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Journal articles on the topic 'Methoxypyrazines'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Rajchl, A., H. Čížková, M. Voldřich, D. Lukešová, and Z. Panovská. "Methoxypyrazines in Sauvignon blanc wines, detection of addition of artificial aroma." Czech Journal of Food Sciences 27, No. 4 (September 9, 2009): 259–66. http://dx.doi.org/10.17221/4/2009-cjfs.

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Methoxypyrazines are the principal aroma components responsible for the vegetative and herbaceous green bell-pepper flavour of Sauvignon blanc wines produced in Moravia. The aroma profiles of 8 samples of Moravian Sauvignon wines were analysed; the levels of 3-isobutyl-2-methoxypyrazine varied in the range of 4.7–17.0 ng/l. The commercial Sauvignon aroma preparation Aroma Fantasia S, available in the region, was analysed; the product contained the 3-isobutyl-2-methoxypyrazine, and in negligible concentrations also anethol and ethylbenzoate. The Moravian Sauvignon blanc wine samples spiked with different amounts of aroma preparation were evaluated by hedonic sensory analysis, to estimate the meaningfulness of such illegal improvement. The most preferred concentration ranged from 5 ng/l to 10 ng/l, which are the natural levels of MP in Moravian Sauvignon blanc wines, therefore the addition of aroma at this level, which can be detectable with difficulties, has no reason. The less sophisticated adulteration of wine, such as the production of artificial Sauvignon blanc wine by the addition of MP into less distinctive wines, is easily detectable according to the aroma profile.

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2

HASHIZUME, Katsumi. "Methoxypyrazines in Wine." JOURNAL OF THE BREWING SOCIETY OF JAPAN 94, no. 12 (1999): 966–73. http://dx.doi.org/10.6013/jbrewsocjapan1988.94.966.

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3

J Pickering, G., A. Blake, and Y. Kotseridis. "Effect of Closure, Packaging and Storage Conditions on Impact Odorants of Wine." Czech Journal of Food Sciences 27, Special Issue 1 (June 24, 2009): S62—S65. http://dx.doi.org/10.17221/1104-cjfs.

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3-alkyl-2-methoxypyrazines (MPs) represent an important and potent class of odor-active compounds associated with wine quality. 30 ng/l each of 3-isobutyl-2-methoxypyrazine, 3-isopropyl-2-methoxypyrazine and 3-secbutyl-2-methoxypyrazine were added to a Riesling and Cabernet Franc wine and monitored with HS-SPME-GC-MS over 18 months to investigate the effects of various closure and packaging options as well as light and storage temperature on MPs. Other impact odorants were monitored using SPE-GC-FID. Changes in MP concentrations during bottle aging varied with closure/packaging option, with the greatest decrease evident in Tetrapak® cartons. We observed similar changes in other impact odorants to previous studies, with synthetic corks displaying an increased capacity for sorption compared to natural corks and screwcaps. MPs did not vary consistently over time with light or temperature conditions. Acetate esters decreased, regardless of light or temperature conditions, while phenethyl acetate and isoamyl acetate decreased at a greater rate in ambient temperature conditions compared with 12°C. Free and bound SO<sub>2</sub> retention was higher in light-excluded conditions and influenced by bottle hue.

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4

Pickering, Gary J., and Andreea Botezatu. "A Review of Ladybug Taint in Wine: Origins, Prevention, and Remediation." Molecules 26, no. 14 (July 17, 2021): 4341. http://dx.doi.org/10.3390/molecules26144341.

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Ladybug taint (also known as ladybird taint) is a relatively recently recognized fault that has been identified in wines from a wide range of terroirs. Alkyl-methoxypyrazines—particularly 2-isopropyl-3-methoxypyrazine—have been determined as the causal compounds, and these are introduced into grape must during processing, when specific species of vineyard-dwelling Coccinellidae are incorporated into the harvested fruit. Coccinella septempunctata, and especially the invasive Harmonia axyridis, are the beetles implicated, and climate change is facilitating wider dispersal and survivability of H. axyridis in viticultural regions worldwide. Affected wines are typically characterized as possessing excessively green, bell pepper-, and peanut-like aroma and flavor. In this paper, we review a range of vineyard practices that seek to reduce Coccinellidae densities, as well as both “standard” and novel wine treatments aimed at reducing alkyl-methoxypyrazine load. We conclude that while prevention of ladybug taint is preferable, there are several winery interventions that can remediate the quality of wine affected by this taint, although they vary in their relative efficacy and specificity.

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Botezatu, Andreea, and Gary James Pickering. "Novel Applications for Biomaterials: The Case of Remediation of Wine Taints Using Poly-Lactic Acid Polymer." Applied Mechanics and Materials 749 (April 2015): 70–73. http://dx.doi.org/10.4028/www.scientific.net/amm.749.70.

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Wine is the world’s oldest alcoholic beverage and the most consumed in at least 20 countries. However, taints detract from its quality and acceptance, significantly reducing the value of wine. In this study we investigated the capacity of a poly-lactic acid (PLA) biopolymer to reduce concentrations of four odorants responsible for tainting many red wines: isopropyl-methoxypyrazine (IPMP), isobutyl–methoxypyrazine (IBMP), 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG). Red wine was spiked with either IPMP [20 ng/L] and IBMP [20 ng/L] (Study 1) or 4-EP [200 ug/L] and 4-EG [200 ug/L] (Study 2) and then treated with a PLA film [surface area 350 cm2/L]. Solid Phase Micro-Extraction Multi-Dimensional Gas Chromatography–Mass Spectrometry and Gas Chromatography-Mass Spectrometry were used to measure the methoxypyrazines and ethylphenols, respectively, both before and after treatment with PLA. Results showed significant reductions in all of the target odorants after 8hrs treatment: IPMP (51%), IBMP (26%), 4-EP (21%) and 4-EG (20%). Taken overall, the data suggest potential for the use of PLA in treating common wine faults, particularly ‘ladybug taint’, which is caused by elevated levels of IPMP.

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6

Brunetti, Andrés E., Mariana L. Lyra, Weilan G. P. Melo, Laura E. Andrade, Pablo Palacios-Rodríguez, Bárbara M. Prado, Célio F. B. Haddad, Mônica T. Pupo, and Norberto P. Lopes. "Symbiotic skin bacteria as a source for sex-specific scents in frogs." Proceedings of the National Academy of Sciences 116, no. 6 (January 22, 2019): 2124–29. http://dx.doi.org/10.1073/pnas.1806834116.

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Amphibians are known to possess a wide variety of compounds stored in their skin glands. While significant progress has been made in understanding the chemical diversity and biological relevance of alkaloids, amines, steroids, and peptides, most aspects of the odorous secretions are completely unknown. In this study, we examined sexual variations in the volatile profile from the skin of the tree frogBoana prasinaand combined culture and culture-independent methods to investigate if microorganisms might be a source of these compounds. We found that sesquiterpenes, thioethers, and methoxypyrazines are major contributors to the observed sex differences. We also observed that each sex has a distinct profile of methoxypyrazines, and that the chemical origin of these compounds can be traced to aPseudomonassp. strain isolated from the frog’s skin. This symbiotic bacterium was present in almost all individuals examined from different sites and was maintained in captive conditions, supporting its significance as the source of methoxypyrazines in these frogs. Our results highlight the potential relevance of bacteria as a source of chemical signals in amphibians and contribute to increasing our understanding of the role that symbiotic associations have in animals.

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7

Battilana, Juri, Jake D. Dunlevy, and Paul K. Boss. "Histone modifications at the grapevine VvOMT3 locus, which encodes an enzyme responsible for methoxypyrazine production in the berry." Functional Plant Biology 44, no. 7 (2017): 655. http://dx.doi.org/10.1071/fp16434.

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Some herbaceous characters in wine are attributed to the presence of aroma compounds collectively known as methoxypyrazines (MPs). In grape berries their formation has been hypothesised to start from a reaction of two amino acids or an amino acid and an unknown 1,2-dicarbonyl compound, leading to the formation of hydroxypyrazine, which is then enzymatically methylated to form a MP. The enzyme responsible of the formation of 3-isobutyl-2-methoxypyrazine has been recently identified as VvOMT3 whose regulation is still not understood. The concentration of MPs in grapes is known to be influenced by development, environmental stimuli and most importantly grape variety. In order to investigate the chromatin arrangement of that region a chromatin immunoprecipitation analysis has been performed and putative differences in epigenetic regulation of VvOMT3 spatially between the skin and flesh tissues and also temporally during fruit development have been detected. There are also allelic differences in VvOMT3 histone modifications which are maintained in subsequent generations. This study provides evidence of histone tail modification of the VvOMT3 locus in grapevine, which may play a role in the spatial and developmental regulation of the expression of this gene.

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8

Olejar, Kenneth J., Jason Breitmeyer, Pradeep M. Wimalasiri, Bin Tian, and Stewart K. Field. "Detection of Sub-Aroma Threshold Concentrations of Wine Methoxypyrazines by Multidimensional GCMS." Analytica 2, no. 1 (January 2, 2021): 1–13. http://dx.doi.org/10.3390/analytica2010001.

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Complex matrices, such as wine, provide a challenge in the quantification of compounds. There exists a high likelihood of co-elution in these matrices, thereby artificially increasing the observed concentration. This can often lead to confusing data where compounds are above aroma detection thresholds, but are not detected by olfactory analysis. Additionally, the lack of sensitivity in assays can lead to the non-detection of sub-aroma threshold concentrations and contrasting data when olfactory analysis detects these aromas. To eliminate these pitfalls and gain a better understanding of the role that methoxypyrazines impart green character to wine, a quantitative method using headspace solid-phase microextraction coupled to heart-cutting multidimensional gas chromatography mass spectrometry was developed. The method can quantitate the three common methoxypyrazines found in wine at the picogram per liter level while resolving co-eluting compounds. The proposed method was validated using model wine and wine solutions and was ultimately used for the comparative analysis of white, rosé, and red wines.

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9

Lei, Yujuan, Sha Xie, Xueqiang Guan, Changzheng Song, Zhenwen Zhang, and Jiangfei Meng. "Methoxypyrazines biosynthesis and metabolism in grape: A review." Food Chemistry 245 (April 2018): 1141–47. http://dx.doi.org/10.1016/j.foodchem.2017.11.056.

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10

Ling, Mengqi, Yu Zhou, Yibin Lan, Chifang Cheng, Guangfeng Wu, Changqing Duan, and Ying Shi. "Modification of Sensory Expression of 3-Isobutyl-2-methoxypyrazine in Wines through Blending Technique." Molecules 26, no. 11 (May 26, 2021): 3172. http://dx.doi.org/10.3390/molecules26113172.

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Sensory interactions exist between 3-alkyl-2-methoxypyrazines and various volatiles in wines. In this study, the binary blending of Cabernet Franc wines containing high levels of MPs and three monovarietal red wines with two proportions was conducted after fermentation. Volatiles were detected by gas chromatography-mass spectrometry (GC-MS), and wines were evaluated by quantitative descriptive analysis at three-month intervals during six-month bottle aging. Results showed blending wines exhibited lower intensity of ‘green pepper’, especially CFC samples blended by Cabernet Sauvignon wines with an even higher concentration of 3-isobutyl-2-methoxypyrazine (IBMP). Based on Pearson correlation analysis, acetates could promote the expression of ‘tropical fruity’ and suppress ‘green pepper’ caused by IBMP. Positive correlation was observed among ‘green pepper’, ‘herbaceous’, and ‘berry’. The concentration balance between IBMP and other volatiles associated with ‘green pepper’ and fruity notes was further investigated through sensory experiments in aroma reconstitution. Higher pleasant fruity perception was obtained with the concentration proportion of 1-hexanol (1000 μg/L), isoamyl acetate (550 μg/L), ethyl hexanoate (400 μg/L), and ethyl octanoate (900 μg/L) as in CFC samples. Blending wines with proper concentration of those volatiles would be efficient to weaken ‘green pepper’ and highlight fruity notes, which provided scientific theory on sensory modification of IBMP through blending technique.

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11

Candelon, Nicolas, Svitlana Shinkaruk, Bernard Bennetau, Catherine Bennetau-Pelissero, Marie-Laurence Dumartin, Marie Degueil, and Pierre Babin. "New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors." Tetrahedron 66, no. 13 (March 2010): 2463–69. http://dx.doi.org/10.1016/j.tet.2010.01.088.

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12

Heymann, Hildegarde, Ann C. Noble, and Roger B. Boulton. "Analysis of methoxypyrazines in wines. 1. Development of a quantitative procedure." Journal of Agricultural and Food Chemistry 34, no. 2 (March 1986): 268–71. http://dx.doi.org/10.1021/jf00068a029.

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13

Plank, Cassandra M., Edward W. Hellman, and Thayne Montague. "Light and Temperature Independently Influence Methoxypyrazine Content of Vitis vinifera (cv. Cabernet Sauvignon) Berries." HortScience 54, no. 2 (February 2019): 282–88. http://dx.doi.org/10.21273/hortsci13634-18.

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Methoxypyrazines (MPs) are fruit-derived extractable compounds that contribute to cultivar-specific aroma traits in wine, and greater concentrations can contribute to unpleasant vegetative aromas. Both light exposure and temperature have been reported to influence MP content in developing wine grapes, but individual effects of light and temperature are confounded. A novel method of manipulating light exposure with light-emitting diodes (LEDs) was used to impose light treatments with little or no effect on cluster temperature. Three treatments were imposed on developing fruit of Vitis vinifera (cv. Cabernet Sauvignon): 1) clusters exposed to direct sunlight, 2) clusters shaded by the grapevine canopy, and 3) clusters shaded by the canopy and exposed to supplemental LED light. Experiments were conducted over 3 years across pre- and postveraison periods of fruit development. A second experiment imposed the same light exposure treatments to ripening clusters on vines experiencing continual shoot growth during the postveraison period. Light exposure reduced 3-isobutyl-2-methoxypyrazine (IBMP) concentration of developing grape berries in the preveraison period independently of berry heating from solar radiation. Berry IBMP responded less to postveraison light levels, except on vines with active shoot growth, suggesting IBMP synthesis was continued during active vine growth but was suppressed by light. An inverse relationship of growing degree days (GDDs) with berry IBMP was observed, indicating high temperatures also reduce berry IBMP concentration. Response to temperature could result from either radiant heating of light-exposed clusters or from high ambient air temperature. Canopy management should consider the impact of both light and temperature on IBMP, and vine management practices should be adjusted appropriately to regional growing conditions and grape cultivars.

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14

Sala, C., M. Mestres, M. P. Martı́, O. Busto, and J. Guasch. "Headspace solid-phase microextraction analysis of 3-alkyl-2-methoxypyrazines in wines." Journal of Chromatography A 953, no. 1-2 (April 2002): 1–6. http://dx.doi.org/10.1016/s0021-9673(02)00123-1.

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15

Allen, Malcolm S., Michael J. Lacey, and Stephen J. Boyd. "Methoxypyrazines in Red Wines: Occurrence of 2-Methoxy-3-(1-methylethyl)pyrazine." Journal of Agricultural and Food Chemistry 43, no. 3 (March 1995): 769–72. http://dx.doi.org/10.1021/jf00051a038.

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16

Botezatu, Andreea I., Yorgos Kotseridis, Debbie Inglis, and Gary J. Pickering. "Occurrence and contribution of alkyl methoxypyrazines in wine tainted byHarmonia axyridisandCoccinella septempunctata." Journal of the Science of Food and Agriculture 93, no. 4 (October 19, 2012): 803–10. http://dx.doi.org/10.1002/jsfa.5800.

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17

Battistutta, F., G. Colugnati, F. Bregant, G. Crespan, I. Tonetti, E. Celotti, and R. Zironi. "INFLUENCE OF GENOTYPE ON THE METHOXYPYRAZINES CONTENT OF CABERNET SAUVIGNON CULTIVATED IN FRIULI." Acta Horticulturae, no. 526 (March 2000): 407–14. http://dx.doi.org/10.17660/actahortic.2000.526.45.

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18

Mutarutwa, Delvana, Luciano Navarini, Valentina Lonzarich, Dario Compagnone, and Paola Pittia. "GC-MS aroma characterization of vegetable matrices: Focus on 3-alkyl-2-methoxypyrazines." Journal of Mass Spectrometry 53, no. 9 (August 16, 2018): 871–81. http://dx.doi.org/10.1002/jms.4271.

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19

Vallarino, José G., Xaviera A. López-Cortés, Jake D. Dunlevy, Paul K. Boss, Fernando D. González-Nilo, and Yerko M. Moreno. "Biosynthesis of Methoxypyrazines: Elucidating the Structural/Functional Relationship of TwoVitis viniferaO-Methyltransferases Capable of Catalyzing the Putative Final Step of the Biosynthesis of 3-Alkyl-2-Methoxypyrazine." Journal of Agricultural and Food Chemistry 59, no. 13 (July 13, 2011): 7310–16. http://dx.doi.org/10.1021/jf200542w.

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20

Romero, Raquel, Juan Luis Chacón, Esteban García, and Jesús Martínez. "Pyrazine contents in four red grape varietes cultivated in warm climate." OENO One 40, no. 4 (December 31, 2006): 203. http://dx.doi.org/10.20870/oeno-one.2006.40.4.861.

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<p style="text-align: justify;">We analysed 2-methoxy-3-ethylpyrazine and 2-methoxy-3-isobutylpyrazine content in 4 grape varieties cultivated in Castilla-La Mancha. A sensory analysis of the wines obtained from these grapes was also performed. The results revealed the presence of the two methoxypyrazines studied in all four varieties, in concentrations lower than those published for these varieties in regions with cooler climates. Significant differences were observed in 2-methoxy-3-isobutylpyrazine content between the different varieties: Cabernet-Sauvignon>Merlot>Syrah>Cencibel. The correlation between 2- methoxy-3-isobutylpyrazine content and the « green pepper » descriptor suggests a perception threshold at 3 ng/L in young wines.</p>

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21

Allen, Malcolm S., Michael J. Lacey, and Stephen Boyd. "Determination of Methoxypyrazines in Red Wines by Stable Isotope Dilution Gas Chromatography-Mass Spectrometry." Journal of Agricultural and Food Chemistry 42, no. 8 (August 1994): 1734–38. http://dx.doi.org/10.1021/jf00044a030.

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22

Rizzi, George P. "Formation of methoxypyrazines in reactions of 2(1H)-pyrazinones with naturally occurring methylating agents." Journal of Agricultural and Food Chemistry 38, no. 10 (October 1990): 1941–44. http://dx.doi.org/10.1021/jf00100a014.

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23

Ventura, Francesc, Jordi Quintana, Mariano Gómez, and Mónica Velo-Cid. "Identification of Alkyl-methoxypyrazines as the Malodorous Compounds in Water Supplies from Northwest Spain." Bulletin of Environmental Contamination and Toxicology 85, no. 2 (July 6, 2010): 160–64. http://dx.doi.org/10.1007/s00128-010-0053-6.

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24

Zhao, Xianfang, Yanlun Ju, Xiaofeng Wei, Shuo Dong, Xiangyu Sun, and Yulin Fang. "Significance and Transformation of 3-Alkyl-2-Methoxypyrazines Through Grapes to Wine: Olfactory Properties, Metabolism, Biochemical Regulation, and the HP–MP Cycle." Molecules 24, no. 24 (December 16, 2019): 4598. http://dx.doi.org/10.3390/molecules24244598.

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3-Alkyl-2-methoxypyrazines (MPs) contribute to the herbaceous flavor characteristics of wine and are generally considered associated with poor-quality wine. To control the MPs in grapes and wine, an accurate understanding of MP metabolism is needed. This review covers factors affecting people in the perception of MPs. Also, the history of O-methyltransferases is revisited, and the present review discusses the MP biosynthesis, degradation, and biochemical regulation. We propose the existence of a cycle between MPs and 3-alkyl-2-hydropyrazines (HPs), which proceeds via O-(de)methylation steps. This cycle governs the MP contents of wines, which make the cycle the key participant in MP regulation by genes, environmental stimuli, and microbes. In conclusion, a comprehensive metabolic pathway on which the HP–MP cycle is centered is proposed after gaining insight into their metabolism and regulation. Some directions for future studies on MPs are also proposed in this paper.

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25

Galvan, Tederson Luiz, Stephen Kells, and William Dale Hutchison. "Determination of 3-Alkyl-2-methoxypyrazines in Lady Beetle-Infested Wine by Solid-Phase Microextraction Headspace Sampling." Journal of Agricultural and Food Chemistry 56, no. 3 (February 2008): 1065–71. http://dx.doi.org/10.1021/jf072382z.

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26

Dunlevy, Jake D., Kathleen L. Soole, Michael V. Perkins, Eric G. Dennis, Robert A. Keyzers, Curtis M. Kalua, and Paul K. Boss. "Two O-methyltransferases involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour." Plant Molecular Biology 74, no. 1-2 (June 23, 2010): 77–89. http://dx.doi.org/10.1007/s11103-010-9655-y.

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27

Fontana, Ariel R., and Rubén Bottini. "QuEChERS Method for the Determination of 3‑Alkyl‑2‑Methoxypyrazines in Wines by Gas Chromatography-Mass Spectrometry." Food Analytical Methods 9, no. 12 (May 10, 2016): 3352–59. http://dx.doi.org/10.1007/s12161-016-0532-4.

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28

Mutarutwa, Delvana, Luciano Navarini, Valentina Lonzarich, Paola Crisafulli, Dario Compagnone, and Paola Pittia. "Determination of 3-Alkyl-2-methoxypyrazines in Green Coffee: A Study To Unravel Their Role on Coffee Quality." Journal of Agricultural and Food Chemistry 68, no. 17 (December 16, 2019): 4743–51. http://dx.doi.org/10.1021/acs.jafc.9b07476.

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29

Kotseridis, Y. S., M. Spink, I. D. Brindle, A. J. Blake, M. Sears, X. Chen, G. Soleas, D. Inglis, and G. J. Pickering. "Quantitative analysis of 3-alkyl-2-methoxypyrazines in juice and wine using stable isotope labelled internal standard assay." Journal of Chromatography A 1190, no. 1-2 (May 2008): 294–301. http://dx.doi.org/10.1016/j.chroma.2008.02.088.

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30

Frato, Katherine E. "Identification of Hydroxypyrazine O-Methyltransferase Genes in Coffea arabica: A Potential Source of Methoxypyrazines That Cause Potato Taste Defect." Journal of Agricultural and Food Chemistry 67, no. 1 (December 7, 2018): 341–51. http://dx.doi.org/10.1021/acs.jafc.8b04541.

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Sala, C., M. Mestres, M. P. Martı́, O. Busto, and J. Guasch. "Headspace solid-phase microextraction method for determining 3-alkyl-2-methoxypyrazines in musts by means of polydimethylsiloxane–divinylbenzene fibres." Journal of Chromatography A 880, no. 1-2 (June 2000): 93–99. http://dx.doi.org/10.1016/s0021-9673(00)00262-4.

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32

Maia, Artur Campos Dália, Geanne Karla Novais Santos, Eduardo Gomes Gonçalves, Daniela Maria do Amaral Ferraz Navarro, and Luis Alberto Nuñez-Avellaneda. "2-Alkyl-3-methoxypyrazines are potent attractants of florivorous scarabs (Melolonthidae, Cyclocephalini) associated with economically exploitable Neotropical palms (Arecaceae)." Pest Management Science 74, no. 9 (March 25, 2018): 2053–58. http://dx.doi.org/10.1002/ps.4895.

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33

Godelmann, Rolf, Susanne Limmert, and Thomas Kuballa. "Implementation of headspace solid-phase-microextraction–GC–MS/MS methodology for determination of 3-alkyl-2-methoxypyrazines in wine." European Food Research and Technology 227, no. 2 (October 17, 2007): 449–61. http://dx.doi.org/10.1007/s00217-007-0741-6.

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34

Slabizki, Petra, Charlotte Legrum, Reinhard Meusinger, and Hans-Georg Schmarr. "Characterization and analysis of structural isomers of dimethyl methoxypyrazines in cork stoppers and ladybugs (Harmonia axyridis and Coccinella septempunctata)." Analytical and Bioanalytical Chemistry 406, no. 25 (August 14, 2014): 6429–39. http://dx.doi.org/10.1007/s00216-014-8049-4.

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35

Dunlevy, Jake D., Kathleen L. Soole, Michael V. Perkins, Eric G. Dennis, Robert A. Keyzers, Curtis M. Kalua, and Paul K. Boss. "Erratum to: Two O-methyltransferases involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour." Plant Molecular Biology 81, no. 4-5 (February 8, 2013): 523. http://dx.doi.org/10.1007/s11103-013-0012-9.

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36

Ryan, Danielle, Peter Watkins, Jason Smith, Malcolm Allen, and Philip Marriott. "Analysis of methoxypyrazines in wine using headspace solid phase microextraction with isotope dilution and comprehensive two-dimensional gas chromatography." Journal of Separation Science 28, no. 9-10 (June 2005): 1075–82. http://dx.doi.org/10.1002/jssc.200500097.

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37

Blake, Amy, Yorgos Kotseridis, Ian D. Brindle, Debbie Inglis, M. Sears, and Gary J. Pickering. "Effect of Closure and Packaging Type on 3-Alkyl-2-methoxypyrazines and Other Impact Odorants of Riesling and Cabernet Franc Wines." Journal of Agricultural and Food Chemistry 57, no. 11 (June 10, 2009): 4680–90. http://dx.doi.org/10.1021/jf803720k.

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38

Kögel, Susanne, Jürgen Gross, Christoph Hoffmann, and Detlef Ulrich. "Diversity and frequencies of methoxypyrazines in hemolymph of Harmonia axyridis and Coccinella septempunctata and their influence on the taste of wine." European Food Research and Technology 234, no. 3 (December 17, 2011): 399–404. http://dx.doi.org/10.1007/s00217-011-1646-y.

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39

Slabizki, Petra, Charlotte Legrum, Reinhard Meusinger, and Hans-Georg Schmarr. "Erratum to: Characterization and analysis of structural isomers of dimethyl methoxypyrazines in cork stoppers and ladybugs (Harmonia axyridis and Coccinella septempunctata)." Analytical and Bioanalytical Chemistry 406, no. 29 (September 17, 2014): 7743–44. http://dx.doi.org/10.1007/s00216-014-8164-2.

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Sala, Cristina, Olga Busto, Josep Guasch, and Fernando Zamora. "Contents of 3-alkyl-2-methoxypyrazines in musts and wines fromVitis vinifera variety Cabernet Sauvignon: influence of irrigation and plantation density." Journal of the Science of Food and Agriculture 85, no. 7 (2005): 1131–36. http://dx.doi.org/10.1002/jsfa.2068.

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Vatansever, Serap, Minwei Xu, Ana Magallanes-López, Bingcan Chen, and Clifford Hall. "Supercritical Carbon Dioxide + Ethanol Extraction to Improve Organoleptic Attributes of Pea Flour with Applications of Sensory Evaluation, HS-SPME-GC, and GC-Olfactory." Processes 9, no. 3 (March 9, 2021): 489. http://dx.doi.org/10.3390/pr9030489.

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Supercritical carbon dioxide + ethanol (SC-CO2+EtOH) extraction, was employed as a deflavoring method to improve the sensory properties of pea flours. Furthermore, the impacts of particle size along with extraction on volatile profile and sensory attributes of pea flours were investigated using multiple approaches. These included headspace solid-phase microextraction-gas chromatography (HS-SPME-GC), GC-olfactometry (GC-O), and quantitative descriptive analysis (QDA) using a trained sensory panel. Total volatile contents of non-deflavored and deflavored whole pea flour and its fractions were in the range of 7.1 ± 0.3 to 18.1 ± 1.0 µg/g and 0.4 ± 0.1 to 2.7 ± 0.4 µg/g, respectively. The GC-O system showed that the total volatile intensity was in the range of 14.5 to 22.0 and 0 to 3.5, for non-deflavored and deflavored pea flours, respectively. Volatile analyses indicated that 1-hexanol, 1-octanol, 1-nonanol, nonanal, and 2-alkyl methoxypyrazines were major off-aroma compounds. Most off-aroma compounds were not detected in deflavored pea flours. QDA revealed less pea intensity and bitterness of deflavored pea flours. The larger particle size of flours resulted in less off-aroma compounds based on the GC data but more bitterness based on QDA. The SC-CO2+EtOH extraction at optimum conditions and particle size modifications can be a potential technology to improve the organoleptic properties of pulse ingredients.

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Burdfield-Steel, Emily R., Jutta M. Schneider, Johanna Mappes, and Susanne Dobler. "Testing the effectiveness of pyrazine defences against spiders." Chemoecology 30, no. 4 (March 7, 2020): 139–46. http://dx.doi.org/10.1007/s00049-020-00305-5.

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Abstract Insects live in a dangerous world and may fall prey to a wide variety of predators, encompassing multiple taxa. As a result, selection may favour defences that are effective against multiple predator types, or target-specific defences that can reduce predation risk from particular groups of predators. Given the variation in sensory systems and hunting tactics, in particular between vertebrate and invertebrate predators, it is not always clear whether defences, such as chemical defences, that are effective against one group will be so against another. Despite this, the majority of research to date has focused on the role of a single predator species when considering the evolution of defended prey. Here we test the effectiveness of the chemical defences of the wood tiger moth, a species previously shown to have defensive chemicals targeted towards ants, against a common invertebrate predator: spiders. We presented both live moths and artificial prey containing their defensive fluids to female Trichonephila senegalensis and recorded their reactions. We found that neither of the moth’s two defensive fluids were able to repel the spiders, and confirmed that methoxypyrazines, a major component of the defences of both the wood tiger moth and many insect species, are ineffective against web-building spiders. Our results highlight the variability between predator taxa in their susceptibility to chemical defences, which can in part explain the vast variation in these chemicals seen in insects, and the existence of multiple defences in a single species.

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Buettner, Andrea. "Influence of Human Saliva on Odorant Concentrations. 2. Aldehydes, Alcohols, 3-Alkyl-2-methoxypyrazines, Methoxyphenols, and 3-Hydroxy-4,5-dimethyl-2(5H)-furanone." Journal of Agricultural and Food Chemistry 50, no. 24 (November 2002): 7105–10. http://dx.doi.org/10.1021/jf020714o.

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Sala, Cristina, Olga Busto, Josep Guasch, and Fernando Zamora. "Influence of Vine Training and Sunlight Exposure on the 3-Alkyl-2-methoxypyrazines Content in Musts and Wines from theVitis viniferaVariety Cabernet Sauvignon." Journal of Agricultural and Food Chemistry 52, no. 11 (June 2004): 3492–97. http://dx.doi.org/10.1021/jf049927z.

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Botezatu, Andreea, Gary J. Pickering, and Yorgos Kotseridis. "Development of a rapid method for the quantitative analysis of four methoxypyrazines in white and red wine using multi-dimensional Gas Chromatography – Mass Spectrometry." Food Chemistry 160 (October 2014): 141–47. http://dx.doi.org/10.1016/j.foodchem.2014.03.044.

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Legrum, Charlotte, Elisa Gracia-Moreno, Ricardo Lopez, Theodoros Potouridis, Johannes Langen, Petra Slabizki, Jörg Weiand, and Hans-Georg Schmarr. "Quantitative analysis of 3-alkyl-2-methoxypyrazines in German Sauvignon blanc wines by MDGC–MS or MDGC–MS/MS for viticultural and enological studies." European Food Research and Technology 239, no. 4 (May 15, 2014): 549–58. http://dx.doi.org/10.1007/s00217-014-2250-8.

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López, Ricardo, Elisa Gracia-Moreno, Juan Cacho, and Vicente Ferrreira. "Development of a mixed-mode solid phase extraction method and further gas chromatography mass spectrometry for the analysis of 3-alkyl-2-methoxypyrazines in wine." Journal of Chromatography A 1218, no. 6 (February 2011): 842–48. http://dx.doi.org/10.1016/j.chroma.2010.12.048.

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Panighel, Annarita, Antonio Dalla Vedova, Mirko De Rosso, Massimo Gardiman, and Riccardo Flamini. "A solid-phase microextraction gas chromatography/ion trap tandem mass spectrometry method for simultaneous determination of ‘foxy smelling compounds’ and 3-alkyl-2-methoxypyrazines in grape juice." Rapid Communications in Mass Spectrometry 24, no. 14 (June 15, 2010): 2023–29. http://dx.doi.org/10.1002/rcm.4611.

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Culleré, Laura, Ana Escudero, Eva Campo, Juan Cacho, and Vicente Ferreira. "Multidimensional gas chromatography–mass spectrometry determination of 3-alkyl-2-methoxypyrazines in wine and must. A comparison of solid-phase extraction and headspace solid-phase extraction methods." Journal of Chromatography A 1216, no. 18 (May 2009): 4040–45. http://dx.doi.org/10.1016/j.chroma.2009.02.072.

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Fontana, Ariel, Isaac Rodríguez, and Rafael Cela. "Accurate determination of 3-alkyl-2-methoxypyrazines in wines by gas chromatography quadrupole time-of-flight tandem mass spectrometry following solid-phase extraction and dispersive liquid–liquid microextraction." Journal of Chromatography A 1515 (September 2017): 30–36. http://dx.doi.org/10.1016/j.chroma.2017.07.085.

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