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Journal articles on the topic 'Alkylpyrazines'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Masuda, Hideki, and Satoru Mihara. "Olfactive properties of alkylpyrazines and 3-substituted 2-alkylpyrazines." Journal of Agricultural and Food Chemistry 36, no. 3 (1988): 584–87. http://dx.doi.org/10.1021/jf00081a044.

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2

Buechi, George, and Jose Galindo. "Regioselective synthesis of alkylpyrazines." Journal of Organic Chemistry 56, no. 8 (1991): 2605–6. http://dx.doi.org/10.1021/jo00008a002.

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3

Guram, Anil S., and Richard F. Jordan. "Zirconium-mediated reactions of alkylpyrazines and alkynes. Synthesis of highly substituted alkylpyrazines." Journal of Organic Chemistry 57, no. 22 (1992): 5994–99. http://dx.doi.org/10.1021/jo00048a038.

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4

Fors, Susan M., and Bertil K. Olofsson. "Alkylpyrazines, volatiles formed in the Maillard reaction. II. Sensory properties of five alkylpyrazines." Chemical Senses 11, no. 1 (1986): 65–77. http://dx.doi.org/10.1093/chemse/11.1.65.

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5

GURAM, A. S., and R. F. JORDAN. "ChemInform Abstract: Zirconium-Mediated Reactions of Alkylpyrazines and Alkynes. Synthesis of Highly Substituted Alkylpyrazines." ChemInform 24, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199309186.

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6

Kang, Do Won, Hong Lae Kim, and Chan Ho Kwon. "Conformational preference and cationic structure of 2-methylpyrazine by VUV-MATI spectroscopy and natural bond orbital analysis." Physical Chemistry Chemical Physics 21, no. 18 (2019): 9255–64. http://dx.doi.org/10.1039/c9cp00766k.

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Alkylpyrazines, which are well-known as aromatic substances and traditional medicines, are interesting molecular systems, and their methyl conformations result in unique structural and dynamical properties.

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7

BUECHI, G., and J. GALINDO. "ChemInform Abstract: Regioselective Synthesis of Alkylpyrazines." ChemInform 22, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199139178.

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8

Sakoguchi, Akihiro, Ryuichi Ueoka, Yasuo Kato, and Yasuhiko Arai. "Vapor Pressures of Alkylpyridines and Alkylpyrazines." KAGAKU KOGAKU RONBUNSHU 21, no. 1 (1995): 219–23. http://dx.doi.org/10.1252/kakoronbunshu.21.219.

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9

Wagner, R., M. Czerny, J. Bielohradsky, and W. Grosch. "Structure-odour-activity relationships of alkylpyrazines." Zeitschrift f�r Lebensmitteluntersuchung und -Forschung A 208, no. 5-6 (1999): 308–16. http://dx.doi.org/10.1007/s002170050422.

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10

Amrani-Hemaimi, Miriam, Christoph Cerny, and Laurent B. Fay. "Mechanisms of Formation of Alkylpyrazines in the Maillard Reaction." Journal of Agricultural and Food Chemistry 43, no. 11 (1995): 2818–22. http://dx.doi.org/10.1021/jf00059a009.

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11

Mukherjee, Ashis, Sandhya A. M. Duggan, and William C. Agosta. "Intramolecular photochemical hydrogen abstraction in 2-alkylpyrazines and 2-alkylpyridines." Journal of Organic Chemistry 59, no. 1 (1994): 178–81. http://dx.doi.org/10.1021/jo00080a029.

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12

Xu, Sihang, Ramu Errabelli, Donald H. Feener, Katherine Noble, and Athula B. Attygalle. "Identification of alkylpyrazines by gas chromatography mass spectrometry (GC-MS)." Journal of Chromatography A 1589 (March 2019): 149–61. http://dx.doi.org/10.1016/j.chroma.2019.01.011.

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13

Yogo, Kentaro, Noel S. Quiming, Yoshihiro Saito, and Kiyokatsu Jinno. "Prediction of Chromatographic Retention of Pyrazine and Alkylpyrazines in RP-LC." Chromatographia 70, no. 5-6 (2009): 677–84. http://dx.doi.org/10.1365/s10337-009-1243-4.

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14

YOGO, Kentaro, Chiharu TAKEMURA, Yoshihiro SAITO, and Kiyokatsu JINNO. "An Abnormal Temperature Dependence of Alkylpyrazines’ Retention in Reversed-Phase Liquid Chromatography." Analytical Sciences 27, no. 12 (2011): 1257. http://dx.doi.org/10.2116/analsci.27.1257.

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15

Brunetto, María del Rosario, Yelitza Delgado Cayama, Lubin Gutiérrez, et al. "Headspace gas chromatography–mass spectrometry determination of alkylpyrazines in cocoa liquor samples." Food Chemistry 112, no. 1 (2009): 253–57. http://dx.doi.org/10.1016/j.foodchem.2008.05.082.

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16

Akochi-K, E., I. Alli, S. Kermasha, V. Yaylayan, and J. Dumont. "Quantitation of alkylpyrazines in maple syrup, maple flavors and non-maple syrups." Food Research International 27, no. 5 (1994): 451–57. http://dx.doi.org/10.1016/0963-9969(94)90239-9.

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17

Joo, Kwangjee, and Chi-Tang Ho. "Quantitative Analysis of Alkylpyrazines in Regular- and Low-fat Commercial Peanut Butter Preparations." Bioscience, Biotechnology, and Biochemistry 61, no. 1 (1997): 171–73. http://dx.doi.org/10.1271/bbb.61.171.

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18

Lund, Eric D. "Determination of 2-Methoxy-3-alkylpyrazines in Carrot Products by Gas Chromatography/Nitrogen–Phosphorus Detection." Journal of AOAC INTERNATIONAL 77, no. 2 (1994): 416–20. http://dx.doi.org/10.1093/jaoac/77.2.416.

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Abstract The 2-methoxy-3-alkylpyrazines in 6 types of carrot products were determined by a stripping–selective trapping procedure followed by purge-and-trap gas chromatographic analysis with an NP detector. The aroma threshold of one of the principal pyrazines, 2-methoxy-3-sec-butylpyrazine, in a carrot medium was 0.19 ng/g. The concentrations of this compound in whole-carrot products were 0.43 (fresh), 0.291 (canned, cooked), and 0.224 ng/g (frozen). A diced, cooked, and freeze-dried product contained 0.070 ng/g. All of these products contained only this pyrazine. In contrast, a shredded, bag

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19

Kremer, Jonathan I., Stephanie Pickard, Lara F. Stadlmair, et al. "Alkylpyrazines from Coffee are Extensively Metabolized to Pyrazine Carboxylic Acids in the Human Body." Molecular Nutrition & Food Research 63, no. 14 (2019): 1801341. http://dx.doi.org/10.1002/mnfr.201801341.

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20

Laska, Matthias, Oskar Persson, and Laura Teresa Hernandez Salazar. "Olfactory sensitivity for alkylpyrazines-a comparative study in CD-1 mice and spider monkeys." Journal of Experimental Zoology Part A: Ecological Genetics and Physiology 311A, no. 4 (2009): 278–88. http://dx.doi.org/10.1002/jez.527.

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21

Fang, Mingchih, and Keith R. Cadwallader. "Convenient Synthesis of Stable Deuterium-Labeled Alkylpyrazines for Use in Stable Isotope Dilution Assays." Journal of Agricultural and Food Chemistry 61, no. 15 (2013): 3580–88. http://dx.doi.org/10.1021/jf4001204.

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22

Showalter, D. N., E. J. Troyer, M. Aklu, E. B. Jang, and M. S. Siderhurst. "Alkylpyrazines: alarm pheromone components of the little fire ant, Wasmannia auropunctata (Roger) (Hymenoptera, Formicidae)." Insectes Sociaux 57, no. 2 (2010): 223–32. http://dx.doi.org/10.1007/s00040-010-0075-4.

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23

Serra Bonvehí, J., and F. Ventura Coll. "Factors Affecting the Formation of Alkylpyrazines during Roasting Treatment in Natural and Alkalinized Cocoa Powder." Journal of Agricultural and Food Chemistry 50, no. 13 (2002): 3743–50. http://dx.doi.org/10.1021/jf011597k.

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24

Anand, R., T. M. Jyothi, and B. S. Rao. "A comparative study on the catalytic activity of ZnO modified zeolites in the synthesis of alkylpyrazines." Applied Catalysis A: General 208, no. 1-2 (2001): 203–11. http://dx.doi.org/10.1016/s0926-860x(00)00726-2.

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25

Schmarr, H. G., W. Sang, S. Ganß, S. Koschinski, and R. Meusinger. "New insights into the synthesis and characterization of 2-methoxy-3-alkylpyrazines and their deuterated isotopologues." Journal of Labelled Compounds and Radiopharmaceuticals 54, no. 8 (2011): 438–40. http://dx.doi.org/10.1002/jlcr.1888.

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26

Magi, Emanuele, Luca Bono, and Marina Di Carro. "Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols." Journal of Mass Spectrometry 47, no. 9 (2012): 1191–97. http://dx.doi.org/10.1002/jms.3034.

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27

Pini, Gláucia F., Edy S. de Brito, Nelson H. P. García, Antonio L. P. Valente, and Fabio Augusto. "A Headspace Solid Phase Microextraction (HS-SPME) method for the chromatographic determination of alkylpyrazines in cocoa samples." Journal of the Brazilian Chemical Society 15, no. 2 (2004): 267–71. http://dx.doi.org/10.1590/s0103-50532004000200017.

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28

Fors, Susan M., and Bertil K. Olofsson. "Alkylpyrazines, volatiles formed in the Maillard reaction. I. Determination of odour detection thresholds and odour intensity functions by dynamic olfactometry." Chemical Senses 10, no. 3 (1985): 287–96. http://dx.doi.org/10.1093/chemse/10.3.287.

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29

Rey, A., C. Gouedard, N. Ledirac, et al. "Amine degradation in CO2 capture. 2. New degradation products of MEA. Pyrazine and alkylpyrazines: Analysis, mechanism of formation and toxicity." International Journal of Greenhouse Gas Control 19 (November 2013): 576–83. http://dx.doi.org/10.1016/j.ijggc.2013.10.018.

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30

Richling, Elke, Christina Preston, Dominique Kavvadias, et al. "Determination of the2H/1H and15N/14N Ratios of Alkylpyrazines from Coffee Beans (Coffea arabicaL. andCoffea canephoravar.robusta) by Isotope Ratio Mass Spectrometry." Journal of Agricultural and Food Chemistry 53, no. 20 (2005): 7925–30. http://dx.doi.org/10.1021/jf0509613.

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31

Huang, Yang, and Sheryl A. Barringer. "Alkylpyrazines and Other Volatiles in Cocoa Liquors at pH 5 to 8, by Selected Ion Flow Tube-Mass Spectrometry (SIFT-MS)." Journal of Food Science 75, no. 1 (2010): C121—C127. http://dx.doi.org/10.1111/j.1750-3841.2009.01455.x.

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32

Gerritsma, David A., Ian D. Brindle, Timothy R. B. Jones, and Alfredo Capretta. "Preparation of labelled 2-methoxy-3-alkylpyrazines: synthesis and characterization of deuterated 2-methoxy-3-isopropylyrazine and 2-methoxy-3-isobutylpyrazine." Journal of Labelled Compounds and Radiopharmaceuticals 46, no. 3 (2003): 243–53. http://dx.doi.org/10.1002/jlcr.664.

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33

Kučerová-Chlupáčová, Marta, Veronika Opletalová, Josef Jampílek, et al. "New Hydrophobicity Constants of Substituents in Pyrazine Rings Derived from RP-HPLC Study." Collection of Czechoslovak Chemical Communications 73, no. 1 (2008): 1–18. http://dx.doi.org/10.1135/cccc20080001.

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Pyrazine derivatives show a wide range of biological activities. 1-Pyrazin-2-ylethan-1-ones have served as food flavourants, and together with pyrazine-2-carbonitriles have been widely used as intermediates in the synthesis of various heterocyclic compounds. In our laboratory, substituted pyrazine-2-carbonitriles and 1-pyrazin-2-ylethan-1-ones have been used as intermediates for the preparation of potential antifungal and antimycobacterial drugs. Using established methods, a library of pyrazine derivatives was synthesized. Homolytic alkylation of commercially available pyrazine-2-carbonitrile

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34

Ayazi, Zahra, Amir Abbas Matin, and Nargess Mohammadi-Harib. "Determination of alkylpyrazines in cocoa samples applying head-space hollow fiber protected-liquid phase microextraction followed by gas chromatography-flame ionization detection." Journal of Food Measurement and Characterization 14, no. 1 (2019): 322–32. http://dx.doi.org/10.1007/s11694-019-00294-2.

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35

Walther, U., and G. Spiteller. "Langkettige Alkylpyridine und Alkylpyrazine als Spurenbestandteile in technischer Ölsäure." Fett Wissenschaft Technologie/Fat Science Technology 95, no. 11 (1993): 424–28. http://dx.doi.org/10.1002/lipi.19930951104.

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36

Wang, Weiqiang, Jian Lv, Jianming Yang, et al. "Application of extraction and adsorption to the alkylpyrazine removal from wastewater." Desalination and Water Treatment 54, no. 1 (2014): 147–55. http://dx.doi.org/10.1080/19443994.2013.879839.

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37

Low, Mei Yin, Jane K. Parker, and Donald S. Mottram. "Mechanisms of Alkylpyrazine Formation in a Potato Model System Containing Added Glycine." Journal of Agricultural and Food Chemistry 55, no. 10 (2007): 4087–94. http://dx.doi.org/10.1021/jf070044s.

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38

Osada, Kazumi, Sadaharu Miyazono, and Makoto Kashiwayanagi. "Structure-Activity Relationships of Alkylpyrazine Analogs and Fear-Associated Behaviors in Mice." Journal of Chemical Ecology 43, no. 3 (2017): 263–72. http://dx.doi.org/10.1007/s10886-017-0822-3.

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39

Pickard, Stephanie, Helene Wilms, and Elke Richling. "Alkylpyrazine contents of coffee beverages using stable isotope dilution gas chromatography–mass spectrometry." LWT - Food Science and Technology 58, no. 1 (2014): 188–93. http://dx.doi.org/10.1016/j.lwt.2014.02.049.

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40

Houminer, Yoram, and David L. Williams. "Studies on alkylpyrazine dianions. Preparation of 5,6,11,12-tetrahydrocycloocta[1,2-b:5,6-b']dipyrazine." Journal of Heterocyclic Chemistry 22, no. 2 (1985): 373–75. http://dx.doi.org/10.1002/jhet.5570220231.

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41

Sharma, Kavita, Robert K. Vander Meer, and Henry Y. Fadamiro. "Phorid fly, Pseudacteon tricuspis, response to alkylpyrazine analogs of a fire ant, Solenopsis invicta, alarm pheromone." Journal of Insect Physiology 57, no. 7 (2011): 939–44. http://dx.doi.org/10.1016/j.jinsphys.2011.04.007.

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42

Du, Yuzhe, Michael J. Grodowitz, and Jian Chen. "Electrophysiological Responses of Eighteen Species of Insects to Fire Ant Alarm Pheromone." Insects 10, no. 11 (2019): 403. http://dx.doi.org/10.3390/insects10110403.

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Olfaction plays a dominant role in insect communication. Alarm pheromones, which alert other insects of the same species of impending danger, are a major class of releaser pheromones. The major components of alarm pheromones in red imported fire ants, honeybees and aphids have been identified as 2-ethyl-3,6-dimethylpyrazine (2E-3,6-DP), isopentyl acetate (IPA), and E-β-farnesene (EβF), respectively. In this study, electroantennography (EAG) responses to EDP (a mixture of 2-ethyl-3,6-dimethylpyrazine and 2-ethyl-3,5-dimethylpyrazine), IPA and EβF were investigated in a wide range of insect spec

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43

Pickard, Stephanie, Irina Becker, Karl-Heinz Merz, and Elke Richling. "Determination of the Alkylpyrazine Composition of Coffee Using Stable Isotope Dilution–Gas Chromatography–Mass Spectrometry (SIDA-GC-MS)." Journal of Agricultural and Food Chemistry 61, no. 26 (2013): 6274–81. http://dx.doi.org/10.1021/jf401223w.

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44

Dacho, Vladimír, Dária Nitrayová, Michal Šoral, Andrea Machyňáková, Ján Moncoľ, and Peter Szolcsányi. "Access to N-Alkylpyrazin-2-ones via C–O to C–N Rearrangement of Pyrazinyl Ethers." SynOpen 03, no. 04 (2019): 108–13. http://dx.doi.org/10.1055/s-0039-1690222.

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The reaction of tosylated 2-alkoxypyrazines with potassium halides led to the unexpected formation of N-alkylated pyrazinones. Such rare example of substitutive C–O → C–N rearrangement on pyrazines was then scrutinised by using various nucleophiles to afford the respective products in moderate to good yields. This method provides a direct access to N-alkylated-1H-pyrazin-2-ones. The formation of the rearranged products is conveniently and reliably determined by characteristic NMR shifts of their heteroaromatic protons.

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45

HASHIZUME, Katsumi, Kazuyuki TOZAWA, Yoshikazu HIRAGA, and Isao ARAMAKI. "Purification and Characterization of a O-Methyltransferase Capable of Methylating 2-Hydroxy-3-alkylpyrazine from Vitis vinifera L. (cv. Cabernet Sauvignon)." Bioscience, Biotechnology, and Biochemistry 65, no. 10 (2001): 2213–19. http://dx.doi.org/10.1271/bbb.65.2213.

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46

HASHIZUME, Katsumi, Kazuyuki TOZAWA, Masashi ENDO, and Isao ARAMAKI. "S-Adenosyl-L-methionine-dependent O-Methylation of 2-Hydroxy-3-alkylpyrazine in Wine Grapes: A Putative Final step of Methoxypyrazine Biosynthesis." Bioscience, Biotechnology, and Biochemistry 65, no. 4 (2001): 795–801. http://dx.doi.org/10.1271/bbb.65.795.

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47

YAMADA, Kenji, Youko WATANABE, Yutaka AOYAGI та Akihiro OHTA. "Effect of Alkylpyrazine Derivatives on the Duration of Pentobarbital-Induced Sleep, Picrotoxicin-Induced Convulsion and γ-Aminobutyric Acid (GABA) Levels in the Mouse Brain". Biological & Pharmaceutical Bulletin 24, № 9 (2001): 1068–71. http://dx.doi.org/10.1248/bpb.24.1068.

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48

Zhang, Lijie, Yanli Cao, Jianan Tong, and Yan Xu. "An Alkylpyrazine Synthesis Mechanism Involving L-Threonine-3-Dehydrogenase Describes the Production of 2,5-Dimethylpyrazine and 2,3,5-Trimethylpyrazine by Bacillus subtilis." Applied and Environmental Microbiology 85, no. 24 (2019). http://dx.doi.org/10.1128/aem.01807-19.

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ABSTRACT Alkylpyrazines are important contributors to the flavor of traditional fermented foods. Here, we studied the synthesis mechanisms of 2,5-dimethylpyrazine (2,5-DMP) and 2,3,5-trimethylpyrazine (TMP). Substrate addition, whole-cell catalysis, stable isotope tracing experiments, and gene manipulation revealed that l-threonine is the starting point involving l-threonine-3-dehydrogenase (TDH) and three uncatalyzed reactions to form 2,5-DMP. TDH catalyzes the oxidation of l-threonine. The product of this reaction is l-2-amino-acetoacetate, which is known to be unstable and can decarboxylate

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49

Marcinek, Patrick, Franziska Haag, Christiane Geithe, and Dietmar Krautwurst. "An evolutionary conserved olfactory receptor for foodborne and semiochemical alkylpyrazines." FASEB Journal 35, no. 6 (2021). http://dx.doi.org/10.1096/fj.202100224r.

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50

Teodorescu, Florina, Andrei Slabu, Emeric Bartha, and Octavian D. Pavel. "Catalytic synthesis of alkylpyrazines over mixed oxides obtained from LDHs materials." Journal of Material Science & Engineering 07 (2018). http://dx.doi.org/10.4172/2169-0022-c5-105.

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