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Sample records for benzaldehyde

  1. Overtone spectroscopy of some benzaldehyde derivatives

    Indian Academy of Sciences (India)

    chlorobenzaldehyde have been undertaken with the following objectives: 1. To see if the Fermi resonance seen in the alkyl CH stretch region for benzaldehyde, ortho hydroxy and methoxy benzaldehydes is present in the present group of com- pounds.

  2. Enhancement of reaction rates for catalytic benzaldehyde ...

    Indian Academy of Sciences (India)

    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.

  3. Enhancement of reaction rates for catalytic benzaldehyde ...

    Indian Academy of Sciences (India)

    Abstract. 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 ...

  4. 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...

  5. Final report on the safety assessment of benzaldehyde.

    Science.gov (United States)

    Andersen, Alan

    2006-01-01

    Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. Currently used in only seven cosmetic products, its highest reported concentration of use was 0.5% in perfumes. Benzaldehyde is a generally regarded as safe (GRAS) food additive in the United States and is accepted as a flavoring substance in the European Union. Because Benzaldehyde rapidly metabolizes to Benzoic Acid in the skin, the available dermal irritation and sensitization data demonstrating no adverse reactions to Benzoic Acid were considered supportive of the safety of Benzaldehyde. Benzaldehyde is absorbed through skin and by the lungs, distributes to all well-perfused organs, but does not accumulate in any specific tissue type. After being metabolized to benzoic acid, conjugates are formed with glycine or glucuronic acid, and excreted in the urine. Little acute toxicity was seen. The oral LD(50) of Benzaldehyde in rats and mice ranged from 800 to 2850 mg/kg. The intraperitoneal LD(50) in white rats was 3265 mg/kg. In short-term oral studies, the no observed adverse effect level (NOAEL) was 400 mg/kg in rats and mice. In subchronic oral studies, the NOAEL was 400 mg/kg in rats and 600 mg/kg in mice. In a 16-week feeding study, rats given up to 10,000 ppm showed no signs of toxicity. Repeated inhalation of volatilized Benzaldehyde produced ocular and nasal irritation at 500 ppm and death in rabbits at 750 ppm. Undiluted Benzaldehyde was irritating to rabbit eyes, causing edema, erythema, and pain. Benzaldehyde was determined not to be a contact sensitizer, but did produce allergic reactions in a maximization test. Clinical reports of allergy to Benzaldehyde are rare. Benzoic Acid did not produce irritation or sensitization reactions in human clinical studies. Benzoic Acid also failed to produce reactions in phototoxicity and photosensitization tests. Neither Benzaldehyde, Benzoic Acid, nor Sodium Benzoate are reproductive or developmental

  6. Hydrogen bonds and antiviral activity of benzaldehyde derivatives

    Science.gov (United States)

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

    2012-09-01

    We have obtained the Fourier transform IR spectra of solutions of benzaldehyde derivatives having different antiviral activities against a herpes virus. We observe a correlation between the presence of hydrogen bonds in the benzaldehyde molecules and the appearance of antiviral properties in the compounds. For compounds having antiviral activity, we have obtained spectral data suggesting the existence of hydrogen bonds of the type C=OṡṡṡH-O and O-HṡṡṡO in the molecules. When the hydrogen atom in the hydroxyl groups are replaced by a methyl group, no intramolecular hydrogen bonds are formed and the compounds lose their antiviral activity.

  7. 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...

  8. 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.

    2016-01-01

    Many non-cigarette tobacco products, including e-cigarettes, contain various flavorings, such as fruit flavours. Although many flavorings used in e-cigarettes are generally recognized 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 flavors, 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 flavored e-cigarettes purchased online and detected benzaldehyde in 108 out of 145 products. The highest levels of benzaldehyde were detected in cherry flavored products. The benzaldehyde doses inhaled with 30 puffs from flavored e-cigarettes were often higher than doses inhaled from a conventional cigarette. Levels in cherry flavored products were over 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 flavoring ingredients such as benzaldehyde, clinicians need to be aware of this emerging risk and ask their patients about use of flavored e-cigarettes. PMID:26822067

  9. Facile Synthesis of Benzaldehyde-Functionalized Ionic Liquids and Their Flexible Functional Group Transformations

    OpenAIRE

    Huang, Qiang; Zheng, Baozhong

    2012-01-01

    Three benzaldehyde-functionalized ionic liquids were readily synthesized by quaternization of N-alkylimidazole with benzaldehyde-functionalized alkyl bromides under microwave irradiation in good yield. These aldehyde-functionalized ionic liquids could easily be oxidized in the presence of H2O2/KOH or be reduced by NaBH4 leading to the formation of the corresponding carboxyl-functionalized ionic liquids or benzylic alcohol-functionalized ionic liquids. In addition, the condensations of these f...

  10. Solubilities of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures

    International Nuclear Information System (INIS)

    Wang, Hui; Wang, Qinbo; Xiong, Zhenhua; Chen, Chuxiong; Shen, Binwei

    2015-01-01

    Highlights: • Solubilities of benzoic acid in (benzyl alcohol + benzaldehyde) mixtures were measured at 1 atm. • The experimental temperature ranges at (298.35 to 355.65) K. • Effects of benzyl alcohol mass concentration at (0.00 to 1.00) on the solubilities of benzoic acid were studied. • The experimental data were correlated with NRTL model. • Thermodynamic functions of dissolution of benzoic acid in (benzyl alcohol + benzaldehyde) mixtures were discussed. - Abstract: The solubility of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures was measured at temperature from (298.35 to 355.65) K and atmospheric pressure. The measured solubility increases with the increasing temperature at constant solvent composition. The effects of mass fraction benzaldehyde in the solvent mixtures at (0.0 to 1.00) on the solubility were studied. The measured solubility decreases with the increasing mass fraction of benzaldehyde. The experimental results were correlated with the non-random two-liquid (NRTL) equations, and good agreement between the correlated and the experimental values was obtained. Thermodynamic functions for the solution of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures were calculated with the van’t Hoff plot. The apparent dissolution Gibbs free energy change was also calculated

  11. 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

  12. OPTIMIZATION OF TIME REACTION AND HYDROXIDE ION CONCENTRATION ON FLAVONOID SYNTHESIS FROM BENZALDEHYDE AND ITS DERIVATIVES

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    Sri Handayani

    2010-06-01

    Full Text Available The aim of this research is to determine the optimum time of reaction and concentration of hydroxide ion on chalcone, 4-methoxychalcone and 3,4-dimethoxychalcone synthesis. Chalcone and its derivatives were synthesized by dissolving KOH in ethanol followed by dropwise addition of acetophenone and benzaldehyde. Then, the mixture was stirred for several hours. Three benzaldehydes has been used, i.e : benzaldehyde, p-anysaldehyde and veratraldehyde. The time of reaction was varied for, 12, 18, 24, 30 and 36 hours. Furthermore, on the optimum reaction time for each benzaldehyde the hydroxyl ion concentration was varied from 5,7,9,11 and 13%(w/v. The results of this research suggested that the optimum time of chalchone synthesis was 12 hours, while, 4-methoxychalcone and 3,4-dimethoxychalcone were 30 hours. The optimum concentration of hydroxide ion of chalcone synthesis was 13% and for 4-methoxychalcone and 3,4-dimethoxychalcone were 11%. Keywords: Chalcone synthesis, time of reaction, hydroxide ion concentration.

  13. Effects of hydroxylated benzaldehyde derivatives on radiation-induced reactions involving various organic radicals

    Science.gov (United States)

    Ksendzova, G. A.; Samovich, S. N.; Sorokin, V. L.; Shadyro, O. I.

    2018-05-01

    In the present paper, the effects of hydroxylated benzaldehyde derivatives and gossypol - the known natural occurring compound - on formation of decomposition products resulting from radiolysis of ethanol and hexane in deaerated and oxygenated solutions were studied. The obtained data enabled the authors to make conclusions about the effects produced by the structure of the compounds under study on their reactivity towards oxygen- and carbon-centered radicals. It has been found that 2,3-dihydroxybenzaldehyde, 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde and 4,6-di-tert-butyl-3-(1,3-dioxane-2-yl)-1,2-dihydroxybenzene are not inferior in efficiency to butylated hydroxytoluene - the industrial antioxidant - as regards suppression of the radiation-induced oxidation processes occurring in hexane. The derivatives of hydroxylated benzaldehydes were shown to have a significant influence on radiation-induced reactions involving α-hydroxyalkyl radicals.

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

    Directory of Open Access Journals (Sweden)

    Hongling Han

    2015-07-01

    Full Text Available 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.

  15. Olfactory receptors on the maxillary palps of small ermine moth larvae: evolutionary history of benzaldehyde sensitivity

    Science.gov (United States)

    Xu, Sen; Menken, Steph B. J.

    2007-01-01

    In lepidopterous larvae the maxillary palps contain a large portion of the sensory equipment of the insect. Yet, knowledge about the sensitivity of these cells is limited. In this paper a morphological, behavioral, and electrophysiological investigation of the maxillary palps of Yponomeuta cagnagellus (Lepidoptera: Yponomeutidae) is presented. In addition to thermoreceptors, CO2 receptors, and gustatory receptors, evidence is reported for the existence of two groups of receptor cells sensitive to plant volatiles. Cells that are mainly sensitive to (E)-2-hexenal and hexanal or to (Z)-3-hexen-1-ol and 1-hexanol were found. Interestingly, a high sensitivity for benzaldehyde was also found. This compound is not known to be present in Euonymus europaeus, the host plant of the monophagous Yponomeuta cagnagellus, but it is a prominent compound in Rosaceae, the presumed hosts of the ancestors of Y. cagnagellus. To elucidate the evolutionary history of this sensitivity, and its possible role in host shifts, feeding responses of three Yponomeuta species to benzaldehyde were investigated. The results confirm the hypothesis that the sensitivity to benzaldehyde evolved during the ancestral shift from Celastraceae to Rosaceae and can be considered an evolutionary relict, retained in the recently backshifted Celastraceae-specialist Y. cagnagellus. PMID:17372741

  16. Kinetic α secondary deuterium isotope effects for O-ethyl S-phenyl benzaldehyde acetal hydrolysis

    International Nuclear Information System (INIS)

    Ferraz, J.P.; Cordes, E.H.

    1979-01-01

    The rate of hydrolysis of O-ethyl S-phenyl benzaldehyde acetal at 25 0 C in 20% dioxane--80% water is independent of pH over the range pH6-12; k/sub obsd/ = 1.9 x 10 -7 s -1 . Under more acidic conditions, the rate increases linearly with the activity of the hydrated proton; k 2 = 2.95 x 10 -2 M -1 s -1 . The kinetic α secondary deuterium isotope effect for acid-catalyzed hydrolysis of O-ethyl S-phenyl benzaldehyde acetal, measured at 25 0 C in 20% aqueous dioxane containing 0.05 M HCl, is k/sub H//k/sub D/ = 1.038 +- 0.008, a value consistent with a transition state in which the C--S bond is stretched rather little. In contrast, the corresponding isotope effect for the pH-independent hydrolysis of this substrate, measured at 42.5 0 C in 20% dioxane, is 1.13 +- 0.02, a value consistent with complete C--S bond cleavage in the transition state and rate-determining diffusion apart of the ion-pair formed as the initial intermediate, in accord with the suggestion of Jensen and Jencks. 1 figure, 4 tables

  17. Enzymatic reduction of 4-(dimethylamino)benzaldehyde with carrot bits (Daucus carota): a simple experiment for understanding biocatalysis

    International Nuclear Information System (INIS)

    Omori, Alvaro Takeo; Portas, Viviane Barbosa; Oliveira, Camila de Souza de

    2012-01-01

    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)

  18. Highly selective oxidation of styrene to benzaldehyde over a tailor-made cobalt oxide encapsulated zeolite catalyst.

    Science.gov (United States)

    Liu, Jiangyong; Wang, Zihao; Jian, Panming; Jian, Ruiqi

    2018-05-01

    A tailor-made catalyst with cobalt oxide particles encapsulated into ZSM-5 zeolites (Co 3 O 4 @HZSM-5) was prepared via a hydrothermal method with the conventional impregnated Co 3 O 4 /SiO 2 catalyst as the precursor and Si source. Various characterization results show that the Co 3 O 4 @HZSM-5 catalyst has well-organized structure with Co 3 O 4 particles compatibly encapsulated in the zeolite crystals. The Co 3 O 4 @HZSM-5 catalyst was employed as an efficient catalyst for the selective oxidation of styrene to benzaldehyde with hydrogen peroxide as a green and economic oxidant. The effect of various reaction conditions including reaction time, reaction temperature, different kinds of solvents, styrene/H 2 O 2 molar ratio and catalyst dosage on the catalytic performance were systematically investigated. Under the optimized reaction condition, the yield of benzaldehyde can achieve 78.9% with 96.8% styrene conversion and 81.5% benzaldehyde selectivity. Such an excellent catalytic performance can be attributed to the synergistic effect between the confined reaction environment and the proper acidic property. In addition, the reaction mechanism with Co 3 O 4 @HZSM-5 as the catalyst for the selective oxidation of styrene to benzaldehyde was reasonably proposed. Copyright © 2018 Elsevier Inc. All rights reserved.

  19. 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...

  20. Kinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes.

    Science.gov (United States)

    Panoutsopoulos, Georgios I; Beedham, Christine

    2004-01-01

    Molybdenum-containing enzymes, aldehyde oxidase and xanthine oxidase, are important in the oxidation of N-heterocyclic xenobiotics. However, the role of these enzymes in the oxidation of drug-derived aldehydes has not been established. The present investigation describes the interaction of eleven structurally related benzaldehydes with guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase, since they have similar substrate specificity to human molybdenum hydroxylases. The compounds under test included mono-hydroxy and mono-methoxy benzaldehydes as well as 3,4-dihydroxy-, 3-hydroxy-4-methoxy-, 4-hydroxy-3-methoxy-, and 3,4-dimethoxy-benzaldehydes. In addition, various amines and catechols were tested with the molybdenum hydroxylases as inhibitors of benzaldehyde oxidation. The kinetic constants have shown that hydroxy-, and methoxy-benzaldehydes are excellent substrates for aldehyde oxidase (Km values 5x10(-6) M to 1x10(-5) M) with lower affinities for xanthine oxidase (Km values around 10(-4) M). Therefore, aldehyde oxidase activity may be a significant factor in the oxidation of the aromatic aldehydes generated from amines and alkyl benzenes during drug metabolism. Compounds with a 3-methoxy group showed relatively high Vmax values with aldehyde oxidase, whereas the presence of a 3-hydroxy group resulted in minimal Vmax values or no reaction. In addition, amines acted as weak inhibitors, whereas catechols had a more pronounced inhibitory effect on the aldehyde oxidase activity. It is therefore possible that aldehyde oxidase may be critical in the oxidation of the analogous phenylacetaldehydes derived from dopamine and noradrenaline.

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

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    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.

  2. Biocidal polymers: synthesis and antimicrobial properties of benzaldehyde derivatives immobilized onto amine-terminated polyacrylonitrile

    Science.gov (United States)

    2012-01-01

    Background The design and applications of antimicrobial polymers is a growing field. Antimicrobial polymers can help to solve the problems associated with the use of conventional antimicrobial agents. Polymers with active functional groups can act as a carrier system for antimicrobial agents. In our study, we aim to prepare and develop some antimicrobial polymers for biomedical applications and water treatment. Results The antimicrobial polymers based on polyacrylonitrile (PAN) were prepared. Functional groups were created onto polyacrylonitrile via amination using different types of diamines such as ethylenediamine (EDA) and hexamethylenediamine (HMDA) to yield amine-terminated polymers. Antimicrobial polymers were obtained by immobilization of benzaldehyde and its derivatives which include, 4-hydroxybenzaldehyde and 2,4-dihydroxybenzaldehyde onto amine-terminated polymers. The antimicrobial activity of the prepared polymers against different types of microorganisms including Gram-positive bacteria (Staphylococcus aureus), Gram-negative bacteria (Pseudomonas aeruginosa; Escherichia coli; and Salmonella typhi) as well as fungi (Aspergillus flavus, Aspergillus niger, Candida albicans, Cryptpcoccus neoformans) were explored by the cut plug method and viable cell counting methods. Conclusions Amine-terminated polyacrylonitrile were used as a novel polymeric carrier for benzaldehyde derivatives as antimicrobial agents. The prepared polymers can inhibit the growth of the microorganisms. The activity was varied according to the tested microorganism as well as the polymer microstructure. It was found that the activity increased with increasing the number phenolic hydroxyl group of the bioactive group. Finally, it is anticipated that the prepared antimicrobial polymers would be of great help in the field of biomedical applications and biological water treatment. PMID:23025798

  3. Biocidal polymers: synthesis and antimicrobial properties of benzaldehyde derivatives immobilized onto amine-terminated polyacrylonitrile

    Directory of Open Access Journals (Sweden)

    Alamri Abdullah

    2012-10-01

    Full Text Available Abstract Background The design and applications of antimicrobial polymers is a growing field. Antimicrobial polymers can help to solve the problems associated with the use of conventional antimicrobial agents. Polymers with active functional groups can act as a carrier system for antimicrobial agents. In our study, we aim to prepare and develop some antimicrobial polymers for biomedical applications and water treatment. Results The antimicrobial polymers based on polyacrylonitrile (PAN were prepared. Functional groups were created onto polyacrylonitrile via amination using different types of diamines such as ethylenediamine (EDA and hexamethylenediamine (HMDA to yield amine-terminated polymers. Antimicrobial polymers were obtained by immobilization of benzaldehyde and its derivatives which include, 4-hydroxybenzaldehyde and 2,4-dihydroxybenzaldehyde onto amine-terminated polymers. The antimicrobial activity of the prepared polymers against different types of microorganisms including Gram-positive bacteria (Staphylococcus aureus, Gram-negative bacteria (Pseudomonas aeruginosa; Escherichia coli; and Salmonella typhi as well as fungi (Aspergillus flavus, Aspergillus niger, Candida albicans, Cryptpcoccus neoformans were explored by the cut plug method and viable cell counting methods. Conclusions Amine-terminated polyacrylonitrile were used as a novel polymeric carrier for benzaldehyde derivatives as antimicrobial agents. The prepared polymers can inhibit the growth of the microorganisms. The activity was varied according to the tested microorganism as well as the polymer microstructure. It was found that the activity increased with increasing the number phenolic hydroxyl group of the bioactive group. Finally, it is anticipated that the prepared antimicrobial polymers would be of great help in the field of biomedical applications and biological water treatment.

  4. 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.

  5. Hydrogenation of benzaldehyde via electrocatalysis and thermal catalysis on carbon-supported metals

    Energy Technology Data Exchange (ETDEWEB)

    Song, Yang; Sanyal, Udishnu; Pangotra, Dhananjai; Holladay, Jamie D.; Camaioni, Donald M.; Gutiérrez, Oliver Y.; Lercher, Johannes A.

    2018-03-01

    Abstract Selective reduction of benzaldehyde to benzyl alcohol on C-supported Pt, Rh, Pd, and Ni in aqueous phase was conducted using either directly H2 (thermal catalytic hydrogenation, TCH) or in situ electrocatalytically generated hydrogen (electrocatalytic hydrogenation, ECH). In TCH, the intrinsic activity of the metals at room temperature and 1 bar H2 increased in the sequence Rh/C < Pt/C < Pd/C, while Ni/C is inactive at these conditions due to surface oxidation in the absence of cathodic potential. The reaction follows a Langmuir-Hinshelwood mechanism with the second hydrogen addition to the adsorbed hydrocarbon being the rate-determining step. All tested metals were active in ECH of benzaldehyde, although hydrogenation competes with the hydrogen evolution reaction (HER). The minimum cathodic potentials to obtain appreciable ECH rates were identical to the onset potentials of HER. Above this onset, the relative rates of H reacting to H2 and H addition to the hydrocarbon determines the selectivity to ECH and TCH. Accordingly, the selectivity of the metals towards ECH increases in the order Ni/C < Pt/C < Rh/C < Pd/C. Pd/C shows exceptionally high ECH selectivity due to its surprisingly low HER reactivity under the reaction conditions. Acknowledgements The authors would like to thank the groups of Hubert A. Gasteiger at the Technische Universität München of Jorge Gascon at the Delft University of Technology for advice and valuable discussions. The authors are grateful to Nirala Singh, Erika Ember, Gary Haller, and Philipp Rheinländer for fruitful discussions. We are also grateful to Marianne Hanzlik for TEM measurements and to Xaver Hecht and Martin Neukamm for technical support. Y.S. would like to thank the Chinese Scholarship Council for the financial support. The research described in this paper is part of the Chemical Transformation Initiative at Pacific Northwest National Laboratory (PNNL), conducted under the Laboratory Directed Research and

  6. Application of molecular topology to the prediction of the phenoloxidase inhibition by a group of benzaldehyde thiosemicarbazone and their derivatives

    OpenAIRE

    García-Domenech, Ramón; Calvo-Chamorro, María L.; Cuervo-Arias, Angélica Y.; Gómez-Sucerquia, Leysa J.; Ortega-Chávez, Verónica; Pérez-Torrado, Eva; Gálvez, Jorge

    2008-01-01

    A topological-mathematical model has been arranged to search for new derivatives of benzaldehyde thiosemicarbazone and related compounds acting as phenoloxidase inhibitors. By using multilinear regression analysis a function with two descriptors, 1χv, 4χpv and r2 = 0,940 was capable to predict adequately the IC50 for each compound.After carrying out a virtual screening based upon such a model, new structures potentially active against the enzyme are proposed.

  7. Structural, thermal and optical characterization of an organic NLO material—Benzaldehyde thiosemicarbazone monohydrate single crystals

    Science.gov (United States)

    Santhakumari, R.; Ramamurthi, K.

    2011-02-01

    Single crystals of the organic NLO material, benzaldehyde thiosemicarbazone (BTSC) monohydrate, were grown by slow evaporation method. Solubility of BTSC monohydrate was determined in ethanol at different temperatures. The grown crystals were characterized by single crystal X-ray diffraction analysis to determine the cell parameters and by FT-IR technique to study the presence of the functional groups. Thermogravimetric and differential thermal analyses reveal the thermal stability of the crystal. UV-vis-NIR spectrum shows excellent transmission in the region of 200-1100 nm. Theoretical calculations were carried out to determine the linear optical constants such as extinction coefficient and refractive index. Further the optical nonlinearities of BTSC have been investigated by Z-scan technique with He-Ne laser radiation of wavelength 632.8 nm. Mechanical properties of the grown crystal were studied using Vickers microhardness tester. Second harmonic generation efficiency of the powdered BTSC monohydrate was tested using Nd:YAG laser and it is found to be ˜5.3 times that of potassium dihydrogen orthophosphate.

  8. 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.

  9. Inhibition of xanthine oxidase by thiosemicarbazones, hydrazones and dithiocarbazates derived from hydroxy-substituted benzaldehydes.

    Science.gov (United States)

    Leigh, Maria; Raines, Daniel J; Castillo, Carmen E; Duhme-Klair, Anne K

    2011-06-06

    Nonpurine xanthine oxidoreductase (XOR) inhibitors represent important alternatives to the purine analogue allopurinol, which is still the most widely used drug in the treatment of conditions associated with elevated uric acid levels in the blood. By condensing mono-, di- and trihydroxybenzaldehydes with aromatic thiosemicarbazides, aryl hydrazides and dithiocarbazates, three series of structurally related Schiff bases were synthesised, characterised and tested for XOR inhibitory activity. Hydroxy substitution in the para-position of the benzaldehyde component was found to confer high inhibitory activities. Acyl hydrazones were generally less potent than thiocarbonyl-containing Schiff bases. Within the thiosemicarbazone series, chloro and cyano substituents in the para-position of the thiosemicarbazide unit increased activities further, up to potencies approximately four-times higher than that of the benchmark allopurinol, as measured under the same assay conditions. In order to illustrate the potential of the Schiff bases to bind directly to the molybdenum centre in the active site of the enzyme, a representative example (H₂L) of each inhibitor series was co-ordinated to a cis-dioxomolybdenum(VI) unit, and the resulting complexes, [MoO₂(L)MeOH], were structurally characterised. Subsequent steady-state kinetic investigations, however, indicated mixed-type inhibition, similar to that observed for inhibitors known to bind within the substrate access channel of the enzyme, remote from the Mo centre. Enzyme co-crystallisation studies are thus required to determine the exact binding mode. Finally, the coordination of representative inhibitors to copper(II) gave rise to significantly decreased IC₅₀ values, revealing an additive effect that merits further investigation. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. 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.

  11. 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.

  12. 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.

  13. 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.

    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

  14. The Cytotoxicity of Benzaldehyde Nitrogen Mustard-2-Pyridine Carboxylic Acid Hydrazone Being Involved in Topoisomerase IIα Inhibition

    Directory of Open Access Journals (Sweden)

    Yun Fu

    2014-01-01

    Full Text Available 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 Fe2+ 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 Fe2+ 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.

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

    International Nuclear Information System (INIS)

    Ndolomingo, Matumuene Joe; Meijboom, Reinout

    2017-01-01

    Highlights: • Cu and Au on γ-Al 2 O 3 catalysts were prepared and characterized. • Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide in the absence of any solvent using the prepared catalysts. • The as prepared catalysts exhibited good performance in terms of conversion and selectivity towards benzaldehyde. • The kinetics of the reaction was investigated; k app was proportional to the amount of nano catalyst and oxidant present in the system. • The catalysts was recycled and reused with neither significant loss of activity nor selectivity. - Abstract: Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide (TBHP) in the absence of any solvent using γ-Al 2 O 3 supported copper and gold nanoparticles. Li 2 O 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), N 2 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

  16. Structure and mechanism of benzaldehyde dehydrogenase from Pseudomonas putida ATCC 12633, a member of the Class 3 aldehyde dehydrogenase superfamily.

    Science.gov (United States)

    Zahniser, Megan P D; Prasad, Shreenath; Kneen, Malea M; Kreinbring, Cheryl A; Petsko, Gregory A; Ringe, Dagmar; McLeish, Michael J

    2017-03-01

    Benzaldehyde dehydrogenase from Pseudomonas putida (PpBADH) belongs to the Class 3 aldehyde dehydrogenase (ALDH) family. The Class 3 ALDHs are unusual in that they are generally dimeric (rather than tetrameric), relatively non-specific and utilize both NAD+ and NADP+. To date, X-ray structures of three Class 3 ALDHs have been determined, of which only two have cofactor bound, both in the NAD+ form. Here we report the crystal structure of PpBADH in complex with NADP+ and a thioacyl intermediate adduct. The overall architecture of PpBADH resembles that of most other members of the ALDH superfamily, and the cofactor binding residues are well conserved. Conversely, the pattern of cofactor binding for the rat Class 3 ALDH differs from that of PpBADH and other ALDHs. This has been interpreted in terms of a different mechanism for the rat enzyme. Comparison with the PpBADH structure, as well as multiple sequence alignments, suggest that one of two conserved glutamates, at positions 215 (209 in rat) and 337 (333 in rat), would act as the general base necessary to hydrolyze the thioacyl intermediate. While the latter is the general base in the rat Class 3 ALDH, site-specific mutagenesis indicates that Glu215 is the likely candidate for PpBADH, a result more typical of the Class 1 and 2 ALDH families. Finally, this study shows that hydride transfer is not rate limiting, lending further credence to the suggestion that PpBADH is more similar to the Class 1 and 2 ALDHs than it is to other Class 3 ALDHs. © The Author 2017. Published by Oxford University Press. All rights reserved. For Permissions, please e-mail: journals.permissions@oup.com.

  17. 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%.

  18. A Study on the Condensation Reaction of 4-Amino-3,5-dimethyl-1,2,4-triazole with Benzaldehydes: Structure and Spectroscopic Properties of Some New Stable Hemiaminals

    Directory of Open Access Journals (Sweden)

    Katarzyna Wajda-Hermanowicz

    2015-09-01

    Full Text Available Studies on the stable hemiaminals and Schiff bases formation in the reaction of substituted benzaldehydes with primary 3,5-dimethyl-1,2,4-triazole 4-amine were carried out under neutral conditions. These products were investigated by IR, Raman, MS, 1H- and 13C-NMR spectra as well as by X-ray crystallography. The effect of reaction conditions: temperature, polarity of the solvents utilized, substrate concentration and the ortho and para benzaldehyde substituents on the yield of products was also examined.

  19. Reaction of 11 C-benzoyl chlorides with metalloid reagents: 11 C-labeling of benzyl alcohols, benzaldehydes, and phenyl ketones from [11 C]CO.

    Science.gov (United States)

    Roslin, Sara; Dahl, Kenneth; Nordeman, Patrik

    2018-01-26

    In this article, we describe the carbon-11 ( 11 C, t 1/2  = 20.4 minutes) labeling of benzyl alcohols, benzaldehydes, and ketones using an efficient 2-step synthesis in which 11 C-carbon monoxide is used in an initial palladium-mediated reaction to produce 11 C-benzoyl chloride as a key intermediate. In the second step, the obtained 11 C-benzoyl chloride is further treated with a metalloid reagent to furnish the final 11 C-labeled product. Benzyl alcohols were obtained in moderated to high non-isolated radiochemical yields (RCY, 35%-90%) with lithium aluminum hydride or lithium aluminum deuteride as metalloid reagent. Changing the metalloid reagent to either tributyltin hydride or sodium borohydride, allowed for the reliable syntheses of 11 C-benzaldehydes in RCYs ranging from 58% to 95%. Finally, sodium tetraphenylborate were utilized to obtain 11 C-phenyl ketones in high RCYs (77%-95%). The developed method provides a new and efficient route to 3 different classes of compounds starting from aryl iodides or aryl bromides. Copyright © 2018 John Wiley & Sons, Ltd.

  20. 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...

  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. Hydrotrioxides rather than cyclic tetraoxides (tetraoxolanes) as the primary reaction intermediates in the low-temperature ozonation of aldehydes. The case of benzaldehyde.

    Science.gov (United States)

    Cerkovnik, Janez; Plesnicar, Bozo; Koller, Joze; Tuttle, Tell

    2009-01-02

    We demonstrate in this work by theory and experiment that benzaldehyde hydrotrioxide (PhC(O)OOOH), the intermediate most likely formed in the low-temperature ozonation of benzaldehyde, is too unstable to be detected by NMR (1H, 13C, and 17O) spectroscopy in various organic solvents at temperatures > or = -80 degrees C and that its previous detection must have been erroneous. Several plausible mechanisms for the formation of this polyoxide were explored by using density functional theory. We found that the formation of the hydrotrioxide involves the facile 1,3-dipolar insertion of ozone into the C-H bond (deltaH(double dagger) = 11.1 kcal/mol) in a strongly exothermic process (deltaH(R) = -57.0 kcal/mol). The hydrotrioxide then quickly decomposes in a second concerted, exothermic reaction involving an intramolecular H transfer to form benzoic acid and singlet oxygen (O2(1delta(g))) (deltaH(double dagger) = 5.6 kcal/mol), deltaH(R) = -14.0 kcal/mol). The equilibrium is thus expected to be shifted toward the products; therefore, this intermediate cannot be observed experimentally. Peroxybenzoic acid, still another major reaction product formed in the ozonation reaction, is formed as a result of the surprising instability of the RC(O)O-OOH bond (deltaH(R) = 23.5 kcal/mol), generating HOO* and benzoyloxyl radicals. Both of these radicals can then initiate the chain autoxidation reaction sequence--the abstraction of a H atom from benzaldehyde to form either a benzoyl radical and HOOH or a benzoyl radical and benzoic acid. Because only very small amounts of HOOH were detected in the decomposition mixtures, the recombination of the benzoyl radical with the HOO* radical (deltaH(R) = -80.7 kcal/mol) appears to be the major source of peroxybenzoic acid. A theoretical investigation of the mechanistic possibility of the involvement of still another intermediate, a cyclic tetraoxide (tetraoxolane) formed as a primary product in the 1,3-dipolar cycloaddition of ozone to the

  3. Effects of structures of bidentate Schiff base type bonded-ligands derived from benzaldehyde on the photoluminescence performance of polymer-rare earth complexes.

    Science.gov (United States)

    Gao, Baojiao; Zhang, Liqin; Zhang, Dandan

    2018-02-07

    Two kinds of bidentate Schiff base ligands derived from benzaldehyde, benzaldehyde/m-aminophenol (BAMA) type and benzaldehyde/glutamic acid (BAGL) type ligands, were synchronously synthesized and bonded on the backbone of polysulfone (PSF) through molecular design and by polymer reactions, and two functional polymers, PSF-BAMA and PSF-BAGL, were obtained. Then two series of novel luminescent Schiff base-type polymer-rare earth complexes were prepared via coordination reactions. In this work, the effects of the structures of the bonded ligands on the photoluminescence performance of the complexes were investigated in detail, and for the different photophysical properties of the prepared complexes, relevant theoretical explanations were given. The experimental results show that the bonded ligand BAMA can strongly sensitize the fluorescence emission of Eu(iii) ions, and the binary complex PSF-(BAMA) 3 -Eu(iii) emits strong red fluorescence under UV light. The reason for this lies in the fact that a larger conjugate π-bond system is contained in the structure of BAMA, and so the triplet state of BAMA can be matched with the resonant energy level of the Eu(iii) ion. While the bonded ligand BAGL can effectively sensitize the fluorescence emission of Tb(iii) ions, the binary complex PSF-(BAGL) 3 -Tb(iii) exhibits very strong green fluorescence under UV light. The reason is that a smaller conjugate π-bond system is contained in the structure of BAGL and there is a good energy level matching between the triplet state of BAGL and the resonant energy level of the Tb(iii) ion. The fluorescence intensities of the two ternary complexes, PSF-(BAMA) 3 -Eu(iii)-(Phen) 1 (phenanthroline, Phen) and PSF-(BAGL) 3 -Tb(iii)-(Phen) 1 , are much stronger than that of the corresponding binary complex because Phen as the second ligand has two effects, the effect of synergistic coordination with the first ligand and the effect of replacing the coordinated water around the central ion, and

  4. A DFT study of the catalytic pyrolysis of benzaldehyde on ZnO, γ-Al2O3, and CaO models.

    Science.gov (United States)

    Cui, Li-Ping; Liu, Jiang-Tao; Liu, Shi-Zhong; Wang, Ming-Fei; Gao, Zhi-Hua; Zuo, Zhi-Jun; Huang, Wei

    2018-02-21

    The catalytic pyrolysis pathways of carbonyl compounds in coal were systematically studied using density functional theory (DFT), with benzaldehyde (C 6 H 5 CHO) employed as a coal-based model compound and ZnO, γ-Al 2 O 3 , and CaO as catalysts. The results show that the products of both pyrolysis and catalytic pyrolysis are C 6 H 6 and CO. However, the presence of any of the catalysts changes the reaction pathway and reduces the energy barrier, indicating that these catalysts promote C 6 H 5 CHO decomposition. Graphical abstract The presence of catalysts changes the reaction pathway and the energy barrier decreases in the order Ea (no catalyst)> Ea (CaO)> Ea (γ-Al 2 O 3 )> Ea (ZnO), indicating that these catalysts promote C 6 H 5 CHO decomposition.

  5. (2,3,7,8,12,13,17,18-Octa-ethyl-porphyrinato-κ(4)N)cobalt(II)-2-nitro-benzaldehyde (1/2).

    Science.gov (United States)

    Mansour, Anissa; Daran, Jean-Claude; Nasri, Habib

    2012-09-01

    The asymmetric unit of the title compound, [Co(C(36)H(44)N(4))]·2C(7)H(5)NO(3), is composed of one half of the complex, arranged about an inversion center, and a complete 2-nitro-benzaldehyde (NBA) mol-ecule. The structure consists of columns that contain inter-leaved mol-ecules of NBA and [Co(II)(OEP)] (OEP is 2,3,7,8,12,13,17,18-octa-ethyl-porphyrin), which are stacked along the a axis. The Co(II) atom is involved in a π inter-action with the ring of the NBA mol-ecule with a centroid-metal distance of 3.508 (6) Å. There is an intra-molecular C-H⋯O hydrogen bond in the NBA mol-ecule.

  6. Gas chromatography-flame ionization determination of benzaldehyde in non-steroidal anti-inflammatory drug injectable formulations using new ultrasound-assisted dispersive liquid-liquid micro extraction

    International Nuclear Information System (INIS)

    Mashayekhi, H.A.; Pourshamsian, K.

    2012-01-01

    Summary: In this study, simple and efficient ultrasound-assisted dispersive liquid-liquid micro extraction combined with gas chromatography (GC) was developed for the preconcentration and determination of benzaldehyde in injectable formulations of the non-steroidal anti-inflammatory drugs, diclofenac, Vitamin B-complex and Voltaren injection solutions. Fourteen microliters of toluene was injected slowly into 10 mL home-designed centrifuge glass vial containing an aqueous sample without salt addition that was located inside the ultrasonic water bath. The formed emulsion was centrifuged and 2 macro L of separated toluene was injected into a gas chromatographic system equipped with a flame ionization detector (GC-FID) for analysis. Several factors influencing the extraction efficiency as the nature and volume of organic solvent, extraction temperature, ionic strength and centrifugation time were investigated and optimized. Using optimum extraction conditions a detection limit of 0.3 macro g L/sup -1/ and a good linearity in a calibration range of 2.0-1000 macro g L/sup -1/ were achieved for analyte. This proposed method was successfully applied to the analysis of benzaldehyde in three injection formulations and relative standard deviation (RSD) of analysis (n=3), before spiking with standard benzaldehyde were 3.3, 2.0 and 1.3% for Na-diclofenac, vitamin B-complex and voltaren, respectively and after spiking of standard benzaldehyde (0.3 mg L/sup -1/), the RSD were 6.5, 3.6 and 2.8% for Na-diclofenac, vitamin B-complex and voltaren, respectively. (author)

  7. Extractive spectrophotometric determination of copper(II in water and alloy samples with 3-methoxy-4-hydroxy benzaldehyde-4-bromophenyl hydrazone (3,4-MHBBPH

    Directory of Open Access Journals (Sweden)

    D. REKHA

    2007-03-01

    Full Text Available A facile, sensitive and selective extractive spectrophotometricmethod was developed for the determination of copper(II in various water and alloy samples using a newly synthesized reagent, 3-methoxy-4-hydroxy benzaldehyde 4-bromophenyl hydrazone (3,4-MHBBPH. Copper(II forms a orange colored complex with (3,4-MHBBPH in acetate buffermedium (pH 4 which increases the sensitivity and the complexwas extracted into chloroform. Under optimum conditions, the maximum absorption of the chloroform extract was measured at 462 nm. The Beer law was obeyed in the range of 0.20 to 4.0 mg ml-1 of copper. The molar absorptivity and the Sandell's sensitivity of the complex were 2.0520 ´ 104 mol-1 cm-1 and 0.2540 mg cm-2, respectively. The detection limit was found to be 0.0270 mg mL-1. Adetailed study of various interfering ions made the method more sensitive. The method was successfully applied for the determination of Cu(II in water and alloy samples. The performance of the present method was evaluated in terms of Student 't' test and Variance ratio 'f ' test, which indicate the significance of the present method over reported methods.

  8. Selective liquid phase oxidation of benzyl alcohol to benzaldehyde by tert-butyl hydroperoxide over γ-Al{sub 2}O{sub 3} supported copper and gold nanoparticles

    Energy Technology Data Exchange (ETDEWEB)

    Ndolomingo, Matumuene Joe; Meijboom, Reinout, E-mail: rmeijboom@uj.ac.za

    2017-03-15

    Highlights: • Cu and Au on γ-Al{sub 2}O{sub 3} catalysts were prepared and characterized. • Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide in the absence of any solvent using the prepared catalysts. • The as prepared catalysts exhibited good performance in terms of conversion and selectivity towards benzaldehyde. • The kinetics of the reaction was investigated; k{sub app} was proportional to the amount of nano catalyst and oxidant present in the system. • The catalysts was recycled and reused with neither significant loss of activity nor selectivity. - Abstract: Benzyl alcohol oxidation to benzaldehyde was performed by tert-butyl hydroperoxide (TBHP) in the absence of any solvent using γ-Al{sub 2}O{sub 3} supported copper and gold nanoparticles. Li{sub 2}O 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), N{sub 2} 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

  9. Synthesis, characterization, and thermal stability of novel poly(azomethine-urethane)s and polyphenol derivatives derived from 2,4-dihydroxy benzaldehyde and toluene-2,4-diisocyanate

    Energy Technology Data Exchange (ETDEWEB)

    Kaya, Ismet, E-mail: kayaismet@hotmail.com [Canakkale Onsekiz Mart University, Faculty of Sciences and Arts, Department of Chemistry, 17020, Canakkale (Turkey); Avc Latin-Small-Letter-Dotless-I , Ali [Celal Bayar University, Faculty of Sciences and Arts, Department of Chemistry, 45040, Manisa (Turkey)

    2012-03-15

    Graphical abstract: Black-Right-Pointing-Triangle Synthesis, characterization, and thermal stability of novel poly(azomethine-urethane)s and polyphenol derivatives derived from 2,4-dihydroxy benzaldehyde and toluene-2,4-diisocyanate. Highlights: Black-Right-Pointing-Pointer New pol(azomethine-urethane)s were synthesized. Black-Right-Pointing-Pointer PAMUs were converted to their polyphenol species by oxidative polymerization reaction with NaOCl. Black-Right-Pointing-Pointer The synthesized compounds were characterized by solubility tests, TGA and DSC. Black-Right-Pointing-Pointer T{sub g} values of PAMUs were between 137 and 178 Degree-Sign C and thermal stabilities of them were very good. Black-Right-Pointing-Pointer Obtained compounds can be promising candidates for aerospace applications. - Abstract: Up to date, only a few kinds of poly(azomethine-urethane)s (PAMUs) were synthesized and studied with thermal degradation steps. However, polyphenol based PAMUs including azomethine linkages have not been investigated yet. The polyurethanes were prepared by condensation reaction of 2,4-dihydroxybenzaldehyde (2,4-DHBA) with toluene-2,4-diisocyanate (TDI) under argon atmosphere. Synthesized polyurethane was converted to its poly(azomethine urethane) species (TP-2AP, TP-3AP, and TP-4AP) by graft copolymerization reactions with amino phenols (2-amino phenol, 3-amino phenol, and 4-amino phenol). Obtained poly(azomethine urethane)s were converted to their polyphenol species (P-TP-2AP, P-TP-3AP, and P-TP-4AP) by oxidative polymerization reaction (OP) using NaOCl as the oxidant. The structures of the obtained compounds were confirmed by FT-IR, UV-vis, {sup 1}H NMR, and {sup 13}C NMR techniques. The molecular weight distribution parameters of the synthesized compounds were determined by the size exclusion chromatography (SEC). The synthesized compounds were also characterized by solubility tests, TG-DTA, and DSC. Fluorescence measurements were carried out in various

  10. 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.

  11. Enhancement of reaction rates for catalytic benzaldehyde ...

    Indian Academy of Sciences (India)

    High-pressure carbon dioxide; high-temperature liquid water; carbonic acid. 1. Introduction. We have succeeded to ... Also, cost-consuming troublesome proce- dures are needed for neutralization of acid, and salts .... high hydrogen solubility to organic phase may cause the enhancement of the hydrogenation yield by ...

  12. Overtone spectroscopy of some benzaldehyde derivatives

    Indian Academy of Sciences (India)

    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 ...

  13. Overtone spectroscopy of some benzaldehyde derivatives

    Indian Academy of Sciences (India)

    For the case of ortho- and meta-disubstitutions and when the two ... and a weak one at 3050 cm-½ are seen. For o-nitrobenzaldehyde a strong peak is observed at 3104 cm-½ accompanied with two relatively weak peaks. Meta .... for alkyl and aryl CH bonds estimated using the relation De = ωѕe/4ωeme are also listed.

  14. Oxidation of styrene to benzaldehyde/benzoic acid

    Indian Academy of Sciences (India)

    spectroscopy and powder X-ray crystallography. Keywords. Heptamolybdate type polyoxometalate cluster anion; transition metal coordination complexes; oxidation of styrene; hydrogen peroxide as an oxidant; catalysis. 1. Introduction. Over the last ...

  15. Heterocyclyl linked anilines and benzaldehydes as precursors for ...

    Indian Academy of Sciences (India)

    ... 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).

  16. Synthesis of Chalcone and Flavanone Compound Using Raw Material of Acetophenone and Benzaldehyde Derivative

    Directory of Open Access Journals (Sweden)

    Ismiyarto Ismiyarto

    2010-06-01

    Full Text Available Synthesis of flavanoid compounds of chalcone and flavanone groups have been conducted. Flavanoid Is one of the group natural products which is mostly found in plants and have been proved to have physiological activity as drug. In this research, chalcone proup compounds that being synthesized are: chalcone, 3,4-dimethoxychalcone, 2'-hidroxy-3,4-dimethoxychalcone where as compound of flavanone group that being synthesized is 3',4'-dimethoxyflavanone. The synthesis of chalcone group are carried out based on Claisen-Schmidt reaction by using raw material of aromatic aldehydes and aromatic ketones. The synthesis in carried out by stirring at the room temperature using alkali solution as catalyst and ethanol as solvent. The synthesis of 3',4'-dimethoxyflanone is made based on the nucleophilic 1,4 addition of the unsaturated α,β ketone. The synthesis is made by refluxing 2'-hydroxy-3,4-dimethoxychalcone in alkali condition for 12 hours. The identification of flavanoid compound is carried out by using spectroscopic IR, GC-MS and 1H-NMR methods. The result of each synthesis chalcone group are follows: chalcone as yellowish solid with m.p= 50 °C and the yield is 83.39%; 3,4-dimethoxychalcone as yellow solid with m.p= 57°C and the yield is 76.00% ; 2'-hydroxy-3,4-dimethoxychalcone as orange solid with m.p= 90 °C and the yield is 74.29%, for 3',4'-dimethoxyflavanone as pale yellow solid with m.p= 80 °C and the yield is 72.00%.

  17. 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.

  18. Rh(III)-catalyzed olefination of N-sulfonyl imines: synthesis of ortho-olefinated benzaldehydes.

    Science.gov (United States)

    Zhang, Tao; Wu, Lamei; Li, Xingwei

    2013-12-20

    Rh(III)-catalyzed olefination of N-sulfonyl imines using acrylates and styrenes has been achieved for the synthesis of ortho-olefinated benaldehydes. This reaction proceeds via a chelation assisted C-H olefination/in situ hydrolysis process.

  19. 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.

  20. Evaluation of benzaldehyde derivatives from Morinda officinalis as anti-mite agents with dual function as acaricide and mite indicator

    Science.gov (United States)

    Yang, Ji-Yeon; Kim, Min-Gi; Park, Jun-Hwan; Hong, Seong-Tshool; Lee, Hoi-Seon

    2014-01-01

    Severe fever with thrombocytopenia syndrome (SFTS) is an emerging infectious disease caused by SFTS virus with 12–30% fatality rate. Despite severity of the disease, any medication or treatment for SFTS has not developed yet. One approach to prevent SFTS spreading is to control the arthropod vector carrying SFTS virus. We report that 2–methylbenzaldehyde analogues from M. officinalis have a dual function as acaricide against Dermatophagoides spp. and Haemaphysalis longicornis and indicator (color change) against Dermatophagoides spp. Based on the LD50 values, 2,4,5–trimethylbenzaldehyde (0.21, 0.19, and 0.68 μg/cm3) had the highest fumigant activity against D. farinae, D. pteronyssinus, and H. longicornis, followed by 2,3–dimethylbenzaldehyde (0.46, 0.44, and 0.79 μg/cm3), 2,4–dimethylbenzaldehyde (0.66, 0.59, and 0.95 μg/cm3), 2,5–dimethylbenzaldehyde (0.65, 0.68, and 0.88 μg/cm3), 2–methylbenzaldehyde (0.95, 0.87, and 1.28 μg/cm3), 3–methylbenzaldehyde (0.99, 0.93, and 1.38 μg/cm3), 4–methylbenzaldehyde (1.17, 1.15, and 3.67 μg/cm3), and M. officinalis oil (7.05, 7.00, and 19.70 μg/cm3). Furthermore, color alteration of Dermatophagoides spp. was shown to be induced, from colorless to dark brown, by the treatment of 2,3–dihydroxybenzaldehyde. These finding indicated that 2–methylbenzaldehyde analogues could be developed as functional agent associated with the arthropod vector of SFTS virus and allergen. PMID:25434408

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

    International Nuclear Information System (INIS)

    Wadsak, Wolfgang; Wirl-Sagadin, Barbara; Mitterhauser, Markus; Mien, Leonhard-Key; Ettlinger, Dagmar E.; Keppler, Bernhard K.; Dudczak, Robert; Kletter, Kurt

    2006-01-01

    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 [ 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 [ 18 F]fluorinated synthons for PET

  2. 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.

  3. The influence of operating conditions on the efficiency of vapor phase hydrogen peroxide in the degradation of 4-(dimethylamino)benzaldehyde

    Czech Academy of Sciences Publication Activity Database

    Švrček, J.; Marhoul, A.; Kačer, P.; Kuzma, Marek; Pánek, L.; Červený, L.

    2010-01-01

    Roč. 81, č. 5 (2010), s. 617-625 ISSN 0045-6535 R&D Projects: GA MPO FT-TA4/071 Institutional research plan: CEZ:AV0Z50200510 Keywords : Vapor phase hydrogen peroxide * Degradation * Chemical contaminants Subject RIV: EE - Microbiology, Virology Impact factor: 3.155, year: 2010

  4. 1,3,4-Thiadiazole derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones cause death in Trypanosoma cruzi through oxidative stress.

    Science.gov (United States)

    Martins, Solange C; Lazarin-Bidóia, Danielle; Desoti, Vânia C; Falzirolli, Hugo; da Silva, Cleuza C; Ueda-Nakamura, Tania; Silva, Sueli de O; Nakamura, Celso V

    2016-12-01

    This work evaluated the in vitro and in vivo activity of TDZ 2 on Trypanosoma cruzi amastigotes and determined the possible mechanism of action of this compound on T. cruzi death. TDZ 2 inhibited T. cruzi proliferation in vitro and had low haemolytic potential. It also induced morphological and ultrastructural alterations. We observed a reduction of cell volume, the depolarization of the mitochondrial membrane, an increase in ROS production, lipoperoxidation of the cell membrane, lipid bodies formation and production of nitric oxide, a decrease in reduced thiols levels and, presence of autophagic vacuoles. The in vivo study found a reduction of parasitemia in animals treated with TDZ 2 alone or combined with benznidazole. Altogether, the alterations induced by TDZ 2 point to an oxidative stress condition that lead to T. cruzi cell death. Copyright © 2016 Institut Pasteur. Published by Elsevier Masson SAS. All rights reserved.

  5. 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.

  6. Sequential meta-C-H olefination of synthetically versatile benzyl silanes: effective synthesis of meta-olefinated toluene, benzaldehyde and benzyl alcohols.

    Science.gov (United States)

    Patra, Tuhin; Watile, Rahul; Agasti, Soumitra; Naveen, Togati; Maiti, Debabrata

    2016-02-04

    Tremendous progress has been made towards ortho-selective C-H functionalization in the last three decades. However, the activation of distal C-H bonds and their functionalization has remained fairly underdeveloped. Herein, we report sequential meta-C-H functionalization by performing selective mono-olefination and bis-olefination with late stage modification of the C-Si as well as Si-O bonds. Temporary silyl connection was found to be advantageous due to its easy installation, easy removal and wide synthetic diversification.

  7. Synthesis of benzaldehyde-functionalized glycans: a novel approach towards glyco-SAMs as a tool for surface plasmon resonance studies.

    Science.gov (United States)

    Kopitzki, Sebastian; Jensen, Knud J; Thiem, Joachim

    2010-06-18

    In recent years the interest in tools for investigating carbohydrate-protein (CPI) and carbohydrate-carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self-assembled monolayers (SAM) of carbohydrate derivatives, which can mimic the glycocalyx. In contrast to the SPR imaging methods used previously to analyze CPI and CCI, the novel approach reported herein allows a facile and rapid synthesis of linker spacers and carbohydrate derivatives and enhances the binding event by controlling the amount and orientation of ligand. For immobilization on biorepulsive amino-functionalized SPR chips by reductive amination, diverse aldehyde-functionalized glycan structures (glucose, galactose, mannose, glucosamine, cellobiose, lactose, and lactosamine) have been synthesized in several facile steps that include olefin metathesis. Effective immobilization and the first binding studies are presented for the lectin concanavalin A.

  8. Environmentally friendly synthesis of CeO2 nanoparticles for the catalytic oxidation of benzyl alcohol to benzaldehyde and selective detection of nitrite

    Science.gov (United States)

    Tamizhdurai, P.; Sakthinathan, Subramanian; Chen, Shen-Ming; Shanthi, K.; Sivasanker, S.; Sangeetha, P.

    2017-04-01

    Cerium oxide nanoparticles (CeO2 NPs) are favorable in nanotechnology based on some remarkable properties. In this study, the crystalline CeO2 NPs are successfully prepared by an efficient microwave combustion (MCM) and conventional route sol-gel (CRSGM) methods. The structural morphology of the as-prepared CeO2 NPs was investigated by various spectroscopic and analytical techniques. Moreover, the XRD pattern confirmed the formation of CeO2 NPs as a face centered cubic structure. The magnetometer studies indicated the low saturation magnetization (23.96 emu/g) of CeO2 NPs for weak paramagnetic and high saturation magnetization (32.13 emu/g) of CeO2 NPs for super paramagnetic. After that, the oxidation effect of benzyl alcohol was investigated which reveals good conversion and selectivity. Besides, the CeO2 NPs modified glassy carbon electrode (GCE) used for the detection of nitrite with linear concentration range (0.02-1200 μM), low limit of detection (0.21 μM) and higher sensitivity (1.7238 μAμM-1 cm-2). However, the CeO2 NPs modified electrode has the fast response, high sensitivity and good selectivity. In addition, the fabricated electrode is applied for the determination of nitrite in various water samples. Eventually, the CeO2 NPs can be regarded as an effective way to enhance the catalytic activity towards the benzyl alcohol and nitrite.

  9. Environmentally friendly synthesis of CeO2 nanoparticles for the catalytic oxidation of benzyl alcohol to benzaldehyde and selective detection of nitrite.

    Science.gov (United States)

    Tamizhdurai, P; Sakthinathan, Subramanian; Chen, Shen-Ming; Shanthi, K; Sivasanker, S; Sangeetha, P

    2017-04-13

    Cerium oxide nanoparticles (CeO 2 NPs) are favorable in nanotechnology based on some remarkable properties. In this study, the crystalline CeO 2 NPs are successfully prepared by an efficient microwave combustion (MCM) and conventional route sol-gel (CRSGM) methods. The structural morphology of the as-prepared CeO 2 NPs was investigated by various spectroscopic and analytical techniques. Moreover, the XRD pattern confirmed the formation of CeO 2 NPs as a face centered cubic structure. The magnetometer studies indicated the low saturation magnetization (23.96 emu/g) of CeO 2 NPs for weak paramagnetic and high saturation magnetization (32.13 emu/g) of CeO 2 NPs for super paramagnetic. After that, the oxidation effect of benzyl alcohol was investigated which reveals good conversion and selectivity. Besides, the CeO 2 NPs modified glassy carbon electrode (GCE) used for the detection of nitrite with linear concentration range (0.02-1200 μM), low limit of detection (0.21 μM) and higher sensitivity (1.7238 μAμM -1 cm -2 ). However, the CeO 2 NPs modified electrode has the fast response, high sensitivity and good selectivity. In addition, the fabricated electrode is applied for the determination of nitrite in various water samples. Eventually, the CeO 2 NPs can be regarded as an effective way to enhance the catalytic activity towards the benzyl alcohol and nitrite.

  10. 75 FR 763 - Dibenzylidene Sorbitol; Exemption from the Requirement of a Tolerance

    Science.gov (United States)

    2010-01-06

    ... minimum of 96% DBS. DBS is not expected to pose a hazard when used for its proposed use pattern. A skin... benzaldehyde in the body. Sorbitol is a natural constituent and is considered non-carcinogenic and benzaldehyde..., DBS has reported uses in personal care products, such as antiperspirants, shampoos, conditioners, and...

  11. Untitled

    Indian Academy of Sciences (India)

    yield of 43% p-tolylhydrazine, based on chloramine. The benzaldehyde derivative was prepared by refluxing the neutralized reaction mixture (using HCl) and benzaldehyde for 24 hrs, and subsequently cooling it in ice and salt mixture. When a methanolic solution (300 ml) containing 10.5 ml (126 mmol) of pyrrolidine.

  12. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    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.

  13. Biological evaluation of 32 different essential oils against ...

    African Journals Online (AJOL)

    Also, 0.2% (v/v) levels of cinnamon oil, benzaldehyde and cinnamaldehyde completely killed ACC cells artificially contaminating watermelon seeds. This study suggests that cinnamon oil and its bioactive components, benzaldehyde and cinnamaldehyde, have potential for application as natural agents for the prevention ...

  14. Modified calcium oxide as stable solid base catalyst for Aldol ...

    Indian Academy of Sciences (India)

    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 ...

  15. Untitled

    Indian Academy of Sciences (India)

    Abstract. The dipole moments of a number of substituted benzaldehydes are measured in benzene solution. The angle which the dipole axis of the ~CHO group makes with the axis of rotation of the group is determined. The observed moments of the ortho-substituted benzaldehydes are compared with the moments ...

  16. 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...... substances [FL-no: 06.104 and 09.570] and new information to support the re-allocation of the structural class for the candidate substance piperonyl alcohol [FL-no: 02.205] has been submitted. The 41 flavouring substances in Flavouring Group Evaluation 20 were evaluated using the Procedure in Commission...... Regulation (EC) No 1565/2000. None of the substances were considered to have genotoxic potential. The substances were evaluated through a stepwise approach (the Procedure) that integrates information on structure-activity relationships, intake from current uses, toxicological threshold of concern...

  17. Cyanogenic glucoside patterns in sweet and bitter almonds

    DEFF Research Database (Denmark)

    Sánchez Pérez, Raquel; Møller, Birger Lindberg; Olsen, Carl Erik

    2009-01-01

    When an almond (Prunus dulcis (Mill.) D. A. Webb) kernel containing cyanogenic glucosides (prunasin or amygdalin) is disintegrated, the glucosides will typically be hydrolyzed by amygdalin hydrolase, prunasin hydrolase, and mandelonitrile lyase with concomitant release of glucose, benzaldehyde...

  18. 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.

  19. 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)

  20. 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)

  1. 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

  2. Microwave Assisted Synthesis and Evaluation of N-Cinnamoyl Aryl Hydrazones for Cytotoxic and Antioxidant Activities

    OpenAIRE

    T. Sarala Devi; G. Rajitha

    2016-01-01

    A series of N-cinnamoyl aryl hydrazones 2a-2i were synthesized in good yields by microwave irradiation technique . The title compounds were formed by nucleophilic condensation of various N1- substituted benzylidene-2-cyano aceto hydrazides with N,N-dimethyl amino benzaldehyde. The intermediate N1- substituted benzylidene-2-cyano aceto hydrazide was obtained by condensing various substituted benzaldehydes with cyanoacetohydrazide. The structures of the compounds were characterized by ...

  3. N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes

    Directory of Open Access Journals (Sweden)

    Guang-Fen Du

    2016-03-01

    Full Text Available A N-heterocyclic carbene (NHC catalyzed addition reaction of 3-trimethylsilyl propiolate with aldehydes has been developed. Under the catalysis of 2 mol% NHCs, benzaldehyde, furfural, β-naphthaldehyde, meta- and para-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford β-acylated MBH adducts in good yield with excellent stereoselectivity. While ortho-substituted benzaldehydes coupled with 3-trimethylsilyl propiolate to give alkynylation products as the sole products under the same reaction conditions.

  4. Technical communications

    International Nuclear Information System (INIS)

    Krueger, D.A.

    1987-01-01

    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 ( 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 14 C activity as expected for a petrochemical material. Implications for quality control of bitter almond oil are discussed

  5. Probing the molecular forces involved in binding of selected volatile flavour compounds to salt-extracted pea proteins.

    Science.gov (United States)

    Wang, Kun; Arntfield, Susan D

    2016-11-15

    Molecular interactions between heterologous classes of flavour compounds with salt-extracted pea protein isolates (PPIs) were determined using various bond disrupting agents followed by GC/MS analysis. Flavour bound by proteins decreased in the order: dibutyl disulfide>octanal>hexyl acetate>2-octanone=benzaldehyde. Benzaldehyde, 2-octanone and hexyl acetate interacted non-covalently with PPIs, whereas octanal bound PPIs via covalent and non-covalent forces. Dibutyl disulfide reacted with PPIs covalently, as its retention was not diminished by urea and guanidine hydrochloride. Using propylene glycol, H-bonding and ionic interactions were implicated for hexyl acetate, benzaldehyde, and 2-octanone. A protein-destabilising salt (Cl3CCOONa) reduced bindings for 2-octanone, hexyl acetate, and benzaldehyde; however, retention for octanal and dibutyl disulfide increased. Conversely, a protein-stabilising salt (Na2SO4) enhanced retention for benzaldehyde, 2-octanone, hexyl acetate and octanal. Formation of a volatile flavour by-product, 1-butanethiol, from dibutyl disulfide when PPIs were treated with dithiothreitol indicated occurrence of sulfhydryl-disulfide interchange reactions. Copyright © 2016 Elsevier Ltd. All rights reserved.

  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. Divergent reactivity of homologue ortho-allenylbenzaldehydes controlled by the tether length: chromone versus chromene formation.

    Science.gov (United States)

    Alcaide, Benito; Almendros, Pedro; Fernández, Israel; Martínez del Campo, Teresa; Naranjo, Teresa

    2015-01-19

    The divergent behavior of two homologue allenals, namely, 2-(buta-2,3-dienyloxy)- and 2-(propa-1,2-dienyloxy)benzaldehydes, as cyclization substrates is described. 2-(Buta-2,3-dienyloxy)benzaldehydes suffers a formal allenic carbocyclization reaction to afford chromenes, whereas 2-(propa-1,2-dienyloxy)benzaldehydes react to yield chromones. The formation of chromenes is strictly a formal hydroarylation process divided into two parts, namely, allenic Claisen-type rearrangement and oxycyclization. An unknown N-heterocyclic carbene (NHC)-catalyzed allenic hydroacylation reaction must be invoked to account for the preparation of chromones. ortho-Allenylbenzaldehydes bearing either electron-donating substituents or electron-withdrawing substituents worked well to afford both the hydroarylation and hydroacylation products. This unexpected difference in reactivity can be rationalized by means of density functional theory calculations. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Synthesis, spectral investigation (/sup 1/H, /sup 13/C) of new (N, O and S based) schiff bases and evaluation of their antimicrobial activities

    International Nuclear Information System (INIS)

    Khosa, M.K.; Nisar, M.; Jamal, M.A.; Yousaf, M.; Chatha, S.A.S.; Zia, K.M.

    2011-01-01

    Three new series of biologically active amino substituted Schiff bases (1-12) with general formula, R/sub 1/N=CHR/sub 2/ (R/sub 1/ 2-amino-benzthiazole, 4-amino-salicylic acid and 4-aminophenol; R/sub 2/ benzaldehyde, 2-chloro-benzaldehyde, 4-chloro-benzaldehyde, salicylaldehyde and vanillin) were synthesized by the reaction of three different amino substituted compounds and substituted aldehydes in ethanol. The synthesized compounds were characterized by different physico-chemical techniques like, melting point, elemental analysis, multinuclear NMR (/sup 1/H, /sup 13/C). The compounds were subjected for bioassay screening and showed promising antibacterial and antifungal activities using Amoxicillin and Ciprofloxacin as standard drugs. (author)

  9. Nitroaromatics are substrates for the TOL plasmid upper-pathway enzymes

    Energy Technology Data Exchange (ETDEWEB)

    Delgado, A.; Abril, M.A.; Ramos, J.L. (Consejo Superior de Investigaciones Cientificas, Granada (Spain)); Wubbolts, M.G. (Univ. of Groningen (Netherlands))

    1992-01-01

    Expression of the xylMA genes encoding for toluene monoxygenase from the lactose promoter in a broad-host-range plasmid allows the oxidation of toluene and m- and p-nitrotoluene to their corresponding benzyl alcohols and benzaldehydes in Pseudomonas putida and Escherichia coli. Benzyl alcohols accumulate until reaching a concentration of about 80 {mu}M, while benzaldehydes accumulate steadily with time for at least 24 h. TOL-encoded benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase recognize m- and p-nitro-substituted compounds as substrates. In contrast, the XylR protein, which regulates the TOL plasmid-encoded upper-pathway operon, does not recognize nitro-substituted toluenes as effectors.

  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. The influence of additives in the stoichiometry of hybrid lead halide perovskites

    Science.gov (United States)

    Burgués-Ceballos, Ignasi; Savva, Achilleas; Georgiou, Efthymios; Kapnisis, Konstantinos; Papagiorgis, Paris; Mousikou, Androniki; Itskos, Grigorios; Othonos, Andreas; Choulis, Stelios A.

    2017-11-01

    We investigate the employment of carefully selected solvent additives in the processing of a commercial perovskite precursor ink and analyze their impact on the performance of organometal trihalide perovskite (CH3NH3PbI3-xClx) photovoltaic devices. We provide evidence that the use of benzaldehyde can be used as an effective method to preserve the stoichiometry of the perovskite precursors in solution. Benzaldehyde based additive engineering shows to improve perovskite solid state film morphology and device performance of CH3NH3PbI3-xClx based solar cells.

  12. Download this PDF file

    African Journals Online (AJOL)

    In the first step, a solution of p-dimethylamine benzaldehyde (1 mmol) in ... CaCl,. In the second step, the required semicarbazone was prepared by the following method by adding semicarbazone ... The conductivity measurements were carried out using a Toshniwal Conductivity Bridge (Type. CL 01/01) and a dip type cell ...

  13. Browse Title Index

    African Journals Online (AJOL)

    Items 651 - 700 of 1255 ... Vol 9, No 1 (2003), Identification of Trimer and Dimer of 4-hydroxy-3-methoxy benzaldehyde in crystal structure of Vanillin, Abstract PDF ... Vol 20, No 2 (2014), Influence of electromagnetic waves produced by an amplitude modulation radio antenna on the electric power delivered by a silicon solar ...

  14. Author Details

    African Journals Online (AJOL)

    Akinchan, Narayan T. Vol 9, No 1 (2003) - Articles Identification of Trimer and Dimer of 4-hydroxy-3-methoxy benzaldehyde in crystal structure of Vanillin Abstract PDF. ISSN: 1118-0579. AJOL African Journals Online. HOW TO USE AJOL... for Researchers · for Librarians · for Authors · FAQ's · More about AJOL · AJOL's ...

  15. Highly efficient solvent-free synthesis of pyranopyrazoles by a ...

    Indian Academy of Sciences (India)

    ... 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, ...

  16. 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…

  17. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Keywords. -aryl--mercaptoketones; anhydrous potassium carbonate; amberlyst-15; chalcones; thia-Michael addition. Abstract. Two expedient one-pot methods have been developed for synthesis of -aryl--mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve ...

  18. "De Novo"-synthesis of chlorinated biphenyls, dibenzofurans and dibenzo-p-dioxins in the fly ash catalyzed reaction of toluene with hydrochloric acid

    NARCIS (Netherlands)

    Leer, E.W.B. de; Lexmond, R.J.; Zeeuw, M.A. de

    1989-01-01

    Toluene is converted into benzaldehyde and halogenated aromatic oxidation products in an air atmosphere at 425 °C with fly ash from a municipal waste incineration plant as the catalyst. Several halogenated products such as chlorinated and brominated benzenes, biphenyls and traces of PCDDs/PCDFs

  19. NITROAROMATICS ARE SUBSTRATES FOR THE TOL PLASMID UPPER-PATHWAY ENZYMES

    NARCIS (Netherlands)

    DELGADO, A; Wubbolts, Marcel; ABRIL, MA; RAMOS, JL

    Expression of the xylMA genes encoding for toluene monooxygenase from the lactose promoter in a broad-host-range plasmid allows the oxidation of toluene and m- and p-nitrotoluene to their corresponding benzyl alcohols and benzaldehydes in Pseudomonas putida and Escherichia coli. Benzyl alcohols

  20. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Polyoxometalate coordinated transition metal complexes as catalysts: Oxidation of styrene to benzaldehyde/benzoic acid · Srinivasa Rao Amanchi Anjali Patel Samar ... pp 1647-1653 Regular Articles. Two new twisted helical nickel(II) and cobalt(III) octahedral monomer complexes: Synthesis and structural characterization.

  1. Fulltext PDF

    Indian Academy of Sciences (India)

    124, No. 5, September 2012, pp. 1063–1069. c Indian Academy of Sciences. Heterocyclyl linked anilines and benzaldehydes as precursors for biologically significant new chemical entities. RAMAN K VERMAa,∗, VIJAY KUMARa, PRITHWISH GHOSHa and LALIT K WADHWAb. aSynthetic Organic and Medicinal Chemistry ...

  2. 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)

  3. Preparation and characterization of monosubstituted porphyrins ...

    Indian Academy of Sciences (India)

    Administrator

    2. Experimental. 2.1 Materials. Terephthalaldehydic acid (TPHA), benzaldehyde, 3-amino- propyltriethoxysilane (APTES), pyrrole, N-hydroxysuccin- ..... confirm the reaction between ethoxysilane groups of com- pound (1) and the free silanols on the surface of the sup- ports. Similar trends are observed in the case of the ...

  4. Substituent effect of phenolic aldehyde inhibition on alcoholic fermentation by Saccharomyces cerevisiae

    Science.gov (United States)

    Rui Xie; Maobing Tu; Thomas Elder

    2016-01-01

    Phenolic compounds significantly inhibit microbial fermentation of biomass hydrolysates. To understand thequantitative structure-inhibition relationship of phenolic aldehydes on alcoholic fermentation, the effect of 11 differentsubstituted benzaldehydes on the final ethanol yield was examined. The results showed that the degree of phenolic...

  5. A simple model for chiral amplification in the aminoalcohol-catalyzed reaction of aldehydes with dialkylzinc

    Directory of Open Access Journals (Sweden)

    IVAN GUTMAN

    1999-08-01

    Full Text Available A simple explanation is offered for the recently discovered chiral amplification in the alkylation reaction of benzaldehyde by means of dialkylzinc, catalyzed by (dimethylaminoisoborneol. The model presentd is similar to, yet somewhat simpler than, the model put forward by Noyori et al.

  6. and 8-Membered Oxygen-containing Benzo-fused Rings using ...

    African Journals Online (AJOL)

    NJD

    published methods for the generation of these types of benzo- fused structural units. One of these potential ... pounds 1–6, of different ring sizes, from the same precursor 15.14. This compound has been extensively used in our ... benzaldehyde, probably formed by the deallylation of the benzyl alcohol followed by oxidation.

  7. A new Mannich base and its transition metal (II) complexes ...

    Indian Academy of Sciences (India)

    Unknown

    some metal complexes of this type of Mannich base and investigate its bonding characteristics. We herein report a new Mannich base, N-(1-morpholinoben- zyl) semicarbazide formed by the three-component condensation, containing active hydrogen on nitro- gen (morpholine), benzaldehyde and semicarbazide.

  8. Use of Competition Kinetics with Fast Reactions of Grignard Reagents

    DEFF Research Database (Denmark)

    Holm, Torkil

    2000-01-01

    or effects of polar substituents with isotopically or otherwise substituted benzophenones. A recently reported a-deuterium secondary KIE for the reaction of benzaldehyde with allylmagnesium bromide was observed at -78 °C , but was absent at room temperature. It is suggested that the reaction of benzophenone...

  9. 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…

  10. H2 O2 –HBr: A metal-free and organic solvent-free reagent system ...

    Indian Academy of Sciences (India)

    Administrator

    the manufacture of odorants, flavours, food and bev- erage. They serve also as principal intermediates in the production .... HBr reacts with H2O2 to produce free bromine. The generated bromine continues the bromination proc- ... remarkable advantage of this work, 4-nitro- benzaldehyde (table 4, Entry 6, yield = 47%) and.

  11. Synthesis of naphthoxazinone derivatives using silica-bonded S ...

    Indian Academy of Sciences (India)

    acid as catalyst under solvent-free conditions. KHODABAKHSH NIKNAM∗ ... conditions. The heterogeneous catalyst was recycled for five runs after the reaction of β-naphthol, benzaldehyde and urea without losing its catalytic activity. Keywords. .... through a short column chromatography using n-hexane/ ethyl acetate as ...

  12. Mesostructured SBA-15-Pr-SO 3 H: An efficient solid acid catalyst for ...

    Indian Academy of Sciences (India)

    ... 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, ...

  13. Role and structural characterization of plant aldehyde dehydrogenases from family 2 and family 7

    Czech Academy of Sciences Publication Activity Database

    Končitíková, R.; Vigouroux, A.; Kopečná, M.; Andree, T.; Bartoš, Jan; Šebela, M.; Moréra, S.; Kopečný, D.

    2015-01-01

    Roč. 468, Part: 1 (2015), s. 109-123 ISSN 0264-6021 R&D Projects: GA ČR GA15-22322S; GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : aldehyde dehydrogenase 2 (ALDH2) * aldehyde dehydrogenase 7 (ALDH7) * benzaldehyde Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 3.562, year: 2015

  14. Oxygen-rich molybdenum and chromium complexes: Synthesis ...

    Indian Academy of Sciences (India)

    Administrator

    with high turnover, but this apart, (3) catalytically reduces water present in organic solvent to dihydrogen while oxidising benzaldehyde and cinnamaldehyde to the respective acids. The same catalyst shows catalase type behaviour bringing out dioxygen from hydrogen peroxide. Reference. 1. Bandyopadhyay R, Biswas S, ...

  15. Sol-gel process preparation and evaluation of the analytical performances of an hydrazine specific chemical sensor

    International Nuclear Information System (INIS)

    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

  16. Synthesis, IR and NMR spectral correlations in some symmetrical ...

    African Journals Online (AJOL)

    A series of diimines have been synthesized by coupling of diamine with substituted benzaldehydes. The purities of these diimines were checked by their analytical and spectroscopic data. The spectral frequencies νCN (cm-1), NMR chemical shifts (δ, ppm) of C-H and C=N of these diimines have been correlated with ...

  17. Microwave-assisted silica-promoted solvent-free synthesis of ...

    Indian Academy of Sciences (India)

    PLATON (Spek, 2009). 2.3 General procedure for preparation of triazoloquinazo- linone derivatives (1a–1h)/benimidazoquinazolinone derivatives (2a–2h). A Slurry of equimolar quantities of 3-amino-1,2,4- triazole/2-amino benzimidazole, dimedone and benzaldehyde in a minimum quantity of ethanol/MDC was allowed to ...

  18. Synthesis and characterization of mononuclear copper (II ...

    Indian Academy of Sciences (India)

    Complexes 1–3 were found to be active catalysts for the oxidation of toluene, ethyl benzene and cyclohexane in the presence of hydrogen peroxide as the oxidant under mild conditions. Toluene was oxidized to benzyl alcohol and benzaldehyde, ethyl benzene was oxidized to 1-phenylethanol and acetophenone and ...

  19. Adding Value to Bioethanol through a Purification Process Revamp

    DEFF Research Database (Denmark)

    Bisgaard, Thomas; Mauricio Iglesias, Miguel; Huusom, Jakob Kjøbsted

    2017-01-01

    analyzed experimentally: Acetaldehyde, 1-propanal, 1-butanal, crotonaldehyde, benzaldehyde, ethyl acetate, methanol, 1-propanol, 1-butanol, 2-butanol, 2-methyl-l-propanol, 2-methyl-l-butanol, and 3-methyl-1-butanol. A simulation platform was established and evaluated with excellent agreement compared...

  20. Synthesis, characterization, scale-up and catalytic behaviour of ...

    Indian Academy of Sciences (India)

    The particles show good catalytic activity for the oxidation of oxalic acid and benzaldehyde under mild temperature conditions. ... The XRD measurements show cubic spinel phase and Debye–Scherrer relation was used to measure average particle size. ..... Zacheis G A, Gray K A and Kamat P V 2001 J. Phys. Chem. B.

  1. 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.

  2. 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

  3. 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…

  4. Fulltext PDF

    Indian Academy of Sciences (India)

    Administrator

    3.2 Thallium(III). The reactions of diphenylthallium(III) hydroxide with a series of thiosemicarbazones in water–ethanol medium at room temperature formed novel diphenylthallium(III) thiosemicarbazonates of stoichiometry [TlPh2(L)] {HL : R = N3–N2H–C1(S)–N1H2, cyclopentanone (28), benzaldehyde (29), ...

  5. Synthesis, spectroscopic characterization and catalytic oxidation ...

    Indian Academy of Sciences (India)

    Oxidation of alcohols to carbonyl compounds is one of the most pivotal functional group transformations in organic synthesis. Three important natural enzymes ..... 6. Benzyl alcohol. Benzaldehyde. 57. 1-Phenylethanol. Acetophenone. 65. Cyclohexanol. Cyclohexanone. 49 a Reaction time, 5 h. b Yields based on substrate.

  6. A convenient and efficient one-step method for the synthesis of ...

    African Journals Online (AJOL)

    hydroxy-5-methyl benzaldehyde with a mole of N,N'-bis(2-pyridyl)dopamine in THF at ambient conditions in high yield (75-80%). KEY WORDS: Dicompartmental ligand, Synthesis, Phenol-based ligand, Acyclic ligand. Bull. Chem. Soc. Ethiop. 2010 ...

  7. Selective oxidation of benzyl alcohol in dense CO2

    DEFF Research Database (Denmark)

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

    2012-01-01

    systems, based on the Cubic Plus Association (CPA) equation of state, is utilized in order to gain insight into the phase behavior during the palladium-catalyzed selective oxidation of benzyl alcohol to benzaldehyde. The catalytic reaction was studied in a tubular continuous reactor both under biphasic...

  8. Combined experimental and theoretical mechanistic investigation of the Barbier allylation in aqueous media

    DEFF Research Database (Denmark)

    Dam, Johan Hygum; Fristrup, Peter; Madsen, Robert

    2008-01-01

    -up of negative charge along with a small positive secondary kinetic isotope effect (k(H)/k(D) = 1.06) indicated that the selectivity-determining step was the generation of the radical anion of benzaldehyde. The reaction through a six-membered transition state was modeled using density functional theory...

  9. 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...

  10. 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

    2017-02-02

    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.

  11. Mutations Closer to the Active Site Improve the Promiscuous Aldolase Activity of 4-Oxalocrotonate Tautomerase More Effectively than Distant Mutations

    NARCIS (Netherlands)

    Rahimi, Mehran; van der Meer, Jan-Ytzen; Geertsema, Edzard M; Poddar, Harshwardhan; Baas, Bert-Jan; Poelarends, Gerrit J

    2016-01-01

    The enzyme 4-oxalocrotonate tautomerase (4-OT), which catalyzes enol-keto tautomerization as part of a degradative pathway for aromatic hydrocarbons, promiscuously catalyzes various carbon-carbon bond-forming reactions. These include the aldol condensation of acetaldehyde with benzaldehyde to yield

  12. Synthesis, characterization, scale-up and catalytic behaviour of ...

    Indian Academy of Sciences (India)

    Highly uniform cobalt oxide (Co3O4) nanoparticles were synthesized via thermal decomposition of cobalt hydroxy carbonates with particle size around 16 ± 1 nm. The process gives reproducible results in batches of 1–5 kg. The particles show good catalytic activity for the oxidation of oxalic acid and benzaldehyde under ...

  13. Fe+3-montmorillonite K10: As an effective and reusable catalyst for ...

    African Journals Online (AJOL)

    In this study, a novel, clean, convenient, appropriate and environmentally benign route to dihydropyrimidinone and thione derivatives has been developed using the reaction between various benzaldehydes, urea or thiourea, and ethyl acetoacetate in the presence of Fe+3-montmorillonite K10 under grind condition.

  14. The synthesis of N–Zn, N–Cu complexes involving 2-amino pyridine ...

    Indian Academy of Sciences (India)

    Administrator

    alcohol, and the reaction mixture was refluxed for. 14 h. The mixture was filtered to furnish white cry- .... benzaldehyde to 2-nitro-1-phenylethanol was esta- blished according to the content ratio of the remin- ... Zn(OAc)2 ·2 H2O in ethanol, THF or acetonitrile, the corresponding complexes were obtained after reflux- ing for 14 ...

  15. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Home; Journals; Journal of Chemical Sciences. Masayuki Shirai. Articles written in Journal of Chemical Sciences. Volume 126 Issue 2 March 2014 pp 395-401. Enhancement of reaction rates for catalytic benzaldehyde hydrogenation and sorbitol dehydration in water solvent by addition of carbon dioxide · Masayuki Shirai ...

  16. Two expedient 'one-pot'methods for synthesis of -aryl- ...

    Indian Academy of Sciences (India)

    Keywords. -aryl--mercaptoketones; anhydrous potassium carbonate; amberlyst-15; chalcones; thia-Michael addition. Abstract. Two expedient one-pot methods have been developed for synthesis of -aryl--mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve ...

  17. 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.

  18. 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....

  19. 21 CFR 582.60 - Synthetic flavoring substances and adjuvants.

    Science.gov (United States)

    2010-04-01

    ... butyrate. 3-Methyl-3-phenyl glycidic acid ethyl ester (ethyl-methyl-phenyl-glycidate, so-called strawberry aldehyde, C-16 aldehyde). Ethyl vanillin. Eugenol. Geranoil (3,7-dimethyl-2,6 and 3,6-octadien-1-ol.... Methyl anthranilate (methyl-2-aminobenzoate). Piperonal (3,4-methylenedioxy-benzaldehyde, heliotropin...

  20. ZnO nanoparticle as catalyst for efficient green one-pot synthesis of ...

    Indian Academy of Sciences (India)

    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 ...

  1. Uses of acetoacetanilide for the synthesis of thiophene derivatives ...

    African Journals Online (AJOL)

    Uses of acetoacetanilide for the synthesis of thiophene derivatives with cytotoxic activities. ... Bulletin of the Chemical Society of Ethiopia ... The latter was the key starting material for the synthesis of different thiophene and fused derivatives through its reaction with aryldiazonium chloride, benzaldehyde and acetic anhydride.

  2. 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

    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...

  3. Measuring reaction kinetics in a lab-on-a-Chip by microcoil NMR

    NARCIS (Netherlands)

    Wensink, H.; Benito-Lopez, F.; Hermes, D.C.; Verboom, Willem; Gardeniers, Johannes G.E.; Reinhoudt, David; van den Berg, Albert

    2005-01-01

    A microfluidic chip with an integrated planar microcoil was developed for Nuclear Magnetic Resonance (NMR) spectroscopy on samples with volumes of less than a microliter. Real-time monitoring of imine formation from benzaldehyde and aniline in the microreactor chip by NMR was demonstrated. The

  4. An interesting spectroscopic method for chromofluorogenic ...

    Indian Academy of Sciences (India)

    Fresh, double-distilled water was used throughout the experiments. Barbituric acid and 4-(N , N-Dimethyl- amino)benzaldehyde were obtained from Merck and. Sigma-Aldrich Co., respectively. Inorganic salts were obtained from Merck Co. The 1H and 13CNMR spectra were recorded on Bruker BioSpin 400 spectrometer at.

  5. Hydrodeoxygenation of aldehydes catalyzed by supported palladium catalysts

    Czech Academy of Sciences Publication Activity Database

    Procházková, D.; Zámostný, P.; Voláková, Martina; Červený, L.; Čejka, Jiří

    2007-01-01

    Roč. 332, č. 1 (2007), s. 56-64 ISSN 0926-860X Grant - others:GA ČR GA104/06/0684 Program:GA Institutional research plan: CEZ:AV0Z40400503 Keywords : hydrogenation * hydrodeoxygenation * benzaldehyde * cinnamaldehyde Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 3.166, year: 2007

  6. 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...

  7. 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.

  8. A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H ...

    Indian Academy of Sciences (India)

    Hydroxybenzaldehyde. N. N. OH. HO. 5. 70. 1g. 4-N,N-dimethyl amino benzaldehyde. N ..... 33 161 (b) Padia. J K, Field M, Hinton J, Meecham K, Pablo J, Trivedi B K and Webdale L 1998 J. Med. Chem. 41 1042 (c) Khilil. M A, Soliman R, Farghaly A M ...

  9. Mono(NCN-pincer palladium)-metalloporphyrin catalysts: evidence for supramolecular bimetallic catalysis

    NARCIS (Netherlands)

    Suijkerbuijk, B.M.J.M.; Schamhart, D. J.; Kooijman, H.; Spek, A.L.; van Koten, G.; Klein Gebbink, R.J.M.

    2010-01-01

    The synthesis and catalytic properties of ditopic mono-pincer-mono-porphyrin complexes were investigated. The statistical Adler condensation reaction of 3,5-bis(methoxymethyl)-4-bromo-benzaldehyde, p-tolylaldehyde, and pyrrole, furnished an AB3-type tetraphenylporphyrin, containing three

  10. 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

    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...

  11. Thiosemicarbazone complexes of the platinum metals. A story of ...

    Indian Academy of Sciences (India)

    , Os; X = Cl, Br) to afford complexes of type [M(PPh3)2(Hsaltsc)2], in which the salicylaldehyde thiosemicarbazone ligand is coordinated to the metal as a bidentate N,S-donor forming a four-membered chelate ring. Reaction of benzaldehyde ...

  12. Synthesis of New dihydropyrimidinones catalysed by dicationic ionic ...

    Indian Academy of Sciences (India)

    inelli reaction of multicomponents, 4-((2-chloroquinolin-3-yl) methoxy) benzaldehydes, ethyl acetoacetate and urea mediated and ... Dihydropyrimidinones; quinoline; dicationic ionic liquid; ethereal linkage; Biginelli reaction. 1. Introduction ...... thus rate of acceleration of Mannich reaction was found to be increased to give ...

  13. Amides and an alkaloid from Portulaca oleracea.

    Science.gov (United States)

    Kokubun, Tetsuo; Kite, Geoffrey C; Veitch, Nigel C; Simmonds, Monique S J

    2012-08-01

    A total of 16 phenolic compounds, including one new and five known N-cinnamoyl phenylethylamides, one new pyrrole alkaloid named portulacaldehyde, five phenylpropanoid acids and amides, and derivatives of benzaldehyde and benzoic acid, were isolated and identified from a polar fraction of an extract of Portulaca oleracea. Their structures were determined through spectroscopic analyses.

  14. Enantioselective aminocatalysis: Michael addition of unactivated ...

    Indian Academy of Sciences (India)

    KHIANGTE VANLALDINPUIA

    olefins and N-Boc imines of benzaldehyde to achieve up to 93% yield and 83% ee. More recently, Peddinti et al.,39 and Shao et al.,40,41 reported organocatalysts. *For correspondence. Electronic supplementary material: The online version of this article (doi:10.1007/s12039-017-1371-6) contains supplementary material,.

  15. Quantitative assessment of the effect of anhydrous zinc chloride ...

    African Journals Online (AJOL)

    ... MgSO4, H3COOH, Mg(ClO4)2 to activate the carbonyl group of benzaldehyde, catalyse the nucleophilic attack by amines, and dehydrate the system, and eliminate water as the final steps. Anhydrous zinc chloride has been extensively used in literature for its affordability and reliability, however there is limited information ...

  16. Kinetics, mechanism and thermodynamics of bisulfite-aldehyde adduct formation

    Energy Technology Data Exchange (ETDEWEB)

    Olson, T.M.; Boyce, S.D.; Hoffmann, M.R.

    1986-04-01

    The kinetics and mechanism of bisulfite addition to benzaldehyde were studied at low pH in order to assess the importance of this reaction in stabilizing S(IV) in fog-, cloud-, and rainwater. Previously, the authors established that appreciable concentrations of the formaldehyde-bisulfite adduct (HMSA) are often present in fogwater. Measured HMSA concentrations in fogwater often do not fully account for observed excess S(IV) concentrations, however, so that other S(IV)-aldehyde adducts may be present. Reaction rates were determined by monitoring the disappearance of benzaldehyde by U.V. spectrophotometry under pseudo-first order conditions, (S(IV))/sub T/ >>(phi-CHO)/sub T/, in the pH range 0 - 4.4 at 25/sup 0/C. The equilibrium constant was determined by dissolving the sodium salt of the addition compound in a solution adjusted to pH 3.9, and measuring the absorbance of the equilibrated solution at 250 nm. A literature value of the extinction coefficient for benzaldehyde was used to calculate the concentration of free benzaldehyde. All solutions were prepared under an N/sub 2/ atmosphere using deoxygenated, deionized water and ionic strength was maintained at 1.0 M with sodium chloride.

  17. Untitled

    Indian Academy of Sciences (India)

    ,10-dihalo compounds) and their triplet formation. T Nakayama, K Ibuki and K Hamanoue ... Electron-nuclear cross-relaxation effect on the photochemical reaction of benzaldehyde as studied by CIDNP and DNP Y Yamakage,. Q Meng, S S Ali, ...

  18. 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.

  19. 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.

  20. 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)

  1. Syntheses of 1-Aryl-5-nitro-1H-indazoles and a General One-Pot Route to 1-Aryl-1H-indazoles

    Directory of Open Access Journals (Sweden)

    Joel K. Annor-Gyamfi

    2018-03-01

    Full Text Available An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr ring closure in 45–90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73–96%, while the benzaldehyde series (63–73% required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62–78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

  2. 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.

  3. 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.

  4. Ultrasound-assisted synthesis of curcumin analogs promoted by activated chicken eggshells

    Science.gov (United States)

    Mardiana, L.; Ardiansah, B.; Septiarti, A.; Bakri, R.; Kosamagi, G.

    2017-07-01

    Curcumin has been widely known as a multifunctional natural product which has many biological activities. However, the biggest limitation for the large scale application of curcumin is its poor bioavailability. This research presented a cheap, mild and efficient solvent-free synthesis of monocarbonyl analogs of curcumin via Aldol condensation using activated chicken eggshells (ACE). Dibenzalpropanone as a product of Aldol condensation was prepared by mixing benzaldehyde and acetone using a simple glass tube in the presence of ACE under ultrasound irradiation (78 % yield), while dibenzalcyclohexanone was produced from the reaction of benzaldehyde with cyclohenxanone (81 %). The products have been characterized by FTIR, UV-Vis spectrophotometer and GC-MS instruments. The FTIR spectra show a significant absorption of carbonyl group that attached to the double bond in α,β-position at 1630-1660 cm-1. The molecular cation of m/z of 234 and 274 is in agreement with the products structures.

  5. Determination of volatile compounds by gas liquid chromatography in tropical fruit, guava (psidium guajav L.)

    International Nuclear Information System (INIS)

    Hussain, A.; Zeb-un-Nisa; Asi, M. R.; Ahmad, R.; Iqbal, Z.; Maqbool, A. B.

    2002-01-01

    Volatile flavor components from both white and pink guava fruits were collected using Likens-Nickerson concurrent Distillation Extraction method and were analyzed by GC/FID. In the essence collected by using likens-Nickerson concurrent distillation extraction apparatus, 23 compounds were present in white guava fruit, of which 11 compounds (furfural, alpha-pinene, trans-2-hexene-1-ol, 2-heptanone, benzaldehyde, hexyl acetate Beta-ionone, limonene, 2-nonanone, cinamyl acetate and octyl acetate) were identified. Similarly for pink guava fruit, 13 compounds out of 29 compounds were identified by comparing retention times of unknown with that of standard compounds and sniffing at the odour port. These were hexanal, furfural, 2-heptanone, benzaldehyde, methyl furfural hexyl acetate, beta-ionone, alpha-pinene, 2-nonanone, limonene, cinnamyl acetate, ethyl undecanoate and octyl acetate. (author)

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

    International Nuclear Information System (INIS)

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

    2010-01-01

    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.

  7. Kinetics and Mechanism of Oxidation of Aromatic Aldehydes by Imidazolium Dichromate in Aqueous Acetic Acid Medium

    Directory of Open Access Journals (Sweden)

    S. Sheik Mansoor

    2009-01-01

    Full Text Available The kinetics of oxidation of benzaldehyde (BA and para-substituted benzaldehydes by imidazolium dichromate (IDC has been studied in aqueous acetic acid medium in the presence of perchloric acid. The reaction is first order each in [IDC], [Substrate] and [H+]. The reaction rates have been determined at different temperatures and the activation parameters calculated. Electron withdrawing substituents are found to increase the reaction and electron releasing substituents are found to retard the rate of the reaction and the rate data obey the Hammett relationship. The products of the oxidation are the corresponding acids. The rate decreases with the increase in the water content of the medium. A suitable mechanism is proposed.

  8. EVALUATION OF THE SYNTHESIS AND STRUCTURE OF NEW AZETIDIN-2-ONES OF FERULIC ACID.

    Science.gov (United States)

    Stan, Cătălina Daniela; Drăgan, Maria; Pânzariu, Andreea; Profire, Lenuţa

    2016-01-01

    To synthesize some new azetidin-2-ones of ferulic acid and to evaluate them from physicochemical and spectral point of view. The synthesis was carried out in several steps: (i) obtaining the ferulic acid chloride; (ii) obtaining the ferulic acid hydrazide with hydrazine hydrate (98%); (iii) condensation of ferulic acid hydrazide with different benzaldehydes (2-hydroxy-/2-nitro-/4-chloro-/4- fluoro-/4-bromo-benzaldehyde) in order to obtain the corresponding hydrazones; (iv) cy- clization of ferulic acid hydrazones with chloroacethyl chloride in freshly distilled toluene medium and in the presence of triethylamine, resulting in the corresponding azetidin-2-ones. Six new azetidin-2-ones of ferulic acid were synthesized. They were characterized in terms of their physicochemical properties and their structure was confirmed by IR and 1H-NMR spectroscopy. Six new azetidin-2-ones of ferulic acid were synthesized, physicochemically characterized and validated spectrally. A

  9. Co(Salen Catalysed Oxidation of Synthetic Lignin-Like Polymer: Naoh Effects

    Directory of Open Access Journals (Sweden)

    Zhou Xue-Fei

    2014-09-01

    Full Text Available Abstract An attempt has been made to selectively oxidise synthetic lignin-like polymer for fine chemicals. The G- and S-type polymers (G- and S- type lignin model polymers were synthesized using simple aromatic compounds as starting materials and then oxidised to benzaldehydes by reacting them with Co(salen catalytic system. The reaction was characterized by measuring the change of the polymer with FTIR, C-13 NMR and GC-MS spectroscopy. The results obtained by the FTIR and C-13 NMR showed that the effects of NaOH were important and higher yield of benzaldehydes characterized by GC-MS in the presence of NaOH in the course of catalytic oxidation of the polymer demonstrated these effects. From the results, the catalyst could suitably be used in green procedures for lignin transformation.

  10. Chiral trialkylborane reducing agents. Preparation of 1-deuterio primary alcohols of high enantiomeric purity

    International Nuclear Information System (INIS)

    Midland, M.M.; Greer, S.; Tramontano, A.; Zderic, S.A.

    1979-01-01

    B-3-Pinanyl-9-borabicyclo[3.3.1]nonane (3-pinanyl-9-BBN, prepared from (+)-α-pinene and 9-BBN) is an effective chemical reagent for the asymmetric reduction of 1-deuterio aldehydes to chiral 1-deuterio primary alcohols. For example, benzaldehyde-1-d is reduced to pure (S)-(+)-benzyl-l-d alcohol. A deuterated reagent prepared from α-pinene and 9-BBN-9-d was found to reduce a variety of aromatic, aliphatic, and α,β-unsaturated aldehydes to the corresponding chiral primary 1-deuterio alcohols. In each case a large excess of the R enantiomer is formed. Steric factors seem to have little effect on the extent of asymmetric induction, but electron-donating para substituents on benzaldehyde slightly decrease the enantioselectivity of the reduction. A number of other chiral-9-BBN derivatives were investigated. A model is proposed to account for the high asymmetric inductions. 2 tables

  11. Synthesis of Benzoyl C-Phenylcalix[4]resorcinaryl Octaacetate and Cinnamoyl C-Phenylcalix[4]arene for UV Absorbers

    Directory of Open Access Journals (Sweden)

    Budiana I Gusti M. Ngurah

    2014-07-01

    Full Text Available A new upper rim-functionalized benzoyl C-phenylcalix[4]resorcinaryl octaacetate and cinnamoyl C-phenylcalix[4]resorcinarene have been synthesized and evaluated as the absorbers for ultraviolet radiation. The benzoyl C-phenylcalix[4]resorcinaryl octaacetate was synthesized in 3 steps. They were synthesis of C-phenilcalix[4]resorcinarene via acid-catalyzed-condensation of resorcinol and benzaldehyde, followed by O-acetylation and Friedel-Craft benzoylation. The cinnamoyl C-phenylcalix[4]resorcinarene was synthesized in 4 steps. They were synthesis of C-phenilcalix[4]resorcinarene via acid-catalyzed-condensation of resorcinol and benzaldehyde, followed by O-acetylation, Friedel-Craft cinnamoylation and hydrolysis. Spectroscopic analysis (UV showed that the target molecule absorbed the ultraviolet radiation between 200 and 400 nm with the maximum absorption at 240.50 nm (ε = 10.135 M-1 cm-1 and 243.50 nm (ε = 12.135 M-1 cm-1.

  12. 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.

  13. 4-Carbomethoxybenzaldehyde as a highly sensitive pre-column fluorescence derivatization reagent for 9,10-phenanthrenequinone.

    OpenAIRE

    Kishikawa, Naoya; Nakao, Maiko; Elgawish, Mohamed Saleh; Ohyama, Kaname; Nakashima, Kenichiro; Kuroda, Naotaka

    2011-01-01

    9,10-Phenanthrenequinone (PQ) is harmful environmental pollutant that is detected in airborne particulates. The measurement of PQ in the air should be necessary to evaluate the potential adverse effects of PQ on human health. We have recently developed a determination method for PQ based on the fluorescence derivatization of PQ using benzaldehyde and ammonium acetate as a reagent. In this study, in order to obtain more sensitive and selective fluorescence derivatization reaction, we measured ...

  14. Analysis of Volatile Organic Compounds Liberated and Metabolised by Human Umbilical Vein Endothelial Cells (HUVEC) In Vitro

    OpenAIRE

    Mochalski, Pawe?; Theurl, Markus; Sponring, Andreas; Unterkofler, Karl; Kirchmair, Rudolf; Amann, Anton

    2014-01-01

    Gas chromatography with mass spectrometric detection combined with head-space needle trap extraction as the pre-concentration technique was applied to identify and quantify volatile organic compounds released or metabolised by human umbilical vein endothelial cells. Amongst the consumed species there were eight aldehydes (2-methyl 2-propenal, 2-methyl propanal, 2-methyl butanal, 3-methyl butanal, n-hexanal, benzaldehyde, n-octanal and n-nonanal) and n-butyl acetate. Further eight compounds (e...

  15. Simple and novel synthetic method to mixed-donor podand

    Directory of Open Access Journals (Sweden)

    Fatemeh Moradgholi

    2015-06-01

    Full Text Available An efficient method for the synthesis of new compounds of dibenzo podand containing mixed-donor atom is described. The key starting materials for these podand was successfully prepared in 92% yield from 2-aminophenol and benzaldehyde in water. The structures of these new compounds were confirmed on the basis of IR, 1H NMR and 13C NMR and Ms spectroscopic data.

  16. 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...

  17. Anaerobic degradation of linear alkylbenzene sulfonate

    DEFF Research Database (Denmark)

    Mogensen, Anders Skibsted; Haagensen, Frank; Ahring, Birgitte Kiær

    2003-01-01

    % of the added C-12 LAS was bioavailable and 20% was biotransformed when spiking with 100 mg/L of C-12 LAS and a TS concentration of 14.2 mg/L. Enhanced bioavailability of C-12 LAS was obtained in an upflow anaerobic sludge blanket (UASB) reactor inoculated with granular sludge and sewage sludge. Biodegradation...... under thermophilic conditions was 37% with LAS as sole carbon source. Benzaldehyde was produced in the UASB reactor during LAS transformation....

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

    OpenAIRE

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

  19. An Environmentally Friendly Solvent-free Synthesis of 3,4 ...

    African Journals Online (AJOL)

    NICO

    La(OTf)3,16 BF3@OEt2,17 ionic liquids (BMIm@PF6 and BMIm@BF4),18 ... and use of moisture sensitive, toxic and costly catalysts. ... Analyzer. 3.1 Preparation of Dihydropyrimidinones 4a–n: General Procedure. A typical procedure is as follows: A mixture of benzaldehyde. (1 mmol), ethyl acetoacetate (1 mmol), urea ...

  20. Odor-Evoked Inhibition of Olfactory Sensory Neurons Drives Olfactory Perception in Drosophila

    Science.gov (United States)

    2017-05-22

    octanoate methyl-octanoate ethyl 3-hydroxybutyrate hexyl- acetate methyl- acetate 3-methylbutanol ethyl -cinnamate acetophenone benzaldehyde ethyl -benzoate... ethyl 3-hydroxybutyrate, an excitatory 123 odor for Or85a-OSNs, increased the membrane conductance of the same OSNs and 124 produced an inward...acetophenone and excitatory odor ethyl 3-hydroxybutyrate (Fig. 2a). Power spectral 136 analysis revealed similar waveforms between the basal inward

  1. 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.

  2. 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.

  3. Atualizando a química orgânica experimental da licenciatura

    OpenAIRE

    Navarro, Marcelo; Sena, Vera L. M. de; Srivastava, Rajendra M.; Navarro, Daniela M. do Amaral Ferraz

    2005-01-01

    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-chlorophenyl)phthalamic acid from phthalic anhydride and p-chloroaniline under solvent-free conditions. The experiments can be ...

  4. 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...... 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....

  5. 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.

  6. Preparation and Analytical Properties of 4-Hydroxybenzaldehyde, Biuret and Formaldehyde Terpolymer Resin

    OpenAIRE

    Bunian A. Shareef; Ibrahim F. Waheed; Kariem K. Jalaot

    2014-01-01

    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...

  7. 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.

  8. 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.

  9. 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.

  10. Encapsulation of N,N′,N″-tricyclohexylguanidine in hydrophobic zeolite Y: Synthesis and catalytic activity

    OpenAIRE

    Sercheli, Ricardo; Ferreira, Alfredo L. B.; Guerreiro, Mário C.; Vargas, Rogério Matheus; Sheldon, Roger A.; Schuchardt, Ulf

    1997-01-01

    Texto completo: acesso restrito. p.1325–1328 N,N′,N″-Tricyclohexylguanidine was encapsulated in hydrophobic zeolite Y by reacting N,N′-dicyclohexylcarbodiimide with cyclohexylamine within the supercage. The encapsulated guanidine catalyzes the addition reaction of acetone to benzaldehyde forming 4-phenyl-4-hydroxybutan-2-one as the principal product, as opposed to the homogeneous system which produces 4-phenyl-3-buten-2-one via condensation reaction.

  11. Electrochemical Advanced Oxidation Process for Shipboard Final Purification of Filtered Black Water, Gray Water, and Bilge Water, Vol. 1

    Science.gov (United States)

    2001-08-01

    all, the food additive that gives almond cookies their characteristic aroma. The values of NOH obtained with benzaldehyde were generally slightly...procedures are straightforward: (1) If the anode is contaminated with iron, it can be cleaned by soaking in a warm, dilute solution of citric acid. If...intentionally fouled anodes. We discovered long ago that even severe iron fouling can easily be removed by soaking the anodes in oxalic acid solution or warm

  12. Synthesis and Cytotoxicity of Chalcones and 5-Deoxyflavonoids

    OpenAIRE

    Jing Zhang; Xin-Ling Fu; Nan Yang; Qiu-An Wang

    2013-01-01

    Chalcones 1~8 and 5-deoxyflavonoids 9~22 were synthesized in good yields by aldol condensation, Algar-Flynn-Oyamada reaction, glycosidation, and deacetylation reaction, respectively, starting from 2-acetyl phenols substituted by methoxy or methoxymethoxy group and appropriately benzaldehydes substituted by methoxy, methoxymethoxy group, or chlorine. Among them, 13 and 17~22 are new compounds. The cytotoxicity bioassays of these chalcones and 5-deoxyflavonoids were screened using the sulforhod...

  13. 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.

  14. Profiling ephedrine prepared from N-methylalanine via the Akabori-Momotani reaction.

    Science.gov (United States)

    Doddridge, Alexandra; Collins, Michael; Salouros, Helen

    2018-03-01

    Novel methods for synthesising methylamphetamine precursors are appearing in clandestine laboratories within Australia. One such laboratory involved the synthesis of ephedrine from N-methylalanine and benzaldehyde via the Akabori-Momotani reaction. This article presents chiral and stable isotope ratios of ephedrine synthesised via this method, along with a chemical profile of methylamphetamine produced from this ephedrine. Based on the chiral results and the δ 13 C, δ 15 N, and δ 2 H values, it is possible to distinguish ephedrine made via the Akabori-Momotani reaction from ephedrine of a "natural", "semi-synthetic", or "fully-synthetic" origin. Methylamphetamine and ephedrine samples synthesised from benzaldehyde having an enriched δ 2 H value (ie, > 0‰), via the Akabori-Momotani reaction, had an isotopic profile which set them apart from all other methylamphetamine samples. It was noted, however, that using stable isotope ratios alone to determine the precursor of methylamphetamine is limited; they could not with confidence differentiate between methylamphetamine and ephedrine synthesised from benzaldehyde having a depleted δ 2 H value (ie, ephedrine sources and phenyl-2-propanone based methylamphetamine samples profiled. ©2017 Commonwealth of Australia. Drug Testing and Analysis ©2017 John Wiley & Sons, Ltd.

  15. Alteration of the substrate specificity of benzoylformate decarboxylase from Pseudomonas putida by directed evolution.

    Science.gov (United States)

    Lingen, Bettina; Kolter-Jung, Doris; Dünkelmann, Pascal; Feldmann, Ralf; Grötzinger, Joachim; Pohl, Martina; Müller, Michael

    2003-08-04

    Alteration of the substrate specificity of thiamin diphosphate (ThDP)-dependent benzoylformate decarboxylase (BFD) by error-prone PCR is described. Two mutant enzymes, L476Q and M365L-L461S, were identified that accept ortho-substituted benzaldehyde derivatives as donor substrates, which leads to the formation of 2-hydroxy ketones. Both variants, L476Q and M365L-L461S, selectively catalyze the formation of enantiopure (S)-2-hydroxy-1-(2-methylphenyl)propan-1-one with excellent yields, a reaction which is only poorly catalyzed by the wild-type enzyme. Different ortho-substituted benzaldehyde derivatives, such as 2-chloro-, 2-methoxy-, or 2-bromobenzaldehyde are accepted as donor substrates by both BFD variants as well and conversion with acetaldehyde resulted in the corresponding (S)-2-hydroxy-1-phenylpropan-1-one derivatives. As deduced from modeling studies based on the 3D structure of wild-type BFD, reduction of the side chain size at position L461 probably results in an enlarged substrate binding site and facilitates the initial binding of ortho-substituted benzaldehyde derivatives to the cofactor ThDP.

  16. Minute Impurities Contribute Significantly to Olfactory Receptor Ligand Studies: Tales from Testing the Vibration Theory.

    Science.gov (United States)

    Paoli, M; Münch, D; Haase, A; Skoulakis, E; Turin, L; Galizia, C G

    2017-01-01

    Several studies have attempted to test the vibrational hypothesis of odorant receptor activation in behavioral and physiological studies using deuterated compounds as odorants. The results have been mixed. Here, we attempted to test how deuterated compounds activate odorant receptors using calcium imaging of the fruit fly antennal lobe. We found specific activation of one area of the antennal lobe corresponding to inputs from a specific receptor. However, upon more detailed analysis, we discovered that an impurity of 0.0006% ethyl acetate in a chemical sample of benzaldehyde-d 5 was entirely responsible for a sizable odorant-evoked response in Drosophila melanogaster olfactory receptor cells expressing dOr42b. Without gas chromatographic purification within the experimental setup, this impurity would have created a difference in the responses of deuterated and nondeuterated benzaldehyde, suggesting that dOr42b be a vibration sensitive receptor, which we show here not to be the case. Our results point to a broad problem in the literature on use of non-GC-pure compounds to test receptor selectivity, and we suggest how the limitations can be overcome in future studies.

  17. 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. Copyright © 2015 Elsevier B.V. All rights reserved.

  18. Heterogeneous Reactions between Toluene and NO2 on Mineral Particles under Simulated Atmospheric Conditions.

    Science.gov (United States)

    Niu, Hejingying; Li, Kezhi; Chu, Biwu; Su, Wenkang; Li, Junhua

    2017-09-05

    Heterogeneous reactions between organic and inorganic gases with aerosols are important for the study of smog occurrence and development. In this study, heterogeneous reactions between toluene and NO 2 with three atmospheric mineral particles in the presence or absence of UV light were investigated. The three mineral particles were SiO 2 , α-Fe 2 O 3 , and BS (butlerite and szmolnokite). In a dark environment, benzaldehyde was produced on α-Fe 2 O 3 . For BS, nitrotoluene and benzaldehyde were obtained. No aromatic products were produced in the absence of NO 2 in the system. In the presence of UV irradiation, benzaldehyde was detected on the SiO 2 surface. Identical products were produced in the presence and absence of UV light over α-Fe 2 O 3 and BS. UV light promoted nitrite to nitrate on mineral particles surface. On the basisi of the X-ray photoelectron spectroscopy (XPS) results, a portion of BS was reduced from Fe 3+ to Fe 2+ with the adsorption of toluene or the reaction with toluene and NO 2 . Sulfate may play a key role in the generation of nitrotoluene on BS particles. From this research, the heterogeneous reactions between organic and inorganic gases with aerosols that occur during smog events will be better understood.

  19. 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.

  20. Toxicity of benzyl alcohol in adult and neonatal mice.

    Science.gov (United States)

    McCloskey, S E; Gershanik, J J; Lertora, J J; White, L; George, W J

    1986-07-01

    Benzyl alcohol, a bacteriostatic agent found in many parenteral preparations, has been implicated as the agent responsible for precipitating "the gasping syndrome" in premature neonates. To investigate this toxicity, benzyl alcohol was administered intraperitoneally to adult (23-28 g) and neonatal (2-7 g) CD-1 male mice. Gross behavioral changes were monitored. Low doses (less than 800 mg/kg) produced minimal toxic effects within an initial 4-h observation period. At the end of this time, the LD50 was determined to be 1000 mg/kg for both age groups. When mortality in the adult group was observed after 7 d following a single treatment with benzyl alcohol, the LD50 on day 7 was determined to be 650 mg/kg. Rapid absorption and conversion of benzyl alcohol to its primary metabolite, benzaldehyde, occurred within both experimental groups; the plasma levels of each were comparable in both neonatal and mature animals when determined by GC. In an attempt to alter the toxicity of benzyl alcohol, pyrazole and disulfiram were used to inhibit the activities of alcohol dehydrogenase and aldehyde dehydrogenase, respectively. Treatment with pyrazole, before benzyl alcohol exposure, resulted in an increase in benzyl alcohol levels to 203% of control values and a marked increase in toxicity. Although pretreatment with disulfiram led to benzaldehyde levels which were 368% of control values, toxicity was unchanged. These data imply that the acute toxicity of benzyl alcohol, which includes sedation, dyspnea, and loss of motor function, is due to the alcohol itself and not to its metabolite, benzaldehyde.

  1. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives

    International Nuclear Information System (INIS)

    Elhadi, S. A.

    2004-09-01

    Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, 1 H-and 13 C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl -6-sulphanilamide-quinolin-4-carboxylic acid showed the highest activity against the four standard tested organisms.(Author)

  2. Single-site SBA-15 supported zirconium catalysts. Synthesis, characterization and toward cyanosilylation reaction

    International Nuclear Information System (INIS)

    Xu, Wei; Yu, Bo; Zhang, Ying; Chen, Xi; Zhang, Guofang; Gao, Ziwei

    2015-01-01

    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 2 ) 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 -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 -500 supported zirconium complexes were characterized by in situ FT-IR, 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

  3. 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.

  4. (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.

  5. New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

    Directory of Open Access Journals (Sweden)

    Cristina Nastasă

    2015-09-01

    Full Text Available New series of hydrazones 5–18 were synthesized, in good yields, by reacting 4-methyl-2-(4-(trifluoromethylphenylthiazole-5-carbohydrazide with differently substituted benzaldehyde. The resulting compounds were characterized via elemental analysis, physico-chemical and spectral data. An antimicrobial screening was done, using Gram (+, Gram (− bacteria and one fungal strain. Tested molecules displayed moderate-to-good growth inhibition activity. 2,2-Diphenyl-1-picrylhydrazide assay was used to test the antioxidant properties of the compounds. Monohydroxy (14–16, para-fluorine (13 and 2,4-dichlorine (17 derivatives exhibited better free-radical scavenging ability than the other investigated molecules.

  6. New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation.

    Science.gov (United States)

    Nastasă, Cristina; Tiperciuc, Brîndușa; Duma, Mihaela; Benedec, Daniela; Oniga, Ovidiu

    2015-09-18

    New series of hydrazones 5-18 were synthesized, in good yields, by reacting 4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole-5-carbohydrazide with differently substituted benzaldehyde. The resulting compounds were characterized via elemental analysis, physico-chemical and spectral data. An antimicrobial screening was done, using Gram (+), Gram (-) bacteria and one fungal strain. Tested molecules displayed moderate-to-good growth inhibition activity. 2,2-Diphenyl-1-picrylhydrazide assay was used to test the antioxidant properties of the compounds. Monohydroxy (14-16), para-fluorine (13) and 2,4-dichlorine (17) derivatives exhibited better free-radical scavenging ability than the other investigated molecules.

  7. The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy)-N-phenylbenzamide derivatives

    OpenAIRE

    IOANA M. C. IENAŞCU; ALFA X. LUPEA; IULIANA M. POPESCU; MIRABELA A. PĂDURE; ALINA D. ZAMFIR

    2009-01-01

    To obtain biologically active compounds, the synthesis of some new derivatives with an o-hydroxybenzamide structure was performed. The ethyl esters 4–6 were obtained by the reaction of 5-chloro-2-hydroxy-N-phenylbenzamide and chloro-substituted acid ethyl esters 1–3 in ethyl methyl ketone. The obtained ethyl esters were condensed with hydrazine yielding the hydrazides 7–8. The hydrazones 11–14 were obtained by the reaction of the hydrazides and the chloro-substituted benzaldehydes 9–10. All t...

  8. 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

    2013-03-01

    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&z.rad; 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.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

  9. 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.

  10. 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.

  11. 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. Copyright © 2012 Elsevier B.V. All rights reserved.

  12. 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

  13. Mechanism of Prototropy. III. Kinetics of the Tautomerization of Benzylidene-Benzylamine. comparison of the influence of hydrogen and alkyl groups on the SE2' reaction rate

    International Nuclear Information System (INIS)

    Perez Ossorio, R.; Gamboa, J. M.; Martinez Utrilla, R.

    1961-01-01

    The rate of the proto tropic change of benzylidene-benzylamine has been determined by using azomethine 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-α-alkyl benzylamine and α-alkyl benzylidene-benzyl amines in the same experimental conditions in order to establish ethe influence of alkyl group on this reaction. (Author) 14 refs

  14. Synthesis and structural confirmation of natural 1,3-diarylpropanes

    Directory of Open Access Journals (Sweden)

    Almeida Paulo A. de

    1999-01-01

    Full Text Available 1-(4?-Hydroxy-5?-methyl-2?-methoxyphenyl-3-(2"-hydroxy-4",5"-methylenedioxyphenyl propane (7, 1,3-diarylpropane isolated from Iryanthera laevis, 1-(4?-hydroxy-2?-methoxyphenyl-3-(4"-hydroxyphenylpropane (2, broussonin B and 1-(2?-hydroxy-4?-methoxyphenyl-3-(4"-hydroxyphenylpropane (1, broussonin A, isolated from Broussonetia papyrifera Vent. (Moraceae, and 1-(2?,4?-dimethoxyphenyl-3-(4"-hydroxyphenylpropane, a synthetic product prepared by catalytic hydrogenation of 4-O-benzyl-2?,4?-dimethoxychalcone, were synthesized. The synthetic pathway employed in this work involved the catalytic hydrogenation of chalcones obtained by base condensation of acetophenones and benzaldehydes.

  15. The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

    Directory of Open Access Journals (Sweden)

    Erika Bálint

    2017-01-01

    Full Text Available 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.

  16. 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.

  17. synthesis and labelling of some nitrogenous heterocyclic compounds

    International Nuclear Information System (INIS)

    Mahmoud, A.A.L.

    2002-01-01

    the imidazole nucleus has wide range of pharmaceutical activities . also , radioiodinated compounds are used in nuclear medicine. this thesis deals with the synthesis of 2-(iodophenyl)-4-oxazoline-5-ons e, which are used as starting materials in the synthesis of the corresponding imidazolinone derivatives. also, it deals with radioiodination f the synthesized compounds to evaluate their application in nuclear medicine. interaction of o- iodo hippuric acid (I) with aromatic aldehydes (i.e., benzaldehyde, p- methoxybenzaldehyde and p- nitrobenzaldehyde) in acetic anhydride and in the presence of fused sodium acetate effected cyclization to afford the corresponding 2-(2-iodophenyl)-4-arylidene- 2-oxazoline-5-ones(l l a-c )

  18. KF/Al2O3 as a Recyclable Basic Catalyst for 1,3-Dipolar Cycloaddition Reaction: Synthesis of Indolizine-1-Carbonitrile Derivatives

    Directory of Open Access Journals (Sweden)

    Abaszadeh Mehdi

    2017-07-01

    Full Text Available KF/Al2O3 as a green and efficient catalyst has been used for synthesis of indolizine-1-carbonitrile derivatives. It can be proceeded by using 1,3-dipolar cycloaddition reaction of 1-alkyl-2-chloropyridinium bromides, malononitrile and benzaldehyde in ethanol, at reflux. The great advantage of this catalyst is the ease of handling. KF/Al2O3 can be used and removed by filtration, avoiding cumbersome aqueous workups and decreasing solvent waste handling issues. High conversions, short reaction times and a cleaner reaction profiles are some of the outstanding advantages of this method.

  19. 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

    The chiral aziridino alcohols 1 -3 have been prepared either from amino acids (1a from serine; 1b - 1i and 3 from threonine; 2a - 2e from allo-threonine) or via asymmetric synthesis (1j, 1k, 1l and 2f from methyl cinnamate). These easily available ligands act as catalysts for the enantioselective...... 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...

  20. 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.

  1. Novel acyclonucleoside analog bearing a 1,2,4-triazole–Schiff base: Synthesis, characterization and analytical studies using square wave-adsorptive stripping voltammetry and HPLC

    OpenAIRE

    Ali F. Alghamdi; Nadjet Rezki

    2017-01-01

    New acyclonucleoside analogs tethered by a 1,2,4-triazole scaffold were synthesized through the condensation of 4-amino-5-(2-phenyleth-1-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) with benzaldehyde followed by the alkylation of the resulting Schiff base (3)with 2-bromoethanol, 3-chloropropanol and/or 3-chloropropan-1,2-diol. Voltammetric studies were carried out for the analysis of 1 × 10−6 mol L−1 of the newly synthesized acyclonucleoside analogs (4–6) using square wave-adsorptive stripp...

  2. 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.

  3. Influence of harvest date on volatile and sensory profile of vine leaves infusions from two Portuguese red grape varieties

    OpenAIRE

    Jordão António M.; Correia Ana C.; Nunes Fernando M.; Cosme Fernanda

    2017-01-01

    The main object of the present study was to investigate the volatile composition and sensorial profile of vine leaves infusions prepared from vine leaves collected 30 and 60 days after grape harvest from two Portuguese red grape varieties (Touriga Nacional and Tinta Roriz). Twelve volatile compounds were detected in vine leaves infusions (6-methyl-5-hepten-2-one, 1-undecene, Z-citral, cedrenol, DL-limonene, 2,4-hexadien-2-ol, benzaldehyde, heptane-1,2,4,6-tetraene, cyclohexene 1-methyl-4-(1-m...

  4. Determination of NH{sub 2} concentration on 3-aminopropyl tri-ethoxy silane layers and cyclopropylamine plasma polymers by liquid-phase derivatization with 5-iodo 2-furaldehyde

    Energy Technology Data Exchange (ETDEWEB)

    Manakhov, Anton, E-mail: ant-manahov@ya.ru [National University of Science and Technology “MISiS”, Leninsky pr. 4, Moscow 119049 (Russian Federation); RG Plasma Technologies, CEITEC—Central European Institute of Technology, Masaryk University, Kotlářská, 2, 61137 Brno (Czech Republic); Čechal, Jan [CEITEC—Central European Institute of Technology, Brno University of Technology, Purkyňova 123, 612 00 Brno (Czech Republic); Institute of Physical Engineering, Brno University of Technology, Technická 2896/2, 616 69 Brno (Czech Republic); Michlíček, Miroslav [RG Plasma Technologies, CEITEC—Central European Institute of Technology, Masaryk University, Kotlářská, 2, 61137 Brno (Czech Republic); Department of Physical Electronics, Faculty of Science, Masaryk University, Kotlářská 2, 61137 Brno (Czech Republic); Shtansky, Dmitry V. [National University of Science and Technology “MISiS”, Leninsky pr. 4, Moscow 119049 (Russian Federation)

    2017-08-31

    Highlights: • A new method for primary amines derivatization is proposed and validated. • The chemical structure of APTES layer is studied. • The derivatization by 5-iodo 2-furaldehyde allowed to avoid side reactions in contrast to 4-trifluoromethyl benzaldehyde derivatization. - Abstract: The quantification of concentration of primary amines, e.g. in plasma polymerized layers is a very important task for surface analysis. However, the commonly used procedure, such as gas phase derivatization with benzaldehydes, shows several drawbacks, the most important of which are the side reaction effects. In the present study we propose and validate a liquid phase derivatization using 5-iodo 2-furaldehyde (IFA). It was demonstrated that the content of NH{sub 2} groups can be determined from the atomic concentrations measured by X-ray photoelectron spectroscopy (XPS), in particular from the ratio of I 3d and N 1s peak intensities. First, we demonstrate the method on a prototypical system such as 3-aminopropyl tri-ethoxy silane (APTES) layer. Here the XPS analysis carried out after reaction of APTES layer with IFA gives the fraction of primary amines (NH{sub 2}/N) of 38.3 ± 7.9%. Comparing this value with that obtained by N 1s curve fitting of APTES layer giving 40.9 ± 9.5% of amine groups, it can be concluded that all primary amines were derivatized by reaction with IFA. The second system to demonstrate the method comprises cyclopropylamine (CPA) plasma polymers that were free from conjugated imines. In this case the method gives the NH{sub 2} fraction ∼8.5%. This value is closely matching the NH{sub 2}/N ratio estimated by 4-trifluoromethyl benzaldehyde (TFBA) derivatization. The reaction of IFA with CPA plasma polymer exhibiting high density of conjugated imines revealed the NH{sub 2}/N fraction of ∼10.8%. This value was significantly lower compared to 17.3% estimated by TFBA derivatization. As the overestimated density of primary amines measured by TFBA

  5. 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.

  6. Structure-activity relationship study of phenylpyrazole derivatives as a novel class of anti-HIV agents.

    Science.gov (United States)

    Mizuhara, Tsukasa; Kato, Takayuki; Hirai, Atsushi; Kurihara, Hideki; Shimada, Yasuhiro; Taniguchi, Masahiko; Maeta, Hideki; Togami, Hiroaki; Shimura, Kazuya; Matsuoka, Masao; Okazaki, Shiho; Takeuchi, Tomoki; Ohno, Hiroaki; Oishi, Shinya; Fujii, Nobutaka

    2013-08-15

    The structure-activity relationship of phenylpyrazole derivative 1 was investigated for the development of novel anti-HIV agents. Initial efforts revealed that the diazenyl group can be replaced by an aminomethylene group. In addition, we synthesized various derivatives by the reductive amination of benzaldehydes with 5-aminopyrazoles and carried out parallel structural optimization on the benzyl group and the pyrazole ring. This optimization led to a six-fold more potent derivative 32j than the lead compound 1, and this derivative has a 3',4'-dichloro-(1,1'-biphenyl)-3-yl group. Copyright © 2013 Elsevier Ltd. All rights reserved.

  7. Identification of non-host semiochemicals for the brown dog tick, Rhipicephalus sanguineus sensu lato (Acari: Ixodidae), from tick-resistant beagles, Canis lupus familiaris.

    Science.gov (United States)

    Borges, Lígia Miranda Ferreira; de Oliveira Filho, Jaires Gomes; Ferreira, Lorena Lopes; Louly, Carla Cristina Braz; Pickett, John A; Birkett, Michael A

    2015-07-01

    Studies have shown that the brown dog tick, Rhipicephalus sanguineus sensu lato, when fed on the beagle breed of dog, Canis lupus familiaris, development negatively affected in comparison with tick development after feeding on the English cocker spaniel breed. Thus leading to the suggestion that beagle dogs are be tick-resistant dogs. Behavioural studies have demonstrated that more ticks are attracted by extracts from cocker spaniels than from beagles and that the odour of beagles is a repellent. To test the hypothesis that resistant hosts produce repellent compounds, we undertook comparative chemical analysis on beagle odour and cocker spaniel extracts using coupled high-resolution gas chromatography-mass spectrometry (GC-MS) and also used Petri-dish and olfactometer behavioural assays to assess the response of ticks to identified non-host compounds. The beagle odour extracts contained almost three times as many chemical compounds as cocker spaniel samples. Several non-host compounds were identified, i.e. 2-hexanone, benzaldehyde, nonane, decane and undecane. In Petri-dish assays, 2-hexanone was repellent at 30 min at concentrations of 0.200 and 0.050 mg cm(-2), whilst at 10 min, the 0.100 mg cm(-2) concentration was repellent. Benzaldehyde repelled ticks at 30 min (0.200 mg cm(-2)) and at 5 min (0.050 mg cm(-2)). Undecane was repellent for R. sanguineus s.l. ticks for the first 5 min at the highest concentration tested. Nonane and decane did not show any significant repellency at any concentration or time evaluated. When 2-hexanone and benzaldehyde were combined, an increase in the repellency rate was observed, with activity comparable or better than N,N-diethyl-3-methylbenzamide (DEET). In olfactometer bioassays, a 1:1 mixture of 2-hexanone:benzaldehyde and DEET were repellent for R. sanguineus s.l. adults at the concentration of 0.200 mg cm(-2). This study identified non-host semiochemicals that mediate avoidance of the beagle dog breed by R. sanguineus s

  8. 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.

  9. 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.

  10. 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.

  11. Synthesize and Characterization of Hydroxypropyl-N-octanealkyl Chitosan Ramification

    Science.gov (United States)

    Tan, Fu-neng

    2018-03-01

    A new type of amphiphilic ramification, hydroxypropyl-N-octanealkyl chitosan was prepared from chitosan via hydrophilic group and hydrophobic group were introduced. We could protect the amino group of chitosan via the reaction of chitosan and benzaldehyde could get Schiff base structure. Structures of the products were characterized with FT-IR, elemental analysis, themogrammetry (TG) analysis and X-ray diffraction. The degree of substitution of hydrophobic group was studied by elemental analysis. The result showed this chitosan ramification was soluble, biocompatible, biodegradable and nontoxic.

  12. Volatiles of quince fruit and leaf (Cydonia oblonga Mill. from Serbia

    Directory of Open Access Journals (Sweden)

    Veličković, D.T.

    2016-12-01

    Full Text Available The subject of this study is the chemical composition of volatile fractions from the fruit and leaf of quince (Cydonia oblonga Mill.. Dominant components were ethyl 2-methylbutanoate, (E,E--farnesene, ethyl- (2E,4Z-decadienoate, pentadecanol, -acoradienol, ethyl decanoate, ethyl octanoate, (E-nerolidol, ethyl dodecanoate, 14-hydroxy-9-epi-(E-caryophyllene, (2Z,6E-farnesol, -cedrene. Volatile fraction of the fruit was also characterized by ethyl-(4Z-decenoate, ethyl 9-dodecenoate, ethyl hexanoate, ethyl nonanoate and - cyclocitral, where in the leaf n-octanal, n-hexanol, n-nonanal and benzaldehyde were present.

  13. The Preparation of Some Compounds for Testing as Insect Repellents

    Science.gov (United States)

    1945-12-28

    levulinic acid , propyl ester A-Cyanostyrene C15H18°3 C9H?N m pr or b.p.. nun a.p. Mithod 112 9 1.447t- E 61-71 1 1.527-’ L 48-54...siethylene group and an excess of formalin« Warmed 2 to 4 hours and poured into a largo Volume of water. AP. Benzaldehyde and levulinic acid v;ere...after acidification with hydrochloric acid * Alt* Butyraldehyde and levulinic acid were condensed as described in method A?« AN. c*—Bromoesters were

  14. The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy-N-phenylbenzamide derivatives

    Directory of Open Access Journals (Sweden)

    IOANA M. C. IENAŞCU

    2009-08-01

    Full Text Available To obtain biologically active compounds, the synthesis of some new derivatives with an o-hydroxybenzamide structure was performed. The ethyl esters 4–6 were obtained by the reaction of 5-chloro-2-hydroxy-N-phenylbenzamide and chloro-substituted acid ethyl esters 1–3 in ethyl methyl ketone. The obtained ethyl esters were condensed with hydrazine yielding the hydrazides 7–8. The hydrazones 11–14 were obtained by the reaction of the hydrazides and the chloro-substituted benzaldehydes 9–10. All the newly synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, MS and elemental analyses.

  15. 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...... carbamate to serve as a urea precursor. The building blocks were incorporated at the N-terminal of a resin-supported dipeptide through urea formation. Subsequent treatment with acid liberated the aldehyde quantitatively. A penultimate tryptophan residue gave rise, under the acetic conditions...

  16. Crystal structure of (E-4-benzylidene-6-phenyl-1,2,3,4,7,8,9,10-octahydrophenanthridine

    Directory of Open Access Journals (Sweden)

    Baidaa K. Al-Rubaye

    2017-07-01

    Full Text Available The preparation of the title compound, C26H25N, was achieved by the condensation of an ethanolic mixture of benzaldehyde, cyclohexanone and ammonium acetate in a 2:1:1 molar ratio. There are two crystallographically independent molecules in the asymmetric unit. The two cyclohexyl rings adopt an anti-envelope conformation with the benzyl moiety adopting a cis conformation with respect to the nitrogen atom of the phenanthridine segment. In the crystal, molecules are linked through C—H...N interactions into hydrogen-bonded chains that are further arranged into distinct layers by weak offset π–π interactions.

  17. Synthesis and Analgesic Activity of Some New Pyrazoles and Triazoles Bearing a 6,8-Dibromo-2-methylquinazoline Moiety

    Directory of Open Access Journals (Sweden)

    Hosam A. Saad

    2011-12-01

    Full Text Available 2-(6,8-Dibromo-2-methylquinazolin-4-yloxy-acetohydrazide (4 was prepared by the reaction of 6,8-dibromo-2-methylbenzo-[d][1,3]oxazin-4-one with formamide to afford quinazolinone 2, followed by alkylation with ethyl chloroacetate to give the ester 3. Treatment of ester 3 with hydrazine hydrate and benzaldehyde afforded 4 and styryl quinazoline 5. The hydrazide was reacted with triethyl orthoformate, acetylacetone and ethyl acetoacetate and benzaldehyde derivatives to afford the corresponding pyrazoles 6, 7, 9 and hydrazone derivatives 10a-c. Cyclization of hydrazones 10a-c with thioglycolic acid afforded the thiazole derivatives 11a-c. Reaction of the hydrazide with isothiocyanate derivatives afforded hydrazinecarbothioamide derivatives 12a-c, which cyclized to triazole-3-thiols and thiadiazoles 13a-c and 14a-c, respectively. Fusion of the hydrazide with phthalimide afforded the annelated compound 1,2,4-triazolo[3,4-a]isoindol-5-one (15. The newly synthesized compounds were characterized by their spectral (IR, 1H-, 13C-NMR data. Selected compounds were screened for analgesic activity.

  18. Structural studies and investigation on the activity of imidazole-derived thiosemicarbazones and hydrazones against crop-related fungi.

    Science.gov (United States)

    Reis, Débora C; Despaigne, Angel A Recio; Da Silva, Jeferson G; Silva, Nayane F; Vilela, Camila F; Mendes, Isolda C; Takahashi, Jacqueline A; Beraldo, Heloisa

    2013-10-14

    New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

  19. New hydrazones of ferulic acid: synthesis, characterization and biological activity.

    Science.gov (United States)

    Wolszleger, Maria; Stan, Cătălina Daniela; Apotrosoaei, Maria; Vasincu, Ioana; Pânzariu, Andreea; Profire, Lenuţa

    2014-01-01

    The ferulic acid (4-hydroxy-3-methoxy-cinnamic acid) is a phenolic compound with important antioxidant effects and which nowadays is being extensively studied for his potential indications in inflammatory and neurodegenerative diseases, hypertension, atherosclerosis, etc. The synthesis of new ferulic acid compounds with potential antioxidant activity. The synthesis of the designed compounds was performed in several steps: (i) the obtaining of ferulic acid chloride by reacting of ferulic acid with thionyl chloride; (ii) the reaction between the ferulic acid chloride and hydrazine hydrate 98% to obtain the ferulic acid hydrazide; (iii) the condensation of ferrulic acid hydrazide with various benzaldehydes (2-hydroxy/3-hydroxy/4-hydroxy/2-nitro/3-nitro/4-nitro/2-methoxi/ 4-chloro/4-fluoro/4-bromo-benzaldehyde) resulting the correspond- ing hydrazones. The structure of the synthesized compounds was confirmed by FT-IR spectroscopy and the evaluation of antioxidant potential was achieved by determining the total antioxidant capacity and reducing power. In this study new hydrazones of ferulic acid have been synthesized, physic-chemical and spectral characterized. The evaluation of antioxidant potential using in vitro methods showed the favorable influence of the structural modulation on the antioxidant effects of ferulic acid.

  20. Synthesis and anti-inflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole.

    Science.gov (United States)

    Moldovan, Cristina Mariana; Oniga, Ovidiu; Pârvu, Alina; Tiperciuc, Brînduşa; Verite, Philippe; Pîrnău, Adrian; Crişan, Ovidiu; Bojiţă, Marius; Pop, Raluca

    2011-02-01

    This work describes recent results from our research program aiming at the synthesis and evaluation of new compounds acting as potential anti-inflammatory drugs. A series of novel acyl-hydrazones bearing 2-aryl-thiazole moiety were synthesized by the condensation between derivatives of 4-[2-(4-methyl-2-phenyl-thiazole-5-yl)-2-oxo-ethoxy]-benzaldehyde and 2, 3 or 4-(2-aryl-thiazol-4-ylmethoxy)-benzaldehyde, respectively and different carboxylic acid hydrazides. The structures of newly synthesized compounds were established by the combined use of IR, (1)H NMR, mass spectral data and elemental analysis. These compounds were tested in vivo for their anti-inflammatory activity, in an acute experimental inflammation. The acute phase bone marrow response, phagocytes' activity and NO synthesis were evaluated. Compounds 10, 15, 17, 18 and 22 reduced the absolute leukocytes count due to the lower neutrophils percentage. Phagocitary index was decreased by all the compounds. Seven of them reduced the phagocitary activity. Five compounds inhibited NO synthesis, 3, 4, 16 and 22 stronger than Meloxicam, the anti-inflammatory reference drug. Copyright © 2010 Elsevier Masson SAS. All rights reserved.

  1. Highly sensitive and selective determination of 9, 10-phenanthrenequinone in airborne particulates using high-performance liquid chromatography with pre-column derivatization and fluorescence detection.

    Science.gov (United States)

    Kishikawa, Naoya; Wada, Mitsuhiro; Ohba, Yoshihito; Nakashima, Kenichiro; Kuroda, Naotaka

    2004-11-19

    9,10-Phenanthrenequinone (PQ), is one of the components of diesel exhaust particulates, has potent harmful effects on human health. For the determination of PQ in airborne particulates, a highly sensitive and selective high-performance liquid chromatography (HPLC) method was developed with fluorescence detection following the pre-column fluorescent derivatization. PQ was derivatized with benzaldehyde as a derivatizing reagent in the presence of ammonium acetate to give fluorescent 2-phenyl-1H-phenanthro [9,10-d] imidazole. The maximum fluorescence intensity of the derivative was observed by the reaction with 0.2M benzaldehyde and 0.5 M ammonium acetate at 100 degrees C for 30 min. The HPLC separation of fluorescent derivative of PQ was performed within 20 min on an ODS column with a mixture of acetonitrile-water (55:45, v/v) as a mobile phase. Highly sensitive and selective determination of PQ was attained with the detection limit of 5 fmol (S/N = 3). By the proposed method, PQ in airborne particulates was successfully determined in the range 0.26-0.30 ng/m3 (n = 3).

  2. Selective and Efficient Solvent Extraction of Copper(II Ions from Chloride Solutions by Oxime Extractants

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    Zahra Kaboli Tanha

    2016-06-01

    Full Text Available Oxime extractants 3-tert-butyl-2-hydroxy-5-methyl benzaldehyde oxime (HL1 and 3-tert-butyl-2-hydroxy-5-methoxy benzaldehyde oxime (HL2 were synthesized and characterized by conventional spectroscopic methods. Suitable lipophilic nature of the prepared extractants allowed examining the ability of these molecules for extraction-separation of copper from its mixture with normally associated metal ions by performing competitive extraction experiments of Cu(II, Co(II, Ni(II, Zn(II, Cd(II and Pb(II ions from chloride solutions. Both ligands transfer selectively the copper ions into dichloromethane by a cation exchange mechanism. Conventional log-log analysis and isotherm curves showed that Cu(II ions are extracted as the complexes with 1:2 metal to ligand ratio by both extractants. Verification of the effect of the organic diluent used in the extraction of copper ions by HL1 and HL2 demonstrated that the extraction efficiency varies as: dichloromethane ~ dichloroethane > toluene > xylene > ethylacetate. Time dependency investigation of the extraction processes revealed that the kinetics of the extraction of copper by HL2 is more rapid than that of HL1. The application of the ligands for extraction-separation of copper ions from leach solutions of cobalt and nickel-cadmium filter-cakes of a zinc production plants was evaluated.

  3. Cytotoxic conjugates of betulinic acid and substituted triazoles prepared by Huisgen Cycloaddition from 30-azidoderivatives.

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    Veronika Sidova

    Full Text Available 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.

  4. Synthesis and characterization of a novel series of meso (nitrophenyl and meso (carboxyphenyl substituted porphyrins

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    Schiavon Marco A.

    2000-01-01

    Full Text Available The anionic 5,10,15-tris(4-carboxyphenyl, 20-mono(2-nitrophenyl porphyrin (1, 5,10(or 15-bis(4-carboxyphenyl, 15(or 10,20-bis(2-nitrophenylporphyrin (2 and 5-mono(4-carboxyphenyl, 10,15,20-tris(2-nitrophenylporphyrin (3 were sinthesized directly by reaction of pyrrole with substituted benzaldehydes in nitrobenzene/propionic acid media. The benzaldehydes molar ratio was controlled to optimize the synthesis and purification of the desired porphyrins. This new series of porphyrins was characterised by TLC, mass spectrometry (FAB MS, ¹H NMR, UV/Vis, IR and electrochemistry. 5,10,15,20-Tetrakis(4-carboxyphenylporphyrin (4 and 5,10,15,20-Tetrakis(2-nitrophenylporphyrin (5 were also characterised for comparative purposes, completing the series The electrochemical reduction was investigated for the free base and corresponding iron(III porphyrins on glassy carbon and mercury electrodes. The reduction potentials showed the expected dependence on the number of electron-withdrawing nitro groups present on the porphyrin ring providing additional evidences for the characterisation of the synthesised compounds.

  5. Aroma peculiarities of apricot (Armeniaca vulgaris Lam. and cherry-plum (Prunus cerasifera Ehrh. flowers

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    В. М. Горіна

    2013-02-01

    Full Text Available In the component composition of volatile solutions determining fragrance of the flowers in apricot and cherry-plum varieties and Prunus brigantiaca Vill. x Armeniaca vulgaris Lam. hybrids there are 36 highest hydrocarbons and benzaldehyde that prevail. There are fewer amounts of the solutions which scare bees (benzaldehyde in the fragrance of cherry-plum varieties as compared to the flowers of apricot and hybrids. At the same time, the content of tricosane, pentacosane, docosane, heneycosane, eicosane, nonadecan that probably attract bees is higher in the cherry-plum flowers than in the fragrance of apricot and hybrid flowers. The average three years yield of cherry-plum plants (Nikitska Zhovta 10,7 and Salgirskaya Rumjanaya 28,5 t/ ha is higher than for apricot (Recolte de Schatene 0,3; Rodnik 2,9; Ananasniy Tsurupinsky 7,4 t/ha and hybrids (8110 – 5,2; 8098 – 6,4 t/ha that could be explained with better pollination of flowers and better fruit formation. Prevailing components of flower aroma of these plants    and their possible link with yield of the objects in questions have been analyzed.

  6. Electrophysiological studies of olfaction in the whip spider Phrynus parvulus (Arachnida, Amblypygi).

    Science.gov (United States)

    Hebets; Chapman

    2000-11-01

    The olfactory response of the whip spider Phrynus parvulus from Costa Rica was examined using a technique analogous to that used for insect electroantennograms on the tarsi of the antenniform legs which bear multiporous sensilla. Responses to 42 chemicals representing different chain lengths of alkanes, carboxylic acids, alcohols, aldehydes, and ketones, as well as some esters, monoterpenes, and phenolics were examined. Fifty-four percent of the chemicals tested elicited responses. Concentration-response curves were generated for guaiacol, hexanal, methyl salicylate, benzaldehyde, octanoic acid, and linalool. Guaiacol, benzaldehyde, and hexanol elicited the greatest responses and no differences were detected between the sexes. Compounds with chain lengths of six carbon atoms generated strong responses and most monocarboxylic acids and ring compounds elicited responses. Some compounds produced increases in potential believed to arise from a hyperpolarizing effect on the neurons. The broad spectrum of chemicals to which these animals respond is similar to results of other studies examining the general olfactory sense of insects. It is possible that odor learning plays a significant role in the behavior of amblypygids.

  7. Study on Honey Quality Evaluation and Detection of Adulteration by Analysis of Volatile Compounds

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    Kružík Vojtěch

    2017-06-01

    Full Text Available Fast evaluation of honey quality is a topical and significant problem of the food industry, bee keepers and consumers. In this work, 22 samples of commercially available honey aromas (with methyl and ethyl esters of phenylacetic acid predominated, 13 samples of authentic honey collected directly from bee keepers (characterised by high content of benzaldehyde, 2-phenylethanol, hotrienol and 2-phenylacetaldehyde and 63 honeys purchased from an outdoor market were evaluated based on volatiles profiles determined through solid-phase microextraction coupled with gas chromatography-mass spectrometry (SPME-GC/MS and then suspicious samples were identified. The results were statistically processed and compared with results of a sensory analysis. Six honeys, which differed significantly in volatiles profiles (outliers detected by Factor Analysis, selected volatile substance representation (furan-2-carbaldehyde, 1,4-dimethylpyrazole, benzaldehyde, 2-phenylacetaldehyde and honey aroma intensity and pleasantness were subjected to targeted analyses (i.e. determination of 5-(hydroxymethyl-2-furaldehyde, diastase activity, unauthorized additive presence. Four of these suspicious samples were found to have high content of 5-(hydroxymethyl-2-furaldehyde (more than 40 mg/kg, three honeys had low values for diastase activity (less than 8 and three samples positive for triacetin addition. The fact that all these samples revealed a breach of least one of the selected quality parameters defined by the Codex Alimentarius standard proved the proposed methodology to be a useful tool for fast quality evaluation of honey.

  8. Scanning tunneling microscopy investigation of nano-structured α-K5PW11(M x OH2)O39(M = Mn(II), Co(II), Ni(II), and Zn(II)) Keggin heteropolyacid catalyst monolayers.

    Science.gov (United States)

    Choi, Jung Ho; Kang, Tae Hun; Bang, Yongju; Yoo, Jaekyeong; Jun, Jin Oh; Song, In Kyu

    2014-11-01

    Nano-structured α-K5PW11(M x OH2)O39 (M = Mn(II), Co(II), Ni(II), and Zn(II)) Keggin heteropolyacids (HPAs) were investigated by scanning tunneling microscopy (STM) and tunneling spectroscopy (TS) measurements in order to elucidate their redox property and oxidation catalysis. HPA molecules formed two-dimensional self-assembled monolayer arrays on highly oriented pyrolytic graphite (HOPG) surface. Furthermore, HPAs exhibited a distinctive current-voltage behavior referred to as negative differential resistance (NDR) phenomenon. The measured NDR peak voltage of HPAs was correlated with the reduction potential and the absorption edge energy determined by electrochemical method and UV-visible spectroscopy, respectively. NDR peak voltage of HPAs appeared at less negative voltage with increasing reduction potential and with decreasing UV-visible absorption edge energy. The correlations strongly suggested that NDR phenomenon was closely related to the redox property of HPAs. Vapor-phase oxidation of benzyl alcohol to benzaldehyde was carried out as a model reaction to track the oxidation catalysis of HPAs. NDR peak voltage appeared at less negative voltage with increasing yield for benzaldehyde.

  9. Combined experimental and theoretical mechanistic investigation of the Barbier allylation in aqueous media.

    Science.gov (United States)

    Dam, Johan Hygum; Fristrup, Peter; Madsen, Robert

    2008-04-18

    The Barbier allylation of a series of para-substituted benzaldehydes with allylbromide in the presence of Zn, In, Sn, Sb, Bi, and Mg was investigated using competition experiments. In all cases, the slope of the Hammett plots indicated a build-up of negative charge in the selectivity-determining step. For Zn, In, Sn, Sb, and Bi, an inverse secondary kinetic isotope effect was found (kH/kD = 0.75-0.95), which was compatible with the formation of a discrete organometallic species prior to allylation via a closed six-membered transition state. With Mg, a significantly larger build-up of negative charge along with a small positive secondary kinetic isotope effect (kH/kD = 1.06) indicated that the selectivity-determining step was the generation of the radical anion of benzaldehyde. The reaction through a six-membered transition state was modeled using density functional theory with the effect of solvent described by a polarized continuum model. The calculated secondary deuterium isotope effects based on this mechanism were found to be in good agreement with experimental values, thus adding further support to this mechanistic scenario.

  10. Seasonal evaluation of disinfection by-products throughout two full-scale drinking water treatment plants.

    Science.gov (United States)

    Zhong, Xin; Cui, Chongwei; Yu, Shuili

    2017-07-01

    Carbonyl compounds can occur alpha-hydrogens or beta-diketones substitution reactions with disinfectants contributed to halogenated by-products formation. The objective of this research was to study the occurrence and fate of carbonyl compounds as ozonation by-products at two full-scale drinking water treatment plants (DWTPs) using different disinfectants for one year. The quality of the raw water used in both plants was varied according to the season. The higher carbonyl compounds concentrations were found in raw water in spring. Up to 15 (as the sum of both DWTPs) of the 24 carbonyl compounds selected for this work were found after disinfection. The dominant carbonyl compounds were formaldehyde, glyoxal, methyl-glyoxal, fumaric, benzoic, protocatechuic and 3-hydroxybenzoic acid at both DWTPs. In the following steps in each treatment plant, the concentration patterns of these carbonyl compounds differed depending on the type of disinfectant applied. Benzaldehyde was the only aromatic aldehyde detected after oxidation with ozone in spring. As compared with DWTP 1, five new carbonyl compounds were formed (crotonaldehyde, benzaldehyde, formic, oxalic and malonic acid) disinfection by ozone, and the levels of the carbonyl compounds increased. In addition, pre-ozonation (PO) and main ozonation (OZ) increased the levels of carbonyl compounds, however coagulation/flocculation (CF), sand filtration (SF) and granular activated carbon filtration (GAC) decreased the levels of carbonyl compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

  11. Field observations of volatile organic compound (VOC) exchange in red oaks

    Science.gov (United States)

    Cappellin, Luca; Algarra Alarcon, Alberto; Herdlinger-Blatt, Irina; Sanchez, Juaquin; Biasioli, Franco; Martin, Scot T.; Loreto, Francesco; McKinney, Karena A.

    2017-03-01

    Volatile organic compounds (VOCs) emitted by forests strongly affect the chemical composition of the atmosphere. While the emission of isoprenoids has been largely characterized, forests also exchange many oxygenated VOCs (oVOCs), including methanol, acetone, methyl ethyl ketone (MEK), and acetaldehyde, which are less well understood. We monitored total branch-level exchange of VOCs of a strong isoprene emitter (Quercus rubra L.) in a mixed forest in New England, where canopy-level fluxes of VOCs had been previously measured. We report daily exchange of several oVOCs and investigated unknown sources and sinks, finding several novel insights. In particular, we found that emission of MEK is linked to uptake of methyl vinyl ketone (MVK), a product of isoprene oxidation. The link was confirmed by corollary experiments proving in vivo detoxification of MVK, which is harmful to plants. Comparison of MEK, MVK, and isoprene fluxes provided an indirect indication of within-plant isoprene oxidation. Furthermore, besides confirming bidirectional exchange of acetaldehyde, we also report for the first time direct evidence of benzaldehyde bidirectional exchange in forest plants. Net emission or deposition of benzaldehyde was found in different periods of measurements, indicating an unknown foliar sink that may influence atmospheric concentrations. Other VOCs, including methanol, acetone, and monoterpenes, showed clear daily emission trends but no deposition. Measured VOC emission and deposition rates were generally consistent with their ecosystem-scale flux measurements at a nearby site.

  12. Aldol Reactions of Axially Chiral 5-Methyl-2-(o-arylimino-3-(o-aryl-thiazolidine-4-ones

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    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.

  13. Ligand-tailored single-site silica supported titanium catalysts: Synthesis, characterization and towards cyanosilylation reaction

    International Nuclear Information System (INIS)

    Xu, Wei; Li, Yani; Yu, Bo; Yang, Jindou; Zhang, Ying; Chen, Xi; Zhang, Guofang; Gao, Ziwei

    2015-01-01

    A successive anchoring of Ti(NMe 2 ) 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 silica was conducted by SOMC strategy in moderate conditions. The silica, monitored by in-situ Fourier transform infrared spectroscopy (in-situ FT-IR), was pretreated at different temperatures (200, 500 and 800 °C). The ligand tailored silica-supported titanium complexes were characterized by in-situ FT-IR, 13 C CP MAS-NMR, X-ray photoelectron spectroscopy (XPS), X-ray absorption near edge structure (XANES) and elemental analysis in detail, verifying that the surface titanium species are single sited. The catalytic activity of the ligand tailored single-site silica supported titanium complexes was evaluated by a cyanosilylation of benzaldehyde. The results showed that the catalytic activity is dependent strongly on the dehydroxylation temperatures of silica and the configuration of the ligands. - Graphical abstract: The ligand-tailored silica supported “single site” titanium complexes were synthesized by SOMC strategy and fully characterized. Their catalytic activity were evaluated by benzaldehyde silylcyanation. - Highlights: • Single-site silica supported Ti active species was prepared by SOMC technique. • O-donor ligand tailored Ti surface species was synthesized. • The surface species was characterized by XPS, 13 C CP-MAS NMR, XANES etc. • Catalytic activity of the Ti active species in silylcyanation reaction was evaluated

  14. Evidence for acetyl coenzyme A and cinnamoyl coenzyme A in the anaerobic toluene mineralization pathway in Azoarcus tolulyticus Tol-4.

    Science.gov (United States)

    Chee-Sanford, J C; Frost, J W; Fries, M R; Zhou, J; Tiedje, J M

    1996-01-01

    A toluene-degrading denitrifier, Azoarcus tolulyticus Tol-4, was one of eight similar strains isolated from three petroleum-contaminated aquifer sediments. When the strain was grown anaerobically on toluene, 68% of the carbon from toluene was found as CO2 and 30% was found as biomass. Strain Tol-4 had a doubling time of 4.3 h, a Vmax of 50 micromol x min-1 x g of protein-1, and a cellular yield of 49.6 g x mol of toluene-1. Benzoate appeared to be an intermediate, since F-benzoates accumulated from F-toluenes and [14C]benzoate was produced from [14C]toluene in the presence of excess benzoate. Two metabolites, E-phenylitaconic acid (1 to 2%) and benzylsuccinic acid (toluene, [14C]acetate, and cinnamic acid. Evidence for anaerobic toluene metabolism by methyl group oxidation was not found, since benzylsuccinic acid and E-phenylitaconic acid were not detected after incubation with benzylalcohol and benzaldehyde, nor were benzylalcohol and benzaldehyde detected even in 14C trapping experiments. PMID:8975623

  15. A specific affinity reagent to distinguish aldehyde dehydrogenases and oxidases. Enzymes catalyzing aldehyde oxidation in an adult moth

    International Nuclear Information System (INIS)

    Tasayco, M.L.; Prestwich, G.D.

    1990-01-01

    Aldehyde dehydrogenase (ALDH) and oxidase (AO) enzymes from the tissue extracts of male and female tobacco budworm moth (Heliothis virescens) were identified after electrophoretic protein separation. AO activity was visualized using formazan- or horseradish peroxidase-mediated staining coupled to the AO-catalyzed oxidation of benzaldehyde. A set of six soluble AO enzymes with isoelectric points from pI 4.6 to 5.3 were detected primarily in the antennal extracts. Partially purified antennal AO enzymes also oxidized both (Z)-9-tetradecenal and (Z)-11-hexadecenal, the two major pheromone components of this moth. ALDH activity was detected using a tritium-labeled affinity reagent based on a known irreversible inhibitor of this enzyme. This labeled vinyl ketone, [3H](Z)-1,11-hexadecadien-3-one, was synthesized and used to covalently modify the soluble ALDH enzymes from tissue extracts. Molecular subunits of potential ALDH enzymes were visualized in the fluorescence autoradiograms of sodium dodecyl sulfate-polyacrylamide gel electrophoresis-separated proteins of the antenna, head, and leg tissues. Covalent modification of these protein subunits decreased specifically in the presence of excess pheromone aldehyde or benzaldehyde. Labeled vinyl ketones are thus novel tools for the identification of molecular subunits of ALDH enzymes

  16. 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.

  17. Radiolysis of benzyl alcohol in aqueous solution by external gamma-irradiation

    International Nuclear Information System (INIS)

    Ikebuchi, Hideharu; Kido, Yasumasa; Urakubo, Goro

    1977-01-01

    Radiolysis of 0.05% aqueous solution of benzyl alcohol with 60 Co γ-rays ranging from 1 x 10 4 to 7 x 10 5 rad was investigated, in order to presume the change of it contained in radiopharmaceuticals. For both O 2 free and oxygenated solutions, an approximately linear relationship holds between the retaining benzyl alcohol and dose in the range from 1 x 10 5 to 7 x 10 5 rads. The G(-M) values of benzyl alcohol calculated from the relation were 2.34 in the absence and 1.92 in presence of oxygen. In the presence of oxygen, a main product was benzaldehyde and its G value was 0.87. In the absence of oxygen, the main products of the radiolysis were dibenzyl, benzyl phenylcalbinol and hydrobenzoin, which were regarded as the radical-reaction products of PhCH 2 and PhCHOH, and the yield of benzaldehyde was negligible. Irrespective of the presence of oxygen, o- and p-hydroxylated products of benzyl alcohol were found only in small quantity. (auth.)

  18. Characterization of the Key Aroma Compounds in Proso Millet Wine Using Headspace Solid-Phase Microextraction and Gas Chromatography-Mass Spectrometry

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    Jingke Liu

    2018-02-01

    Full Text Available The volatile compounds in proso millet wine were extracted by headspace solid-phase microextraction (85 μm polyacrylate (PA, 100 μm polydimethylsiloxane (PDMS, 75 μm Carboxen (CAR/PDMS, and 50/30 μm divinylbenzene (DVB/CAR/PDMS fibers, and analyzed using gas chromatography-mass spectrometry; the odor characteristics and intensities were analyzed by the odor activity value (OAV. Different sample preparation factors were used to optimize this method: sample amount, extraction time, extraction temperature, and content of NaCl. A total of 64 volatile compounds were identified from the wine sample, including 14 esters, seven alcohols, five aldehydes, five ketones, 12 benzene derivatives, 12 hydrocarbons, two terpenes, three phenols, two acids, and two heterocycles. Ethyl benzeneacetate, phenylethyl alcohol, and benzaldehyde were the main volatile compounds found in the samples. According to their OAVs, 14 volatile compounds were determined to be odor-active compounds (OAV > 1, and benzaldehyde, benzeneacetaldehyde, 1-methyl-naphthalene, 2-methyl-naphthalene, and biphenyl were the prominent odor-active compounds (OAV > 50, having a high OAV. Principal component analysis (PCA showed the difference of distribution of the 64 volatile compounds and 14 odor-active compounds with four solid-phase microextraction (SPME fibers.

  19. Toxicity of benzyl alcohol in adult and neonatal mice

    International Nuclear Information System (INIS)

    McCloskey, S.E.

    1987-01-01

    Benzyl alcohol (BA) is an aromatic alcohol, which is used as a bacteriostat in a variety of parenteral preparations. In 1982, it was implicated as the agent responsible for precipitating The Gasping Syndrome in premature neonates. The investigate further this toxicity, BA was administered, intraperiotoneally, to adult and neonatal CD-1 male mice. Gross behavioral changes were monitored. Low doses produced minimal toxic effects within an initial 4 hour observation period. At the end of this time, the LD 50 was determined to be 1000 mg/kg for both age groups. Death was due to respiratory arrest in all cases. Rapid absorption and conversion of BA to its primary metabolite, benzaldehyde, was demonstrated by gas chromatographic analysis of plasma from both experimental groups. The conversion of BA to benzaldehyde was confirmed in in vitro by using both horse-liver and mouse liver ADH. The inhibition of alcohol dehydrogenase (ADH) by pyrazole was similarly demonstrated in both enzyme systems. 14 C-labelled BA was utilized to determine the distribution of BA and its metabolites in the body, and to possibly pinpoint a target organ of toxicity

  20. Effect of crop development on biogenic emissions from plant populations grown in closed plant growth chambers

    Science.gov (United States)

    Batten, J. H.; Stutte, G. W.; Wheeler, R. M.

    1995-01-01

    The Biomass Production Chamber at John F. Kennedy Space Center is a closed plant growth chamber facility that can be used to monitor the level of biogenic emissions from large populations of plants throughout their entire growth cycle. The head space atmosphere of a 26-day-old lettuce (Lactuca sativa cv. Waldmann's Green) stand was repeatedly sampled and emissions identified and quantified using GC-mass spectrometry. Concentrations of dimethyl sulphide, carbon disulphide, alpha-pinene, furan and 2-methylfuran were not significantly different throughout the day; whereas, isoprene showed significant differences in concentration between samples collected in light and dark periods. Volatile organic compounds from the atmosphere of wheat (Triticum aestivum cv. Yecora Rojo) were analysed and quantified from planting to maturity. Volatile plant-derived compounds included 1-butanol, 2-ethyl-1-hexanol, nonanal, benzaldehyde, tetramethylurea, tetramethylthiourea, 2-methylfuran and 3-methylfuran. Concentrations of volatiles were determined during seedling establishment, vegetative growth, anthesis, grain fill and senescence and found to vary depending on the developmental stage. Atmospheric concentrations of benzaldehyde and nonanal were highest during anthesis, 2-methylfuran and 3-methylfuran concentrations were greatest during grain fill, and the concentration of the tetramethylurea peaked during senescence.

  1. 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. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  2. 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

  3. 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.

  4. Changes in the viability of Strongyloides ransomi larvae (Nematoda, Rhabditida under the influence of synthetic flavourings

    Directory of Open Access Journals (Sweden)

    A. A. Boyko

    2017-01-01

    Full Text Available One of the most common nematodes of pigs globally is Strongyloides ransomi Schwartz and Alicata 1930. It usually causes aggravation of physiological indicators of its hosts and damage to their immune system. Also it is a good modelling object for the evaluation of the antiparasitic activity of new antihelminthic drugs. We conducted laboratory experiments to assess the effect of flavouring additives with flower odour (benzaldehyde, citral, D-limonene and β-ionone upon the viability of S. ransomi larvae. The mortality rate was calculated for 24 hours exposure at four concentrations of each substance (10, 1, 0.1 и 0.01 g/l with eight replications. The lowest LD50 values were obtained for citral (97 mg/l and benzaldehyde (142 mg/l. These substances are recommended for further evaluation of their antihelminthic effect in experiments using laboratory animals. Unlike other substances, the effect of β-ionone and D-limonene even at a concentration of 10 g/l after 24 hours caused the death of <50% of S. ransomi larvae. The study of flavouring additives with flowery odour, which are permitted to be used in food for humans and also to be used in cosmetics, is a promising field for research aimed at the development of new antiparasitic drugs.

  5. Contribution of ALDH1A1 isozyme to detoxification of aldehydes present in food products.

    Science.gov (United States)

    Sołobodowska, Sylwia; Giebułtowicz, Joanna; Wolinowska, Renata; Wroczyński, Piotr

    2012-01-01

    Even though food awareness is so developed and more and more people pay attention to what their diet is composed of, it is not possible to exclude all potentially dangerous substances present in our diet. One group of such compounds may be aldehydes as several studies indicate that they can be mutagenic, carcinogenic, genotoxic and cytotoxic. These relatively reactive organic molecules are natural constituents of food. They are also extensively used by food industry as additives giving aroma and taste. Fortunately many enzyme systems were developed to protect us against these toxic compounds, one of which is aldehyde dehydrogenase enzyme superfamily. As mouth is the first part of digestive system it seems crucial for detoxifying toxic substances introduced with our diet. The only ALDH isozyme present in saliva is ALDH3A1, which has very high affinity towards aromatic aldehydes commonly found in food. However, because of hyposalivation, which is not uncommon nowadays, the effectiveness of this barrier can be drastically diminished. As another member of this enzyme family, isozyme ALDH1A1 is also present in digestive system its possible contribution to detoxification of "food" aldehydes was addressed. Kinetic parameters (Km, Vmax) of recombinant ALDH1A1 towards several aliphatic and aromatic aldehydes occurring in food products (vanillin, citral, furfural, cinnamaldehyde, anisaldehyde, benzaldehyde and trans-hexenal) were determined by measuring the increase of NADH fluorescence after adding various concentrations of aldehyde substrates. Rates were used to construct the Lineweaver-Burk plot from which Km and Vmax (measured relative to that of benzaldehyde which was assigned the value of 100) values were calculated. The following results were obtained: 0.04 +/- 0.06 microM and 277 +/- 81 for anisaldehyde, 0.86 +/- 0.03 mciroM and 50 +/- 3 for vanillin, 0.18 +/- 0.05 mciroM and 93 +/- 9 for trans-2-hexenal, 0.17 +/- 0.03 microM and 201 +/- 32 for cinnamaldehyde, 5

  6. Benzene formation in electronic cigarettes.

    Directory of Open Access Journals (Sweden)

    James F Pankow

    Full Text Available The heating of the fluids used in electronic cigarettes ("e-cigarettes" used to create "vaping" aerosols is capable of causing a wide range of degradation reaction products. We investigated formation of benzene (an important human carcinogen from e-cigarette fluids containing propylene glycol (PG, glycerol (GL, benzoic acid, the flavor chemical benzaldehyde, and nicotine.Three e-cigarette devices were used: the JUULTM "pod" system (provides no user accessible settings other than flavor cartridge choice, and two refill tank systems that allowed a range of user accessible power settings. Benzene in the e-cigarette aerosols was determined by gas chromatography/mass spectrometry. Benzene formation was ND (not detected in the JUUL system. In the two tank systems benzene was found to form from propylene glycol (PG and glycerol (GL, and from the additives benzoic acid and benzaldehyde, especially at high power settings. With 50:50 PG+GL, for tank device 1 at 6W and 13W, the formed benzene concentrations were 1.9 and 750 μg/m3. For tank device 2, at 6W and 25W, the formed concentrations were ND and 1.8 μg/m3. With benzoic acid and benzaldehyde at ~10 mg/mL, for tank device 1, values at 13W were as high as 5000 μg/m3. For tank device 2 at 25W, all values were ≤~100 μg/m3. These values may be compared with what can be expected in a conventional (tobacco cigarette, namely 200,000 μg/m3. Thus, the risks from benzene will be lower from e-cigarettes than from conventional cigarettes. However, ambient benzene air concentrations in the U.S. have typically been 1 μg/m3, so that benzene has been named the largest single known cancer-risk air toxic in the U.S. For non-smokers, chronically repeated exposure to benzene from e-cigarettes at levels such as 100 or higher μg/m3 will not be of negligible risk.

  7. Photochemical reductions of benzil and benzoin in the presence of triethylamine and TiO2 photocatalyst

    International Nuclear Information System (INIS)

    Park, Joon Woo; Kim, Eun Kyung; Koh Park, Kwang Hee

    2002-01-01

    This paper reports the photochemical reduction of benzil 1 to benzoin 2 and the reduction of 2 to hydrobenzoin 4 in deoxygenated solvents in the presence of triethylamine (TEA) and/or TiO 2 . Without TEA or TiO 2 , the photolysis of 1 resulted in very low yield of 2. The presence of TEA or TiO 2 increased the rate of disappearance of 1 and the yield of 2, which were further increased considerably by the presence of water. The photoreduction of 1 to 2 proceeds through an electron transfer to 1 from TEA or hole-scavenged excited TiO 2 followed by protonation. In the reaction medium of 88:7:2:3 CH 3 CN/CH 3 OH/H 2 O/TEA with 2.5 mg/mL of TiO 2 , the yield of 2 was as high as 85% at 50% conversion of 1. The photolysis of 2 in homogeneous media resulted in photo-cleavage to benzoyl and hydroxybenzyl radicals, which are mostly converted to benzaldehyde. The reduction product 4 is formed in low yield through the dimerization of hydroxybenzyl radicals. The addition of TEA increased the conversion rate of 2 and the yield of 4 significantly. This was attributed to the scavenging effect of TEA for benzoyl radical to produce N,N-diethylbenzamide and the photoreduction of benzaldehyde in the presence of TEA. The ratio of (±) and meso isomers of 4 obtained from the photochemical reaction is about 1.1. This ratio is the same as that from the photochemical reduction of benzaldehyde in the presence of TEA. In the TiO 2 -sensitized photochemical reduction of 2, meso-4 was obtained in moderate yield. The reduction of 2 to 4 proceeds through two consecutive electron/proton transfer processes on the surface of the photocatalyst without involvement of α-cleavage. The radical 11 initially formed from 2 by one electron/proton process can also combine with hydroxy methyl radical, which is generated after hole trapping of excited TiO 2 by methanol, to product 1,2-diphenylpropenone after dehydration reaction

  8. In situ DRIFTS study of O{sub 3} adsorption on CaO, γ-Al{sub 2}O{sub 3}, CuO, α-Fe{sub 2}O{sub 3} and ZnO at room temperature for the catalytic ozonation of cinnamaldehyde

    Energy Technology Data Exchange (ETDEWEB)

    Wu, Jianfeng; Su, Tongming; Jiang, Yuexiu; Xie, Xinling [School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004 (China); Qin, Zuzeng, E-mail: qinzuzeng@gmail.com [School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004 (China); Ji, Hongbing, E-mail: jihb@mail.sysu.edu.cn [School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004 (China); School of Chemistry, Sun Yat-sen University, Guangzhou 510275 (China)

    2017-08-01

    Highlights: • In situ DRIFTS study of O{sub 3} adsorption on metal oxides at room temperature. • Using acidic probe molecules (DRIFTS) characterization of surface basicity. • Correlation between basic strength of metal oxides and O{sub 3} adsorption. • Study on the competitive adsorption of O{sub 3} and CO{sub 2}. • DRIFTS study of cinnamaldehyde ozonation and benzaldehyde excessive oxidation. - Abstract: In situ DRIFTS were conducted to identify adsorbed ozone and/or adsorbed oxygen species on CaO, ZnO, γ-Al{sub 2}O{sub 3}, CuO and α-Fe{sub 2}O{sub 3} surfaces at room temperature. Samples were characterized by means of TG, XRD, N{sub 2} adsorption–desorption, pyridine-IR, nitrobenzene-IR, chloroform-IR, and CO{sub 2}-TPD. Pyridine-DRIFTS measurements evidence two kinds of acid sites in all the samples. Nitrobenzene, chloroform-DRIFTS, and CO{sub 2}-TPD reveal that there are large amounts of medium-strength base sites on all the metal oxides, and only CaO, ZnO, and γ-Al{sub 2}O{sub 3} have strong base sites. And the benzaldehyde selectivity was increased in the same order of the alkalinity of the metal oxides. With weaker sites, ozone molecules form coordinative complexes bound via the terminal oxygen atom, observed by vibrational frequencies at 2095–2122 and 1026–1054 cm{sup −1}. The formation of ozonide O{sub 3}{sup −} at 790 cm{sup −1}, atomic oxygen at 1317 cm{sup −1}, and superoxide O{sub 2}{sup −} at 1124 cm{sup −1} was detected; these species are believed to be intermediates of O{sub 3} decomposition on strong acid/base sites. The adsorption of ozone on metal oxides is a weak adsorption, and other gases, such as CO{sub 2}, will compete with O{sub 3} adsorption. The mechanism of cinnamaldehyde ozonation at room temperature over CaO shows that cinnamaldehyde can not only be oxidized into cinnamic acid, but also be further oxidized into benzaldehyde, benzoic acid, maleic anhydride, and ultimately mineralized to CO{sub 2} in the

  9. Benzene formation in electronic cigarettes.

    Science.gov (United States)

    Pankow, James F; Kim, Kilsun; McWhirter, Kevin J; Luo, Wentai; Escobedo, Jorge O; Strongin, Robert M; Duell, Anna K; Peyton, David H

    2017-01-01

    The heating of the fluids used in electronic cigarettes ("e-cigarettes") used to create "vaping" aerosols is capable of causing a wide range of degradation reaction products. We investigated formation of benzene (an important human carcinogen) from e-cigarette fluids containing propylene glycol (PG), glycerol (GL), benzoic acid, the flavor chemical benzaldehyde, and nicotine. Three e-cigarette devices were used: the JUULTM "pod" system (provides no user accessible settings other than flavor cartridge choice), and two refill tank systems that allowed a range of user accessible power settings. Benzene in the e-cigarette aerosols was determined by gas chromatography/mass spectrometry. Benzene formation was ND (not detected) in the JUUL system. In the two tank systems benzene was found to form from propylene glycol (PG) and glycerol (GL), and from the additives benzoic acid and benzaldehyde, especially at high power settings. With 50:50 PG+GL, for tank device 1 at 6W and 13W, the formed benzene concentrations were 1.9 and 750 μg/m3. For tank device 2, at 6W and 25W, the formed concentrations were ND and 1.8 μg/m3. With benzoic acid and benzaldehyde at ~10 mg/mL, for tank device 1, values at 13W were as high as 5000 μg/m3. For tank device 2 at 25W, all values were ≤~100 μg/m3. These values may be compared with what can be expected in a conventional (tobacco) cigarette, namely 200,000 μg/m3. Thus, the risks from benzene will be lower from e-cigarettes than from conventional cigarettes. However, ambient benzene air concentrations in the U.S. have typically been 1 μg/m3, so that benzene has been named the largest single known cancer-risk air toxic in the U.S. For non-smokers, chronically repeated exposure to benzene from e-cigarettes at levels such as 100 or higher μg/m3 will not be of negligible risk.

  10. 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..

  11. Characterization of some Pr(III) complexes in terms of electronic spectral parameters

    International Nuclear Information System (INIS)

    Bhati, P.R.; Soni, K.P.; Joshi, G.K.; Swami, S.N.

    1992-01-01

    Pr(III) complexes from the ligands derived from methyl acetoacetate, ethyl acetoacetate, veratraldehyde, ethyl vanillin and 2,5 dimethoxy benzaldehyde forming Schiff-bases with ortho, meta and para phenylene diamines have been synthesized. The complexes have been characterized in terms of various Slater-Condon Lande and Judd-Ofelt parameters. The various trends in the parametric values have also been described. The involvement of 4f-orbital in the Pr(III) complexes including deviation in the symmetry have been discussed on the basis of electronic spectral parameters. The validity of the theories used has been established while comparing observed and calculated energies and intensities of the various bands in the present complexes on the basis of r.m.s deviation. The trends of the curves observed in the solution spectra have also been discussed. (author). 21 refs., 5 tabs., 2 figs

  12. Concentration and trend of 9,10-phenanthrenequinone in airborne particulates collected in Nagasaki city, Japan.

    Science.gov (United States)

    Kishikawa, Naoya; Nakao, Maiko; Ohba, Yoshihito; Nakashima, Kenichiro; Kuroda, Naotaka

    2006-07-01

    9,10-Phenanthrenequinone (PQ), one of the components of atmospheric pollutants, has potent harmful effects on human health. PQ in airborne particulates collected in Nagasaki city was determined by HPLC with fluorescence derivatization. PQ extracted from airborne particulates using methanol was derivatized with benzaldehyde in the presence of ammonium acetate to give a fluorescent compound. The average concentration (mean+/-SD, n=52) of PQ found in airborne particulates collected from July 1997 to June 1998 was 0.287+/-0.128 ng m-3. Concentrations of PQ in winter were higher than those in summer. In a weekly variation study, PQ concentrations were higher during weekdays and lower at weekend. The levels of PQ were obviously correlated with those of phenanthrene (PH) that is considered as a parent compound of PQ. This observation suggested that PQ was emitted into the atmosphere from the same source as PH, or PQ was converted from PH in the atmosphere.

  13. Synthesis, crystal growth and characterization of 1,5-diphenylpenta-1,4-dien-3-one: An organic crystal

    Science.gov (United States)

    Vanchinathan, K.; Bhagavannarayana, G.; Muthu, K.; Meenakshisundaram, S. P.

    2011-11-01

    1,5-Diphenylpenta-1,4-dien-3-one ( dibenzalacetone, DBA) was synthesized by a base-catalyzed aldol condensation reaction between benzaldehyde and acetone. High quality single crystals have been grown by the slow evaporation of ethanol solution and the crystal belongs to monoclinic system with centrosymmetric space group C 2/c. The DBA crystals are transparent in the entire visible region and have a lower optical cutoff at ∼440 nm. It is stable up to 119 °C and has a good chemical stability. The high resolution X-ray diffraction curve (DC) indicates that the specimen is free from structural grain boundaries. Molecular packing leads to a centrosymmetric arrangement resulting in zero second harmonic generation (SHG; χ(2)=0) efficiency.

  14. 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.

  15. Ruthenium(II) hydrazone Schiff base complexes: Synthesis, spectral study and catalytic applications

    Science.gov (United States)

    Manikandan, R.; Viswanathamurthi, P.; Muthukumar, M.

    2011-12-01

    Ruthenium(II) hydrazone Schiff base complexes of the type [RuCl(CO)(B)(L)] (were B = PPh 3, AsPh 3 or Py; L = hydrazone Schiff base ligands) were synthesized from the reactions of hydrazone Schiff base ligand (obtained from isonicotinoylhydrazide and different hydroxy aldehydes) with [RuHCl(CO)(EPh 3) 2(B)] (where E = P or As; B = PPh 3, AsPh 3 or Py) in 1:1 molar ratio. All the new complexes have been characterized by analytical and spectral (FT-IR, electronic, 1H, 13C and 31P NMR) data. They have been tentatively assigned an octahedral structure. The synthesized complexes have exhibited catalytic activity for oxidation of benzyl alcohol to benzaldehyde and cyclohexanol to cyclohexanone in the presence of N-methyl morpholine N-oxide (NMO) as co-oxidant. They were also found to catalyze the transfer hydrogenation of aliphatic and aromatic ketones to alcohols in KOH/Isopropanol.

  16. A catalytic reactor for the trapping of free radicals from gas phase oxidation reactions

    Science.gov (United States)

    Conte, Marco; Wilson, Karen; Chechik, Victor

    2010-10-01

    A catalytic reactor for the trapping of free radicals originating from gas phase catalytic reactions is described and discussed. Radical trapping and identification were initially carried out using a known radical generator such as dicumyl peroxide. The trapping of radicals was further demonstrated by investigating genuine radical oxidation processes, e.g., benzaldehyde oxidation over manganese and cobalt salts. The efficiency of the reactor was finally proven by the partial oxidation of cyclohexane over MoO3, Cr2O3, and WO3, which allowed the identification of all the radical intermediates responsible for the formation of the products cyclohexanol and cyclohexanone. Assignment of the trapped radicals was carried out using spin trapping technique and X-band electron paramagnetic resonance spectroscopy.

  17. Structural Correlation of Some Heterocyclic Chalcone Analogues and Evaluation of Their Antioxidant Potential

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2013-09-01

    Full Text Available A series of six novel heterocyclic chalcone analogues 4(a–f has been synthesized by condensing 2-acetyl-5-chlorothiophene with benzaldehyde derivatives in methanol at room temperature using a catalytic amount of sodium hydroxide. The newly synthesized compounds are characterized by IR, mass spectra, elemental analysis and melting point. Subsequently; the structures of these compounds were determined using single crystal X-ray diffraction. All the synthesized compounds were screened for their antioxidant potential by employing various in vitro models such as DPPH free radical scavenging assay, ABTS radical scavenging assay, ferric reducing antioxidant power and cupric ion reducing antioxidant capacity. Results reflect the structural impact on the antioxidant ability of the compounds. The IC50 values illustrate the mild to good antioxidant activities of the reported compounds. Among them, 4f with a p-methoxy substituent was found to be more potent as antioxidant agent.

  18. Novel fluorescent sensor for silver (I) based on the 3,4-bis-triazole Bodipy via dual-click chemistry

    Science.gov (United States)

    Kursunlu, Ahmed Nuri; Güler, Ersin

    2017-04-01

    This investigation paper relates with a novel dual-Bodipy derivative obtained by using 'click' chemistry. The synthesized compounds were characterized by some techniques as 1H NMR, 13C NMR, 11B-NMR, 19F NMR, FT-IR, Uv-vis, spectrofluorimetry, mass, elemental analysis, melting point. The photophysical measurements were conducted on 4,4-difluoro-8-(4-(3-{8-{3,4-Bis{1,2,3 triazolomethoxy}benzaldehyde)}propoxy))phenyl-4-bora-3a,4a, diaza-s-indacene (Bodipy-T) in presence of different metal ions. General trends were performed for emission, absorption, excitation, complex stoichiometry, different concentrations, competing ion, binding constants etc. in methanolic medium. Bodipy-T can be potentially served as a sensitive and selective ratiometric sensor for Ag (I) ion, moreover, it includes a modifiable group (aldehyde) for the preparing of its new derivatives.

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

    Directory of Open Access Journals (Sweden)

    Guillermo Arrázola

    2012-08-01

    Full Text Available 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 (sweet, slightly bitter or bitter and the genotype (homozygous: sweet or bitter or heterozygous: sweet or slightly bitter with an easy analytical test. Results showed that there was a clear difference in the amount of amygdalin between bitter and non-bitter cultivars. However, the content of amygdalin did not differentiate the other genotypes, since similar amounts of amygdalin can be found in the two different genotypes with the same phenotype

  20. An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

    Directory of Open Access Journals (Sweden)

    Magda A. Abdallah

    2017-08-01

    Full Text Available A new series of pyrazolylpyridines was prepared by reaction of ethyl-3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate with the appropriate aldehyde, malononitrile, or ethyl acetoacetate and an excess of ammonium acetate under reflux in acetic acid. Similarly, two novel bipyridine derivatives were prepared by the above reaction using terephthaldehyde in lieu of benzaldehyde derivatives. In addition, a series of 1,2,4-triazolo[4,3-a]pyrimidines was synthesized by a reaction of 6-(pyrazol-3-ylpyrimidine-2-thione with a number of hydrazonoyl chlorides in dioxane and in the presence of triethylamine. The structure of the produced compounds was established by elemental analyses and spectral methods, and the mechanisms of their formation was discussed. Furthermore, the pyrazolyl-pyridine derivatives were tested as anticancer agents and the results obtained showed that some of them revealed high activity against human hepatocellular carcinoma (HEPG2 cell lines.

  1. (Gold core) at (ceria shell) nanostructures for plasmon-enhanced catalytic reactions under visible light

    KAUST Repository

    Wang, Jianfang

    2014-08-26

    Driving catalytic reactions with sunlight is an excellent example of sustainable chemistry. A prerequisite of solar-driven catalytic reactions is the development of photocatalysts with high solar-harvesting efficiencies and catalytic activities. Herein, we describe a general approach for uniformly coating ceria on monometallic and bimetallic nanocrystals through heterogeneous nucleation and growth. The method allows for control of the shape, size, and type of the metal core as well as the thickness of the ceria shell. The plasmon shifts of the Au@CeO2 nanostructures resulting from the switching between Ce(IV) and Ce(III) are observed. The selective oxidation of benzyl alcohol to benzaldehyde, one of the fundamental reactions for organic synthesis, performed under both broad-band and monochromatic light, demonstrates the visible-light-driven catalytic activity and reveals the synergistic effect on the enhanced catalysis of the Au@CeO2 nanostructures. © 2014 American Chemical Society.

  2. Synthesis of Some New 1,3,4-Thiadiazole, Thiazole and Pyridine Derivatives Containing 1,2,3-Triazole Moiety

    Directory of Open Access Journals (Sweden)

    Nadia A. Abdelriheem

    2017-02-01

    Full Text Available In this study, 1-(5-Methyl-1-(p-tolyl-1H-1,2,3-triazol-4-ylethan-1-one, was reacted with Thiosemicarbazide, alkyl carbodithioate and benzaldehyde to give thiosemicarbazone, alkylidenehydrazinecarbodithioate and 3-phenylprop-2-en-1-one-1,2,3-triazole derivatives. The 1,3,4-thiadiazole derivatives containing the 1,2,3-triazole moiety were obtained via reaction of alkylidenecarbodithioate with hydrazonoyl halides. Also, hydrazonoyl halides were reacted with thiosemicarbazone and pyrazolylthioamide to give 1,3-thiazoles derivatives. Subsequently, 3-phenyl2-en-1-one was used to synthesize substituted pyridines and substituted nicotinic acid ester. The latter was converted to its azide compound which was reacted with aromatic amines and phenol to give substituted urea and phenylcarbamate containing 1,2,3-triazole moiety. The newly synthesized compounds were established by elemental analysis, spectral data and alternative synthesis whenever possible.

  3. Nematicidal activity of plant essential oils and components from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) essential oils against pine wood nematode (Bursaphelenchus xylophilus).

    Science.gov (United States)

    Kim, Junheon; Seo, Sun-Mi; Lee, Sang-Gil; Shin, Sang-Chul; Park, Il-Kwon

    2008-08-27

    Commercial essential oils from 28 plant species were tested for their nematicidal activities against the pine wood nematode, Bursaphelenchus xylophilus. Good nematicidal activity against B. xylophilus was achieved with essential oils of coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii). Analysis by gas chromatography-mass spectrometry led to the identification of 26, 11, and 4 major compounds from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) oils, respectively. Compounds from each plant essential oil were tested individually for their nematicidal activities against the pine wood nematode. Among the compounds, benzaldehyde, trans-cinnamyl alcohol, cis-asarone, octanal, nonanal, decanal, trans-2-decenal, undecanal, dodecanal, decanol, and trans-2-decen-1-ol showed strong nematicidal activity. The essential oils described herein merit further study as potential nematicides against the pine wood nematode.

  4. 1-(2,4-Dihydroxyphenyl)-1-ethanone Hydrazone Derivatives as Notable Butyrylcholinesterase Inhibitors

    International Nuclear Information System (INIS)

    Abbasi, M. A.; Niazi, S. K.; Rehman, A. U.; Siddiqui, S. Z.; Hussain, G.; Rasool, S.

    2016-01-01

    Azomethine group of Schiff bases is known to express valuable biological activities. 1-(2,4-Dihydroxyphenyl)-1-ethanone N'-substituted hydrazone derivatives, 4a-s, were synthesized in multistep. The starting material 2,4-dihydroxyacetophenone (1) was stirred with hydrated hydrazine to yield 1-(2,4-dihydroxyphenyl)-1-ethanone hydrazone (2) which was further reacted with (un)substituted benzaldehydes, 3a-s, to acquire the target molecules, 4a-s. Moreover, the synthesized derivatives 4a-s was characterized via IR, EI-MS, 1H-NMR and 13C-NMR spectral techniques. Most of the compounds were found to be valuable inhibitors of butyrylcholinesterase enzyme. (author)

  5. Solvent-free synthesis of azomethines, spectral correlations and antimicrobial activities of some E-benzylidene-4-chlorobenzenamines

    Directory of Open Access Journals (Sweden)

    R. Suresh

    2015-07-01

    Full Text Available Some azomethines including substituted benzylidene-4-chlorobenzenamines (E-imines have been synthesized by fly-ash: PTS catalyzed microwave assisted condensation of 4-chloroaniline and substituted benzaldehydes under solvent-free conditions. The yield of the imines has been found to be more than 85%. The purity of all imines has been checked using their physical constants and UV, IR and NMR spectral data. These spectral data have been correlated with Hammett substituent constants and F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. The antimicrobial activities of all imines have been studied using standard methods.

  6. Electrocatalytic activity of surface adsorbed ruthenium-alizarin complexone toward the oxidation of benzyl alcohol

    Energy Technology Data Exchange (ETDEWEB)

    Marques, Aldalea Lopes Brandes; Li Weihua; Marques, Edmar Pereira; Zhang Jiujun

    2004-03-01

    The surface electrochemical behavior of an adsorbed alizarin complexone (abbreviated as AC) and its surface coordination with Ru(II) were studied in aqueous solution at a pH range of 0-6. The surface complex of ruthenium with AC displays strong electrocatalytic activities toward benzyl alcohol. Based on the rotating disk electrode measurement, it is believed that the electrocatalytic oxidation of benzyl alcohol is a two-electron and two-proton process with benzaldehyde as a major product. On the other hand, ruthenium-AC surface complex has also shown catalytic activities toward electro-oxidation of several small organic molecules such as methanol, formic acid, formaldehyde, ethanol, and acetaldehyde.

  7. Identification of a phytotoxic photo-transformation product of diclofenac using effect-directed analysis

    Energy Technology Data Exchange (ETDEWEB)

    Schulze, Tobias, E-mail: tobias.schulze@ufz.d [UFZ Helmholtz-Centre for Environmental Research, Department of Effect-Directed Analysis, Permoserstrasse 15, 04318 Leipzig (Germany); Weiss, Sara [UFZ Helmholtz-Centre for Environmental Research, Department of Effect-Directed Analysis, Permoserstrasse 15, 04318 Leipzig (Germany); Fraunhofer Institute of Toxicology and Experimental Medicine, Department of Chemical Risk Assessment, Nikolai-Fuchs-Strasse 1, 30625 Hannover (Germany); Schymanski, Emma; Ohe, Peter Carsten von der [UFZ Helmholtz-Centre for Environmental Research, Department of Effect-Directed Analysis, Permoserstrasse 15, 04318 Leipzig (Germany); Schmitt-Jansen, Mechthild; Altenburger, Rolf [UFZ Helmholtz-Centre for Environmental Research, Department of Bioanalytical Ecotoxicology, Permoserstrasse 15, 04318 Leipzig (Germany); Streck, Georg; Brack, Werner [UFZ Helmholtz-Centre for Environmental Research, Department of Effect-Directed Analysis, Permoserstrasse 15, 04318 Leipzig (Germany)

    2010-05-15

    The pharmaceutical diclofenac (DCF) is released in considerably high amounts to the aquatic environment. Photo-transformation of DCF was reported as the main degradation pathway in surface waters and was found to produce metabolites with enhanced toxicity to the green algae Scenedesmus vacuolatus. We identified and subsequently confirmed 2-[2-(chlorophenyl)amino]benzaldehyde (CPAB) as a transformation product with enhanced toxicity using effect-directed analysis. The EC{sub 50} of CPAB (4.8 mg/L) was a factor of 10 lower than that for DCF (48.1 mg/L), due to the higher hydrophobicity of CPAB (log K{sub ow} = 3.62) compared with DCF (log D{sub ow} = 2.04) at pH 7.0. - Effect-directed analysis of irradiated diclofenac results in the identification of one photo-transformation product responsible for the enhanced toxicity to Scenedesmus vacuolatus.

  8. Molecular Structure, Spectroscopic and DFT Computational Studies of Arylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H-trione

    Directory of Open Access Journals (Sweden)

    Assem Barakat

    2016-09-01

    Full Text Available Reaction of barbituric acid derivatives and di-substituted benzaldehyde in water afforded arylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H-trione derivatives (1 and 2. The one step reaction proceeded efficiently, smoothly, and in excellent yield. The arylidene compounds were characterized by spectrophotometric tools plus X-ray single crystal diffraction technique. Quantum chemical calculations were performed using the DFT/B3LYP method to optimize the structure of the two isomers (1 and 2 in the gas phase. The optimized structures were found to agree well with the experimental X-ray structure data. The highest occupied (HOMO and lowest unoccupied (LUMO frontier molecular orbitals analyses were performed and the atomic charges were calculated using natural populationanalysis.

  9. Potential antisecretory antidiarrheals. 1. Alpha 2-adrenergic aromatic aminoguanidine hydrazones.

    Science.gov (United States)

    Pitzele, B S; Moormann, A E; Gullikson, G W; Albin, D; Bianchi, R G; Palicharla, P; Sanguinetti, E L; Walters, D E

    1988-01-01

    Guanabenz, a centrally acting antihypertensive agent, has been shown to have intestinal antisecretory properties. A series of aromatic aminoguanidine hydrazones was made in an effort to separate the antisecretory and cardiovascular activities. Benzaldehyde, naphthaldehyde, and tetralone derivatives were synthesized. The compounds were evaluated in the cholera toxin treated ligated jejunum of the rat and in the Ussing chamber using a rabbit ileum preparation. A number of compounds, including members of each structural class, were active upon subcutaneous administration in the rat. Active compounds were determined to be alpha 2-adrenergic agonists by yohimbine reversals of their Ussing chamber activities. The compound displaying the best separation of activities was the aminoguanidine hydrazone of 2,6-dimethyl-4-hydroxybenzaldehyde (20).

  10. Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination.

    Science.gov (United States)

    Heinz, Christoph; Lutz, J Patrick; Simmons, Eric M; Miller, Michael M; Ewing, William R; Doyle, Abigail G

    2018-02-14

    This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.

  11. Conducting nanofibres produced by electrospinning

    Science.gov (United States)

    Sen, S.; Davis, F. J.; Mitchell, G. R.; Robinson, E.

    2009-08-01

    Electrospun fibres based on polypyrrole have been prepared. The incorporation of preformed polypyrrole into fibres electrospun from a carrier polymer can only be achieved when materials are prepared with particulates smaller than the cross-section of the fibre; even so there are some problems, with the substantial loss of material from the electrode tip. As an alternative approach, soluble polypyrroles can be prepared but these are not of sufficient viscosity to prepare electrospun fibres, once again a carrier polymer must be employed. More effective loadings are gained by the process of coating the outer surface of a pre-spun fibre; in this way electrospun fibres coated with polypyrrole can be prepared. This approach has been adapted to produce silver coated polymer fibres by the use of copolymers of styrene and 3-vinyl benzaldehyde.

  12. Conducting nanofibres produced by electrospinning

    International Nuclear Information System (INIS)

    Sen, S; Mitchell, G R; Robinson, E; Davis, F J

    2009-01-01

    Electrospun fibres based on polypyrrole have been prepared. The incorporation of preformed polypyrrole into fibres electrospun from a carrier polymer can only be achieved when materials are prepared with particulates smaller than the cross-section of the fibre; even so there are some problems, with the substantial loss of material from the electrode tip. As an alternative approach, soluble polypyrroles can be prepared but these are not of sufficient viscosity to prepare electrospun fibres, once again a carrier polymer must be employed. More effective loadings are gained by the process of coating the outer surface of a pre-spun fibre; in this way electrospun fibres coated with polypyrrole can be prepared. This approach has been adapted to produce silver coated polymer fibres by the use of copolymers of styrene and 3-vinyl benzaldehyde.

  13. Zeolites with isolated-framework and oligomeric-extraframework hafnium species characterized with pair distribution function analysis.

    Science.gov (United States)

    Iida, Takayuki; Ohara, Koji; Román-Leshkov, Yuriy; Wakihara, Toru

    2018-03-28

    Zeolites containing framework heteroatoms (e.g., Ti, Sn, and Hf) with open coordination sites behave as solid-state Lewis acids and exhibit remarkable catalytic properties unachievable with bulk oxides. However, direct evidence confirming the incorporation of such heteroatom species into the zeolite framework is difficult to obtain because of the limited number of analytical methods capable of discerning framework incorporation from extraframework species. In this work, the structural environments of hafnium (Hf) framework and extraframework species added post-synthetically into *BEA zeolites were analyzed using coupled pair distribution function (PDF) and diffuse reflectance (DR) UV-vis measurements. PDF analysis enabled the visualization and identification of framework and extraframework HfO x species, both of which were undetectable by traditional X-ray and neutron diffraction methods. Reactivity data from the aldol condensation of benzaldehyde and acetone confirmed that framework Hf species are responsible for catalytic activity.

  14. Stable Hemiaminals with a Cyano Group and a Triazole Ring

    Directory of Open Access Journals (Sweden)

    Anna Kwiecień

    2014-07-01

    Full Text Available Under neutral conditions the reactions between 4-amino-1,2,4-triazole and cyano-substituted benzaldehyde derivatives yield stable hemiaminals. Addition of small amounts of acid catalyst promotes further step of dehydration resulting in formation of Schiff bases. Four new hemiaminals and the corresponding imines have been obtained. The molecular stability of the hemiaminal intermediates results from both the 1,2,4-triazole moiety and electron withdrawing substituents on the phenyl ring, so no further stabilisation by intramolecular interaction is required. Hemiaminal molecules possess stereogenic centres on carbon and nitrogen atoms. The chirality of these centres is strongly correlated with the conformation of the molecules due to heteroatom hyperconjugation effects.

  15. Enzim Papain: Aspek Green Chemistry pada Reaksi Knoevenagel

    Directory of Open Access Journals (Sweden)

    Laurentius Haryanto

    2015-08-01

    Full Text Available Green chemistry aspect is the chemical approach that has been studied in the past two decades. One of the principles is the development of green synthesis process that is friendly for the environment. This research showed that papain can be used as catalyst for Knoevenagel reaction with 3 kinds of substituted-benzaldehyde and malononitrile as substrates in aqueous medium. The best reaction condition with 80% yield was reached by utilizing of 25 mg papain/mmol substrate. Reaction was conducted at ambient temperature and pressure for 30 min. Products were yellowish to yellow needle crystals and successfully characterized by melting point, UV-Vis, IR, mass spectra, and 13C & 1H-NMR, named as 2-(4-hydroxybenzylidene-malononitrile; 2-(3-hydroxybenzylidene-malononitrile; and 2-(4-hydroxy-3-methoxybenzylidene-malononitrile.

  16. A novel vanadium n-propylamino phosphate catalyst: synthesis, characterization and applications

    Directory of Open Access Journals (Sweden)

    Rajini Anumula

    2012-01-01

    Full Text Available A novel, lamellar type Vanadium n-propylamino phosphate catalyst is synthesized and characterized by using various physicochemical techniques such as Powder X-ray diffraction, Scanning electron microscopy/Energy dispersive X-ray analysis, Thermogravimetry/Differential thermal analysis, Fourier transform Infrared analysis, Electron spin resonance spectroscopy, Ultraviolet - Visible Diffuse reflectance spectroscopy, X-ray Photoelectron spectroscopy, 31P Magic angle spinning Nuclear Magnetic Resonance spectroscopy and Catalytic applications toward Octahydroquinazolinone synthesis. It is found that the n-propylamine is present as sandwich between Vanadyl phosphate layers. Most of the Vanadium is present as V4+ ions in tetrahedral co-ordination. Vanadium n-propylamino phosphate catalyses Octahydroquinazolinone synthesis more effeciently and the optimum conditions required for Octahydroquinazolinone synthesis are, Benzaldehyde (2 mmol, Dimedone (2 mmol, Urea (4 mmol, Methanol + Water (1:1, 5 mL and Catalyst (0.05 g. A plausible mechanism is also proposed.

  17. A novel vanadium n-propylamino phosphate catalyst: synthesis, characterization and applications

    Directory of Open Access Journals (Sweden)

    Rajini Anumula

    2013-02-01

    Full Text Available A novel, lamellar type Vanadium n-propylamino phosphate catalyst is synthesized and characterized by using various physicochemical techniques such as Powder X-ray diffraction, Scanning electron microscopy/Energy dispersive X-ray analysis, Thermogravimetry/Differential thermal analysis, Fourier transform Infrared analysis, Electron spin resonance spectroscopy, Ultraviolet - Visible Diffuse reflectance spectroscopy, X-ray Photoelectron spectroscopy, 31P Magic angle spinning Nuclear Magnetic Resonance spectroscopy and Catalytic applications toward Octahydroquinazolinone synthesis. It is found that the n-propylamine is present as sandwich between Vanadyl phosphate layers. Most of the Vanadium is present as V4+ ions in tetrahedral co-ordination. Vanadium n-propylamino phosphate catalyses Octahydroquinazolinone synthesis more effeciently and the optimum conditions required for Octahydroquinazolinone synthesis are, Benzaldehyde (2 mmol, Dimedone (2 mmol, Urea (4 mmol, Methanol + Water (1:1, 5 mL and Catalyst (0.05 g. A plausible mechanism is also proposed.

  18. Functionalized SBA-15 supported nickel (II)–oxime–imine catalysts for liquid phase oxidation of olefins under solvent-free conditions

    International Nuclear Information System (INIS)

    Paul, Luna; Banerjee, Biplab; Bhaumik, Asim; Ali, Mahammad

    2016-01-01

    A new oxime–imine functionalized highly ordered mesoporous SBA-15 (SBA-15-NH 2 -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(ClO 4 ) 2 to yield the functionalized nickel catalyst SBA-15-NH 2 -DAMO-Ni. All the synthesized materials were thoroughly characterized using different characterization techniques. It was found that SBA-15-NH 2 -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. - Graphical abstract: A new well characterized oxime–imine functionalized highly ordered mesoporous SBA-15-NH 2 -DAMO-Ni complex catalyzes the one-pot oxidation of olefins under solvent free mild conditions.

  19. Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxycarbonyl-3,5-bis(o-methoxyphenyl-4-oxa-cyclohexan-1-ene

    Directory of Open Access Journals (Sweden)

    Vladimir Vinković

    2007-11-01

    Full Text Available Hantzsch condensation of two equivalents of methyl-3-aminocrotonate with (m-and p-methoxybenzaldehyde afforded the expected products 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(m-methoxyphenyl-1,4-dihydropyridine and 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(p-methoxyphenyl-1,4-dihydropyridine, whereas o-methoxy-benzaldehyde produced mainly 1-amino-2-methoxycarbonyl-3,5-bis(o-methoxy-phenyl-4-oxa-cyclohexan-1-ene. The structure of the product, not previously reported in theliterature, was determined by 1D and 2D NMR spectra and its MS fragmentation. This isthe first example of cyclisation leading to a substituted pyran rather than 1,4-DHP undertypical Hantzsch reaction conditions. A plausible mechanism for its formation ispostulated.

  20. 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.

  1. Selectivity control in Pt-catalyzed cinnamaldehyde hydrogenation

    Science.gov (United States)

    Durndell, Lee J.; Parlett, Christopher M. A.; Hondow, Nicole S.; Isaacs, Mark A.; Wilson, Karen; Lee, Adam F.

    2015-01-01

    Chemoselectivity is a cornerstone of catalysis, permitting the targeted modification of specific functional groups within complex starting materials. Here we elucidate key structural and electronic factors controlling the liquid phase hydrogenation of cinnamaldehyde and related benzylic aldehydes over Pt nanoparticles. Mechanistic insight from kinetic mapping reveals cinnamaldehyde hydrogenation is structure-insensitive over metallic platinum, proceeding with a common Turnover Frequency independent of precursor, particle size or support architecture. In contrast, selectivity to the desired cinnamyl alcohol product is highly structure sensitive, with large nanoparticles and high hydrogen pressures favoring C = O over C = C hydrogenation, attributed to molecular surface crowding and suppression of sterically-demanding adsorption modes. In situ vibrational spectroscopies highlight the role of support polarity in enhancing C = O hydrogenation (through cinnamaldehyde reorientation), a general phenomenon extending to alkyl-substituted benzaldehydes. Tuning nanoparticle size and support polarity affords a flexible means to control the chemoselective hydrogenation of aromatic aldehydes. PMID:25800551

  2. The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde

    International Nuclear Information System (INIS)

    Yoon, Hoe Jin; Jung, He In; Kim, Jun Soo; Kim, Kwan Mook; Ahn, Yun Soo; Nandhakumar, Raju

    2012-01-01

    2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde (2) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of 2 was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of 2 with optically pure leucinol. The absolute configuration of the separated enantiomer of 2 was decided from the energy calculation of the corresponding imine diastereomers. The activity of 2 as a chirality conversion reagent (CCR) for amino acids was determined by 1 H NMR analysis. The efficiency of 2 is not better than the previous CCRs based on binaththol. Compound 2, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids

  3. Interaction of oxides of nitrogen and aromatic hydrocarbons under simulated atmospheric conditions

    International Nuclear Information System (INIS)

    Obrien, R.J.; Green, P.J.; Doty, R.A.; Vanderzanden, J.W.; Easton, R.R.; Irwin, R.P.

    1979-01-01

    The reactions of nitrogen oxides with aromatic hydrocarbons under simulated atmospheric conditions are investigated. Gaseous reaction products formed when toluene is irradiated under simulated atmospheric conditions in the presence of nitrogen oxides were analyzed by gas chromatography. Reaction products detected include acetylene, water, acetaldehyde, acetone, toluene, benzaldehyde, ortho-, meta- and para-cresol, benzyl nitrate and meta- and para-nitrotoluene. Reaction mechanisms yielding the various products are illustrated. The assumption that all the nitrogen oxides observed to be lost from the reaction products can be accounted for by nitric acid formation in the absence of ozone formation is verified by a model in which the hydroxyl radical is assumed to be the only means of removing toluene. Under conditions in which ozone is formed, nitrogen oxide loss is accounted for by ozone formation in addition to nitric acid formation

  4. 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).

  5. Bimetallic Cu-Ni nanoparticles supported on activated carbon for catalytic oxidation of benzyl alcohol

    Science.gov (United States)

    Kimi, Melody; Jaidie, Mohd Muazmil Hadi; Pang, Suh Cem

    2018-01-01

    A series of bimetallic copper-nickel (CuNix, x = 0.1, 0.2, 0.5 and 1) nanoparticles supported on activated carbon (AC) were prepared by deposition-precipitation method for the oxidation of benzyl alcohol to benzaldehyde using hydrogen peroxide as oxidising agent. Analyses by means of X-ray Diffraction (XRD) and Scanning Electron Microscopy (SEM) confirmed that Cu and Ni was successfully added on the surface of activated carbon. CuNi1/AC showed the best catalytic activity for the oxidation of benzyl alcohols to the corresponding aldehyde within a short reaction period at 80 °C. The catalytic performance is significantly enhanced by the addition of equal amount of Ni as compared to the monometallic counterpart. This result indicates the synergistic effect between Ni and Cu particles in the catalytic oxidation reaction.

  6. Flavor release from salad dressings: sensory and physicochemical approaches in relation with the structure.

    Science.gov (United States)

    Charles, M; Rosselin, V; Beck, L; Sauvageot, F; Guichard, E

    2000-05-01

    The effect of process and formulation on sensory perception and flavor release was investigated on salad dressing models. Oil/vinegar emulsions (phi = 0.5, droplet size > 10 microm) with thickeners and a whey protein concentrate were prepared with different fat droplet sizes and different distributions of fat droplet size. The effect of the amount of emulsifier was also tested. Sensory profile analysis was performed by a trained panel and flavor release quantified by dynamic headspace analysis. When the droplet size is increased, the lemon smell and citrus aroma significantly increase, whereas the egg note, mustard, and butter aroma significantly decrease. The concentrations of alcohols and acids significantly increase when droplet size increases, whereas those of other compounds such as limonene or benzaldehyde significantly decrease. The dispersion of the droplet size has a small effect on flavor perception, and the effect of the increase of the amount of emulsifier is noticed only by instrumental analysis.

  7. Floral scent of brazilian Passiflora: five species analised by dynamic headspace

    Directory of Open Access Journals (Sweden)

    DANIEL A.V. MONTERO

    2016-01-01

    Full Text Available ABSTRACT This study describes for the first time the chemical composition and olfactive description of floral scent from Brazilian Passiflora (Passiflora edulis Sim, Passiflora alata Curtis, Passiflora cincinnata Mast., Passiflora coccinea Aubl. and Passiflora quadrangularis L.. Five species were grown in greenhouse at the Agronomic Institute (IAC, São Paulo, Brazil. Volatile compounds were collected using dynamic headspace. Analyses of scent composition were performed by gas chromatograph coupled to mass spectrometer. Identification of chemical constituents was conducted through of retention index followed by comparative analysis of mass spectra with specialized databases. The olfactive descriptions of floral scent from each species was evaluated for a professional perfumer. High interspecific diversity was found between chemical compositions of floral scent within Passiflora and different bouquets were observed amount the studied species. Mayor constituents were linalool (P. alata, geraniol (P. quadrangularis, 1,4-dimethoxybenzene (P. edulis, benzaldehyde (P. cincinnata and 2-methyl-3-pentanone (P. coccinea.

  8. Effects of Gamma Irradiation on Active Components in Essential Oils of Cinnamomum verum J.S.Presl

    International Nuclear Information System (INIS)

    Thongphasuk, Piyanuch; Thongphasuk, Jarunee; Eamsiri, Jarurut; Pongpat, Suchada

    2009-07-01

    Full text: Gamma irradiation is one of the methods utilized to reduce microbial contamination of medicinal herbs. Since irradiation may also affect active compounds of the irradiated herbs, the objective of this research is to study the effect of gamma irradiation (10 and 25 kGy) from cobalt-60 on active compounds in essential oils of Cinnamomum verum J.S.Presl by using GC-MS. The results showed that gamma irradiation at the dose of 10 and 25 kGy does not significantly affect active components in essential oils such as alpha-pinene, camphene, 1,8-cineole, alpha-copaene, benzaldehyde, linalool, bornyl acetate, terpinen-4-0l, alpha-terpineol, benzylacetaldehyde, Z-cinnamaldehyde, E-cinnamaldehyde, and cinnamic acid

  9. Inter- and intramolecular aldol reactions promiscuously catalyzed by a proline-based tautomerase.

    Science.gov (United States)

    Rahimi, Mehran; Geertsema, Edzard M; Miao, Yufeng; van der Meer, Jan-Ytzen; van den Bosch, Thea; de Haan, Pim; Zandvoort, Ellen; Poelarends, Gerrit J

    2017-03-28

    The enzyme 4-oxalocrotonate tautomerase (4-OT), which in nature catalyzes a tautomerization step as part of a catabolic pathway for aromatic hydrocarbons, was found to promiscuously catalyze different types of aldol reactions. These include the self-condensation of propanal, the cross-coupling of propanal and benzaldehyde, the cross-coupling of propanal and pyruvate, and the intramolecular cyclizations of hexanedial and heptanedial. Mutation of the catalytic amino-terminal proline (P1A) greatly reduces 4-OT's aldolase activities, whereas mutation of another active site residue (F50A) strongly enhances 4-OT's aldolase activities, indicating that aldolization is an active site process. This catalytic promiscuity of 4-OT could be exploited as starting point to create tailor-made, artificial aldolases for challenging self- and cross-aldolizations.

  10. New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

    Directory of Open Access Journals (Sweden)

    Daily Rodríguez-Padrón

    2017-09-01

    Full Text Available Polysaccharides from natural sources and iron precursors were applied to develop new bio-nanocomposites by mechanochemical milling processes. The proposed methodology was demonstrated to be advantageous in comparison with other protocols for the synthesis of iron oxide based nanostructures. Additionally, mechanochemistry has enormous potential from an environmental point-of-view since it is able to reduce solvent issues in chemical syntheses. The catalytic activity of the obtained nanocatalysts was investigated in both the oxidation of benzyl alcohol to benzaldehyde and in the alkylation of toluene with benzyl chloride. The microwave-assisted oxidation of benzyl alcohol reached 45% conversion after 10 min. The conversion of the alkylation of toluene in both microwave-assisted and conventional heating methods was higher than 99% after 3 min and 30 min, respectively. The transformation of benzyl alcohol and toluene into valuable product in both the oxidation and alkylation reaction reveals a potential method for the valorization of lignocellulosic biomass.

  11. Composition of volatile aromatic compounds and minerals of tarhana enriched with cherry laurel (Laurocerasus officinalis).

    Science.gov (United States)

    Temiz, Hasan; Tarakçı, Zekai

    2017-03-01

    Different concentrations of cherry laurel pulp (0, 5, 10, 15 and 20%) were used to produce tarhana samples. Volatile aromatic compounds and minor mineral content were investigated. Volatile aromatic compounds were analyzed by using GC-MS with SPME fiber and minor mineral values were evaluated with inductively coupled plasma optical emission spectrometer. The statistical analysis showed that addition of pulp affected volatile aromatic compounds and minor mineral content significantly. Thirty five volatile aromatic compounds were found in tarhana samples. The octanoic acid from acids, benzaldehyde (CAS) phenylmethanal from aldehydes, 6-methyl-5-hepten-2-one from ketones, octadecane (CAS) n -octadecane form terpenes, ethyl caprylate from esters and benzenemethanol (CAS) benzyl alcohol from alcohols had the highest percentage of volatile aromatic compounds. Tarhana samples were rich source of Mn, Cu and Fe content.

  12. Synthesis and antiedematogenic activity of some N-tryptophyl-5-benzylidene-2,4-thiazolidinedione and N-tryptophyl-5-benzylidene-rhodanine derivatives; Sintese e atividade antiedematogenica de derivados N-triptofil-5-benzilideno-2,4-tiazolidinadiona e N-triptofil-5-benzilideno-rodanina

    Energy Technology Data Exchange (ETDEWEB)

    Goes, Alexandre Jose da Silva; Lima, Waldir Tavares de; Nagy, Helena Juliana [Pernambuco Univ., Recife, PE (Brazil). Dept. de Antibioticos]. E-mail: ajsg@ufpe.br; Alves, Antonio Jose; Faria, Antonio Rodolfo de; Lima, Jose Gildo de [Pernambuco Univ., Recife, PE (Brazil). Dept. de Ciencias Farmaceuticas; Maia, Maria Bernadete de Souza [Pernambuco Univ., Recife, PE (Brazil). Dept. de Fisiologia e Farmacologia

    2004-12-01

    Derivatives of N tryptophyl-5-benzylidene-2,4-thiazolidinedione (7a-c) and N-tryptophyl-5-benzylidene-rhodanine (7d-f) were prepared by condensation of the intermediates 5 and 6 with different benzaldehydes, respectively. Their structural elucidation was carried through by IR, {sup 1}H NMR and MS. The acute toxicity and antiedematogenic activity of the compounds 7b,c and 7e,f were evaluated. The data did not reveal any sign of toxicity, and no mortality was registered. As indomethacin (10 mg/kg; v.o.), the antiedematogenic activity of the compounds 7b (50 mg/kg; v.o.) and 7e, 7f (50 or 100 mg/kg; v.o.) against carrageenan-induced paw edema was verified at time intervals of 180 min. (author)

  13. Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors.

    Science.gov (United States)

    Zhang, Ting-Jian; Li, Song-Ye; Yuan, Wei-Yan; Wu, Qing-Xia; Wang, Lin; Yang, Su; Sun, Qi; Meng, Fan-Hao

    2017-02-15

    A series of (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesized and identified as novel xanthine oxidase inhibitors. Among them, the most promising compounds 1h and 1k were obtained with IC 50 values of 0.6μM and 0.8μM, respectively, which were more than 10-fold potent compared with allopurinol. The Lineweaver-Burk plot revealed that compound 1h acted as a mixed-type xanthine oxidase inhibitor. SAR analysis showed that the benzaldehyde moiety played a more important role than the anthraquinone moiety for inhibition potency. The basis of significant inhibition of xanthine oxidase by 1h was rationalized by molecular modeling studies. Copyright © 2017 Elsevier Ltd. All rights reserved.

  14. Structure-biological activity relationship of synthetic trihydroxilated chalcones

    Directory of Open Access Journals (Sweden)

    Devia Cristina M.

    1998-01-01

    Full Text Available The bacteriostatic activity of 2?,4?,2-trihydroxychalcone; 2?,4?,3-trihydroxychalcone and 2?,4?,4-trihydroxychalcone, prepared by condensation of 2,4-dihydroxyacetophenone and benzaldehyde substituted, against Staphylococcus aureus ATCC 25923 was assayed by agar plate method. The three compounds presented important inhibition halos. In order to elucidate structure-activity relationships, the minimal inhibitory concentrations against S. aureus were determined by the broth dilution method and the results obtained were compared to that of 2',4'-dihydroxychalcone. The sequence observed was: MIC 2?,4?,3-(OH3 > MIC 2?,4?-(OH2 > MIC 2?,4?,4-(OH3 > > MIC 2?,4?,2-(OH3. These results showed that the introduction of an electron donating group (-OH in the aromatic B-ring causes an increase in bioactivity, and that the intensity of action depends on the position of the OH substitute.

  15. 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.

  16. Synthesis, crystal growth and studies on non-linear optical property of new chalcones

    Science.gov (United States)

    Sarojini, B. K.; Narayana, B.; Ashalatha, B. V.; Indira, J.; Lobo, K. G.

    2006-09-01

    The synthesis, crystal growth and non-linear optical (NLO) property of new chalcone derivatives are reported. 4-Propyloxy and 4-butoxy benzaldehydes were made to under go Claisen-Schmidt condensation with 4-methoxy, 4-nitro and 4-phenoxy acetophenones to form corresponding chalcones. The newly synthesized compounds were characterized by analytical and spectral data. The Second harmonic generation (SHG) efficiency of these compounds was measured by powder technique using Nd:YAG laser. Among tested compounds three chalcones showed NLO property. The chalcone 1-(4-methoxyphenyl)-3-(4-propyloxy phenyl)-2-propen-1-one exhibited SHG conversion efficiency 2.7 times that of urea. The bulk crystal of 1-(4-methoxyphenyl)-3-(4-butoxyphenyl)-2-propen-1-one (crystal size 65×28×15 mm 3) was grown by slow-evaporation technique from acetone. Microhardness of the crystal was tested by Vicker's microhardness method.

  17. Synthesis of new chalcone derivatives and their antimicrobial studies

    Science.gov (United States)

    Noorulhaq, Syed Shah Najib; Baseer, Mohammad Abdul

    2017-11-01

    Chalcones are the significant constituent of natural sources. Chalcones posses 1,3-diaryl-1-ones frame which withdraws the recognition of biological importance. Chalcones are not possible to separate from plants because it is transformed into flavonones due to the presence of enzyme chalcone synthetase. Chalcones are prepared by the Claisen-Schimdt condensation of equimolar ratios of aldehyde and ketone in presence of base. With this vision we accounted here the synthesis of some novel chalcones via Clasien-Schimdt condensation of substituted ketones containing hydroxy, chloro, fluoro groups and 4-(4-Methyl-piperazin-1-yl)-benzaldehyde in presence of alkali at room temperature. These recently synthesized γ, β unsaturated compounds that is chalcones were screened for their antimicrobial studies which show modest to good activity.

  18. Design, synthesis, and spectroscopic study of some new flavones containing two azo linkages

    Science.gov (United States)

    Ayoob, Mzgin Mohammed; Hawaiz, Farouq Emam

    2017-09-01

    In the present study; 5-(4-chlorophenyl azo) -2-hydroxy acetophenone (1) was prepared by diazotization of 4-chloro aniline and its coupling reaction with 2-hydroxy acetophenone, then reacted with different azo benzyloxy benzaldehydes(3a-i) to give new synthesized 2-hydroxy chalcones(4a-i). The later compounds were subjected to oxidative cyclization by catalytic amount of I2 in DMSO affording the target molecules new flavones bearing two azo-linkages (5a-i). The structures of the newly synthesized compounds were identified on the bases of their FT-IR, 1H-NMR, 13C-NMR and DEPT-135 spectra. The synthesized Flavone derivatives were evaluated against two types of bacteria gram positive (Staphylococcus aurous) and gram negative (Pseudomonas aeruginosa). The results showed that most of the synthesized flavones are more sensitive against (G -ve) bacteria than (G +ve) bacteria.

  19. Synthesis and Cytotoxicity of Chalcones and 5-Deoxyflavonoids

    Directory of Open Access Journals (Sweden)

    Jing Zhang

    2013-01-01

    Full Text Available Chalcones 1~8 and 5-deoxyflavonoids 9~22 were synthesized in good yields by aldol condensation, Algar-Flynn-Oyamada reaction, glycosidation, and deacetylation reaction, respectively, starting from 2-acetyl phenols substituted by methoxy or methoxymethoxy group and appropriately benzaldehydes substituted by methoxy, methoxymethoxy group, or chlorine. Among them, 13 and 17~22 are new compounds. The cytotoxicity bioassays of these chalcones and 5-deoxyflavonoids were screened using the sulforhodamine B (SRB protein staining method, and the results showed that compounds 2, 4, 5, 6, 10, 15, and 19 exhibited moderate cytotoxicity against the cancer cell line of MDA-MB-231, U251, BGC-823, and B16 in comparison with control drugs (HCPT, Vincristine, and Taxol.

  20. Myoglobin-Catalyzed Olefination of Aldehydes.

    Science.gov (United States)

    Tyagi, Vikas; Fasan, Rudi

    2016-02-12

    The olefination of aldehydes constitutes a most valuable and widely adopted strategy for constructing carbon-carbon double bonds in organic chemistry. While various synthetic methods have been made available for this purpose, no biocatalysts are known to mediate this transformation. Reported herein is that engineered myoglobin variants can catalyze the olefination of aldehydes in the presence of α-diazoesters with high catalytic efficiency (up to 4,900 turnovers) and excellent E diastereoselectivity (92-99.9 % de). This transformation could be applied to the olefination of a variety of substituted benzaldehydes and heteroaromatic aldehydes, also in combination with different alkyl α-diazoacetate reagents. This work provides a first example of biocatalytic aldehyde olefination and extends the spectrum of synthetically valuable chemical transformations accessible using metalloprotein-based catalysts. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. (E)-Ethyl 2-cyano-3-[5-nitro-2-(pyrrolidin-1-yl)phen-yl]acrylate.

    Science.gov (United States)

    Yapo, Yapi Marcellin; Abou, Bakary Coulibaly; Adjou, Ané; Kakou-Yao, Rita; Tenon, Jules A

    2010-09-04

    The title compound, C(16)H(17)N(3)O(4), was prepared by the reaction of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde and ethyl cyano-acetate. The mol-ecular structure adopts an E conformation with respect to the C=C double bond. The five-membered ring has a half-chair conformation, with puckering parameters Q(2)= 0.399 (2) Å and ϕ = 93.1 (3)°. In the crystal, inversion dimers , linked by pairs of C-H⋯O inter-actions, are further connected through C-H⋯N hydrogen bonds. Weak slipped π-π inter-actions occur between symmetry-related benzene rings [centroid-centroid distance = 3.785 (1)Å].

  2. (E)-Ethyl 2-cyano-3-[5-nitro-2-(pyrrolidin-1-yl)phen­yl]acrylate

    Science.gov (United States)

    Yapo, Yapi Marcellin; Abou, Bakary Coulibaly; Adjou, Ané; Kakou-Yao, Rita; Tenon, Jules A.

    2010-01-01

    The title compound, C16H17N3O4, was prepared by the reaction of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde and ethyl cyano­acetate. The mol­ecular structure adopts an E conformation with respect to the C=C double bond. The five-membered ring has a half-chair conformation, with puckering parameters Q(2)= 0.399 (2) Å and ϕ = 93.1 (3)°. In the crystal, inversion dimers , linked by pairs of C—H⋯O inter­actions, are further connected through C—H⋯N hydrogen bonds. Weak slipped π-π inter­actions occur between symmetry-related benzene rings [centroid–centroid distance = 3.785 (1)Å]. PMID:21587494

  3. Camphor-10-sulfonic acid catalyzed condensation of 2-naphthol with aromatic/aliphatic aldehydes to 14-aryl/alkyl-14H-dibenzo[a,j]xanthenes

    Directory of Open Access Journals (Sweden)

    Kundu Kshama

    2014-01-01

    Full Text Available (±-Camphor-10-sulfonic acid (CSA catalyzed condensation of 2-naphthol with both aliphatic/aromatic aldehydes at 80°C yielded 14-alkyl/aryl-dibenzoxanthenes as the sole product in high yields. However, the same condensation with benzaldehyde at 25°C afforded a mixture of intermediate 1,1-bis-(2-hydroxynaphthylphenylmethane and 14-phenyl-dibenzoxanthene while the condensation with aliphatic aldehydes at 25°C furnished the corresponding 14-alkyl-dibenzoxanthenes as the sole product. Moreover, condensation of 2-naphthol with aromatic/aliphatic aldehydes with low catalyst loading (2 mol% was greatly accelerated under microwave irradiation to afford the corresponding 14-aryl/alkyl-dibenzoxanthenes as the sole product in high yields.

  4. Modulating Crystallinity of Graphitic Carbon Nitride for Photocatalytic Oxidation of Alcohols.

    Science.gov (United States)

    Zhou, Min; Yang, Pengju; Yuan, Rusheng; Asiri, Abdullah M; Wakeel, Muhammad; Wang, Xinchen

    2017-11-23

    Exploiting efficient photocatalysts with strengthened structure for solar-driven alcohol oxidation is of great significance. The photocatalytic performance of graphitic carbon nitrides can be considerably promoted by modulating its crystallinity. Results confirmed that a high crystallinity accelerates the separation and transfer of photogenerated charge carriers, thus providing more free charges for photoredox reactions. More importantly, the high crystallinity facilitated the adsorption of benzyl alcohol and desorption of benzaldehyde and simultaneously lowered the energy barrier for O 2 activation. As a result, the crystalline carbon nitride exhibited a roughly twelvefold promotion with respect to the normal carbon nitride. The remarkable enhancement of activity can be attributed to the synergistic effects of increased electron-hole separation and increased surface reaction kinetics. These findings will open up new opportunities to modulate the structure of polymers for a wide variety of organic reactions. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. Síntese e atividade antiedematogênica de derivados N-triptofil-5-benzilideno-2,4-tiazolidinadiona e N-triptofil-5-benzilideno-rodanina Synthesis and antiedematogenic activity of some N-trypthophyl-5-benzylidene-2,4-thiazolidinedione and N-trypthophyl-5-benzylidene-rhodanine derivatives

    Directory of Open Access Journals (Sweden)

    Alexandre José da Silva Góes

    2004-12-01

    Full Text Available Derivatives of N-tryptophyl-5-benzylidene-2,4-thiazolidinedione (7a-c and N-tryptophyl-5-benzylidene-rhodanine (7d-f were prepared by condensation of the intermediates 5 and 6 with different benzaldehydes, respectively. Their structural elucidation was carried through by IR, ¹H NMR and MS. The acute toxicity and antiedematogenic activity of the compounds 7b,c and 7e,f were evaluated. The data did not reveal any sign of toxicity, and no mortality was registered. As indomethacin (10 mg/kg; v.o., the antiedematogenic activity of the compounds 7b (50 mg/kg; v.o. and 7e, 7f (50 or 100 mg/kg; v.o. against carrageenan-induced paw edema was verified at time intervals of 180 min.

  6. Comparison of the volatile composition of Stachys pubescence oils obtained by hydro distillation and steam distillation.

    Science.gov (United States)

    Biglar, Mahmoud; Ardekani, Mohammad Reza Shams; Khanavi, Mahnaz; Shafiee, Abbas; Rustaiyan, Abdolhossein; Salimpour, Fahimeh; Farjadmand, Fatemeh

    2014-07-01

    The oils obtained by hydrodistillation and steam distillation of the aerial part of Stachys pubescence Ten. was analyzed by GC and GC/MS. Water distilled essential oil of the aerial part of S. pubescence, was rich in fatty acids like hexadecanoic acid and linoleic acid and also benzaldehyde and spathulenol whereas the steam distilled oil of the plant contained hexadecanoic acid, spathulenol and eugenol. Both of oils were rich in fatty acids (36.6 and 27.9%, respectively). Moreover, the content of oxygenated mono and sesquiterpenss were defined higher in steam distilled oil than hydrodistiledd oil (24.5, 17.2 and 6.1, 15.5%, respectively). In conclusion it seems that oxygenated terpenoids were trended to steam distillation method more than hydrodistillation, respectively.

  7. Floral scent of brazilian Passiflora: five species analised by dynamic headspace.

    Science.gov (United States)

    Montero, Daniel A V; Marques, Marcia Ortiz M; Meletti, Laura M M; Kampen, Maria H VAN; Polozzi, Sandra C

    2016-09-01

    This study describes for the first time the chemical composition and olfactive description of floral scent from Brazilian Passiflora (Passiflora edulis Sim, Passiflora alata Curtis, Passiflora cincinnata Mast., Passiflora coccinea Aubl. and Passiflora quadrangularis L.). Five species were grown in greenhouse at the Agronomic Institute (IAC), São Paulo, Brazil. Volatile compounds were collected using dynamic headspace. Analyses of scent composition were performed by gas chromatograph coupled to mass spectrometer. Identification of chemical constituents was conducted through of retention index followed by comparative analysis of mass spectra with specialized databases. The olfactive descriptions of floral scent from each species was evaluated for a professional perfumer. High interspecific diversity was found between chemical compositions of floral scent within Passiflora and different bouquets were observed amount the studied species. Mayor constituents were linalool (P. alata), geraniol (P. quadrangularis), 1,4-dimethoxybenzene (P. edulis), benzaldehyde (P. cincinnata) and 2-methyl-3-pentanone (P. coccinea).

  8. Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes.

    Science.gov (United States)

    Vale, João R; Rimpiläinen, Tatu; Sievänen, Elina; Rissanen, Kari; Afonso, Carlos A M; Candeias, Nuno R

    2018-02-16

    The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.

  9. Hydrazine determination in presence of uranium by modified spectrophotometric method

    International Nuclear Information System (INIS)

    Velavendan, P.; Pandey, N.K.; Kamachi Mudali, U.; Natarajan, R.

    2011-01-01

    In the present work an indirect, sensitive and accurate method for the determination of hydrazine is described. The method is based on the formation of yellow coloured azine complex by post column derivatization of hydrazine with P-dimethylamino benzaldehyde. The formed yellow coloured complex is stable in acidic medium and has a maximum absorption at 460 nm. Interference due to uranium was studied and the method was applied for the determination of hydrazine in presence of uranium in aqueous stream of nuclear fuel reprocessing. A calibration graph was made for the concentration range of hydrazine from 0.05 ppm to 10 ppm with RSD 0.807% and correlation coefficient of 0.99996. (author)

  10. 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. Copyright © 2013 Elsevier Ltd. All rights reserved.

  11. Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis.

    Directory of Open Access Journals (Sweden)

    Somchai Rice

    Full Text Available Recent U.S. legislation permitting recreational use of marijuana in certain states brings the use of marijuana odor as probable cause for search and seizure to the forefront of forensic science, once again. This study showed the use of solid-phase microextraction with multidimensional gas chromatography--mass spectrometry and simultaneous human olfaction to characterize the total aroma of marijuana. The application of odor activity analysis offers an explanation as to why high volatile chemical concentration does not equate to most potent odor impact of a certain compound. This suggests that more attention should be focused on highly odorous compounds typically present in low concentrations, such as nonanal, decanol, o-cymene, benzaldehyde, which have more potent odor impact than previously reported marijuana headspace volatiles.

  12. Volatile oils from the aerial parts of Eremophila maculata and their antimicrobial activity.

    Science.gov (United States)

    Youssef, Fadia S; Hamoud, Razan; Ashour, Mohamed L; Singab, Abdel Nasser; Wink, Michael

    2014-05-01

    The essential oils isolated from the fresh flowers, fresh leaves, and both fresh and air-dried stems of Eremophila maculata (Scrophulariaceae) were characterized by GC-FID and GC/MS analyses. Sabinene was the major component in most of the oils, followed by limonene, α-pinene, benzaldehyde, (Z)-β-ocimene, and spathulenol. The leaf and flower essential oils showed antibacterial and antifungal activity against five Gram-positive and four Gram-negative bacterial strains, multi-resistant clinical isolates from patients, i.e., methicillin-resistant Staphylococcus aureus (MRSA), as well as two yeasts. Minimum inhibitory concentrations (MICs) and minimum microbicidal concentrations (MMCs) were between 0.25 and 4 mg/ml. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.

  13. Responses of the L5178Y mouse lymphoma cell forward mutation assay. V: 27 coded chemicals

    Energy Technology Data Exchange (ETDEWEB)

    McGregor, D.B.; Brown, A.G.; Howgate, S.; McBride, D.; Riach, C. (Inveresk Research International Limited, Musselburgh (Scotland)); Caspary, W.J. (National Inst. of Health, Research Triangle Park, NC (United States))

    1991-01-01

    Twenty-seven chemicals were tested for their mutagenic potential in the L5178Y tk{sup +}/tk{sup {minus}} mouse lymphoma cell forward mutation assay. Cultures were exposed to the chemicals for 4 hr, then cultured for 2 days before plating in soft agar with or without trifluorothymidine (TFT), 3 {mu}g/ml. The chemicals were tested at least twice. Statistically significant responses were obtained with acid orange 10, aniline, benzaldehyde o-chloroaniline, chlorodibromomethane, cytembena, 1,2-dibromo-4-(1,2-dibromomethyl) cyclohexane, dieldrin, lithocholic acid, oxytetracycline, phenazopyridine HCl, 1phenyl-3-methyl-5-pyrazolone, sodium diethyldithiocarbamate, solvent yellow 14, tetraethylthiuram disulfide (disulfiram), 2,4-toluene diisocyanate, and 2,6-toluene diisocyanate. Apart from phenazopyridine HCl, acid orange 10, and solvent yellow 14, rat liver S9 mix was not a requirement for the mutagenic activity of these compounds.

  14. Síntesis y actividad antimicrobiana de derivados de 4,6-diaminopirimidinas análogos de citosina

    Directory of Open Access Journals (Sweden)

    Gricela Lobo

    2012-09-01

    Full Text Available A new synthesis of novel 4,6-diaminopyrimidines 2a-j, cytosine analogous, is described. This involves the base-assisted cyclization reaction of benzylidenemalononitriles 1a-j (BMNs with urea. Compounds 1a-j were prepared by a Knoevenagel condensation reaction from benzaldehyde and malononitrile using EtOH as solvent at room temperature conditions. The antimicrobial activity against Gram-positive microorganisms: Staphylococcus aureus (ATCC 25923 and Bacillus cereus (ATCC 14579 and Gram-negative: Escherichia coli (ATCC 35218 and Pseudomonas aeruginosa (ATCC 27853 and th yeast Candida tropicalis (MLDM 372 is also reported. The compounds 2c, 2e, 2f, 2g, 2i and 2j are considered wide spectrum. Antimicrobial activity, Benzylidenemalononitriles (BMNs, Cytosine, Diaminopyrimidine, Urea,

  15. Eco-Friendly Synthesis and Antiproliferative Evaluation of Some Oxygen Substituted Diaryl Ketones

    Directory of Open Access Journals (Sweden)

    Jaime A. Valderrama

    2013-08-01

    Full Text Available A broad variety of oxygen-substituted diaryl ketones has been synthesized by solar energy-induced Friedel Crafts acylations of 1,4-benzo- and 1,4-naphthoquinones with benzaldehydes. The in vitro antiproliferative properties of the photoproducts were assessed on prostate (DU-145, bladder (T24 and breast (MCF7 human-derived tumor cell lines and compared to non-tumor mouse fibroblasts (Balb/3T3. Among the tested compounds, it was found that those containing a 3,4,5-trimethoxyphenyl A-ring, such as 12 and 22 are more active on DU-145, with EC50 values of 1.2 and 5.9 μM, respectively. By comparing their effects on the three cancer cell lines, the analogue 22 has the best mean selective index (2.4.

  16. ALÉM DA CAIPIRINHA: CACHAÇA COMO SOLVENTE PARA SÍNTESE ORGÂNICA E EXTRAÇÃO DE PIGMENTO

    Directory of Open Access Journals (Sweden)

    Silvio Cunha

    Full Text Available Cachaça (brazilian sugarcane spirit was applied for the first time as an alternative solvent in undergraduate experiments of organics synthesis, and natural dye extraction. The classical Claisen-Schmidt condensation of benzaldehyde with acetophenone and with acetone were employed to demonstrate the cachaça viability as solvent. Cachaça was also the recrystallization solvent of obtained benzalacetophenone and dibenzalacetone. The natural pigment of urucum (Bixa orellana L. was obtained using as extractor solvent a 5% NaOH solution in cachaça. Considering that in Brazil cachaça is easily available and cheaper than the 40% mixture of ethanol/water, it can be found in every marketplace and is exported to 54 countries, the cachaça use as solvent is viable and attractive to green chemistry experiments in undergraduate courses, in Brazil and abroad.

  17. [Mechanism and performance of styrene oxidation by O3/H2O2].

    Science.gov (United States)

    He, Jue-Cong; Huang, Qian-Ru; Ye, Qi-Hong; Luo, Yu-Wei; Zhang, Zai-Li; Fan, Qing-Juan; Wei, Zai-Shan

    2013-10-01

    It can produce a large number of free radicals in O3/H2O2, system, ozone and free radical coupling oxidation can improve the styrene removal efficiency. Styrene oxidation by O3/H2O2 was investigated. Ozone dosage, residence time, H2o2 volume fraction, spray density and molar ratio of O3/C8H8 on styrene removal were evaluated. The experimental results showed that styrene removal efficiency achieved 85.7%. The optimal residence time, H2O2, volume fraction, spray density and O3/C8H8 molar ratio were 20. 6 s, 10% , 1.72 m3.(m2.h)-1 and 0.46, respectively. The gas-phase degradation intermediate products were benzaldehyde(C6H5CHO) and benzoic acid (C6H5 COOH) , which were identified by means of gas chromatography-mass spectrometry(GC-MS). The degradation mechanism of styrene is presented.

  18. Donor/Acceptor-Stabilized 1-Silaketene: Reversible [2+2] Cycloaddition with Pyridine and Evolution by an Olefin Metathesis Reaction.

    Science.gov (United States)

    Reyes, Morelia Lopez; Troadec, Thibault; Rodriguez, Ricardo; Baceiredo, Antoine; Saffon-Merceron, Nathalie; Branchadell, Vicenç; Kato, Tsuyoshi

    2016-07-11

    The reaction of silacyclopropylidene 1 with benzaldehyde generates a 1-silaketene complex 2 by a formal atomic silicon insertion into the C=O bond of the aldehyde. The highly reactive 1-silaketene 2 undergoes a reversible [2+2] cycloaddition with pyridine to give sila-β-lactam 3. Of particular interest, in the presence of 4-dimethylaminopyridine (DMAP), 1-silaketene complex 2 evolves through an intramolecular olefin metathesis reaction, generating a new 1-silaketene complex 8 and cis-stilbene. Theoretical studies suggest that the reaction proceeds through the formation of a transient silacyclobutanone, a four-membered-ring intermediate, similar to that proposed by Chauvin and co-workers for the transition-metal-based olefin metathesis. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance.

    Science.gov (United States)

    Li, Lin-Zhen; Wang, Meng-Hua; Sun, Jian-Bo; Liang, Jing-Yu

    2014-01-01

    Eleven compounds, including four flavonoids [(2R,3R)-2,3-dihydro-3,5-dihydroxy-7,4'-dimethoxyflavone (1), 5-hydroxy-7,8,4'-trimethoxy-flavone (2), amentoflavone (10) and apigenin (11)], two penylpropanoids [sinapaldehyde (3) and 3-methoxy-4-hydroxy-cinnamic aldehyde (4)], three phenolic acids [4-hydroxyl-3,5-dimethoxy-benzaldehyde (5), 4-hydroxyacetophen-one (6) and p-hydroxybenzaldehyde (7)], one furan derivative [5-hydroxymethyl furfural (8)] and one steroid saponin [β-sitosterol-3-O-β-d-glucoside (9)], were isolated and identified from Aletris spicata. Among them, compounds 1-7, 9 and 10 were reported from the genus Aletris for the first time. Furthermore, seven of them (1-6, 10) were obtained from the family Liliaceae for the first time. Chemotaxonomy of the isolated compounds is discussed briefly.

  20. Aromatic aldehydes at the active site of aldehyde oxidoreductase from Desulfovibrio gigas: reactivity and molecular details of the enzyme-substrate and enzyme-product interaction.

    Science.gov (United States)

    Correia, Hugo D; Marangon, Jacopo; Brondino, Carlos D; Moura, Jose J G; Romão, Maria J; González, Pablo J; Santos-Silva, Teresa

    2015-03-01

    Desulfovibrio gigas aldehyde oxidoreductase (DgAOR) is a mononuclear molybdenum-containing enzyme from the xanthine oxidase (XO) family, a group of enzymes capable of catalyzing the oxidative hydroxylation of aldehydes and heterocyclic compounds. The kinetic studies reported in this work showed that DgAOR catalyzes the oxidative hydroxylation of aromatic aldehydes, but not heterocyclic compounds. NMR spectroscopy studies using (13)C-labeled benzaldehyde confirmed that DgAOR catalyzes the conversion of aldehydes to the respective carboxylic acids. Steady-state kinetics in solution showed that high concentrations of the aromatic aldehydes produce substrate inhibition and in the case of 3-phenyl propionaldehyde a suicide substrate behavior. Hydroxyl-substituted aromatic aldehydes present none of these behaviors but the kinetic parameters are largely affected by the position of the OH group. High-resolution crystallographic structures obtained from single crystals of active-DgAOR soaked with benzaldehyde showed that the side chains of Phe425 and Tyr535 are important for the stabilization of the substrate in the active site. On the other hand, the X-ray data of DgAOR soaked with trans-cinnamaldehyde showed a cinnamic acid molecule in the substrate channel. The X-ray data of DgAOR soaked with 3-phenyl propionaldehyde showed clearly how high substrate concentrations inactivate the enzyme by binding covalently at the surface of the enzyme and blocking the substrate channel. The different reactivity of DgAOR versus aldehyde oxidase and XO towards aromatic aldehydes and N-heterocyclic compounds is explained on the basis of the present kinetic and structural data.

  1. Production of allyl phenyl carbinol (APC by biotrans-formation using Rhizopus arrhizus

    Directory of Open Access Journals (Sweden)

    Vilas B. Shukla

    2000-01-01

    Full Text Available The objective of the present work was to study the stereoselective synthesis of homo-allylic alcohol using stereoselective hydrolysis by Rhizopus arrhizus and also to study the stereoselective synthesis of allyl phenyl carbinol (APC or 1-Phenyl-3-butene-1-o by combination of chemical synthesis and biotransformation from cheap raw materials such as benzaldehyde and allyl bromide. Stereospecific synthesis of allyl phenyl carbinol (APC was achieved by acetate hydrolysis by R. arrhizus giving R (+ enantiomer. Maximum enantiomeric excess of APC was obtained at 16 h where as maximum yield of it was obtained at 48 h of biotransformation.O objetivo deste trabalho foi estudar a síntese estereo-seletiva do álcool homo-allylico usando hidrólise estereo-seletiva pelo Rhizopus arrhizus e também estudar a síntese estereo-seletiva do allyl phenyl carbinol (APC ou 1-Phenyl-3-butene- 1-o pela combinação da síntese química e biotransformação dos materiais brutos e baratos, tais como; benzaldehyde and allyl bromide. A síntese Stereospecifica do allyl phenyl carbinol (APC foi conseguida pela hidrólise de acetato pelo R. arrhizus fornecendo enantiomero R (+. O excesso máximo do enantiomérico do APC foi obtido em 16 h sendo que seu rendimento máximo foi obtido após 48 h de biotransformação.

  2. Development of a simple field test for vehicle exhaust to detect illicit use of dyed diesel fuel.

    Science.gov (United States)

    Harvey, Scott D; Wright, Bob W

    2011-10-30

    Tax-free diesel fuel is intended for off-road uses such as agricultural operations, but illicit use of this fuel does occur and is a convenient way of evading payment of excise taxes. Current enforcement to prevent this practice involves visual inspection for the red azo dye added to the fuel to indicate its tax-free status. This approach, while very effective, has shortcomings such as the invasive nature of the tests and/or various deceptive tactics applied by tax evaders. A test designed to detect illicit dyed-fuel use by analyzing the vehicle exhaust would circumvent these shortcomings. This paper describes the development of a simple color spot test designed to detect the use of tax-free (i.e., dyed) fuel by analyzing the engine exhaust. Development efforts first investigated the combustion products of C.I. Solvent Red 164 (the azo dye formulation used in the United States to tag tax-free fuel). A variety of aryl amines were identified as characteristic molecular remnants that appear to survive combustion. A number of micro-analytical color tests specific for aryl amines were then investigated. One test that detected aryl amines by reacting with 4-(dimethylamino)benzaldehyde seemed to be particularly applicable and was used in a proof-of-principle experiment. The 4-(dimethylamino)benzaldehyde color spot test was able to clearly distinguish between engines that were burning regular fuel and those that were burning dyed diesel fuel. Further development will refine this color spot test to provide an easy-to-use field test. Copyright © 2011 Elsevier B.V. All rights reserved.

  3. The volatile profiles of a rare apple (Malus domestica Borkh.) honey: shikimic acid-pathway derivatives, terpenes, and others.

    Science.gov (United States)

    Kuś, Piotr Marek; Jerković, Igor; Tuberoso, Carlo Ignazio Giovanni; Šarolić, Mladenka

    2013-09-01

    The volatile profiles of rare Malus domestica Borkh. honey were investigated for the first time. Two representative samples from Poland (sample I) and Spain (sample II) were selected by pollen analysis (44-45% of Malus spp. pollen) and investigated by GC/FID/MS after headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE). The apple honey is characterized by high percentage of shikimic acid-pathway derivatives, as well as terpenes, norisoprenoids, and some other compounds such as coumaran and methyl 1H-indole-3-acetate. The main compounds of the honey headspace were (sample I; sample II): benzaldehyde (9.4%; 32.1%), benzyl alcohol (0.3%; 14.4%), hotrienol (26.0%, 6.2%), and lilac aldehyde isomers (26.3%; 1.7%), but only Spanish sample contained car-2-en-4-one (10.2%). CH2 Cl2 and pentane/Et2 O 1 : 2 (v/v) were used for USE. The most relevant compounds identified in the extracts were: benzaldehyde (0.9-3.9%), benzoic acid (2.0-11.2%), terpendiol I (0.3-7.4%), coumaran (0.0-2.8%), 2-phenylacetic acid (2.0-26.4%), methyl syringate (3.9-13.1%), vomifoliol (5.0-31.8%), and methyl 1H-indole-3-acetate (1.9-10.2%). Apple honey contained also benzyl alcohol, 2-phenylethanol, (E)-cinnamaldehyde, (E)-cinnamyl alcohol, eugenol, vanillin, and linalool that have been found previously in apple flowers, thus disclosing similarity of both volatile profiles. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

  4. Ligand-tailored single-site silica supported titanium catalysts: Synthesis, characterization and towards cyanosilylation reaction

    Energy Technology Data Exchange (ETDEWEB)

    Xu, Wei; Li, Yani; Yu, Bo; Yang, Jindou; Zhang, Ying; Chen, Xi; Zhang, Guofang, E-mail: gfzhang@snnu.edu.cn; Gao, Ziwei, E-mail: zwgao@snnu.edu.cn

    2015-01-15

    A successive anchoring of Ti(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 silica was conducted by SOMC strategy in moderate conditions. The silica, monitored by in-situ Fourier transform infrared spectroscopy (in-situ FT-IR), was pretreated at different temperatures (200, 500 and 800 °C). The ligand tailored silica-supported titanium complexes were characterized by in-situ FT-IR, {sup 13}C CP MAS-NMR, X-ray photoelectron spectroscopy (XPS), X-ray absorption near edge structure (XANES) and elemental analysis in detail, verifying that the surface titanium species are single sited. The catalytic activity of the ligand tailored single-site silica supported titanium complexes was evaluated by a cyanosilylation of benzaldehyde. The results showed that the catalytic activity is dependent strongly on the dehydroxylation temperatures of silica and the configuration of the ligands. - Graphical abstract: The ligand-tailored silica supported “single site” titanium complexes were synthesized by SOMC strategy and fully characterized. Their catalytic activity were evaluated by benzaldehyde silylcyanation. - Highlights: • Single-site silica supported Ti active species was prepared by SOMC technique. • O-donor ligand tailored Ti surface species was synthesized. • The surface species was characterized by XPS, {sup 13}C CP-MAS NMR, XANES etc. • Catalytic activity of the Ti active species in silylcyanation reaction was evaluated.

  5. Low-Temperature Molecular Layer Deposition Using Monofunctional Aromatic Precursors and Ozone-Based Ring-Opening Reactions.

    Science.gov (United States)

    Svärd, Laura; Putkonen, Matti; Kenttä, Eija; Sajavaara, Timo; Krahl, Fabian; Karppinen, Maarit; Van de Kerckhove, Kevin; Detavernier, Christophe; Simell, Pekka

    2017-09-26

    Molecular layer deposition (MLD) is an increasingly used deposition technique for producing thin coatings consisting of purely organic or hybrid inorganic-organic materials. When organic materials are prepared, low deposition temperatures are often required to avoid decomposition, thus causing problems with low vapor pressure precursors. Monofunctional compounds have higher vapor pressures than traditional bi- or trifunctional MLD precursors, but do not offer the required functional groups for continuing the MLD growth in subsequent deposition cycles. In this study, we have used high vapor pressure monofunctional aromatic precursors in combination with ozone-triggered ring-opening reactions to achieve sustained sequential growth. MLD depositions were carried out by using three different aromatic precursors in an ABC sequence, namely with TMA + phenol + O 3 , TMA + 3-(trifluoromethyl)phenol + O 3 , and TMA + 2-fluoro-4-(trifluoromethyl)benzaldehyde + O 3 . Furthermore, the effect of hydrogen peroxide as a fourth step was evaluated for all studied processes resulting in a four-precursor ABCD sequence. According to the characterization results by ellipsometry, infrared spectroscopy, and X-ray reflectivity, self-limiting MLD processes could be obtained between 75 and 150 °C with each of the three aromatic precursors. In all cases, the GPC (growth per cycle) decreased with increasing temperature. In situ infrared spectroscopy indicated that ring-opening reactions occurred in each ABC sequence. Compositional analysis using time-of-flight elastic recoil detection indicated that fluorine could be incorporated into the film when 3-(trifluoromethyl)phenol and 2-fluoro-4-(trifluoromethyl)benzaldehyde were used as precursors.

  6. Total Synthesis of (+)-Rishirilide B: Development and Application of General Processes for Enantioselective Oxidative Dearomatization of Resorcinol Derivatives

    Science.gov (United States)

    Mejorado, Lupe H.

    2008-01-01

    A concise synthesis of (+)-rishirilide B (2) is described. This is the first synthesis to be reported for the (+)-enantiomer of rishirilide B (2) as found in nature. The strategy accentuates the valuable combination of a method for o-quinone methide coupling with a method for enantioselective resorcinol dearomatization, which provides a densely functionalized chiral building block. The convergent synthesis illustrates several improvements and refinements to these methods and their supporting chemistries. Among these is the in situ generation of PhI[OTMS]OTf. Combination of this oxidant with phenol 31 constitutes the first example of a diastereoselective oxidative dearomatization of a resorcinol displaying a 2-alkyl substituent. In addition, the preparation of the cyclic sulfone 34 is reported. As a new dimethide precursor expressing a readily cleavable O-benzyl residue, sulfone 34 should prove useful in future endeavors. A protocol using the aluminum amide of dimethylhydrazine for opening and cleavage of a [1,4]-dioxan-2-one is also described. This procedure unmasks the hydroxy dione 36 by jettisoning the chiral directing group. Regioselective O-carbamylation of the 1,3-dione 36 enables the transformation of the remaining carbonyl into the α-hydroxy carboxylic acid found in 2. The total synthesis of (+)-rishirilide B (2) requires 15 pots from benzaldehyde 17 and 13 pots from benzaldehyde 32. The final product emerges in yields of 12.5% and 20.3% from compounds 17 and 32, respectively. The longest linear sequence requires eight chromatographies. Important observations leading to the development of the principle asymmetric method are described within the context of the total synthesis. PMID:17147370

  7. Tuning the Synthesis of Manganese Oxides Nanoparticles for Efficient Oxidation of Benzyl Alcohol

    Science.gov (United States)

    Fei, Jingyuan; Sun, Lixian; Zhou, Cuifeng; Ling, Huajuan; Yan, Feng; Zhong, Xia; Lu, Yuxiang; Shi, Jeffrey; Huang, Jun; Liu, Zongwen

    2017-01-01

    The liquid phase oxidation of benzyl alcohol is an important reaction for generating benzaldehyde and benzoic acid that are largely required in the perfumery and pharmaceutical industries. The current production systems suffer from either low conversion or over oxidation. From the viewpoint of economy efficiency and environmental demand, we are aiming to develop new high-performance and cost-effective catalysts based on manganese oxides that can allow the green aerobic oxidation of benzyl alcohol under mild conditions. It was found that the composition of the precursors has significant influence on the structure formation and surface property of the manganese oxide nanoparticles. In addition, the crystallinity of the resulting manganese nanoparticles was gradually improved upon increasing the calcination temperature; however, the specific surface area decreased obviously due to pore structure damage at higher calcination temperature. The sample calcined at the optimal temperature of 600 °C from the precursors without porogen was a Mn3O4-rich material with a small amount of Mn2O3, which could generate a significant amount of {O}_2- species on the surface that contributed to the high catalytic activity in the oxidation. Adding porogen with precursors during the synthesis, the obtained catalysts were mainly Mn2O3 crystalline, which showed relatively low activity in the oxidation. All prepared samples showed high selectivity for benzaldehyde and benzoic acid. The obtained catalysts are comparable to the commercial OMS-2 catalyst. The synthesis-structure-catalysis interaction has been addressed, which will help for the design of new high-performance selective oxidation catalysts.

  8. Isolation and characterization of Lactobacillus helveticus DSM 20075 variants with improved autolytic capacity.

    Science.gov (United States)

    Spus, Maciej; Liu, Hua; Wels, Michiel; Abee, Tjakko; Smid, Eddy J

    2017-01-16

    Lactobacillus helveticus is widely used in dairy fermentations and produces a range of enzymes, which upon cell lysis can be released into the cheese matrix and impact degradation of proteins, peptides and lipids. In our study we set out to explore the potential of Lb. helveticus DSM 20075 for increased autolytic capacity triggered by conditions such as low pH and high salt concentrations encountered in cheese environments. Lb. helveticus DSM 20075 was subjected to varied incubation temperatures (ranging from 37 to 50°C). High-temperature incubation (in the range of 45 to 50°C) allowed us to obtain a collection of six variant strains (V45-V50), which in comparison to the wild-type strain, showed higher growth rates at elevated temperatures (42°C-45°C). Moreover, variant strain V50 showed a 4-fold higher, in comparison to wild type, autolytic capacity in cheese-like conditions. Next, strain V50 was used as an adjunct in lab-scale cheese making trials to measure its impact on aroma formation during ripening. Specifically, in cheeses made with strain V50, the relative abundance of benzaldehyde increased 3-fold compared to cheeses made with the wild-type strain. Analysis of the genome sequence of strain V50 revealed multiple mutations in comparison to the wild-type strain DSM 20075 including a mutation found in a gene coding for a metal ion transporter, which can potentially be linked to intracellular accumulation of Mn 2+ and benzaldehyde formation. The approach of high-temperature incubation can be applied in dairy industry for the selection of (adjunct) cultures targeted at accelerated cheese ripening and aroma formation. Copyright © 2016 Elsevier B.V. All rights reserved.

  9. Mechanistic studies of nitrations and oxidations in solutions of dinitrogen pentaoxide in nitric acid

    Energy Technology Data Exchange (ETDEWEB)

    Willmer, R.F.

    1992-01-01

    Mechanisms of nitrations in solutions of dinitrogen pentaoxide in nitric acid of 1,2,4-trichloro-5-nitrobenzene and 1,2-dichloro-4-nitrobenzene have been proposed. The kinetics and products of the nitration, in the title medium, of substantially deactivated benzoic acids and benzaldehydes have been investigated. Kinetics of nitration of some substituted benzoic acids in nitric acid solutions containing dinitrogen pentaoxide or nitronium trifluoro-methanesulphonate (nitronium triflate) have been compared. Rate coefficients for reactions in dinitrogen pentaoxide solutions were generally similar to those from nitronium triflate solutions of the same estimated nitronium ion concentration. Yields of aromatic products of nitration of some benzoic acid derivatives in the nitric acid solutions have been determined. Nitrodecarboxylation of 4-fluorobenzoic acid occurs as a result of nitronium ion attach at C(1). The competition between oxidation to the corresponding benzoic acid and nitration in the aromatic ring of some substituted benzaldehydes has been probed by kinetic and product studies. 4-Carboxybenzaldehyde is nitrated but more deactivated substrates are predominantly oxidized. Rapid reversible gem-dinitrate formation occurs in concentrated dinitrogen pentaoxide solutions. The equilibrium extent of formation of [alpha]-deuterio-(4-nitropheny)-dinitratomethane from [alpha]-deuterio-4-nitrobenzaldehyde is reported. 4-nitrobenzaldehyde and the gem-dinitrate are oxidized in processes in which [alpha]-hydrogen loss is at least partially rate determining. The relative rates of oxidation in nitronium triflate solutions suggest that the [alpha]-hydrogen is removed as a hydride ion in that medium. There is evidence for the intrusion of a radical mechanism of nitration in concentrated solutions of dinitrogen pentaoxide. (4-Nitrophenyl)dinitratomethane was produced on the addition of 4-nitrobenzaldehyde to a solution of dinitrogen pentaoxide in dichloromethane.

  10. Synthesis, characterisation, reactivity and in vitro antiamoebic activity of hydrazone based oxovanadium(IV), oxovanadium(V) and mu-bis(oxo)bis{oxovanadium(V)} complexes.

    Science.gov (United States)

    Maurya, Mannar R; Agarwal, Shalu; Abid, Mohammad; Azam, Amir; Bader, Cerstin; Ebel, Martin; Rehder, Dieter

    2006-02-21

    -phenylacetaldehyde, benzaldehyde, benzoic acid and 1-phenyl-ethane-1,2-diol, while ethyl benzene yields benzyl alcohol, benzaldehyde and 1-phenyl-ethane-1,2-diol.

  11. The Fluorescence Enhancement of Mercury Detected in Food Based on Rhodamine Derivatives.

    Science.gov (United States)

    Fan, Cai-ling; Xie, Pu-hui; Cui, Shu-min; Yang, Li-na; Sun, Qing; Ai, Zhi-lu

    2015-05-01

    Recently, the problem of food security is more and more serious, and people pay attention to mercury because of the toxic of it. A new approach for the determination of mercury content in foodstuff is devised. In this paper, first, we design and synthesis a new kind of fluorescent probe whose matrix based on rhodamine B, hydrazine hydrate and hydroxy benzaldehyde. Through the analysis of H-NMR spectra of the synthesized product L1, we confirm that the synthetic substance is the adjacent carboxyl benzaldehyde hydrazone structure generation of rhodamine B. Then, we measure the fluorescence signal intensity of the probe with different concentrations of mercury ions fully upon complexation by fluorescence spectrometer and we can study the relationship between the mercury ion concentration and the fluorescence intensity and draw the standard working curve. Following, It's time to discuss the microwave digestion processing of tea, after digestion we use the synthetic probe Li for determination of mercury content in tea. The experimental results show that the maximum excitation wavelength of the probe and coordination compound are 568. 05 and 560. 00 nm, the maximum emission wavelength are 587. 94 and 580. 00 nm. Then we can find the best testing conditions to improve the degree of accuracy, that is: room temperature, 50% the methanol solution, 3. 0 mL pH 4. 0 buffer solution, in the extent of 30 min. The experimental results show that Na+, K+, Ca2+, Cu2+, Zn2+, Al3+ have little impact on the fluorescence intensity of the:probe. Fe3+, Mg2+, Ba2+ has a weak enhancement to the fluorescence intensity of the probe. While a low concentrations of Hg2+ have an obviously enhanced effect on the fluorescence intensity of the probe. In contrast to other metal ions, the probe for Hg2+ has a good selectivity. Linear relationship between the magnitude of increase in fluorescence intensity and concentration of mercury ion was in the range of 5~20 ng . L-1 with detection limit (3S/N) of

  12. Structural and kinetic studies on native intermediates and an intermediate analogue in benzoylformate decarboxylase reveal a least motion mechanism with an unprecedented short-lived predecarboxylation intermediate.

    Science.gov (United States)

    Bruning, Marc; Berheide, Marco; Meyer, Danilo; Golbik, Ralph; Bartunik, Hans; Liese, Andreas; Tittmann, Kai

    2009-04-21

    The thiamin diphosphate- (ThDP-) dependent enzyme benzoylformate decarboxylase (BFDC) catalyzes the nonoxidative decarboxylation of benzoylformic acid to benzaldehyde and carbon dioxide. To date, no structural information for a cofactor-bound reaction intermediate in BFDC is available. For kinetic analysis, a chromophoric substrate analogue was employed that produces various absorbing intermediates during turnover but is a poor substrate with a 10(4)-fold compromised kcat. Here, we have analyzed the steady-state distribution of native intermediates by a combined chemical quench/1H NMR spectroscopic approach and estimated the net rate constants of elementary catalytic steps. At substrate saturation, carbonyl addition of the substrate to the cofactor (k' approximately 500 s-1 at 30 degrees C) and elimination of benzaldehyde (k' approximately 2.400 s-1) were found to be partially rate-determining for catalysis, whereas decarboxylation of the transient 2-mandelyl-ThDP intermediate is 1 order of magnitude faster with k' approximately 16.000 s-1, the largest rate constant of decarboxylation in any thiamin enzyme characterized so far. The X-ray structure of a predecarboxylation intermediate analogue was determined to 1.6 A after cocrystallization of BFDC from Pseudomonas putida with benzoylphosphonic acid methyl ester. In contrast to the free acid, for which irreversible phosphorylation of active center Ser26 was reported, the methyl ester forms a covalent adduct with ThDP with a similar configuration at C2alpha as observed for other thiamin enzymes. The C2-C2alpha bond of the intermediate analogue is out of plane by 7degrees, indicating strain. The phosphonate part of the adduct forms hydrogen bonds with Ser26 and His281, and the 1-OH group is held in place by interactions with His70 and the 4'-amino group of ThDP. The phenyl ring accommodates in a hydrophobic pocket formed by Phe464, Phe397, Leu109, and Leu403. A comparison with the previously determined structure of

  13. Carbonyl emissions in diesel and biodiesel exhaust

    Science.gov (United States)

    Machado Corrêa, Sérgio; Arbilla, Graciela

    With the use of biodiesel in clear growth, it is important to quantify any potential emission benefits or liabilities of this fuel. Several researches are available concerning the regulated emissions of biodiesel/diesel blends, but there is a lack of information about non-regulated emissions. In a previous paper [Corrêa, S.M., Arbilla, G., 2006. Emissões de formaldeído e acetaldeído de misturas biodiesel/diesel. Periódico Tchê Química, 3, 54-68], the emissions of aromatic hydrocarbons were reported. In this work, seven carbonyl emissions (formaldehyde, acetaldehyde, acrolein, acetone, propionaldehyde, butyraldehyde, and benzaldehyde) were evaluated by a heavy-duty diesel engine fueled with pure diesel (D) and biodiesel blends (v/v) of 2% (B2), 5% (B5), 10% (B10), and 20% (B20). The tests were conducted using a six cylinder heavy-duty engine, typical of the Brazilian fleet of urban buses, in a steady-state condition under 1000, 1500, and 2000 rpm. The exhaust gases were diluted nearly 20 times and the carbonyls were sampled with SiO 2-C18 cartridges, impregnated with acid solution of 2,4-dinitrophenylhydrazine. The chemical analyses were performed by high performance liquid chromatography using UV detection. Using average values for the three modes of operation (1000, 1500, and 2000 rpm) benzaldehyde showed a reduction on the emission (-3.4% for B2, -5.3% for B5, -5.7% for B10, and -6.9% for B20) and all other carbonyls showed a significative increase: 2.6, 7.3, 17.6, and 35.5% for formaldehyde; 1.4, 2.5, 5.4, and 15.8% for acetaldehyde; 2.1, 5.4, 11.1, and 22.0% for acrolein+acetone; 0.8, 2.7, 4.6, and 10.0% for propionaldehyde; 3.3, 7.8, 16.0, and 26.0% for butyraldehyde.

  14. Retinoic acid signaling plays a restrictive role in zebrafish primitive myelopoiesis.

    Directory of Open Access Journals (Sweden)

    Dong Liang

    Full Text Available Retinoic acid (RA is known to regulate definitive myelopoiesis but its role in vertebrate primitive myelopoiesis remains unclear. Here we report that zebrafish primitive myelopoiesis is restricted by RA in a dose dependent manner mainly before 11 hpf (hours post fertilization when anterior hemangioblasts are initiated to form. RA treatment significantly reduces expressions of anterior hemangioblast markers scl, lmo2, gata2 and etsrp in the rostral end of ALPM (anterior lateral plate mesoderm of the embryos. The result indicates that RA restricts primitive myelopoiesis by suppressing formation of anterior hemangioblasts. Analyses of ALPM formation suggest that the defective primitive myelopoiesis resulting from RA treatment before late gastrulation may be secondary to global loss of cells for ALPM fate whereas the developmental defect resulting from RA treatment during 10-11 hpf should be due to ALPM patterning shift. Overexpressions of scl and lmo2 partially rescue the block of primitive myelopoiesis in the embryos treated with 250 nM RA during 10-11 hpf, suggesting RA acts upstream of scl to control primitive myelopoiesis. However, the RA treatment blocks the increased primitive myelopoiesis caused by overexpressing gata4/6 whereas the abolished primitive myelopoiesis in gata4/5/6 depleted embryos is well rescued by 4-diethylamino-benzaldehyde, a retinal dehydrogenase inhibitor, or partially rescued by knocking down aldh1a2, the major retinal dehydrogenase gene that is responsible for RA synthesis during early development. Consistently, overexpressing gata4/6 inhibits aldh1a2 expression whereas depleting gata4/5/6 increases aldh1a2 expression. The results reveal that RA signaling acts downstream of gata4/5/6 to control primitive myelopoiesis. But, 4-diethylamino-benzaldehyde fails to rescue the defective primitive myelopoiesis in either cloche embryos or lycat morphants. Taken together, our results demonstrate that RA signaling restricts

  15. Ligand-protein conjugated quantification assay by UV spectrophotometry in 99mTc indirect labeling

    International Nuclear Information System (INIS)

    Basualdo, Daniel A.; Rabiller, Graciela; Poch, Carolina; El Tamer, Elias A.

    2009-01-01

    Objective: Quantify IgG-HYNIC conjugated for obtaining substitution ratio and as a chemical quality control for 99m Tc labeling of this immunoglobulin. Introduction: The Operational Guidance on Hospital Radiopharmacy by IAEA states that the procedures performed in a Radiopharmacy Laboratory fall into three operational levels. At present, Nuclear Medicine Centre of 'Hospital de Clinicas' has an operational level 2b which requires the preparation of radiopharmaceuticals from approved reagent kits and radionuclide generators, and labeling of autologous blood cells. Centre's goal is to reach an operational level 3a, which allows us to compounding radiopharmaceuticals from drugs and radionuclides for diagnosis; modification to existing commercial kits; related research and development. In approach of that goal, we addressed the optimization of conjugation of proteins and peptides with S-HYNIC so as to bring about the procedures involved. In this work, was conjugated nonspecific polyclonal immunoglobulin G (IgG) with S-HYNIC. Our interest was focused in calculate how many HYNIC groups were incorporated per IgG molecule so that in later stages can be obtained a correlate with labeling efficiency. Materials and methods: A sample of IgG-HYNIC conjugate of 0.2 ml was diluted in 4 ml of benzaldehyde o-sulfonic acid (1 mg / ml, 0.1 M NaAc, pH 4.7). The reaction was incubated at room temperature overnight in darkness. As a negative control took 0.2 ml of IgG-HYNIC conjugate in 4 ml of NaAc buffer 0.1 M. 3 ml of benzaldehyde o-sulfonic acid (1 mg / ml 0.1 M NaAc, pH 4.7) was used as blank. The absorption of the hydrazone was read at 343 nm. The hydrazine concentration was calculated using a molar extinction coefficient ε (343 nm) 17000 M-1cm-1. Results: Molar substitution ratio (MSR) was calculated. The MSR indicates the number of HYNIC groups incorporated in the IgG-HYNIC conjugate determined by the spectrophotometric assay. Conclusions: In labeling with a bifunctional

  16. Mechanistic aspects of hydrosilylation catalyzed by (ArN=)Mo(H)(Cl)(PMe3)3.

    Science.gov (United States)

    Khalimon, Andrey Y; Shirobokov, Oleg G; Peterson, Erik; Simionescu, Razvan; Kuzmina, Lyudmila G; Howard, Judith A K; Nikonov, Georgii I

    2012-04-02

    The reaction of (ArN=)MoCl(2)(PMe(3))(3) (Ar = 2,6-diisopropylphenyl) with L-Selectride gives the hydrido-chloride complex (ArN=)Mo(H)(Cl)(PMe(3))(3) (2). Complex 2 was found to catalyze the hydrosilylation of carbonyls and nitriles as well as the dehydrogenative silylation of alcohols and water. Compound 2 does not show any productive reaction with PhSiH(3); however, a slow H/D exchange and formation of (ArN=)Mo(D)(Cl)(PMe(3))(3) (2(D)) was observed upon addition of PhSiD(3). Reactivity of 2 toward organic substrates was studied. Stoichiometric reactions of 2 with benzaldehyde and cyclohexanone start with dissociation of the trans-to-hydride PMe(3) ligand followed by coordination and insertion of carbonyls into the Mo-H bond to form alkoxy derivatives (ArN=)Mo(Cl)(OR)(PMe(2))L(2) (3: R = OCH(2)Ph, L(2) = 2 PMe(3); 5: R = OCH(2)Ph, L(2) = η(2)-PhC(O)H; 6: R = OCy, L(2) = 2 PMe(3)). The latter species reacts with PhSiH(3) to furnish the corresponding silyl ethers and to recover the hydride 2. An analogous mechanism was suggested for the dehydrogenative ethanolysis with PhSiH(3), with the key intermediate being the ethoxy complex (ArN=)Mo(Cl)(OEt)(PMe(3))(3) (7). In the case of hydrosilylation of acetophenone, a D-labeling experiment, i.e., a reaction of 2 with acetophenone and PhSiD(3) in the 1:1:1 ratio, suggests an alternative mechanism that does not involve the intermediacy of an alkoxy complex. In this particular case, the reaction presumably proceeds via Lewis acid catalysis. Similar to the case of benzaldehyde, treatment of 2 with styrene gives trans-(ArN=)Mo(H)(η(2)-CH(2)═CHPh)(PMe(3))(2) (8). Complex 8 slowly decomposes via the release of ethylbenzene, indicating only a slow insertion of styrene ligand into the Mo-H bond of 8.

  17. Screening of Polish Fir Honeydew Honey Using GC/MS, HPLC-DAD, and Physical-Chemical Parameters: Benzene Derivatives and Terpenes as Chemical Markers.

    Science.gov (United States)

    Kuś, Piotr M; Jerković, Igor; Marijanović, Zvonimir; Tuberoso, Carlo I G

    2017-09-01

    GC/MS of headspace solid phase micro extraction (HS-SPME) and solvent extractives along with targeted HPLC-DAD of Polish fir (Abies alba Mill.) honeydew honey (FHH), were used to determine the chemical profiles and potential markers of botanical origin. Additionally, typical physical-chemical parameters were also assigned. The values determined for FHH were: conductivity (1.2 mS/cm), water content (16.7 g/100 g), pH (4.5), and CIE chromaticity coordinates (L* = 48.4, a* = 20.6, b* = 69.7, C* = 72.9, and h° = 73.5). FHH contained moderate-high total phenolic content (533.2 mg GAE/kg) and antioxidant activity (1.1 mmol TEAC/kg) and (3.2 mmol Fe 2+ /kg) in DPPH and FRAP assays. The chemical profiles were dominated by source plant-originated benzene derivatives: 3,4-dihydroxybenzoic acid (up to 8.7 mg/kg, HPLC/honey solution), methyl syringate (up to 14.5%, GC/solvent extracts) or benzaldehyde (up to 43.7%, GC/headspace). Other markers were terpenes including norisoprenoid (4-hydroxy-3,5,6-trimethyl-4-(3-oxobut-1-enyl)cyclohex-2-en-1-one, up to 20.3%, GC/solvent extracts) and monoterpenes, mainly linalool derivatives (up to 49%, GC/headspace) as well as borneol (up to 5.9%, GC/headspace). The application of various techniques allowed comprehensive characterisation of FHH. 4-Hydroxy-3,5,6-trimethyl-4-(3-oxobut-1-enyl)cyclohex-2-en-1-one, coniferyl alcohol, borneol, and benzaldehyde were first time proposed for FHH screening. Protocatechuic acid may be a potential marker of FFH regardless of the geographical origin. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

  18. Metal- and Ligand-Accelerated Catalysis of the Baylis-Hillman Reaction.

    Science.gov (United States)

    Aggarwal, Varinder K.; Mereu, Andrea; Tarver, Gary J.; McCague, Ray

    1998-10-16

    The Baylis-Hillman reaction, the coupling of an unsaturated carbonyl compound/nitrile with aldehydes, is a valuable reaction but is limited in its practicality by poor reaction rates. We have endeavored to accelerate the reaction using Lewis acids and found that while conventional Lewis acids gave reduced rates group III, and lanthanide triflates (5 mol %) gave increased rates. The optimum metal salts were La(OTf)(3) and Sm(OTf)(3), which gave rate accelerations (k(rel)) of approximately 4.7 and 4.9, respectively, in reactions between tert-butyl acrylate and benzaldehyde when using stoichiometric amounts of DABCO. At low loadings of DABCO (up to 10 mol %), no reaction occurred due to association of DABCO with the metal. Use of additional ligands to displace the DABCO from the metal was studied, and the rate of reaction was found to increase further in most cases. Of the ligands tested, at 5 mol %, (+)-binol gave one of the largest rate accelerations (3.4-fold) and was studied in more detail. It was found that reactions occurred even at low DABCO concentration so that here the Lewis base and Lewis acid were able to promote the reaction without interference from each other. While the (+)-binol (and other chiral ligands) failed to provide any significant asymmetric induction, a substantial nonlinear effect was observed with binol. Thus, use of racemic binol gave no effect on the rate. In seeking to maximize the rate attainable, more soluble (liquid) ligands were studied. Diethyl tartrate and triethanolamine gave rate enhancements of 5.2x and 3.5x at 50 mol %, respectively, versus 1.5x and 2.3x at 5 mol %. The best protocol was to use 100 mol % DABCO, 50 mol % triethanolamine, and 5 mol % La(OTf)(3). This gave overall rate accelerations of between 23-fold and 40-fold depending on the acrylate and approximately 5-fold for acrylonitrile. A simple acid wash removed the reagents, leaving the product in the organic phase. While triethanolamine accelerated the reaction

  19. Facile synthesis of ultrasmall monodisperse ``raisin-bun''-type MoO3/SiO2 nanocomposites with enhanced catalytic properties

    Science.gov (United States)

    Wang, Jiasheng; Li, Xin; Zhang, Shufen; Lu, Rongwen

    2013-05-01

    We report the preparation of ultrasmall monodisperse MoO3/SiO2 nanocomposites in reverse microemulsions formed by Brij-58/cyclohexane/water. The nanocomposites are of ``raisin-bun''-type with 1.0 +/- 0.2 nm MoO3 homogeneously dispersed in 23 +/- 2 nm silica spheres. Characterization is carried out based on transmission electron microscopy (TEM), high-resolution transmission electron microscopy (HRTEM), energy-dispersive X-ray spectrometry (EDS), X-ray powder diffraction (XRD), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), inductively coupled plasma-optical emission spectrometry (ICP-OES), N2 sorption measurement, and NH3 temperature-programmed desorption (NH3-TPD). The as-prepared MoO3/SiO2 nanocomposites are microporous and exhibit enhanced catalytic activities for acetalization of benzaldehyde with ethylene glycol and can be repeatedly used 5 times without obvious deactivation. The catalytic performance improvement is attributed to the unique structure and ultrasmall size of the nanocomposites.We report the preparation of ultrasmall monodisperse MoO3/SiO2 nanocomposites in reverse microemulsions formed by Brij-58/cyclohexane/water. The nanocomposites are of ``raisin-bun''-type with 1.0 +/- 0.2 nm MoO3 homogeneously dispersed in 23 +/- 2 nm silica spheres. Characterization is carried out based on transmission electron microscopy (TEM), high-resolution transmission electron microscopy (HRTEM), energy-dispersive X-ray spectrometry (EDS), X-ray powder diffraction (XRD), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), inductively coupled plasma-optical emission spectrometry (ICP-OES), N2 sorption measurement, and NH3 temperature-programmed desorption (NH3-TPD). The as-prepared MoO3/SiO2 nanocomposites are microporous and exhibit enhanced catalytic activities for acetalization of benzaldehyde with ethylene glycol and can be repeatedly used 5 times without obvious deactivation. The catalytic performance improvement is attributed to the unique

  20. pH-Responsive Tumor-Targetable Theranostic Nanovectors Based on Core Crosslinked (CCL Micelles with Fluorescence and Magnetic Resonance (MR Dual Imaging Modalities and Drug Delivery Performance

    Directory of Open Access Journals (Sweden)

    Sidan Tian

    2016-06-01

    Full Text Available The development of novel theranostic nanovectors is of particular interest in treating formidable diseases (e.g., cancers. Herein, we report a new tumor-targetable theranostic agent based on core crosslinked (CCL micelles, possessing tumor targetable moieties and fluorescence and magnetic resonance (MR dual imaging modalities. An azide-terminated diblock copolymer, N3-POEGMA-b-P(DPA-co-GMA, was synthesized via consecutive atom transfer radical polymerization (ATRP, where OEGMA, DPA, and GMA are oligo(ethylene glycolmethyl ether methacrylate, 2-(diisopropylaminoethyl methacrylate, and glycidyl methacrylate, respectively. The resulting diblock copolymer was further functionalized with DOTA(Gd (DOTA is 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakisacetic acid or benzaldehyde moieties via copper(I-catalyzed alkyne-azide cycloaddition (CuAAC chemistry, resulting in the formation of DOTA(Gd-POEGMA-b-P(DPA-co-GMA and benzaldehyde-POEGMA-b-P(DPA-co-GMA copolymers. The resultant block copolymers co-assembled into mixed micelles at neutral pH in the presence of tetrakis[4-(2-mercaptoethoxyphenyl]ethylene (TPE-4SH, which underwent spontaneous crosslinking reactions with GMA residues embedded within the micellar cores, simultaneously switching on TPE fluorescence due to the restriction of intramolecular rotation. Moreover, camptothecin (CPT was encapsulated into the crosslinked cores at neutral pH, and tumor-targeting pH low insertion peptide (pHLIP, sequence: AEQNPIYWARYADWLFTTPLLLLDLALLVDADEGTCG moieties were attached to the coronas through the Schiff base chemistry, yielding a theranostic nanovector with fluorescence and MR dual imaging modalities and tumor-targeting capability. The nanovectors can be efficiently taken up by A549 cells, as monitored by TPE fluorescence. After internalization, intracellular acidic pH triggered the release of loaded CPT, killing cancer cells in a selective manner. On the other hand, the nanovectors labeled with DOTA

  1. Molecular Switch for Sub-Diffraction Laser Lithography by Photoenol Intermediate-State Cis-Trans Isomerization.

    Science.gov (United States)

    Mueller, Patrick; Zieger, Markus M; Richter, Benjamin; Quick, Alexander S; Fischer, Joachim; Mueller, Jonathan B; Zhou, Lu; Nienhaus, Gerd Ulrich; Bastmeyer, Martin; Barner-Kowollik, Christopher; Wegener, Martin

    2017-06-27

    Recent developments in stimulated-emission depletion (STED) microscopy have led to a step change in the achievable resolution and allowed breaking the diffraction limit by large factors. The core principle is based on a reversible molecular switch, allowing for light-triggered activation and deactivation in combination with a laser focus that incorporates a point or line of zero intensity. In the past years, the concept has been transferred from microscopy to maskless laser lithography, namely direct laser writing (DLW), in order to overcome the diffraction limit for optical lithography. Herein, we propose and experimentally introduce a system that realizes such a molecular switch for lithography. Specifically, the population of intermediate-state photoenol isomers of α-methyl benzaldehydes generated by two-photon absorption at 700 nm fundamental wavelength can be reversibly depleted by simultaneous irradiation at 440 nm, suppressing the subsequent Diels-Alder cycloaddition reaction which constitutes the chemical core of the writing process. We demonstrate the potential of the proposed mechanism for STED-inspired DLW by covalently functionalizing the surface of glass substrates via the photoenol-driven STED-inspired process exploiting reversible photoenol activation with a polymerization initiator. Subsequently, macromolecules are grown from the functionalized areas and the spatially coded glass slides are characterized by atomic-force microscopy. Our approach allows lines with a full-width-at-half-maximum of down to 60 nm and line gratings with a lateral resolution of 100 nm to be written, both surpassing the diffraction limit.

  2. Interdisciplinary investigation on ancient Ephedra twigs from Gumugou Cemetery (3800 B.P.) in Xinjiang region, northwest China.

    Science.gov (United States)

    Xie, Mingsi; Yang, Yimin; Wang, Binghua; Wang, Changsui

    2013-07-01

    In the dry northern temperate regions of the northern hemisphere, the genus Ephedra comprises a series of native shrub species with a cumulative application history reaching back well over 2,000 years for the treatment of asthma, cold, fever, as well as many respiratory system diseases, especially in China. There are ethnological and philological evidences of Ephedra worship and utilization in many Eurasia Steppe cultures. However, no scientifically verifiable, ancient physical proof has yet been provided for any species in this genus. This study reports the palaeobotanical finding of Ephedra twigs discovered from burials of the Gumugou archaeological site, and ancient community graveyard, dated around 3800 BP, in Lop Nor region of northwestern China. The macro-remains were first examined by scanning electron microscope (SEM) and then by gas chromatography-mass spectrometry (GC-MS) for traits of residual biomarkers under the reference of modern Ephedra samples. The GC-MS result of chemical analysis presents the existence of Ephedra-featured compounds, several of which, including benzaldehyde, tetramethyl-pyrazine, and phenmetrazine, are found in the chromatograph of both the ancient and modern sample. These results confirm that the discovered plant remains are Ephedra twigs. Although there is no direct archaeological evidence for the indication of medicinal use of this Ephedra, the unified burial deposit in which the Ephedra was discovered is a strong indication of the religious and medicinal awareness of the human inhabitants of Gumugou towards this plant. Copyright © 2013 Wiley Periodicals, Inc.

  3. Synthesis and anticonvulsant activity of 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o/p-substituted benzal) hydrazone derivatives.

    Science.gov (United States)

    Gökçe, Mehtap; Geciken, Ahmet Emin; Yildirim, Engin; Tosuni, Ali Ulvi

    2008-01-01

    It is well known that some hydrazone derivatives of both 2-oxobenzoxazoline and 2-oxobenzothiazoline exhibit potent anticonvulsant activity. In order to investigate the effects of structural modifications on the biological properties, 14 new hydrazones of 5-chloro-2(3H)-benzox-azolinone-3-acetyl hydrazide were synthesized. The chemical structures of the synthesized compounds were established by IR, 1H-NMR spectral analyses and elementary analyses. The anticonvulsant activities of the title compounds were tested by the penthylenetetrazole induced seizure test. 5-Chloro-2(3H)-benz-oxazolinone-3-acetyl-2-(o-methoxy-benzaldehyde)-hydrazone 4d, 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o-methybenzaldehyde)-hydrazone 4g, 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(p-methylbenzaldehyde)-hydrazone 4h, 5-chloro-2(3H)-benzoxazolino-ne-3-acetyl-2-(p-nitrobenzaldehyde)-hydrazone 4m, and 5-chloro-2(3H)-benzox-azolinone-3-acetyl-2-(p-dimethylaminobenzaldehyde)-hydrazone 4n were found more active than phenytoin (CAS 57-41-0) in the tests.

  4. Metabolic production of a novel polymer feedstock, 3-carboxy muconate, from vanillin.

    Science.gov (United States)

    Gosling, Aaron; Fowler, S Jane; O'Shea, Michael S; Straffon, Melissa; Dumsday, Geoff; Zachariou, Michael

    2011-04-01

    Vanillin can be produced on a commercial scale by depolymerising renewable lignin. One product of microbial metabolism of vanillin by common soil microbes, such as Acinetobacter baylyi, is a tricarboxylic acid with a butadiene backbone known as 3-carboxy muconate (3CM). Three enzymes, 4-hydroxy benzaldehyde dehydrogenase, vanillate monooxygenase and protocatechuate 3,4-dioxygenase, catalyse the biotransformation of vanillin to 3CM. These three enzymes were metabolically engineered into an Escherichia coli host, giving a biocatalyst that converted vanillin into 3CM. The biocatalyst was found to give 100% yield of 3CM from 1 mM of vanillin after 39 h. The rate-limiting reaction was identified as the conversion of vanillate to 3,4-dihydroxybenzoate catalysed by vanillate monooxygenase. Low expression of the reductase subunit of this enzyme was identified as contributing to the reduced rate of this reaction. Proof of principle of a novel application for 3CM was demonstrated when it was converted into a trimethyl ester derivative and copolymerised with styrene.

  5. Studies on the effect of a newly synthesized Schiff base compound from phenazone and vanillin on the corrosion of steel in 2M HCl

    International Nuclear Information System (INIS)

    Emreguel, Kaan C.; Hayvali, Mustafa

    2006-01-01

    The inhibiting action of a Schiff base 4-[(4-hydroxy-3-hydroxymethyl-benzylidene)-amino]-1,5-dimethyl-2-phenyl-1,2 -dihydro-pyrazol-3-one (phv), derived from 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (phz) and 4-hydroxy-3-methoxy-benzaldehyde (vn), towards the corrosion behavior of steel in 2M HCl solution has been studied using weight loss, polarization and electrochemical impedance spectroscopy (EIS) techniques. Although vn and phz were found to retard the corrosion rate of steel, the compound synthesized from vn and phz was seen to retard the corrosion rate even more. At constant temperature, the corrosion rate decreases with increasing inhibitor concentration. However, at any inhibitor concentration the increase in temperature leads to an increase in the corrosion rate of steel. The activations energies, ΔE a , as well as other thermodynamic parameters (ΔG ads 0 , ΔH ads 0 ) for the inhibitor process were calculated. The inhibitor efficiencies calculated from all the applied methods were in agreement and were found to be in the order: phv>phz>vn

  6. Functional characterization of a vanillin dehydrogenase in Corynebacterium glutamicum

    Science.gov (United States)

    Ding, Wei; Si, Meiru; Zhang, Weipeng; Zhang, Yaoling; Chen, Can; Zhang, Lei; Lu, Zhiqiang; Chen, Shaolin; Shen, Xihui

    2015-01-01

    Vanillin dehydrogenase (VDH) is a crucial enzyme involved in the degradation of lignin-derived aromatic compounds. Herein, the VDH from Corynebacterium glutamicum was characterized. The relative molecular mass (Mr) determined by SDS-PAGE was ~51kDa, whereas the apparent native Mr values revealed by gel filtration chromatography were 49.5, 92.3, 159.0 and 199.2kDa, indicating the presence of dimeric, trimeric and tetrameric forms. Moreover, the enzyme showed its highest level of activity toward vanillin at pH 7.0 and 30C, and interestingly, it could utilize NAD+ and NADP+ as coenzymes with similar efficiency and showed no obvious difference toward NAD+ and NADP+. In addition to vanillin, this enzyme exhibited catalytic activity toward a broad range of substrates, including p-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, o-phthaldialdehyde, cinnamaldehyde, syringaldehyde and benzaldehyde. Conserved catalytic residues or putative cofactor interactive sites were identified based on sequence alignment and comparison with previous studies, and the function of selected residues were verified by site-directed mutagenesis analysis. Finally, the vdh deletion mutant partially lost its ability to grow on vanillin, indicating the presence of alternative VDH(s) in Corynebacterium glutamicum. Taken together, this study contributes to understanding the VDH diversity from bacteria and the aromatic metabolism pathways in C. glutamicum. PMID:25622822

  7. A vanillin derivative causes mitochondrial dysfunction and triggers oxidative stress in Cryptococcus neoformans.

    Science.gov (United States)

    Kim, Jin Hyo; Lee, Han-Ok; Cho, Yong-Joon; Kim, Jeongmi; Chun, Jongsik; Choi, Jaehyuk; Lee, Younghoon; Jung, Won Hee

    2014-01-01

    Vanillin is a well-known food and cosmetic additive and has antioxidant and antimutagenic properties. It has also been suggested to have antifungal activity against major human pathogenic fungi, although it is not very effective. In this study, the antifungal activities of vanillin and 33 vanillin derivatives against the human fungal pathogen Cryptococcus neoformans, the main pathogen of cryptococcal meningitis in immunocompromised patients, were investigated. We found a structural correlation between the vanillin derivatives and antifungal activity, showing that the hydroxyl or alkoxy group is more advantageous than the halogenated or nitrated group in benzaldehyde. Among the vanillin derivatives with a hydroxyl or alkoxy group, o-vanillin and o-ethyl vanillin showed the highest antifungal activity against C. neoformans. o-Vanillin was further studied to understand the mechanism of antifungal action. We compared the transcriptome of C. neoformans cells untreated or treated with o-vanillin by using RNA sequencing and found that the compound caused mitochondrial dysfunction and triggered oxidative stress. These antifungal mechanisms of o-vanillin were experimentally confirmed by the significantly reduced growth of the mutants lacking the genes involved in mitochondrial functions and oxidative stress response.

  8. 4-Carbomethoxybenzaldehyde as a highly sensitive pre-column fluorescence derivatization reagent for 9,10-phenanthrenequinone.

    Science.gov (United States)

    Kishikawa, Naoya; Nakao, Maiko; Elgawish, Mohamed Saleh; Ohyama, Kaname; Nakashima, Kenichiro; Kuroda, Naotaka

    2011-07-15

    9,10-Phenanthrenequinone (PQ) is harmful environmental pollutant that is detected in airborne particulates. The measurement of PQ in the air should be necessary to evaluate the potential adverse effects of PQ on human health. We have recently developed a determination method for PQ based on the fluorescence derivatization of PQ using benzaldehyde and ammonium acetate as a reagent. In this study, in order to obtain more sensitive and selective fluorescence derivatization reaction, we measured the fluorescence of the reaction mixture of PQ with 21 kinds of aromatic aldehydes in the presence of ammonium acetate. Among the tested aldehydes, 4-carbomethoxybenzaldehyde was found to be the best reagent in regard to fluorescence intensity and emission wavelength maximum. Based on the fluorescence derivatization with 4-carbomethoxybenzaldehyde, a highly sensitive chromatographic method was developed for the determination of PQ with the detection limit (S/N=3) of 1.2 fmol/injection. Crown Copyright © 2011. Published by Elsevier B.V. All rights reserved.

  9. Synthesis and reactions of triphenylphosphine-O-benzophenonimine and derivatives

    International Nuclear Information System (INIS)

    Elamin, Manahil Babiker

    1999-08-01

    O-Amino benzophenone and its para and meta isomers were prepared using Friedl-Craft benzoylation. Their azides were also prepared via their diazonium salts. The azide of o-amino benzophenone in its reduced form (o-benzylaniline) and its cyclic ketal were synthesised. All azides thus formed were reacted separately with triphenylphosphine to give the corresponding phosphinimines, the Wittig reagents nitrogen analog. The reactivity of the phosphorous bond. (P=N) in the different phosphoranes were studied by two types of reactions: (1) the Wittig type of reaction using benzaldehyde and its into derivatives with each of the above prepared phosphinimines. While triphenylphosphine-m-benzophenonimine (ii) and the triphenylphosphine benzophenonimine ethylene acetal (v) and it's reduced form triphenylphosphine-o-benzophenonimine (iv) react giving the corresponding schiffis bases. However, the ortho (i) and the para (iii) isomers failed to react. This lack of reactivity is presumably due to their great stability which came about through the extensive resonance that reduced the nucleophilicity of the nitrogen nucleophiles. (2) The phophinimines each was irradiated using Hanovia medium pressure UV lamp. Also the ortho and para isomers were not affected while others reacted giving the corresponding azo-compound and triphenylphosphine. they were separated and detected by chromatography.(Author)

  10. Biocatalytic behaviour of immobilized Rhizopus oryzae lipase in the 1,3-selective ethanolysis of sunflower oil to obtain a biofuel similar to biodiesel.

    Science.gov (United States)

    Luna, Carlos; Verdugo, Cristóbal; Sancho, Enrique D; Luna, Diego; Calero, Juan; Posadillo, Alejandro; Bautista, Felipa M; Romero, Antonio A

    2014-08-04

    A new biofuel similar to biodiesel was obtained in the 1,3-selective transesterification reaction of sunflower oil with ethanol using as biocatalyst a Rhizopus oryzae lipase (ROL) immobilized on Sepiolite, an inorganic support. The studied lipase was a low cost powdered enzyme preparation, Biolipase-R, from Biocon-Spain, a multipurpose additive used in food industry. In this respect, it is developed a study to optimize the immobilization procedure of these lipases on Sepiolite. Covalent immobilization was achieved by the development of an inorganic-organic hybrid linker formed by a functionalized hydrocarbon chain with a pendant benzaldehyde, bonded to the AlPO4 support surface. Thus, the covalent immobilization of lipases on amorphous AlPO4/sepiolite (20/80 wt %) support was evaluated by using two different linkers (p-hydroxybenzaldehyde and benzylamine-terephthalic aldehyde, respectively). Besides, the catalytic behavior of lipases after physical adsorption on the demineralized sepiolite  was also evaluated. Obtained results indicated that covalent immobilization with the p-hydroxybenzaldehyde linker gave the best biocatalytic behavior. Thus, this covalently immobilized lipase showed a remarkable stability as well as an excellent capacity of reutilization (more than five successive reuses) without a significant loss of its initial catalytic activity. This could allow a more efficient fabrication of biodiesel minimizing the glycerol waste production.

  11. Spectroscopic studies of the intramolecular hydrogen bonding in o-hydroxy Schiff bases, derived from diaminomaleonitrile, and their deprotonation reaction products

    Science.gov (United States)

    Szady-Chełmieniecka, Anna; Kołodziej, Beata; Morawiak, Maja; Kamieński, Bohdan; Schilf, Wojciech

    2018-01-01

    The structural study of five Schiff bases derived from diaminomaleonitrile (DAMN) and 2-hydroxy carbonyl compounds was performed using 1H, 13C and 15N NMR methods in solution and in the solid state as well. ATR-FTIR and X-Ray spectroscopies were used for confirmation of the results obtained by NMR method. The imine obtained from DAMN and benzaldehyde was synthesized as a model compound which lacks intramolecular hydrogen bond. Deprotonation of all synthesized compounds was done by treating with tetramethylguanidine (TMG). NMR data revealed that salicylidene Schiff bases in DMSO solution exist as OH forms without intramolecular hydrogen bonds and independent on the substituents in aromatic ring. In the case of 2-hydroxy naphthyl derivative, the OH proton is engaged into weak intramolecular hydrogen bond. Two of imines (salDAMN and 5-BrsalDAMN) exist in DMSO solution as equilibrium mixtures of two isomers (A and B). The structures of equilibrium mixture in the solid state have been studied by NMR, ATR-FTIR and X-Ray methods. The deprotonation of three studied compounds (salDAMN, 5-BrsalDAMN, and 5-CH3salDAMN) proceeded in two different ways: deprotonation of oxygen atom (X form) or of nitrogen atom of free primary amine group of DAMN moiety (Y form). For 5-NO2salDAMN and naphDAMN only one form (X) was observed.

  12. HS-SPME GC/MS characterization of volatiles in raw and dry-roasted almonds (Prunus dulcis).

    Science.gov (United States)

    Xiao, Lu; Lee, Jihyun; Zhang, Gong; Ebeler, Susan E; Wickramasinghe, Niramani; Seiber, James; Mitchell, Alyson E

    2014-05-15

    A robust HS-SPME and GC/MS method was developed for analyzing the composition of volatiles in raw and dry-roasted almonds. Almonds were analyzed directly as ground almonds extracted at room temperature. In total, 58 volatiles were identified in raw and roasted almonds. Straight chain aldehydes and alcohols demonstrated significant but minimal increases, while the levels of branch-chain aldehydes, alcohols, heterocyclic and sulfur containing compounds increased significantly (500-fold) in response to roasting (p<0.05). Benzaldehyde decreased from 2934.6±272.5 ng/g (raw almonds) to 315.8±70.0 ng/g (averaged across the roasting treatments evaluated i.e. 28, 33 and 38 min at 138 °C) after roasting. Pyrazines were detected in only the roasted almonds, with the exception of 2,5-dimethylpyrazine, which was also found in raw almonds. The concentration of most alcohols increased in the roasted samples with the exception of 2-methyl-1-propanol, 3-methyl-1-butanol and 2-phenylethyl alcohol, which decreased 68%, 80%, and 86%, respectively. Copyright © 2013 Elsevier Ltd. All rights reserved.

  13. Enantioselective Synthesis of Various Cyanohydrins Using Covalently Immobilized Preparations of Hydroxynitrile Lyase from Prunus dulcis.

    Science.gov (United States)

    Alagöz, Dilek; Tükel, S Seyhan; Yildirim, Deniz

    2015-11-01

    The carrier-based and carrier-free (cross-linked enzyme aggregate) covalent immobilizations of Prunus dulcis hydroxynitrile lyase were investigated. The immobilized preparations were tested for enantioselective carbon-carbon bond formation activity in the biphasic medium. Of the tested preparations, only cross-linked enzyme aggregate of P. dulcis hydroxynitrile lyase (PdHNL-CLEA) achieved the synthesis of (R)-mandelonitrile with 93% yield and 99% enantiopurity. PdHNL-CLEA was also used in the synthesis of various (R)-cyanohydrins from corresponding aldehydes/ketones and hydrocyanic acid. When 4-methoxybenzaldehyde, 4-methyl benzaldehyde, and 4-hydroxybenzaldehyde were used as substrates, the yield-enantiomeric excess of corresponding (R)-cyanohydrins were obtained as 95-95, 85-79, and 2-25%, respectively, after 96 h at pH 4.0 and 5 °C. For acetophenone, 4-fluoroacetophenone, 4-chloroacetophenone, 4-bromoacetophenone, and 4-iodoacetophenone, the yield-enantiomeric excess of corresponding (R)-cyanohydrins were 1-99, 20-84, 11-95, 5-99, and 3-24%, respectively at the same conditions. The results demonstrate PdHNL-CLEA can be effectively used in the synthesis of (R)-mandelonitrile.

  14. Synthesis, Evaluation of Substituent Effect and Antimicrobial Activities of Substituted (E-1-(3-bromo-4-morpholinophenyl-3-phenylprop-2-en-1-one Compounds

    Directory of Open Access Journals (Sweden)

    Selvaraj Balaji

    2017-04-01

    Full Text Available A series of ten substituted (E-1-(3-bromo-4-morpholinophenyl-3-phenylprop-2-en-1-one compounds were synthesized by Crossed-Aldol condensation of 3-bromo-4-marpholino acetophenone with various substituted and unsubstituted benzaldehydes in presence of sodium hydroxide. The entire ten compounds are novel and these have been newly synthesized compounds. The synthesized substituted 3-phenylprop-2-en-1-one were characterized by their physical constants and UV, IR, NMR spectral data. These observed UV absorption maximum (λmax nm value. The group frequencies of infrared absorption (cm-1 of νCO s-cis and s-trans, deformation modes of νCH out of plane and in-plane, νCH=CH out of plane, ν>C=C

  15. Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.

    Science.gov (United States)

    Nilsson, Anders; Lagesson, Verner; Bornehag, Carl-Gustaf; Sundell, Jan; Tagesson, Christer

    2005-10-01

    A novel technique, gas chromatography-UV spectrometry (GC-UV), was used to quantify volatile organic compounds (VOCs) in settled dust from 389 residences in Sweden. The dust samples were thermally desorbed in an inert atmosphere and evaporated compounds were concentrated by solid phase micro extraction and separated by capillary GC. Eluting compounds were then detected, identified, and quantified using a diode array UV spectrophotometer. Altogether, 28 compounds were quantified in each sample; 24 of these were found in more than 50% of the samples. The compounds found in highest concentrations were saturated aldehydes (C5-C10), furfuryl alcohol, 2,6-di-tert-butyl-4-methylphenol (BHT), 2-furaldehyde, and benzaldehyde. Alkenals were also found, notably 2-butenal (crotonaldehyde), 2-methyl-propenal (methacrolein), hexenal, heptenal, octenal, and nonenal. The concentrations of each of the 28 compounds ranged between two to three orders of magnitude, or even more. These results demonstrate the presence of a number of VOCs in indoor dust, and provide, for the first time, a quantitative determination of these compounds in a larger number of dust samples from residents. The findings also illustrate the potential use of GC-UV for analysing volatile compounds in indoor dust, some of which are potential irritants (to the skin, eyes or respiratory system) if present at higher concentrations. The potential use of GC-UV for improving survey and control of the human exposure to particle-bound irritants and other chemicals is inferred.

  16. Synthesis,

    Directory of Open Access Journals (Sweden)

    Ganesan Vanangamudi

    2017-02-01

    Full Text Available Twelve 2,5-dimethyl-3-thienyl chalcones [E-1-(2,5-dimethyl-3-thienyl-3-(substituted phenyl-2-propen-1-ones] have been synthesized by Claisen–Schmidt condensation of 3-acetyl-2,5-dimethyl furon and substituted benzaldehydes. Yields of the 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, CHCH out of plane, >CC< 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, antioxidant and insect antifeedant activities of these chalcones have been studied.

  17. A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity

    Directory of Open Access Journals (Sweden)

    Sobhi M. Gomha

    2012-08-01

    Full Text Available Successful implementation of ultrasound irradiation for the rapid synthesis of a novel series of 3-[1-(4-substituted-5-(aryldiazenylthiazol-2-ylhydrazonoethyl]-2H-chromen-2-ones 5ah, via reactions of 2-(1-(2-oxo-2H-chromen-3-ylethylidene thiosemicarbazide (2 and the hydrazonoyl halides 3(4, was demonstrated. Also, a new series of 5-arylidene-2-(2-(1-(2-oxo-2H-chromen-3-ylethylidenehydrazinylthiazol-4(5H-ones 10ad were synthesized from reaction of 2 with chloroacetic acid and different aldehydes. Moreover, reaction of 2-cyano-N'-(1-(2-oxo-2H-chromen-3-ylethylidene-acetohydrazide (12 with substituted benzaldehydes gave the respective arylidene derivatives 13ac under the conditions employed. The structures of the synthesized compounds were assigned based on elemental analyses and spectral data. Also, the cytototoxic activities of the thiazole derivative 5a was evaluated against HaCaT cells (human keratinocytes. It was found that compound 5a possess potent cytotoxic activity.

  18. Olfactory memories are intensity specific in larval Drosophila.

    Science.gov (United States)

    Mishra, Dushyant; Chen, Yi-Chun; Yarali, Ayse; Oguz, Tuba; Gerber, Bertram

    2013-05-01

    Learning can rely on stimulus quality, stimulus intensity, or a combination of these. Regarding olfaction, the coding of odour quality is often proposed to be combinatorial along the olfactory pathway, and working hypotheses are available concerning short-term associative memory trace formation of odour quality. However, it is less clear how odour intensity is coded, and whether olfactory memory traces include information about the intensity of the learnt odour. Using odour-sugar associative conditioning in larval Drosophila, we first describe the dose-effect curves of learnability across odour intensities for four different odours (n-amyl acetate, 3-octanol, 1-octen-3-ol and benzaldehyde). We then chose odour intensities such that larvae were trained at an intermediate odour intensity, but were tested for retention with either that trained intermediate odour intensity, or with respectively higher or lower intensities. We observed a specificity of retention for the trained intensity for all four odours used. This adds to the appreciation of the richness in 'content' of olfactory short-term memory traces, even in a system as simple as larval Drosophila, and to define the demands on computational models of associative olfactory memory trace formation. We suggest two kinds of circuit architecture that have the potential to accommodate intensity learning, and discuss how they may be implemented in the insect brain.

  19. Monitoring of lactic fermentation driven by different starter cultures via direct injection mass spectrometric analysis of flavour-related volatile compounds.

    Science.gov (United States)

    Benozzi, Elisabetta; Romano, Andrea; Capozzi, Vittorio; Makhoul, Salim; Cappellin, Luca; Khomenko, Iuliia; Aprea, Eugenio; Scampicchio, Matteo; Spano, Giuseppe; Märk, Tilmann D; Gasperi, Flavia; Biasioli, Franco

    2015-10-01

    In this work, we used Proton Transfer Reaction-Mass Spectrometry (PTR-ToF-MS), coupled with an automated sampling system, to monitor lactic fermentation driven by different yogurt commercial starter cultures via direct injection mass spectrometric analysis of flavour-related volatile compounds. The aim is the identification of markers for real-time and non-invasive bioprocess control and optimisation as an industrial driver of innovation in food technology and biotechnology. We detected more than 300 mass peaks, tentatively identifying all major yogurt aroma volatiles. Thirteen mass peaks showed statistically significant differences among the four commercial starters. Among these are acetaldehyde, methanethiol, butanoic acid, 2-butanone, diacetyl, acetoin, 2-hydroxy-3-pentanone/pentanoic acid, heptanoic acid and benzaldehyde which play a key role in yogurt flavour. These volatile described the diverse flavour properties claimed by food biotechnological companies and, considering the possible contribution to yogurt flavour, are potential markers for the rapid screening of starter cultures and for the quality design in this fermentation-driven production. The strength of our approach lies in the identification, for the first time, of specific depletion kinetics of four sulphur containing compounds occurring during fermentation (hydrogen sulphide, methanethiol, S-methyl thioacetate/S-ethyl thioformate, pentane-thiol), which suggest a new possible protechnological feature of yogurt starter cultures. Copyright © 2015 Elsevier Ltd. All rights reserved.

  20. Phytochemical Analysis of Leaf Extract of Abutilon hirtum (Lam. Sweet by GC-MS Method

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    Vivekraj P.

    2015-08-01

    Full Text Available Abutilon hirtum (Lam. Sweet (Malvaceae commonly known as Vadathuthi. It is used as one of the most important drugs in traditional system of medicine to treat various ailments. The plant is used for to its various properties as demulcent, diuretics, anti-diabetics, anthelmintic, laxative, wound healing properties, antibacterial and antifungal properties. The present study revealed the presence of phytochemicals like Diethyl Phthalate (19.171%,Benzaldehyde 4-propyl (5.219%,Methoxyacetic acid 3-tridecyl ester (5.196%,Sulfurous acid dodecyl 2-propyl ester (0.455%,Sulfurous acid, butyl dodecyl ester (0.442%etc., from the chloroform extracts of leaves in A. hirtum. In the present study an attempt was made to investigate the phytochemical present in the extracts in the preliminary level by using Gas Chromatography coupled with Mass Spectrometry (GC-MS. The study will provide information for the correct identification of the crude drug. This will be further considered for pharmacological activities and isolation of individual components would however, help to find new drugs.The results are reported for the first time in A. hirtum.

  1. Characterization of Morphology, Volatile Profiles, and Molecular Markers in Edible Desert Truffles from the Negev Desert.

    Science.gov (United States)

    Kamle, Madhu; Bar, Einat; Lewinsohn, Dalia; Shavit, Elinoar; Roth-Bejerano, Nurit; Kagan-Zur, Varda; Barak, Ze'ev; Guy, Ofer; Zaady, Eli; Lewinsohn, Efraim; Sitrit, Yaron

    2017-03-28

    Desert truffles are mycorrhizal, hypogeous fungi considered a delicacy. On the basis of morphological characters, we identified three desert truffle species that grow in the same habitat in the Negev desert. These include Picoa lefebvrei (Pat.), Tirmania nivea (Desf.) Trappe, and Terfezia boudieri (Chatain), all associated with Helianthemum sessiliflorum. Their taxonomy was confirmed by PCR-RFLP. The main volatiles of fruit bodies of T. boudieri and T. nivea were 1-octen-3-ol and hexanal; however, volatiles of the latter species further included branched-chain amino acid derivatives such as 2-methylbutanal and 3-methylbutanal, phenylalanine derivatives such as benzaldehyde and benzenacetaldehyde, and methionine derivatives such as methional and dimethyl disulfide. The least aromatic truffle, P. lefebvrei, contained low levels of 1-octen-3-ol as the main volatile. Axenic mycelia cultures of T. boudieri displayed a simpler volatile profile compared to its fruit bodies. This work highlights differences in the volatile profiles of desert truffles and could hence be of interest for selecting and cultivating genotypes with the most likable aroma.

  2. New Bis-Pyrazolones as Potential Leads for ROS Inhibition; Environment Friendly Green Synthesis, Structural Characterization, and In Vitro Studies.

    Science.gov (United States)

    Yousuf, Sahar; Khan, Khalid Mohammed; Salar, Uzma; Jabeen, Almas; Ahmed, Shakil; Muhammad, Munira Taj; Faheem, Aisha; Perveen, Shahnaz

    2018-01-12

    Pyrazolones have identified as significant antioxidant agents and many marketed and clinically prescribed NSAIDs have pyrazolone ring as main scaffold. Keeping in consideration the antioxidant potential of pyrazolone scaffold, new bis-pyrazolones 3-30 were synthesized by a green and enviroment friendly reaction route, in which two equivalents of 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-ol were treated with one equivalent of benzaldehyde derivatives without any catalyst. All compounds were structurally characterzied by 1H-NMR and FAB analysis. 13C-NMR of selected compounds was also recorded. All compounds gave satisfactory elemental analyses and found in good agreement with calculated values. Synthetic bis-pyrazolones 3-30 were evaluated for their oxidative burst inhibitory effect of zymosan stimulated whole blood phagocytes by using luminol enhanced chemilluminescence technique. All molecules demonstrated the potent ROS inhibition activity in the range of IC50 = 1.2 ± 0.1-48.8 ± 3.9 µM as compared to the standard ibuprofen (IC50 = 54.2 ± 9.2 µM). The purity of active compounds was checked by HPLC. This study has identified a number of non-acidic lead molecules for future research on ROS inhibitors. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  3. Sol-gel based sensor for selective formaldehyde determination

    International Nuclear Information System (INIS)

    Bunkoed, Opas; Davis, Frank; Kanatharana, Proespichaya; Thavarungkul, Panote; Higson, Seamus P.J.

    2010-01-01

    We report the development of transparent sol-gels with entrapped sensitive and selective reagents for the detection of formaldehyde. The sampling method is based on the adsorption of formaldehyde from the air and reaction with β-diketones (for example acetylacetone) in a sol-gel matrix to produce a yellow product, lutidine, which was detected directly. The proposed method does not require preparation of samples prior to analysis and allows both screening by visual detection and quantitative measurement by simple spectrophotometry. The detection limit of 0.03 ppmv formaldehyde is reported which is lower than the maximum exposure concentrations recommended by both the World Health Organisation (WHO) and the Occupational Safety and Health Administration (OSHA). This sampling method was found to give good reproducibility, the relative standard deviation at 0.2 and 1 ppmv being 6.3% and 4.6%, respectively. Other carbonyl compounds i.e. acetaldehyde, benzaldehyde, acetone and butanone do not interfere with this analytical approach. Results are provided for the determination of formaldehyde in indoor air.

  4. A deep transcriptomic analysis of pod development in the vanilla orchid (Vanilla planifolia).

    Science.gov (United States)

    Rao, Xiaolan; Krom, Nick; Tang, Yuhong; Widiez, Thomas; Havkin-Frenkel, Daphna; Belanger, Faith C; Dixon, Richard A; Chen, Fang

    2014-11-07

    Pods of the vanilla orchid (Vanilla planifolia) accumulate large amounts of the flavor compound vanillin (3-methoxy, 4-hydroxy-benzaldehyde) as a glucoside during the later stages of their development. At earlier stages, the developing seeds within the pod synthesize a novel lignin polymer, catechyl (C) lignin, in their coats. Genomic resources for determining the biosynthetic routes to these compounds and other flavor components in V. planifolia are currently limited. Using next-generation sequencing technologies, we have generated very large gene sequence datasets from vanilla pods at different times of development, and representing different tissue types, including the seeds, hairs, placental and mesocarp tissues. This developmental series was chosen as being the most informative for interrogation of pathways of vanillin and C-lignin biosynthesis in the pod and seed, respectively. The combined 454/Illumina RNA-seq platforms provide both deep sequence coverage and high quality de novo transcriptome assembly for this non-model crop species. The annotated sequence data provide a foundation for understanding multiple aspects of the biochemistry and development of the vanilla bean, as exemplified by the identification of candidate genes involved in lignin biosynthesis. Our transcriptome data indicate that C-lignin formation in the seed coat involves coordinate expression of monolignol biosynthetic genes with the exception of those encoding the caffeoyl coenzyme A 3-O-methyltransferase for conversion of caffeoyl to feruloyl moieties. This database provides a general resource for further studies on this important flavor species.

  5. Microwave-Assisted Synthesis of Nickel Oxide Nanoparticles Using Coriandrum sativum Leaf Extract and Their Structural-Magnetic Catalytic Properties

    Directory of Open Access Journals (Sweden)

    Ramakrishnan Azhagu Raj

    2017-04-01

    Full Text Available In this paper, using Coriandrum sativum L., a leaf-extracted, assisted microwave method (MM was used to synthesize nickel oxide formation. We synthesized nickel oxide nanoparticles (NiO with a crystal size in the range of 15–16 nm by a Coriandrum sativum leaf-assisted microwave method (LAMM. The synthesized materials show that an X-ray diffraction (XRD study confirmed the formation of a single phase structure exhibiting a crystallite size in the range of 15–16 nm using Scherrer’s method. The nickel oxide prepared by the MM had a surface area of 60.35 m2/g, pore volume of 0.9427 cm3/g and an average pore diameter of 13.27 Å. Surface morphology was analyzed by the scanning electron microscope (SEM, X-ray photoelectron spectroscope, Brunauer-Emmett-Teller (BET analysis, and the vibrating sample magnetometer (VSM. Catalytic activity (CA tended toward the oxidation of styrene to benzaldehyde. The inexpensive catalyst tested is likely effective as a catalyst due to synergistic interactions between metal oxides with high dispersion. In comparison with other findings, LAMM is easy and eco-friendly. The current study obtained nanocrystalline NiO that was suitable for potential applications in catalysis. The synthesized NiO could potentially be used in therapeutic field due to their competent antibacterial activity.

  6. Effect of extraction and concentration processes on properties of longan syrup.

    Science.gov (United States)

    Surin, Siriluck; Thakeow, Prodpran; Seesuriyachan, Phisit; Angeli, Sergio; Phimolsiripol, Yuthana

    2014-09-01

    Longan (Dimocarpus longan Lour.) syrup is a novel liquid sweetener produced from longan, one of the traditional and economic fruits in the Northern of Thailand. In this research, the effect of extraction and concentration processes on properties of longan syrup was investigated. There were two extraction methods (juice extractor and hydraulic press) and three concentration methods (direct heating, steam heating and vacuum evaporation). Results overall showed that the extraction method had no significant (p ≥ 0.05) effect on longan syrup properties, while concentration resulted in the quality changes of longan syrup. Concentration using direct heating of longan juice caused reduction of sucrose content, and longan syrup dark in color. The headspace volatile compounds of longan syrup were sampled using direct headspace technique and further characterized using gas chromatography-mass spectrometry. The identified volatile compounds could be divided into two groups of aroma characteristics which were (1) floral aroma: 3-methybutyl acetate, (β)-ocimene and 2-phenylethyl alcohol and (2) caramel aroma: butyraldehyde, furfural and benzaldehyde. 2-Phenylethyl alcohol, contributing to floral odor, was retained using vacuum evaporation as a concentration method. Result revealed that the optimal concentration process for longan syrup production was vacuum evaporation, providing the highest floral volatile and lowest caramel volatile. Sensory tests confirmed that longan flavor of the syrup produced from the vacuum evaporation process had significantly higher hedonic scores than other processes.

  7. New fluorescent azo-Schiff base Cu(II) and Zn(II) metal chelates; spectral, structural, electrochemical, photoluminescence and computational studies

    Science.gov (United States)

    Purtas, Fatih; Sayin, Koray; Ceyhan, Gokhan; Kose, Muhammet; Kurtoglu, Mukerrem

    2017-06-01

    A new Schiff base containing azo chromophore group obtained by condensation of 2-hydroxy-4-[(E)-phenyldiazenyl]benzaldehyde with 3,4-dimethylaniline (HL) are used for the syntheses of new copper(II) and zinc(II) chelates, [Cu(L)2], and [Zn(L)2], and characterized by physico-chemical and spectroscopic methods such as 1H and 13C NMR, IR, UV.-Vis. and elemental analyses. The solid state structure of the ligand was characterized by single crystal X-ray diffraction study. X-ray diffraction data was then used to calculate the harmonic oscillator model of aromaticity (HOMA) indexes for the rings so as to investigate of enol-imine and keto-amine tautomeric forms in the solid state. The phenol ring C10-C15 shows a considerable deviation from the aromaticity with HOMA value of 0.837 suggesting the shift towards the keto-amine tautomeric form in the solid state. The analytical data show that the metal to ligand ratio in the chelates was found to be 1:2. Theoretical calculations of the possible isomers of the ligand and two metal complexes are performed by using B3LYP method. Electrochemical and photoluminescence properties of the synthesized azo-Schiff bases were also investigated.

  8. Physico-chemical properties and sensory profile of durum wheat Dittaino PDO (Protected Designation of Origin) bread and quality of re-milled semolina used for its production.

    Science.gov (United States)

    Giannone, Virgilio; Giarnetti, Mariagrazia; Spina, Alfio; Todaro, Aldo; Pecorino, Biagio; Summo, Carmine; Caponio, Francesco; Paradiso, Vito Michele; Pasqualone, Antonella

    2018-02-15

    To help future quality checks, we characterized the physico-chemical and sensory properties of Dittaino bread, a sourdough-based durum wheat bread recently awarded with Protected Designation of Origin mark, along with the quality features of re-milled semolina used for its production. Semolina was checked for Falling Number (533-644s), protein content (12.0-12.3g/100gd.m.), gluten content (9.7-10.5g/100gd.m.), yellow index (18.0-21.0), water absorption (59.3-62.3g/100g), farinograph dough stability (171-327s), softening index (46-66B.U.), alveograph W (193×10 -4 -223×10 -4 J) and P/L (2.2-2.7). Accordingly, bread crumb was yellow, moderately hard (16.4-27.1N) and chewy (88.2-109.2N×mm), with low specific volume (2.28-3.03mL/g). Bread aroma profile showed ethanol and acetic acid, followed by hexanol, 3-methyl-1-butanol, 2-phenylethanol, 3-methylbutanal, hexanal, benzaldehyde, and furfural. The sensory features were dominated by a thick brown crust, with marked toasted odor, coupled to yellow and consistent crumb, with coarse grain and well-perceivable sour taste and odor. Copyright © 2017 Elsevier Ltd. All rights reserved.

  9. A novel NADPH-dependent aldehyde reductase gene from Vigna radiata confers resistance to the grapevine fungal toxin eutypine.

    Science.gov (United States)

    Guillén, P; Guis, M; Martínez-Reina, G; Colrat, S; Dalmayrac, S; Deswarte, C; Bouzayen, M; Roustan, J P; Fallot, J; Pech, J C; Latché, A

    1998-11-01

    Eutypine, 4-hydroxy-3-(3-methyl-3-butene-1-ynyl) benzyl aldehyde, is a toxin produced by Eutypa lata, the causal agent of eutypa dieback of grapevines. It has previously been demonstrated that tolerance of some cultivars to this disease was correlated with their capacity to convert eutypine to the corresponding alcohol, eutypinol, which lacks phytotoxicity. We have thus purified to homogeneity a protein from Vigna radiata that exhibited eutypine-reducing activity and have isolated the corresponding cDNA. This encodes an NADPH-dependent reductase of 36 kDa that we have named Vigna radiata eutypine-reducing enzyme (VR-ERE), based on the capacity of a recombinant form of the protein to reduce eutypine into eutypinol. The strongest homologies (86.8%) of VR-ERE at the amino acid level were found with CPRD14, a drought-inducible gene of unknown function, isolated from Vigna unguiculata and with an aromatic alcohol dehydrogenase (71.7%) from Eucalyptus gunnii. Biochemical characterization of VR-ERE revealed that a variety of compounds containing an aldehyde group can act as substrates. However, the highest affinity was observed with 3-substituted benzaldehydes. Expression of a VR-ERE transgene in Vitis vinifera cells cultured in vitro conferred resistance to the toxin. This discovery opens up new biotechnological approaches for the generation of grapevines resistant to eutypa dieback.

  10. Volatiles from a Rare Acer spp. Honey Sample from Croatia

    Directory of Open Access Journals (Sweden)

    Igor Jerković

    2010-06-01

    Full Text Available A rare sample of maple (Acer spp. honey from Croatia was analysed. Ultrasonic solvent extraction (USE using: 1 pentane, 2 diethyl ether, 3 a mixture of pentane and diethyl ether (1:2 v/v and 4 dichloromethane as solvents was applied. All the extracts were analysed by GC and GC/MS. The most representative extracts were 3 and 4. Syringaldehyde was the most striking compound, being dominant in the extracts 2, 3 and 4 with percentages 34.5%, 33.1% and 35.9%, respectively. In comparison to USE results of other single Croatian tree honey samples (Robinia pseudoacacia L. nectar honey, Salix spp. nectar and honeydew honeys, Quercus frainetto Ten. honeydew as well as Abies alba Mill. and Picea abies L. honeydew and literature data the presence of syringaldehyde, previously identified in maple sap and syrup, can be pointed out as a distinct characteristic of the Acer spp. honey sample. Headspace solid-phase microextraction (HS-SPME combined with GC and GC/MS identified benzaldehyde (16.5%, trans-linalool oxide (20.5% and 2-phenylethanol (14.9% as the major compounds that are common in different honey headspace compositions.

  11. Comparative Analysis of Three Types of Peaches: Identification of the Key Individual Characteristic Flavor Compounds by Integrating Consumers' Acceptability with Flavor Quality

    Directory of Open Access Journals (Sweden)

    Wanpeng XI

    2017-01-01

    Full Text Available In order to recognize the key flavor compounds influencing the consumers' choice for honey peach, nectarine, and flat peach and provide important information for orientation breeding, sugars, organic acids, and aroma volatiles in 3 types of peaches were examined by high performance liquid chromatography (HPLC and gas chromatography–mass spectrometry (GC–MS and their key individual characteristic flavor compounds were identified by multivariate analysis integrated with consumers' evaluation. No significant differences in sugar and organic acid were observed between 3 types of peaches. In hierarchical clustering analysis (HCA and principal component analysis (PCA models, 3 types of peaches could not be differentiated by sugars or organic acids, but could be identified completely by aroma volatiles or by flavor compounds. A partial least squares regression (PLSR model revealed that the key individual characteristic volatiles in nectarine, honey peach, and flat peach are C9 compounds and terpenic compounds, norisoprenoids and C6 compounds, and benzaldehyde, γ-decalactone, and δ-dodecalactone, respectively. These results suggest that sugars and organic acids form the background flavor of peach fruit and lactones shape the typical peach aroma. However, the individual aroma volatiles play the decisive role in unique flavor determination of different types of peaches.

  12. A vanillin derivative causes mitochondrial dysfunction and triggers oxidative stress in Cryptococcus neoformans.

    Directory of Open Access Journals (Sweden)

    Jin Hyo Kim

    Full Text Available Vanillin is a well-known food and cosmetic additive and has antioxidant and antimutagenic properties. It has also been suggested to have antifungal activity against major human pathogenic fungi, although it is not very effective. In this study, the antifungal activities of vanillin and 33 vanillin derivatives against the human fungal pathogen Cryptococcus neoformans, the main pathogen of cryptococcal meningitis in immunocompromised patients, were investigated. We found a structural correlation between the vanillin derivatives and antifungal activity, showing that the hydroxyl or alkoxy group is more advantageous than the halogenated or nitrated group in benzaldehyde. Among the vanillin derivatives with a hydroxyl or alkoxy group, o-vanillin and o-ethyl vanillin showed the highest antifungal activity against C. neoformans. o-Vanillin was further studied to understand the mechanism of antifungal action. We compared the transcriptome of C. neoformans cells untreated or treated with o-vanillin by using RNA sequencing and found that the compound caused mitochondrial dysfunction and triggered oxidative stress. These antifungal mechanisms of o-vanillin were experimentally confirmed by the significantly reduced growth of the mutants lacking the genes involved in mitochondrial functions and oxidative stress response.

  13. Bis(μ-oxo) dicopper(III) species of the simplest peralkylated diamine: enhanced reactivity toward exogenous substrates.

    Science.gov (United States)

    Kang, Peng; Bobyr, Elena; Dustman, John; Hodgson, Keith O; Hedman, Britt; Solomon, Edward I; Stack, T Daniel P

    2010-12-06

    N,N,N',N'-tetramethylethylenediamine (TMED), the simplest and most extensively used peralkylated diamine ligand, is conspicuously absent from those known to form a bis(μ-oxo)dicopper(III) (O) species, [(TMED)(2)Cu(III)(2)(μ(2)-O)(2)](2+), upon oxygenation of its Cu(I) complex. Presented here is the characterization of this O species and its reactivity toward exogenous substrates. Its formation is complicated both by the instability of the [(TMED)Cu(I)](1+) precursor and by competitive formation of a presumed mixed-valent trinuclear [(TMED)(3)Cu(III)Cu(II)(2)(μ(3)-O)(2)](3+) (T) species. Under most reaction conditions, the T species dominates, yet, the O species can be formed preferentially (>80%) upon oxygenation of acetone solutions, if the copper concentration is low (theory (DFT) computational methods for geometry optimization and spectroscopic predictions. The enhanced thermal stability of [(TMED)(2)Cu(III)(2)(μ(2)-O)(2)](2+) and its limited steric demands compared to other O species allows more efficient oxidation of exogenous substrates, including benzyl alcohol to benzaldehyde (80% yield), highlighting the importance of ligand structure to not only enhance the oxidant stability but also maintain accessibility to the nascent metal/O(2) oxidant.

  14. Synthesis, characterization and evaluation of green catalytic activity of nano Ag–Pt doped silicate

    International Nuclear Information System (INIS)

    Murugavelu, M.; Karthikeyan, B.

    2013-01-01

    Highlights: ► Nanosized Ag–Pt loaded SiO 2 was prepared by sol–gel method. ► This catalyst has been characterized by different techniques. ► Catalyst induces the reaction of condensation of indole and aldehyde in lesser time. ► The coupled product is confirmed by spectral and DFT theoretical methods. - Abstract: In order to get materials with enhanced adsorption and organic transformation performance, nanosized Ag–Pt nanoparticles loaded SiO 2 was prepared by sol–gel method. This catalyst has been characterized by Fourier transform infrared (FT-IR) spectra, diffuse reflectance spectra (DRS), fluorescence, high-resolution scanning electron microscopy (HR-SEM), X-ray diffraction (XRD), transmission electron microscopy (TEM) and atomic force microscopy (AFM). Ag–Pt/SiO 2 catalyst induces the reaction of condensation of indole and aldehyde to give bis(indolyl)methanes in striking lesser time under microwave (MW) irradiation and it has been examined with different substituted benzaldehydes. The coupled product is confirmed by FT-IR, 1 H, 13 C NMR and DFT theoretical methods.

  15. Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity

    Directory of Open Access Journals (Sweden)

    Ajmal R. Bhat

    2015-11-01

    Full Text Available An efficiently simple protocol for the synthesis of methyl 7 amino-4-oxo-5-phenyl-2-thioxo-2, 3, 4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates via one-pot three component condensation pathway is established via microwave irradiation using varied benzaldehyde derivatives, methylcyanoacetate and thio-barbituric acid in water as a green solvent. A variety of functionalized substrates were found to react under this methodology due to its easy operability and offers several advantages like, high yields (78–94%, short reaction time (3–6 min, safety and environment friendly without used any catalyst. The synthesized compounds (4a–4k showed comparatively good in vitro antimicrobial and antifungal activities against different strains. The Compounds 4a, 4b, 4c, 4d 4e and 4f showed maximum antimicrobial activity against Staphylococcus aureus, Bacillus cereus (gram-positive bacteria, Escherichia coli, Klebshiella pneumonia, Pseudomonas aeruginosa (gram-negative bacteria. The synthesized compound 4f showed maximum antifungal activity against Aspergillus Niger and Penicillium chrysogenum strains. Streptomycin is used as standard for bacterial studies and Mycostatin as standards for fungal studies. Structure of all newly synthesized products was characterized on the basis of IR, 1H NMR, 13C NMR and mass spectral analysis.

  16. Synthesis, characterization and heterogeneous base catalysis of amino functionalized lanthanide metal-organic frameworks

    Science.gov (United States)

    Huang, Jinping; Li, Chunmei; Tao, Lingling; Zhu, Huilin; Hu, Gang

    2017-10-01

    Lanthanide metal-organic frameworks (Ln-MOFs) are featured by their tolerance to water and dense structure. In this work, an amine-functionalized Ln-MOF was facilely synthesized by coordination of terbium with 2-aminoterephthalic acid under the condition of microwave irradiation. The crystal structure was characterized by single crystal X-ray diffraction, FT-IR, Raman, TG-DTA and XPS analysis. The basic catalytic activity of the NH2-Tb-MOF was evaluated for Knoevenagel condensation and Henry reactions. Apart from the high activity and 100% selectivity to the condensation product, the NH2-Tb-MOF catalyst could be easily recycled and reused owing to the high stability of the MOF framework formed by coordination of Tb3+ with carboxylic groups. Remarkably, the NH2-Tb-MOF exhibited size-selective catalysis to substrates. For the small-sized reactants, it displayed comparable activity to the homogeneous catalyst of aniline owing to the high dispersion of NH2- active sites and the low diffusion limits. However, in the same reaction system, extremely poor activity in Knoevenagel condensation and Henry reaction for the bulky substrate 4-(tert-butyl) benzaldehyde was observed due to the both effects of substitute and inhibition of diffusion into the micropores. Crystal structure analysis provided a mechanistic evidence that the heterogeneous base catalysis arose from the amino groups densely distributed inside the micropores.

  17. Functionalized SBA-15 supported nickel (II)–oxime–imine catalysts for liquid phase oxidation of olefins under solvent-free conditions

    Energy Technology Data Exchange (ETDEWEB)

    Paul, Luna [Department of Chemistry, Jadavpur University, Kolkata 700 032 (India); Banerjee, Biplab [Department of Materials Science, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032 (India); Bhaumik, Asim, E-mail: msab@iacs.res.in [Department of Materials Science, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032 (India); Ali, Mahammad, E-mail: m_ali2062@yahoo.com [Department of Chemistry, Jadavpur University, Kolkata 700 032 (India)

    2016-05-15

    A new oxime–imine functionalized highly ordered mesoporous SBA-15 (SBA-15-NH{sub 2}-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(ClO{sub 4}){sub 2} to yield the functionalized nickel catalyst SBA-15-NH{sub 2}-DAMO-Ni. All the synthesized materials were thoroughly characterized using different characterization techniques. It was found that SBA-15-NH{sub 2}-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. - Graphical abstract: A new well characterized oxime–imine functionalized highly ordered mesoporous SBA-15-NH{sub 2}-DAMO-Ni complex catalyzes the one-pot oxidation of olefins under solvent free mild conditions.

  18. Response of female Cydia molesta (Lepidoptera: Tortricidae) to plant derived volatiles.

    Science.gov (United States)

    Dorn, S; Natale, D; Mattiacci, L; Hern, A; Pasqualini, E; Dorn, S

    2003-08-01

    Peach shoot volatiles were attractive to mated female oriental fruit moth, Cydia molesta (Busck), in a dual choice arena. No preference was observed between leaf odours from the principle host plant, peach, and the secondary host plant, apple. Twenty-two compounds were identified in headspace volatiles of peach shoots using gas chromatography-mass spectrometry. Green leaf volatiles accounted for more than 50% of the total emitted volatiles. A bioassay-assisted fractionation using different sorbent polymers indicated an attractant effect of compounds with a chain length of 6-8 carbon atoms. The major compounds of this fraction were tested either singly or in combinations for behavioural response of females. Significant bioactivity was found for a three-component mixture of (Z)-3-hexen-1-yl acetate, (Z)-3-hexen-1-ol and benzaldehyde in a 4:1:1 ratio. This synthetic mixture elicited a similar attractant effect as the full natural blend from peach shoots as well as the bioactive fraction.

  19. Monitoring of selected skin- and breath-borne volatile organic compounds emitted from the human body using gas chromatography ion mobility spectrometry (GC-IMS).

    Science.gov (United States)

    Mochalski, Paweł; Wiesenhofer, Helmut; Allers, Maria; Zimmermann, Stefan; Güntner, Andreas T; Pineau, Nicolay J; Lederer, Wolfgang; Agapiou, Agapios; Mayhew, Christopher A; Ruzsanyi, Veronika

    2018-02-15

    Human smuggling and associated cross-border crimes have evolved as a major challenge for the European Union in recent years. Of particular concern is the increasing trend of smuggling migrants hidden inside shipping containers or trucks. Therefore, there is a growing demand for portable security devices for the non-intrusive and rapid monitoring of containers to detect people hiding inside. In this context, chemical analysis of volatiles organic compounds (VOCs) emitted from the human body is proposed as a locating tool. In the present study, an in-house made ion mobility spectrometer coupled with gas chromatography (GC-IMS) was used to monitor the volatile moieties released from the human body under conditions that mimic entrapment. A total of 17 omnipresent volatile compounds were identified and quantified from 35 ion mobility peaks corresponding to human presence. These are 7 aldehydes (acrolein, 2-methylpropanal, 3-methylbutanal, 2-ethacrolein, n-hexanal, n-heptanal, benzaldehyde), 3 ketones (acetone, 2-pentanone, 4-methyl-2-pentanone), 5 esters (ethyl formate, ethyl propionate, vinyl butyrate, butyl acetate, ethyl isovalerate), one alcohol (2-methyl-1-propanol) and one organic acid (acetic acid). The limits of detection (0.05-7.2 ppb) and relative standard deviations (0.6-11%) should be sufficient for detecting these markers of human presence in field conditions. This study shows that GC-IMS can be used as a portable field detector of hidden or entrapped people. Copyright © 2018 Elsevier B.V. All rights reserved.

  20. Yogurt produced with cajuí (Anacardium othonianum Rizz

    Directory of Open Access Journals (Sweden)

    Camila Martins Fonseca

    2014-09-01

    Full Text Available Yogurt added with 0%, 5%, 10%, 15% and 20% of cajuí pulp (Anacardium othonianum Rizz were characterized. Acidity, pH, protein, dry matter, firmness, consistency, cohesiveness and quantification of lactic acid bacteria were conducted at 0, 10, 20 and 30 days. Identification of volatiles compounds and sensory tests of preference, acceptance and consumption intention were performed on the first day of shelf-life. Preferred formulations are those that contain smaller proportions of pulp (5% which coincide with lower acidity. There was no significant effect (P>0.05 of the amount of pulp added and storage time on dry matter, lactic acid bacteria count, firmness, consistency and cohesiveness. Acidity and pH were significantly influenced (P <0.05 by the amount of pulp added and storage time. Protein levels were significantly lower (P <0.05 with the increase in the quantity of pulp added. Volatiles compounds in cajuí yogurt include ethyl butanoate, methyl butanoate, ethanol, hexanal, benzaldehyde and 3-methyl butanoate. There are technological potential in the production of yoghurt with cajuí with addition of 5% in proportion to the total volume of yogurt produced.

  1. Synthesis, antifungal evaluation and in silico study of novel Schiff bases derived from 4-amino-5(3,5-dimethoxy-phenyl-4H-1,2,4-triazol-3-thiol

    Directory of Open Access Journals (Sweden)

    N.S. Hari Narayana Moorthy

    2017-05-01

    Full Text Available A novel series of Schiff bases based on of 4-amino-5-(3,5-dimethoxy-phenyl-4H-1,2,4-triazol-3-thiol scaffold was prepared by heating thiocarbohydrazide and 3,5,-dimethoxy benzoic acid at the temperature above its meting point, and subsequently, treating with substituted benzaldehydes. The chemical constituents in the synthesized compounds were confirmed by IR, Mass, 1H NMR spectroscopy and elemental analysis and the antifungal activity was evaluated against Candida albicans. The structure activity relationship analysis shows that the chloride substituted derivatives possess promising activity in micromolar concentration and also the hydroxy phenyl derivatives exhibited considerable activity at 128 μg/ml. But other compounds with amino, furan and methoxy substitutions did not show antifungal activity till the concentration of 512 μg/ml. In silico pharmacokinetic prediction shows that all the compounds obeyed Lipinski rule of 5 and are free of toxicity and metabolically stable. Pharmacophore analysis revealed that the aromatic/hydrophobic and aromatic/acceptor/donor features in the compounds are essential for the activity. The predicted cardiotoxicity (hERG and lethal effect of the synthesized compounds will permit us to carry out further in vitro and in vivo toxicity studies.

  2. Microbial biodiesel production from oil palm biomass hydrolysate using marine Rhodococcus sp. YHY01.

    Science.gov (United States)

    Bhatia, Shashi Kant; Kim, Junyoung; Song, Hun-Seok; Kim, Hyun Joong; Jeon, Jong-Min; Sathiyanarayanan, Ganesan; Yoon, Jeong-Jun; Park, Kyungmoon; Kim, Yun-Gon; Yang, Yung-Hun

    2017-06-01

    The effect of various biomass derived inhibitors (i.e. furfural, hydroxymethylfurfural (HMF), vanillin, 4-hydroxy benzaldehyde (4-HB) and acetate) was investigated for fatty acid accumulation in Rhodococcus sp. YHY 01. Rhodococcus sp. YHY01 was able to utilize acetate, vanillin, and 4-HB for biomass production and fatty acid accumulation. The IC 50 value for furfural (3.1mM), HMF (3.2mM), vanillin (2.0mM), 4-HB (2.7mM) and acetate (3.7mM) was calculated. HMF and vanillin affect fatty acid composition and increase saturated fatty acid content. Rhodococcus sp. YHY 01 cultured with empty fruit bunch hydrolysate (EFBH) as the main carbon source resulted in enhanced biomass (20%) and fatty acid productivity (37%), in compression to glucose as a carbon source. Overall, this study showed the beneficial effects of inhibitory molecules on growth and fatty acid production, and support the idea of biomass hydrolysate utilization for biodiesel production by avoiding complex efforts to remove inhibitory compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

  3. Synthesis of novel fluorinated chalcones derived from 4‧-morpholinoacetophenone and their antiproliferative effects

    Science.gov (United States)

    Kurşun Aktar, Bedriye Seda; Oruç-Emre, Emine Elçin; Demirtaş, Ibrahim; Yaglioglu, Ayse Sahin; Guler, Caglar; Adem, Sevki; Karaküçük Iyidoğan, Ayşegül

    2017-12-01

    The fluorinated chalcones were synthesized by Claisen-Schmidt condensation between 4‧-morpholineacetophenone and various fluorinated benzaldehydes in the presence of NaOH in methanol. The synthesized compounds [1-7] were evaluated their antiproliferative activity against HeLa and C6 cell lines. Among them, compounds 4 and 5 were determined to have anticancer activity against HeLa cells line (IC50 values of 7.74 and 6.10 μg/mL, respectively). The anticancer activity results were shown that compounds 3, and 6 had inhibitory against C6 cells (IC50 values of 12.80 and 4.16 μg/mL, respectively). The compounds 1 and 2 had high antiproliferative activity with non-cytotoxicity. All of the new compounds, except for compound 4 showed inhibition against the human isozyme hCA I with IC50 in the range of 0.5-1,16 mM. Pyruvate kinase M2 (PKM2) was effectively inhibited by compound 4 with IC50 = 26 μM.

  4. Synthesis and Anticancer Activity of Some Novel Tetralin-6-yl-pyrazoline, 2-Thioxopyrimidine, 2-Oxopyridine, 2-Thioxo-pyridine and 2-Iminopyridine Derivatives

    Directory of Open Access Journals (Sweden)

    Ebtehal S. Al-Abdullah

    2011-04-01

    Full Text Available The title compounds were prepared by reaction of 6-acetyltetralin (1 with different aromatic aldehydes 2a-c, namely 2,6-dichlorobenzaldehyde, 2,6-diflouro-benzaldehyde, and 3-ethoxy-4-hydroxybenzaldehyde, to yield the corresponding a,b-unsaturated ketones 3a-c. Compound 3b was reacted with hydrazine hydrate to yield the corresponding 2-pyrazoline 4, while compounds 3a,b reacted with thiourea to afford the 2-thioxopyrimidine derivatives 5a,b, respectively. The reaction of 1, and the aromatic aldehydes 2a-c with ethyl cyanoacetate, 2-cyano-thioacetamide or malononitrile in the presence of ammonium acetate yielded the corresponding 2-oxopyridines 6a,b, 2-thioxopyridines 7a-c or 2-iminopyridines 8a,b, respectively. The newly prepared compounds were evaluated for anticancer activity against two human tumor cell lines. Compound 3a showed the highest potency with IC50 = 3.5 and 4.5 μg/mL against a cervix carcinoma cell line (Hela and breast carcinoma cell line (MCF7, respectively.

  5. Biodegradation of kraft lignin by a bacterial strain Comamonas sp. B-9 isolated from eroded bamboo slips.

    Science.gov (United States)

    Chen, Y H; Chai, L Y; Zhu, Y H; Yang, Z H; Zheng, Y; Zhang, H

    2012-05-01

    The aim was to obtain evidences for lignin degradation by unicellular bacterium Comamonas sp. B-9. Comamonas sp. B-9 was inoculated into kraft lignin-mineral salt medium (KL-MSM) at pH 7·0 and 30°C for 7 days of incubation. The bacterial growth, chemical oxygen demand (COD) reduction, secretion of ligninolytic enzymes and productions of low-molecular-weight compounds revealed that Comamonas sp. B-9 was able to degrade kraft lignin (KL). COD in KL-MSM reduced by 32% after 7 days of incubation. The maximum activities of manganese peroxidase (MnP) of 2903·2 U l(-1) and laccase (Lac) of 1250 U l(-1) were observed at 4th and 6th day, respectively. The low-molecular-weight compounds such as ethanediol, 3, 5-dimethyl-benzaldehyde and phenethyl alcohol were formed in the degradation of KL by Comamonas sp. B-9 based on GC-MS analysis. This study confirmed that Comamonas sp. B-9 could utilize KL as a sole carbon source and degrade KL to low-molecular-weight compounds. Comamonas sp. B-9 may be useful in the utilization and bioconversion of lignin and lignin-derived aromatic compounds in biotechnological applications. Meanwhile, using Comamonas sp. B-9 in treatment of wastewater in pulp and paper industry is a meaningful work. © 2012 The Authors. Journal of Applied Microbiology © 2012 The Society for Applied Microbiology.

  6. Liquid crystalline polymers IX Main chain thermotropic poly (azomethine – ethers containing thiazole moiety linked with polymethylene spacers

    Directory of Open Access Journals (Sweden)

    2007-04-01

    Full Text Available A new homologous series of thermally stable thermotropic liquid crystalline poly(azomethine-ethers based on thiazole moiety were synthesized by solution polycondensation of 4,4`-diformyl-α,ω-diphenoxyalkanes, I–IV or 4,4`-diformyl-2,2`-dimethoxy-α,ω-diphenoxyalkanes V–VIII with the new bis(2-aminothiazole monomer X. A model compound XI was synthesized from X with benzaldehyde and characterized by elemental and spectral analyses. The inherent viscosities of the resulting polymers were in the range 0.43–1.34 dI/g. All the poly(azomethine-ethers were insoluble in common organic solvents but dissolved completely in concentrated H2SO4 and formic acid. The mesomorphic properties of these polymers were studied as a function of the diphenoxyalkane space length. Their thermotropic liquid crystalline properties were examined by DSC and optical polarizing microscopy and demonstrated that the resulting polymers form nematic mesophases over wide temperature ranges. The thermogravimetric analyses of those polymers were evaluated by TGA and DSC measurements and correlated to their structural units. X-ray analysis showed that polymers having some degree of crystallinity in the region 2θ = 5–60°. In addition, the morphological properties of selected examples were tested by scanning electron microscopy.

  7. Tertiary treatment of Berlin WWTP effluents with ferrate (Fe(VI)).

    Science.gov (United States)

    Hübner, U; Jekel, M

    2013-01-01

    New and higher standards in the EU water framework directive necessitate advanced treatment of secondary effluents for reduction of trace organic compounds (TrOCs) and nutrients before the discharge into receiving surface waters. Due to its dual function as oxidant and coagulant, ferrate is considered as a promising alternative for tertiary treatment. The oxidation of selected TrOCs and simultaneous flocculation of phosphates by ferrate was tested in batch experiments with secondary effluent from Berlin Ruhleben. The concentrations of carbamazepine (CBZ) and diclofenac were reduced by >90% with ferrate dosages of 6 mg/L as Fe. CBZ was transformed to 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one, which is known as the major product from the reaction of CBZ with ozone. In contrast to ozonation, no further transformation of this product was observed. The concentration of ibuprofen was not reduced by ferrate treatment. For efficient removal of 60-100 μg/L phosphate-P to values <20 μg/L, ferrate dosages of 3-4 mg/L as Fe were sufficient.

  8. Attenuated UV Radiation Alters Volatile Profile in Cabernet Sauvignon Grapes under Field Conditions.

    Science.gov (United States)

    Liu, Di; Gao, Yuan; Li, Xiao-Xi; Li, Zheng; Pan, Qiu-Hong

    2015-09-17

    This study aimed to explore the effect of attenuated UV radiation around grape clusters on the volatile profile of Cabernet Sauvignon grapes (Vitis vinifera L. cv.) under field conditions. Grape bunches were wrapped with two types of polyester films that cut off 89% (film A) and 99% (film B) invisible sunlight of less than 380 nm wavelength, respectively. Solar UV radiation reaching the grape berry surface was largely attenuated, and an increase in the concentrations of amino acid-derived benzenoid volatiles and fatty acid-derived esters was observed in the ripening grapes. Meanwhile, the attenuated UV radiation significantly reduced the concentrations of fatty acid-derived aldehydes and alcohols and isoprenoid-derived norisoprenoids. No significant impact was observed for terpenes. In most case, these positive or negative effects were stage-dependent. Reducing UV radiation from the onset of veraison to grape harvest, compared to the other stages, caused a larger alteration in the grape volatile profile. Partial Least Square Discriminant Analysis (PLS-DA) revealed that (E)-2-hexenal, 4-methyl benzaldehyde, 2-butoxyethyl acetate, (E)-2-heptenal, styrene, α-phenylethanol, and (Z)-3-hexen-1-ol acetate were affected most significantly by the attenuated UV radiation.

  9. Attenuated UV Radiation Alters Volatile Profile in Cabernet Sauvignon Grapes under Field Conditions

    Directory of Open Access Journals (Sweden)

    Di Liu

    2015-09-01

    Full Text Available This study aimed to explore the effect of attenuated UV radiation around grape clusters on the volatile profile of Cabernet Sauvignon grapes (Vitis vinifera L. cv. under field conditions. Grape bunches were wrapped with two types of polyester films that cut off 89% (film A and 99% (film B invisible sunlight of less than 380 nm wavelength, respectively. Solar UV radiation reaching the grape berry surface was largely attenuated, and an increase in the concentrations of amino acid-derived benzenoid volatiles and fatty acid-derived esters was observed in the ripening grapes. Meanwhile, the attenuated UV radiation significantly reduced the concentrations of fatty acid-derived aldehydes and alcohols and isoprenoid-derived norisoprenoids. No significant impact was observed for terpenes. In most case, these positive or negative effects were stage-dependent. Reducing UV radiation from the onset of veraison to grape harvest, compared to the other stages, caused a larger alteration in the grape volatile profile. Partial Least Square Discriminant Analysis (PLS-DA revealed that (E-2-hexenal, 4-methyl benzaldehyde, 2-butoxyethyl acetate, (E-2-heptenal, styrene, α-phenylethanol, and (Z-3-hexen-1-ol acetate were affected most significantly by the attenuated UV radiation.

  10. Evaluation of Volatile Organic Compounds and Carbonyl Compounds Present in the Cabins of Newly Produced, Medium- and Large-Size Coaches in China

    Directory of Open Access Journals (Sweden)

    Yan-Yang Lu

    2016-06-01

    Full Text Available An air-conditioned coach is an important form of transportation in modern motorized society; as a result, there is an increasing concern of in-vehicle air pollution. In this study, we aimed to identify and quantify the levels of volatile organic compounds (VOCs and carbonyl compounds (CCs in air samples collected from the cabins of newly produced, medium- and large-size coaches. Among the identified VOCs and CCs, toluene, ethylbenzene, xylene, formaldehyde, acetaldehyde, acrolein/acetone, and isovaleraldehyde were relatively abundant in the cabins. Time was found to affect the emissions of the contaminants in the coaches. Except for benzaldehyde, valeraldehyde and benzene, the highest in-vehicle concentrations of VOCs and CCs were observed on the 15th day after coming off the assembly line, and the concentrations exhibited an approximately inverted U-shaped pattern as a function of time. Interestingly, this study also showed that the interior temperature of the coaches significantly affected the VOCs emissions from the interior materials, whereas the levels of CCs were mainly influenced by the relative humidity within the coaches. In China, guidelines and regulations for the in-vehicle air quality assessment of the coaches have not yet been issued. The results of this study provide further understanding of the in-vehicle air quality of air-conditioned coaches and can be used in the development of both specific and general rules regarding medium- and large-size coaches.

  11. Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein.

    Science.gov (United States)

    Dai, Tao; Li, Changzhi; Zhang, Bo; Guo, Haiwei; Pan, Xiaoli; Li, Lin; Wang, Aiqin; Zhang, Tao

    2016-12-20

    Toluene is a basic chemical that is currently produced from petroleum resources. In this paper, we report a new route for the effective synthesis of toluene from isoprene and acrolein, two reactants readily available from biomass, through a simple two-step reaction. The process includes Diels-Alder cycloaddition of isoprene and acrolein in a Zn-containing ionic liquid at room temperature to produce methylcyclohex-3-enecarbaldehydes (MCHCAs) as intermediates, followed by M (M=Pt, Pd, Rh)/Al 2 O 3 -catalyzed consecutive dehydrogenation-decarbonylation of the MCHCAs at 573 K to generate toluene with an overall yield up to 90.7 %. Model reactions indicated that a synergistic inductive effect of the C=C double bond and the aldehyde group in MCHCA plays a key role in initiating the consecutive dehydrogenation-decarbonylation, and that methyl benzaldehydes are the key intermediates in the gas-phase transformation of MCHCAs. Microcalorimetric adsorption of CO on different catalysts showed that decarbonylation of the substrate occurs more likely on the strong adsorption sites. To the best of our knowledge, it is the first report of Pt/Al 2 O 3 -catalyzed consecutive dehydrogenation-decarbonylation of a given compound in one reactor. This work provides a highly efficient and environmental friendly route to toluene by utilizing two compounds that can be prepared from biomass. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Emissions of carbonyl compounds from various cookstoves in China

    International Nuclear Information System (INIS)

    Zhang, J.; Smith, K.R.; Univ. of California, Berkeley, CA

    1999-01-01

    This paper presents a new database of carbonyl emission factors for commonly used cookstoves in China. The emission factors, reported both on a fuel-mass basis (mg/kg) and on a defined cooking-task basis (mg/task), were determined using a carbon balance approach for 22 types of fuel/stove combinations. These include various stoves using different species of crop residues and wood, kerosene, and several types of coals and gases. The results show that all the tested cookstoves produced formaldehyde and acetaldehyde and that the vast majority of the biomass stoves produced additional carbonyl compounds such as acetone, acrolein, propionaldehyde, crotonaldehyde, 2-butanone, isobutyraldehyde, butyraldehyde, isovaleraldehyde, valeraldehyde, hexaldehyde, benzaldehyde, o-tolualdehyde, m,p-tolualdehyde, and 2,4-dimethylbenzaldehyde. Carbonyls other than formaldehyde and acetaldehyde, however, were rarely generated by burning coal, coal gas, and natural gas. Kerosene and LPG stoves generated more carbonyl compounds than coal, coal gas, and natural gas stoves, but less than biomass stoves. Indoor levels of carbonyl compounds for typical village houses during cooking hours, estimated using a mass balance model and the measured emission factors, can be high enough to cause acute health effects documented for formaldehyde exposure, depending upon house parameters and individuals' susceptibility

  13. Effects of olfactory function, age, and gender on trigeminally mediated sensations: a study based on the lateralization of chemosensory stimuli.

    Science.gov (United States)

    Hummel, Thomas; Futschik, Thomas; Frasnelli, Johannes; Hüttenbrink, Karl-Bernd

    2003-04-11

    The present investigation aimed to compare trigeminal nasal function of anosmic and hyposmic patients to healthy controls. Further, we aimed to study effects of age and gender on trigeminally mediated sensations following intranasal chemosensory stimulation. Participants were 35 patients with olfactory dysfunction (n=13: functional anosmia; n=22: hyposmia; age 28-69 years, mean age 56 years). Their results were compared with 17 normosmic subjects (28-82 years, mean 52 years). To analyze effects of age and gender in healthy subjects, an additional 24 healthy subjects were included (19-27 years; mean 24 years). Olfactory function was assessed using the 'Sniffin' Sticks' test kit (butanol odor threshold, odor discrimination, odor identification). The subjects' ability to lateralize odors was investigated for benzaldehyde and eucalyptol. Patients with olfactory dysfunction had lower scores in the lateralization task than controls (Pcauses of olfactory dysfunction (P>0.29). There was a weak, but significant, correlation between localization of eucalyptol and duration of olfactory dysfunction (P=0.017). When investigating normosmic subjects only, no gender-related difference was apparent for lateralization scores. However, older subjects had lower scores than younger ones (Pcause of olfactory loss. The deficit appears to improve with duration of the olfactory dysfunction, possibly indicating adaptive mechanisms. Further, the data suggest an age-related decrease of intranasal trigeminal sensitivity in healthy subjects. Analyses additionally indicate a correlation between olfactory and trigeminal sensitivity.

  14. Ceria doped mixed metal oxide nanoparticles as oxidation catalysts: Synthesis and their characterization

    Directory of Open Access Journals (Sweden)

    S.S.P. Sultana

    2015-11-01

    Full Text Available Mixed metal nanoparticles (NPs have attracted significant attention as catalysts for various organic transformations. In this study, we have demonstrated the preparation of nickel–manganese mixed metal oxide NPs doped with X% nano cerium oxide (X = 1, 3, 5 mol% by a facile co-precipitation technique using surfactant and surfactant free methodologies. The as-synthesized materials were calcined at different temperatures (300 °C, 400 °C, and 500 °C, and were characterized using various spectroscopic techniques, including, FTIR and XRD. SEM analysis, TEM analysis and TGA were employed to evaluate the structural properties of the as-prepared catalyst. These were evaluated for their catalytic behaviour towards the conversion of benzyl alcohol to benzaldehyde, which was used as a model reaction with molecular oxygen as oxidant. Furthermore, the effect of the variation of the percentage of nano ceria doping and the calcination temperature on the performance of as-prepared mixed metal catalysts was also evaluated. The kinetic studies of the reactions performed employing gas chromatographic technique have revealed that the mixed metal oxide catalyst doped with 5% nano ceria displayed excellent catalytc activity, among various catalysts synthesized.

  15. Synthesis, characterization and biological activities of novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units

    Directory of Open Access Journals (Sweden)

    Mustafa Ceylan

    2013-09-01

    Full Text Available Novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units were synthesized starting from 1,3-cyclohexadine (4 and maleic anhydride (5. Addition of maleic anhydride (5 to 1,3-cyclehexadine (4 gave an endo-adduct, 3a,4,7,7a-tetrahydro-4,7-ethano-2-benzofuran-1,3-dione (6, in 90% yield. Heating the solution of the adduct dione (6 and 1-(4-aminophenylethanone (7 in the presence of Et 3N in toluene at 110 oC for 24 hours afforded 2-(4-acetylphenyl-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3-dione (8 in high yield. Piperidine-catalyzed addition of benzaldehyde derivatives (9a-i to the compound 8 in CH 2Cl 2 at 55 oC gave the expected chalcone derivatives (10-i in the range of 42% - 96% yields. The antibacterial activities of the chalcone derivatives (10a-i were evaluated against human pathogenic microorganism and the compounds showed low activity compared to the standard, name of the standard.

  16. Alkyne substituted mononuclear photocatalysts based on [RuCl(bpy)(tpy)]⁺.

    Science.gov (United States)

    Davidson, Ross J; Wilson, Lucy E; Duckworth, Andrew R; Yufit, Dmitry S; Beeby, Andrew; Low, Paul J

    2015-07-07

    The ethynyl-phenylene substituted 2,2':6',2''-terpyridine (tpy) derivatives, 4-(phenyl-ethynyl)-2,2':6',2''-terpyridine (L(1)), 4-(methoxyphenyl-ethynyl)-2,2':6',2''-terpyridine (L(2)), 4-(tolyl-ethynyl)-2,2':6',2''-terpyridine (L(3)) and 4-(nitrophenyl-ethynyl)-2,2':6',2''-terpyridine (L(4)) have been used to synthesize four new [RuCl(2,2'-bipyridine)(L(n))]PF6 based complexes. Electronic absorption, resonance Raman, cyclic voltammetry and spectroelectrochemistry aided by DFT calculations were used to explore the influence of the alkynyl substituents on the electronic structures, photochemical and redox properties of the complexes. Furthermore, it is shown that the addition of ethynyl phenyl moieties to the 4-position of the tpy ligand does not have a detrimental effect on these complexes, or the analogous aqua complexes, with respect to their ability to photocatalyse the oxidation of 4-methoxybenzyl alcohol to the corresponding benzaldehyde.

  17. Identification and quantification of organic pollutants in the air of the city of Astana using solid phase microextraction

    Directory of Open Access Journals (Sweden)

    Dina Orazbayeva

    2017-06-01

    Full Text Available Solid-phase microextraction in combination with gas chromatography and mass-spectrometry (GC-MS was used for determination of benzene, toluene, ethylbenzene and o-xylene (BTEX, polycyclic aromatic hydrocarbons (PAH, and for identification of volatile organic compounds (VOCs in ambient air of the city of Astana, Kazakhstan. The screening of the samples showed the presence of mono- and polycyclic aromatic hydrocarbons, alkanes, alkenes, phenols, and benzaldehydes. The concentrations of naphthalene were 5-7 times higher than the permissible value, it was detected in all studied air samples. Average concentration of naphthalene was 18.4 μg/m3, acenaphthylene – 0.54 μg/m3, acenaphthene – 1.63 μg/m3, fluorene – 0.79 μg/m3, anthracene – 3.27 μg/m3, phenanthrene – 0.22 μg/m3, fluorantene – 0.74 μg/m3, pyrene – 0.73 μg/m3. Average concentrations of BTEX in the studied samples were 31.1, 84.9, 10.8 and 11.6 μg/m3, respectively. Based on the statistical analysis of the concentrations of BTEX and PAH, the main source of city air pollution with them was assumed to be vehicle emissions.

  18. Direct synthesis of B-allyl and B-allenyldiisopinocampheylborane reagents using allyl or propargyl halides and indium metal under Barbier-type conditions.

    Science.gov (United States)

    Hirayama, Lacie C; Haddad, Terra D; Oliver, Allen G; Singaram, Bakthan

    2012-05-04

    We report the first one-pot process for the asymmetric addition of allyl, methallyl, and propargyl groups to aldehydes and ketones using B-chlorodiisopinocampheylborane ((d)DIP-Cl) and indium metal. Under Barbier-type conditions, indium metal was used to generate allyl- and allenylindium intermediates, and subsequent reaction with (d)DIP-Cl successfully promoted the transfer of these groups to boron forming the corresponding chiral borane reagents. The newly formed borane reagents were reacted with aldehydes and ketones to produce the corresponding alcohol products in high yields and up to excellent enantioselectivity (98% ee). This method produced excellent enantioenriched secondary homoallylic alcohols from the allylation and methallylation of benzaldehyde. Using this method, the methallylation and cinnamylation of ketones afforded the highest enantioselectivities, while the propargylation of both aldehydes and ketones provided low enantiomeric excesses. In addition, this procedure provided the first synthesis of B-allenyldiisopinocampheylborane, which was characterized by (1)H and (11)B NMR spectroscopy. This is the first example of the direct synthesis of allylboranes that contained substitutions from the corresponding allyl bromide and indium, thereby expanding the utility of the DIP-Cl reagent. Hence, a general and straightforward route to these chiral organoborane reagents in one-pot has been developed along with the asymmetric Barbier-type allylation and propargylation of aldehyde and ketone substrates using these chiral organoborane reagents in subsequent coupling reactions.

  19. Microwave-assisted stereospecific synthesis of novel tetrahydropyran adenine isonucleosides and crystal structures determination

    Science.gov (United States)

    Silva, Fábio P. L.; Cirqueira, Marilia L.; Martins, Felipe T.; Vasconcellos, Mário L. A. A.

    2013-11-01

    We describe in this article stereospecific syntheses for new isonucleosides analogs of adenine 5-7 from tosyl derivatives 2-4 accessing by microwave irradiations (50-80%). The adenine reacts entirely at the N(9) position. Compounds 2-4 were prepared in two steps from the corresponding alcohols 1, 8 and 9 (81-92%). These tetrahydropyrans alcohols 1, 8 and 9 are achiral (Meso compounds) and were prepared in two steps with complete control of 2,4,6-cis relative configuration by Prins cyclization reaction (60-63%) preceded by the Barbier reaction between allyl bromide with benzaldehyde, 4-fluorobenzaldehyde and 2-naphthaldehyde respectively under Lewis acid conditions (96-98%). The configurations and preferential conformations of 5-7 were determined by crystal structure of 6. These novel isonucleosides 5-7 present in silico potentiality to act as GPCR ligand, kinase inhibitor and enzyme inhibitor, evaluated by Molinspiration program, consistent with the expected antiviral and anticancer bioactivities.

  20. Structure and reactivity of an Al/P-based frustrated Lewis pair bearing relatively small substituents at aluminium.

    Science.gov (United States)

    Pleschka, Damian; Layh, Marcus; Rogel, Friedhelm; Uhl, Werner

    2017-08-28

    Reaction of Mes 2 P─C≡C─Ph (Mes = mesityl) with dineopentylaluminium hydride afforded by hydroalumination a geminal Al/P-based frustrated Lewis pair (FLP; 4 ). Its steric shielding is relatively low, and its reactivity in various secondary reactions is less hindered by steric repulsion than observed for related compounds having bulkier groups attached to aluminium. FLP 4 yielded adducts with Me 3 C─NCO or benzaldehyde via the formation of Al-O and P-C bonds. Trimethylsilyl azide reacted with 4 under surprisingly mild conditions to afford a nitrene complex by spontaneous N 2 elimination below room temperature. A carbodiimide molecule was coordinated via one of the C=N bonds to form a five-membered AlCPNC heterocycle with an intact C=N bond in an exocyclic position. A very large molecule was obtained by the reaction of two equivalents of 4 with a bifunctional methylene-bridged phenylene isocyanate precursor.This article is part of the themed issue 'Frustrated Lewis pair chemistry'. © 2017 The Author(s).

  1. Hierarchical Porous Interlocked Polymeric Microcapsules: Sulfonic Acid Functionalization as Acid Catalysts

    Science.gov (United States)

    Wang, Xiaomei; Gu, Jinyan; Tian, Lei; Zhang, Xu

    2017-03-01

    Owing to their unique structural and surface properties, mesoporous microspheres are widely applied in the catalytic field. Generally, increasing the surface area of the specific active phase of the catalyst is a good method, which can achieve a higher catalytic activity through the fabrication of the corresponding catalytic microspheres with the smaller size and hollow structure. However, one of the major challenges in the use of hollow microspheres (microcapsules) as catalysts is their chemical and structural stability. Herein, the grape-like hypercrosslinked polystyrene hierarchical porous interlocked microcapsule (HPIM-HCL-PS) is fabricated by SiO2 colloidal crystals templates, whose structure is the combination of open mouthed structure, mesoporous nanostructure and interlocked architecture. Numerous microcapsules assembling together and forming the roughly grape-like microcapsule aggregates can enhance the structural stability and recyclability of these microcapsules. After undergoing the sulfonation, the sulfonated HPIM-HCL-PS is served as recyclable acid catalyst for condensation reaction between benzaldehyde and ethylene glycol (TOF = 793 h-1), moreover, exhibits superior activity, selectivity and recyclability.

  2. Trichocyanines: a Red-Hair-Inspired Modular Platform for Dye-Based One-Time-Pad Molecular Cryptography.

    Science.gov (United States)

    Leone, Loredana; Pezzella, Alessandro; Crescenzi, Orlando; Napolitano, Alessandra; Barone, Vincenzo; d'Ischia, Marco

    2015-06-01

    Current molecular cryptography (MoCryp) systems are almost exclusively based on DNA chemistry and reports of cryptography technologies based on other less complex chemical systems are lacking. We describe herein, as proof of concept, the prototype of the first asymmetric MoCryp system, based on an 8-compound set of a novel bioinspired class of cyanine-type dyes called trichocyanines. These novel acidichromic cyanine-type dyes inspired by red hair pigments were synthesized and characterized with the aid of density functional theory (DFT) calculations. Trichocyanines consist of a modular scaffold easily accessible via an expedient condensation of 3-phenyl- or 3-methyl-2H-1,4-benzothiazines with N-dimethyl- or o-methoxyhydroxy-substituted benzaldehyde or cinnamaldehyde derivatives. The eight representative members synthesized herein can be classified as belonging to two three-state systems tunable through four different control points. This versatile dye platform can generate an expandable palette of colors and appears to be specifically suited to implement an unprecedented single-use asymmetric molecular cryptography system. With this system, we intend to pioneer the translation of digital public-key cryptography into a chemical-coding one-time-pad-like system.

  3. Surface functional group characterization using chemical derivatization X-ray photoelectron spectroscopy (CD-XPS)

    Energy Technology Data Exchange (ETDEWEB)

    Jagst, Eda

    2011-03-18

    Chemical derivatization - X-ray photolectron spectroscopy (CD-XPS) was applied successfully in order to determine different functional groups on thin film surfaces. Different amino group carrying surfaces, prepared by spin coating, self-assembly and plasma polymerization, were successfully investigated by (XPS) and near edge X-ray absorption fine structure (NEXAFS) spectroscopy. Amino groups were derivatized with the widely used primary amino group tags, pentafluorobenzaldehyde (PFB) and 4-(trifluoromethyl)-benzaldehyde (TFBA), prior to analysis. Primary amino group quantification was then carried out according to the spectroscopical data. Self-assembled monolayers (SAMs) of different terminal groups were prepared and investigated with XPS and spectra were compared with reference surfaces. An angle resolved NEXAFS measurement was applied to determine the orientation of SAMs. Plasma polymerized allylamine samples with different duty cycle, power and pressure values were prepared in order to study the effects of external plasma parameters on the primary amino group retention. CD-XPS was used to quantify the amino groups and experiments show, that the milder plasma conditions promote the retention of amino groups originating from the allylamine monomer. An interlaboratory comparison of OH group determination on plasma surfaces of polypropylene treated with oxygen plasma, was studied. The surfaces were investigated with XPS and the [OH] amount on the surfaces was calculated. (orig.)

  4. Synthesis and Antiplasmodial Activity of 2-(4-Methoxyphenyl-4-Phenyl-1,10-Phenanthroline Derivative Compounds

    Directory of Open Access Journals (Sweden)

    Nazudin

    2012-08-01

    Full Text Available A unique of synthetic methods was employed to prepare 2-(4-methoxyphenyl-4-phenyl-1,10-phenanthroline (5 derivatives from 4-methoxy-benzaldehyde (1, acetophenone (2, and 8-aminoquinoline (4 with aldol condensation and cyclization reactions. The derivatives were tested through antiplasmodial test. The synthesis of derivatives compound 5 was conducted in three steps. The 3-(4-methoxyphenyl-1-phenylpropenone 3 was synthesized through aldol condensation of 1 and 2 which has a yield of 96.42%. The compound 5 was synthesized through cyclization of compound 4 and 3 with 84.55% yield. The derivative of compound 5 was synthesized from compound 5 using DMS and DES reagents which refluxed for 21 and 22 h, to produce (1-N-methyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (6 and (1-N-ethyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (7 with 91.42 and 86.36% yields, respectively. Results of in vitro testing of antiplasmodial activity of compound 5 derivatives (i.e., compound 6 and 7 against chloroquine-resistant P. falciparum FCR3 strain showed that compound 7 had higher antimalarial activity than compounds 5 and 6. Whereas, results of in vitro testing against chloroquine-sensitive P. falciparum D10 strain showed that compound 6 has higher antimalarial activity than compounds 5 and 7.

  5. Determination of starting materials, intermediates, and subsidiary colors in the color additive Food Red No. 106 (Sulforhodamine B) using high-performance liquid chromatography.

    Science.gov (United States)

    Tatebe, Chiye; Ohtsuki, Takashi; Fujita, Tsuyoshi; Nishiyama, Koji; Itoh, Sumio; Sugimoto, Naoki; Kubota, Hiroki; Tada, Atsuko; Sato, Kyoko; Akiyama, Hiroshi

    2017-12-15

    The main subsidiary color of structure in Food Red No. 106 (R106) was identified to be a desethyl derivative (R106-SubA). High-performance liquid chromatography (HPLC) was performed for the quantitative determination of benzaldehyde-2,4-disulfonic acid, N,N-diethyl-m-aminophenol, leuco acid, pyrone acid, R106-SubA, etc. in R106. An ammonium acetate solution (20mM) and acetonitrile:water (7:3) were used to stabilize the retention time of the HPLC analytes. The linearity of the calibration curves was in the range of 0.05-10μg/mL, with good correlation coefficients (R 2 >0.9983). The recoveries of impurities at levels 0.1%, 0.5% and 1% ranged from 94.2% to 106.6% with relative standard deviations of 0.1%-1.0%. While surveying commercial R106, the amounts obtained by area% determination were similar to those obtained by the calibration-curve determination. The area% determination by HPLC for the determinations of impurities in R106 is a simple and reliable method and can be applied in routine analysis. Copyright © 2017 Elsevier Ltd. All rights reserved.

  6. The first-principle study on the stability of trans-HCOH in various solvents

    Science.gov (United States)

    Nur Fadilla, Rizka; Dwi Aisyah, Nufida; Dipojono, Hermawan K.; Rusydi, Febdian

    2017-05-01

    We attempt to study about the solvent effects of the stability of trans-HCOH molecules using the density-functional theory. Experimentally, trans-HCOH rearranges to H2CO with half-life of two hours [1] which we theoretically proved that it occurs through quantum tunneling. [2] In this work, we calculate the rearrangement rate of the molecules in various solvents. The solvents are selected based on their dielectric constant values, from lower to higher ones; they are benzene, dichloroethane, benzaldehyde, acetone, methanol, ethanediol, dimethylsulfoxide, formic acid, water, and formamide. We use polarizable continuum to model the solvents (PCM). We begin from determining the reaction path from trans-HCOH to H2CO and its corresponding energy barrier using intrinsic reaction coordinate calculation with PCM. Then, we use Wentzel-Kramers-Brillouin (WKB) approximation to calculate the rearrangement rates. The calculation results showed a general trend in which there were arrangement rate was decreasing inversely proportional to dielectric constant value.

  7. Anaerobic degradation of alkylated benzenes in denitrifying laboratory aquifer columns

    International Nuclear Information System (INIS)

    Kuhn, E.P.; Zeyer, J.; Eicher, P.; Schwarzenbach, R.P.

    1988-01-01

    Toluene and m-xylene were rapidly mineralized in an anaerobic laboratory aquifer column operated under continuous-flow conditions with nitrate as an electron acceptor. The oxidation of toluene and m-xylene was coupled with the reduction of nitrate, and mineralization was confirmed by trapping 14 CO 2 evolved from 14 C-ring-labeled substrates. Substrate degradation also took place when nitrous oxide replaced nitrate as an electron acceptor, but decomposition was inhibited in the presence of molecular oxygen or after the substitution of nitrate by nitrite. The m-xylene-adapted microorganisms in the aquifer column degraded toluene, benzaldehyde, benzoate, m-toluylaldehyde, m-toluate, m-cresol, p-cresol, and p-hydroxybenzoate but were unable to metabolize benzene, naphthalene, methylcyclohexane, and 1,3-dimethylcyclohexane. Isotope-dilution experiments suggested benzoate as an intermediate formed during anaerobic toluene metabolism. The finding that the highly water-soluble nitrous oxide served as electron acceptor for the anaerobic mineralization of some aromatic hydrocarbons may offer attractive options for the in situ restoration of polluted aquifers

  8. Using Distonic Radical Ions to Probe the Chemistry of Key Combustion Intermediates: The Case of the Benzoxyl Radical Anion

    Science.gov (United States)

    Li, Cong; Lam, Adrian K. Y.; Khairallah, George N.; White, Jonathan M.; O'Hair, Richard A. J.; da Silva, Gabriel

    2013-04-01

    The benzoxyl radical is a key intermediate in the combustion of toluene and other aromatic hydrocarbons, yet relatively little experimental work has been performed on this species. Here, a combination of electrospray ionization (ESI), multistage mass spectrometry experiments, and density functional theory (DFT) calculations are used to examine the formation and fragmentation of a benzoxyl (benzyloxyl) distonic radical anion. Excited 4-carboxylatobenzoxyl radical anions were produced via two methods: (1) collision induced dissociation (CID) of the nitrate ester 4-(nitrooxymethyl)benzoate, -O2CC6H4CH2ONO2, and (2) reaction of ozone with the 4-carboxylatobenzyl radical anion, -O2CC6H4CH2 •. In neither case was the stabilized -O2CC6H4CH2O• radical anion intermediate detected. Instead, dissociation products at m/ z 121 and 149 were observed. These products are attributed to benzaldehyde (O2 -CC6H4CHO) and benzene (-O2CC6H5) products from respective loss of H and HCO radicals in the vibrationally excited benzoxyl intermediate. In no experiments was a product at m/ z 120 (i.e., -O2CC6H4 •) detected, corresponding to absence of the commonly assumed phenyl radical + CH2=O channel. The results reported suggest that distonic ions are useful surrogates for reactive intermediates formed in combustion chemistry.

  9. Double Intramolecular Transacetalization of Polyhydroxy Acetals: Synthesis of Conformationally-Restricted 1,3-Dioxanes with Axially-Oriented Phenyl Moiety

    Directory of Open Access Journals (Sweden)

    Samuel Asare-Nkansah

    2016-11-01

    Full Text Available 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 deprotection, the second intramolecular transacetalization afforded tricyclic alcohol 14a (2-(1,5-epoxy-1,3,4,5-tetrahydro-2-benzoxepin-3-yl]ethan-1-ol. Analogous cyclizations led to the corresponding silyl ether 22a (19% and azide 23a (13%. Whereas tricyclic alcohol 14a was obtained as a 1:1 mixture of diastereomers, the silyl ether 22a and the azide 23a afforded only one diastereomer. This observation indicates a faster cyclization of the minor diastereomers providing the thermodynamically-favored compounds with equatorially-oriented substituents in the 3-position of the tricyclic 1,5-epoxy-2-benzoxepine system. In general, acetophenone-derived ketalic compounds (b-series required very mild reaction conditions and gave lower yields than the corresponding acetalic compounds (a-series.

  10. Kinetic Studies on the Selective Oxidation of Benzyl Alcohols in Organic Medium under Phase Transfer Catalysis

    Directory of Open Access Journals (Sweden)

    K. Bijudas

    2014-07-01

    Full Text Available Kinetic studies on the oxidation of benzyl alcohol and substituted benzyl alcohols in benzene as the reaction medium have been studied by using potassium dichromate under phase transfer catalysis (PTC. The phase transfer catalysts (PT catalysts used were tetrabutylammonium bromide (TBAB and tetrabutylphosphonium bromide (TBPB.  Benzyl alcohols were selectively oxidised to corresponding benzaldehydes in good yield (above 90%.  The order of reactivity among the studied benzyl alcohols is p - OCH3 > p - CH3 > - H > p - Cl.  Plots of log k2 versus Hammett's substituent constant (s has been found to be curve shaped and this suggests that there should be a continuous change in transition state with changes in substituent present in the substrate from electron donating to electron withdrawing. A suitable mechanism has been suggested in which the rate determining step involves both C - H bond cleavage and C - O bond formations in concerted manner. © 2014 BCREC UNDIP. All rights reserved.Received: 16th March 2014; Revised: 18th May 2014; Accepted: 18th May 2014[How to Cite: Bijudas, K., Bashpa, P., Nair, T.D.R. (2014. Kinetic Studies on the Selective Oxidation of Benzyl Alcohol and Substituted Benzyl Alcohols in Organic Medium under Phase Transfer Catalysis. Bulletin of Chemical Reaction Engineering & Catalysis, 9 (2: 142-147. (doi:10.9767/bcrec.9.2.6476.142-147][Permalink/DOI: http://dx.doi.org/10.9767/bcrec.9.2.6476.142-147] 

  11. Volatile organic emissions from the distillation and pyrolysis of vegetation

    Science.gov (United States)

    Greenberg, J. P.; Friedli, H.; Guenther, A. B.; Hanson, D.; Harley, P.; Karl, T.

    2006-01-01

    Leaf and woody plant tissue (Pinus ponderosa, Eucalyptus saligna, Quercus gambelli, Saccharum officinarum and Oriza sativa) were heated from 30 to 300°C and volatile organic compound (VOC) emissions were identified and quantified. Major VOC emissions were mostly oxygenated and included acetic acid, furylaldehyde, acetol, pyrazine, terpenes, 2,3-butadione, phenol and methanol, as well as smaller emissions of furan, acetone, acetaldehyde, acetonitrile and benzaldehyde. Total VOC emissions from distillation and pyrolysis were on the order of 10 gC/kgC dry weight of vegetation, as much as 33% and 44% of CO2 emissions (gC(VOC)/gC(CO2)) measured during the same experiments, in air and nitrogen atmospheres, respectively. The emissions are similar in identity and quantity to those from smoldering combustion of woody tissue and of different character than those evolved during flaming combustion. VOC emissions from the distillation of pools and endothermic pyrolysis under low turbulence conditions may produce flammable concentrations near leaves and may facilitate the propagation of wildfires. VOC emissions from charcoal production are also related to distillation and pyrolysis; the emissions of the highly reactive VOCs from production are as large as the carbon monoxide emissions.

  12. Desalination of fish sauce by electrodialysis: effect on selected aroma compounds and amino acid compositions.

    Science.gov (United States)

    Chindapan, Nathamol; Devahastin, Sakamon; Chiewchan, Naphaporn; Sablani, Shyam S

    2011-09-01

    Fish sauce is an ingredient that exhibits unique flavor and is widely used by people in Southeast Asia. Fish sauce, however, contains a significant amount of salt (sodium chloride). Recently, electrodialysis (ED) has been successfully applied to reduce salt in fish sauce; however, no information is available on the effect of ED on changes in compounds providing aroma and taste of ED-treated fish sauce. The selected aroma compounds, amino acids, and sensory quality of the ED-treated fish sauce with various salt concentrations were then analyzed. The amounts of trimethylamine, 2,6-dimethylpyrazine, phenols, and all carboxylic acids except for hexanoic acid significantly decreased, whereas benzaldehyde increased significantly when the salt removal level was higher. The amounts of all amino acids decreased with the increased salt removal level. Significant difference in flavor and saltiness intensity among ED-treated fish sauce with various salt concentrations, as assessed by a discriminative test, were observed. Information obtained in this work can serve as a guideline for optimization of a process to produce low-sodium fish sauce by ED. It also forms a basis for further in-depth sensory analysis of low-sodium fish sauce. © 2011 Institute of Food Technologists®

  13. Use of Tetragenococcus halophilus as a starter culture for flavor improvement in fish sauce fermentation.

    Science.gov (United States)

    Udomsil, Natteewan; Rodtong, Sureelak; Choi, Yeung Joon; Hua, Yanglin; Yongsawatdigul, Jirawat

    2011-08-10

    The potential of Tetragenococcus halophilus as a starter culture for flavor improvement in fish sauce fermentation was elucidated. Four strains of T. halophilus isolated from fish sauce mashes were inoculated to anchovy mixed with 25% NaCl with an approximate cell count of 10(6) CFU/mL. The α-amino content of 6-month-old fish sauce samples inoculated with T. halophilus was 780-784 mM. The addition of T. halophilus MRC10-1-3 and T. halophilus MCD10-5-10 resulted in a reduction of histamine (P Fish sauce inoculated with T. halophilus showed high contents of total amino acids with predominantly high glutamic acid. Major volatile compounds in fish sauce were 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, and benzaldehyde. T. halophilus-inoculated fish sauce samples demonstrated the ability to reduce dimethyl disulfide, a compound contributing to a fecal note. The use of T. halophilus for fish sauce fermentation improves amino acid profiles and volatile compounds as well as reduces biogenic amine content of a fish sauce product.

  14. Contribution of aldehyde oxidase, xanthine oxidase, and aldehyde dehydrogenase on the oxidation of aromatic aldehydes.

    Science.gov (United States)

    Panoutsopoulos, Georgios I; Kouretas, Demetrios; Beedham, Christine

    2004-10-01

    Aliphatic aldehydes have a high affinity toward aldehyde dehydrogenase activity but are relatively poor substrates of aldehyde oxidase and xanthine oxidase. In addition, the oxidation of xenobiotic-derived aromatic aldehydes by the latter enzymes has not been studied to any great extent. The present investigation compares the relative contribution of aldehyde dehydrogenase, aldehyde oxidase, and xanthine oxidase activities in the oxidation of substituted benzaldehydes in separate preparations. The incubation of vanillin, isovanillin, and protocatechuic aldehyde with either guinea pig liver aldehyde oxidase, bovine milk xanthine oxidase, or guinea pig liver aldehyde dehydrogenase demonstrated that the three aldehyde oxidizing enzymes had a complementary substrate specificity. Incubations were also performed with specific inhibitors of each enzyme (isovanillin for aldehyde oxidase, allopurinol for xanthine oxidase, and disulfiram for aldehyde dehydrogenase) to determine the relative contribution of each enzyme in the oxidation of these aldehydes. Under these conditions, vanillin was rapidly oxidized by aldehyde oxidase, isovanillin was predominantly metabolized by aldehyde dehydrogenase activity, and protocatechuic aldehyde was slowly oxidized, possibly by all three enzymes. Thus, aldehyde oxidase activity may be a significant factor in the oxidation of aromatic aldehydes generated from amines and alkyl benzenes during drug metabolism. In addition, this enzyme may also have a role in the catabolism of biogenic amines such as dopamine and noradrenaline where 3-methoxyphenylacetic acids are major metabolites.

  15. Fluorescent sensors based on BODIPY derivatives for aluminium ion recognition: an experimental and theoretical study.

    Science.gov (United States)

    Keawwangchai, Tasawan; Morakot, Nongnit; Wanno, Banchob

    2013-03-01

    Two BODIPY derivative sensors for metal ion recognition containing 10-(4-hydroxyphenyl) (L1) and 10-(3,4-dihydroxyphenyl) (L2) were synthesized in a one-pot reaction of benzaldehyde derivative and 2,4-dimethylpyrrole in the presence of trifluoroacetic acid as catalyst. The binding abilities between these sensors and 50 equivalents of Na(+), K(+), Ag(+), Ca(2+), Fe(2+), Co(2+), Ni(2+), Cu(2+), Zn(2+), Cd(2+), Pb(2+), Al(3+) and Cr(3+) ions were studied using UV-vis and fluorescent spectroscopic methods. Of all the metal ions tested, Al(3+) ion showed the greatest decrease in intensity in the spectra of the sensors, and therefore Al(3+) ion forms the strongest complex. The binding abilities of BODIPY receptors with Na(+), Ag(+), Ca(2+), Co(2+), Ni(2+), Cu(2+), Zn(2+) and Al(3+) ions were also investigated using density functional theory (DFT) calculations at B3LYP/LanL2DZ theoretical level. The calculated results point to the same conclusion. DFT calculations also provided the HOMO-LUMO energy levels, which can explain the spectrum change upon complexation.

  16. Volatile organic emissions from the distillation and pyrolysis of vegetation

    Directory of Open Access Journals (Sweden)

    J. P. Greenberg

    2006-01-01

    Full Text Available Leaf and woody plant tissue (Pinus ponderosa, Eucalyptus saligna, Quercus gambelli, Saccharum officinarum and Oriza sativa were heated from 30 to 300°C and volatile organic compound (VOC emissions were identified and quantified. Major VOC emissions were mostly oxygenated and included acetic acid, furylaldehyde, acetol, pyrazine, terpenes, 2,3-butadione, phenol and methanol, as well as smaller emissions of furan, acetone, acetaldehyde, acetonitrile and benzaldehyde. Total VOC emissions from distillation and pyrolysis were on the order of 10 gC/kgC dry weight of vegetation, as much as 33% and 44% of CO2 emissions (gC(VOC/gC(CO2 measured during the same experiments, in air and nitrogen atmospheres, respectively. The emissions are similar in identity and quantity to those from smoldering combustion of woody tissue and of different character than those evolved during flaming combustion. VOC emissions from the distillation of pools and endothermic pyrolysis under low turbulence conditions may produce flammable concentrations near leaves and may facilitate the propagation of wildfires. VOC emissions from charcoal production are also related to distillation and pyrolysis; the emissions of the highly reactive VOCs from production are as large as the carbon monoxide emissions.

  17. Synthesis and Spectroscopic Characterization of Some New Biological Active Azo–Pyrazoline Derivatives

    Directory of Open Access Journals (Sweden)

    Farouq E. Hawaiz

    2012-01-01

    Full Text Available A number of 3-[4-(benzyloxy-3-(2-Chlorophenylazo-phenyl]-5-(substituted-phenyl-1-substituted-2-pyrazolines( 4a-j and (5a-j have been synthesized by diazotization of 2-chloroaniline and its coupling reaction with 4-hydroxy acetophenone, followed by benzyloxation of the hydroxyl group to give the substrate [4-benzyloxy-3-(2-chlorophenylazo-acetophenone (1].The prepared starting material (1 has been reacted with different substituted benzaldehydes to give a new series of chalcone derivatives 1-[(4-benzyloxy-3-(2-chloro-phenylazo-phenyl]-3-(substituted phenyl-2-propen-1-one (3a-j, in high yields and in a few minutes, and the later compounds were treated with hydrazine hydrate according to Michael addition reaction to afford a new biolological active target compounds (4a-j and (5a-j. Furthermore, The structures of the newly synthesized compounds were confirmed by FT-IR, 13C-NMR,13C-DEPT & 1H-NMR spectral data. The chalcone and pyrazoline derivatives were evaluated for their anti bacterial activity against Escherichia coli as gram negative and Staphylococcus aureus as gram positive, the results showed significant activity against both types of bacteria.

  18. Synthesis of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives and evaluation of their anticancer activity

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    Nitin Kumar

    2017-05-01

    Full Text Available A novel series of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives were synthesized. In the first step salicylaldehyde was reacted with ethylacetoacetate at room temperature by stirring which gives compound (I. Compound (I when refluxed with substituted benzaldehyde and diethylamine in the presence of n-butanol for 4–5 h gives substituted derivatives (IIa–d. Compounds synthesized in step 2 when refluxed with phenyl hydrazine in the presence of pyridine for 6–7 h gives the title compounds (IIIa–d. All the synthesized compounds were sent to NCI for anticancer activity. Synthesized compounds were tested for anticancer activity against 60 different cell lines. From the data thus obtained it was observed that simple coumarin ring derivatives were more effective in inhibiting the growth of cancerous cell lines, than coumarin-pyrazoline derivatives. Among all the synthesized compounds, irrespective of compounds having simple coumarin ring and coumarin-pyrazoline combination, compounds IIa–c, IIIb and IIId were potent anticancer agents. Compounds were active for the single dose therapeutic program at the dose of 1.00E-5 molar concentration. The main anti cancer activity is assumed to be due to the presence of the lactone structure in coumarin moiety.

  19. Generalization and discrimination tasks yield concordant measures of perceived distance between odours and their binary mixtures in larval Drosophila.

    Science.gov (United States)

    Chen, Yi-chun; Gerber, Bertram

    2014-06-15

    Similarity between odours is notoriously difficult to measure. Widely used behavioural approaches in insect olfaction research are cross-adaptation, masking, as well as associative tasks based on olfactory learning and the subsequent testing for how specific the established memory is. A concern with such memory-based approaches is that the learning process required to establish an odour memory may alter the way the odour is processed, such that measures of perception taken at the test are distorted. The present study was therefore designed to see whether behavioural judgements of perceptual distance are different for two different memory-based tasks, namely generalization and discrimination. We used odour-reward learning in larval Drosophila as a study case. In order to challenge the larvae's olfactory system, we chose to work with binary mixtures and their elements (1-octanol, n-amyl acetate, 3-octanol, benzaldehyde and hexyl acetate). We determined the perceptual distance between each mixture and its elements, first in a generalization task, and then in a discrimination task. It turns out that scores of perceptual distance are correlated between both tasks. A re-analysis of published studies looking at element-to-element perceptual distances in larval reward learning and in adult punishment learning confirms this result. We therefore suggest that across a given set of olfactory stimuli, associative training does not grossly alter the pattern of perceptual distances. © 2014. Published by The Company of Biologists Ltd.

  20. Volatile Chemicals of Adults and Nymphs of the Eucalyptus Pest, Thaumastocoris peregrinus (Heteroptera: Thaumastocoridae

    Directory of Open Access Journals (Sweden)

    Camila B. C. Martins

    2012-01-01

    Full Text Available Thaumastocoris peregrinus is an introduced “true bug” that is now a severe pest in Eucalyptus plantations of various Southern Hemisphere countries. The semiochemicals of thaumastocorids are completely unknown. Therefore, volatile chemicals from T. peregrinus nymphs and adults were identified as possible leads for pheromones potentially useful for control. The contents of nymphal exocrine glands, which are shed at molting, were identified from extracts of exuviae. Adults lack functional metathoracic scent glands that are characteristic of most heteropterans; however, both males and females possess a glandular-appearing hold-fast organ that they quickly extrude posteriorly when disturbed. Whole body hexane extracts from males and females were prepared by freezing the insects in a flask so that they extruded the hold-fast organ, and then they were extracted with hexane. Volatiles from nymphal exuviae included benzaldehyde, octanol, (E-2-octenol, octanoic acid, decanal, and hexanoic acid. Adult volatiles included 3-methylbut-2-en-1-yl butyrate and 3-methylbut-3-en-1-yl butyrate.

  1. Influence of harvest date on volatile and sensory profile of vine leaves infusions from two Portuguese red grape varieties

    Directory of Open Access Journals (Sweden)

    Jordão António M.

    2017-01-01

    Full Text Available The main object of the present study was to investigate the volatile composition and sensorial profile of vine leaves infusions prepared from vine leaves collected 30 and 60 days after grape harvest from two Portuguese red grape varieties (Touriga Nacional and Tinta Roriz. Twelve volatile compounds were detected in vine leaves infusions (6-methyl-5-hepten-2-one, 1-undecene, Z-citral, cedrenol, DL-limonene, 2,4-hexadien-2-ol, benzaldehyde, heptane-1,2,4,6-tetraene, cyclohexene 1-methyl-4-(1-methylethyl, 1,6-octadien-3-ol, 3,7-dimethyl, 5,9-undecadien-2-one-6,10-dimethyl-(5E and α-cedrol. In addition, it was observed that the volatile compounds present in vine leaves infusions were dependent on the harvest time, with significantly major volatile content in vine leaves collected after 30 days of harvesting. Thus, it was more important the harvesting date for the volatile profile of vine leaves infusion than the vine leave grape cultivar. Similar tendency was also obtained for the sensory profile, with significant differences for astringency and aroma intensity attributes of vine leaves infusions according to the harvesting date.

  2. Characterization of Botanical and Geographical Origin of Corsican “Spring” Honeys by Melissopalynological and Volatile Analysis

    Directory of Open Access Journals (Sweden)

    Yin Yang

    2014-01-01

    Full Text Available Pollen spectrum, physicochemical parameters and volatile fraction of Corsican “spring” honeys were investigated with the aim of developing a multidisciplinary method for the qualification of honeys in which nectar resources are under-represented in the pollen spectrum. Forty-one Corsican “spring” honeys were certified by melissopalynological analysis using directory and biogeographical origin of 50 representative taxa. Two groups of honeys were distinguished according to the botanical origin of samples: “clementine” honeys characterized by the association of cultivated species from oriental plain and other “spring” honeys dominated by wild herbaceous taxa from the ruderal and/or maquis area. The main compounds of the “spring” honey volatile fraction were phenylacetaldehyde, benzaldehyde and methyl-benzene. The volatile composition of “clementine” honeys was also characterized by three lilac aldehyde isomers. Statistical analysis of melissopalynological, physicochemical and volatile data showed that the presence of Citrus pollen in “clementine” honeys was positively correlated with the amount of linalool derivatives and methyl anthranilate. Otherwise, the other “spring” honeys were characterized by complex nectariferous species associations and the content of phenylacetaldehyde and methyl syringate.

  3. New Approach to Evaluate the Antennal Response of an Adult Predator Insect to Different Volatile Chemical Compounds by using Electroantennogram Technique

    Science.gov (United States)

    Shonouda, Mourad L.

    The antennal response of adult syrphid flies to selected plant volatile chemical compounds was investigated in the present study. The main chemical classes and their chemical compounds were aldehydes (nonanal and benzaldehyde), monoterpene-alcohols (linalool and alpha-terpineol), ketones (6-methyl-5-heptene-2-one and 2-undecanone), hydrocarbons (tetradecane) and benzoids (methyl salicylate). Electroantennogram (EAG) records showed that the syrphid antennae were strongly responded to linalool, 6-methyl-5-heptene-2-one and methyl salicylate even at low concentrations, in addition to the high dose concentration of nonanal comparably to the other chemical compounds. The antennae of old syrphid adults were more responsive and elicited higher levels of responses to all compounds rather than young syrphid adults. The antennal sensitivity may differ from one compound to another according to the sex. The difference in responses could be attributed to the sensitivity of olfactory receptors and/or the characterization of binding protein(s). The quality of biocontrol agent could be improved if the chemical interaction between beneficial natural enemies and the surrounding environment is intensively studied and we clearly understand the chemical ecology of each natural enemy.

  4. Synthesis and characterization of Cr-MSU-1 and its catalytic application for oxidation of styrene

    Science.gov (United States)

    Liu, Hong; Wang, Zhigang; Hu, Hongjiu; Liang, Yuguang; Wang, Mengyang

    2009-07-01

    Chromium-containing mesoporous silica material Cr-MSU-1 was synthesized using lauryl alcohol-polyoxyethylene (23) ether as templating agent under the neutral pH condition by two-step method. The sample was characterized by XRD, TEM, FT-IR, UV-Vis, ESR, ICP-AES and N 2 adsorption. Its catalytic performance for oxidation of styrene was studied. Effects of the solvent used, the styrene/H 2O 2 mole ratio and the reaction temperature and time on the oxidation of styrene over the Cr-MSU-1 catalyst were examined. The results indicate that Cr ions have been successfully incorporated into the framework of MSU-1 and the Cr-MSU-1 material has a uniform worm-like holes mesoporous structure. After Cr-MSU-1 is calcined, most of Cr 3+ is oxidized to Cr 5+ and Cr 6+ in tetrahedral coordination and no extra-framework Cr 2O 3 is formed. The Cr-MSU-1 catalyst is highly active for the selective oxidation of styrene and the main reaction products over Cr-MSU-1 are benzaldehyde and phenylacetaldehyde. Its catalytic performance remains stable within five repeated runs and no leaching is noticed for this chromium-based catalyst.

  5. Effect of resin content and substrate on the emission of BTEX and carbonyls from low-VOC water-based wall paint.

    Science.gov (United States)

    Zhao, Ping; Cheng, Yu-Hsiang; Lin, Chi-Chi; Cheng, Yu-Lin

    2016-02-01

    The primary aim of this work is to explore the effect of resin content and the effect of substrate on the emission of benzene, toluene, ethylbenzene, and xylene (BTEX) and carbonyls from low-VOC water-based wall paint. Four low-volatile organic compound (VOC) paints include paints A (20% acrylic), B (30% acrylic), C (20% polyvinyl acetate), and D (30% polyvinyl acetate) were painted on stainless steel specimen for the study of resin effect. Green calcium silicate, green cement, and stainless steel were painted with paints A and C for the study of substrate effect. Concentrations of the VOCs in the chamber decreased with the elapsed time. Both resin type and resin quantity in paint had effects on VOC emissions. Paints with acrylic resin emitted less BTEX and carbonyls than paints with polyvinyl acetate resin. However, the effects of resin quantity varied with VOCs. Porous substrates were observed to interact more strongly with paints than inert substrates. Both green calcium silicate and green cement substrates have strong power of adsorption of VOCs from wall paints, namely toluene, formaldehyde, acetaldehyde, 2-butanone, methacrolein, butyraldehyde, and benzaldehyde. Some compounds like toluene, formaldehyde, and butyaldehyde were desorbed very slowly from green calcium silicate and green cement substrates.

  6. Impedance spectroscopy analysis of human odorant binding proteins immobilized on nanopore arrays for biochemical detection.

    Science.gov (United States)

    Lu, Yanli; Zhang, Diming; Zhang, Qian; Huang, Yixuan; Luo, Senbiao; Yao, Yao; Li, Shuang; Liu, Qingjun

    2016-05-15

    Human odorant-binding proteins (hOBPs) not only can bind and transport odorants in the surrounding environment for sensing smells, but also play important roles in transmitting lots of biomolecules in different organs. Utilizing the properties of hOBPs, an electrochemical biosensor with nanopore array was developed to detect specific biomolecular ligands, such as aldehydes and fatty acids. The highly ordered nanopores of anodic aluminum oxide with diameter of 20-40 nm were fabricated with two-step oxidation. Through 2-carboxyethyl phosphonic acid, hOBPs were self-assembled on nanopores as the sensing membrane. With nanopore arrays, the impedance spectra showed quite different electron transfer processes in the frequency spectra, which could be characterized by the electron transfer resistance and electrical resistance of the porous membrane. Under stimulation of biomolecular ligands, series resistance of nanopores and hOBPs increased and showed a concentration-dependence feature, while the electron transfer resistance hardly changed. The nanopore based biosensor could sensitively detect biological ligands of benzaldehyde, docosahexaenoic acid, and lauric acid, which were closely related to or were potential biomarkers for cancers and other serious diseases. Equipped with hOBPs, the sensor exhibited promising potentials both in odorant and biomolecule detection for olfactory biosensing and in disease diagnosis and evaluation for biochemical detection. Copyright © 2015 Elsevier B.V. All rights reserved.

  7. Mechanistic characterization of aerobic alcohol oxidation catalyzed by Pd(OAc)(2)/pyridine including identification of the catalyst resting state and the origin of nonlinear [catalyst] dependence.

    Science.gov (United States)

    Steinhoff, Bradley A; Guzei, Ilia A; Stahl, Shannon S

    2004-09-15

    The Pd(OAc)(2)/pyridine catalyst system is one of the most convenient and versatile catalyst systems for selective aerobic oxidation of organic substrates. This report describes the catalytic mechanism of Pd(OAc)(2)/pyridine-mediated oxidation of benzyl alcohol, which has been studied by gas-uptake kinetic methods and (1)H NMR spectroscopy. The data reveal that turnover-limiting substrate oxidation by palladium(II) proceeds by a four-step pathway involving (1) formation of an adduct between the alcohol substrate and the square-planar palladium(II) complex, (2) proton-coupled ligand substitution to generate a palladium-alkoxide species, (3) reversible dissociation of pyridine from palladium(II) to create a three-coordinate intermediate, and (4) irreversible beta-hydride elimination to produce benzaldehyde. The catalyst resting state, characterized by (1)H NMR spectroscopy, consists of an equilibrium mixture of (py)(2)Pd(OAc)(2), 1, and the alcohol adduct of this complex, 1xRCH(2)OH. These in situ spectroscopic data provide direct support for the mechanism proposed from kinetic studies. The catalyst displays higher turnover frequency at lower catalyst loading, as revealed by a nonlinear dependence of the rate on [catalyst]. This phenomenon arises from a competition between forward and reverse reaction steps that exhibit unimolecular and bimolecular dependences on [catalyst]. Finally, overoxidation of benzyl alcohol to benzoic acid, even at low levels, contributes to catalyst deactivation by formation of a less active palladium benzoate complex.

  8. VOLATILE COMPOUNDS IN THE AROMA OF THREE SPECIES OF WOOD-ROTTING BASIDIOMYCETES AND THEIR ANTIFUNGAL POTENTIAL

    Directory of Open Access Journals (Sweden)

    Cristiana Virginia PETRE

    2017-12-01

    Full Text Available This study aims to determine the volatile organic compounds synthesized by three species of wood-rotting basidiomycetes: Coriolopsis gallica, Megacollybia platyphylla and Lentinus arcularius and test their antifungal potential. The species were cultivated on liquid media and kept for 25 days at 25 °C. The surface cultures were then homogenized, filtrated and extracted using solid-phase extraction and analyzed by GC-MS. The volatile compounds identified were mainly alcohols, ketones, aldehydes and terpenes. The most common volatiles identified in the experiment are: 1-octen-3-ol, 3-hexanol, 3-methyl-1-butanol, 3-octanone, 2-hexanone, benzaldehyde, and limonene. The volatiles metabolites of these species were tested for their antifungal activity using the bi-compartmented Petri dishes method against two species of plant pathogenic fungi: Fusarium solani and Sclerotinia sclerotiorum, on three media. The volatiles produced by Coriolopsis gallica showed the highest antifungal potential against the phytopathogens. The results revealed the importance of media composition in the synthesis of antifungal volatile compounds.

  9. Volatile Flavor Compounds Produced by Molds of Aspergillus, Penicillium, and Fungi imperfecti.

    Science.gov (United States)

    Kaminski, E; Stawicki, S; Wasowicz, E

    1974-06-01

    Strains of molds Aspergillus niger, A. ochraceus, A. oryzae, A. parasiticus, Penicillium chrysogenum, P. citrinum, P. funiculosum, P. raistrickii, P. viridicatum, Alternaria, Cephalosporium, and Fusarium sp. were grown on sterile coarse wheat meal at 26 to 28 C for 120 h. The volatiles from mature cultures were distilled at low temperature under reduced pressure. The distillates from traps -40 and -78 C were extracted with methylene chloride and subsequently concentrated. All the concentrates thus obtained were analyzed by gas-liquid chromatography, mass spectrometry, chemical reactions of functional groups, and olfactory evaluation. Six components detected in the culture distillates were identified positively: 3-methylbutanol, 3-octanone, 3-octanol, 1-octen-3-ol, 1-octanol, and 2-octen-1-ol. They represented 67 to 97% of all the volatiles occurring in the concentrated distillate. The following 14 components were identified tentatively: octane, isobutyl alcohol, butyl alcohol, butyl acetate, amyl acetate, octyl acetate, pyridine, hexanol, nonanone, dimethylpyrazine, tetramethylpyrazine, benzaldehyde, propylbenzene, and phenethyl alcohol. Among the volatiles produced by molds, 1-octen-3-ol yielding a characteristic fungal odor was found predominant.

  10. Multiple headspace-solid-phase microextraction: an application to quantification of mushroom volatiles.

    Science.gov (United States)

    Costa, Rosaria; Tedone, Laura; De Grazia, Selenia; Dugo, Paola; Mondello, Luigi

    2013-04-03

    Multiple headspace-solid phase microextraction (MHS-SPME) followed by gas chromatography/mass spectrometry (GC-MS) and flame ionization detection (GC-FID) was applied to the identification and quantification of volatiles released by the mushroom Agaricus bisporus, also known as champignon. MHS-SPME allows to perform quantitative analysis of volatiles from solid matrices, free of matrix interferences. Samples analyzed were fresh mushrooms (chopped and homogenized) and mushroom-containing food dressings. 1-Octen-3-ol, 3-octanol, 3-octanone, 1-octen-3-one and benzaldehyde were common constituents of the samples analyzed. Method performance has been tested through the evaluation of limit of detection (LoD, range 0.033-0.078 ng), limit of quantification (LoQ, range 0.111-0.259 ng) and analyte recovery (92.3-108.5%). The results obtained showed quantitative differences among the samples, which can be attributed to critical factors, such as the degree of cell damage upon sample preparation, that are here discussed. Considerations on the mushrooms biochemistry and on the basic principles of MHS analysis are also presented. Copyright © 2013 Elsevier B.V. All rights reserved.

  11. Differences in the volatile compositions of French labeled brandies (Armagnac, Calvados, Cognac, and Mirabelle) using GC-MS and PLS-DA.

    Science.gov (United States)

    Ledauphin, Jérôme; Le Milbeau, Claude; Barillier, Daniel; Hennequin, Didier

    2010-07-14

    A total of 207 volatile compounds were identified in extracts of four French labeled brandies: Armagnac, Cognac, Calvados, and Mirabelle. Relative levels of all components were determined using GC-MS after integration of a selected peak of the mass spectrum of each. Each type of brandy could be clearly discriminated using PLS-DA statistical analyses based on these levels. French Mirabelle spirit, which was studied for the first time, was characterized by higher levels of many aldehydes and acetals and by the presence of compounds having an odd number of carbons together with benzaldehyde and some of its derivatives. Many possible derivatives of acrolein and high amounts of butan-2-ol were rather specific for the volatile composition of Calvados. The most important difference between the two wine-based samples seemed to be directly linked to the distillation system used. Many furanic compounds are specific to Cognac, whereas two or three compounds such as 1-(ethoxyethoxy)-2-methylbutane and gamma-eudesmol were specific to Armagnac. These two brandies presented rather high distributions of isobutanol and isopentanols, whereas Mirabelle and Calvados compositions offer more concentrated aliphatic linear alcohols.

  12. Ligand-tailored single-site silica supported titanium catalysts: Synthesis, characterization and towards cyanosilylation reaction

    Science.gov (United States)

    Xu, Wei; Li, Yani; Yu, Bo; Yang, Jindou; Zhang, Ying; Chen, Xi; Zhang, Guofang; Gao, Ziwei

    2015-01-01

    A successive anchoring of Ti(NMe2)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 silica was conducted by SOMC strategy in moderate conditions. The silica, monitored by in-situ Fourier transform infrared spectroscopy (in-situ FT-IR), was pretreated at different temperatures (200, 500 and 800 °C). The ligand tailored silica-supported titanium complexes were characterized by in-situ FT-IR, 13C CP MAS-NMR, X-ray photoelectron spectroscopy (XPS), X-ray absorption near edge structure (XANES) and elemental analysis in detail, verifying that the surface titanium species are single sited. The catalytic activity of the ligand tailored single-site silica supported titanium complexes was evaluated by a cyanosilylation of benzaldehyde. The results showed that the catalytic activity is dependent strongly on the dehydroxylation temperatures of silica and the configuration of the ligands.

  13. Bifunctional nanocrystalline MgO for chiral epoxy ketones via Claisen-Schmidt condensation-asymmetric epoxidation reactions.

    Science.gov (United States)

    Choudary, Boyapati M; Kantam, Mannepalli L; Ranganath, Kalluri V S; Mahendar, Koosam; Sreedhar, Bojja

    2004-03-24

    Design and development of a truly nanobifunctional heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with acetophenones to yield chalcones quantitatively followed by asymmetric epoxidation (AE) to afford chiral epoxy ketones with moderate to good yields and impressive ee's is described. The nanomagnesium oxide (aerogel prepared) NAP-MgO was found to be superior over the NA-MgO and CM-MgO in terms of activity and enantioselectivity as applicable in these reactions. An elegant strategy for heterogenization of homogeneous catalysts is presented here to evolve single-site chiral catalysts for AE by a successful transfer of molecular chemistry to surface metal-organic chemistry with the retention of activity, selectivity/enantioselectivity. Brønsted hydroxyls are established as sole contributors for the epoxidation reaction, while they add on to the CSC, which is largely driven by Lewis basic O2-sites. Strong hydrogen-bond interactions between the surface -OH on MgO and -OH groups of diethyl tartrate are found inducing enantioselectivity in the AE reaction. Thus, the nanocrystalline NAP-MgO with its defined shape, size, and accessible OH groups allows the chemisorption of TBHP, DET, and olefin on its surface to accomplish single-site chiral catalysts to provide optimum ee's in AE reactions.

  14. Single-site SBA-15 supported zirconium catalysts. Synthesis, characterization and toward cyanosilylation reaction

    Science.gov (United States)

    Xu, Wei; Yu, Bo; Zhang, Ying; Chen, Xi; Zhang, Guofang; Gao, Ziwei

    2015-01-01

    A successive anchoring of Zr(NMe2)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-15-500) 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-15-500 supported zirconium complexes were characterized by in situ FT-IR, 13C 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.

  15. Synthesis and Biological Evaluation of Novel 6-Hydroxy-benzo[d][1,3]oxathiol-2-one Schiff Bases as Potential Anticancer Agents

    Directory of Open Access Journals (Sweden)

    Eliza de Lucas Chazin

    2015-01-01

    Full Text Available With the aim of discovering new anticancer agents, we have designed and synthesized novel 6-hydroxy-benzo[d][1,3]oxathiol-2-one Schiff bases. The synthesis started with the selective nitration at 5-position of 6-hydroxybenzo[d][1,3]oxathiol-2-one (1 leading to the nitro derivative 2. The nitro group of 2 was reduced to give the amino intermediate 3. Schiff bases 4a–r were obtained from coupling reactions between 3 and various benzaldehydes and heteroaromatic aldehydes. All the new compounds were fully identified and characterized by NMR (1H and 13C and specifically for 4q by X-ray crystallography. The in vitro cytotoxicity of the compounds was evaluated against cancer cell lines (ACP-03, SKMEL-19 and HCT-116 by using MTT assay. Schiff bases 4b and 4o exhibited promising cytotoxicity against ACP-03 and SKMEL-19, respectively, with IC50 values lower than 5 μM. This class of compounds can be considered as a good starting point for the development of new lead molecules in the fight against cancer.

  16. Designing, synthesis and spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies

    Directory of Open Access Journals (Sweden)

    N. RAMAN

    2008-10-01

    Full Text Available 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 type. The UV–Vis and ESR spectral data of the complexes suggested a square-planar geometry around the central metal ion. The magnetic susceptibility values of the complexes indicated that they were monomeric in nature. Antimicrobial screening tests were also performed against four bacteria, viz. Salmonella typhi, Staphylococcus aureus, Escherichia coli, and Bacillus subtilis and three fungi, viz. Aspergillus niger, Aspergillus flavus and Rhizoctonia bataicola. These data gave good results in the presence of metal ion in the ligand system. The nuclease activity of the above metal complexes shows that only the copper complex cleaves CT DNA in the presence of an oxidant.

  17. DNA cleavage, structural elucidation and anti-microbial studies of three novel mixed ligand Schiff base complexes of copper(II

    Directory of Open Access Journals (Sweden)

    N. RAMAN

    2007-10-01

    Full Text Available Three new copper complexes of mixed ligands derived from Schiff bases (condensation of p-aminoacetanilide and substituted benzaldehydes with 1,10-phenanthroline have been synthesized and characterized by elemental analysis, IR, UV–Vis, magnetic moments, conductivity and electrochemical measurements. The spectral techniques suggest that all the copper complexes exhibit octahedral geometry. The low electrical conductance of the complexes supports their neutral nature. The monomeric nature of the complexes was assessed from their magnetic susceptibility values. The in vitro biological screening effects of the investigated compounds were tested against the bacteria Escherichia coli, Staphylococcus aureus, and Salmonella typhi and the fungi Rhizopus stolonifer and Candida albicans by the serial dilution method. A comparative study of the MIC values of the Schiff bases and their copper complexes indicates that the metal complexes exhibited higher antibacterial activity than the free ligands. The DNA cleavage ability of the complexes was monitored by the gel electrophoresis technique. It was found that electron withdrawing group substituted copper complex had higher DNA cleavage activity than the other copper complexes.

  18. Synthesis, characterization and biological studies of copper(II) complexes with 2-aminobenzimidazole derivatives

    Science.gov (United States)

    Joseph, J.; Suman, A.; Nagashri, K.; Joseyphus, R. Selwin; Balakrishnan, Nisha

    2017-06-01

    Novel series of four copper(II) complexes with 2-aminobenzimidazole derivatives (obtained from the Knoevenagel condensate of acetylacetone (obtained from acetylacetone and halogen substituted benzaldehydes) and 2-aminobenzimidazole) were synthesized. They were structurally characterized using elemental analysis, molar conductance, FAB mass, FT- IR, 1H &13C-NMR, UV-Vis., and EPR techniques. On the basis of analytical and spectral studies, the distorted square planar geometry was assigned for all the complexes. The antibacterial screening of the ligands and their copper complexes indicated that all the complexes showed higher anti microbial activities than the free ligands. Superoxide dismutase and antioxidant activities of the copper complexes have also been performed. In the electrochemical technique, the shift in ΔEp, E1/2 and Ipc values were explored for the interaction of the complexes with CT-DNA. During the electrolysis process, the present ligand system stabilizes unusual oxidation state of copper in the complexes. It is believed that the copper complexes with curcumin analogs may enhance chemotherapeutic behavior.

  19. Synthetic bioactive novel ether based Schiff bases and their copper(II) complexes

    Science.gov (United States)

    Shabbir, Muhammad; Akhter, Zareen; Ismail, Hammad; Mirza, Bushra

    2017-10-01

    Novel ether based Schiff bases (HL1- HL4) were synthesized from 5-chloro-2-hydroxy benzaldehyde and primary amines (1-amino-4-phenoxybenzene, 4-(4-aminophenyloxy) biphenyl, 1-(4-aminophenoxy) naphthalene and 2-(4-aminophenoxy) naphthalene). From these Schiff bases copper(II) complexes (Cu(L1)2-Cu(L4)2)) were synthesized and characterized by elemental analysis and spectroscopic (FTIR, NMR) techniques. The synthesized Schiff bases and copper(II) complexes were further assessed for various biological studies. In brine shrimp assay the copper(II) complexes revealed 4-fold higher activity (LD50 3.8 μg/ml) as compared with simple ligands (LD50 12.4 μg/ml). Similar findings were observed in potato disc antitumor assay with higher activities for copper(II) complexes (IC50 range 20.4-24.1 μg/ml) than ligands (IC50 range 40.5-48.3 μg/ml). DPPH assay was performed to determine the antioxidant potential of the compounds. Significant antioxidant activity was shown by the copper(II) complexes whereas simple ligands have shown no activity. In DNA protection assay significant protection behavior was exhibited by simple ligand molecules while copper(II) complexes showed neutral behavior (neither protective nor damaging).

  20. Sequence-controlled copolymers of 2,3,4,5-pentafluorostyrene: Mechanistic insight and application to organocatalysis

    KAUST Repository

    O'Shea, John Paul

    2014-01-01

    A number of copolymers between styrene (St) or 4-azidomethylstyrene (N 3St) and 2,3,4,5,6-pentafluorostyrene (FSt) have been prepared by atom-transfer radical polymerization (ATRP) and conventional free radical polymerization (FRP). The mode of monomer alternation in copolymers has been established unambiguously using heteronuclear multiple bond correlation (HMBC) NMR. The degree and nature of monomer alternation was found to be strongly dependent on both the solvent (or lack thereof) and the polymerization initiator. These results are in contrast to previously published studies, which rely primarily on classic analysis of monomer reactivity ratios. We proceeded to independently functionalize the N3St and FSt moieties using orthogonal "click" chemistries: copper-catalyzed azide-alkyne cycloaddition (CuAAC) and fluoroarene-thiol coupling (FTC). An alternating copolymer bearing -NH2 and -SO3 - functional groups was found to be a competent organocatalyst for a Henry reaction between benzaldehyde and nitromethane. This journal is © 2014 The Royal Society of Chemistry.

  1. Electrodeposition of thin Pd-Ag films

    International Nuclear Information System (INIS)

    Hasler, P.; Allmendinger, T.

    1993-01-01

    Thin Pd-Ag layers were electroplated preferably on brass and on nickel substrates using a two-compartment cell separated by an anion exchange membrane. The weakly alkaline electrolyte contained glycine-glycinate as the major complexing agents. The plating experiments were usually carried out without stirring, at different potentials and temperatures and in the absence or in the presence of sodium benzaldehyde-2,4-disulphonate (BDS). The samples were characterized by scanning electron microscopy and light microscopy. Their compositions were determined analytically by the inductively coupled plasma technique. In addition, the film porosity was tested. Electrodeposition in almost limiting current conditions for both components and without simultaneous hydrogen evolution led to deposits with compositions being in good agreement with the molar metal ratio in the electrolyte (77:23). The best results were achieved between 0 and -50 mV with respect to a reversible hydrogen electrode at 0 C in the presence of BDS. These deposits were bright, had good adherence and exhibited no pores at a film thickness of 1.2 μm. At too negative potentials, the deposits became black and powdery. (orig.)

  2. Tumor cell heterogeneity: impact on mechanisms of therapeutic drug resistance

    International Nuclear Information System (INIS)

    Richardson, Mary E.; Siemann, Dietmar W.

    1997-01-01

    Purpose: The aim of these studies was to determine whether chemotherapy-resistant tumor cell sublines derived from a single starting cell population with identical treatment protocols, have the same mechanism of resistance. Methods and Materials: Twelve cyclophosphamide-resistant sublines were derived from KHT-iv murine sarcoma cells by repeated exposures to 2, 4, or 8 μg/ml doses of 4-hydroperoxycyclophosphamide (4-OOHCP). To investigate possible mechanisms of resistance, glutathione (GSH) levels, glutathione S-transferase (GST) activity, and aldehyde dehydrogenase (ALDH) activity were determined. In addition, studies with the GSH depletor buthionine sulfoximine (BSO) and the ALDH inhibitor diethylamino-benzaldehyde (DEAB) were undertaken. Results: Resistant factors to 4-OOHCP, assessed at 10% clonogenic cell survival, ranged from 1.5-7.0 for the various cell lines. Crossresistance to melphalan and adriamycin also were commonly observed. Increased GSH levels, GST activity and ALDH activity were detected in the sublines but not all exhibited the same pattern of biochemical alterations. The response to GSH and ALDH inhibitors also varied among the sublines; the resistance being reversible in some cell lines but not others. Conclusion: The present results indicate that when resistant sublines are derived simultaneously from the same starting cell population, the observed mechanisms of resistance may not be the same in each of the variants. These findings support the hypothesis that preexisting cellular heterogeneity may affect mechanisms of acquired resistance

  3. In-tube extraction for the determination of the main volatile compounds in Physalis peruviana L.

    Science.gov (United States)

    Kupska, Magdalena; Jeleń, Henryk H

    2017-01-01

    An analytical procedure based on in-tube extraction followed by gas chromatography with mass spectrometry has been developed for the analysis of 24 of the main volatile components in cape gooseberry (Physalis peruviana L.) samples. According to their chemical structure, the compounds were organized into different groups: one hydrocarbon, one aldehyde, four alcohols, four esters, and 14 monoterpenes. By single-factor experiments, incubation temperature, incubation time, extraction volume, extraction strokes, extraction speed, desorption temperature, and desorption speed were determined as 60°C, 20 min, 1000 μL, 20, 50:50 μL/s, 280°C, 100 μL/s, respectively. Quantitative analysis using authentic standards and external calibration curves was performed. The limit of detection and limit of quantification for the analytical procedure were calculated. Results shown the benzaldehyde, ethyl butanoate, 2-methyl-1-butanol, 1-hexanol, 1-butanol, α-terpineol, and terpinen-4-ol were the most abundant volatile compounds in analyzed fruits (68.6-585 μg/kg). The obtained data may contribute to qualify cape gooseberry to the group of superfruits and, therefore, increase its popularity. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  4. Efficient synthesis of benzothiazine and acrylamide compounds

    Energy Technology Data Exchange (ETDEWEB)

    Souza, Ana Maria Alves; Walfrido, Simone Torres Padua; Leite, Lucia Fernanda Costa; Lima, Maria Carmo Alves; Galdino, Suely Lins; Pitta, Ivan Rocha [Universidade Federal de Pernambuco (UFPE), Recife, PE (Brazil). Dept. de Antibioticos; Barbosa Filho, Jose Maria [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil); Simone, Carlos Alberto de; Ellena, Javier Alcides, E-mail: irpitta@gmail.co [Universidade de Sao Paulo (USP), Sao Carlos, SP (Brazil). Inst. de Fisica

    2010-07-01

    This article describes the synthesis of the new (2Z)-2-(4-methoxybenzylidene)-6-nitro-4H -benzo[1,4]thiazine-3-one, (2Z)-2-(4-methoxybenzylidene)-4-methyl-6-nitro-4H-benzo[1,4]thiazine-3-one, (2Z)-6-amino-2-(4-methoxybenzylidene)-4H -benzo[1,4]thiazine-3-one, (2Z)-6-butylamino-2-(4-methoxybenzylidene)-4-methyl-4H-benzo[1,4] -thiazine-3-one and (2E)-N-alkyl-N-(2-hydroxy-5-nitrophenyl) -3-phenylacrylamides and the spectroscopic data. The arylidenebenzothiazine compounds were prepared using the Knoevenagel condensation with substituted benzaldehydes in the presence of sodium methoxide in DMF. The presence of a nitro substituent in the 4-position, water and a slightly acid reaction medium in this condensation caused the rupture of the benzothiazine ring and subsequent formation of the phenylacrylamide compounds. A crystallographic data was presented for (2E)-3-(4-bromophenyl)-N-dodecyl-N -(2-hydroxy-5-nitrophenyl) acrylamide. (author)

  5. Studying Plant–Insect Interactions with Solid Phase Microextraction: Screening for Airborne Volatile Emissions Response of Soybeans to the Soybean Aphid, Aphis glycines Matsumura (Hemiptera: Aphididae

    Directory of Open Access Journals (Sweden)

    Lingshuang Cai

    2015-05-01

    Full Text Available Insects trigger plants to release volatile compounds that mediate the interaction with both pest and beneficial insects. Soybean aphids (Aphis glycines induces soybean (Glycine max leaves to produce volatiles that attract predators of the aphid. In this research, we describe the use of solid-phase microextraction (SPME for extraction of volatiles from A. glycines-infested plant. Objectives were to (1 determine if SPME can be used to collect soybean plant volatiles and to (2 use headspace SPME-GC-MS approach to screen compounds associated with A. glycines-infested soybeans, grown in the laboratory and in the field, to identify previously known and potentially novel chemical markers of infestation. A total of 62 plant volatiles were identified, representing 10 chemical classes. 39 compounds had not been found in previous studies of soybean volatile emissions. 3-hexen-1-ol, dimethyl nonatriene, indole, caryophyllene, benzaldehyde, linalool, methyl salicylate (MeSA, benzene ethanol, and farnesene were considered herbivore-induced plant volatiles (HIPVs. For reproductive field-grown soybeans, three compounds were emitted in greater abundance from leaves infested with A. glycines, cis-3-hexen-1-ol acetate, MeSA and farnesene. In summary, SPME can detect the emission of HIPVs from plants infested with insect herbivores.

  6. Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions.

    Science.gov (United States)

    Hernández, Karel; Parella, Teodor; Joglar, Jesús; Bujons, Jordi; Pohl, Martina; Clapés, Pere

    2015-02-16

    The introduction of aromatic residues connected by a C-C bond into the non-reducing end of carbohydrates is highly significant for the development of innovative structures with improved binding affinity and selectivity (e.g., C-aril-sLex). In this work, an expedient asymmetric "de novo" synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation reactions is presented. First, the benzoin reaction of aromatic aldehydes to dimethoxyacetaldehyde is conducted, catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I. Then, the α-hydroxyketones formed are reduced by using NaBH4 yielding the anti diol. After acetal hydrolysis, the aldol addition of dihydroxyacetone, hydroxyacetone, or glycolaldehyde catalyzed by the stereocomplementary D-fructose-6-phosphate aldolase and L-rhamnulose-1-phosphate aldolase is performed. Both aldolases accept unphosphorylated donor substrates, avoiding the need of handling the phosphate group that the dihydroxyacetone phosphate-dependent aldolases require. In this way, 6-C-aryl-L-sorbose, 6-C-aryl-L-fructose, 6-C-aryl-L-tagatose, and 5-C-aryl-L-xylose derivatives are prepared by using this methodology. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  7. Synthesis, characterization, antibacterial and antifungal studies of some transition and rare earth metal complexes of N-benzylidene-2-hydroxybenzohydrazide

    Directory of Open Access Journals (Sweden)

    T.K. Chondhekar

    2011-12-01

    Full Text Available The solid complexes of Cu(II, Co(II, Mn(II, La(III and Ce(III were prepared from bidentate Schiff base, N-benzylidene-2-hydroxybenzohydrazide. The Schiff base ligand was synthesized from 2-hyhdroxybenzohydrazide and benzaldehyde. These metal complexes were characterized by molar conductivity, magnetic susceptibility, thermal analysis, X-ray diffraction, FTIR, 1H-NMR, UV-Vis and mass spectroscopy. The analytical data of these metal complexes showed metal:ligand ratio of 1:2. The physico-chemical study supports the presence of square planar geometry around Cu(II and octahedral geometry around Mn(II, Co(II, La(III and Ce(III ions. The IR spectral data reveal that the ligand behaves as bidentate with ON donor atom sequence towards central metal ion. The molar conductance values of metal complexes suggest their non-electrolyte nature. The X-ray diffraction data suggest monoclinic crystal system for these complexes. Thermal behavior (TG/DTA and kinetic parameters calculated by Coats-Redfern method are suggestive of more ordered activated state in complex formation. The ligand and their metal complexes were screened for antibacterial activity against Staphylococcus aureus and Escherichia coli and fungicidal activity against Aspergillus niger and Trichoderma.

  8. Synergistic effect in the oxidation of benzyl alcohol using citrate-stabilized gold bimetallic nanoparticles supported on alumina

    Science.gov (United States)

    Gómez-Villarraga, Fernando; Radnik, Jörg; Martin, Andreas; Köckritz, Angela

    2016-06-01

    Bimetallic nanoparticles (NPs) containing gold and various second metals ( M = Pd, Pt, Cu, and Ag) supported on alumina (AuM/Alumina) were prepared using sodium citrate as stabilizer. In addition, supported monometallic Au/Alumina and Pd/Alumina were synthesized and tested to reveal synergistic effects in the catalytic evaluation of the bimetallic catalysts. The monometallic and bimetallic NPs revealed average sizes below 10 nm. The oxidation of benzyl alcohol with molecular oxygen as oxidant at mild conditions in liquid phase in the absence and presence (toluene or NaOH aqueous solution, 0.2 M) of a solvent was selected as test reaction to evaluate the catalytic properties of the above-mentioned solids. AuPd/Alumina exhibited the best catalytic activity among all bimetallic catalysts using toluene as solvent and under solvent-free conditions, respectively. In comparison to the monometallic catalysts, a synergistic effect with AuPd/Alumina was only evident in the solvent-free reaction. The AuPd/Alumina catalyst was able to oxidize benzyl alcohol selectively depending on the reaction medium into benzaldehyde (toluene or solvent-free) or benzoic acid (NaOH aqueous solution, 0.2 M). However, the catalyst deactivated due to particle growth of the bimetallic AuPd NPs by Ostwald ripening and leaching was not observed in the oxidation using toluene as solvent. The size of the catalytically active NPs, the metal composition of the particles, and the reaction conditions greatly influenced the catalytic oxidation results.

  9. Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.

    Science.gov (United States)

    Poisson, Luigi; Schieberle, Peter

    2008-07-23

    Application of the aroma extract dilution analysis (AEDA) on the volatile fraction carefully isolated from an American Bourbon whisky revealed 45 odor-active areas in the flavor dilution (FD) factor range of 32-4096 among which (E)-beta-damascenone and delta-nonalactone showed the highest FD factors of 4096 and 2048, respectively. With FD factors of 1024, (3S,4S)-cis-whiskylactone, gamma-decalactone, 4-allyl-2-methoxyphenol (eugenol), and 4-hydroxy-3-methoxy-benzaldehyde (vanillin) additionally contributed to the overall vanilla-like, fruity, and smoky aroma note of the spirit. Application of GC-Olfactometry on the headspace above the whisky revealed 23 aroma-active odorants among which 3-methylbutanal, ethanol, and 2-methylbutanal were identified as additional important aroma compounds. Compared to published data on volatile constituents in whisky, besides ranking the whisky odorants on the basis of their odor potency, 13 aroma compounds were newly identified in this study: ethyl (S)-2-methylbutanoate, (E)-2-heptenal, (E,E)-2,4-nonadienal, (E)-2-decenal, (E,E)-2,4-decadienal, 2-isopropyl-3-methoxypyrazine, ethyl phenylacetate, 4-methyl acetophenone, alpha-damascone, 2-phenylethyl propanoate, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, trans-ethyl cinnamate, and (Z)-6-dodeceno-gamma-lactone.

  10. UV spectra and OH-oxidation kinetics of gaseous phase morpholinic compounds

    KAUST Repository

    Rachidi, Mariam El

    2014-05-01

    This paper presents an experimental study of the UV spectra as well as the kinetics of gaseous phase OH-oxidation of morpholine, N-formylmorpholine (NFM) and N-acetlymorpholine (NAM). The spectra recorded using a UV spectrometer in the spectral range 200-280nm show that the analytes mainly absorb at wavelengths less than 280nm. This indicates that their photolysis potential in the troposphere is insignificant. Meanwhile, the OH-reactivity of these analytes was studied using a triple-jacket 2m long reactor equipped with a multi-reflection system and coupled to an FTIR spectrometer. The experiments were carried out at 295 and 313K for the amine and amides, respectively. The study was conducted in the relative mode using isoprene and benzaldehyde as reference compounds. The rate constants obtained are 14.0±1.9, 4.0±1.1 and 3.8±1.0 (in units of 10-11cm3molecule-1s-1) for morpholine, NFM and NAM respectively. These results are discussed in terms of reactivity and compared to those obtained for other oxy-nitrogenated species. In addition, the determined rate constants are used to estimate effective atmospheric lifetimes of the investigated morpholinic compounds with respect to reaction with OH radicals. © 2014 Elsevier Ltd.

  11. Evaluating the antibacterial and anticandidal potency of mangrove, Avicennia marina

    Directory of Open Access Journals (Sweden)

    Aseer Manilal

    2016-02-01

    Full Text Available Objective: To evaluate the antibiotic activity of mangrove plant, Avicennia marina (A. marina against human and shrimp pathogens and to delineate bioactive constituents by gas chromatography-mass spectrometer (GC-MS profiling. Methods: The antimicrobial activity of the different polar and non-polar extracts of A. marina was inspected by well diffusion technique against 16 bacterial pathogens and two fungal pathogens. Results: Of the six organic extracts examined, methanolic extract of A. marina fairly repressed the growth of all bacterial and fungal pathogenic strains tested. In general, mangrove extract was more active against the bacterial pathogens while against yeasts, the activity was lesser. The antibiotic activity was attributed to the presence of diverse bioactive secondary metabolites. The chemical profiling of the methanolic extract was performed by GC combined with mass spectrometry. The results of GC-MS showed that the main phytoconstituents were benzeneethanol,4-hydroxy- (RT = 12.173, followed by benzaldehyde,3-methyl- (RT = 6.811. Finally, the GC-MS data evinced that the antimicrobial activity of A. marina was due to the synergistic effect of all constituents or the activity of major constituents. Conclusions: Considering the urgent need of novel antibiotics, the present study brings out a new insight on the exploration of mangroves for antibiotic production in future.

  12. Biocatalytic Behaviour of Immobilized Rhizopus oryzae Lipase in the 1,3-Selective Ethanolysis of Sunflower Oil to Obtain a Biofuel Similar to Biodiesel

    Directory of Open Access Journals (Sweden)

    Carlos Luna

    2014-08-01

    Full Text Available A new biofuel similar to biodiesel was obtained in the 1,3-selective transesterification reaction of sunflower oil with ethanol using as biocatalyst a Rhizopus oryzae lipase (ROL immobilized on Sepiolite, an inorganic support. The studied lipase was a low cost powdered enzyme preparation, Biolipase-R, from Biocon-Spain, a multipurpose additive used in food industry. In this respect, it is developed a study to optimize the immobilization procedure of these lipases on Sepiolite. Covalent immobilization was achieved by the development of an inorganic-organic hybrid linker formed by a functionalized hydrocarbon chain with a pendant benzaldehyde, bonded to the AlPO4 support surface. Thus, the covalent immobilization of lipases on amorphous AlPO4/sepiolite (20/80 wt % support was evaluated by using two different linkers (p-hydroxybenzaldehyde and benzylamine-terephthalic aldehyde, respectively. Besides, the catalytic behavior of lipases after physical adsorption on the demineralized sepiolite  was also evaluated. Obtained results indicated that covalent immobilization with the p-hydroxybenzaldehyde linker gave the best biocatalytic behavior. Thus, this covalently immobilized lipase showed a remarkable stability as well as an excellent capacity of reutilization (more than five successive reuses without a significant loss of its initial catalytic activity. This could allow a more efficient fabrication of biodiesel minimizing the glycerol waste production.

  13. Green One-pot Synthesis of Novel Polysubstituted Pyrazole Derivatives as Potential Antimicrobial Agents.

    Science.gov (United States)

    Beyzaei, Hamid; Motraghi, Zahra; Aryan, Reza; Zahedi, Mohammad Mehdi; Samzadeh-Kermani, Alireza

    2017-12-01

    Various biological properties of natural and synthetic pyrazole derivatives such as anti-inflammatory, antimicrobial, neuroprotective, anticonvulsant, antidepressant and anticancer activities encouraged us to propose a new, fast, green and eco-friendly procedure for the preparation of some novel 5-amino-3-(aryl substituted)-1-(2,4-dinitrophenyl)-1H-pyrazole-4-carbonitriles. They were efficiently synthesized via one-pot two-step process reaction of malononitrile, 2,4-dinitrophenylhydrazine and different benzaldehydes in deep eutectic solvent (DES) glycerol/potassium carbonate. The products yield and reaction times were considerably improved in the presence of applied DES. Antibacterial effects of all newly synthesized pyrazoles in comparison with several common antibiotics were evaluated against a variety of Gram-positive and Gram-negative pathogenic bacteria. In addition to, their inhibitory activities on three fungi were compared to some current antifungal agents. The moderate to good antimicrobial potentials particularly against fungi were observed in the major heterocyclic compounds according to the IZD, MIC, MBC and MFC results.

  14. Electronic states of o-nitrobenzaldehyde: a combined experimental and theoretical study.

    Science.gov (United States)

    Leyva, Verónica; Corral, Inés; Schmierer, Thomas; Heinz, Björn; Feixas, Ferran; Migani, Annapaola; Blancafort, Lluís; Gilch, Peter; González, Leticia

    2008-06-12

    The experimental UV/vis absorption spectrum of ortho-nitrobenzaldehyde (o-NBA) has been assigned by means of MS-CASPT2/CASSCF, TD-DFT, and RI-CC2 theoretical computations. Additional information on the nature of the absorbing bands was obtained by comparing the o-NBA spectrum with that of related compounds, as, e.g., nitrobenzene and benzaldehyde. For wavelengths larger than approximately 280 nm, the absorption spectrum of o-NBA is dominated by a series of weak n pi* absorptions from the NO2 and CHO groups. These weak transitions are followed in energy by a more intense band, peaking at 250 nm and arising from charge transfer pi pi* excitations involving mainly benzene and nitro orbitals. Finally, the most intense band centered at 220 nm has its origin in the overlap of two different absorptions: the first one localized in the NO2 substituent and the second one arising from a charge transfer excitation involving the NO2 and the CHO fragments, respectively.

  15. The assesment of the food quality by 13 C isotope ratio mass spectrometry

    International Nuclear Information System (INIS)

    Cuna, Stela; Cuna, Cornel

    2001-01-01

    Carbon 13 analysis can be a key analytical technique used in the fight to detect undeclared addition of low cost adulterants to high value foods. The natural abundance of 13 C in food is related to how the plant fix the carbon during photosynthesis. Plants that use a C3 photosynthetic cycle discriminate against 13 C more than plants with C4 cycle. We developed a method for analysis of 13 C isotope in organic samples. Because of instrumental requirements carbon must be converted to CO 2 for stable isotope ratio measurements. Conversion of organic samples to CO 2 was accomplished by combustion in an excess oxygen atmosphere. This technique involves the combustion of individual samples in sealed, evacuated quartz tubes containing CuO as the oxygen source. Because each sample is prepared in its own container, there is no chance for memory effects. The method was tested for sensitivity (the smallest increment of the isotope ratio that must be detected with confidence), sample size (the minimum quantity of a pure molecular species available to achieve the desired accuracy) and precision. The method was utilised for the detection of a synthetic flavour from natural one, namely the natural oil bitter almond from the synthetic benzaldehyde. The method can be validated for the detection or establishment of authenticity in food products. (authors)

  16. Free and glycosidically bound aroma compounds in cherry (Prunus avium L.).

    Science.gov (United States)

    Wen, Ya-Qin; He, Fei; Zhu, Bao-Qing; Lan, Yi-Bin; Pan, Qiu-Hong; Li, Chun-You; Reeves, Malcolm J; Wang, Jun

    2014-01-01

    This paper reports the occurrence of both free and glycosidically bound aroma compounds in three sweet cherry cultivars ('Hongdeng', 'Hongyan' and 'Rainier'), with 97 compounds being identified in the three cultivars. The major free volatile compounds found were hexanal, (E)-2-hexenal, (E)-2-hexen-1-ol, benzyl alcohol and benzaldehyde. The major bound volatile compounds found were benzyl alcohol, geraniol, 2-phenylethanol. Also 4-vinylphenol was found in cherry fruit for the first time, and has a relatively high concentration of the glycosidically-bound form in 'Rainier'. Odour activity values (OAVs) were determined for both free and bound volatiles, with 18 compounds having an OAV above 1. The highest OAVs for three cultivars were (E)-β-ionone, hexanal, decanal and (E)-2-hexenal with the highest being over 800 for (E)-β-ionone in 'Honyang'. From these results, it was concluded that the aroma compounds present were similar in all three cultivars, but there was significant variation found in their levels and hence contribution to the aroma of these cultivars. Copyright © 2013 Elsevier Ltd. All rights reserved.

  17. Phenolic Compounds, Volatiles, and Sensory Characteristics of Twelve Sweet Cherry (Prunus avium L.) Cultivars Grown in Turkey.

    Science.gov (United States)

    Hayaloglu, Ali Adnan; Demir, Nurullah

    2016-01-01

    The paper reports the phenolic, anthocyanin, and volatile compounds and sensory characteristics of 12 cultivars of sweet cherries including cvs. Belge, Bing, Dalbasti, Durona di Cesena, Lambert, Merton Late, Starks Gold, Summit, Sweetheart, Van, Vista, and 0-900 Ziraat. Eight individual phenolic compounds were determined by the HPLC-DAD method. Among these cherries, cvs. Bing, Durona di Cesena, and Lambert contained higher levels of total individual phenolic compounds than the other cultivars. Six anthocyanins were detected in cherries and cyanidin-3-O-rutinoside was principal and it was the highest level in cv. Bing. The major volatiles found were 1-hexanol, (E)-2-hexen-1-ol, benzylalcohol, hexenal, (E)-2-hexenal, and benzaldehyde. Sensory evaluation of the cherries showed that cvs. Belge, Bing, Dalbasti, and Summit have higher textural and flavor scores than others. It was concluded that the same compounds for phenolic or volatiles profiles of sweet cherries were similar in qualitative; however, quantitative differences were observed in these cultivars. © 2015 Institute of Food Technologists®

  18. Antispasmodic activity of xanthoxyline derivatives: structure-activity relationships.

    Science.gov (United States)

    Cechinel Filho, V; Miguel, O G; Nunes, R J; Calixto, J B; Yunes, R A

    1995-04-01

    The antispasmodic activity of several xanthoxyline derivatives against acetylcholine-induced contraction of the guinea pig ileum was evaluated in vitro. The acetophenones with two methoxyl groups, mainly in the 3,4 positions, exhibited potent antispasmodic activity. Modification of the hydroxyl group in xanthoxyline by the introduction of benzoyl, acetyl, or tosyl groups produced inactive compounds, whereas the introduction of benzyl or p-methoxybenzyl groups furnished compounds that were four- to eight-fold more potent than xanthoxyline. In marked contrast, the introduction of a methyl group gave a compound that caused contractant activity. Modification of the carbonyl group of xanthoxyline lead to inactive compounds, whereas the condensation of xanthoxyline with benzaldehydes gave chalkones that were about fivefold more potent than xanthoxyline. The introduction of benzyl and styrene groups, on the basis of the similarity with papaverine, improves the antispasmodic action of the xanthoxyline derivates. Our results suggest that the methoxyl and carbonyl groups are critical structural points for the antispasmodic activity of xanthoxyline derivatives. The hydroxyl group improves antispasmodic activity, but is not fundamental to its manifestation.

  19. Study of the antibacterial and antifungal activities of synthetic benzyl bromides, ketones, and corresponding chalcone derivatives.

    Science.gov (United States)

    Shakhatreh, Muhamad Ali K; Al-Smadi, Mousa L; Khabour, Omar F; Shuaibu, Fatima A; Hussein, Emad I; Alzoubi, Karem H

    2016-01-01

    Several applications of chalcones and their derivatives encouraged researchers to increase their synthesis as an alternative for the treatment of pathogenic bacterial and fungal infections. In the present study, chalcone derivatives were synthesized through cross aldol condensation reaction between 4-( N , N -dimethylamino)benzaldehyde and multiarm aromatic ketones. The multiarm aromatic ketones were synthesized through nucleophilic substitution reaction between 4-hydroxy acetophenone and benzyl bromides. The benzyl bromides, multiarm aromatic ketones, and corresponding chalcone derivatives were evaluated for their activities against eleven clinical pathogenic Gram-positive, Gram-negative bacteria, and three pathogenic fungi by the disk diffusion method. The minimum inhibitory concentration was determined by the microbroth dilution technique. The results of the present study demonstrated that benzyl bromide derivatives have strong antibacterial and antifungal properties as compared to synthetic chalcone derivatives and ketones. Benzyl bromides (1a and 1c) showed high ester activity against Gram-positive bacteria and fungi but moderate activity against Gram-negative bacteria. Therefore, these compounds may be considered as good antibacterial and antifungal drug discovery. However, substituted ketones (2a-b) as well as chalcone derivatives (3a-c) showed no activity against all the tested strains except for ketone (2c), which showed moderate activity against Candida albicans .

  20. Molecular Targeted Approaches to Cancer Therapy and Prevention Using Chalcones

    Science.gov (United States)

    Jandial, Danielle D.; Blair, Christopher A.; Zhang, Saiyang; Krill, Lauren S.; Zhang, Yan-Bing; Zi, Xiaolin

    2014-01-01

    There is an emerging paradigm shift in oncology that seeks to emphasize molecularly targeted approaches for cancer prevention and therapy. Chalcones (1,3-diphenyl-2-propen-1-ones), naturally-occurring compounds with widespread distribution in spices, tea, beer, fruits and vegetables, consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α, β-unsaturated carbonyl system. Due to their structural diversity, relative ease of chemical manipulation and reaction of α, β-unsaturated carbonyl moiety with cysteine residues in proteins, some lead chalcones from both natural products and synthesis have been identified in a variety of screening assays for modulating important pathways or molecular targets in cancers. These pathways and targets that are affected by chalcones include MDM2/p53, tubulin, proteasome, NF-kappa B, TRIAL/death receptors and mitochondria mediated apoptotic pathways, cell cycle, STAT3, AP-1, NRF2, AR, ER, PPAR-γ and β-catenin/Wnt. Compared to current cancer targeted therapeutic drugs, chalcones have the advantages of being inexpensive, easily available and less toxic; the ease of synthesis of chalcones from substituted benzaldehydes and acetophenones also makes them an attractive drug scaffold. Therefore, this review is focused on molecular targets of chalcones and their potential implications in cancer prevention and therapy. PMID:24467530

  1. Ultrasound accelerated Claisen Schmidt condensation: A green route to chalcones

    Science.gov (United States)

    Calvino, V.; Picallo, M.; López-Peinado, A. J.; Martín-Aranda, R. M.; Durán-Valle, C. J.

    2006-06-01

    Chalcones have been synthesized under sonochemical irradiation by Claisen-Schmidt condensation between benzaldehyde and acetophenone. Two basic activated carbons (Na and Cs-Norit) have been used as catalysts. The effect of the ultrasound activation has been studied. A substantial enhancing effect in the yield was observed when the carbon catalyst was activated under ultrasonic waves. This "green" method (combination of alkaline-doped carbon catalyst and ultrasound waves) has been applied to the synthesis of several chalcones with antibacterial properties achieving, in all cases, excellent activities and selectivities. A comparative study under non-sonic activation has showed that the yields are lower in silent conditions, indicating that the sonication exerts a positive effect on the activity of the catalyst. Cs-doped carbon is presented as the optimum catalyst, giving excellent activity for this type of condensation. Cs-Norit carbon catalyst can compete with the traditional NaOH/EtOH when the reaction is carried out under ultrasounds. The role of solvent in this reaction was studied with ethanol. High conversion was obtained in absence of solvent. The carbons were characterized by thermal analysis, nitrogen adsorption and X-ray photoelectron spectroscopy.

  2. Ultrasound accelerated Claisen-Schmidt condensation: A green route to chalcones

    Energy Technology Data Exchange (ETDEWEB)

    Calvino, V. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Picallo, M. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Lopez-Peinado, A.J. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Martin-Aranda, R.M. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain)]. E-mail: rmartin@ccia.uned.es; Duran-Valle, C.J. [Dpto. de Quimica Inorganica, Facultad de Ciencias, Universidad de Extremadura, Avenida de Elvas s/n., 06071 Badajoz (Spain)

    2006-06-30

    Chalcones have been synthesized under sonochemical irradiation by Claisen-Schmidt condensation between benzaldehyde and acetophenone. Two basic activated carbons (Na and Cs-Norit) have been used as catalysts. The effect of the ultrasound activation has been studied. A substantial enhancing effect in the yield was observed when the carbon catalyst was activated under ultrasonic waves. This 'green' method (combination of alkaline-doped carbon catalyst and ultrasound waves) has been applied to the synthesis of several chalcones with antibacterial properties achieving, in all cases, excellent activities and selectivities. A comparative study under non-sonic activation has showed that the yields are lower in silent conditions, indicating that the sonication exerts a positive effect on the activity of the catalyst. Cs-doped carbon is presented as the optimum catalyst, giving excellent activity for this type of condensation. Cs-Norit carbon catalyst can compete with the traditional NaOH/EtOH when the reaction is carried out under ultrasounds. The role of solvent in this reaction was studied with ethanol. High conversion was obtained in absence of solvent. The carbons were characterized by thermal analysis, nitrogen adsorption and X-ray photoelectron spectroscopy.

  3. Study on the colorimetric properties of 2,4,6-triarylpyridine derivative compound for imaging Formaldehyde

    Science.gov (United States)

    Ovianto, D.; Ma’ruf, F. A. R.; Fadilah, N. N.; Sugiharta, I. B. A. R.; Purwono, B.

    2017-11-01

    The derivative compound of 2,4,6-triarylpyridine was synthesized in two steps. The target compound was tested as colorimetric chemosensor against formaldehyde and the limit of detection was also determined using spectrophotometer UV-vis. The first step of the synthesis was the formation of 4-phenyl-2,6-bis(4-nitrophenyl)pyridine compound (1) from 4-nitroacetophenon and benzaldehyde. The second step of the synthesis was the formation of 4-phenyl-2,6-bis-(4-aminophenyl)pyridine (2) from reduction of the nitro group in compound 1 by HCl 37% solution and Sn metal. Compound 1 and 2 were characterized by spectrometers FTIR, 1H NMR and direct inlet-mass spectrometry. The results showed that compound 1 was synthesized with a yield of 78.3% and compound 2 with a yield of 68.9%. Compound 2 as chemosensor showed color transition from colorless to yellow in chemosensor test against formaldehyde in ethanol solvent. The limit of detection of formaldehyde was measured as 4.7×10-3 M using spectrophotometer UV-vis.

  4. Atmospheric chemistry of benzyl alcohol: kinetics and mechanism of reaction with OH radicals.

    Science.gov (United States)

    Bernard, François; Magneron, Isabelle; Eyglunent, Grégory; Daële, Véronique; Wallington, Timothy J; Hurley, Michael D; Mellouki, Abdelwahid

    2013-04-02

    The atmospheric oxidation of benzyl alcohol has been investigated using smog chambers at ICARE, FORD, and EUPHORE. The rate coefficient for reaction with OH radicals was measured and an upper limit for the reaction with ozone was established; kOH = (2.8 ± 0.4) × 10(-11) at 297 ± 3 K (averaged value including results from Harrison and Wells) and kO(3) < 2 × 10(-19) cm(3) molecule(-1) s(-1) at 299 K. The products of the OH radical initiated oxidation of benzyl alcohol in the presence of NOX were studied. Benzaldehyde, originating from H-abstraction from the -CH(2)OH group, was identified using in situ FTIR spectroscopy, HPLC-UV/FID, and GC-PID and quantified in a yield of (24 ± 5) %. Ring retaining products originating from OH-addition to the aromatic ring such as o-hydroxybenzylalcohol and o-dihydroxybenzene as well as ring-cleavage products such as glyoxal were also identified and quantified with molar yields of (22 ± 2)%, (10 ± 3)%, and (2.7 ± 0.7)%, respectively. Formaldehyde was observed with a molar yield of (27 ± 10)%. The results are discussed with respect to previous studies and the atmospheric oxidation mechanism of benzyl alcohol.

  5. Transition metal-induced activation of alkynes leading to metal carbene species: synthetic application to new {pi}-conjugated molecules

    Energy Technology Data Exchange (ETDEWEB)

    Abo, T; Ohe, K [Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510 (Japan)], E-mail: ohe@scl.kyoto-u.ac.jp

    2008-03-15

    The in situ generation of furylcarbene complexes by means of transition metals was applied to catalytic carbene reactions, such as Wittig-type olefination and cycloisomerization reactions. In the presence of [Rh(OAc){sub 2}]{sub 2} as a catalyst and triphenylphosphine as a carbene accepter, carbonyl-ene-ynes 1a reacted with benzaldehyde to give a 2-styrylfuran derivative 3a. The reaction involving phosphine-ylide formation followed by Wittig-type olefination with aldehydes was applied to synthesis of furfurylidene-containing p-extended conjugated molecules. A Ruthenium catalyst underwent cycloisomerization of 1,2-bis(carbonylenyl)acetylene 10a,b to afford 2,2'-bifuran structures. The crystal structure of 5,5'-diphenyl-2,2'-bifuran 11b was determined by X-ray crystallography. The ORTEP drawings of 11b exhibited transoid and highly planar structure. The emission bands of the bisfuran 11b were observed at 414 and 440 nm, its quantum yield (84%) was higher than that of a similar 5,5'-diphenyl-2,2'-bithiophene.

  6. Reaction of phosphorus ylides with carbonyl compounds in supercritical carbon dioxide

    Energy Technology Data Exchange (ETDEWEB)

    Jeong, Kyung Il; Kim, Hak Do; Shim, Jae Jin; Ra, Choon Sup [Yeungnam Univ., Gyongsan (Korea, Republic of)

    2004-02-15

    The condensation reaction of (benzylene)triphenylphosphoranes with carbonyl compounds in supercritical carbon dioxide was examined. Reactions of (benzylene)phosphoranes (ca. 1 mmol) with several benzaldehydes in a supercritical carbon dioxide (80 .deg. C, 2,000 psi) containing THF entrainer (5%) in a 24 mL reactor proceed smoothly to yield olefination products in fairly good to excellent yields but slower, compared to reactions in a conventional THF solvent. Generally, phosphoranes that are not substituted with a nitro group show more (Z)-selective reactions with aromatic aldehydes under scCO{sub 2} condition than in THF. The reaction of (benzylene)triphenylphosphosphoranes with 4-t-butylcyclohexanone gave the corresponding olefin compounds with a low conversion under both the supercritical carbon dioxide and the organic THF solvent. Our preliminary study showed the Wittig reaction carries out smoothly in supercritical carbon dioxide medium and also a possible tunability of this reaction pathway by adding a entrainer. The results would be useful for devising a novel process for the environmentally friendly Wittig reaction.

  7. Antioxidant and lipase inhibitory activities and essential oil composition of pomegranate peel extracts.

    Science.gov (United States)

    Hadrich, Fatma; Cher, Slim; Gargouri, Youssef Talel; Adel, Sayari

    2014-01-01

    The chemical composition of essential oil, antioxidant and pancreatic lipase inhibitory activities of various solvent extracts obtained from pomegranate peelTunisian cultivar was evaluated. Gas chromatography/mass spectrometry was used to determine the composition of the PP essential oil. Nine-teen components were identified and the main compounds were the camphor (60.32%) and the benzaldehyde (20.98%). The phenolic and flavonoids content varied from 0 to 290.10 mg Gallic acid equivalent and from 5.2 to 20.43 mg catechin equivalent/g dried extract. The antioxidant activity of various solvent extracts from pomegranate peel was also investigated using various in vitro assays as the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical method, β-carotene bleaching and reducing power assays.Methanol and ethanol extracts showed the most potent antioxidant activity in all assays tested followed by water and acetone extracts. The inhibitory effect of the pomegranate peelextracts on porcine pancreatic lipase was evaluated and the results showed that ethanol and methanol extracts markedly reduced lipase activity. Generally, the highestlipase activity inhibitory (100%) was observed at a concentration of 1 mg/ml after 30 min of incubation. LC-MS analysis of ethanol extract showed the presence of four components which are cholorogenic acid, mannogalloylhexoside, gallic acid and ellagic acid. Our findings demonstrate that the ethanol extract from pomegranate peel might be a good candidate for furtherinvestigations of new bioactive substances.

  8. Photoinduced interactions of supramolecular ruthenium(II) complexes with plasmid DNA: synthesis and spectroscopic, electrochemical, and DNA photocleavage studies.

    Science.gov (United States)

    Swavey, Shawn; DeBeer, Madeleine; Li, Kaiyu

    2015-04-06

    Two new bridging ligands have been synthesized by combining substituted benzaldehydes with phenanthrolinopyrrole (php), resulting in new polyazine bridging ligands. The ligands have been characterized by (1)H NMR, mass spectroscopy, and elemental analysis. These new ligands display π-π* transitions above 500 nm with modest molar absorptivities. Upon excitation at the ligand-centered charge-transfer transition, weak emission with a maximum wavelength of 612 nm is observed. When coordinated to two ruthenium(II) bis(bipyridyl) groups, the new bimetallic complexes generated give an overall 4+ charge. The electronic transitions of the bimetallic ruthenium(II) complexes display traditional π-π* transitions at 287 nm and metal-to-ligand charge-transfer transitions at 452 nm with molar absorptivities greater than 30000 M(-1) cm(-1). Oxidation of the ruthenium(II) metal centers to ruthenium(III) occurs at potentials above 1.4 V versus the Ag/AgCl reference electrode. Spectroscopic and electrochemical measurements indicate that the ruthenium(II) moieties behave independently. Both complexes are water-soluble and show the ability to photonick plasmid DNA when irradiated with low-energy light above 550 nm. In addition, one of the complexes, [Ru(bpy)2php]2Van(4+), shows the ability to linearize plasmid DNA and gives evidence, by gel electrophoresis, of photoinduced binding to plasmid DNA.

  9. Variation of volatile terpenes in the edible fungi mycelia Flammulina velutipes and communications in fungus-mite interactions.

    Science.gov (United States)

    Li, Hui-Ping; Yang, Wen-Jian; Qu, Shao-Xuan; Pei, Fei; Luo, Xin; Mariga, Alfred Mugambi; Ma, Lin

    2018-01-01

    Many mites rely on fungi for nutrients, and fungi benefit from them with regard to spore dispersal, or nutrient resources. The interactions among mites and fungi are still not clear in most cases. This study analyzed volatile natural products from the liquid and solid cultures of the edible fungi, Flammulina velutipes (Fr.) Sing, and the solid mycelia induced by the storage mite, Tyrophagus putrescentiae Schrank, using HS-SPME-GC-MS/MS. Five new monoterpenes and 30 new sesquiterpenes were isolated from the two cultures of F. velutipes and a newly monoterpene and 14 newly sesquiterpenes found in the solid mycelia induced by the storage mite. Sesquiterpenes were abundant in the mycelial stage of F. velutipe. The mite was attracted by some volatiles from host fungi, dihydrocarveol, cedrol, β-caryophyllene, α-terpilene, β-pinene and benzaldehyde, analyzed by four-arm olfactometer. Some terpenes induced by T. putrescentiae, such as caryophyllene oxide, bicyclogermacrene, and (-)-spathulenol, would have potential biological function. These results suggest that some volatile sesquiterpenes play an important role in enabling the mite to recognize host fungi. Copyright © 2017 Elsevier Ltd. All rights reserved.

  10. Effects of irrigation regimes on fatty acid composition, antioxidant and antifungal properties of volatiles from fruits of Koroneiki cultivar grown under Tunisian conditions.

    Science.gov (United States)

    Brahmi, Faten; Chehab, Hechmi; Flamini, Guido; Dhibi, Madiha; Issaoui, Manel; Mastouri, Maha; Hammami, Mohamed

    2013-11-15

    The olive tree is generally grown under rain-fed conditions. However, since the yield response to irrigation is great, even with low amounts of water, there is increasing interest in irrigated agriculture. The main goal of this study was, therefore, to investigate the effect of irrigation regimes on olive (Olea europaea L., cv. Koroneiki) obtained from an intensively-managed orchard in a semi-arid area with a Mediterranean climate in Tunisia. Different irrigation treatments 50% ETc, 75% ETc and 100% ETc were applied to the olive orchard. Accordingly, the effects of three irrigation regimes on volatile compounds, fatty acid composition and biological activities of Koroneiki cultivar were studied. The total profile of the volatile constituents of all samples revealed the predominance of 3-ethenylpyridine (from 14.9-19.6%), phenylethyl alcool (from 7.8-19.2%) and benzaldehyde (from 9.0 to 13.8%). During watering level treatments studied, the major fatty acids were oleic, palmitic and linoleic. Antioxidant activity of the fresh fruit volatiles cultivated at a watering level of 100% ETc was higher than that obtained under 50 and 75% Etc. The results of antifungal activity showed that the fruits volatiles of the three irrigation treatments had varying degrees of growth inhibition against the microorganisms tested.

  11. The central chirality of the metal atom and configurational relations in asymmetric reactions catalysed by metal complexes

    Energy Technology Data Exchange (ETDEWEB)

    Pavlov, Valerii A [N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (Russian Federation)

    2004-12-31

    The recently published data on the dependence of the configuration of the reaction product on the structure of a catalytic metal complex (or an intermediate determining the asymmetric induction) in asymmetric catalytic reactions of hydrogen-transfer hydrogenation of acetophenone, hydroformylation of styrene, allylic alkylation of 1,3-diphenylprop-2-enyl acetate and alkylation of benzaldehyde with dialkylzinc are systematised. The applicabilities of octant and quadrant projections of the complexes are compared in order to establish the relationships between their structures and the enantioselectivities of the reactions. The known mechanisms of asymmetric induction in these reactions are discussed with regard to the C{sub 1} or C{sub 2} symmetry of the catalytic complex. The reasons for a decrease in the enantioselectivities of hydrogen-transfer hydrogenation, hydroformylation and alkylation by dialkylzinc [in the absence of Ti(OPr{sup i}){sub 4}] when performed with complexes with chiral C{sub 2}-symmetric ligands (as compared with complexes with asymmetric ligands) are considered.

  12. Regiocontrolled, palladium-catalyzed bisfunctionalization of allenyl esters. Multicomponent coupling approaches to highly substituted alpha,beta-unsaturated delta-lactones.

    Science.gov (United States)

    Hopkins, Chad D; Guan, Lisa; Malinakova, Helena C

    2005-08-19

    A palladium-catalyzed regioselective bisfunctionalization of allenyl esters with boronic acids (nucleophiles) and aldehydes (electrophiles) was demonstrated. The three-component coupling afforded alpha,beta-unsaturated delta-lactones under mild conditions and with excellent chemo-, regio-, and diastereoselectivity. Aromatic, heteroaromatic and vinylic boronic acids (R1B(OH)2) reacted with ethyl 2,3-butadienoate and benzaldehyde to afford the corresponding 4-R(1),6-Ph-disubstituted alpha,beta-unsaturated delta-lactones in 62-78% yields. Lactones derived from aromatic, heteroaromatic, and vinylic aldehydes were isolated in 51-58% yields, while aliphatic aldehydes were less reactive. The regiochemistry of bisfunctionalization of allenyl ester homologues remained controlled by the ester substituent, and the reactions afforded cis-4,5,6-trisubstituted alpha,beta-unsaturated delta-lactones and esters of (Z)-syn-3,4,5-trisubstituted-5-hydroxy-2-pentenoic acids in combined 47-65% yields. The superior performance of a pi-allylpalladium(II) dimer catalyst featuring an auxiliary allyl ligand derived from beta-pinene, among diverse palladium(II) catalysts, was demonstrated. A catalytic cycle involving an unsymmetrical bis-pi-allylpalladium complex as the key intermediate was proposed, and the communication highlights the synthetic potential of such intermediates. However, the efficiency of asymmetry transfer remained low (<20%).

  13. Dissecting the role of TRPV1 in detecting multiple trigeminal irritants in three behavioral assays for sensory irritation [v1; ref status: indexed, http://f1000r.es/p8

    Directory of Open Access Journals (Sweden)

    CJ Saunders

    2013-03-01

    Full Text Available Polymodal neurons of the trigeminal nerve innervate the nasal cavity, nasopharynx, oral cavity and cornea. Trigeminal nociceptive fibers express a diverse collection of receptors and are stimulated by a wide variety of chemicals. However, the mechanism of stimulation is known only for relatively few of these compounds. Capsaicin, for example, activates transient receptor potential vanilloid 1 (TRPV1 channels. In the present study, wildtype (C57Bl/6J and TRPV1 knockout mice were tested in three behavioral assays for irritation to determine if TRPV1 is necessary to detect trigeminal irritants in addition to capsaicin. In one assay mice were presented with a chemical via a cotton swab and their response scored on a 5 level scale. In another assay, a modified two bottle preference test, which avoids the confound of mixing irritants with the animal’s drinking water, was used to assess aversion. In the final assay, an air dilution olfactometer was used to administer volatile compounds to mice restrained in a double-chambered plethysmograph where respiratory reflexes were monitored. TRPV1 knockouts showed deficiencies in the detection of benzaldehyde, cyclohexanone and eugenol in at least one assay. However, cyclohexanone was the only substance tested that appears to act solely through TRPV1.

  14. The effects of the fermentation with immobilized yeast and different cherry varieties on the quality of cherry brandy

    Directory of Open Access Journals (Sweden)

    R. Miličević

    2014-01-01

    Full Text Available The aim of this research was to investigate influence of different fermentation processes (by immobilized yeast cells and classical fermentation and different cherry varieties (Maraska, Montmorencys and Kelleris on the chemical and sensorial characteristics of cherry brandies. Cherry brandies were analyzed to determine chemical composition, aroma profile and sensory properties. Cherry brandies produced by immobilized yeast cells had a higher content of aldehydes, but lower content of total acids, total extract, higher alcohols and esters compared to the samples produced by classical fermentation process. Furfural was not detected in cherry distillates produced by immobilized yeast cells, while distillates produced by classical fermentation process had very low content. Cherry brandies produced by classical fermentation process had significantly higher content of benzaldehyde which has great influence on aroma of cherry brandies. Ethyl octanoate which is considered one of the most important contributors to the aroma of alcoholic distillates was found in the highest concentrations in Maraska distillates. The best evaluated sample was brandy produced from Maraska cherry variety fermented by immobilized yeast cells followed by brandy produced also from Maraska cherry variety, but by classical fermentation process.

  15. Characterization of amygdalin-degrading Lactobacillus species.

    Science.gov (United States)

    Menon, R; Munjal, N; Sturino, J M

    2015-02-01

    Cyanogenic glycosides are phytotoxic secondary metabolites produced by some crop plants. The aim of this study was to identify lactic acid bacteria (LAB) capable of catabolizing amygdalin, a model cyanogenic glycoside, for use in the biodetoxification of amygdalin-containing foods and feeds. Amygdalin-catabolizing lactobacilli were characterized using a combination of cultivation-dependent and molecular assays. Lactobacillus paraplantarum and Lactobacillus plantarum grew robustly on amygdalin (Amg(+)), while other LAB species typically failed to catabolize amygdalin (Amg(-)). Interestingly, high concentrations of amygdalin and two of its metabolic derivatives (mandelonitrile and benzaldehyde) inhibited the growth of Lact. plantarum RENO 0093. The differential regulation of genes tentatively involved in cyanohydrin metabolism illustrated that the metabolism of amygdalin- and glucose-grown cultures also differed significantly. Amygdalin fermentation was a relatively uncommon phenotype among the LAB and generally limited to strains from the Lact. plantarum group. Phenotype microarrays (PM) enabled strain-level discrimination between closely related strains within a species and suggested that phenotypic differences might affect niche specialization. Amygdalin-degrading lactobacilli with practical application in the biodetoxification of amygdalin were characterized. These strains show potential for use as starter cultures to improve the safety of foods and feeds. © 2014 The Society for Applied Microbiology.

  16. Tetradentate Schiff base ligands and their complexes: Synthesis, structural characterization, thermal, electrochemical and alkane oxidation

    Science.gov (United States)

    Ceyhan, Gökhan; Köse, Muhammet; McKee, Vickie; Uruş, Serhan; Gölcü, Ayşegül; Tümer, Mehmet

    Three Schiff base ligands (H2L1-H2L3) with N2O2 donor sites were synthesized by condensation of 1,5-diaminonapthalene with benzaldehyde derivatives. A series of Cu(II), Co(II), Ni(II), Mn(II) and Cr(III) complexes were prepared and characterized by spectroscopic and analytical methods. Thermal, electrochemical and alkane oxidation reactions of the ligands and their metal complexes were investigated. Extensive application of 1D (1H, 13C NMR) and 2D (COSY, HETCOR, HMBC and TOSCY) NMR techniques were used to characterize the structures of the ligands and establish the 1H and 13C resonance assignments of the three ligands. Ligands H2L1 and H2L3 were obtained as single crystals from THF solution and characterized by X-ray diffraction. Both molecules are centrosymmetric and asymmetric unit contains one half of the molecule. Catalytic alkane oxidation reactions with the transition metal complexes investigated using cyclohexane and cyclooctane as substrates. The Cu(II) and Cr(III) complexes showed good catalytic activity in the oxidation of cyclohexane and cyclooctane to desired oxidized products. Electrochemical and thermal properties of the compounds were also investigated.

  17. Novel Chiral Bis-Phosphoramides as Organocatalysts for Tetrachlorosilane-Mediated Reactions

    Directory of Open Access Journals (Sweden)

    Sergio Rossi

    2017-12-01

    Full Text Available The formation of novel chiral bidentate phosphoroamides structures able to promote Lewis base-catalyzed Lewis acid-mediated reactions was investigated. Two different classes of phosphoroamides were synthetized: the first class presents a phthalic acid/primary diamine moiety, designed with the aim to perform a self-assembly recognition process through hydrogen bonds; the second one is characterized by the presence of two phosphoroamides as side arms connected to a central pyridine unit, able to chelate SiCl4 in a 2:1 adduct. These species were tested as organocatalysts in the stereoselective allylation of benzaldehyde and a few other aromatic aldehydes with allyl tributyltin in the presence of SiCl4 with good results. NMR studies confirm that only pyridine-based phosphoroamides effectively coordinate tetrachlorosilane and may lead to the generation of a self-assembled entity that would act as a promoter of the reaction. Although further work is necessary to clarify and confirm the formation of the hypothesized adduct, the study lays the foundation for the design and the synthesis of chiral supramolecular organocatalysts.

  18. Structural and catalytic properties of some azo-rhodanine Ruthenium(III) complexes

    Science.gov (United States)

    Shoair, A. F.; El-Bindary, A. A.; Abd El-Kader, M. K.

    2017-09-01

    Novel azo-rhodanine ruthenium(III) complexes of the type trans-[Ru(Ln)2(AsPh3)2]Cl (Ln = monobasic bidentate anions of 5-(4‧-methoxyphenylazo)-3-phenylamino-2-thioxothiazolidin-4-one (HL1), 5-(phenylazo)-3-phenylamino-2-thioxothiazolidin-4-one (HL2) and 5-(4‧-chlorophenylazo)-3-phenylamino-2-thioxothiazolidin-4-one (HL3); AsPh3 = triphenylarsine) have been synthesized and characterized by elemental analysis, spectroscopic (IR, 1H NMR and UV-VIS), magnetic, X-ray diffraction, mass spectra and thermal analysis techniques. These techniques confirm the formation of octahedral ruthenium(III) complexes. The Ru(III) complexes were tested as a catalysts for the oxidation of benzyl alcohol to benzaldehyde with N-methylmorpholine-N-oxide as a co-oxidant. The effect of time, temperature, and solvent were also studied and the mechanism of this catalytic oxidation reaction is suggested. Molecular docking was used to predict the binding between azo rhodanine derivatives (HLn) with the receptor of 3qum- immune system receptor of human prostate specific antigen (PSA) in a Fab sandwich with a high affinity and a PCa selective antibody.

  19. PERUBAHAN KOMPONEN VOLATIL SELAMA FERMENTASI KECAP [Change Volatile Components During Soy Sauce Fermentation

    Directory of Open Access Journals (Sweden)

    Anton Apriyantono1

    2004-08-01

    Full Text Available A study has been conducted to investigate changes of volatile components during soy sauce fermentation. During the fermentation, many volatile components produced may contribute to soy sauce flavor. THe volatile identified by GC-MS werw classified into hydrocarbon (15, alcohol (15, aldehyde (14, ester (14, ketone (9, benzene derivative (11, fatty acid (9, furan (5, terpenoid (18, pyrazine (3, thiazole (1, pyridine (1 and sulfur containing compound (2.Concentration of compounds found in almost all fermentation steps, such as hexanal and benzaldehyde did. These compounds may be derived from raw soybean, since they were all present in raw soybean and their concentration did not change during fermentation. Concentration of palmitic acid and benzeneacetaldehyde, in general, increased during all fermentation steps. They are probably derived from lipid degradation or microorganism activities. Concentrations of some fatty acids, esters and hydrocarbons, such as linoleic acid, methyl palmitate and heptadecane increased during salt fermentation only. Concentration of some other compounds, such as 2,4 decadienal decreased or undetected during fermentation.The absence of some volatile compounds, e.g. (E-nerolidol and (E,E-famesol in boiled soybean which were previously present in raw soybean may be due to evaporation of these compounds during boiling. Some volatile compounds such as, methyl heptadecanoate and few aromatic alcohols are likely derived from Aspergillus sojae, since these compounds were identified only in 0 day koji

  20. SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE

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    Muhammad Idham Darussalam Mardjan

    2012-02-01

    Full Text Available Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.