Gas Chromatographic Analysis of Chiral Aroma Compounds in Wine Using Modified Cyclodextrin Stationary Phases and Solid Phase Microextraction

Ebeler, Susan E.; Vickers, Allen K.; Stremple, Phil

doi:10.1021/bk-2001-0794.ch005

Cited by 5 publications

(6 citation statements)

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“…The utilisation of SPME in the study of fruit flavour19–21 and in the enantiomeric analysis of chiral compounds22, 23 has been previously described in the literature. However, the determination of blackcurrant volatile components by SPME has not been reported so far.…”

Section: Introductionmentioning

confidence: 99%

Varietal differences in terpene composition of blackcurrant (Ribes nigrum L) berries by solid phase microextraction/gas chromatography

Castillo¹,

Dobson²

2002

J Sci Food Agric

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Relative amounts of volatile terpenes in berries of 10 different blackcurrant (Ribes nigrum L) cultivars were examined by solid phase microextraction/gas chromatography (SPME/GC). The optimisation of a variety of parameters affecting SPME enabled relative standard deviations from three replicates ranging from 2 to 12% to be achieved. Differences between cultivars in the proportions rather than in the qualitative composition of volatile terpenes were found, and the proportions of some terpenes were especially variable. Furthermore, the enantiomeric ratios of the chiral terpenes were determined for the first time in blackcurrant berries by GC using a column with a stationary phase containing permethylated cyclodextrin (Chirasil-b-Dex). The enantiomeric compositions of the majority of the chiral terpenes varied within a reasonably narrow range. However, the levels of two monoterpene alcohols, terpinen-4-ol and linalool, exhibited considerable variations amongst cultivars.

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Section: Introductionmentioning

confidence: 99%

Varietal differences in terpene composition of blackcurrant (Ribes nigrum L) berries by solid phase microextraction/gas chromatography

Castillo¹,

Dobson²

2002

J Sci Food Agric

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“…As far as we know, more than 40 chiral compounds have been investigated in alcoholic beverages, including five alcohols, such as 2,3-butanediol [ 19 , 20 ], 2-methyl-1-butanol [ 21 , 22 ], 1-phenylethanol [ 23 ], 2-butanol [ 19 ], and 1,2-PG [ 18 ]. The 1,2-PG has an asymmetric chiral carbon atom with two different enantiomers (as in Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

“…As far as we know, more than 40 chiral compounds have been inves alcoholic beverages, including five alcohols, such as 2,3-butanediol [19,20], 2 butanol [21,22], 1-phenylethanol [23], 2-butanol [19], and 1,2-PG [18]. The 1,2asymmetric chiral carbon atom with two different enantiomers (as in Figure 1) a colorless viscous liquid with good chemical stability and various applicati polyol compound with certain hygroscopicity and is widely used as solvent, deicing agent, and humidifier in the food industry [24,25].…”

Section: Introductionmentioning

confidence: 99%

Distribution and Quantification of 1,2-Propylene Glycol Enantiomers in Baijiu

Dai

Qiu

et al. 2021

Foods

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Enantiomers of 1,2-Propylene glycol (1,2-PG) were investigated in 64 commercial Chinese Baijiu including soy sauce aroma-type Baijiu (SSB), strong aroma-type Baijiu (STB), and light aroma-type Baijiu (LTB), via chiral gas chromatography (β-cyclodextrin). The natural enantiomeric distribution and concentration of 1,2-PG in various baijiu were studied to evaluate whether the distribution and content of the two isomers of 1,2-PG were correlated with the aroma type and storage year. The results showed that 1,2-PG has a high enantiomeric ratio and the (S)-configuration predominated in SSB. The average S/R enantiomeric ratio of this compound in SSB was approximately 87:13 (±3.17), with an average concentration of 52.77 (±23.70) mg/L for the (S)-configuration and 8.72 (±3.63) mg/L for the (R)-enantiomer. The (R)-configuration was predominant in the STB, whereas neither (S) nor (R)-form of 1,2-PG were detected in LTB. The content of the two configurations of 1,2-PG in the JSHSJ vintage of SSB showed a wave variation, with an average S/R enantiomeric ratio of 89:11 (±1.15). The concentration of (R)-1,2-PG in XJCTJ vintage liquors showed an upward and then downward trend with aging time, with an overall downward trend, and the concentration of (S)-form showed a wavy change with an overall upward trend. Except for the LZLJ-2019 vintage where both (R) and (S)-1,2-PG were present, all other samples only existed (R)-form, and a decreasing trend of (R)-enantiomer with aging time was observed. The enantiomeric ratio of 1,2-PG might be one of the potential markers for adulteration control of Baijiu as industrial 1,2-PG usually presented in the racemic mixture. Sensory analysis revealed olfactory thresholds of 4.66 mg/L and 23.92 mg/L for the (R)- and (S)-configurations in pure water respectively. GC-O showed both enantiomers exhibited different aromatic nuances.

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“…These columns allowed for excellent separation of amino acids but had limited application for analysis of most volatile compounds. With the introduction of chiral cyclodextrin-based GC stationary phases in the late 1970s and 1980s, chemists were provided with the ability to directly separate a large number of underivatized chiral compounds [ 13 ]. For example, several early studies demonstrated separations of cyclic and acyclic enantiomers with a range of functional groups including lactones, terpene hydrocarbons, carbonyls, alcohols, spiroketals, and oxiranes [ 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Investigation of a Quantitative Method for the Analysis of Chiral Monoterpenes in White Wine by HS-SPME-MDGC-MS of Different Wine Matrices

2015

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A valid quantitative method for the analysis of chiral monoterpenes in white wine using head-space solid phase micro-extraction-MDGC-MS (HS-SPME-MDGC-MS) with stable isotope dilution analysis was established. Fifteen compounds: (S)-(−)-limonene, (R)-(+)-limonene, (+)-(2R,4S)-cis-rose oxide, (−)-(2S,4R)-cis-rose oxide, (−)-(2R,4R)-trans-rose oxide, (+)-(2S,4S)-cis-rose oxide, furanoid (+)-trans-linalool oxide, furanoid (−)-cis-linalool oxide, furanoid (−)-trans-linalool oxide, furanoid (+)-cis-linalool oxide, (−)-linalool, (+)-linalool, (−)-α-terpineol, (+)-α-terpineol and (R)-(+)-β-citronellol were quantified. Two calibration curves were plotted for different wine bases, with varying residual sugar content, and three calibration curves for each wine base were investigated during a single fiber’s lifetime. This was needed as both sugar content and fiber life impacted the quantification of the chiral terpenes. The chiral monoterpene content of six Pinot Gris wines and six Riesling wines was then analyzed using the verified method. ANOVA with Tukey multiple comparisons showed significant differences for each of the detected chiral compounds in all 12 wines. PCA score plots showed a clear separation between the Riesling and Pinot Gris wines. Riesling wines had greater number of chiral terpenes in comparison to Pinot Gris wines. Beyond total terpene content it is possible that the differences in chiral terpene content may be driving the aromatic differences in white wines.

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Gas Chromatographic Analysis of Chiral Aroma Compounds in Wine Using Modified Cyclodextrin Stationary Phases and Solid Phase Microextraction

Cited by 5 publications

References 0 publications

Varietal differences in terpene composition of blackcurrant (Ribes nigrum L) berries by solid phase microextraction/gas chromatography

Varietal differences in terpene composition of blackcurrant (Ribes nigrum L) berries by solid phase microextraction/gas chromatography

Distribution and Quantification of 1,2-Propylene Glycol Enantiomers in Baijiu

Investigation of a Quantitative Method for the Analysis of Chiral Monoterpenes in White Wine by HS-SPME-MDGC-MS of Different Wine Matrices

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