Threshold-Based Structure−Activity Relationships of Pyrazines with Bell-Pepper Flavor

Buchbauer, Gerhard; Klein, Christian; Wailzer, Bettina; Wolschann, Peter

doi:10.1021/jf000192h

Cited by 37 publications

(28 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Methoxypyrazines (MPs) are potent aroma‐active components found in a range of food products, including nuts, beans, asparagus, and bell pepper, where they contribute various green characteristics such as herbaceous earthy, and vegetative (Boubee and others 2000; Buchbauer and others 2000; Sala and others 2002). They are also found as grape‐derived constituents of some juice and wine, particularly Vitis vinifera cultivars such as Cabernet Sauvignon and Merlot, where high concentrations can be unpleasant (Allen and Lacey 1998) and are associated with “unripe” characteristics.…”

Section: Introductionmentioning

confidence: 99%

Detection Thresholds for 2‐Isopropyl‐3‐Methoxypyrazine in Concord and Niagara Grape Juice

Pickering¹,

Karthik²,

Inglis³

et al. 2008

Journal of Food Science

View full text Add to dashboard Cite

2-isopropyl-3-methoxypyrazine (IPMP) is the compound responsible for the off-flavor known as ladybug taint, which occurs when Harmnonia axyridis beetles become incorporated with the grapes during juice processing. It is also an important grape-derived component of juice flavor in some varieties. The main objective of this study was to determine the orthonasal (ON) and retronasal (RN) detection thresholds for IPMP in juice. The ASTM E679 ascending forced choice method of limits was used to determine detection thresholds for 26 individuals in Concord and Niagara juices. Group best estimate thresholds (BETs) averaged 0.93 ng/L and were 50% and 21% higher in Concord than in Niagara juices for ON and RN evaluation, respectively. Group BETs for IPMP (ng/L) for Concord were ON: 1.11; RN: 1.02 and for Niagara were ON: 0.74; RN: 0.84. Variation in individual detection thresholds was observed, although familiarity with ladybug taint was not associated with individual threshold values. We conclude that humans are very sensitive to IPMP in juice, and that detection thresholds are more strongly influenced by grape variety than evaluation mode. These results may assist juice producers in establishing tolerance levels for IPMP in juice affected by ladybug taint or derived from grapes of suboptimal ripeness.

show abstract

Section: Introductionmentioning

confidence: 99%

Detection Thresholds for 2‐Isopropyl‐3‐Methoxypyrazine in Concord and Niagara Grape Juice

Pickering¹,

Karthik²,

Inglis³

et al. 2008

Journal of Food Science

View full text Add to dashboard Cite

show abstract

“…This fact makes the enantiomeric distribution a valuable parameter in authenticity studies. Furthermore, it is known the different biological activity shown by the enantiomers of some chiral compounds [8], such as linalool [9], a-pinene [10], carvone, and limonene [11], among others. Moreover, at present, the addition of racemic mixtures of chiral compounds to plant extracts is relatively frequent in the industry to enhance the natural flavor of some products.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric composition studies in Lavandula species using supercritical fluids

Flores

Blanch

Castillo

et al. 2005

J of Separation Science

View full text Add to dashboard Cite

Characteristic aroma compounds in plants and essential oils of Lavandula from different varieties were examined. The study of the qualitative and quantitative composition of the major volatile components was faced by developing a method based on the use of supercritical fluid extraction-GC-MS (SFE-GC-MS). The optimization of a variety of parameters affecting SFE extraction enabled RSDs from three replicates lower than 2% to be achieved. Equally, recoveries of up to 59% were obtained by applying the proposed method. The use of multidimensional GC was necessary to enantiomerically resolve the target compounds. The obtained results showed enantiomeric purities >90% for all studied compounds in all varieties considered, proving the natural invariability of the enantiomeric composition of the compounds of interest. This information can be useful in authenticity studies as well as in selecting natural sources of enantiomerically pure compounds.

show abstract

“…For example, pyrazines have been shown to possess powerful sensory characteristics such as toasted, roasted, nutty, sweet, breadlike and peanut-like. In addition, their threshold levels span a range in concentration from multiple ppm to unit ppb levels as a function of structure (15,23,24). The selected carboxylic acids, 2-methylpropionic, 3-methylbutyric and 3-methylpentanoic acid, are noted for their sweaty sock and cheese-like notes at ppb levels (10,25).…”

Section: Resultsmentioning

confidence: 99%

Gas Chromatographic-Selected Ion Monitoring-Mass Spectrometric Determination of Cigarette Mainstream Smoke Components with Sensory Attributes

Coleman

2004

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

View full text Add to dashboard Cite

SUMMARYA new method has been developed that detects significant quantitative differences in the amounts of pyrazines, pyridines, furfurals, carboxylic acids, -damascenone, sclareolide, and megastigmatrienones in the mainstream smoke of a series of five commercial cigarettes. This new quantitative method is based on the gas chromatographic-selected ion monitoring-mass spectrometric (GC-SIM-MS) determination of the selected smoke constituents. The accuracy and precision of the approach were well within acceptable parameters with the majority of cases relative standard deviation (RSD) values consistently around 5%. Sample preparation was simple requiring only the dissolution of the trapped particulate material in a known volume of methanol followed by injection of this clear dark colored solution into the gas chromatograph. This approach represents an advance in the technology in terms of higher sample throughput and less sample workup. Certain products demonstrated consistent trends in concentration of specific chemical classes. The mainstream smoke from a University of Kentucky reference cigarette, 2R4F, was included for reference purposes. These results are applicable in the overall evaluation of the components responsible for the taste associated with cigarette products. [Beitr. Tabakforsch. Int. 21 (2004) RESUMEUne nouvelle méthode analytique a été développée pour détecter des différences quantitatives significatives dans la teneur des pyrazines, pyridines, furfurals, acides carboxyliques, -damascénone, sclariolide et mégastigmatrièneones dans la fumée principale d'une série de cinq marques de cigarettes du marché. Cette nouvelle méthode quantitative est basée sur le dosage des composants de la fumée de tabac par chromatographie en phase gazeuse-spectrométrie de masse en mode de suivi d'ions sélectionnés (GC-SIM-MS). La précision et la fiabilité de cette approche sont acceptables avec des valeurs d'écart type relatif pour la plupart des composants d'environ 5%. La préparation des échantillons est simple, nécessitant seulement la dissolution

show abstract

Threshold-Based Structure−Activity Relationships of Pyrazines with Bell-Pepper Flavor

Cited by 37 publications

References 20 publications

Detection Thresholds for 2‐Isopropyl‐3‐Methoxypyrazine in Concord and Niagara Grape Juice

Detection Thresholds for 2‐Isopropyl‐3‐Methoxypyrazine in Concord and Niagara Grape Juice

Enantiomeric composition studies in Lavandula species using supercritical fluids

Gas Chromatographic-Selected Ion Monitoring-Mass Spectrometric Determination of Cigarette Mainstream Smoke Components with Sensory Attributes

Contact Info

Product

Resources

About