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Solid acid catalysis of tandem isomerization-lactonization of olefinic acids

The conversion of unsaturated acids to gamma-lactones is catalyzed by the solid sulfonic acid catalysts Amberlyst-15 and Nafion SAC-13 in refluxing chlorobenzene. For 3- and 4-enoic acids, in which double bond migration is not required for gamma-lactone formation, yields are 95-100%. For 5-, 6-, 9-, and 10-enoic acids, the lactone yield decreases from 95% to 25% as the distance between the olefin and carboxylic acid groups increases. Amberlyst-15 is the preferred catalyst in these reactions because of its lower cost and reusability.

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Screening of key odorants and anthocyanin compounds of cv. Okuzgozu (Vitis vinifera L.) red wines with a free run and pressed pomace using GC-MS-Olfactometry and LC-MS-MS

The principal purpose of the present work is to characterize the aroma, aroma-active, and anthocyanin profiles of Okuzgozu wines and to observe the effect of the pomace pressing technique on these parameters. A total of 58 and 59 volatile compounds were identified and quantified in free-run juice wine (FRW) and pressed pomace wine (PW). Alcohols were found as the most dominant group among aroma compounds followed by esters and acids. However, among all these compounds, only 11 and 13 of them could be considered as key odorants in aromatic extracts of FRW and PW, respectively. According to GC-MS-O analysis, ethyl octanoate (fruity), phenyl ethyl acetate (fruity), and 2-phenyl ethanol (flowery) were found as the main contributors to the overall scent of both wines. Beyond the aroma profiles, anthocyanin contents of both types of wines were also investigated, and total 14 and 15 anthocyanins were identified and quantified in FRW and PW. Malvidin-3-glycoside and its acetyl and coumaroyl forms were identified as the dominant anthocyanins in both wines. It is worth noting the pressing application (2.0 atm) led to an increase of some unpleasant notes in the aroma providing chemical, pharmacy, and fermented aromas in wine. On the other hand, the wines produced with pressed pomace presented higher amounts of anthocyanins.

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Optimization and validation of a DHS-TD-GC-MS method to wineomics studies

A dynamic headspace sorptive extraction (DHS) combined with thermal desorption (TD) and coupled with gas chromatography-mass spectrometry (GC/MS) was developed for the determination of forty-four volatile aroma metabolites (VAMs) which describe aroma fingerprints of wines. The response surface methodology (RSM) and a central composite design (CCD) was used to obtain the optimal values for the experimental extraction variables, and the results were assessed by an analysis of variance (ANOVA) and a principal component analysis (PCA). The VAMs exhibited optimal extraction with the high levels of salt concentration (1.5 g NaCl) and using an extraction temperature of 40 C during 10 min, and a subsequent purge volume of 300 mL. Subsequently, the calibration curves were created for the quantification of each VAMs with seven levels of concentration obtaining a correlation coefficients (R2) above 0.9900 for all of them. The proposed method was successfully validated and showed good precision and accuracy values for all VAMs. Lastly, the method was applied to quantify VAMs, responsible for the aroma fingerprints of white and red wines, from different Denomination of Origin

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COMPOSITIONS AND METHODS FOR THE ATTRACTION AND REPULSION OF INSECTS

The present invention provides insect attractants and repellents as well as methods of trapping and/or altering the behavioral patterns of vector pests such as mosquitoes and other hematophagous pests.

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Identification of volatile organic compounds in human cerumen

We report here the initial examination of volatile organic compounds (VOCs) emanating from human earwax (cerumen). Recent studies link a single nucleotide polymorphism (SNP) in the adenosine triphosphate (ATP) binding cassette, sub-family C, member 11 gene (ABCC11) to the production of different types of axillary odorants and cerumen. ABCC11 encodes an ATP-driven efflux pump protein that plays an important function in ceruminous apocrine glands of the auditory canal and the secretion of axillary odor precursors. The type of cerumen and underarm odor produced by East Asians differ markedly from that produced by non-Asians. In this initial report we find that both groups emit many of the same VOCs but differ significantly in the amounts produced. The principal odorants are volatile organic C2-to-C6 acids. The physical appearance of cerumen from the two groups also matches previously reported ethnic differences, viz., cerumen from East Asians appears dry and white while that from non-Asians is typically wet and yellowish-brown.

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Development of a sensitive non-targeted method for characterizing the wine volatile profile using headspace solid-phase microextraction comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry

Future understanding of differences in the composition and sensory attributes of wines require improved analytical methods which allow the monitoring of a large number of volatiles including those present at low concentrations. This study presents the optimization and application of a headspace solid-phase microextraction (HS-SPME) method for analysis of wine volatiles by comprehensive two-dimensional gas chromatography (GC ¡Á GC) time-of-flight mass spectrometry (TOFMS). This study demonstrates an important advancement in wine volatile analysis as the method allows for the simultaneous analysis of a significantly larger number of compounds found in the wine headspace compared to other current single dimensional GC-MS methodologies. The methodology allowed for the simultaneous analysis of over 350 different tentatively identified volatile and semi-volatile compounds found in the wine headspace. These included potent aroma compound classes such as monoterpenes, norisoprenoids, sesquiterpenes, and alkyl-methoxypyrazines which have been documented to contribute to wine aroma. It is intended that wine aroma research and wine sensory research will utilize this non-targeted method to assess compositional differences in the wine volatile profile.

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TERTIARY HYDROXYL FUNCTIONAL ALKOXYSILANES AND METHODS FOR PREPARING THEREOF

This invention relates to a tertiary hydroxyl functional alkoxysilane of the general formula (I), wherein R1 is selected from the group consisting of hydrogen and a linear or branched, substituted or unsubstituted hydrocarbon residue having 1 to 20 carbon atoms; R2 and R3 are same or different and are, independent from one another, selected from a linear or branched, substituted or unsubstituted hydrocarbon residue having 1 to 20 carbon atoms; R4 is selected from a linear or branched, substituted or unsubstituted hydrocarbon residue having 1 to 20 carbon atoms; R5 is selected from a linear or branched, substituted or unsubstituted hydrocarbon residue having 1 to 20 carbon atoms; R6 and R7 are same or different and are, independent from one another, selected from a linear or branched, substituted or unsubstituted hydrocarbon residue having 1 to 20 carbon atoms; and n is 1, 2 or 3, a method for preparing thereof, and the use of the tertiary hydroxyl functional alkoxysilane of the general formula (I).

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Interactions of inhibitor molecules with the human CYP2E1 enzyme active site

CYP2E1 is an important enzyme oxidizing ethanol as well as several drugs and other xenobiotics in the human liver. We determined the inhibition potency of structurally diverse compounds against human CYP2E1, and analyzed their interactions with the enzyme active site by molecular docking and 3D-QSAR approaches. The IC50 values for the tested compounds varied from 1.4 muM for gamma-undecanolactone to over 46 mM for glycerol. This data set was used to create a comparative molecular field analysis (CoMFA) model. The most important interactions for binding of inhibitors were identified by docking and key features for inhibitors were characterized via the COMFA model. Since the active site of CYP2E1 is flexible, long chain lactones and alkyl alcohols fitted best into the larger open form while the other compounds fitted better in the smaller closed form of the active site. Electrostatic interactions near the Thr303 residue proved to be important for inhibition of the enzyme activity. Thus, docking analysis and the predictive CoMFA model proved to be efficient tools for revealing interactions between inhibiting compounds and CYP2E1. These approaches can be used to analyze CYP2E1-mediated metabolism and drug interactions in the development of new chemical entities.

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Volatile composition and odour-activity value of thornless ‘Black Diamond’ and ‘Marion’ blackberries

Black Diamond’ is a recently developed thornless blackberry cultivar with large fruit size, high yield, and good processed fruit quality that has rapidly become an industry standard. The flavour of ‘Black Diamond’ fruit is not the same as ‘Marion’, which is regarded by the industry as having the ideal flavour. In order to understand the aroma differences, the volatile composition of ‘Marion’ and ‘Black Diamond’ was analysed using stir bar sorptive extraction-gas chromatography-mass spectrometry (SBSE-GC-MS) and solid-phase extraction (SPE)-microvial insert thermal desorption-GC-MS for two growing seasons. Although seasonal variations were present, the overall volatile profile in ‘Marion’ and ‘Black Diamond’ were very similar, but the concentrations of some aroma compounds varied greatly. Odour-activity value (OAV) indicated that furaneol, linalool, beta-ionone, and hexanal could be most important in ‘Marion’, while in ‘Black Diamond’, the most important compounds were linalool, beta-ionone, furaneol, and 2-heptanol. The major difference between the cultivars for aroma compounds was that ‘Marion’ had a 5 times higher OAV of furaneol than ‘Black Diamond’, while ‘Black Diamond’ had a 3 times higher OAV of linalool than ‘Marion’. The chemical analysis results matched with the descriptive sensory evaluation that ‘Marion’ had more berry, fruity, strawberry aroma while ‘Black Diamond’ had more floral aroma.

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Characterization of Key Aroma Compounds in a Commercial Rum and an Australian Red Wine by Means of a New Sensomics-Based Expert System (SEBES) – An Approach to Use Artificial Intelligence in Determining Food Odor Codes

Although to date more than 10 000 volatile compounds have been characterized in foods, a literature survey has previously shown that only 226 aroma compounds, assigned as key food odorants (KFOs), have been identified to actively contribute to the overall aromas of about 200 foods, such as beverages, meat products, cheeses, or baked goods. Currently, a multistep analytical procedure involving the human olfactory system, assigned as Sensomics, represents a reference approach to identify and quantitate key odorants, as well as to define their sensory impact in the overall food aroma profile by so-called aroma recombinates. Despite its proven effectiveness, the Sensomics approach is time-consuming because repeated sensory analyses, for example, by GC/olfactometry, are essential to assess the odor quality and potency of each single constituent in a given food distillate. Therefore, the aim of the present study was to develop a fast, but Sensomics-based expert system (SEBES) that is able to reliably predict the key aroma compounds of a given food in a limited number of runs without using the human olfactory system. First, a successful method for the quantitation of nearly 100 (out of the 226 known KFOs) components was developed in combination with a software allowing the direct use of the identification and quantitation data for the calculation of odor activity values (OAV; ratio of concentration to odor threshold). Using a rum and a wine as examples, the quantitative results obtained by the new SEBES method were compared to data obtained by applying an aroma extract dilution analysis and stable isotope dilution assays required in the classical Sensomics approach. A good agreement of the results was found with differences below 20% for most of the compounds considered. By implementing the GC ¡Á GC data analysis software with the in-house odor threshold database, odor activity values (ratio of concentration to odor threshold) were directly displayed in the software pane. The OAVs calculated by the software were in very good agreement with data manually calculated on the basis of the data obtained by SIDA. Thus, it was successfully shown that it is possible to characterize key food odorants with one single analytical platform and without using the human olfactory system, that is, by “artificial intelligence smelling”.

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