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Odor coding in the antenna of the tsetse fly Glossina morsitans

Tsetse flies transmit trypanosomiasis to humans and livestock across much of sub-Saharan Africa. Tsetse are attracted by olfactory cues emanating from their hosts. However, remarkably little is known about the cellular basis of olfaction in tsetse. We have carried out a systematic physiological analysis of the Glossina morsitans antenna. We identify 7 functional classes of olfactory sensilla that respond to human or animal odorants, CO2, sex and alarm pheromones, or other odorants known to attract or repel tsetse. Sensilla differ in their response spectra, show both excitatory and inhibitory responses, and exhibit different response dynamics to different odor stimuli. We find striking differences between the functional organization of the tsetse fly antenna and that of the fruit fly Drosophila melanogaster. One morphological type of sensilla has a different function in the 2 species: Trichoid sensilla respond to pheromones in Drosophila but respond to a wide diversity of compounds in G. morsitans. In contrast to Drosophila, all tested G. morsitans sensilla that show excitatory responses are excited by one odorant, 1-octen-3-ol, which is contained in host emanations. The response profiles of some classes of sensilla are distinct but strongly correlated, unlike the organization described in the Drosophila antenna. Taken together, this study defines elements that likely mediate the attraction of tsetse to its hosts and that might be manipulated as a means of controlling the fly and the diseases it transmits.

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NOVEL ALKANOIC ACID DERIVATIVE AND PERFUME COMPOSITION COMPRISING THE COMPOUND

PROBLEM TO BE SOLVED: To provide a novel alkanoic acid derivative that can impart characteristic fragrances and flavors to perfumery, food and drink and the like, and a perfume composition comprising the compound as an active ingredient. SOLUTION: This invention relates to 5-[(1-alkoxy)ethoxy]alkanoic acid alkyl represented by the formula (1); where R1 is methyl or ethyl group, R2 is 3-7C alkyl group, and R3 is ethyl, propyl or butyl group. This invention also relates to a perfume composition comprising 5-[(1-alkoxy)ethoxy]alkanoic acid alkyl represented by the formula (1) as an active ingredient. COPYRIGHT: (C)2015,JPO&INPIT

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Tetrahydropyran – Wikipedia,
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New strategies in carbonylation chemistry: The synthesis of delta-lactones from saturated alcohols and CO

This paper describes the delta-carbonylation of saturated alcohols which uses a 1,5-hydrogen-transfer reaction of alkoxyl radicals and subsequent carbonylation at the delta-carbon atoms as the key. The carbonylation reactions of five classes of saturated alcohols, namely, primary alcohols having primary delta-carbons, primary alcohols having secondary delta-carbons, primary alcohols having tertiary delta-carbons, secondary alcohols having primary delta- carbons, secondary alcohols having secondary delta-carbons, were carded out, in which lead tetraacetate (LTA) was used as a one-electron oxidant to generate the alkoxyl radicals. Carbonylation of these saturated alcohols, except for primary alcohols having tertiary delta-carbons, took place to afford delta-lactones in moderate to good yields. The mechanism of the remote carbonylation likely involves (1) alkoxyl radical generation via LTA oxidation of a saturated alcohol, (2) conversion of this alkoxyl radical to a delta-hydroxyalkyl radical by a 1,5-hydrogen-transfer reaction, (3) CO trapping of the delta-hydroxyalkyl radical yielding an acyl radical, and (4) oxidation and cyclization of the acyl radical to give a delta-lactone. A metal salt-free system was also tested for a substrate derived from a tertiary alcohol having a secondary delta- carbon; the photolysis of an alkyl 4-nitrobenzenesulfenate under CO pressures gave a delta-lactone in moderate yield.

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Tetrahydropyran – Wikipedia,
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Extracurricular laboratory:new discovery of 6-Butyltetrahydro-2H-pyran-2-one

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High Pressure Carbon Dioxide pasteurization of coconut water: A sport drink with high nutritional and sensory quality

High Pressure Carbon Dioxide (HPCD) treatment was applied to the pasteurization of coconut water in order to guarantee both its microbial stability and preserve its nutritional and sensory attributes. It was demonstrated that 120 bar, 40 C, 30 min were the optimal process conditions to induce a 5 Log(CFU/ml) reduction of mesophilic microorganisms, lactic acid bacteria, yeasts and molds and a 7 Log reduction of the total coliforms. The effect of HPCD on the quality traits of coconut water were investigated by means of physical-chemical and sensory analyses and compared to the Heat Pasteurized (HP, 90 C, 1 min) and Fresh Untreated (FU) product. No differences in the basic chemical composition, vitamins and amino acids, were detected between HPCD and FU products. However, differences in the volatile compounds present in the three products were clearly distinguishable; HPCD resulted in a reduction of most of the volatile fractions while HP induced the formation of compounds with a toasted and malty aroma. Nevertheless, few sensory differences were perceived between the FU and the HPCD coconut water, and both were clearly differentiated from the HP product.

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Tetrahydropyran – Wikipedia,
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Characterization of Key Odorants Causing a Fusty/Musty Off-Flavor in Native Cold-Pressed Rapeseed Oil by Means of the Sensomics Approach

The sensomics approach was used to clarify the formation of the fusty/musty off-flavor of native cold-pressed rapeseed oil. A “positive control” (PC) showing the desired sensory attributes and an oil eliciting a fusty/musty off-flavor (OF) were analyzed. Comparative aroma extract dilution analysis (cAEDA), identification experiments, quantitation by stable isotope dilution assays (SIDAs), calculation of odor activity values (OAVs), and aroma recombination resulted in 11 odorants with an OAV ? 1 in PC. Main differences between both oils were obtained for compounds caused by microbial influence revealing significantly higher concentrations in OF, e.g., for ethyl 2-methylbutanoate, 2-methoxyphenol, 3-hydroxy-4,5-dimethylfuran-2(5H)-one (sotolon), 2- and 3-methylbutanoic acid, and 4-methylphenol. Comparison of the key odorants in OF with those of the rapeseeds (OFS), from which it was pressed, showed the same 18 compounds proving that the grade of the seeds and their storage conditions are important criteria for the quality of the final oil. Finally, a further 7 native cold-pressed rapeseed oils, eliciting the same sensory defect, were analyzed to confirm aroma-active marker compounds responsible for the fusty/musty off-flavor.

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Tetrahydropyran – Wikipedia,
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Process for making perfume containing surfactant compositions having perfume burst and enhanced perfume deposition when diluted

The present invention relates to a process for preparing or selecting compositions having a fragrance burst of at least 20% relative to a product before dilution as well as enhanced deposition. The composition is selected such that perfume and surfactant in said composition yields a calculated ?Perfume Burst Index? (PBI) value of less than 3 as per algorithm defining the PBI.

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Tetrahydropyran – Wikipedia,
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Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C1-C10

A compendium of phase change enthalpies published in 2010 is updated to include the period 1880-2015. Phase change enthalpies including fusion, vaporization, and sublimation enthalpies are included for organic, organometallic, and a few inorganic compounds. Part 1 of this compendium includes organic compounds from C1-C10. Part 2 of this compendium, to be published separately, will include organic and organometallic compounds from C11 to C192. Sufficient data are presently available to permit thermodynamic cycles to be constructed as an independent means of evaluating the reliability of the data. Temperature adjustments of phase change enthalpies from the temperature of measurement to the standard reference temperature, T = 298.15 K, and a protocol for doing so are briefly discussed.

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Tetrahydropyran – Wikipedia,
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Effects of fatty acids bound to monoglycerides in water-in-oil type emulsions on the release of aroma compounds

To elucidate the mechanism of flavor release from water-in-oil (W/O) emulsions containing a semi-solid fat, we analyzed the release of aroma components using a model emulsion with 57 volatiles. This methodology utilized headspace solid-phase microextraction-gas chromatography/mass spectrometry and evaluation of water droplet distribution, solid fat contents, and interface elastic modulus. The ratio of release of unsaturated aldehydes and esters from an unsaturated monoglyceride emulsion to that from a saturated monoglyceride emulsion increased with the increasing value of LogPow. For volatile fatty acids, the rate was relatively lower and did not depend on the value of LogPow. Furthermore, the release of lactones from the unsaturated monoglyceride emulsion was greater than that from the saturated monoglyceride emulsion. We conclude that lactone release was influenced by the interaction of carbon chains between lactones and the monoglyceride emulsions. Additionally, the carbon chain of saturated fatty acids on the interface inhibited volatile fatty acid access to the interface as a result of steric hindrance. Finally, the release of alcohols and esters was assumed to be affected by a combination of these effects.

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Changes in the Key Aroma Compounds of Raw Shiitake Mushrooms (Lentinula edodes) Induced by Pan-Frying As Well As by Rehydration of Dry Mushrooms

Application of the aroma extract dilution analysis (AEDA) on an extract/distillate from raw shiitake mushrooms revealed 32 odorants among which 3-(methylthio)propanal (cooked potato), 1-octen-3-one, and 1-octen-3-ol (both mushroom-like) showed the highest flavor dilution (FD) factors. An isotope enrichment experiment with raw shiitake tissue and either 13C18-linoleic acid or 2H4-1-octen-3-ol confirmed that both 1-octen-3-ol and 1-octen-3-one are direct degradation products of the fatty acid, but it could be proven for the first time that the ketone is not formed by an oxidation of the alcohol. After pan-frying, 42 odor-active compounds appeared among which 3-hydroxy-4,5-dimethylfuran-2(5H)-one (savory), 1,2,4,5-tetrathiane (burnt, sulfury), 4-hydroxy-2,5-dimethylfuran-3(2H)-one (caramel-like), phenylacetic acid (honey-like), 3-(methylthio)-propanal, and trans-4,5-epoxy-(E)-2-decenal (metallic) showed the highest FD factors. To get a deeper insight into their aroma contribution, 19 key odorants were quantitated in the raw shiitake and twenty-one in the pan-fried mushrooms by stable isotope dilution assays, and new methods for the quantitation of four sulfur compounds were developed. A calculation of odor activity values (OAV; ratio of concentration to odor threshold) showed that 1-octen-3-one was by far the most important odorant in raw shiitake. During pan-frying, in particular, four aroma compounds were significantly increased, i.e., 4-hydroxy-2,5-dimethylfuran-3(2H)-one, dimethyl trisulfide, 1,2,4,5-tetrathiane, and 1,2,3,5,6-pentathiepane. The overall aroma profile of pan-fried shiitake could very well be mimicked by an aroma recombinate consisting of 15 reference aroma compounds in the concentrations determined in the pan-fried mushrooms. Further results showed that the sulfur compounds were even higher in rehydrated dry shiitake as compared to the pan-fried mushrooms.

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Tetrahydropyran – Wikipedia,
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Potent Odorants of Characteristic Floral/Sweet Odor in Chinese Chrysanthemum Flower Tea Infusion

An investigation using the aroma extract dilution analysis (AEDA) technique applied to the aroma concentrates prepared from the tea infusions of two different types of Chinese chrysanthemum flowers (flower buds, blooming flowers) revealed that 29 aroma peaks were detected in the aroma concentrates, and 17 compounds were newly identified or tentatively identified in the chrysanthemum flower tea. AEDA also revealed that the aroma peaks having high flavor dilution factors mainly consisted of a floral/sweet note in addition to metallic and phenol-like/spicy notes. Among them, four aroma peaks having a floral/sweet were identified as verbenone, ethyl 3-phenylpropanoate, propyl 3-phenylpropanoate, and ethyl cinnamate, and a semiquantitative analysis revealed that the flower buds were rich in these compounds. Furthermore, a chiral analysis revealed that (-)-verbenone existed in both flowers at a 3 times higher concentration than (+)-verbenone. Additionally, because the detection threshold of (-)-verbenone was lower than that of the (+)-verbenone, it is concluded that the (-)-isomer was a main contributor of the aroma peak of verbenone in the chrysanthemum flower tea.

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