Stable Isotope Dilution Gas Chromatography-Mass Spectrometry for Determination of Methoxypyrazines (“Green” Aroma) in Wine

Allen, Malcolm S.; Lacey, Michael J.

doi:10.1007/978-3-662-03331-9_10

Cited by 9 publications

(7 citation statements)

References 33 publications

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“…The 2-alkyl-3-methoxypyrazines are known for their extremely low sensory detection threshold in both wine and water samples. 14 This work therefore demonstrates the principles of the static headspace sampling technique coupled with GC/MS to investigate three different species of ladybugs (Coccinella septempunctata, Harmonia axyridis and Hippodemia convergens, Fig. 1) belonging the Coccinellidae family in order to establish the presence of the 2-alkyl-3-methoxypyrazine pheromones and thereby link its consequential effect to wine flavour.…”

Section: Introductionmentioning

confidence: 87%

Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3- methoxypyrazine pheromones in ladybugs

Cudjoe

Wiederkehr

Brindle

2005

Analyst

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Static headspace sampling technique coupled with gas chromatography and mass spectrometry was used to investigate the presence of volatile 2-alkyl-3-methoxypyrazines in three different species of ladybugs of the Coccinellidae family. The species investigated were Coccinella septempunctata, Harmonia axyridis and Hippodemia convergens. 2-isopropyl-3-methoxypyrazine (IPMP) was identified in all three species with detectable levels of 2-sec-butyl-3-methoxypyrazine (SBMP) and 3-isobutyl-2-methoxypyrazines (IBMP) in only Hippodemia convergens and Harmonia axyridis species. Relative amounts of 2-alkyl-3-methoxypyrazines based on body mass showed that Hippodemia convergens had the highest levels of all three methoxypyrazines and Coccinella septempunctata the least.

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Section: Introductionmentioning

confidence: 87%

Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3- methoxypyrazine pheromones in ladybugs

Cudjoe

Wiederkehr

Brindle

2005

Analyst

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“…Methoxypyrazines are strikingly potent odorants which are present in the berries of some grape varieties, particularly Sauvignon blanc and Cabernet Sauvignon [1]. They have a vegetative, herbaceous odour [2], similar to bellpepper, and a very low sensory threshold of between 1 -10 ng/L in water [3].…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, quadrapole MS [1,2,5,9,10] and ion trap MS [4] have been used, with selected ion monitoring; reported detection limits for IBMP in wine ranged from 0.7 ng/L with quadrupole MS [5] to 1 ng/L for ion trap MS [4]. Development of a definitive MS method is best achieved using a stable isotope-labeled analogue of the analyte as an internal standard (cited in [1]), and has been reported in other studies [4,5,9]. The same approach is performed in the present case for the quantitation of IBMP.…”

Section: Introductionmentioning

confidence: 99%

Analysis of methoxypyrazines in wine using headspace solid phase microextraction with isotope dilution and comprehensive two‐dimensional gas chromatography

Ryan

Watkins

Smith

et al. 2005

J of Separation Science

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This study reports an optimized headspace-solid phase microextraction (HS-SPME) method for the determination of methoxypyrazines in wine. Analysis was performed by using comprehensive two-dimensional gas chromatography with novel detection capabilities, including nitrogen phosphorus detection (GC x GC-NPD) and time-of-flight mass spectrometry (GC x GC-TOFMS). In the latter, stable isotope dilution was performed for the quantitation of 2-methoxy-3-(2-methylpropyl) pyrazine (IBMP), using labelled 2-(2H3)methoxy-3-(2-methylpropyl)pyrazine (d3-IBMP) as the internal standard, and resolution of the two analogues was facilitated using the deconvolution capabilities of the TOFMS. This research represents the first report of HS-SPME with isotope dilution and GC x GC-TOFMS (GC x GC-IDTOFMS). Analysis by GC x GC-NPD enabled detection limits of 0.5 ng/L for the quantitation of IBMP, which was superior to that obtained using GC x GC-IDTOFMS (1.95 ng/L). Nevertheless, both methods were adequately sensitive for real wine analysis, yielding highly comparable IBMP concentrations of 26.1 and 27.8 ng/L, respectively, from a Sauvignon blanc wine. The complexity of the real wine headspace was simplified as a result of selective detection using GC x GC-NPD and, in the case of GC x GC-IDTOFMS, the use of extracted ion chromatograms (EICs).

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“…Thiol specific analytical methods have been developed to extract selectively and to determine quantitatively these ultratrace compounds in wine (11,16,17). Although these methods were powerful in obtaining purified extracts of these compounds, their major drawback was that the internal standard, 4-methoxy-2-methyl-2-mercaptobutane, a tertiary aliphatic thiol and ether, was only partially functionally similar to the target compounds, which does not allow an accurate quantification (18)(19)(20), especially in the case of such reactive compounds (21)(22)(23). Indeed, 2 and 3 were secondary thiols and, in addition, primary alcohol and acetate, respectively, while the tertiary thiol 1 was also a ketone; as a result, their physicochemical properties were different from those of the internal standard.…”

Section: Introductionmentioning

confidence: 99%

“…Conversely, a stable isotopomer of the analyte is widely recognized to be preferable to even a close homologue, as the physicochemical properties of the labeled analogue are very close to those of the analyte. Thus, a stable isotope dilution assay (SIDA) is the method that provides the closest approach yet to a definitive method, as discussed previously in review articles (19,20), and would be the most accurate method for the quantification of these trace odorants. Such a method, using [ 13 C 4 ]-1 and GC-MS in the chemical ionization mode with methane, was developed for the quantification of 1 in Scheurebe and Gewu ¨rztraminer wines, but its limitations were not explicitly discussed (24).…”

Section: Introductionmentioning

confidence: 99%

Quantitative Determination of Sulfur-Containing Wine Odorants at Sub Parts per Billion Levels. 2. Development and Application of a Stable Isotope Dilution Assay

Schneider

Kotseridis

Ray

et al. 2003

J. Agric. Food Chem.

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[(2)H(10)]-4-Mercapto-4-methylpentan-2-one (d(10)-1), [(2)H(2)]-3-mercaptohexan-1-ol (d(2)-2), and [(2)H(5)]-3-mercaptohex-1-yl acetate (d(5)-3), deuterated analogues of impact odorants of wines, were used to determine quantitatively the natural compounds in white wines (Muscadet, Sauvignon, and Bacchus) with a stable isotope dilution assay using gas chromatography coupled either with ion trap tandem mass spectrometry (GC-ITMS-MS) or with atomic emission detection monitored on sulfur-selective acquisition (GC-AED). The thiol compounds were recovered from wines by liquid-liquid extraction, then purified from the wine extracts by covalent chromatography, and analyzed. The quantitative determination of 4-mercapto-4-methylpentan-2-one 1 in the wines that were analyzed was performed better with GC-AED than with GC-ITMS-MS under the conditions that were used. However, the detection limit of the method was higher than the odor threshold of 4-mercapto-4-methylpentan-2-one 1 in wine (5 vs 0.8 ng/L). The levels of this compound in the Sauvignon and Bacchus wines were much higher than its odor threshold, but it was not detectable in the Muscadet wines. On the contrary, GC-ITMS-MS was much more sensitive than GC-AED for detection of 3-mercaptohexan-1-ol 2 and 3-mercaptohex-1-yl acetate 3, and the detection limits were much lower than their odor thresholds in wine. The former compound was detected in all of the Muscadet wines that were analyzed at levels always higher than its odor detection threshold, while the latter occurred at levels higher than its odor threshold in only one Muscadet wine.

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Stable Isotope Dilution Gas Chromatography-Mass Spectrometry for Determination of Methoxypyrazines (“Green” Aroma) in Wine

Cited by 9 publications

References 33 publications

Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3- methoxypyrazine pheromones in ladybugs

Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3- methoxypyrazine pheromones in ladybugs

Analysis of methoxypyrazines in wine using headspace solid phase microextraction with isotope dilution and comprehensive two‐dimensional gas chromatography

Quantitative Determination of Sulfur-Containing Wine Odorants at Sub Parts per Billion Levels. 2. Development and Application of a Stable Isotope Dilution Assay

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