alkali, for his approach to teaching chemistry, "Sunto di un corso di filosofia chimica", which he presented at the Karlsruhe Congress of 1860, and for his work on the photochemistry of santonin. In Cannizzaro's laboratory two research associates, Giacomo Ciamician and Paul Silber, and a senior colleague, Emanuele Paternó, became acquainted with the basic methods of sunlight-inducd photochemistry.

  5. 1-[Phenyl(pyridin-2-ylaminomethyl]-2-naphthol

    Directory of Open Access Journals (Sweden)

    Jie Xiao

    2010-11-01

    Full Text Available The title compound, C22H18N2O, was synthesized from naphthalen-2-ol, benzaldehyde and pyridin-2-amine. In the crystal, molecules are linked into centrosymmetric R22(16 dimers by pairs of O—H...N hydrogen bonds. The molecular conformation is stabilized by an N—H...O hydrogen bond. The dihedral angle between the naphthylene ring system and the phenyl ring is 72.86 (12°.

  6. MgO Nanoparticles as a Recyclable Heterogeneous Catalyst for the Synthesis of Polyhydroquinoline Derivatives under Solvent Free Conditions%MgO Nanoparticles as a Recyclable Heterogeneous Catalyst for the Synthesis of Polyhydroquinoline Derivatives under Solvent Free Conditions

    Institute of Scientific and Technical Information of China (English)

    Ranjbar-Karimi, Reza; Hashemi-Uderji, Somayeh; Bazmandegan-Shamili, Alireza

    2011-01-01

    Magnesium oxide nanopartticels in average size between 35--120 nm were prepared by sonochemistry method. Synthesis of polyhydroquinoline derivatives using MgO nanoparticles from the reaction of dimedone, benzaldehyde ethyl acetoacetate and ammonium acetate under solvent-free conditions is reported. Easy handling, reusability, thermal stability and non-toxicity of the catalyst make the present protocol as an eco-friendly and economically acceptable method for synthesis of these heterocycles.

  7. Mesostructured SBA-15-Pr-SO3H: An efficient solid acid catalyst for one-pot and solvent-free synthesis of 3,4-dihydro-2-pyridone derivatives

    Indian Academy of Sciences (India)

    Ghodsi Mohammadi Ziarani; Somayeh Mousavi; Negar Lashgari; Alireza Badiei

    2013-11-01

    3,4-Dihydro-2-pyridone derivatives have been prepared efficiently via a one-pot four-component reaction of benzaldehyde derivatives, Meldrum’s acid, methyl acetoacetate and ammonium acetate in the presence of sulphonic acid-functionalized ordered nanoporous SBA-15 as a nano heterogeneous catalyst under solvent-free conditions. This process is a simple, environmentally friendly, rapid and high yielding reaction.

  8. Effet des extractibles sur la durabilité naturelle du duramen de cyprès

    OpenAIRE

    Mohareb, Ahmed; Sirmah, Peter; Desharnais, Lyne; Dumarçay, Stéphane; Pétrissans,Mathieu; Gérardin, Philippe

    2010-01-01

    International audience; Identification of extractives present in Cupressus lusitanica heartwood has been conducted using GC-MS analyses. The chromatogram of toluene/ethanol extracts indicated the presence of large amounts of benzaldehyde and numerous terpenic compounds such as cedrol, agathadiol, epimanool, bornyl acetate, α-cedrene and β-cedrene.* The effect of these extractives on the natural durability of cypress wood was investigated on heart wood blocks exposed to pure culture of Poria p...

  9. Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

    Directory of Open Access Journals (Sweden)

    Mohammed Salah Ayoup

    2015-12-01

    Full Text Available Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4 are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.

  10. Content of the cyanogenic glucoside amygdalin in almond seeds related to the bitterness genotype

    OpenAIRE

    Arrázola, Guillermo; Sánchez P., Raquel; Dicenta, Federico; Grané, Nuria

    2012-01-01

    Almond kernels can be sweet, slightly bitter or bitter. Bitterness in almond (Prunus dulcis Mill.) and other Prunus species is related to the content of the cyanogenic diglucoside amygdalin. When an almond containing amygdalin is chopped, glucose, benzaldehyde (bitter flavor) and hydrogen cyanide (which is toxic) are released. This two-year-study with 29 different almond cultivars for bitterness was carried out in order to relate the concentration of amygdalin in the kernel with the phenotype...

  11. Crystal-phase control of molybdenum carbide nanobelts for dehydrogenation of benzyl alcohol.

    Science.gov (United States)

    Li, Zhongcheng; Chen, Chunhui; Zhan, Ensheng; Ta, Na; Li, Yong; Shen, Wenjie

    2014-05-04

    Belt-shaped molybdenum carbides in α- and β-phases were synthesized by reducing and carburizing a nano-sized α-MoO3 precursor with hydrocarbon-hydrogen mixtures at appropriate temperatures; the β-Mo2C nanobelts with a higher fraction of coordinatively unsaturated Mo sites were more active than the α-MoC1-x nanobelts in dehydrogenation of benzyl alcohol to benzaldehyde.

  12. Syntheses of 3,4-benzotropolones by ring-closing metatheses.

    Science.gov (United States)

    Arican, Deniz; Brückner, Reinhard

    2013-06-01

    Ortho-lithiated styrenes or ortho-lithiated benzaldehyde dimethyl acetals were added to 2,2-dimethoxypent-4-enals 7. The resulting alcohols were carried on to the aromatic dienones 10. These were ring-closed by olefin metathesis. Hydrolysis of the dimethyl ketal moiety and enolization provided the 3,4-benzotropolones 5. Overall, this access comprises 4-6 steps and totaled a 22-81% yield.

  13. Highly Efficient and Versatile Acetalization of Glycol Catalyzed by Cupric p-Toluenesulfonate

    Institute of Scientific and Technical Information of China (English)

    LIU,Cai-Hua; YU,Xin-Yu; LIANG,Xue-Zheng; WANG,Wen-Juan; YANG,Jian-Guo; HE,Ming-Yuan

    2007-01-01

    Acetalization of glycol with carbonyl compounds was carried out catalyzed by cupric p-toluenesulfonate. These carbonyl compounds included cyclohexanone, propionoaldehyde, n-butyraldehyde, iso-butyraldehyde, n-valeraldehyde, benzaldehyde and butanone. Satisfactory results were obtained: the conversions of these carbonyl compounds were more than 90%, the selectivities were higher than 99.1%, only 0.1% mole ratio of catalyst to substrate and 90 min were sufficient in most cases. The catalyst and products were separated easily by phase separation.

  14. Synthesis of 0,0-diethyl-α-(p-toluenesulphonamido) phosphonates by Mannich-type reaction

    Institute of Scientific and Technical Information of China (English)

    陈茹玉; 戴庆; 张殿坤; 杨秀凤

    1995-01-01

    A series of O,O-diethyl-α-(p-toluenesulphonamido)phosphonates have been synthesized by theMannich-type reaction of p-toluenesulphonamide,substituted benzaldehydes and diethyl phosphite with acetylchloride as the solvent.The mechanism of the reaction is suggested,and the structures of new products areconfirmed by 1H NMR,31p NMR,elemental analysis and X-ray diffraction.The results of preliminarybioassay showed that some of them possess herbicidal activities.

  15. Synthesis of New Bifunctional Bis(oxazolines) and Their Application in the Asymmetric Cyanosilylation of Aromatic Ketones

    Institute of Scientific and Technical Information of China (English)

    LUO,Mei; DU,Da-Ming

    2004-01-01

    @@ Catalytic asymmetric synthesis of tertiary cyanohydrins by the addition of cyanide to a wide range of ketones has important synthetic utility, since the resulting optically active cyanohydrins are important intermediates for the synthesis of a variety of valuable classes of chiral compounds. The application of oxazoline in asymmetric cyanosilylation has seldom reported in comparation with other reactions.[1] Recently, polymer-supported pyridine-bis(oxazoline) ytterbium complex was reported to catalyze cyanosilylation of benzaldehyde.

  16. Solvent‐free synthesis, spectral correlations and antimicrobial activities of some 3,4‐ dimethoxy chalcones

    Directory of Open Access Journals (Sweden)

    V. Mala

    2012-03-01

    Full Text Available Background: The aim of this study was to synthesise some substituted styryl 3,4-dimethoxy phenyl ketones using solvent-free SiO2-H2SO4 catalyzed aldol condensation between 3,4- dimethoxy acetophenone and substituted benzaldehydes under microwave irradiation. Then to characterize them by their analytical, physical and spectroscopic data, and also to study their the spectral correlation and antimicrobial activities.

  17. Microwave-Assisted Synthesis of Some 3,5-Arylated 2-Pyrazolines

    Directory of Open Access Journals (Sweden)

    Hassan Ghasemnejad

    2003-07-01

    Full Text Available Condensation of 2-acetylnaphthalene with benzaldehydes under microwave irradiation affords chalcones which undergo facile and clean cyclizations with hydrazines RNHNH2 (R= H, Ph, Ac to afford 3,5-arylated 2-pyrazolines in quantitative yields, also under microwave irradiation and in the presence of dry AcOH as cyclizing agent. The results obtained indicate that, unlike classical heating, microwave irradiation results in higher yields, shorter reaction times (2-12 min. and cleaner reactions.

  18. Enolboration. 5. An Examination of the Effects of Amine, Solvent, and Other Reaction Parameters on the Stereoselective Enolboration of Ketones with Various Chx sub 2 BX Reagents. An Optimized Procedure to Achieve the Stereoselective Synthesis of E Enol Borinates from Representative Ketones Using Chx sub 2 BC1/Et sub 3 N

    Science.gov (United States)

    1993-10-13

    that the smaller amines, such as pyridine, DABCO, DBU and tetramethylguanidine, complex strongly with R2BOTf reagents and, therefore, are totally ...31 pages) of the benzaldehyde aldol products of the endl borinates representing each study ( totally 38 pages). This material is contained in many...to warm slowly to room temperature overnight unless otherwise stated. dDetermined by IH NMR. eAldolization at 0 OC for 2 h. fEnolization at -78 °C

  19. Exploiting the CNC side chain in heterocyclic rearrangements: synthesis of 4(5)-acylamino-imidazoles.

    Science.gov (United States)

    Piccionello, Antonio Palumbo; Buscemi, Silvestre; Vivona, Nicolò; Pace, Andrea

    2010-08-06

    A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10 catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(alpha-aminobenzyl)-1,2,4-oxadiazole, which was condensed with benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-type rearrangement to afford novel 4(5)-acylaminoimidazoles.

  20. Spectrophotometric Determination of Fenpropathrin in its Formulations and Water Samples

    OpenAIRE

    B. Krishna Priya; Subrahmanyam, P.; Dakshayani, K.; P. Chiranjeevi

    2007-01-01

    Novel spectrophotometric methods were developed for the determination of fenpropathrin in insecticidal formulations and water samples. The methods were based on the hydrolysis of fenpropathrin with ethanolic KOH to form 3-phenoxy benzaldehyde. The resultant aldehyde group was condensed with anthranilic acid in presence of basic medium to form yellowish red color product having λmax of 485 nm or condensed with 2-chloro phenyl hydrazine to form pink color product having λmax of 557 nm. The colo...

  1. Aerobic oxidation of aldehydes under ambient conditions using supported gold nanoparticle catalysts

    DEFF Research Database (Denmark)

    Marsden, Charlotte Clare; Taarning, Esben; Hansen, David

    2008-01-01

    A new, green protocol for producing simple esters by selectively oxidizing an aldehyde dissolved in a primary alcohol has been established, utilising air as the oxidant and supported gold nanoparticles as catalyst. The oxidative esterifications proceed with excellent selectivities at ambient cond...... conditions; the reactions can be performed in an open flask and at room temperature. Benzaldehyde is even oxidised at a reasonable rate below -70 degrees C. Acrolein is oxidised to methyl acrylate in high yield using the same protocol....

  2. Impact du polylactide (PLA) sur la qualité des bioproduits au contact

    OpenAIRE

    Salazar Gonzalez, Romulo Vinicio

    2013-01-01

    Packaging plays a major role in the preservation of food but mass transfer between the packaging material and foodstuff occurs during shelf life leading to the quality deterioration. Polylactide (PLA) is a novel packaging material; therefore its interaction with food was investigated at service conditions. The sorption of ethyl esters, benzaldehyde and 2-nonanone at low concentrations and in mixture and the effects on the thermal properties of PLA were studied. Multiple Headspace Extraction (...

  3. 比色法测定微量尿素最佳条件的探究%Study on the Optimum Condition by Colorimetry

    Institute of Scientific and Technical Information of China (English)

    郎德龙

    2016-01-01

    我国是农业大国,尿素的使用量极大,但是也造成了土壤与水质等方面的污染。溶液中尿素含量在1%以上,用对二甲氨基苯甲醛比色法测定时,能够准确、快捷、操作简便。但当对二甲氨基苯甲醛比色法在测定水中微量尿素时,方法重现性较差。为了有效监控生产和确保回收水质的合格率,以及控制今后的分析数据在误差允许的范围内,将对二甲氨基苯甲醛比色法进行适当改进,可大大提高该方法的灵敏度和准确度。%China is a large agricultural country, a great amount of urea are used, it causes soil and water quality pollutions. When urea content is above 1%, the using of dimethylamino-benzaldehyde method is more accurate, quick, simple operation. dimethylamino-benzaldehyde colorimetry in the determination of trace urea of reproducibility is poor, sample recovery rate is low, not conducive to guide the production process. In order to effectively monitor the production, and ensure the quality of the qualified rate of recovery and control the future of the analysis of the data in the error within the allowable range, dimethyl-amino-benzaldehyde colorimetry was improved properly, it can greatly improve the sensitivity and accuracy. The method of optimal conditions was studied through the different conditions of dimethylamino-benzaldehyde colorimetry.

  4. Chemistry of singlet oxygen. 52. Reaction with trans-stilbene

    Energy Technology Data Exchange (ETDEWEB)

    Kwon, Byoungmog; Foote, C.S.; Khan, S.I. (Univ. of California, Los Angeles (USA))

    1989-07-07

    Substituted trans-stilbenes react with singlet oxygen to give substituted diendoperoxides along with corresponding epoxides, cis-stilbenes, and benzaldehydes. The diendoperoxides rearrange readily to keto compounds on treatment with base. In methyl alcohol, solvent adducts are isolated. Monoendoperoxides are the primary products isolated from the photooxygenation of mono- and dimethoxystilbenes. Structures of several products were confirmed by NMR and X-ray crystallography. The results suggest that endoperoxide formation occurs via a polar intermediate such as a perepoxide or zwitterion.

  5. Synthesis of 14-Fluorophenyl-14H-Dibenzo[a,j]xanthenes and Their Derivatives under Microwave Irradiation and Solvent-free Conditions%Synthesis of 14-Fluorophenyl-14H-Dibenzo[a,j]xanthenes and Their Derivatives under Microwave Irradiation and Solvent-free Conditions

    Institute of Scientific and Technical Information of China (English)

    金见安; 章健民; 商文丽; 朱仕正

    2011-01-01

    A facile and efficient synthesis of 14-fluorophenyl-14H-dibenzo[a,j]xanthenes has been developed by one-pot condensation of fluorinated benzaldehydes with β-naphthol in the presence of p-TSA·H2O under microwave irradiation and solvent-free conditions. These products are conveniently oxidized to 14-fluorophenyl-14-hydroxydibenzo[a,j]xanthenes by PbO2 in acetic acid in good yields.

  6. Synthesis, antimicrobial screening and structure-activity relationship of some novel 2-hydroxy-5-(nitro-substituted phenylazo benzylidine anilines

    Directory of Open Access Journals (Sweden)

    Halve A

    2006-01-01

    Full Text Available The title compounds were synthesized by the condensation of nitro-substituted 2-hydroxy-5- (nitro-substituted phenylazo benzaldehyde (3 with different aromatic amines in presence of ethanol in good yield. The chemical structures were confirmed by IR, 1H NMR and elemental analysis. All the synthesized compounds (4a-j have been evaluated for their in vitro antimicrobial activity against S. aureus , P. aeruginosa , E. coli , A. fumigatus , A. niger and C. neoformans .

  7. Solid-phase microextraction for flavor analysis in Harari Khat (Catha edulis) stimulant

    Institute of Scientific and Technical Information of China (English)

    AL-FLAHI Abdulsalam; ZOU Jian-kai (邹建凯); YIN Xue-feng (殷学锋)

    2004-01-01

    This research examined the typical flavor compounds in the commonest type of Khat called Harari Khat grown in the region of Ethiopia. Twenty-eight compounds, which includes 1,2-Propanedione, 1-Phenyl, Hexanol, Hexanal compounds, Limonene, Benzaldehyde with other flavors, were extracted by polydimethylsiloxane at room temperature for 30 min from Khat samples, and identified by solid-phase microextraction-gas chromatography-mass spectrometry (SPME- GC-MS). This method needs no organic solvents and required minimal sample.

  8. N-Bromosuccinimide Catalyzed One-pot and Rapid Synthesis of Acetamidobenzyl Naphthols under Mild and Solvent-free Conditions

    Institute of Scientific and Technical Information of China (English)

    SHATERIAN Hamid Reza; YARAHMADI Hossein; GHASHANG Majid; SAFARI MEHMANDOSTI Moharram

    2008-01-01

    An efficient,facile and expeditious direct protocol for the preparation of acetamidobenzyl naphthols employing a multi-component and one-pot condensation reaction of 2-naphthoi,benzaldehydes,and acetamide in the presence of N-bromosuccinimide(NBS)under thermal and microwave irradiation conditions has been described.The present protocol with NBS catalyst is convincingly superior to the recently reported catalytic methods.

  9. Preparation and Application of Perchloric Acid Supported on Alumina (Al2O3-HCIO4) to the Synthesis of α-(α-Amidobenzyl)-β-naphthols

    Institute of Scientific and Technical Information of China (English)

    SHATERIAN,Hamid Reza; KHORAMI,Fahimeh; AMIRZADEH,Azita; GHASHANG,Majid

    2009-01-01

    Preparation of perchloric acid supported on alumina and its primary application as a solid supported heterogeneous catalyst to the synthesis of α-(α-amidobenzyl)-β-naphthols by a one-pot,three-component condensation of benzaldehydes,β-naphthol and acetamide or benzamide under thermal solvent-free conditions were described.The present methodology offers several advantages such as simple procedure,shorter reaction time,and excellent yields.

  10. PPA-SiO2 Catalyzed Multi-component Synthesis of N-[α-(β-Hydroxy-α-naphthyl)(benzyl)]O-Alkyl Carbamate Derivatives

    Institute of Scientific and Technical Information of China (English)

    SHATERIAN,Hamid Reza; HOSSEINIAN,Asghar; GHASHANG,Majid

    2009-01-01

    Silica-supported polyphosphoric acid (PPA-SiO2) was found to be an efficient catalyst for the multi-component condensation reaction of benzaldehydes,2-naphthol,and methyl/benzyl carbamate to afford the corresponding N-[α-(β-hydroxy-α-naphthyl)(benzyl)]O-alkyl carbamate derivatives in good to excellent yields.This new approach consistently has the advantage of short reaction time,high conversions,clean reaction profiles,and simple experimental and work-up procedures.

  11. An investigation of the catalytic potential of potassium cyanide and imidazolium salts for ultrasound-assisted synthesis of benzoin derivatives

    OpenAIRE

    Javad Safari; Zohre Zarnegar; Masoume Ahmadi; Susan Seyyedi

    2015-01-01

    A rapid, highly efficient and mild green synthesis of benzoin was performed using substituted benzaldehyde catalyzed by KCN and imidazolium salts in EtOH/H2O under ultrasonic activation. The products were obtained in good yields within short reaction times with N,N′-dialkylimidazolium salts, which were found to be more effective pre-catalysts at room temperature for benzoin condensation in comparison to corresponding cyanide ion in heating method. This simple method affords benzoin derivative...

  12. ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation

    Indian Academy of Sciences (India)

    B Vinay Kumar; Halehatty S Bhojya Naik; D Girija; B Vijaya Kumar

    2011-09-01

    Green chemistry protocols with the reusability of the nano particle as catalyst in the synthesis of coumarins is described. The zinc oxide (ZnO) nanoparticles functions as highly effective catalyst for the reactions of various -hydroxy benzaldehydes with 1,3-dicarbonyl compounds under microwave and thermal conditions to afford the corresponding coumarins in moderate to good yields. The catalyst is inexpensive, stable, can be easily recycled and reused for several cycles with consistent activity.

  13. The pivotal role of chelation as a stereochemical control element in non-Evans anti aldol product formation.

    Science.gov (United States)

    Shinisha, C B; Sunoj, Raghavan B

    2010-06-18

    The origin of stereoselective formation of Evans syn and non-Evans anti aldol products in the reaction between titanium enolate derived from N-succinyloxazolidinone and benzaldehyde is established by using transition-state modeling. The chelated transition-state model is found to hold the key to otherwise less likely non-Evans anti aldol product, whereas the nonchelated model offers a convincing rationalization toward Evans syn aldol product. The computed results are in agreement with the reported experimental observations.

  14. Ab initio and density functional theory evidence on the rate-limiting step in the Morita-Baylis-Hillman reaction.

    Science.gov (United States)

    Roy, Dipankar; Sunoj, Raghavan B

    2007-11-08

    The first ab initio and DFT studies on the mechanism of the MBH reaction show that the rate-limiting step involves an intramolecular proton transfer in the zwitterionic intermediate generated by the addition of enolate to electrophile. The activation barrier for the C-C bond-formation is found to be 20.2 kcal/mol lower than the proton-transfer step for the MBH reaction between methyl vinyl ketone and benzaldehyde catalyzed by DABCO.

  15. New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their O-methyloximes with hydrazine.

    Science.gov (United States)

    Lukin, Kirill; Hsu, Margaret C; Fernando, Dilinie; Leanna, M Robert

    2006-10-13

    The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.

  16. New Conjugated Benzothiazole-N-oxides: Synthesis and Biological Activity

    Directory of Open Access Journals (Sweden)

    Pavlína Foltínová

    2009-12-01

    Full Text Available Eleven new 2-styrylbenzothiazole-N-oxides have been prepared by aldol – type condensation reactions between 2-methylbenzothiazole–N-oxide and para-substituted benzaldehydes. Compounds with cyclic amino substituents showed typical push-pull molecule properties. Four compounds were tested against various bacterial strains as well as the protozoan Euglena gracilis as model microorganisms. Unlike previously prepared analogous benzothiazolium salts, only weak activity was recorded.

  17. Synthesis and insecticidal activities of new pyrethroid acid oxime ester derivatives

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A series of compounds containing oxime-ester linkage in place of the ester linkage in pyrethroid ester are designed and prepared. Bioassay data of insecticidal activities of these compounds on Ostrinia nubilalis (H.) and Culex pipines (L.) are presented. Among them 4-dimethyaminobenzaldehyde oxime ester of 2,2,3,3-tetramethylcyclopropanecarboxylic acid and 4-dimethyamino benzaldehyde oxime ester of cyclopropanecarboxylic acid are found to be potent insecticide against Ostrinia nubilalis (H.). Structure-activity relationship of the compounds is discussed.

  18. Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia.

    Science.gov (United States)

    Yoshioka, Takeo; Inokuchi, Tomohisa; Fujioka, Shozo; Kimura, Yasuo

    2004-01-01

    Five phenolic compounds, 4-hydroxybenzoic acid methyl ester (1), vanillic acid methyl ester (2), 4-hydroxy benzaldehyde (3), 4-hydroxybenzoic acid (4) and ferulic acid (5), and four flavonoids, 5,5'-dihydroxy-4',6,7-trimethoxyflavanone (6), luteolin (7), vitexicarpin (8) and artemetin (9), were isolated from fruits and leaves of Vitex rotundifolia L. The biological activities of these nine compounds have been examined using a bioassay with lettuce seedlings.

  19. Highly Efficient Oxidative Cleavage of Carbon-Carbon Double Bond over meso-Tetraphenyl Cobalt Porphyrin Catalyst in the Presence of Molecular Oxygen

    Institute of Scientific and Technical Information of China (English)

    周贤太; 纪红兵

    2012-01-01

    Highly efficient and selective carbon-carbon double bond aerobic cleavage of olefins catalyzed by metallopor- phyrins was investigated, and carbonyl compounds and epoxide were produced as the main products. CoTPP (co- balt meso-tetraphenyl porphyrin) showed excellent activity for the oxidative cleavage of carbon-carbon double bond by using styrene as model compound, in which the TOF (turnover frequency) and selectivity toward benzaldehyde was obtained with 2×10^4h-1 and 86%,respectively.

  20. Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience

    Science.gov (United States)

    Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr.

    2002-09-01

    A guided inquiry experiment involving the synthesis and characterization of substituted benzalacetophenones (chalcones) is described. The chalcones are produced in the aldol condensation of substituted benzaldehydes with substituted acetophenones. Each student is assigned a different target chalcone and conducts online and printed literature searches on the target. After completing the synthesis and purification of their product, the students compare their data with those found in the literature.

  1. Synthesis, spectral correlation and insect antifeedant activities of some 2-benzimidazole chalcones

    OpenAIRE

    2016-01-01

    Some substituted styryl 2-benzimidazole ketones have been synthesised by fly-ash:H2SO4 catalysed aldol condensation of 2-benzimidazole methyl ketone and various substituted benzaldehydes in microwave oven. The yields of these chalcones are more than 70%. The purities of synthesised benzimidazole chalcones were checked by their physical constants and spectral data earlier published in the literature. The spectral frequencies of these chalcones have been correlated with Hammett substituent cons...

  2. SEPARATION OF PLUTONIUM FROM ELEMENTS HAVING AN ATOMIC NUMBER NOT LESS THAN 92

    Science.gov (United States)

    Fitch, F.T.; Russell, D.S.

    1958-09-16

    other elements having atomic numbers nnt less than 92, It has been proposed in the past to so separate plutonium by solvent extraction iato an organic solvent using triglycoldichlcride as the organic solvent. The improvement lies in the discovery that triglycoldichloride performs far more efflciently as an extractant, wher certain second organie compounds are added to it. Mentioned as satisfactory additive compounds are benzaldehyde, saturated aliphatic aldehydes containtng at least twc carbon atoms, and certain polyhydric phenols.

  3. 1-[Morpholino(phenylmethyl]-2-naphthol

    Directory of Open Access Journals (Sweden)

    Min Min Zhao

    2010-06-01

    Full Text Available There are two independent molecules in the asymmetric unit of the title compound, C21H21NO2, which was synthesized by the one-pot reaction of 2-naphthol, morpholine and benzaldehyde. The dihedral angles between the naphthalene ring systems and the benzene rings are 84.03 (7 and 75.76 (8° in the two molecules and an intramolecular O—H...N hydrogen bond occurs in each independent molecule.

  4. Tracking of the organic species during the synthesis of cobalt-based nanoparticles in non-aqueous solution

    Science.gov (United States)

    Staniuk, M.; Niederberger, M.; Koziej, D.

    2014-08-01

    In this work we investigate the organic products of the synthesis of Co-based nanoparticles in benzyl alcohol. Our GC and in situ IR studies provide the experimental proofs for the formation of benzaldehyde, toluene and isopropanol in the reaction solution. These organic products can be correlated with formation of cobalt-based nanoparticles with oxidation state from 0 to 3+. These results shine the light on the complexity of organic and inorganic reactions in solution during crystallization of nanoparticles.

  5. A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidenecycloalkanones and α,α′-bis-(Substituted-alkylidenecycloalkanones

    Directory of Open Access Journals (Sweden)

    Yurngdong Jahng

    2012-01-01

    Full Text Available Solvent-free Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes (aryl aldehydes using solid NaOH (20 mol% and applying a grinding technique were studied. Quantitative yields (96–98% of α,α-bis-(substituted-benzylidenecycloalkanones were obtained. Aliphatic aldehydes also provided α,α-bis-(substituted-alkylidenecycloalkanones in very good yields with minor amounts of a-(substituted-alkylidenecycloalkanones. The catalytic performance of solid NaOH was examined. The molar ratio of NaOH was optimized. The catalytic effect of solid NaOH was also evaluated by comparing it with KOH, NaOAc, and NH4OAc and it turns out that 20 mol% of solid NaOH was good enough to catalyze the Claisen-Schmidt reactions of cycloalkanones with various substituted benzaldehydes. Additionally, the regioselectivity of the Claisen-Schmidt reaction of acetone with benzaldehyde was examined. Using the same method, we could synthesize the corresponding bis-benzylidene- and mono-benzylideneacetone separately in 98% and 96% yields, respectively.

  6. Peak compression technique in high-performance liquid chromatography

    Institute of Scientific and Technical Information of China (English)

    WEI YuXia; WANG Lin; XlAO ShengYuan; QING Hong; ZHU Yong; HU GaoFei; DENG YuLin

    2009-01-01

    Peak compression technique based on the difference of the solute migration velocity in two different mobile phases was described theoretically and confirmed using benzaldehyde and 4-hydroxyquinoline (4-HQ) as model compounds.After peak compression,the peak compression factors (the ratio of peak width at half-height under non-compression and that under compression condition) of benzaldehyde and 4-HQ were 0.19 and 0.13,respectively.By this application of the peak compression technique to the mixture,both enhanced peak height and good separation were obtained in one run cycle.This peak compression technique was introduced to determine benzaldehyde from semicarbazide-sensitive amine oxidase-catalyzed enzymetic reaction in order to illustrate the applicability of this technique to the real sample.As a result,the peak was compressed effectively,and 4.94-fold,19.3-fold and 5.74-fold enhancement in peak height,plate number and signal to noise ratio were also achieved,respectively.

  7. Baeyer-Villiger oxidation of cyclohexanone to epsilon-caprolactone in airlift sonochemical reactor.

    Science.gov (United States)

    Zhang, Ping; Yang, Mei; Lu, Xiaoping; Han, Pingfang; Wang, Yanru

    2006-12-22

    Baeyer-Villiger oxidation of cyclohexanone to epsilon-caprolactone was studied in a new type reactor--the airlift loop sonochemical reactor. The reactor plays a synergistic effect of sonochemsity and higher oxygen transfer rate. The influences of ultrasound intensity, reaction temperature, the molar ratio of benzaldehyde to cyclohexanone and oxygen gas flow rate on the conversion and selectivity of cyclohexanone were investigated and discussed. Under ultrasound, the amount of benzaldehyde can be reduced from 75% to 67%. Ultrasound not only intensified the rates of reactions but also increased the yield of product. The optimized operation conditions are listed as follows: the reaction temperature is 30 degrees C, the molar ratio of cyclohexanone to benzaldehyde is 1:2, the oxygen gas flow rate is 1.15 cm s(-1), and ultrasonic irradiations 2h at 40 kHz, 2.25 W cm(-2). Under the optimum operation conditions, the average molar yield of epsilon-caprolactone comes up to 87.7%.

  8. Synthesis, characterization and antibacterial studies of ruthenium(III) complexes derived from chitosan schiff base.

    Science.gov (United States)

    Vadivel, T; Dhamodaran, M

    2016-09-01

    Chitosan can be modified chemically by condensation reaction of deacetylated chitosan with aldehyde in homogeneous phase. This condensation is carried by primary amine (NH2) with aldehyde (CHO) to form corresponding schiff base. The chitosan biopolymer schiff base derivatives are synthesized with substituted aldehydes namely 4-hydroxy-3-methoxy benzaldehyde, 2-hydroxy benzaldehyde, and 2-hydroxy-3-methoxy benzaldehyde, becomes a complexing agent or ligand. The Ruthenium(III) complexes were obtained by complexation of Ruthenium with schiff base ligands and this product exhibits as an excellent solubility and more biocompatibility. The novel series of schiff base Ruthenium(III) complexes are characterized by Elemental analysis, FT-IR spectroscopy, and Thermo-gravimetric analysis (TGA). The synthesized complexes have been subjected to antibacterial study. The antibacterial results indicated that the antibacterial activity of the complexes were more effective against Gram positive and Gram negative pathogenic bacteria. These findings are giving suitable support for developing new antibacterial agent and expand our scope for applications.

  9. Fecal volatile components elicit aggregation in the oriental migratory locust, Locusta migratoria manilensis (Orthoptera: Acrididae)

    Institute of Scientific and Technical Information of China (English)

    Wang-Peng Shi; Hong-Li Sun; Nyndat Edward; Yu-Hua Yan

    2011-01-01

    The aggregation components from fecal volatiles of the oriental migratory locust, Locusta migratoria manilensis were identified with gas chromatographic/electroantennographic detector (GC-EAD), GC-MS (mass spectrometry) analyses and behavioral bioassays. Both last instar nymphs and adults of the oriental migratory locust have similar aggregation pheromones in their volatiles. A total of 11 electrophysioiogically active compounds, namely, hexanal, cyclohexanol, heptanal, phenol, 2,5-dimethylpyrazine, benzyl alcohol, benzaldehyde, guaiacol, nonanal, 2,6,6-trimethyl-2-cyclohexene1,4-dione and decyl aldehyde were identified in the fecal volatiles of 2-day-old immature adult male locusts. Only hexanal, nonanal, benzaldehyde, cyclohexanol and 2,5-dimethylpyrazine elicited significant aggregation responses in immature 2-day-old adult males.However, adult males had significantly lower behavioral responses to synthetics of five single compounds than the blend of cyclohexanol, 2,5-dimethyl-pyrazine, benzaldehyde,nonanal, hexanal in ratios of 100 : 100 : 2 : 60 : 30 in the range of 30-60 μg/mL. We propose that it is the blend of these five compounds that plays a key role in eliciting and sustaining aggregation in gregarious oriental migratory locusts. These results also showed that the aggregation pheromones of the oriental migratory locust are significantly different from those found in the desert locust.

  10. Co-exposure with fullerene may strengthen health effects of organic industrial chemicals.

    Directory of Open Access Journals (Sweden)

    Maili Lehto

    Full Text Available In vitro toxicological studies together with atomistic molecular dynamics simulations show that occupational co-exposure with C60 fullerene may strengthen the health effects of organic industrial chemicals. The chemicals studied are acetophenone, benzaldehyde, benzyl alcohol, m-cresol, and toluene which can be used with fullerene as reagents or solvents in industrial processes. Potential co-exposure scenarios include a fullerene dust and organic chemical vapor, or a fullerene solution aerosolized in workplace air. Unfiltered and filtered mixtures of C60 and organic chemicals represent different co-exposure scenarios in in vitro studies where acute cytotoxicity and immunotoxicity of C60 and organic chemicals are tested together and alone by using human THP-1-derived macrophages. Statistically significant co-effects are observed for an unfiltered mixture of benzaldehyde and C60 that is more cytotoxic than benzaldehyde alone, and for a filtered mixture of m-cresol and C60 that is slightly less cytotoxic than m-cresol. Hydrophobicity of chemicals correlates with co-effects when secretion of pro-inflammatory cytokines IL-1β and TNF-α is considered. Complementary atomistic molecular dynamics simulations reveal that C60 co-aggregates with all chemicals in aqueous environment. Stable aggregates have a fullerene-rich core and a chemical-rich surface layer, and while essentially all C60 molecules aggregate together, a portion of organic molecules remains in water.

  11. 羟醛缩合法合成肉桂醛的工艺研究%Research on Synthesis Technology of Cinnamaldehyde by Aldol Reaction

    Institute of Scientific and Technical Information of China (English)

    李海花; 闫顺生

    2012-01-01

    Cinnamaldehyde is synthesized from the reaction of benzaldehyde and acetaldehyde with base as the catalyst. The factors affecting the quality and recovery of cinnamaldehyde, such as the catalyst, the temperature, the molar ration of the benzaldehyde and acetaldehyde are analyzed. The results show that at a temperature of 25 ℃ ,catalyst for sodium hydroxide, benzaldehyde : acetaldehyde = 3 : 1 conditions,the yield of the product can reach 76%.%以苯甲醛、乙醛为原料,在碱性条件下用羟醛缩合法合成产物肉桂醛,并分别考察了催化剂、反应温度、两种原料用量比对产物收率的影响。结果表明:在温度为25℃、催化剂为氢氧化钠、苯甲醛:乙醛=3:1的条件下,产品收率能达到76%。

  12. Study on the Synthesis Process of Dibenzylidene Sorbitol and Derivative

    Institute of Scientific and Technical Information of China (English)

    Li; JiChun

    2001-01-01

    Dibenzylidene Sorbitol (DBS) and Di(P-methylbenzylidene) Sorbitol (P-MeDBS) derivatives, used as crystallinity Polyolefine kind resin transparency nucleating agent, can reduce to a large extent the product's haze, improve its transparency, validly resin's rigidity, heat resistant temperature and modulus of bending. Its good transparency and glossiness are as good as transparent material. It has become polyolefine processing auxiliary that develop most quickly and consume most massively in the world. It is used widely in the processing of transparent plastic package vessel, equipment's parts, file folder and transperene material. The nucleating agent of DBS analog is made from one mole Sorbitol and two mole benzaldehyde dehydration condensation reaction, which associates with by-reaction. Sorbitol containing six hydroxyl group ring condensates with benzaldehyde and yield three acetal compounds-monobenzylidene Sorbitol(hereafier briefly referred to as "MBS”), DBS and Tridibenzylidene Sorbitol(hereafter briefly referred to as "TBS”). MBS and TBS are by-products. The experiment is carried out under the condition of temperature 75'C, reaction time 4 hours and agitation velocity 370 r/min. We conducted intensive research on the effects of Sorbitol/benzaldehyde(S/B) and Sorbitol/P-Me-DBS feeding molar ratios. When B/S is 2, the target product's yield can even be improved to 98.5% and 97.17% respectively, whereas feeding molar ratio are increased or reduced, the product's yield reduces definitely. The reason is that DBS and Derivative are produced by the process that one mole Sorbitol and two mole benzaldehyde condense. Sorbitol can't react validly with the molar ratio being lower than 2 .While B/S is in excess of 2.1, the excess benzaldehyde condenses some yielded DBS and produces TBS. Research data show that feeding molar ratio ought to range from 1.9 to 2.1 in order to acquire high yield and selectivity's target product. The result of synthesizing P-Me-DBS homologue

  13. Study on the Synthesis Process of Dibenzylidene Sorbitol and Derivative

    Institute of Scientific and Technical Information of China (English)

    Li JiChun

    2001-01-01

    @@ Dibenzylidene Sorbitol (DBS) and Di(P-methylbenzylidene) Sorbitol (P-MeDBS) derivatives, used as crystallinity Polyolefine kind resin transparency nucleating agent, can reduce to a large extent the product's haze, improve its transparency, validly resin's rigidity, heat resistant temperature and modulus of bending. Its good transparency and glossiness are as good as transparent material. It has become polyolefine processing auxiliary that develop most quickly and consume most massively in the world. It is used widely in the processing of transparent plastic package vessel, equipment's parts, file folder and transperene material. The nucleating agent of DBS analog is made from one mole Sorbitol and two mole benzaldehyde dehydration condensation reaction, which associates with by-reaction. Sorbitol containing six hydroxyl group ring condensates with benzaldehyde and yield three acetal compounds-monobenzylidene Sorbitol(hereafier briefly referred to as "MBS”), DBS and Tridibenzylidene Sorbitol(hereafter briefly referred to as "TBS”). MBS and TBS are by-products. The experiment is carried out under the condition of temperature 75'C, reaction time 4 hours and agitation velocity 370 r/min. We conducted intensive research on the effects of Sorbitol/benzaldehyde(S/B) and Sorbitol/P-Me-DBS feeding molar ratios. When B/S is 2, the target product's yield can even be improved to 98.5% and 97.17% respectively, whereas feeding molar ratio are increased or reduced, the product's yield reduces definitely. The reason is that DBS and Derivative are produced by the process that one mole Sorbitol and two mole benzaldehyde condense. Sorbitol can't react validly with the molar ratio being lower than 2 .While B/S is in excess of 2.1, the excess benzaldehyde condenses some yielded DBS and produces TBS. Research data show that feeding molar ratio ought to range from 1.9 to 2.1 in order to acquire high yield and selectivity's target product. The result of synthesizing P

  14. Health-Beneficial Phenolic Aldehyde in Antigonon leptopus Tea

    Directory of Open Access Journals (Sweden)

    Vanisree Mulabagal

    2011-01-01

    Full Text Available Tea prepared from the aerial parts of Antigonon leptopus is used as a remedy for cold and pain relief in many countries. In this study, A. leptopus tea, prepared from the dried aerial parts, was evaluated for lipid peroxidation (LPO and cyclooxygenase (COX-1 and COX-2 enzyme inhibitory activities. The tea as a dried extract inhibited LPO, COX-1 and COX-2 enzymes by 78%, 38% and 89%, respectively, at 100 g/mL. Bioassay-guided fractionation of the extract yielded a selective COX-2 enzyme inhibitory phenolic aldehyde, 2,3,4-trihydroxy benzaldehyde. Also, it showed LPO inhibitory activity by 68.3% at 6.25 g/mL. Therefore, we have studied other hydroxy benzaldehydes and their methoxy analogs for LPO, COX-1 and COX-2 enzymes inhibitory activities and found that compound 1 gave the highest COX-2 enzyme inhibitory activity as indicated by a 50% inhibitory concentration (IC50 at 9.7 g/mL. The analogs showed only marginal LPO activity at 6.25 g/mL. The hydroxy analogs 6, 7 and 9 showed 55%, 61% and 43% of COX-2 inhibition at 100 g/mL. However, hydroxy benzaldehydes 3 and 12 showed selective COX-1 inhibition while compounds 4 and 10 gave little or no COX-2 enzyme inhibition at 100 g/mL. At the same concentration, compounds 14, 21 and 22 inhibited COX-1 by 83, 85 and 70%, respectively. Similarly, compounds 18, 19 and 23 inhibited COX-2 by 68%, 72% and 70%, at 100 g/mL. This is the first report on the isolation of compound 1 from A. leptopus tea with selective COX-2 enzyme and LPO inhibitory activities.

  15. Single-site SBA-15 supported zirconium catalysts. Synthesis, characterization and toward cyanosilylation reaction

    Energy Technology Data Exchange (ETDEWEB)

    Xu, Wei; Yu, Bo; Zhang, Ying; Chen, Xi; Zhang, Guofang, E-mail: gfzhang@snnu.edu.cn; Gao, Ziwei, E-mail: zwgao@snnu.edu.cn

    2015-01-15

    Graphical abstract: Ligand-modified signal-site SBA-15 supported zirconium catalysts were synthesized by SOMC method and characterized by a variety of techniques. The zirconium surface complexes show high catalytic efficiency for cyanosilylation of benzaldehyde. - Highlights: • Some Zr active species have been anchored on the surface of SBA-15 by SOMC technique. • The structures of the Zr species have been characterized by a variety of techniques. • The anchored Zr species are single-sited surface complexes. • The Zr surface complexes are catalytic active for cyanosilylation of benzaldehyde. - Abstract: A successive anchoring of Zr(NMe{sub 2}){sub 4}, cyclopentadiene and a O-donor ligand, 1-hydroxyethylbenzene (PEA), 1,1′-bi-2-naphthol (Binol) or 2,3-dihydroxybutanedioic acid diethyl ester (Tartrate), on dehydroxylated SBA-15 pretreated at 500 °C for 16 h (SBA-15{sub -500}) was conducted by SOMC strategy in moderate conditions. The dehydoxylation of SBA-15 was monitored by in situ Fourier transform infrared spectroscopy (in situ FT-IR). The ligand-modified SBA-15{sub -500} supported zirconium complexes were characterized by in situ FT-IR, {sup 13}C CP MAS-NMR, X-ray photoelectron spectroscopy (XPS), inductively coupled plasma mass spectrometry (ICP-MAS) and elemental analysis in detail, verifying that the surface zirconium species are single-sited. The catalytic activity of these complexes was evaluated by cyanosilylation of benzaldehyde. The results showed that the catalytic activity is dependent strongly on the structure of surface species and the configuration of the ligands.

  16. Ovicidal and adulticidal activities of Cinnamomum zeylanicum bark essential oil compounds and related compounds against Pediculus humanus capitis (Anoplura: Pediculicidae).

    Science.gov (United States)

    Yang, Young-Cheol; Lee, Hoi-Seon; Lee, Si Hyeock; Clark, J Marshall; Ahn, Young-Joon

    2005-12-01

    The toxicity of cinnamon, Cinnamomum zeylanicum, bark essential oil compounds against eggs and adult females of human head louse, Pediculus humanus capitis, was examined using direct contact and vapour phase toxicity bioassays and compared with the lethal activity of their related compounds, benzyl alcohol, cinnamic acid, cinnamyl acetate, 4-hydroxybenzaldehyde and salicylaldehyde, as well as two widely used pediculicides, d-phenothrin and pyrethrum. In a filter-paper contact toxicity bioassay with female lice at 0.25 mg/cm(2), benzaldehyde was 29- and 27-fold more toxic than pyrethrum and d-phenothrin, respectively, as judged by median lethal time (LT(50)) values. Salicylaldehyde was nine and eight times more active than pyrethrum and d-phenothrin, respectively. Pediculicidal activity of linalool was comparable with that of d-phenothrin and pyrethrum. Cinnamomum bark essential oil was slightly less effective than either d-phenothrin or pyrethrum. Benzyl alcohol and (E)-cinnamaldehyde exhibited moderate pediculicidal activity. After 24h of exposure, no hatching was observed with 0.063 mg/cm(2) salicylaldehyde, 0.125 mg/cm(2) benzaldehyde, 0.5mg/cm(2)Cinnamomum bark essential oil, 1.0 mg/cm(2) (E)-cinnamaldehyde, and 1.0 mg/cm(2) benzyl cinnamate. Little or no ovicidal activity was observed with d-phenothrin or pyrethrum. In vapour phase toxicity tests with female lice, benzaldehyde and salicylaldehyde were much more effective in closed containers than in open ones, indicating that the mode of delivery of these compounds was largely due to action in the vapour phase. Neither d-phenothrin nor pyrethrum exhibited fumigant toxicity. Cinnamomum bark essential oil and test compounds described merit further study as potential pediculicides or ovicides for the control of P. h. capitis.

  17. Invasive Vespula Wasps Utilize Kairomones to Exploit Honeydew Produced by Sooty Scale Insects, Ultracoelostoma.

    Science.gov (United States)

    Brown, Robert L; El-Sayed, Ashraf M; Unelius, C Rikard; Beggs, Jacqueline R; Suckling, David M

    2015-11-01

    Vespula wasps are widely distributed invasive alien species that are able to reach high population densities in the 1.2 M ha of beech forests (Fuscospora spp.) of New Zealand's South Island. These endemic temperate forests have an abundance of carbohydrate-rich honeydew produced by native scale insects (Ultracoelostoma spp.). A characteristic aroma is associated with the honeydew in beech forests, which we hypothesized is the signal used by wasps to harvest the vast resources previously exploited by birds and other insects. Volatile collections were taken of black beech tree trunks with honeydew and sooty mold present, and analyzed with a gas chromatograph-mass spectrometer. Eleven compounds (benzaldehyde, benzyl alcohol, 2-phenylethyl acetate, 2-phenylethanol, phenylacetaldehyde, methyl 2-phenylacetate, ethyl 2-phenylacetate, methyl salicylate, n-octanol, octan-3-ol, and 1-octen-3-ol) were positively identified from the headspace, and were shown to elicit an electrophysiological response from Vespula vulgaris worker antennae by using electroantennography (EAG). Field trials with delta traps individually baited with these compounds confirmed wasp attraction to 8 of the 11 compounds tested, with 2-phenylethyl acetate, methyl salicylate, and octan-3-ol capturing the same numbers of wasps as the control. In later trials, attraction to a 1:1 blend of benzaldehyde and n-octanol was significantly higher (45%) than to any other treatment. Many of the chemicals identified are known to be associated with fermenting sugars, or with fungal aroma. Benzaldehyde and n-octanol are common compounds produced by many different species in nature. The ability to respond to generic signals emanating from sugar resources is likely to contribute to the success of V. vulgaris as an invasive species.

  18. Odor-baited trap trees: a new approach to monitoring plum curculio (Coleoptera: Curculionidae).

    Science.gov (United States)

    Prokopy, Ronald J; Chandler, Bradley W; Dynok, Sara A; Piñero, Jaime C

    2003-06-01

    We compared a trap approach with a trap-tree approach to determine the need and timing of insecticide applications against overwintered adult plum curculios, Conotrachelus nenuphar (Herbst.), in commercial apple orchards in Massachusetts in 2002. All traps and trap trees were baited with benzaldehyde (attractive fruit odor) plus grandisoic acid (attractive pheromone). Sticky clear Plexiglas panel traps placed at orchard borders, designed to intercept adults immigrating from border areas by flight, captured significantly more adults than similarly placed black pyramid traps, which are designed to capture adults immigrating primarily by crawling, or Circle traps wrapped around trunks of perimeter-row trees, which are designed to intercept adults crawling up tree trunks. None of these trap types, however, exhibited amounts of captures that correlated significantly with either weekly or season-long amounts of fresh ovipositional injury to fruit by adults. Hence, none appears to offer high promise as a tool for effectively monitoring the seasonal course of plum curculio injury to apples in commercial orchards in Massachusetts. In contrast, baiting branches of selected perimeter-row trees with benzaldehyde plus grandisoic acid led to significant aggregation (14-15-fold) of ovipositional injury, markedly facilitating monitoring of the seasonal course of injury to apples. A concurrent experiment revealed that addition of other synthetic fruit odor attractants to apple trees baited with benzaldehyde plus grandisoic acid did not enhance aggregation of ovipositional injury above that of this dual combination. We conclude that monitoring apples on odor-baited trap trees for fresh ovipositional injury could be a useful new approach for determining need and timing of insecticide application against plum curculio in commercial orchards.

  19. Formation of highly oxygenated low-volatility products from cresol oxidation

    Science.gov (United States)

    Schwantes, Rebecca H.; Schilling, Katherine A.; McVay, Renee C.; Lignell, Hanna; Coggon, Matthew M.; Zhang, Xuan; Wennberg, Paul O.; Seinfeld, John H.

    2017-03-01

    Hydroxyl radical (OH) oxidation of toluene produces ring-retaining products: cresol and benzaldehyde, and ring-opening products: bicyclic intermediate compounds and epoxides. Here, first- and later-generation OH oxidation products from cresol and benzaldehyde are identified in laboratory chamber experiments. For benzaldehyde, first-generation ring-retaining products are identified, but later-generation products are not detected. For cresol, low-volatility (saturation mass concentration, C* ˜ 3.5 × 104 - 7.7 × 10-3 µg m-3), first- and later-generation ring-retaining products are identified. Subsequent OH addition to the aromatic ring of o-cresol leads to compounds such as hydroxy, dihydroxy, and trihydroxy methyl benzoquinones and dihydroxy, trihydroxy, tetrahydroxy, and pentahydroxy toluenes. These products are detected in the gas phase by chemical ionization mass spectrometry (CIMS) and in the particle phase using offline direct analysis in real-time mass spectrometry (DART-MS). Our data suggest that the yield of trihydroxy toluene from dihydroxy toluene is substantial. While an exact yield cannot be reported as authentic standards are unavailable, we find that a yield for trihydroxy toluene from dihydroxy toluene of ˜ 0.7 (equal to the reported yield of dihydroxy toluene from o-cresol; Olariu et al., 2002) is consistent with experimental results for o-cresol oxidation under low-NO conditions. These results suggest that even though the cresol pathway accounts for only ˜ 20 % of the oxidation products of toluene, it is the source of a significant fraction (˜ 20-40 %) of toluene secondary organic aerosol (SOA) due to the formation of low-volatility products.

  20. Cells of Candida utilis for in vitro (R)-phenylacetylcarbinol production in an aqueous/octanol two-phase reactor.

    Science.gov (United States)

    Rosche, Bettina; Breuer, Michael; Hauer, Bernhard; Rogers, Peter L

    2005-04-01

    (R)-Phenylacetylcarbinol (PAC), a pharmaceutical precursor, was produced from benzaldehyde and pyruvate by pyruvate decarboxylase (PDC) of Candida utilis in an aqueous/organic two-phase emulsion reactor. When the partially purified enzyme in this previously established in vitro process was replaced with C. utilis cells and the temperature was increased from 4 to 21 degrees C, a screen of several 1-alcohols (C4-C9) confirmed the suitability of 1-octanol as the organic phase. Benzyl alcohol, the major by-product in the commercial in vivo conversion of benzaldehyde and sugar to PAC by Saccharomyces cerevisiae, was not formed. With a phase volume ratio of 1:1 and 5.6 g C. utilis l-1 (PDC activity 2.5 U ml-1), PAC levels of 103 g l-1 in the octanol phase and 12.8 g l-1 in the aqueous phase were produced in 15 h at 21 degrees C. In comparison to our previously published process with partially purified PDC in an aqueous/octanol emulsion at 4 degrees C, PAC was produced at a 4-times increased specific rate (1.54 versus 0.39 mg U-1 h-1) with simplified catalyst production and reduced cooling cost. Compared to traditional in vivo whole cell PAC production, the yield on benzaldehyde was 26% higher, the product concentration increased 3.9-fold (or 6.9-fold based on the organic phase), the productivity improved 3.1-fold (3.9 g l-1 h-1) and the catalyst was 6.9-fold more efficient (PAC/dry cell mass 10.3 g g-1).

  1. Synthesis of Dibenzylidene Sorbitol Series Compound

    Institute of Scientific and Technical Information of China (English)

    FENG Rongxiu; CHEN Ligong; HOU Zhongke; SONG Jian

    2007-01-01

    A series of alditol derivatives were designed and synthesized with relatively high yield. On the basis of reaction between sorbitol and a series of substituted benzaldehyde in the presence of an acid catalyst, a series of acetal derivatives were synthesized through free hydroxyl esterification. D-sorbitol acetal amido derivatives were prepared by reduction of nitryl and acylation of amino. Dsorbitol acetal carboxyl esterification derivatives were prepared through esterification and hydrolysis. By high performance liquid chromatography-mass spectra (HPLC-MS) and H nuclear magneticresonance spectra (1 H-NMR), 36 compounds prepared were identified. Among these derivatives prepared, 26 compounds have not been reported in the previous literatures.

  2. An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound.

    Science.gov (United States)

    Khan, Khalid M; Jamil, Waqas; Ambreen, Nida; Taha, Muhammad; Perveen, Shahnaz; Morales, Guillermo A

    2014-05-01

    Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.

  3. Microwave-Assisted Synthesis of Some Quinoxaline-Incorporated Schiff Bases and Their Biological Evaluation

    Directory of Open Access Journals (Sweden)

    L. Achutha

    2013-01-01

    Full Text Available Quinoxaline-incorporated Schiff bases (4a–j were synthesized by the condensation of 2-[(3-methylquinoxalin-2-yloxy]acetohydrazide (3 with indole-3-carbaldehyde, furfuraldehyde, 5-(4-nitrophenyl-2-furfuraldehyde, and substituted benzaldehydes under conventional and microwave irradiation methods. The microwave method was found to be remarkably successful with higher yields, less reaction time, and environmentally friendly compared to conventional heating method. The chemical structures of the synthesized compounds have been confirmed by analytical and spectral data. All the compounds have been evaluated for antitubercular and anti-inflammatory activities.

  4. Ion mobility spectrometry for detection of skin volatiles.

    Science.gov (United States)

    Ruzsanyi, Veronika; Mochalski, Pawel; Schmid, Alex; Wiesenhofer, Helmut; Klieber, Martin; Hinterhuber, Hartmann; Amann, Anton

    2012-12-12

    Volatile organic compounds (VOCs) released by humans through their skin were investigated in near real time using ion mobility spectrometry after gas chromatographic separation with a short multi-capillary column. VOCs typically found in a small nitrogen flow covering the skin are 3-methyl-2-butenal, 6-methylhept-5-en-2-one, sec-butyl acetate, benzaldehyde, octanal, 2-ethylhexanol, nonanal and decanal at volume fractions in the low part per billion-(ppb) range. The technique presented here may contribute to elucidating some physiological processes occurring in the human skin.

  5. Influência da temperatura de secagem sobre o rendimento e a composição química do óleo essencial de Tanaecium nocturnum (barb. Rodr. bur. & K. Shum The influence of drying temperature on the yield and the chemical composition of the essential oil from Tanaecium nocturnum (Barb. Rodr. Bur. & K. Shum

    Directory of Open Access Journals (Sweden)

    Flávio A. Pimentel

    2008-01-01

    Full Text Available The yields and chemical compositions of the essential oils obtained by steam distillation of the fresh and dried (30 and 40 ºC leaves, stems and roots of Tanaecium nocturnum are reported. The identification and quantification of the volatile constituents were accomplished by GC/MS and GC/FID, respectively. The essential oils obtained from the various parts of the plant were constituted mainly of benzaldehyde. Large losses and variations in the quantities of the components during the drying process were observed. The presence of mandelonitrile in higher concentration in the stem and roots indicates that this species produces cyanogenic glycosides.

  6. One-step synthesis of xanthones catalyzed by a highly efficient copper-based magnetically recoverable nanocatalyst.

    Science.gov (United States)

    Menéndez, Cintia A; Nador, Fabiana; Radivoy, Gabriel; Gerbino, Darío C

    2014-06-06

    A versatile and highly efficient strategy to construct a xanthone skeleton via a ligand-free intermolecular catalytic coupling of 2-substituted benzaldehydes and a wide range of phenols has been developed. For this purpose, a novel and magnetically recoverable catalyst consisting of copper nanoparticles on nanosized silica coated maghemite is presented. The reaction proceeds smoothly with easy recovery and reuse of the catalyst. The methodology is compatible with various functional groups and provides an attractive protocol for the generation of a small library of xanthones in very good yield.

  7. Synthesis and Antibacterial Activities of 4-Amino-3-( 1-aryl-5-methyl-1,2,3-triazol-4-yl)-5-mercapto-1,2,4- triazoles/2-Amino-5- ( 1- aryl-5- methyl- 1,2,3- triazol-4- yl )- 1,3,4- thiadiazoles and Their Derivatives

    Institute of Scientific and Technical Information of China (English)

    ZHANG,Yan(张艳); SUN,Xiao-Wen(孙小文); HUI,Xin-Ping(惠新平); ZHANG,Zi-Yi(张自义); WANG,Qin(王勤); ZHANG,Qi(张琪)

    2002-01-01

    Treatment of 4-amino-3- (1-aryl-5-methyl-1,2, 3-triazol-4-yl)-5-mercapto-1, 2, 4-triazoles/2-amino-5-( 1-aryi-5-methyl-1, 2,3-triazol-4-yl)-1, 3,4-thiadiazoles with benzaldehyde, acetone and ω-bromoacetophenone was tested and compared. The title compounds Schiff bases, amides, imidazolo[2,1-b]-1,3,4-thiadiazoles and 7H-s-triazolo [3, 4-b ]-1, 3, 4-thiadiazines have been confirmed by elemental analyses, 1H NMR, IR and MS spectra. All the compounds have also been screened for their antibacterial activities against B. subtilis, S. aureus and E. coli.

  8. Synthesis and Some Reactions of 1-aryl-4-acetyl-5-methyl-1,2,3-triazole Derivatives with Anticonvulsant Activity.

    Science.gov (United States)

    Nassar, Ekhlass M; Abdelrazek, Fathy M; Ayyad, Rezk R; El-Farargy, Ahmed F

    2016-01-01

    The triazoles 3a-d underwent condensation reactions with 4-(piperidin-1-yl)-benzaldehyde to afford the chalcones 5a-d. Chalcone derivatives 5a-d were reacted with 2,3-diaminomaleonitrile, thiourea and hydrazine hydrate to afford the novel diazepine-dicarbonitrile derivatives 7a-d, the pyrimidine-2-thiol derivatives 9a-d and hydrazino-pyrimidines 10a-d respectively. Structures of the prepared compounds were elucidated by physical and spectral data like FT-IR, (1)H NMR, (13)C NMR, and mass spectroscopy. Some of the synthesized compounds were screened for their anticonvulsant activity and SAR.

  9. Metastable Packaging For Transient Electronics

    Science.gov (United States)

    2014-09-01

    Degradation of Resistors The  blue  curve represents a film containing MBTT while the green curve represents a film containing  TPST. Films are similar...at 25 °C after 38 h.  Degradation experiments were performed with free-standing PPA and poly(o-(α- methyl )benzaldehyde (PMBA) films embedded with...preparation and fabrication of transient electronics on robust PPA and POS films were optimized. Three degradation triggers -- direct activation by

  10. Synthesis and characterization of novel substituted N-benzothiazole-2-yl-acetamides

    Directory of Open Access Journals (Sweden)

    H.C. Sakarya

    2016-11-01

    Full Text Available Schiff base derivatives of benzothiazole 2a–e have been synthesized by reacting with substituted 2-aminobenzothiazole 1a–e and different substituted benzaldehydes 5a–e. The obtained Schiff bases reaction with NaBH4 has afforded the corresponding some novel amines 3a–e. The condensation of amines with chloroacetylchloride leads to novel amide derivatives 4a–e. The structures of the synthesized compounds are characterized by elemental analysis, IR, MS, 1H NMR and 13C NMR.

  11. FeF(3) catalyzed cascade C-C and C-N bond formation: synthesis of differentially substituted triheterocyclic benzothiazole functionalities under solvent-free condition.

    Science.gov (United States)

    Atar, Amol B; Jeong, Yeon Tae

    2014-05-01

    A series of diverse polyfunctionalized triheterocyclic benzothiazoles were easily prepared in excellent yields via the Biginelli reaction of 2-aminobenzothiazole with substituted benzaldehydes and α-methylene ketones using FeF(3) as an expeditious catalyst under solvent-free conditions. The protocol provides a practical and straightforward approach toward highly functionalized triheterocyclic benzothiazole derivatives in excellent yields. The reaction was conveniently promoted by FeF(3) and the catalyst could be recovered easily after the reaction and reused without any loss of its catalytic activity. The advantageous features of this methodology are high atom economy, operational simplicity, shorter reaction time, convergence, and facile automation.

  12. Cobalt (II, nickel (II, copper (II and zinc (II complexes of 1-(phenyl(phenylamino methylpyrrolidine-2,5-dione and 2-((phenylaminomethyl isoindoline-1,3-dione and their biological activity

    Directory of Open Access Journals (Sweden)

    D. Tamil Vendan

    2010-12-01

    Full Text Available The new Mannich bases 1-(phenyl(phenylaminomethylpyrrolidine-2,5-dione (SBA was synthesized from the condensation of succinimide, benzaldehyde and aniline. 2-((phenylaminomethylisoindoline-1,3-dione (PFA was derived from pthalimide, formaldehyde and aniline. The general formula of the Co (II, Ni (II, Cu (II and Zn (II chloro complexes, ML2X2 are reported. The ligands and the complexes have been characterized by various physical-chemical techniques such as elemental analysis, molar conductance, magnetic susceptibility measurements, infrared and electronic spectra. The spectral analysis to ascertain mode of bonding and overall geometry of the complexes revealed octahedral geometries.

  13. Cinnamoylacetanilides and Their Metal Chelates

    Institute of Scientific and Technical Information of China (English)

    UMMATHUR Muhammed Basheer; KRISHNANKUTTY Krishnannair

    2008-01-01

    A new series of β-ketoanilides, in which the keto group attached to an olefinic linkage, have been synthesized by the reaction of acetoacetanilide with p-substituted benzaldehydes (4-methoxybenzaldehyde, 4-ethoxybenzaldehyde, 4-dimethylaminobenzaldehyde and 4-nitrobenzaldehyde) under specified conditions. The existence of these β-ketoanilides predominantly in the intramolecularly hydrogen bonded enol forms has been well demonstrated from their IR, 1H NMR and mass spectral data. Details on the formation of [ML2] complexes of these compounds with Ni(Ⅱ), Cu(Ⅱ) and Zn(Ⅱ) and their nature of bonding were discussed on the basis of analytical, IR, 1H NMR and mass spectral data.

  14. Preparation and Analytical Properties of 4-Hydroxybenzaldehyde, Biuret and Formaldehyde Terpolymer Resin

    Directory of Open Access Journals (Sweden)

    Bunian A. Shareef

    2014-01-01

    Full Text Available The chelating resin was synthesized by polycondensation reaction of 4-hydroxy benzaldehyde, formaldehyde and biuret under alkaline condition. The prepared resin was characterized by IR spectroscopy and 1HNMR spectroscopy. The resin sample was cured isothermally at 1200C.The DSC scans was measured for the prepared resin. The analytical evaluation of the prepared resin toward the studied ions (Hg2+, Ni2+ and Pb2+ using the batch method. It was employed to study selectivity of metal ion uptake in a different pH and different treatment time.

  15. Synthesis of New Azo Dyes and Copper(II) Complexes Derived from Barbituric Acid and 4-Aminobenzoylhydrazone

    OpenAIRE

    GUP, Bülent KIRKAN and Ramazan

    2008-01-01

    Four new azo dyes, L1, L2, L3, and L4, were prepared by linking benzaldehyde p-aminobenzoylhydrazone (3) and p-hydroxybenzaldehyede p--aminobenzoylhydrazone (4) to barbituric acid and 1,3-dimethylbarbituric acid through diazo-coupling reactions. Reactions of the azo-dyes with copper chloride and bidentate ligand, 1,10-phenanthroline, produced mixed-ligand dinuclear complexes with general stoichiometry [Cu2L(phen)2]Cl2 (7, 8, 9, and 10). The structures of both azo dyes and their compl...

  16. Designing, synthesis and spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies

    OpenAIRE

    N. RAMAN; S. SYED ALI FATHIMA; DHAVEETHU RAJA

    2008-01-01

    A new series of transition metal complexes of Cu(II), Ni(II), Co(II) and Zn(II) have been designed and synthesized using a Schiff base (L) derived from 4-aminoantipyrine, benzaldehyde and o-phenylenediamine. The structural features were derived from their elemental analyses, magnetic susceptibility and molar conductivity, as well as from mass, IR, UV–Vis, 1H-NMR and ESR spectral studies. The FAB mass spectral data and elemental analyses showed that the complexes had a composition of the ML ty...

  17. Anchoring Tri(8-QuinolinolatoIron Onto Sba-15 for Partial Oxidation of Benzyl Alcohol Using Water as the Solvent

    Directory of Open Access Journals (Sweden)

    Yang Xiaoyuan

    2014-09-01

    Full Text Available Tri(8-quinolinolatoiron complex immobilized onto SBA-15 catalyst has been synthesized through a stepwise procedure. The characterization results indicated that the BET surface area, total pore volume and average pore width decrease after stepwise modification of SBA-15, while the structure keeps intact. Catalytic tests showed that FeQ3-SBA-15 catalyzes the oxidation reaction well with 34.8% conversion of benzyl alcohol and 74.7% selectivity to benzaldehyde when water is used as the solvent after 1 h reaction. In addition, homogeneous catalyst tri(8-quinolinolatoiron exhibits very bad catalytic behavior using water as the solvent.

  18. Stereoselective Synthesis of a New cis Monocyclic β-lactam Bearing a Sugar Moiety at Its N1 Position and Its Physical Characterization

    Directory of Open Access Journals (Sweden)

    Parvaneh Alvand

    2007-05-01

    Full Text Available Synthesis of a new monocyclic β-lactam containing a sugar moiety at its N1 position via [2+2] cycloaddition reaction of ketene and imine is described. Reaction of achiral phenoxy ketene with chiral aldimine derived from chiral 2, 3, 4, 6-tetra-O-acetyl-β-D-galactopyranosylamine and 2-hydroxy-3-methoxy benzaldehyde resulted in the formation of 2 as a single diastereomer. Then its physical characterization has been determined at the AM1 level of theory.

  19. Synthesis of novel pyrazolylquinoxalines

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Ho Sik [Catholoic University of Taegu-Hyosung, Gyongsan (Korea, Republic of); Kwag, Sam Tag [Pukyong National Univ., Pusan (Korea, Republic of)

    2000-06-01

    The reaction of 6-chloro-2-hydrazinoquinoxaline 4-oxide (10) with acetylacetone or dibenzoylmethane gave 6-chloro-2-(3,5-disubstituted pyrazol-1-yl)quinoxaline 4-oxide (11) through the intramolecular cyclization. The chlorination of compound 11 with phosphoryl chloride afforded 3,6-dichloro-2-(3,5-disubstituted pyrazol-l-yl)quinoxalines (12), whose reaction with hydrazine hydrate provided 6-chloro-3-hydrazino-2-(3,4-disubstituted pyrazol-l-yl)quinoxalines (13). The reaction of compound 13 with substituted benzaldehydes, benzenesulfonyl chloride, substituted benzoyl chlorides or acyl chlorides gave novel pyrazolylquinoxalines.

  20. Double Intramolecular Transacetalization of Polyhydroxy Acetals: Synthesis of Conformationally-Restricted 1,3-Dioxanes with Axially-Oriented Phenyl Moiety

    OpenAIRE

    Samuel Asare-Nkansah; Bernhard Wünsch

    2016-01-01

    The synthesis of conformationally-restricted 1,3-dioxanes with a phenyl moiety fixed in an axial orientation at the acetalic center is described. Starting with diethyl 3-hydroxyglutarate (15), benzaldehyde acetal 12a and acetophenone ketal 12b bearing a protected 1,3,5-trihydroxypentyl side chain in the o-position were prepared. The first acid-catalyzed intramolecular transacetalization gave a mixture of diastereomeric 2-benzofurans 18 (ratio of diastereomers 2:2:1:1). After OH group deprotec...

  1. Atualizando a química orgânica experimental da licenciatura

    Directory of Open Access Journals (Sweden)

    Navarro Marcelo

    2005-01-01

    Full Text Available The present contribution describes three different modern experiments for possible adoption in undergraduate organic chemistry laboratories. These are: 1. electrocatalytic hydrogenation of benzaldehyde to benzyl alcohol; 2. identification of three volatile components, obtained from pineapple fruit, by mass spectrometry and 3. microwave mediated fast synthesis of N-(p-chlorophenylphthalamic acid from phthalic anhydride and p-chloroaniline under solvent-free conditions. The experiments can be executed in a short period of time, putting the undergraduate student in contact with a variety of topics in organic chemistry and several techniques of analysis, showing multidisciplinarity in organic chemistry.

  2. rac-2-{[1-(1-Adamant-yl)eth-yl]imino-meth-yl}-5-meth-oxy-phenol.

    Science.gov (United States)

    Jin, Xu-Dong; Wang, Hai-Bo; Jin, Yue-Hong

    2011-09-01

    A novel Schiff base compound, C(20)H(27)NO(2), was obtained by a condensation of rimantadine and 2-hy-droxy-4-meth-oxy-benzaldehyde. An intra-molecular O-H⋯N hydrogen bond supports the phenol-imine tautomeric form. The adamantane and imino-methyl-4-meth-oxy-phenol units are arranged in a folded conformation [C-N-C-C torsion angle = 110.9 (3)°]. In the crystal, highly hydro-phobic adamantane moieties are inserted between the imino-methyl-4-meth-oxy-phenol units in a sandwich-like arrangement along the c axis.

  3. Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Step.

    Science.gov (United States)

    Jayakumar, Jayachandran; Cheng, Chien-Hong

    2016-01-26

    A one-pot reaction of substituted benzaldehydes with alkyne-amines by a Rh-catalyzed C-H activation and annulation to afford various natural and unnatural protoberberine alkaloids is reported. This reaction provides a convenient route for the generation of a compound library of protoberberine salts, which recently have attracted great attention because of their diverse biological activities. In addition, pyridinium salt derivatives can also be formed in good yields from α,β-unsaturated aldehydes and amino-alkynes. This reaction proceeds with excellent regioselectivity and good functional group compatibility under mild reaction conditions by using O2 as the oxidant.

  4. New synthetic way to prepare 2-aryl-8-(piperidin-4-yl)-5, 7-dimethoxy-4H-chromen-4-one as key intermediate for CDK inhibitor

    Institute of Scientific and Technical Information of China (English)

    Yan Ling Li; Hao Fang; Wen Fang Xu; Bing He Wang

    2008-01-01

    As an important intermediate to study cyclin-dependent kinase (CDK) inhibitors, 2-aryl-8-(piperidin-4-yl)-5,7-dimethoxy-4H-chromen-4-one derivatives were prepared using β-diketone route with low yield. In our study, chalcone route has been investigatedand the result suggested that the benzaldehydes substituted with electron-donating group give much better yield than β-diketoneroute. This new method will be an efficient way to start further research on new anticancer flavonoids.2008 Hao Fang. PuNished by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  5. Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl E 2-propen-1-ones.

    Science.gov (United States)

    Sathiyamoorthi, K; Mala, V; Sakthinathan, S P; Kamalakkannan, D; Suresh, R; Vanangamudi, G; Thirunarayanan, G

    2013-08-01

    Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic data. The spectral frequencies of synthesised substituted styryl 4-iodophenyl ketones have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of 4-iodophenyl chalcones have been studied using Bauer-Kirby method.

  6. Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety.

    Science.gov (United States)

    Tomar, V; Bhattacharjee, G; Kamaluddin; Kumar, Ashok

    2007-10-01

    Two new series of chalcones have been synthesized by reacting 1-(4-piperazin-1-yl-phenyl)ethanone and 1-(2,5-dichloro-3-thienyl)-1-ethanone with different substituted benzaldehydes in turn by Claisen-Schmidt condensation. The compounds have been characterized by IR, (1)H NMR spectral and microanalysis data. All the synthesized compounds have been evaluated for antimicrobial activity. Some of these derivatives are potentially active against Gram-positive bacteria, Staphylococcus aureus and Escherichia coli while the most potent compound (1) in this study showed MIC(50) value of 2.22 microg/mL against Candida albicans.

  7. Pygidial gland chemistry and potential alarm-recruitment function in column foraging, but not solitary, Nearctic Messor harvesting ants (Hymenoptera: Formicidae: Myrmicinae).

    Science.gov (United States)

    Hölldobler, Bert; Plowes, Nicola J R; Johnson, Robert A; Nishshanka, Upul; Liu, Chongming; Attygalle, Athula B

    2013-09-01

    We investigated the role of the pygidial gland on foraging behavior in two ecologically dominant column foraging Nearctic harvesting ants (Messor pergandei and Messor andrei). Using chemical analyses and behavioral tests, we show that n-tridecane is the major biologically active compound of pygidial gland secretions in both species, and that this chemical functions as a powerful alarm-recruitment pheromone. Another major compound of pygidial gland contents is benzaldehyde; this substance does not release behavioral reactions in M. pergandei workers but might function as a defensive secretion. Six solitary foraging Nearctic Messor and two column foraging Palearctic Messor species, did not have large pygidial gland reservoirs.

  8. Electrooxidation of carbo/thiocarbohydrazide and their hydrazone derivatives at a glassy carbon electrode

    Indian Academy of Sciences (India)

    G P Mamatha; B S Sherigara; K M Mahadevan

    2007-05-01

    Electrochemical oxidation of thio/carbohydrazide and their hydrazone derivatives Benzaldehyde thiocarbohydrazone [BTCH] diacetylene thiocarbohydrazone [DATCH] have been studied in Britton Robinson buffer in aqueous and nonaqueous media at a glassy carbon electrode. The effects of pH, sweep rate, concentration, temperature and surfactants have been studied. The complex bis (carbo/thiocabohydrazide) Zn(II) chloride was also subjected to voltammetric analysis in order to understand the reactivity both in free and metal bound states. The reaction conditions were optimized for the determination of above compounds in micrograms quantities by differential pulse voltammetry, analytical utility of this investigation is also highlighted.

  9. Mechanism of Prototropy. III. Kinetics of the Tautomerization of Benzylidene-Benzylamine. comparison of the influence of hydrogen and alkyl groups on the S{sub E}2' reaction rate; mecanismo de la Prototropia. III. Cinetica de la tautomerizacion de la benciliden-bencilamina. Comparacion de la influencia del hidrogeno y grupos alcohilos sobre la velocidad de la reaccion S{sub E}2'

    Energy Technology Data Exchange (ETDEWEB)

    Perez Ossorio, R.; Gamboa, J. M.; Martinez Utrilla, R.

    1961-07-01

    The rate of the proto tropic change of benzylidene-benzylamine has been determined by using azomethine {sup 1}4C-labelled in the methylenic group and measuring the distribution of activity between benzaldehyde and benzylamine obtained by hydrolysis at different reaction times. this rate has been compared with those of tautomerization of benzylidene-{alpha}-alkyl benzylamine and {alpha}-alkyl benzylidene-benzyl amines in the same experimental conditions in order to establish ethe influence of alkyl group on this reaction. (Author) 14 refs.

  10. DFT study on mechanism of the classical Biginelli reaction

    Institute of Scientific and Technical Information of China (English)

    Jin Guang Ma; Ji Ming Zhang; Hai Hui Jiang; Wan Yong Ma; Jian Hua Zhou

    2008-01-01

    The condensation of benzaldehyde, urea, and ethyl acetoacetate according to the procedure described by Biginelli was investigated at the B3LYP/6-31G(d), B3LYP/6-31+G(d,p), and B3LYP/6-311+G(3df,2p)//B3LYP/6-31+G(d,p) levels to explore the reaction mechanism. According to the mechanism proposed by Kappe, structures of five intermediates were optimized and four transition states were found. The calculation results proved that the mechanism proposed by Kappe is right.

  11. A new pyrroloquinazoline alkaloid from Linaria vulgaris.

    Science.gov (United States)

    Hua, Huiming; Cheng, Maosheng; Li, Xian; Pei, Yuehu

    2002-10-01

    A new alkaloid, 1,2,3,9-tetrahydropyrrolo(2,1-b)quinazolin-1-carboxylic acid (1), together with eight known compounds, 7-hydroxy vasicine (2), benzyl alcohol beta-D-(2'-O-beta-xylopyranosyl)glucopyranoside (3), benzyl alcohol O-beta-D-glucopyranoside (4), benzyl alcohol O-beta-D-primveroside (5), 3,5-dimethyl-4-hydroxy benzaldehyde (6), gluco-syringic acid (7), syringin (8), and liriodendrin (9), were isolated from the plants of Linaria vulgaris. Their structures were established by spectroscopic methods.

  12. Synthesis of New dihydropyrimidinones catalysed by dicationic ionic liquid

    Indian Academy of Sciences (India)

    Dhanaji V Jawale; Umesh R Pratap; Aparna A Mulay; Jyotirling R Mali; Ramrao A Mane

    2011-09-01

    A convenient multi step synthetic protocol for new dihydropyrimidinones bearing quinolynyl methoxy phenyl moiety has been developed from 2-chloro-3-formyl quinolines. The last step is one-pot Biginelli reaction of multicomponents, 4-((2-chloroquinolin-3-yl) methoxy) benzaldehydes, ethyl acetoacetate and urea mediated and catalysed by dicationic ionic liquid (3-methyl-1-[3-(methyl-1H-imidazolium-1-yl) propyl]-1H-imidazolium dibromide (C3 [min]2 2 [Br−] )). Simple work-up procedures and moderate to good yields of the pyrimidinones and the intermediates are the merits of the route.

  13. Zr (IV COMPLEXES OF SOME NITROGEN-OXYGEN DONOR LIGANDS (SEMICARBAZONES & SALICYLALDAZINE

    Directory of Open Access Journals (Sweden)

    Z F DAWOOD

    2002-06-01

    Full Text Available Complexes containing mixed ligands of zirconium (IV have been synthesized by the reaction of zirconium (IV nitrate (Zr(NO34, 5H2O with salicylaldazine (SAH2 and semicarbazone ligands benzaldehyde semicarbazone (BSCH, 4-methoxybenzaldehyde semicarbzone (MBSCH, 2-chlorobenzaldehyde semicrbazone (CISCH and cinnamaldehyde semicarbazone (CinSCH forming complexes of the type [Zr2(SAH2(SCH2](NO38 and [Zr2(SA2 (SC2](NO32 in neutral and basic medium respectively. The ligands and their complexes are characterized physico-chemically.

  14. Kinetics of the benzyl + O(3P) reaction: a quantum chemical/statistical reaction rate theory study.

    Science.gov (United States)

    da Silva, Gabriel; Bozzelli, Joseph W

    2012-12-14

    The resonance stabilized benzyl radical is an important intermediate in the combustion of aromatic hydrocarbons and in polycyclic aromatic hydrocarbon (PAH) formation in flames. Despite being a free radical, benzyl is relatively stable in thermal, oxidizing environments, and is predominantly removed through bimolecular reactions with open-shell species other than O(2). In this study the reaction of benzyl with ground-state atomic oxygen, O((3)P), is examined using quantum chemistry and statistical reaction rate theory. C(7)H(7)O energy surfaces are generated at the G3SX level, and include several novel pathways. Transition state theory is used to describe elementary reaction kinetics, with canonical variational transition state theory applied for barrierless O atom association with benzyl. Apparent rate constants and branching ratios to different product sets are obtained as a function of temperature and pressure from solving the time-dependent master equation, with RRKM theory for microcanonical k(E). These simulations indicate that the benzyl + O reaction predominantly forms the phenyl radical (C(6)H(5)) plus formaldehyde (HCHO), with lesser quantities of the C(7)H(6)O products benzaldehyde, ortho-quinone methide, and para-quinone methide (+H), along with minor amounts of the formyl radical (HCO) + benzene. Addition of O((3)P) to the methylene site in benzyl produces a highly vibrationally excited C(7)H(7)O* adduct, the benzoxyl radical, which can β-scission to benzaldehyde + H and phenyl + HCHO. In order to account for the experimental observation of benzene as the major reaction product, a roaming radical mechanism is proposed that converts the nascent products phenyl and HCHO to benzene + HCO. Oxygen atom addition at the ortho and para ring sites in benzyl, which has not been previously considered, is shown to lead to the quinone methides + H; these species are less-stable isomers of benzaldehyde that are proposed as important combustion intermediates, but

  15. New Element Organic Frameworks Based on Sn, Sb, and Bi, with Permanent Porosity and High Catalytic Activity

    Directory of Open Access Journals (Sweden)

    Julia Fritsch

    2010-03-01

    Full Text Available We present new element organic frameworks based on Sn, Sb and Bi atoms connected via organic linkers by element-carbon bonds. The open frameworks are characterized by specific surface areas (BET of up to 445 m2 g-1 and a good stability under ambient conditions resulting from a highly hydrophobic inner surface. They show good performance as heterogeneous catalysts in the cyanosylilation of benzaldehyde as a test reaction. Due to their catalytic activity, this class of materials might be able to replace common homogeneous element-organic and often highly toxic catalysts especially in the food industry.

  16. Synthesis and evaluation of some bioactive compounds having oxygen and nitrogen heteroatom

    Indian Academy of Sciences (India)

    Poonam Yadav; Nalini V Purohit

    2013-01-01

    Some new 3,4-disubstituted isocoumarins were synthesized having bioactive pyrazole molecule at 3rd position of isocoumarin moiety (5a,b), from isocoumarin -3- carboxylic acid hydrazide (4a,b) followed by cyclization with acetyl acetone. A series of isocoumarin derivative having Schiff base as lateral side chain at 3rd position of isocoumarin moiety were also synthesized (7a,b), by condensing isocoumarin acid hydrazide and benzaldehyde derivative followed by dehydration. The chemical structures of all the compounds were determined by analytical and spectral method. The lead compounds were screened for antimicrobial and analgesic activities.

  17. (1S-1,2-O-Benzylidene-α-d-glucurono-6,3-lactone

    Directory of Open Access Journals (Sweden)

    David J. Watkin

    2009-02-01

    Full Text Available X-ray crystallographic analysis has established that the major product from the protection of d-glucoronolactone with benzaldehyde is (1S-1,2-O-benzylidene-α-d-glucurono-6,3-lactone, C13H12O6, rather than the R epimer. The crystal structure exists as O—H...O hydrogen-bonded chains of molecules lying parallel to the a axis. The absolute configuration was determined by the use of d-glucuronolactone as the starting material.

  18. The use of phytochemicals as fumigants for the control of stored product insect pests

    OpenAIRE

    Eli Shaaya; Moshe Kostyukovsky

    2011-01-01

    The current study is aimed to evaluate the potential use of the known isothyiocyanates, as compared to a new isothyiocyanate (ITC) isolated from Eruca sativa (salad rocket) as fumigants for the control of stored product insects. The biological activity of methyl iodide (CH3I), carbon disulphide (CS2), benzaldehyde (C7H6O) and essential oils were also evaluated. The toxicity of the various fumigants was assessed against adults and larvae of a number of major stored product insects. ITCs are kn...

  19. Alternative fumigants to methyl bromide for the control of pest infestation in grain and dry food products

    OpenAIRE

    Shaaya, E.; Kostyukovsky, M.

    2010-01-01

    The primary aim of the current study is to evaluate the potential use of the known isothyiocyanates (ITC) as compared to a new ITC isolated from Eruca sativa (salad rocket) as fumigants for the control of stored products insects. The biological activity of methyl iodide (CH₃I), carbon disulphide (CS₂), benzaldehyde (C₇H₆0) and essential oils were also evaluated. The toxicity of the various fumigants was assessed against adults and larvae of a number of major stored-product insects. ITCs are p...

  20. Investigation of Prins reaction for the synthesis of 2, 4- disubstituted tetrahydropyran derivatives and 1, 3-dioxanes using polyaniline supported acid as reusable catalyst

    Indian Academy of Sciences (India)

    Kalyan Jyoti Borah; Ruli Borah

    2011-09-01

    The Prins cyclization of homoallyl alcohol with a variety of aldehydes were observed under reflux condition in dichloromethane using both polyaniline supported TsOH (PANI-TsOH) and FeCl3 (PANI- FeCl3) as reusable acid catalysts with the formation of 2,4-disubstituted tetrahydropyran ether as single product. In case of 4-, 3- and 2- nitro benzaldehydes, the reaction generated acetal of the aldehyde and homoallylic alcohol as single product. Additionally, both catalysts were investigated for the synthesis of 1, 3-dioxane in dichloromethane under reflux and at ambient temperature.

  1. A multifunctional chemical sensor based on a three-dimensional lanthanide metal-organic framework

    Science.gov (United States)

    Du, Pei-Yao; Liao, Sheng-Yun; Gu, Wen; Liu, Xin

    2016-12-01

    A 3D lanthanide MOF with formula [Sm2(abtc)1.5(H2O)3(DMA)]·H2O·DMA (1) has been successfully synthesized via solvothermal method. Luminescence studies reveal that 1 exhibits dual functional detection benzyl alcohol and benzaldehyde among different aromatic molecules. In addition, 1 displays a turn-on luminescence sensing with respect to ethanol among different alcohol molecules, which suggests that 1 is also a promising luminescent probe for high selective sensing of ethanol.

  2. Solid-phase microextraction for flavor analysis in Harari Khat (Catha edulis) stimulant

    Institute of Scientific and Technical Information of China (English)

    AL-FLAHIAbdulsalam; 邹建凯; 殷学锋

    2004-01-01

    This research examined the typical flavor compounds in the commonest type of Khat called Harari Khat grown in the region of Ethiopia.Twenty-eight compounds, which includes 1,2-Propanedione,1-Phenyl,Hexanol,Hexanal compounds,Limonene, Benzaldehyde with other flavors, were extracted by polydimethylsiloxane at room temperature for 30min from Khat samples,and identified by solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS).This method needs no organic solvents and required minimal sample.

  3. Highly efficient solvent-free synthesis of pyranopyrazoles by a Brønsted-acidic ionic liquid as a green and reusable catalyst

    Indian Academy of Sciences (India)

    Javad Ebrahimi; Ali Mohammadi; Vahid Pakjoo; Esan Bahramzade; Amir Habibi

    2012-09-01

    A simple, green and efficient protocol for synthesis of dihydropyrano[2,3-c]pyrazole derivatives is developed by a four component reaction of various benzaldehydes, ethyl acetoacetate, hydrazine hydrate and malononitrile in the presence of 3-methyl-1-(4-sulphonic acid)butylimidazolium hydrogen sulphate [(CH2)4SO3HMIM][HSO4], an acidic ionic liquid and as a catalyst, under solvent-free conditions. The key advantages of this process are high yields, shorter reaction times, easy work-up, purification of products by non-chromatographic method and the reusability of the catalyst.

  4. Sodium Hydrogen Sulfate as Effective and Reusable Heterogeneous Catalyst for the One-pot Preparation of 14H-[(Un)substituted phenyl]-dibenzo[a,j]xanthene Leuco-dye Derivatives

    Institute of Scientific and Technical Information of China (English)

    SHATERIAN Hamid Reza; DOOSTMOHAMMADI Razieh; GHASHANG Majid

    2008-01-01

    NaHSO4·H2O has been used as an efficient catalyst for the one-pot preparation of 14H-[(un)substituted phenyl]-dibenzo[a,j]xanthene leuco-dye derivatives by condensation of β-naphthol with substituted benzaldehydes under microwave and thermal conditions.This method has the advantages of high yields,a green reaction,an efficient and cost-effective method,simple procedures,short reaction time,and easy workup.

  5. The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

    Science.gov (United States)

    Tajti, Ádám; Ádám, Anna; Csontos, István; Karaghiosoff, Konstantin; Czugler, Mátyás; Ábrányi-Balogh, Péter

    2017-01-01

    Summary A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair.

  6. An investigation of the catalytic potential of potassium cyanide and imidazolium salts for ultrasound-assisted synthesis of benzoin derivatives

    Directory of Open Access Journals (Sweden)

    Javad Safari

    2015-11-01

    Full Text Available A rapid, highly efficient and mild green synthesis of benzoin was performed using substituted benzaldehyde catalyzed by KCN and imidazolium salts in EtOH/H2O under ultrasonic activation. The products were obtained in good yields within short reaction times with N,N′-dialkylimidazolium salts, which were found to be more effective pre-catalysts at room temperature for benzoin condensation in comparison to corresponding cyanide ion in heating method. This simple method affords benzoin derivatives at room temperature in short reaction times with high yield and purity.

  7. Reaction Kinetics for Heterogeneous Oxidation of Mn(Ⅲ) ~Toluene%Mn3+~甲苯非均相体系的氧化反应动力学

    Institute of Scientific and Technical Information of China (English)

    张彰; 朱宪

    2002-01-01

    The reaction kinetics of the heterogeneous oxidation of toluene with Mna + was studied by considering the effects of disproportionation of Mns+ in reaction system, a "parallel" modulus was set up. And then the concentration of Mn3 + in disproportionation and the concentration of benzaldehyde in oxidation were respectively determined in turn, the rate constant, order and pseudo-activation energy of the heterogeneous oxidation were obtained by mathematical deduction and the kinetic equation was concluded. In addition, the reaction mechanism was analyzed. It shows that the results are completely consistent with modulus.

  8. Reaction Kinetics for Heterogeneous Oxidation of Mn(Ⅲ)—Toluene

    Institute of Scientific and Technical Information of China (English)

    张彰; 朱宪

    2002-01-01

    The reaction kinetics of the heterogeneous oxidation oftoluene with Mn3+ was studied by considering the effects of disproportionation of Mn3+ in reaction system,a “parallel”modulus was set up.And then the concentration of Mn3+ in disproportionation and the concentration of benzaldehyde in oxidation were respectively determined in turn.the rate constant,order and pseudo-activation energy of the heterogeneous oxidation were obtained by mathematical deduction and the kinetic equation was concluded.In addition,the reaction mechanism was analyzed.It shows that the results are completely consistent with modulus.

  9. Noninnocent role of N-methyl pyrrolidinone in thiazolidinethione-promoted asymmetric aldol reactions.

    Science.gov (United States)

    Sreenithya, A; Sunoj, Raghavan B

    2012-11-16

    The origin of stereoselectivity in the reaction between α-azido titanium enolate derived from chiral auxiliary N-acyl thiazolidinethione and benzaldehyde is established using the DFT(B3LYP) method. A nonchelated transition state with N-methyl-2-pyrrolidinone (NMP) bound to a TiCl(3) enolate is found to be energetically the most preferred model responsible for the formation of an Evans syn aldol product. The TS model devoid of NMP, although of higher energy, is found to be successful in predicting the right stereochemical outcome.

  10. Reductive heterocyclizations via indium-iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles.

    Science.gov (United States)

    Ahn, Gil Hwan; Lee, Jung June; Jun, Young Moo; Lee, Byung Min; Kim, Byeong Hyo

    2007-08-07

    While N-(2-nitrobenzylidene)anilines produced mixtures of 2,1-benzisoxazoles and 3-anilino-2-aryl-2H-indazoles in the presence of indium and iodine in MeOH, N-(2-nitrobenzylidene)anilines were transformed into 3-anilino-2-aryl-2H-indazoles as the predominant major product through the change of the solvent from protic MeOH to aprotic THF. In an indium-mediated one-pot reductive reaction, 2-benzaldehydes and anilines in THF were also successfully transformed into the corresponding indazoles.

  11. Evaluation of the Hydroxynitrile Lyase Activity in Cell Cultures of Capulin (Prunus serotina)`

    Institute of Scientific and Technical Information of China (English)

    Liliana Hernáindez; Héctor Luna; Arturo Navarro-Oca(n)a; Ma Teresa de Jesús Olivera-Flores; Ivon Ayala

    2008-01-01

    Enzymatic preparations obtained from young plants and cell cultures of capulin were screened for hydroxynitrile lyaseactivity. The thrceweek old plants, grown under sterile conditions, were used to establish a solid cell culture. Crude preparationsobtained from this plant material were evaluated for the transformation of benzaldehyde to the corresponding eyanohydrin(mandelonitrile). The results show that the crude material from roots, stalks, and leaves of young plants and calli of roots, stalks,internodes and petioles biocatalyzed the addition of hydrogen cyanide (HCN) to benzaidehyde with a modest to excellentenantioselectivity.

  12. Synthesis and plant-growth regulatory activities of novel imine derivatives containing 1H-1,2,4-triazole and thiazole rings

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    Eleven new imine derivatives 6 containing 1H-1,2,4-triazole and thiazole rings were synthesized by the condensation of 5-((1H- 1,2,4-triazol-1-yl)methyl)-4-tert-butylthiazol-2-amine with various substituted benzaldehydes.The structures of the title compounds were characterized by ~1H NMR,MS and elemental analysis.The plant-growth regulatory activities of these compounds were evaluated.The primary bioassay results indicated that these target compounds exhibited promising plant-growth regulatory activities...

  13. Productive degradation of the biocide benzylbenzoate by Acinetobacter sp. strain AG1 isolated from the River Elbe.

    Science.gov (United States)

    Göttsching, Anja; Schmidt, Stefan

    2007-04-01

    From water sampled in the River Elbe, we isolated a bacterial strain able to use the biocidal compound benzylbenzoate as its sole source of carbon and energy under aerobic conditions. This isolate was tentatively assigned to the genus Acinetobacter due to its morphological, physiological and partial SSU rRNA gene sequence properties. The productive bacterial degradation of the biocide benzylbenzoate was demonstrated, and the catabolic sequence was elucidated biochemically. Growth experiments, along with enzymatic studies, demonstrated that strain Acinetobacter sp. AG1 hydrolyzed benzylbenzoate enzymatically to yield benzylalcohol and benzoate. Benzylalcohol was further transformed to benzoate via benzaldehyde. Benzoate was subsequently channeled via catechol into the oxoadipate pathway for further degradation.

  14. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONE DERIVATIVES AND THEIR COPPERCOMPLEXES

    Directory of Open Access Journals (Sweden)

    P. M. Rachmale

    2012-03-01

    Full Text Available In the present investigation, 4-chloro acetophenone on condensation with 2-nitro benzaldehydes in methanolic NaOH solution yielded the corresponding chalcone. These chalcone were further reacted with Isonicotyl hydrazide and semicarbazide in ethanol which led to the formation of chalcone Isonicotyl hydrazone and chalcone semicarbazone derivatives respectively. The newly synthesized derivatives and there copper complexes were characterized on the basis of their chemical properties and spectroscopic data such as IR, NMR and UV. All newly synthesized compounds were evaluated for their antibacterial activities against E. coli and S. aureus also for antifungal activities against P. notatum.

  15. First total synthesis of two nematicidal prenylated flavanones

    Institute of Scientific and Technical Information of China (English)

    Jin Hui Yang; Shi Zhi Jiang; Yan Min Zhao; Yun Feng Li; Cong Bin Ji; Wan Yi Liu

    2009-01-01

    The total synthesis of(±)-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one and(±)-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one was first achieved through C-prenylation,protection of phenolic hydroxyl group,aldol condensation,cyclization and deprotection starting from cheap benzaldehyde,4-hydroxybenzaldehyde and 2-hydroxyacetophenone,with total yield of 20 and 16.3%.All structures of new compounds were confirmed by IR,1H NMR and MS.

  16. Catalysis by amino acid-derived tetracoordinate complexes: enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes.

    Science.gov (United States)

    Dangel, B D; Polt, R

    2000-09-21

    Me(2)Zn and Et(2)Zn added to aromatic and aliphatic aldehydes in the presence of 3 mol % of 2. (S)-1-Phenylethanol (91% ee) and (S)-1-phenylpropanol (86% ee) were synthesized from benzaldehyde and (S)-1-furan-2-yl-1-propanol (86% ee) from 2-furaldehyde. Nonanal and 3-phenylpropanal provided (S)-3-undecanol (96% ee) and (S)-1-phenyl-3-pentanol (94% ee). A solid-phase variant was effective with reduced ee's (e.g., 86% ee --> 79% ee) for (S)-1-phenylpropanol.

  17. Fluorescence method for enzyme analysis which couples aromatic amines with aromatic aldehydes

    Science.gov (United States)

    Smith, R.E.; Dolbeare, F.A.

    1980-10-21

    Analysis of proteinases is accomplished using conventional amino acid containing aromatic amine substrates. Aromatic amines such as 4-methoxy-2-naphthylamine (4M2NA), 2-naphthylamine, aminoisophthalic acid dimethyl ester, p-nitroaniline, 4-methoxy-1-aminofluorene and coumarin derivatives resulting from enzymatic hydrolysis of the substrate couples with aromatic aldehydes such as 5-nitrosalicylaldehyde (5-NSA), benzaldehyde and p-nitrobenzaldehyde to produce Schiff-base complexes which are water insoluble. Certain Schiff-base complexes produce a shift from blue to orange-red (visible) fluorescence. Such complexes are useful in the assay of enzymes. No Drawings

  18. Sulfuric Acid ([3-(3-Silicapropyl)sulfanyl]propyl)ester as a Recyclable Catalyst for the Synthesis of 4,4'-(Arylmethylene)bis(1H-pyrazol-5-ols)%Sulfuric Acid ([3-(3-Silicapropyl)sulfanyl]propyl)ester as a Recyclable Catalyst for the Synthesis of4,4'-(Arylmethylene)bis(1H-pyrazol-5-ols)

    Institute of Scientific and Technical Information of China (English)

    Shekoofeh TAYEBI; Mojtaba BAGHERNEJAD; Dariush SABERI; Khodabakhsh NI KNAM

    2011-01-01

    Sulfuric acid ([3-(3-silicapropyl)sulfanyl]propyl)ester is employed as a recyclable catalyst for the condensation reaction between aromatic aldehydes and 3-methyl-l-phenyl-5-pyrazolone.This condensation reaction was performed in ethanol under refluxing conditions giving 4,4-alkylmethylene-bis(3-methyl-5-pyrazolones) in 74-90% yields.The heterogeneous catalyst was recycled and used in eleven runs for the reaction between benzaldehyde and 3-methyl-l-phenyl-5-pyrazolone without losing catalytic activity.

  19. Characterization of HMPA-Coordinated Titanium(III) Species in Solutions of Zinc-Reduced Titanocene Dihalides

    DEFF Research Database (Denmark)

    Larsen, Jens; Juel Enemærke, Rasmus; Daasbjerg, Kim

    2006-01-01

    The effect of adding HMPA to THF solutions of metal-reduced titanocene dihalides (Cp2TiX2) has been investigated by means of cyclic voltammetry and kinetic measurements. It is shown that the high coordination affinity of HMPA toward the titanium nucleus results in the formation of a mixture...... correlation is observed between the HMPA concentration and the rate of reduction of electrophiles such as benzyl chloride and benzaldehyde. This indicates that the reactive reagents in solution remain the uncoordinated TiIII species despite them being in low concentrations. In keeping with this interpretation...

  20. Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl E 2-propen-1-ones

    Science.gov (United States)

    Sathiyamoorthi, K.; Mala, V.; Sakthinathan, S. P.; Kamalakkannan, D.; Suresh, R.; Vanangamudi, G.; Thirunarayanan, G.

    2013-08-01

    Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic data. The spectral frequencies of synthesised substituted styryl 4-iodophenyl ketones have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of 4-iodophenyl chalcones have been studied using Bauer-Kirby method.

  1. Organic materials with nonlinear optical properties

    Science.gov (United States)

    Stupp, Samuel I.; Son, Sehwan; Lin, Hong-Cheu

    1995-01-01

    The present invention is directed to organic materials that have the ability to double or triple the frequency of light that is directed through the materials. Particularly, the present invention is directed to the compound 4-[4-(2R)-2-cyano-7-(4'-pentyloxy-4-biphenylcarbonyloxy)phenylheptylidene) phenylcarbonyloxy]benzaldehyde, which can double the frequency of light that is directed through the compound. The invention is also directed to the compound (12-hydroxy-5,7-dodecadiynyl) 4'-[(4'-pentyloxy-4-biphenyl)carbonyloxy]-4-biphenylcarboxylate, and its polymeric form. The polymeric form can triple the frequency of light directed through it.

  2. Preparation, characterization and catalytic properties of MCM-48 supported tungstophosphoric acid mesoporous materials for green synthesis of benzoic acid

    Science.gov (United States)

    Wu, Hai-Yan; Zhang, Xiao-Li; Chen, Xi; Chen, Ya; Zheng, Xiu-Cheng

    2014-03-01

    MCM-48 and tungstophosphoric acid (HPW) were prepared and applied for the synthesis of HPW/MCM-48 mesoporous materials. The characterization results showed that HPW/MCM-48 obtained retained the typical mesopore structure of MCM-48, and the textural parameters decreased with the increase loading of HPW. The catalytic oxidation results of benzyl alcohol and benzaldehyde with 30% H2O2 indicated that HPW/MCM-48 was an efficient catalyst for the green synthesis of benzoic acid. Furthermore, 35 wt% HPW/MCM-48 sample showed the highest activity under the reaction conditions.

  3. Catalyst system and process for benzyl ether fragmentation and coal liquefaction

    Science.gov (United States)

    Zoeller, Joseph Robert

    1998-04-28

    Dibenzyl ether can be readily cleaved to form primarily benzaldehyde and toluene as products, along with minor amounts of bibenzyl and benzyl benzoate, in the presence of a catalyst system comprising a Group 6 metal, preferably molybdenum, a salt, and an organic halide. Although useful synthetically for the cleavage of benzyl ethers, this cleavage also represents a key model reaction for the liquefaction of coal; thus this catalyst system and process should be useful in coal liquefaction with the advantage of operating at significantly lower temperatures and pressures.

  4. Fluorescence method for enzyme analysis which couples aromatic amines with aromatic aldehydes

    Science.gov (United States)

    Smith, Robert E.; Dolbeare, Frank A.

    1979-01-01

    Analysis of proteinases is accomplished using conventional amino acid containing aromatic amine substrates. Aromatic amines such as 4-methoxy-2-naphthylamine (4M2NA), 2-naphthylamine, aminoisophthalic acid dimethyl ester, p-nitroaniline, 5-methoxy-1-aminofluorene and coumarin derivatives resulting from enzymatic hydrolysis of the substrate couples with aromatic aldehydes such as 5-nitrosalicylaldehyde (5-NSA), benzaldehyde and p-nitrobenzaldehyde to produce Schiff-base complexes which are water insoluble. Certain Schiff-base complexes produce a shift from blue to orange-red (visible) fluorescence. Such complexes are useful in the assay of enzymes.

  5. An Efficient Preparation of 1,2-Diamino-1-phenylheptane

    Directory of Open Access Journals (Sweden)

    P. T. Perumal

    2002-06-01

    Full Text Available A convenient four-step method for the preparation of the lipophilic vicinal diamine 1,2-diamino-1-phenylheptane is described. Condensation involving octan-2-one, benzaldehyde and ammonia is reported. Regioselective Schmidt rearrangement of 2,6-diphenyl-3-pentyl-piperidin-4-one (1 to 2,7-diphenyl-3-pentyl hexahydrodiazapin-5-one (3 is presented. Hydrolysis of 2,7-diphenyl-3-pentyl hexahydrodiazapin-5-one to 1,2-diamino-1-phenylheptane (4 is also reported for the first time.

  6. Active Sites on the Surface of Nano-Sized SiO2-TiO2 Composites

    Science.gov (United States)

    Valova, M. S.; Koryakova, O. V.; Maksimovskikh, A. I.; Fedorova, O. V.; Murashkevich, A. N.; Alisienok, O. A.

    2014-07-01

    The nature and amount of active sites on the surface of nano-sized SiO2-TiO2 oxides were studied by FTIR spectroscopy and back-titration methods. Increasing the TiO2 content in the SiO2-TiO2 composites increased the amount of activated surface H2O and adsorbed CO2. This increased the amount of active basic centers on the oxide surface and caused the first of two observed mechanisms for benzaldehyde adsorption (with and without its activation) to begin to prevail.

  7. Derivative couplings between TDDFT excited states obtained by direct differentiation in the Tamm-Dancoff approximation

    Science.gov (United States)

    Ou, Qi; Fatehi, Shervin; Alguire, Ethan; Shao, Yihan; Subotnik, Joseph E.

    2014-07-01

    Working within the Tamm-Dancoff approximation, we calculate the derivative couplings between time-dependent density-functional theory excited states by assuming that the Kohn-Sham superposition of singly excited determinants represents a true electronic wavefunction. All Pulay terms are included in our derivative coupling expression. The reasonability of our approach can be established by noting that, for closely separated electronic states in the infinite basis limit, our final expression agrees exactly with the Chernyak-Mukamel expression (with transition densities from response theory). Finally, we also validate our approach empirically by analyzing the behavior of the derivative couplings around the {T}1/{T}2 conical intersection of benzaldehyde.

  8. N-(2,4-Dinitrophenyl-N′-[nitro(phenylmethylene]hydrazine

    Directory of Open Access Journals (Sweden)

    Chunlan Yuan

    2008-12-01

    Full Text Available The title compound, C13H9N5O6, contains three nitro groups. It is prepared by the reaction of benzaldehyde 2,4-dinitrophenylhydrazone with nitric oxide at ambient temperature. The imine group is nearly coplanar with the (2,4-dinitrophenylhydrazine unit. The second benzene ring and the third nitro group are twisted away from this plane, with dihedral angles of 48.5 (3 and 15.2 (3°, respectively. Weak intramolecular N—H...O interactions are observed.

  9. Fabrication of liquid crystal based sensor for detection of hydrazine vapours

    Science.gov (United States)

    Nandi, Rajib; Singh, Sachin Kumar; Singh, Hemant Kumar; Singh, Bachcha; Singh, Ranjan K.

    2014-10-01

    A novel liquid crystal (LC) based sensor to detect trace level amount of hydrazine vapour has been developed. The LC 4‧-pentyl-4-biphenylcarbonitrile (5CB) doped with 0.5 wt% 4-decyloxy benzaldehyde (DBA) shows dark to bright optical texture upon exposure of hydrazine vapours as revealed by polarizing optical microscopy under crossed polarizers. The hydrazine interacts with the doped DBA and form diimine compound which disrupt the orientation of aligned 5CB. The interaction between DBA and hydrazine has been also studied by Raman spectroscopy.

  10. Chemical defense in the cave-dwelling millipede Brachydesmus troglobius Daday, 1889 (Diplopoda, Polydesmidae

    Directory of Open Access Journals (Sweden)

    Makarov Slobodan E.

    2012-01-01

    Full Text Available The troglomorphic millipede Brachydesmus troglobius Daday, 1889 (Polydesmida: Polydesmidae secretes allomones from glands on both lateral surfaces of its body segments. The secretion was identified by gas chromatography-mass spectrometry (GC-MS analysis with electron and chemical ionization, and was shown to be composed of a mixture of benzaldehyde, benzyl alcohol, benzoylnitrile, benzoic acid and mandelonitrile benzoate. Hydrogen cyanide was qualitatively identified by the picric acid test. This is the first identification of these compounds in a cave-dwelling polydesmid.

  11. Unexpectedly Facile Rh(I) Catalyzed Polymerization of Ethynylbenzaldehyde Type Monomers: Synthesis of Polyacetylenes Bearing Reactive and Easy Transformable Pendant Carbaldehyde Groups.

    Science.gov (United States)

    Sedláček, Jan; Havelková, Lucie; Zedník, Jiří; Coufal, Radek; Faukner, Tomáš; Balcar, Hynek; Brus, Jiří

    2017-02-23

    The chain coordination polymerization of (ethynylarene)carbaldehydes with unprotected carbaldehyde groups, namely ethynylbenzaldehydes, 1-ethynylbenzene-3,5-dicarboxaldehyde, and 3-[(4-ethynylphenyl)ethynyl]benzaldehyde, is reported for the first time. Polymerization is catalyzed with various Rh(I) catalysts and yields poly(arylacetylene)s with one or two pendant carbaldehyde groups per monomeric unit. Surprisingly, the carbaldehyde groups of the monomers do not inhibit the polymerization unlike the carbaldehyde group of unsubstituted benzaldehyde that acts as a strong inhibitor of Rh(I) catalyzed polymerization of arylacetylenes. The inhibition ability of carbaldehyde groups in (ethynylarene)carbaldehydes seems to be eliminated owing to a simultaneous presence of unsaturated ethynyl groups in (ethynylarene)carbaldehydes. The reactive carbaldehyde groups make poly[(ethynylarene)carbaldehyde]s promising for functional appreciation via various postpolymerization modifications. The introduction of photoluminescence or chirality to poly(ethynylbenzaldehyde)s via quantitative modification of their carbaldehyde groups in reaction with either photoluminescent or chiral primary amines under formation of the polymers with Schiff-base-type pendant groups is given as an example.

  12. Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases.

    Science.gov (United States)

    Singh, A K; Pandey, O P; Sengupta, S K

    2012-01-01

    New Zn(II) complexes have been synthesized by the reactions of zinc(II) acetate with Schiff bases derived from 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde, 2-hydroxyacetophenone or indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non-electrolytes. Elemental analyses suggest that the complexes have 1:1 stoichiometry of the type [ZnL(H(2)O)(2)], [ZnL'(OAc)(2)(H(2)O)(2)] (L=dianionic Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and 2-hydroxyacetophenone or indoline-2,3-dione; L'=neutral Schiff bases derived from 3-(substituted phenyl)-4-amino-5-hydrazino-1, 2, 4-triazole and benzaldehyde) and they were characterized by FT-IR, (1)H NMR, (13)C NMR and FAB mass. All these Schiff bases and their complexes have also been screened for their antibacterial activities against Bacillus subtilis, Escherichia coli and antifungal activities against Colletotrichum falcatum, Aspergillus niger, Fusarium oxysporium and Carvularia pallescence by petriplates methods.

  13. Cytotoxic conjugates of betulinic acid and substituted triazoles prepared by Huisgen Cycloaddition from 30-azidoderivatives

    Science.gov (United States)

    Sidova, Veronika; Zoufaly, Pavel; Pokorny, Jan; Dzubak, Petr; Hajduch, Marian; Popa, Igor

    2017-01-01

    In this work, we describe synthesis of conjugates of betulinic acid with substituted triazoles prepared via Huisgen 1,3-cycloaddition. All compounds contain free 28-COOH group. Allylic bromination of protected betulinic acid by NBS gave corresponding 30-bromoderivatives, their substitution with sodium azides produced 30-azidoderivatives and these azides were subjected to CuI catalysed Huisgen 1,3-cycloaddition to give the final conjugates. Reactions had moderate to high yields. All new compounds were tested for their in vitro cytotoxic activities on eight cancer and two non-cancer cell lines. The most active compounds were conjugates of 3β-O-acetylbetulinic acid and among them, conjugate with triazole substituted by benzaldehyde 9b was the best with IC50 of 3.3 μM and therapeutic index of 9.1. Five compounds in this study had IC50 below 10 μM and inhibited DNA and RNA synthesis and caused block in G0/G1 cell cycle phase which is highly similar to actinomycin D. It is unusual that here prepared 3β-O-acetates were more active than compounds with the free 3-OH group and this suggests that this set may have common mechanism of action that is different from the mechanism of action of previously known 3β-O-acetoxybetulinic acid derivatives. Benzaldehyde type conjugate 9b is the best candidate for further drug development. PMID:28158265

  14. Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity.

    Science.gov (United States)

    Pingaew, Ratchanok; Mandi, Prasit; Nantasenamat, Chanin; Prachayasittikul, Supaluk; Ruchirawat, Somsak; Prachayasittikul, Virapong

    2014-06-23

    A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) revealed that many substituted triazole analogs of benzoates (20, 29) and benzaldehydes (30, 32) exhibited anticancer activity against all of the tested cancer cell lines in which the ester analog 20 was shown to be the most potent compound against HuCCA-1 (IC50 = 0.63 μM) and A549 (IC50 = 0.57 μM) cell lines. Triazoles bearing phenyl (15, 24), tolyl (26, 27), acetophenone (19), benzoate (20, 29), benzaldehyde (21, 30) and naphthalenyl (25) substituents showed stronger anticancer activity against HepG2 cells than that of the etoposide. Interestingly, the p-tolyl analog (27) displayed the most potent inhibitory activity (IC50 = 0.56 μM) against HepG2 cells without affecting normal cells. Of the investigated tetrahydroisoquinoline-triazoles, the promising compounds 20 and 27 were selected for molecular docking against AKR1C3, which was identified to be a plausible target site.

  15. Chalcogenated Schiff bases: Complexation with palladium(II) and Suzuki coupling reactions

    Indian Academy of Sciences (India)

    Pradhumn Singh; G K Rao; Mohd Salman Karim; Ajai K Singh

    2012-11-01

    Chalcogenated Schiff bases of 5-chloroisatin (L1-L3), 2-(methythio)benzaldehyde (L4), 2-acetylpyridine (L5) and benzaldehyde (L6-L7) have been synthesized. Both the carbonyl groups of 5- chloroisatin appear to be reactive (noticed for the first time) for making >C=N bond, of course one at a time only. The 1H, 13C{1H}, 77Se{1H} and 125Te{1H} NMR spectroscopy have been used to establish the coexistence of two products, which were found in the ratio 53:47 (E = S), 55:45 (E = Se) and 81:19 (E = Te). The larger amount is of the one in which C=O group away from NH is derivatized. The two products are not separable. Palladium complexes (1-4) of Schiff bases of other three aldehydes were synthesized. The ligands as well as complexes were characterized by multinuclear NMR spectroscopy. The crystal structures of [Pd(L4/L5)Cl][ClO4] (1/2) have been solved. The Pd-Se bond lengths are 2.4172(17) and 2.3675(4) Å, respectively for 1 and 2. The Pd-complexes (3-4) of L6-L7 were explored for Suzuki-Miyaura coupling and found promising as 0.006 mol % of 3 is sufficient to obtain good conversion with TON up to 1.58 × 104.

  16. Near-infrared light controlled photocatalytic activity of carbon quantum dots for highly selective oxidation reaction.

    Science.gov (United States)

    Li, Haitao; Liu, Ruihua; Lian, Suoyuan; Liu, Yang; Huang, Hui; Kang, Zhenhui

    2013-04-21

    Selective oxidation of alcohols is a fundamental and significant transformation for the large-scale production of fine chemicals, UV and visible light driven photocatalytic systems for alcohol oxidation have been developed, however, the long wavelength near infrared (NIR) and infrared (IR) light have not yet fully utilized by the present photocatalytic systems. Herein, we reported carbon quantum dots (CQDs) can function as an effective near infrared (NIR) light driven photocatalyst for the selective oxidation of benzyl alcohol to benzaldehyde. Based on the NIR light driven photo-induced electron transfer property and its photocatalytic activity for H2O2 decomposition, this metal-free catalyst could realize the transformation from benzyl alcohol to benzaldehyde with high selectivity (100%) and conversion (92%) under NIR light irradiation. HO˙ is the main active oxygen specie in benzyl alcohol selective oxidative reaction confirmed by terephthalic acid photoluminescence probing assay (TA-PL), selecting toluene as the substrate. Such metal-free photocatalytic system also selectively converts other alcohol substrates to their corresponding aldehydes with high conversion, demonstrating a potential application of accessing traditional alcohol oxidation chemistry.

  17. Synthesize and characterize of Ag{sub 3}VO{sub 4}/TiO{sub 2} nanorods photocatalysts and its photocatalytic activity under visible light irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Zou, Xuejun [Department of Environmental Science and Technology, Dalian Nationalities University, Dalian 116600 (China); Dong, Yuying, E-mail: dongy@dlnu.edu.cn [Department of Environmental Science and Technology, Dalian Nationalities University, Dalian 116600 (China); Zhang, Xiaodong, E-mail: fatzhxd@126.com [Environment and Low-Carbon Research Center, School of Environment and Architecture, University of Shanghai for Science and Technology, Shanghai 200093 (China); Cui, Yubo [Department of Environmental Science and Technology, Dalian Nationalities University, Dalian 116600 (China)

    2016-03-15

    Graphical abstract: - Highlights: • Ag{sub 3}VO{sub 4}/TiO{sub 2} nanorods were prepared by sol–gel with hydrothermal method. • Toluene removal efficiency was 70% in 4 h using the Ag{sub 3}VO{sub 4}/TiO{sub 2}. • Benzyl alcohol and benzaldehyde were intermediates, and partially mineralized. - Abstract: In this paper, in order to expand the light response range of TiO{sub 2}, Ag{sub 3}VO{sub 4}/TiO{sub 2} nanorods photocatalysts were fabricated by a simple sol–gel method with microwave and hydrothermal method. The as-prepared samples were characterized by XRD, SEM, DRS, XPS and N{sub 2} adsorption–desorption. Meanwhile, their photocatalytic properties were investigated by the degradation of toluene under visible light irradiation. The degradation conversation of toluene had gotten to about 70% in 1% Ag{sub 3}VO{sub 4}/TiO{sub 2} nanorods after reaction 4 h. The predominant photocatalytic activity can be attributed to its strong absorption in visible light region and excellent charge separation characteristics. By using in situ FTIR, benzyl alcohol and benzaldehyde species could be observed during the reaction and the formed intermediates would be partially oxidized into CO{sub 2} and H{sub 2}O. Electron spin resonance confirmed that OH· and O{sub 2}·{sup −} were involved in the photocatalytic degradation of toluene.

  18. Synthesis, characterization and catechol oxidase biomimetic catalytic activity of cobalt(II and copper(II complexes containing N2O2 donor sets of imine ligands

    Directory of Open Access Journals (Sweden)

    Mohamed I. Ayad

    2016-11-01

    Full Text Available New tetradentate imine ligands are derived from Schiff base condensation in a 1:2 molar ratio of the 1,2,4,5-tetra-amino benzene with 2-hydroxy benzaldehyde, (L1, 2,4-dihydroxy benzaldehyde (L2 and 2-hydroxy naphthaldehyde (L3. These ligands react with CoCl2 and CuCl2 in refluxing ethanol to yield a series of cobalt(II and copper(II complexes of the type [M2IILn] nH2O. The structure of the obtained ligands and their metal(II complexes were characterized by various physicochemical techniques, viz. elemental analysis, molar conductance, magnetic susceptibility measurements, thermal analysis (TGA & DTG, IR, electronic absorption and ESR spectral studies. Four-coordinate tetrahedral and square–planar structures were proposed for cobalt(II and copper(II complex species respectively. The ability of the synthesized complexes to catalyze the aerobic oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC to the light absorbing 3,5-di-tert-butylquinone (3,5-DTBQ has been investigated. The results obtained show that all complexes catalyze this oxidation reaction and slight variations in the rate were observed. The probable mechanistic implications of the catalytic oxidation reactions are discussed.

  19. Nutritional Value and Volatile Compounds of Black Cherry (Prunus serotina Seeds

    Directory of Open Access Journals (Sweden)

    Leticia García-Aguilar

    2015-02-01

    Full Text Available Prunus serotina (black cherry, commonly known in Mexico as capulín, is used in Mexican traditional medicine for the treatment of cardiovascular, respiratory, and gastrointestinal diseases. Particularly, P. serotina seeds, consumed in Mexico as snacks, are used for treating cough. In the present study, nutritional and volatile analyses of black cherry seeds were carried out to determine their nutraceutical potential. Proximate analysis indicated that P. serotina raw and toasted seeds contain mostly fat, followed by protein, fiber, carbohydrates, and ash. The potassium content in black cherry raw and toasted seeds is high, and their protein digestibility-corrected amino acid scores suggest that they might represent a complementary source of proteins. Solid phase microextraction and gas chromatography/flame ionization detection/mass spectrometry analysis allowed identification of 59 and 99 volatile compounds in the raw and toasted seeds, respectively. The major volatile compounds identified in raw and toasted seeds were 2,3-butanediol and benzaldehyde, which contribute to the flavor and odor of the toasted seeds. Moreover, it has been previously demonstrated that benzaldehyde possesses a significant vasodilator effect, therefore, the presence of this compound along with oleic, linoleic, and α-eleostearic fatty acids indicate that black cherry seeds consumption might have beneficial effects on the cardiovascular system.

  20. (R)-PAC biosynthesis in [BMIM][PF₆]/aqueous biphasic system using Saccharomyces cerevisiae BY4741 cells.

    Science.gov (United States)

    Kandar, Smita; Suresh, A K; Noronha, Santosh B

    2015-02-01

    (R)-phenylacetylcarbinol or (R)-PAC is a pharmaceutical precursor of (1R, 2S) ephedrine and (1S, 2S) pseudoephedrine. Biotransformation of benzaldehyde and glucose by pyruvate decarboxylase produces (R)-PAC. This biotransformation suffers from toxicity of the substrate, product [(R)-PAC] and by-product (benzyl alcohol). In the present study, ionic liquid/aqueous biphasic system was employed to enhance (R)-PAC production. Fermented broth was the reaction medium in which Saccharomyces cerevisiae BY4741 was the source of pyruvate decarboxylase. Hydrophobic ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) was the non-aqueous phase in which toxic compounds reside. Biocompatibility of [BMIM][PF6] and adequate distribution coefficients of benzaldehyde, (R)-PAC and benzyl alcohol were determined. A Box-Behnken design and response surface methodology were used for the optimization of biotransformation variables in order to maximize (R)-PAC yield and productivity. The results showed higher (R)-PAC yield and productivity of ∼1.5-fold each in the biphasic biotransformation of phase volume ratio 0.05 as compared to the monophasic (conventional) biotransformation. Moreover, the level of major by-product benzyl alcohol was also 3.5-fold lower in biphasic biotransformation. [BMIM][PF6]/aqueous biphasic system is a new approach which could intensify the (R)-PAC production.

  1. The stability studies and in vitro hepatic microsomal metabolism of some alpha-phenyl-N-substituted nitrones in rats.

    Science.gov (United States)

    Bulut, Gülen; Oktav, Mehmet; Ulgen, Mert

    2004-01-01

    Nitrones are a very important class of synthetic chemicals as synthetic intermediates, antioxidant agents, and metabolic oxidation products of secondary amines and imines used drug, food, cosmetic and printing industry. In the present study, the stability experiments and in vitro metabolism studies using rat microsomal preparations fortified with NADPH were carried out using three different alpha-phenyl-N-substituted nitrones ie alpha-phenyl-N-tert-butylnitrone (PTBN), alpha-(2,6-dichlorophenyl)-N-phenylnitrone (DCPPN) and alpha-phenyl-N-adamantanylnitrone (PADN). The separation of these compounds from the potential degradation, isomerization and metabolic products were performed using a reverse phase HPLC system with a diodearray uv detection. Following stability experiments at 37 degrees C using methanolic nitrone solutions, it was observed that PTBN produced trace amounts of benzaldehyde and the corresponding amide. DCPPN also produced trace amounts of amide. After 12 hours, the amount of the amide significantly increased. PADN produced trace amount of benzaldehyde but not any amide. The proposed compounds were incubated with rat microsomal preparations fortified with NADPH, extracted into dichloromethane (DCM) and finally evaporated under nitrogen in the dark conditions. PTBN was metabolized into corresponding amide whereas DCPPN and PADN did not. With all of the substrates, the corresponding aldehydes are observed with both test and control tubes using denaturated microsomes and without co-factors.

  2. Inhibitory effects of Ruta graveolens L. extract on guinea pig liver aldehyde oxidase.

    Science.gov (United States)

    Pirouzpanah, Saieed; Saieed, Pirouzpanah; Rashidi, Mohammad Reza; Reza, Rashidi Mohammad; Delazar, Abbas; Abbas, Delazar; Razavieh, Seyyed-Vali; Seyyedvali, Razavieh; Hamidi, Aliasghar; Aliasghar, Hamidi

    2006-01-01

    Ruta graveolens L. is a flavonoid-containing medicinal plant with various biological properties. In the present study, the effects of R. graveolens extract on aldehyde oxidase, a molybdenum hydroxylase, are investigated. Aldehyde oxidase was partially purified from liver homogenates of mature male guinea pigs by heat treatment and ammonium sulphate precipitation. The total extract was obtained by macerating the aerial parts of R. graveolens in MeOH 70% and the effect of this extract on the enzyme activity was assayed using phenanthridine, vanillin and benzaldehyde as substrates. Quercetin and its glycoside form, rutin were isolated, purified and identified from the extract and their inhibitory effects on the enzyme were investigated. R. graveolens extract exhibited a high inhibition on aldehyde oxidase activity (89-96%) at 100 microg/ml which was comparable with 10 microM of menadione, a specific potent inhibitor of aldehyde oxidase. The IC50 values for the inhibitory effect of extract against the oxidation of benzaldehyde, vanillin and phenanthridine were 10.4, 10.1, 43.2 microg/ml, respectively. Both quercetin and rutin at 10 microM caused 70-96% and 27-52% inhibition on the enzyme activity, respectively. Quercetin was more potent inhibitor than rutin, but both flavonols exerted their inhibitory effects mostly in a linear mixed-type.

  3. Effects of Oxygen Transfer Limitation and Kinetic Control on Biomimetic Catalytic Oxidation of Toluene

    Institute of Scientific and Technical Information of China (English)

    罗伟平; 刘大为; 孙俊; 邓伟; 盛文兵; 刘强; 郭灿城

    2014-01-01

    Under oxygen transfer limitation and kinetic control, liquid-phase catalytic oxidation of toluene over metalloporphyrin was studied. An improved technique of measuring dissolved oxygen levels for gas-liquid reaction at the elevated temperature and pressure was used to take the sequential data in the oxidation of toluene catalyzed by metalloporphyrin. By this technique the corresponding control step of toluene oxidation could be obtained by varying reaction conditions. When the partial pressure of oxygen in the feed is lower than or equal to 0.070 MPa at 463 K, the oxidation of toluene would be controlled by oxygen transfer, otherwise the reaction would be controlled by kinetics. The effects of both oxygen transfer and kinetic control on the toluene conversion and the selectivity of benzaldehyde and benzyl alcohol in biomimetic catalytic oxidation of toluene were systematically investigated. Three conclusions have been made from the experimental results. Firstly, under the oxygen transfer limitation the toluene conversion is lower than that under kinetic control at the same oxidation conditions. Secondly, under the oxygen transfer limitation the total selectivity of benzaldehyde and benzyl alcohol is lower than that under kinetic control with the same conversion of toluene. Finally, under the kinetics control the oxidation rate of toluene is zero-order with respect to oxygen. The experimental results are identical with the biomimetic catalytic mechanism of toluene oxidation over metalloporphyrins.

  4. Synthesis of cobalt-containing mesoporous catalysts using the ultrasonic-assisted "pH-adjusting" method: Importance of cobalt species in styrene oxidation

    Science.gov (United States)

    Li, Baitao; Zhu, Yanrun; Jin, Xiaojing

    2015-01-01

    Cobalt-containing SBA-15 and MCM-41 (Co-SBA-15 and Co-MCM-41) mesoporous catalysts were prepared via ultrasonic-assisted "pH-adjusting" technique in this study. Their physiochemical structures were comprehensively characterized and correlated with catalytic activity in oxidation of styrene. The nature of cobalt species depended on the type of mesoporous silica as well as pH values. The different catalytic performance between Co-SBA-15 and Co-MCM-41 catalysts originated from cobalt species. Cobalt species were homogenously incorporated into the siliceous framework of Co-SBA-15 in single-site Co(II) state, while Co3O4 particles were loaded on Co-MCM-41 catalysts. The styrene oxidation tests showed that the single-site Co(II) state was more beneficial to the catalytic oxidation of styrene. The higher styrene conversion and benzaldehyde selectivity over Co-SBA-15 catalysts were mainly attributed to single-site Co(II) state incorporated into the framework of SBA-15. The highest conversion of styrene (34.7%) with benzaldehyde selectivity of 88.2% was obtained over Co-SBA-15 catalyst prepared at pH of 7.5, at the mole ratio of 1:1 (styrene to H2O2) at 70 °C.

  5. Modified calcium oxide as stable solid base catalyst for Aldol condensation reaction

    Indian Academy of Sciences (India)

    Ying Tang; Jingfang Xu; Xuefan Gu

    2013-03-01

    A highly efficient and stable solid-base catalyst for Aldol condensation was prepared by modifying commercial CaO with benzyl bromide in a simple way. It was found that modified CaO can effectively catalyse the Aldol condensation of cyclohexanone and benzaldehyde, as well as various benzaldehydes, to produce 2-benzylidenecyclohexanone with a good selectivity and high yield. Higher yield of 95.8% was obtained over modified CaO after 3 h, which is short compared with the yield of 92.1% after 12 h over commercial CaO. The influence of several reaction parameters, such as temperature, catalyst loading, was investigated. The humidity test over modified CaO reveals that the basic centres of modified CaO are stable for CO2 and moisture. From the results of Fourier transform-infrared (FT-IR) and Thermogravity analysis (TG) characterization, the modifier was bonded on surface of CaO chemically and almost no Ca(OH)2 formed during the modification process. The type of aldehyde has great influence on the yield of aldol condensation.

  6. Ring expansion reactions of pentaphenylborole with dipolar molecules as a route to seven-membered boron heterocycles.

    Science.gov (United States)

    Huang, Kexuan; Martin, Caleb D

    2015-02-16

    Reactions of pentaphenylborole with isocyanates, benzophenone, and benzaldehyde produced new seven-membered heterocycles in high yields. For 1-adamantyl isocyanate, a BNC5 heterocycle was obtained from the insertion of the C-N moiety into the five-membered borole, whereas for 4-methoxyphenyl isocyanate, a BOC5 heterocycle was generated from the insertion of the C-O unit. These reactions are believed to occur via a mechanism wherein coordination of the nucleophile to the borole (1-adamantyl, N-coordination or O-coordination for 4-methoxyphenyl) is followed by ring expansion to afford the observed seven-membered heterocycles. The selectivity to form B-O- or B-N-containing heterocycles is based on the polarization of the isocyanate implying tunable reactivity for the system. Having observed that isocyanates react as 1,2-dipoles with pentaphenylborole, we examined benzophenone and benzaldehyde, which both reacted to insert C-O units into the ring. This represents a new efficient method for preparing rare seven-membered boracycles.

  7. New anthracene-based Schiff bases: Theoretical and experimental investigations of photophysical and electrochemical properties

    Science.gov (United States)

    Sek, Danuta; Siwy, Mariola; Grucela, Marzena; Małecki, Grzegorz; Nowak, Elżbieta M.; Lewinska, Gabriela; Santera, Jerzy; Laba, Katarzyna; Lapkowski, Mieczyslaw; Kotowicz, Sonia; Schab-Balcerzak, Ewa

    2017-03-01

    The new Schiff bases bearing anthracene unit were synthesized from 2-aminoanthracene and various aldehydes such as: benzaldehyde, 4-(diphenylamino)benzaldehyde, 9-phenanthrenecarboxaldehyde, 9-anthracenecarboxaldehyde, and biphenyl-4-carboxaldehyde, 2-naphthaldehyde. Resulted azomethines were characterized by IR, NMR (1H and 13C), elemental analysis and UV-vis spectroscopy. The imine consists of anthracene and biphenyl moieties exhibited liquid crystal properties and their nematic phase showed Schlieren texture. The photoluminescence measurements carried out in solution and in solid state as blend with PMMA revealed the ability of the imines to emission of the blue light with quantum yield efficiency in the range of 2.18-6.03% in blend. Based on the electrochemical experiment they showed value of energy gap (Eg) in the range of 2.5-2.7 eV. Additionally, density functional theory (DFT) was applied for calculations of both electronic structure and spectroscopic properties of synthesized Schiff bases. Moreover, the results obtained from preliminary tests of application of the azomethines in organic photovoltaic (OPV) devices confirmed their electron acceptor character.

  8. Inositol 1,4,5-trisphosphate signalling regulates the avoidance response to nose touch in Caenorhabditis elegans.

    Directory of Open Access Journals (Sweden)

    Denise S Walker

    2009-09-01

    Full Text Available When Caenorhabditis elegans encounters an unfavourable stimulus at its anterior, it responds by initiating an avoidance response, namely reversal of locomotion. The amphid neurons, ASHL and ASHR, are polymodal in function, with roles in the avoidance responses to high osmolarity, nose touch, and both volatile and non-volatile repellents. The mechanisms that underlie the ability of the ASH neurons to respond to such a wide range of stimuli are still unclear. We demonstrate that the inositol 1,4,5-trisphosphate receptor (IP(3R, encoded by itr-1, functions in the reversal responses to nose touch and benzaldehyde, but not in other known ASH-mediated responses. We show that phospholipase Cbeta (EGL-8 and phospholipase Cgamma (PLC-3, which catalyse the production of IP(3, both function upstream of ITR-1 in the response to nose touch. We use neuron-specific gene rescue and neuron-specific disruption of protein function to show that the site of ITR-1 function is the ASH neurons. By rescuing plc-3 and egl-8 in a neuron-specific manner, we show that both are acting in ASH. Imaging of nose touch-induced Ca(2+ transients in ASH confirms these conclusions. In contrast, the response to benzaldehyde is independent of PLC function. Thus, we have identified distinct roles for the IP(3R in two specific responses mediated by ASH.

  9. Aldol Reactions of Axially Chiral 5-Methyl-2-(o-arylimino-3-(o-aryl-thiazolidine-4-ones

    Directory of Open Access Journals (Sweden)

    Sule Erol Gunal

    2016-06-01

    Full Text Available Axially chiral 5-methyl-2-(o-arylimino-3-(o-aryl-thiazolidine-4-ones have been subjected to aldol reactions with benzaldehyde to produce secondary carbinols which have been found to be separable by HPLC on a chiral stationary phase. Based on the reaction done on a single enantiomer resolved via a chromatographic separation from a racemic mixture of 5-methyl-2-(α-naphthylimino-3-(α-naphthyl-thiazolidine-4-one by HPLC on a chiral stationary phase, the aldol reaction was shown to proceed via an enolate intermediate. The axially chiral enolate of the thiazolidine-4-one was found to shield one face of the heterocyclic ring rendering face selectivity with respect to the enolate. The selectivities observed at C-5 of the ring varied from none to 11.5:1 depending on the size of the ortho substituent. Although the aldol reaction proceeded with a lack of face selectivity with respect to benzaldehyde, recrystallization returned highly diastereomerically enriched products.

  10. Aroma characterization of chinese rice wine by gas chromatography-olfactometry, chemical quantitative analysis, and aroma reconstitution.

    Science.gov (United States)

    Chen, Shuang; Xu, Yan; Qian, Michael C

    2013-11-27

    The aroma profile of Chinese rice wine was investigated in this study. The volatile compounds in a traditional Chinese rice wine were extracted using Lichrolut EN and further separated by silica gel normal phase chromatography. Seventy-three aroma-active compounds were identified by gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS). In addition to acids, esters, and alcohols, benzaldehyde, vanillin, geosmin, and γ-nonalactone were identified to be potentially important to Chinse rice wine. The concentration of these aroma-active compounds in the Chinese rice wine was further quantitated by combination of four different methods, including headsapce-gas chromatography, solid phase microextraction-gas chromatography (SPME)-GC-MS, solid-phase extraction-GC-MS, and SPME-GC-pulsed flame photometric detection (PFPD). Quantitative results showed that 34 aroma compounds were at concentrations higher than their corresponding odor thresholds. On the basis of the odor activity values (OAVs), vanillin, dimethyl trisulfide, β-phenylethyl alcohol, guaiacol, geosmin, and benzaldehyde could be responsible for the unique aroma of Chinese rice wine. An aroma reconstitution model prepared by mixing 34 aroma compounds with OAVs > 1 in an odorless Chinese rice wine matrix showed a good similarity to the aroma of the original Chinese rice wine.

  11. Development of an LC-MS/MS analytical method for the simultaneous measurement of aldehydes from polyunsaturated fatty acids degradation in animal feed.

    Science.gov (United States)

    Douny, Caroline; Bayram, Pinar; Brose, François; Degand, Guy; Scippo, Marie-Louise

    2016-05-01

    Knowing that polyunsaturated fatty acids can lead to the formation of potentially toxic aldehydes as secondary oxidation products, an analytical method using liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) detection was developed to measure the concentration of eight aldehydes in animal feed: malondialdehyde (MDA), 4-hydroxy-2-nonenal (4-HNE), 4-hydroxy-2-hexenal (4-HHE), crotonaldehyde (CRT), benzaldehyde (BNZ), hexanal (HXL), 2,4-nonadienal, and 2,4-decadienal. The developed method was validated according to the criteria and procedure described in international standards. The evaluated parameters were specificity/selectivity, recovery, precision, accuracy, uncertainty, limits of detection and quantification, using the concept of accuracy profiles. These parameters were determined during experiments conducted over three different days with ground Kellogg's® Corn Flakes® cereals as model matrix for animal feed and spiked at different levels of concentration. Malondialdehyde, 4-HHE, 4-HNE, crotonaldehyde, benzaldehyde, and hexanal can be analyzed in the same run in animal feed with a very good accuracy, with recovery rates ranging from 86 to 109% for a working range going from 0.16 to 12.50 mg/kg. The analysis of 2,4-nonadienal and 2,4-decadienal can also be performed but in a limited range of concentration and with a limited degree of accuracy. Their recovery rates ranged between 54 and 114% and coefficient of variation for the intermediate precision between 11 and 25% for these two compounds. Copyright © 2016 John Wiley & Sons, Ltd.

  12. Liquid-liquid equilibrium extraction of ethanol with mixed solvent for bioethanol concentration

    Institute of Scientific and Technical Information of China (English)

    Hiroaki Habaki; Haihao Hu; Ryuichi Egashira

    2016-01-01

    The extraction of ethanol with the solvents of aldehydes mixed with m-xylene was studied for the bioethanol concentration process. Furfural and benzaldehyde were selected as extraction solvents, with which the solubility of water is smal , expecting large distribution coefficient of ethanol. The liquid–liquid two-phase region was the largest with m-xylene solvent, followed by benzaldehyde and furfural. The region of two liquid–liquid phase be-came larger with the mixed solvent of m-xylene and furfural than that with furfural solvent. The NRTL model was applied to the ethanol–water–furfural–m-xylene system, and the model could well express the liquid–liquid equilibrium of the system. For any solvent used in this study, the separation selectivity of ethanol relative to water decreased as the distribution coefficient of ethanol increased. The separation selectivity with m-xylene was the largest among the employed solvents, but the distribution coefficient was the smal est. The solvent mix-ture of furfural and m-xylene showed relatively high distribution coefficient of ethanol and separation selectivity, even in the higher mass fraction of m-xylene in the solvent phase. The ethanol extraction with a countercurrent multistage extractor by a continuous operation was simulated to evaluate the extraction performance. The ethanol content could be concentrated in the extract phase with relatively small number of extraction stages but low yield of ethanol was obtained.

  13. A novel electrosynthesis cell with a compressed graphite powder cathode and minimal organic solvent content: Application to the Reformatsky reaction

    Energy Technology Data Exchange (ETDEWEB)

    Areias, Madalena C.C.; Navarro, Marcelo; Bieber, Lothar W.; Diniz, Flamarion B. [Laboratorio de Eletrossintese Organica, DQF CCEN, Universidade Federal de Pernambuco, av. Prof. Luis Freire S/N, 50740-901 Recife (Brazil); Leonel, Eric; Cachet-Vivier, Christine; Nedelec, Jean-Yves [Equipe Electrochimie et Synthese Organique, ICMPE CNRS UMR 7182, Universite Paris 12, 2 rue H. Dunant, 94320 Thiais (France)

    2008-09-20

    A Reformatsky reaction has been employed as a model by which to highlight the advantages of a novel type of undivided electrosynthesis cell working with a content of organic solvent at least 10-times lower than that used in conventional cells. The cathode was formed from compressed graphite powder and was impregnated with a mixture of ethyl 2-bromoisobutyrate and benzaldehyde dissolved in a minimal volume of organic solvent. The cell was filled with aqueous KBr solution, and the electrolysis carried out at a constant potential corresponding to the reduction of the bromoester. Several parameters were optimized with respect to the yield of coupling product, including the ratio of bromoester to benzaldehyde, the pressure of compaction of the electrode powder inside the cavity, and the influence of the cathodic material. Ethyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate was obtained in a yield of up to 86%, and ethyl isobutyrate was the only by-product. A number of other model substrates have been investigated in order to determine the scope and limitations of this new methodology. (author)

  14. Engineering Escherichia coli for renewable benzyl alcohol production

    Directory of Open Access Journals (Sweden)

    Shawn Pugh

    2015-12-01

    Full Text Available Benzyl alcohol is an aromatic hydrocarbon used as a solvent and an intermediate chemical in the pharmaceutical, cosmetics, and flavor/fragrance industries. The de novo biosynthesis of benzyl alcohol directly from renewable glucose was herein explored using a non-natural pathway engineered in Escherichia coli. Benzaldehyde was first produced from endogenous phenylpyruvate via three heterologous steps, including hydroxymandelate synthase (encoded by hmaS from Amycolatopsis orientalis, followed by (S-mandelate dehydrogenase (encoded by mdlB and phenylglyoxylate decarboxylase (encoded by mdlC from Pseudomonas putida ATCC 12633. The subsequent rapid and efficient reduction of benzaldehyde to benzyl alcohol occurred by the combined activity and native regulation of multiple endogenous alcohol dehydrogenases and/or aldo-keto reductases. Through systematic deletion of competing aromatic amino acid biosynthesis pathways to promote endogenous phenylpyruvate availability, final benzyl alcohol titers as high as 114±1 mg/L were realized, representing a yield of 7.6±0.1 mg/g on glucose and a ~5-fold improvement over initial strains.

  15. Surface Modification of Fly Ash for Active Catalysis

    Directory of Open Access Journals (Sweden)

    Deepti Jain

    2013-01-01

    Full Text Available Fly ash based effective solid base catalyst (KF/Al2O3/fly ash473, KF/Al2O3/fly ash673, and KF/Al2O3/fly ash873 was synthesized by loading KF over chemically and thermally activated fly ash. The chemical activation was done by treating fly ash with aluminum nitrate via precipitation method followed by thermal activation at 650°C to increase the alumina content in fly ash. The increased alumina content was confirmed by SEM-EDX analysis. The alumina enriched fly ash was then loaded with KF (10 wt% and calcined at three different temperatures 473 K, 673 K and 873 K. The amount of loaded KF was monitored by XRD, FTIR spectroscopy, SEM-EDX, TEM and Flame Atomic Absorption Spectrophotometer. The catalytic activities of the catalysts were tested in the Claisen-Schmidt condensation of benzaldehyde and 4-methoxybenzaldehyde with 2′-hydroxyacetophenone to produce 2′-hydroxychalcone and 4-methoxy-2′-hydroxychalcone respectively. Higher conversion (83% of benzaldehyde and (89% of 4-methoxybenzaldehyde reveals that among these heterogeneous catalysts KF/Al2O3/fly ash673 is very active.

  16. Proteins involved in wine aroma compounds metabolism by a Saccharomyces cerevisiae flor-velum yeast strain grown in two conditions.

    Science.gov (United States)

    Moreno-García, Jaime; García-Martínez, Teresa; Millán, M Carmen; Mauricio, Juan Carlos; Moreno, Juan

    2015-10-01

    A proteomic and exometabolomic study was conducted on Saccharomyces cerevisiae flor yeast strain growing under biofilm formation condition (BFC) with ethanol and glycerol as carbon sources and results were compared with those obtained under no biofilm formation condition (NBFC) containing glucose as carbon source. By using modern techniques, OFFGEL fractionator and LTQ-Orbitrap for proteome and SBSE-TD-GC-MS for metabolite analysis, we quantified 84 proteins including 33 directly involved in the metabolism of glycerol, ethanol and 17 aroma compounds. Contents in acetaldehyde, acetic acid, decanoic acid, 1,1-diethoxyethane, benzaldehyde and 2-phenethyl acetate, changed above their odor thresholds under BFC, and those of decanoic acid, ethyl octanoate, ethyl decanoate and isoamyl acetate under NBFC. Of the twenty proteins involved in the metabolism of ethanol, acetaldehyde, acetoin, 2,3-butanediol, 1,1-diethoxyethane, benzaldehyde, organic acids and ethyl esters, only Adh2p, Ald4p, Cys4p, Fas3p, Met2p and Plb1p were detected under BFC and as many Acs2p, Ald3p, Cem1p, Ilv2p, Ilv6p and Pox1p, only under NBFC. Of the eight proteins involved in glycerol metabolism, Gut2p was detected only under BFC while Pgs1p and Rhr2p were under NBFC. Finally, of the five proteins involved in the metabolism of higher alcohols, Thi3p was present under BFC, and Aro8p and Bat2p were under NBFC.

  17. EAG and behavioral responses of Helicoverpa armigera males to volatiles from poplar leaves and their combinations with sex pheromone

    Institute of Scientific and Technical Information of China (English)

    邓建宇; 黄永平; 魏洪义; 杜家纬

    2004-01-01

    Electroantennogram (EAG) evaluation of selected compounds from wilted leaves ofblack poplar,Populus nigra,showed that phenyl acetaldehyde, methyl salicylate, (E)-2-hexenal elicited strong responses from male antennae of Helicoverpa armigera. When mixed with sex pheromone (Ph), some volatiles, e.g. phenyl acetaldehyde, benzyl alcohol,phenylethanol, methylsalicylate, linalool, benzaldehyde, (Z)-3-hexenol, (Z)-3-hexenylacetate, (Z)-6-nonenol, cineole, (E)-2-hexenal, and geraniol elicited stronger responses from male antennae than Ph alone. Wind tunnel bioassay demonstrated that various volatiles could either enhance or inhibit the effect of synthetic sex pheromone. (E)-2-hexenal, (Z)-3-hexenol and linalool in combination with Ph could not induce any male to land on source at all, whereas phenyl acetaldehyde, benzaldehyde, (Z)-6-nonenol and salicylaldehyde combined with Ph enhanced male response rates by 58.63%,50.33%, 51.85% and 127.78%, respectively, compared to Ph alone. These results suggested that some volatiles should modify sex pheromone caused behavior and that some of them could possibly be used as a tool for disrupting mating or for enhancing the effect of synthetic sex pheromone in the field.

  18. EAG and behavioral responses of Helicoverpa armigera males to volatiles from poplar leaves and their combinations with sex pheromone

    Institute of Scientific and Technical Information of China (English)

    邓建宇; 黄永平; 魏洪义

    2004-01-01

    Electroantennogram (EAG) evaluation of selected compounds from wilted leaves of black poplar, Populus nigra, showed that phenyl acetaldehyde, methyl salicylate, (E)-2-hexenal elicited strong responses from male antennae of Helicoverpa armigera. When mixed with sex pheromone (Ph), some volatiles, e.g. phenyl acetaldehyde, benzyl alcohol, phenylethanol, methylsalicylate, linalool, benzaldehyde, (Z)-3-hexenol, (Z)-3-hexenylacetate, (Z)-6-nonenol, cineole, (E)-2-hexenal, and geraniol elicited stronger responses from male antennae than Ph alone. Wind tunnel bioassay demonstrated that various volatiles could either enhance or inhibit the effect of synthetic sex pheromone. (E)-2-hexenal, (Z)-3-hexenol and linalool in combination with Ph could not induce any male to land on source at all, whereas phenyl acetaldehyde, benzaldehyde, (Z)-6-nonenol and salicylaldehyde combined with Ph enhanced male response rates by 58.63%, 50.33%, 51.85% and 127.78%, respectively, compared to Ph alone. These results suggested that some volatiles shouldmodify sex pheromone caused behavior and that some of them could possibly be used as a tool for disrupting mating or for enhancing the effect of synthetic sex pheromone in the field.

  19. Investigation of the formation of benzoyl peroxide, benzoic anhydride, and other potential aerosol products from gas-phase reactions of benzoylperoxy radicals

    Science.gov (United States)

    Strollo, Christen M.; Ziemann, Paul J.

    2016-04-01

    The secondary organic aerosol (SOA) products of the reaction of benzaldehyde with Cl atoms and with OH radicals in air in the absence of NOx were investigated in an environmental chamber in order to better understand the possible role of organic peroxy radical self-reactions in SOA formation. SOA products and authentic standards were analyzed using mass spectrometry and liquid chromatography, and results show that the yields of benzoyl peroxide (C6H5C(O)OO(O)CC6H5) and benzoic anhydride (C6H5C(O)O(O)CC6H5), two potential products from the gas-phase self-reaction of benzoylperoxy radicals (C6H5C(O)OO·), were less than 0.1%. This is in contrast to results of recent studies that have shown that the gas-phase self-reactions of β-nitrooxyperoxy radicals formed from reactions of isoprene with NO3 radicals form dialkyl peroxides that contribute significantly to gas-phase and SOA products. Such reactions have also been proposed to explain the gas-phase formation of extremely low volatility dimers from autooxidation of terpenes. The results obtained here indicate that, at least for benzoylperoxy radicals, the self-reactions form only benzoyloxy radicals. Analyses of SOA composition and volatility were inconclusive, but it appears that the SOA may consist primarily of oligomers formed through heterogeneous/multiphase reactions possibly involving some combination of phenol, benzaldehyde, benzoic acid, and peroxybenzoic acid.

  20. Matrix isolation infrared spectroscopic study of 4-Pyridinecarboxaldehyde and of its UV-induced photochemistry

    Science.gov (United States)

    Cluyts, Liesel; Sharma, Archna; Kuş, Nihal; Schoone, Kristien; Fausto, Rui

    2017-01-01

    The structure, infrared spectrum, barrier to internal rotation, and photochemistry of 4-pyridinecarboxaldehyde (4PCA) were studied by low-temperature (10 K) matrix isolation infrared spectroscopy and quantum chemical calculations undertaken at both Moller-Plesset to second order (MP2) and density functional theory (DFT/B3LYP) levels of approximation. The molecule has a planar structure (Cs point group), with MP2/6-311 ++G(d,p) predicted internal rotation barrier of 26.6 kJ mol- 1, which is slightly smaller than that of benzaldehyde ( 30 kJ mol- 1), thus indicating a less important electron charge delocalization from the aromatic ring to the aldehyde moiety in 4PCA than in benzaldehyde. A complete assignment of the infrared spectrum of 4PCA isolated in an argon matrix has been done for the whole 4000-400 cm- 1 spectral range, improving over previously reported data. Both the geometric parameters and vibrational frequencies of the aldehyde group reveal the relevance in this molecule of the electronic charge back-donation effect from the oxygen trans lone electron pair to the aldehyde Csbnd H anti-bonding orbital. Upon in situ UV irradiation of the matrix-isolated compound, prompt decarbonylation was observed, leading to formation of pyridine.

  1. Formation of metabolites during biodegradation of linear alkylbenzene sulfonate in an upflow anaerobic sludge bed reactor under thermophilic conditions.

    Science.gov (United States)

    Mogensen, A S; Ahring, B K

    2002-03-05

    Biodegradation of linear alkylbenzene sulfonate (LAS) was shown in an upflow anaerobic sludge blanket reactor under thermophilic conditions. The reactor was inoculated with granular biomass and fed with a synthetic medium and 3 micromol/L of a mixture of LAS with alkylchain length of 10 to 13 carbon atoms. The reactor was operated with a hydraulic retention time of 12 h with effluent recirculation in an effluent to influent ratio of 5 to 1. A sterile reactor operated in parallel revealed that sorption to sludge particles initially accounted for a major LAS removal. After 8 days of reactor operation, the removal of LAS in the reactor inoculated with active granular biomass exceeded the removal in the sterile reactor inoculated with sterile granular biomass. The effect of sorption ceased after 185 to 555 h depending on the LAS homologs. 40% of the LAS was biodegraded, and the removal rate was 0.5 x 10(-6) mol/h/mL granular biomass. Acidified effluent from the reactor was subjected to dichloromethane extraction followed by gas chromatography/mass spectrometry. Benzenesulfonic acid and benzaldehyde were detected in the reactor effluent from the reactor with active granular biomass but not in the sterile and unamended reactor effluent. Benzenesulfonic acid and benzaldehyde are the first identified degradation products in the anaerobic degradation of LAS.

  2. Synthesis and characterization of Cu(II), Co(II) and Ni(II) complexes of a number of sulfadrug azodyes and their application for wastewater treatment

    Science.gov (United States)

    El-Baradie, K.; El-Sharkawy, R.; El-Ghamry, H.; Sakai, K.

    2014-03-01

    The azodye ligand (HL1) was synthesized from the coupling of sulfaguanidine diazonium salt with 2,4-dihydroxy-benzaldehyde while the two ligands, HL2 and HL3, were prepared by the coupling of sulfadiazine diazonium salt with salicylaldehyde (HL2) and 2,4-dihydroxy-benzaldehyde (HL3). The prepared ligands were characterized by elemental analysis, IR, 1H NMR and mass spectra. Cu(II), Co(II) and Ni(II) complexes of the prepared ligands have been synthesized and characterized by various spectroscopic techniques like IR, UV-Visible as well as magnetic and thermal (TG and DTA) measurements. It was found that all the ligands behave as a monobasic bidentate which coordinated to the metal center through the azo nitrogen and α-hydroxy oxygen atoms in the case of HL1 and HL3. HL2 coordinated to the metal center through sulfonamide oxygen and pyrimidine nitrogen. The applications of the prepared complexes in the oxidative degradation of indigo carmine dye exhibited good catalytic activity in the presence of H2O2 as an oxidant. The reactions followed first-order kinetics and the rate constants were determined. The degradation reaction involved the catalytic action of the azo-dye complexes toward H2O2 decomposition, which can lead to the generation of HOrad radicals as a highly efficient oxidant attacking the target dye. The detailed kinetic studies and the mechanism of these catalytic reactions are under consideration in our group.

  3. Study on Modification of Coal Tar Pitch and Structure of Mesophase%煤沥青的改性及中间相结构研究

    Institute of Scientific and Technical Information of China (English)

    解小玲; 赵彩霞; 曹青; 靳利娥; 张怀平

    2012-01-01

    以对甲苯磺酸(PTS)为催化剂,研究了改性温度、时间和改性剂苯甲醛用量对改性煤沥青(MCTP)中间相显微结构产生的影响.研究表明,当苯甲醛/煤沥青(CTP)质量比为30/100、反应温度为150℃和反应时间为15h时得到的MCTP,其中间相呈不完全纤维组织结构;XRD分析表明,通过苯甲醛改性煤沥青,有利于提高中间相光学组织结构的有序性.FT-IR分析表明,改性后芳核骨架振动吸收频率增大,提高了芳核的缩合度;1H-NMR分析表明,改性过程中的改性反应主要发生在HA上,并对改性过程可能发生的反应机理进行了分析.%Coal tar pitch (CTP) has been successfully modified with modifier benzaldehyde in the presence of p-toluene sulfonic acid as catalyst. The main influence factors such as the mass ratio of benzaldehyde to CTP, the temperature and reaction time on optical microstructure of mesophase formed by modified coal tar pitch (MCTP) were observed. The results showed that the optical microstructure of mesophase formed by carbonized MCTP, which was produced when the mass ratio of benzaldehyde to CTP was 0. 3, the modified reaction kept for 15 h at 150 ℃, has the characteristic with incomplete fibrous structure. The result of XRD revealed that order of optical microstructure of mesophase was enhanced through modifying coal tar pitch. The results from FT-IR analysis indicated that the degree of condensation of aromatic ring increased according to the increment of vibration frequency of aromatic ring. The spectra from 1 H-NMR indicated that the polymerization reaction mainly occurred in the Ha position of aromatic rings. The possible reaction mechanism was proposed.

  4. Preparation of manganese oxide immobilized on SBA-15 by atomic layer deposition as an efficient and reusable catalyst for selective oxidation of benzyl alcohol in the liquid phase

    Energy Technology Data Exchange (ETDEWEB)

    Mahdavi, Vahid, E-mail: v-mahdavi@araku.ac.ir; Mardani, Mahdieh

    2015-04-01

    Manganese oxide supported on mesoporous silica SBA-15 catalyst (Mn-SBA-15) was tested with Mn contents in the range of 0.8–23 wt%. Samples were prepared by the controlled grafting process of atomic layer deposition (ALD). Other sample was prepared for comparisons by the wet impregnation method. These samples were characterized by the techniques of ICP, XRD, SEM, Raman, FT-IR spectroscopy, diffuse reflectance UV–Vis, TGA-DSC, and N{sub 2} absorption–desorption surface area measurement. Results indicated that anchored manganese oxide particles have been successfully synthesized over the surface of SBA-15. These samples contained Red-Ox ion pairs of Mn{sup 2+} and Mn{sup 3+} highly dispersed on the mesoporous silica surface. The impregnated sample exhibited lower surface area and contained Red-Ox ion pairs of Mn{sup 3+} and Mn{sup 4+} more aggregated particles on the SBA-15 surface. Results determined Mn-SBA-15 as an efficient and selective catalyst for oxidation of benzyl alcohol with tert-butylhydroperoxide in liquid phase. In accordance with expectations, there was a negligible amount of leaching of immobilized manganese oxide from the support during the reaction, because of strong surface interaction between manganese oxide and hydroxyls groups. The influences of reaction temperature, reaction time, solvent, TBHP/benzyl alcohol molar ratio, amount of catalyst and reusability were investigated. Under optimized conditions (0.2 g catalyst, TBHP/benzyl alcohol molar ratio 1, solvent acetonitrile; T = 90 °C; reaction time 8 h), results achieved 70% conversion of benzyl alcohol and 100% selectivity to benzaldehyde. - Highlights: • Manganese oxide immobilized on SBA-15 were prepared by atomic layer deposition (ALD). • Oxidation of benzyl alcohol to benzaldehyde over this catalyst were investigated. • Effects of loading of manganese oxide, T, oxidant/alcohol ratio were investigated. • The leaching of manganese oxide from support during the reaction was

  5. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SCHIFF BASE DERIVATIVES OF 4-CHLORO-3-NITROBENZOIC ACID

    Directory of Open Access Journals (Sweden)

    Kumari Santosh

    2012-12-01

    Full Text Available 4-chloro-3-nitrobenzoic acid was selected as nucleus structure having good antibacterial property. It was thought worthwhile to synthesize Schiff base derivatives of 4-chloro-3-nitrobenzoic acid in search of better antibacterial agents. The compounds were synthesized by first reducing nitro group in presence of Sn/HCl to 3-amino-4-chlorobenzoic acid, which on treatment with substituted benzaldehyde afforded the synthesis of the envisaged compounds. The synthesized compounds were purified and chemically characterized. They were screened for their antibacterial activity and result suggested that SKY-1, SKY-5 and SKY-8 were highly active against both Gram (+ and Gram(- bacteria like B.subtilis, S.aureus and E.coli whereas all are were found moderately to inactive against P.aeruginosa.

  6. Volatile components of vine leaves from two Portuguese grape varieties (Vitis vinifera L.), Touriga Nacional and Tinta Roriz, analysed by solid-phase microextraction.

    Science.gov (United States)

    Fernandes, Bruno; Correia, Ana C; Cosme, Fernanda; Nunes, Fernando M; Jordão, António M

    2015-01-01

    The purpose of this work was to study the volatile composition of vine leaves and vine leaf infusion prepared from vine leaves collected at 30 and 60 days after grape harvest of two Vitis vinifera L. species. Eighteen volatile compounds were identified by gas chromatography-mass spectrometry in vine leaves and in vine leaf infusions. It was observed that the volatile compounds present in vine leaves are dependent on the time of harvest, with benzaldehyde being the major volatile present in vine leaves collected at 30 days after harvesting. There are significant differences in the volatile composition of the leaves from the two grape cultivars, especially in the sample collected at 60 days after grape harvest. This is not reflected in the volatile composition of the vine leaf infusion made from this two cultivars, the more important being the harvesting date for the volatile profile of vine leaf infusion than the vine leaves grape cultivar.

  7. Preparation and preliminary biological evaluation of [[sup 18]F]NCQ-115: a new selective reversible dopamine D2 receptor ligand

    Energy Technology Data Exchange (ETDEWEB)

    Najafi, A.; Peterson, A.; Buchsbaum, M. (California Univ., Irvine, CA (United States). Dept. of Psychiatry); O' Dell, S.; Weihmuller, F. (California Univ., Irvine , CA (United States). Dept. of Psychobiology)

    1993-05-01

    [sup 18]F-labeled dopamine D2 antagonist, NCQ-115 ((+)-(R)-5-bromo-N-((fluorobenzyl)-2-pyrrolidinyl)-methyl-2,3-dime thoxybenzamide), was successfully prepared using a remotely controlled system. [[sup 18]F]Fluoride was reacted with the trifluoromethanesulfonate salt of 4-(trimethylamino)benzaldehyde. The product was first reduced with LAH, and then reacted with thionyl bromide to yield [sup 18]F-labeled 4-fluorobenzylbromide. [[sup 18]F]4-fluorobenzylbromide was then reacted with the pyrrolidine precursor (NCQ-282) to yield the product [[sup 18]F]NCQ-115 contaminated with unreacted starting material. The product was purified by reverse phase chromatography yielding [[sup 18]F]NCQ-115 with a specific activity of more than 1400 Ci/mmol. Autoradiographic and biodistribution data following injection of [[sup 18]F]NCQ-115 in rats revealed the regional uptake of striatum/cerebellum to be 3.2 at 30 min post-injection. (author).

  8. Localized operator partitioning method for electronic excitation energies in the time-dependent density functional formalism

    CERN Document Server

    Nagesh, Jayashree; Brumer, Paul; Izmaylov, Artur F

    2016-01-01

    We extend the localized operator partitioning method (LOPM) [J. Nagesh, A.F. Izmaylov, and P. Brumer, J. Chem. Phys. 142, 084114 (2015)] to the time-dependent density functional theory (TD-DFT) framework to partition molecular electronic energies of excited states in a rigorous manner. A molecular fragment is defined as a collection of atoms using Stratman-Scuseria-Frisch atomic partitioning. A numerically efficient scheme for evaluating the fragment excitation energy is derived employing a resolution of the identity to preserve standard one- and two-electron integrals in the final expressions. The utility of this partitioning approach is demonstrated by examining several excited states of two bichromophoric compounds: 9-((1-naphthyl)-methyl)-anthracene and 4-((2-naphthyl)-methyl)-benzaldehyde. The LOPM is found to provide nontrivial insights into the nature of electronic energy localization that are not accessible using simple density difference analysis.

  9. Estudo experimental e teórico da redução de bases de Schiff derivadas da 3,3-difenilpropilamina

    Directory of Open Access Journals (Sweden)

    Esteves-Souza Andressa

    2004-01-01

    Full Text Available A series of seven Schiff bases have been synthesized from 3,3-diphenylpropilamine and substituted benzaldehydes. These imines were treated with NaBH4 in ethanol affording the corresponding amines in 98-55% yields. A molecular modeling study was performed with the Schiff bases in order to compare the theoretical parameters with the experimental results. The theoretical parameters were obtained by AM1 and PM3 semi-empirical methods. The analysis of charge, electron densities and LUMO coefficients suggested that the most favorable interactions should occur with Schiff bases containing electron-donating groups, in accordance with experimental yields, showing that the higher reactivity is due to higher electrophilic character of imine carbons.

  10. Development of quantitative extraction method of amygdalin without enzymatic hydrolysis from tonin(Persicae Semen) by high performance liquid chromatography.

    Science.gov (United States)

    Hwang, Eun-Young; Lee, Sang-Soo; Lee, Je-Hyun; Hong, Seon-Pyo

    2002-08-01

    Tonin(Persicae Semen) is the herb medicine that contains amygdalin as a major ingredient. Amygdalin in water is decomposed into benzaldehyde, HCN, and glucose by emulsin, a hydrolysis enzyme in tonin. A useful and practical method for the optimum extraction condition of amygdalin without enzymatic hydrolysis is required. The extraction yield of amygdalin of natural formula tonin was 0.1% from crude powders, 1.4% from small pieces, 3.5% from half pieces and 2.4% from whole pieces. The extraction yield of amygdalin of outer shell-eliminated tonin was 0.3% from crude powders, 1.4% from small pieces, and 3.5% from half pieces and whole pieces respectively. The extraction yield of amygdalin was most high when using the size larger than half.

  11. Crystal structure of 1,3-bis­[(E)-4-meth­oxy­benzyl­idene­amino]­propan-2-ol

    Science.gov (United States)

    Rivera, Augusto; Miranda-Carvajal, Ingrid; Ríos-Motta, Jaime; Bolte, Michael

    2016-01-01

    The title Schiff base, C19H22N2O3, was synthesized via the condensation reaction of 1,3-di­amino­propan-2-ol with 4-meth­oxy­benzaldehyde using water as solvent. The mol­ecule exists in an E,E conformation with respect to the C=N imine bonds and the dihedral angle between the aromatic rings is 37.25 (15)°. In the crystal, O—H⋯N hydrogen bonds link the mol­ecules into infinite C(5) chains propagating along the a-axis direction. The packing of these chains is consolidated by C—H⋯O inter­actions and C—H⋯π short contacts, forming a three-dimensional network. PMID:27980818

  12. Synthesis and Antiviral Bioactivities of 2-Aryl- or 2-Methyl-3-(substituted- Benzalamino-4(3H-quinazolinone Derivatives

    Directory of Open Access Journals (Sweden)

    Zhuo Chen

    2007-12-01

    Full Text Available A simple and general method has been developed for the synthesis of various4(3H-quinazolinone derivatives by the treatment of the appropriate 3-amino-2-aryl-4(3H-quinazolinone with a substituted benzaldehyde in ethanol. The structures of the compoundswere characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. The title 2-aryl- or 2-methyl-3-(substituted-benzalamino-4(3H-quinazolinone compounds III-1~III-31 were found to possess moderate to good antiviral activity. Semi-quantitative PCR andReal Time PCR assays were used to ascertain the target of action of compound III-31against TMV. The studies suggest that III-31 possesses antiviral activity due to inductionof up-regulation of PR-1a and PR-5, thereby inhibiting virus proliferation and movementby enhancement of the activity of some defensive enzyme.

  13. Crystal structure of 4-{[(2,4-di­hydroxy­benzyl­idene)amino]­meth­yl}cyclo­hexane­carb­oxy­lic acid

    Science.gov (United States)

    Danish, Muhammad; Akbar, Saba; Tahir, Muhammad Nawaz; Butt, Rabia Ayub; Ashfaq, Muhammad

    2015-01-01

    In the title compound, C15H19NO4, the cyclo­hexyl ring adopts a chair conformation with both exocyclic C—C bonds in equatorial orientations. The dihedral angle between the basal plane of cyclo­hexyl ring and the 2,4-di­hydroxy­benzaldehyde moiety is 84.13 (13)°. An intra­molecular O—H⋯N hydrogen bonds closes an S(6) ring. In the crystal, Oc—H⋯Op (c = carb­oxy­lic acid, p = phenol) hydrogen bonds link the mol­ecules into [100] C(13) chains whereas an Op—H⋯Oc hydrogen bond generates [101] C(15) chains. Together, these bonds generate (010) sheets incorporating R 2 2(20) loops. Weak C—H⋯O and C—H⋯π inter­actions also occur. PMID:26870569

  14. Synthesis and catalytic activity of Ln(III) complexes with an unsymmetrical Schiff base including multi()C = N-groups

    Institute of Scientific and Technical Information of China (English)

    姚克敏; 李宁; 沈联芳

    2003-01-01

    A synthetic method for a new unsymmetrical Schiff base and its Ln (III) complexes including multi C == N- groups is reported. The complexes are characterized by elemental analysis, IR spectra, 1H and 13C NMR, especially 2D-COSY1H, 1H NMR spectra. The general formula of the obtained complexes is [Ln3(TBLY)(NO3)3]@nH2O (Ln = La, n = 3; Ln = Nd, n = 5; Ln = Gd, Dy, Yb, Y, n = 7), whereTBLY = tetraglycol aldehyde-2,4-dihydroxy benzaldehyde bis-lysine Schiff base. In addition, the evidence for existence of C == CH-NH- group is supported bythe AM1 method. The complexes obtained may be used as a catalyst. Conversion rate of 80% with the viscosity-average molecular weight 220000 for the polymerization of methyl methacrylate (MMA) without addition of any cocatalyst has been obtained.

  15. Studies on the photochemistry of 1,7-diphenyl-1,6-heptadiene-3,5-dione, a non-phenolic curcuminoid model.

    Science.gov (United States)

    Sundaryono, Agus; Nourmamode, Aziz; Gardrat, Christian; Grelier, Stéphane; Bravic, Georges; Chasseau, Daniel; Castellan, Alain

    2003-09-01

    The comparative photostability of curcumin 1, and two non-phenolic curcuminoids: 1,7-diphenyl-1,6-heptadiene-3,5-dione 2 (unsubstituted curcumin) and dimethylcurcumin 3 in non-degassed dilute solutions (approximately 3-5 x 10(-5) mol l(-1)) has been established by UV-visible absorption spectroscopy; disappearance quantum yields were measured. The similar behavior of the three studied curcuminoids is indicative of only a moderate role of phenol groups in the photodegradation process. Structural analysis of the photodegradation products of compound 2 in more concentrated solution (approximately 3.6 x 10(-3) mol l(-1)) shows formation of benzaldehyde, cinnamaldehyde, 2'-hydroxy-5',6'-benzochalcone 4, flavanone 5 and some other unidentified photoproducts. Flavanone 5 is formed by irradiation of chalcone 4. It represents a unique example of photochemical conversion of a diarylheptanoid molecule into a flavonoid, another very important class of natural products.

  16. Asymmetric carbon-carbon bond forming reactions catalyzed by chiral titanium complexes. Efficient synthesis of optically active secondary alcohols; Kiraru na chitan shokubai ni yoru fuseitanso-tanso ketsugo keisei. Kogaku kassei dainikyu arukoru no gosei

    Energy Technology Data Exchange (ETDEWEB)

    Hayashi, M. [Yamaguchi Univ., Yamaguchi (Japan). Faculty of Science

    1996-02-01

    For asymmetric metal complex catalysts with high catalytic activity and ability for recognizing asymmetry, it is most important to choose center metals and design asymmetric organic ligands. When the authors began to study on the title reactions, combination of titanium alkoxides as center metals and chiral Schiff bases as organic ligands was unknown, although two moieties had been used independently for asymmetric reactions with excellent results. Asymmetric silylcyanation of aldehydes and enantio-selective addition of diketone to aldehydes are introduced, that have been achieved by authors using titanium complexes of the above combination. In the silylcyanation, reactivity is remarkably improved, compared with a single catalyst of titanium isopropoxide. Cyanohydrin of R from was obtained preferentially with salicyladehyde, particularly having 3-tert butyl group, in an asymmetric yield of 85 % ee. In the latter addition reaction, 5-hydroxy-3-ketoesters were obtained from benzaldehyde in an asymmetric yield as high as 91 % ee. 9 refs., 2 figs.

  17. Synthesis and antibacterial and antifungal studies of novel nitrogen containing heterocycles from 5-Ethylpyridin-2-ethanol

    Directory of Open Access Journals (Sweden)

    Patel N

    2010-01-01

    Full Text Available A novel series of chalcones, pyrimidines and imidazolinone is described; chalcones (4a-o were prepared from the lead molecule 4-[2-(5-ethylpyridin-2-ylethoxy]benzaldehyde. Pyrimidine (5a-o derivatives were prepared from the reaction of chalcones and guanidine nitrate in alkali media. Imidazolinones (6a-o were synthesized from reaction of pyrimidine and oxazolone derivatives (prepared by Erlenmeyer azlactone synthesis. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1 H and 13 C NMR spectral data. All the products were screened against different strains of bacteria and fungi. Most of these compounds showed better inhibitory activity in comparison to the standard drugs.

  18. Effect of condensation product on electrodeposition of zinc on mild steel

    Indian Academy of Sciences (India)

    S Shivakumara; U Manohar; Y Arthoba Naik; T V Venkatesha

    2007-10-01

    Electrodeposition of zinc on steel was obtained from acid chloride bath containing condensation products (CP) of 3,4,5-trimethoxy benzaldehyde (TMB) and chitosan (CTN). The effect of bath constituents, pH, current density and temperature on the nature of deposit was studied by Hull cell experiments. The bath composition and operating parameters were optimized. The adhesion, ductility and corrosion resistance of the deposits were discussed. Throwing power and current efficiency values under different plating conditions were measured. SEM photomicrographs of the deposit were taken to study the surface morphology. The inclusion of addition agent in the deposit was investigated from IR spectrum of the scrapped deposit. The consumption of brightener in the lab scale is 10 mLL-1 for 1000 amp-h.

  19. Synthesis of Some Pyrazolone Derivatives and Evaluation of its Antibacterial and Cytotoxic Activity

    Directory of Open Access Journals (Sweden)

    Rishiram Prajuli

    2015-12-01

    Full Text Available A series of novel pyrazolone derivative were synthesized by two different schemes (scheme-1 by the reaction of phenyl hydrazine and ethyl acetoacetate with substituted benzaldehydes PYR-1 to PYR-4 and (by the reaction of synthesized chalcone with phenyl hydrazine PYR-5 and characterised with its physical parameters (M.P, colour, %yield, solubility etc.. The entire synthesized compound was tested for their antimicrobial activity against Gram-positive and Gram-negative strains of bacteria and brimeshrimp bioassay was conducted for evaluation of cytotoxic activity The Investigation of antimicrobial screening data revealed that most of the tested compounds showed moderate to good antimicrobial activity. And cytotoxicity activity of compounds was also found to be satisfactory.

  20. Compostos voláteis em méis florais Volatile compounds in floral honeys

    Directory of Open Access Journals (Sweden)

    Carlos Alberto Bastos De Maria

    2003-01-01

    Full Text Available A review about origin, composition and importance of volatile compounds in floral honeys is presented. Hydrocarbons, aromatic components, acids, diacids, terpenoids, ketones, aldehydes, esters and alcohols have been found in honey aroma of different botanical origin. Cis-rose oxide has been proposed as an indicator for Tilia cordata honey. Citrus honeys are known to contain methyl anthranilate, a compound which other honeys virtually lack. Linalool, phenylethylalcohol, phenylacetaldehyde, p-anisaldehyde and benzaldehyde are important contributors for the aroma of different unifloral honeys. Both isovaleric acid, gama-decalactone and benzoic acid appears to be important odourants for Anarcadium occidentale and Croton sp. honeys from Brazil. The furfurylmercaptan, benzyl alcohol, delta-octalactone, eugenol, phenylethylalcohol and guaiacol appear to be only relevant compounds for Anarcadium occidentale. The vanillin was considered an important odourant only for Croton sp..

  1. Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells.

    Science.gov (United States)

    Abdul Rahim, Aisyah Saad; Salhimi, Salizawati Muhamad; Arumugam, Natarajan; Pin, Lim Chung; Yee, Ng Shy; Muttiah, Nithya Niranjini; Keat, Wong Boon; Abd Hamid, Shafida; Osman, Hasnah; Mat, Ishak b

    2013-12-01

    A new series of N-sec/tert-butyl 2-arylbenzimidazole derivatives was synthesised in 85-96% yields within 2-3.5 min by condensing ethyl 3-amino-4-butylamino benzoate with various substituted metabisulfite adducts of benzaldehyde under focused microwave irradiation. The benzimidazole analogues were characterised using (1)H NMR, (13)C NMR, high resolution MS and melting points. Evaluation of antiproliferative activity of the benzimidazole analogues against MCF-7 and MDA-MB-231 revealed several compounds with unexpected selective inhibitions of MDA-MB-231 in micromolar range. All analogues were found inactive towards MCF-7. The most potent inhibition against MDA-MB-231 human breast cancer cell line came from the unsubstituted 2-phenylbenzimidazole 10a.

  2. (E)-4-[4-(Diethyl-amino)-benzyl-idene-ammonio]-benzene-sulfonate.

    Science.gov (United States)

    Ruanwas, Pumsak; Chantrapromma, Suchada; Fun, Hoong-Kun

    2012-07-01

    The title compound, C(17)H(20)N(2)O(3)S, synthesised from sulfanilic acid and 4-diethyl-amino-benzaldehyde, crystallized out as a zwitterion with the central N atom protonated. The zwitterion exists in an E conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 37.57 (5)°. In the crystal, the zwitterions are linked into a tape along the a axis by N-H⋯O hydrogen bonds. The crystal structure is further stabilized by weak C-H⋯O inter-actions and π-π inter-actions with a centroid-centroid distance of 3.8541 (6) Å. An O⋯O [2.8498 (11) Å] short contact is present.

  3. Comparison of the Essential Oil Composition of Selected Impatiens Species and Its Antioxidant Activities.

    Science.gov (United States)

    Szewczyk, Katarzyna; Kalemba, Danuta; Komsta, Łukasz; Nowak, Renata

    2016-09-01

    The present paper describes the chemical composition of the essential oils obtained by hydrodistillation from four Impatiens species, Impatiens glandulifera Royle, I. parviflora DC., I. balsamina L. and I. noli-tangere L. The GC and GC-MS methods resulted in identification of 226 volatile compounds comprising from 61.7%-88.2% of the total amount. The essential oils differed significantly in their composition. Fifteen compounds were shared among the essential oils of all investigated Impatiens species. The majority of these constituents was linalool (0.7%-15.1%), hexanal (0.2%-5.3%) and benzaldehyde (0.1%-10.2%). Moreover, the antioxidant activity of the essential oils was investigated using different methods. The chemical composition of the essential oils and its antioxidant evaluation are reported for the first time from the investigated taxon.

  4. Synthesis, structural characterization, antimicrobial activities and theoretical investigations of some 4-(4-aminophenylsulfonyl) phenylimino) methyl)-4-(aryldiazenyl) phenol

    Science.gov (United States)

    Ghasemian, Motaleb; Kakanejadifard, Ali; Karami, Tahereh

    2016-11-01

    The azo-azomethine dyes with a different substitution have been designed from the reaction of 4,4‧-diaminodiphenyl sulfone with 2-hydroxy-5-(aryldiazenyl)benzaldehyde. The compounds have been characterized by elemental analysis, Mass, IR, UV-Vis, TGA-DTA and NMR spectroscopy. The solvatochromism behaviors, effects of substitution and pH on the electronic absorption spectra of dyes were evaluated. The in vitro antimicrobial activities were also screened for their potential for antibiotic activities by broth micro dilution method. Also, the optimum molecular geometries, molecular electrostatic potential (MEP), nucleus-independent chemical shift (NICS) and frontier molecular orbitals (FMO), vibrational spectra (IR) and electronic absorption (UV-Vis) spectra of the title compounds have been investigated with the help of DFT and TDDFT methods with 6-311 ++G(d,p) basis sets and PCM calculations. The results of the calculations show excellent agreement with the experimental value.

  5. Stereochemistry and spectroscopic analysis of bis-Betti base derivatives of 2,3-dihydroxynaphthalene.

    Science.gov (United States)

    Zamani, Mehdi; Shafiee, Mehdi; Keshavarz, Mohammad Hossein

    2016-04-01

    Density functional theory (DFT) was used to study the stereochemistry, thermodynamic stability, and spectra of recently synthesized bis-Betti base derivatives of 2,3-dihydroxynaphthalene obtained through multicomponent reactions of 2,3-dihydroxynaphthalene with aminoisoxazole and benzaldehyde derivatives. The stereochemistry of the products was investigated by theoretically calculating the infrared (IR) and proton nuclear magnetic resonance ((1)H NMR) spectra of the diastereomers and comparing them to the corresponding experimental data. The thermochemical properties of the reactions, including the enthalpy, internal energy, entropy, and Gibbs free energy, were also calculated. The diastereoselectivity of the reactions was estimated from the equilibrium distribution of diastereomers. According to the results, the synthesis of bis-Betti bases is exothermic and accompanied by a decrease in entropy. The energy difference between the diastereomers is quite small, but the Gibbs free energy change for the equilibrium syn anti favors the anti over syn configuration. These results are in good agreement with experimental observations.

  6. Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones

    Science.gov (United States)

    Subramanian, M.; Vanangamudi, G.; Thirunarayanan, G.

    2013-06-01

    A series of 2,5-dimethyl-3-furyl chalcones [2E-1-(2,5-dimethyl-3-furyl)-3-(substituted phenyl)-2-propen-1-ones] have been synthesized by Hydrotalcite catalyzed aldol condensation between 3-acetyl-2,5-dimethylfuron and substituted benzaldehydes. Yields of chalcones are more than 80%. These chalcones were characterized by their physical constants and spectral data. The group frequencies of infrared ν(cm-1) of CO s-cis and s-trans, CH in-plane and out of plane, CHdbnd CH out of plane, lbond2 Cdbnd Crbond2 out of plane modes, NMR chemical shifts δ(ppm) of Hα, Hβ, CO, Cα and Cβ of these chalcones were correlated with Hammett substituent constants, F and R parameters using single and multi-regression analyses. From the results of statistical analyses, the effects of substituents on the group frequencies are explained. Antibacterial, antifungal and insect antifeedant activities of these chalcones have been studied.

  7. Synthesis and pharmacological investigation of 2-(4-dimethylaminophenyl)-3,5-disubstituted thiazolidin-4-ones as anticonvulsants.

    Science.gov (United States)

    Senthilraja, Manavalan; Alagarsamy, Veerachamy

    2012-10-01

    A new series of 2-(4-dimethylaminophenyl)-3-substituted thiazolidin-4-one-5-yl-acetyl acetamides/benzamides were synthesized by the nucleophilic substitution of 3-substituted-2-(4-dimethylaminophenyl)-thiazolidin-4-one-5-yl-acetylchloride with acetamide and benzamide. The starting material 3-substituted-2-(4-dimethylaminophenyl)-thiazolidin-4-one-5-yl-acetylchloride was synthesized from 3-substituted-2-(4-dimethylaminophenyl)-thiazolidin-4-one-5-yl-acetic acid, which in turn was prepared by one-pot reaction of amino component, p-dimethylamino benzaldehyde and mercapto succinic acid. The title compounds were investigated for their anticonvulsant activities; among the test compounds, compound 2-(4-dimethylaminophenyl)-3-phenylamino-thiazolidine-4-one-5-yl-acetylbenzamide (14) emerged as the most active compound of the series and as moderately more potent than the reference standard diazepam.

  8. Fuzzy Support Vector Regression Model of 4-CBA Concentration for Industrial PTA Oxidation Process%工业PTA氧化工程中4-CBA浓度的模糊支持向量回归模型

    Institute of Scientific and Technical Information of China (English)

    张英; 苏宏业; 刘瑞兰; 褚健

    2005-01-01

    In the past few years, support vector machines (SVMs) have been applied to many fields, such as pattern recognition and data mining, etc. However there still exist some problems to be solved. One of them is that the SVM is very sensitive to outliers or noises because of over-fitting problem. In this paper, a fuzzy support vector regression (FSVR) method is presented to deal with this problem. Strategies based on k nearest neighbor (kNN) and support vector data description (SVDD) are adopted to set the fuzzy membership values of data points in FSVR.The proposed FSVR soft sensor models based on kNN and SVDD are employed to predict the concentration of 4-carboxy-benzaldehyde (4-CBA) in purified terephthalic acid (PTA) oxidation process. Simulation results indicate that the proposed method indeed reduces the effect of outliers and yields higher accuracy.

  9. Ruthenium(II) complexes containing bidentate Schiff bases and triphenylphosphine or triphenylarsine

    Indian Academy of Sciences (India)

    P Viswanathamurthi; R Karvembu; V Tharaneeswaran; K Natarajan

    2005-05-01

    Reactions of ruthenium(II) complexes [RuHX(CO)(EPh3)2(B)] (X = H or Cl; B = EPh3, pyridine (py) or piperidine (pip); E = P or As) with bidentate Schiff base ligands derived by condensing - hydroxyacetophenone with aniline, - or -methylaniline have been carried out. The products were characterized by analytical, IR, electronic and 1H-NMR spectral studies and are formulated as [Ru(X)(CO) (L)(EPh3)(B)] (L = Schiff base anion; X = H or Cl; B = EPh3, py or pip; E = P or As). An octahedral structure has been tentatively proposed for the new complexes. The new complexes were tested for their catalytic activities in the oxidation of benzyl alcohol to benzaldehyde.

  10. Design, Synthesis and Inclusion Properties of Butterfly-shaped Hosts

    Institute of Scientific and Technical Information of China (English)

    郭文生; 徐赫男; 郭放; 佟健

    2005-01-01

    Two kinds of """"buuerfly-shaped"""" host compounds, 2,5-bis(triphenylmethyl)hydroquinone (1) and 2,5-bis(diphenylmethyl)hydroquinone (2) were designed and synthesized. 1 and 2 can form inclusion complexes with various small organic molecules. These inclusion complexes were determined by 1H NMR spectroscopy, and the results were as follows: 1·DMF (1:2), 1·DMSO (1:2), lopyridine (1:2), locyclopentanone (2:3); 2oDMF (12), 2·THF (1:1), 2·benzaidehyde (1:2), 2·2,5-hexanedione (1:1), 2·N-methyl-2-pyrrolidone (1:3). The complex structure of 2 with benzaldehyde was determined by single crystal X-my diffraction analysis and the crystalstructure is stabilized by intermolecular hydrogen bonds.

  11. Synthesis and Crystal Structure of (R)-4-Hydroxymethyl-2-thioxo Thiazolidine and Its Asymmetric Catalysis

    Institute of Scientific and Technical Information of China (English)

    LI Jing; SHANG Yan-mei; XIAO Chuan; SONG Zhi-guang; LI Ye-zhi; HUANG Hua-min

    2009-01-01

    (R)-4-Hydroxymethyl-2-thioxo thiazolidine as a new chiral catalyst in the asymmetric addition of diethyl-zinc to benzaldehyde was synthesized from (R)-4-hydroxymethyl-2-thioxo thiazolidine carboxylic acid and its crystal structure was determined by X-ray diffraction method. The compound was crystallized in the orthorhombic system, space group P212121 with unit cell dimensions a=0.67253(12) nm; b=0.89164(17) rim; c=1.06146(19) nm, volume 0.6365(2) nm3; Z=4, calculated denisity 1.557 Mg/m3; absorption coefficient 0.733 mm-1; F(000)=312. The X-ray crystal structure analysis reveals that the compound has a thione group.

  12. A Ruthenium(III)-Oxyl Complex Bearing Strong Radical Character.

    Science.gov (United States)

    Shimoyama, Yoshihiro; Ishizuka, Tomoya; Kotani, Hiroaki; Shiota, Yoshihito; Yoshizawa, Kazunari; Mieda, Kaoru; Ogura, Takashi; Okajima, Toshihiro; Nozawa, Shunsuke; Kojima, Takahiko

    2016-11-02

    Proton-coupled electron-transfer oxidation of a Ru(II) -OH2 complex, having an N-heterocyclic carbene ligand, gives a Ru(III) -O(.) species, which has an electronically equivalent structure of the Ru(IV) =O species, in an acidic aqueous solution. The Ru(III) -O(.) complex was characterized by spectroscopic methods and DFT calculations. The oxidation state of the Ru center was shown to be close to +3; the Ru-O bond showed a lower-energy Raman scattering at 732 cm(-1) and the Ru-O bond length was estimated to be 1.77(1) Å. The Ru(III) -O(.) complex exhibits high reactivity in substrate oxidation under catalytic conditions; particularly, benzaldehyde and the derivatives are oxidized to the corresponding benzoic acid through C-H abstraction from the formyl group by the Ru(III) -O(.) complex bearing a strong radical character as the active species.

  13. Synthesis of platinum and palladium complexes with bis-(hydroxy imines

    Directory of Open Access Journals (Sweden)

    Lucas M. Arantes

    2012-06-01

    Full Text Available The Schiff bases are an important class of compounds well used as ligands in coordination chemistry. The functionalized bis-imines, that represent a specific group of Schiff base, have been studied in our research group both for the evaluation of biological activity, against fungi and cancer, as for organocatalyst. Here the bis-imines 1 and 4 were synthesized in good yields by condensation of hydroxylated benzaldehydes with phenylenediamines. After that they were matched with Platinum and palladium salts providing three metallic complex (2, 3 and 5 that were fully characterized by nuclear magnetic resonance and mass spectrometry with electrospray ionization. Now these complexes are being tested in cross-coupling reactions of Heck and Suzuki.

  14. Gold Nanoparticles Supported on a Layered Double Hydroxide as Efficient Catalysts for the One-Pot Synthesis of Flavones.

    Science.gov (United States)

    Yatabe, Takafumi; Jin, Xiongjie; Yamaguchi, Kazuya; Mizuno, Noritaka

    2015-11-02

    Flavones are a class of natural products with diverse biological activities and have frequently been synthesized by step-by-step procedures using stoichiometric amounts of reagents. Herein, a catalytic one-pot procedure for the synthesis of flavone and its derivatives is developed. In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various kinds of flavones can be synthesized starting from 2'-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). The present one-pot procedure consists of a sequence of several reactions, and Au/LDH can catalyze all these different types of reactions. The catalysis is shown to be truly heterogeneous, and Au/LDH can be readily recovered and reused.

  15. Functionalized SBA-15 supported nickel (II)-oxime-imine catalysts for liquid phase oxidation of olefins under solvent-free conditions

    Science.gov (United States)

    Paul, Luna; Banerjee, Biplab; Bhaumik, Asim; Ali, Mahammad

    2016-05-01

    A new oxime-imine functionalized highly ordered mesoporous SBA-15 (SBA-15-NH2-DAMO) has been synthesized via post-synthesis functionalization of SBA-15 with 3-aminopropyl-triethoxysilane followed by the Schiff base condensation with diacetylmonooxime, which was further reacted with Ni(ClO4)2 to yield the functionalized nickel catalyst SBA-15-NH2-DAMO-Ni. All the synthesized materials were thoroughly characterized using different characterization techniques. It was found that SBA-15-NH2-DAMO-Ni catalyzes the one-pot oxidation of olefins like styrene, cyclohexene, cyclooctene, 1-hexene and 1-octene to the corresponding benzaldehyde, cyclohexene-1-ol and cyclooctene-oxide, respectively under solvent-free conditions by using tert-butylhydroperoxide as oxidant.

  16. CeO2-modified Au@SBA-15 nanocatalysts for liquid-phase selective oxidation of benzyl alcohol

    Science.gov (United States)

    Wang, Tuo; Yuan, Xiang; Li, Shuirong; Zeng, Liang; Gong, Jinlong

    2015-04-01

    Tuning the interfacial perimeter and structure is crucial to understanding the origin of catalytic performance. This paper describes the design, characterization, and application of CeO2 modified Au@SBA-15 (Au-CeO2@SBA-15) catalysts in selective oxidation of benzyl alcohol. The reaction results showed that Au-CeO2@SBA-15 catalysts exhibited higher catalytic activity compared with Au@SBA-15 and Au/CeO2 catalysts under identical conditions along with the high selectivity towards benzaldehyde (>99%). The turnover frequency of benzyl alcohol over the Au-100CeO2@SBA-15 catalyst is about nine-fold and four-fold higher than those of Au@SBA-15 and Au/CeO2 catalysts, respectively. The supported catalysts were characterized by N2 adsorption-desorption, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, transmission electron microscopy, high-angle annular dark-field scanning transmission electron microscopy, scanning transmission electron microscopy-energy dispersive spectrometry, and X-ray photoelectron spectroscopy. It was found that the Au and small CeO2 nanoparticles (~5 nm) were homogeneously mixed in the channels of SBA-15, which led to an increase in the interfacial area between Au and CeO2 and consequently a better catalytic performance of Au-CeO2@SBA-15 catalysts for the selective oxidation of benzyl alcohol to benzaldehyde compared with that of Au/CeO2. The prevention of agglomeration and leaching of Au nanoparticles by restricting them inside the mesopores of SBA-15 was conducive to the stable existence of large quantities of Au-CeO2 interface, which leads to high stability of the Au-CeO2@SBA-15 catalyst.Tuning the interfacial perimeter and structure is crucial to understanding the origin of catalytic performance. This paper describes the design, characterization, and application of CeO2 modified Au@SBA-15 (Au-CeO2@SBA-15) catalysts in selective oxidation of benzyl alcohol. The reaction results showed that Au-CeO2@SBA-15 catalysts

  17. AMYGDALIN AND ITS EFFECTS ON ANIMAL CELLS

    Directory of Open Access Journals (Sweden)

    Marek Halenár

    2013-02-01

    Full Text Available Amygdalin is a natural compound whose anticancer, anti-inflammatory activity and other medicinal benefits have been known for many years. It has been isolated in 1830 by the French chemists Robiquet and Boutron-Charlard from kernels of the bitter almond (Prunus amygdalus. It is a major component of the seeds of prunasin family plants, such as apricots, almonds, peaches, apples, and other rosaceous plants. Amygdalin is composed of two molecules of glucose, one of benzaldehyde, which induces an analgesic action, and one of hydrocyanic acid, which is an anti-neoplastic compound. It has been used as a traditional drug because of its wide range of medicinal benefits. Amygdalin can be used in medicine for preventing and treating migraine, hypertension, chronic inflammation, and other reaction source diseases. This review is focused on the effects of amygdalin on the animal system.

  18. Solvent-dependent switch of ligand donor ability and catalytic activity of ruthenium(II) complexes containing pyridinylidene amide (PYA) N-heterocyclic carbene hybrid ligands.

    Science.gov (United States)

    Leigh, Vivienne; Carleton, Daniel J; Olguin, Juan; Mueller-Bunz, Helge; Wright, L James; Albrecht, Martin

    2014-08-04

    Chelating ligands incorporating both N-[1-alkylpyridin-4(1H)-ylidene]amide (PYA) and N-heterocyclic carbene (NHC) donor sites were prepared and used for the synthesis of ruthenium(II) complexes. Cyclic voltammetry, NMR, and UV-vis spectroscopy of the complexes indicate a solvent-dependent contribution of the limiting resonance structures associated with the ligand in solution. The neutral pyridylidene imine structure is more pronounced in apolar solvents (CH2Cl2), while the mesoionic pyridinium amide form is predominant in polar solvents (MeOH, DMSO). The distinct electronic properties of these hybrid PYA-NHC ligands in different solvents have a direct influence on the catalytic activity of the ruthenium center, e.g., in the dehydrogenation of benzyl alcohol to benzaldehyde. The activity in different solvents qualitatively correlates with the solvent permittivity.

  19. Production of a cyanogenic secretion by a thyridid caterpillar (Calindoea trifascialis, Thyrididae, Lepidoptera)

    Science.gov (United States)

    Darling, Christopher; Schroeder, Frank; Meinwald, Jerrold; Eisner, Maria; Eisner, Thomas

    2001-06-01

    The thyridid caterpillar, Calindoea trifascialis, when disturbed, emits a defensive secretion from two sac-like glands that open dorsolaterally on the first abdominal segment. The larva has two arm-like protuberances that project outward from the body just in front of the gland openings. These "arms", which are wetted by secretion when the larva activates its glands, appear to function specifically for administration of the fluid. A primary component of the secretion is mandelonitrile, a cyanogenic compound, but the fluid also contains other potential deterrents, including benzaldehyde, benzoic acid, (E,E)-α-farnesene, and 3-methylbutyl-3-methylbutanoate. Tests done in the field in Vietnam, where the species is native, showed the secretion to be protective against ants.

  20. Bis-(1-2-benzopyran-1-one) derivatives: Synthesis and antimicrobial evaluation

    Indian Academy of Sciences (India)

    Poonam Kumar Koppula; Nalini Purohit

    2013-11-01

    The aim of the present study was to synthesize isocoumarin heterocycles and to elucidate the potential role of these compounds as biological active agents. A new series of isocoumarin derivatives containing two six-membered lactone rings is reported. 3-Aroyl-substituted isocoumarins (3) obtained by condensing 2-carboxy benzaldehyde (1) with bromoacetophenone derivatives (2) was further reacted with different aromatic aldehydes (4) affording bis-(1-2-benzopyran-1-one) derivatives (5). This short review compiles examples of most promising antibacterial, antifungal and analgesic bis-(1H-2-benzopyran-1-one) derivatives. The products were characterized on the basis of analytical and spectral (IR, 1HNMR, C13NMR, Mass) data. The biological activity study revealed that all compounds showed promising activities and bis-(1-2-benzopyran-1-one) derivatives (5) were found to be more active than 3-aroyl-substituted isocoumarins (3).