Quantitative analysis of 3-alkyl-2-methoxypyrazines in juice and wine using stable isotope labelled internal standard assay

Kotseridis, Yorgos; Spink, M.; Brindle, Ian D.; Blake, Amy J.; Sears, M. K.; Chen, X.; Soleas, George J.; Inglis, Debra; Pickering, Gary J.

doi:10.1016/j.chroma.2008.02.088

Cited by 62 publications

(64 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Settling of the juice before fermentation can lead to a decrease in methoxypyrazine concentrations (Kotseridis et al, 2008), while concentrations have been reported to remain stable during fermentation (Sala et al, 2004). The compounds are generally resilient to standard wine fining practices (Pickering et al, 2006), and concentrations did not differ when exposed to various ageing conditions, such as light exposure and temperature variations (Blake et al, 2010).…”

Section: Methoxypyrazinesmentioning

confidence: 99%

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Coetzee

Toit

2015

SAJEV

View full text Add to dashboard Cite

Oxidation and the capacity for sufficient ageing potential of white wines are constant problems for winemakers worldwide. In general, it is accepted that certain grape varieties are especially sensitive to oxidation, suggesting that some of the chemical components key to their sensory attributes are strongly modulated by oxygen exposure. Sauvignon blanc is a well-documented example of an oxygen-sensitive wine, and understanding the stability of various compounds is crucial in order to preserve the fresh and fruity characters of Sauvignon blanc wines while preventing the formation of off-odours over a long period of time. Compounds such as the volatile thiols and methoxypyrazines are key aroma compounds responsible for the typical Sauvignon blanc aroma, while other aroma compounds, such as esters, alcohols and acids, can also contribute to the wine aroma. Oxidation-related compounds (such as aldehydes) can occur under certain conditions and it is essential to understand the chemistry behind oxidation to control and manage the development of various characteristics in wine. The sensory interactions occurring between various compounds (both aromatic and non-aromatic) are also important due to enhancing or suppressive effects that can mask certain aroma nuances. This review focuses on the stability of certain compounds of Sauvignon blanc wines during oxidation and ageing and how it affects the aromatic and non-aromatic composition of these wines. ABBREVIATIONS

show abstract

Section: Methoxypyrazinesmentioning

confidence: 99%

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Coetzee

Toit

2015

SAJEV

View full text Add to dashboard Cite

show abstract

“…The grape maturity at the harvest and sunlight exposure is the main factor affecting the levels of MPs in wines. Even though IBMP is generally more abundant than IPMP and SBMP in grapes and wine, high IPMP concentrations are also considered undesirable in most wines and have been described as having a 'pea-asparagus' type aroma (Kotseridis et al 2008).…”

mentioning

confidence: 99%

Methoxypyrazines in Sauvignon blanc wines, detection of addition of artificial aroma

Rajchl¹,

Čížková²,

Voldřich³

et al. 2009

Czech J. Food Sci.

View full text Add to dashboard Cite

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.

show abstract

“…The pattern of the other signals of d 3 -4b is comparable and in accordance with published data. 11,12,20 In the 13 C-NMR spectra of compound 3b and of commercial MP 4b (Figure S-2), the signal of the heteroatom bound methyl group is shifted about 16 ppm from 37.3 ppm in 3b to 53.3 ppm in 4b. The positions of this methyl groups were unambiguously assigned by heteronuclear correlation NMR ( 3 and S-4).…”

Section: Resultsmentioning

confidence: 95%

“…The reaction of these 2-chloro derivatives with ethanolic sodium ethoxide, forming the ethyl ethers (ethoxypyrazines) has also been described in this early work and was used in subsequent studies for the synthesis of various 2-alkoxy-3-alkylpyrazines. [9][10][11][12] . Buttery and co-workers used an alternative approach for converting the preliminary hydroxypyrazines to 2-methoxy-3-alkylpyrazines 4 by derivatization with diazomethane 2,13 ( Figure 1, route B).…”

Section: Introductionmentioning

confidence: 99%

New insights into the synthesis and characterization of 2‐methoxy‐3‐alkylpyrazines and their deuterated isotopologues

Schmarr

Sang

Ganss

et al. 2011

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

A previously described synthetic route for preparation of 2-methoxy-3-alkylprazines (MPs) based on condensation of glyoxal with an a-amino acid amide, followed by methylation with iodomethane yields 3-alkyl-1-methyl-1H-pyrazin-2-ones (N-methyl derivatives), rather than the designated 2-methoxy-3-alkylpyrazines (O-methyl derivatives). Despite similar nuclear magnetic resonance and mass spectral properties, gas chromatographic (GC) retention indices differ significantly, indicating chemical difference. With the example of 3-sec-butyl-1-methyl-1H-pyrazin-2-one and its 3-sec-butyl-1-[ 2 H 3 ]methyl-1H-pyrazin-2-one isotopologue, the position of the methyl group introduced could be assigned unambiguously, using heteronuclear multiple bond correlation (HMBC) NMR experiments. For future characterization, the spectroscopic (NMR, EI 1 MS) as well as GC retention index data on two stationary phases of the most aroma relevant MPs and their deuterated isotopologues are summarized.

show abstract

Quantitative analysis of 3-alkyl-2-methoxypyrazines in juice and wine using stable isotope labelled internal standard assay

Cited by 62 publications

References 25 publications

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Methoxypyrazines in Sauvignon blanc wines, detection of addition of artificial aroma

New insights into the synthesis and characterization of 2‐methoxy‐3‐alkylpyrazines and their deuterated isotopologues

Contact Info

Product

Resources

About