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. 2022 Aug 26;11(17):2584.
doi: 10.3390/foods11172584.

Determination of 2-Pentanol Enantiomers via Chiral GC-MS and Its Sensory Evaluation in Baijiu

Lisha Hu  1 , Shuyi Qiu  1 , Yifeng Dai  1   2 , Luqin Tian  1 , Chaoyang Wei  1
Affiliations

Determination of 2-Pentanol Enantiomers via Chiral GC-MS and Its Sensory Evaluation in Baijiu

Lisha Hu et al. Foods. .

Abstract

The enantiomeric contents of 2-pentanol of Baijiu were analyzed by liquid-liquid extraction (LLE) coupled with gas chromatography-mass spectrometry (GC-MS) using β-cyclodextrin as a chiral stationary phase. In this study, the average enantiomeric ratios R:S were 72:28, 64:36, and 94:6 in soy sauce aroma-type Baijiu (SSB), strong aroma-type Baijiu (STB), and light aroma-type Baijiu (LTB), respectively, and only (R)- configuration was found in rice aroma-type Baijiu (RTB). The highest enantiomeric concentration of 2-pentanol was found in STB. (R)-2-pentanol dominated in 48 Baijiu studied, and the concentration of (R)-2-pentanol was higher than that of the (S)-configuration. The results showed that the enantiomers of 2-pentanol were discrepant in different aroma types of Baijiu, and it may be the result of differences in raw materials, environment, and production processes. The 2-pentanol enantiomers had different odor characteristics, with different olfactory thresholds in pure water and 46% ethanol solutions by sensory analysis. (R)-2-pentanol was described as paint, rubber, grease, while the (S)-form had mint, plastic, and pungent notes. The olfactory thresholds of (R)- and (S)-form were 163.30 mg/L and 78.58 mg/L in 46% ethanol and 12.62 mg/L and 3.03 mg/L in pure water, respectively. The different enantiomeric distribution and aroma characteristics of the 2-pentanol enantiomers in Baijiu could be a potential marker for determining adulteration.

Keywords: 2-pentanol; Baijiu; chirality; enantiomer; sensory analysis.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
(a) (R)-2-Pentanol (CAS No. 31087-44-2), (b) (S)-2-Pentanol (CAS No. 26184-62-3).
Figure 2
Figure 2
Chromatograms of 2-pentanol racemate separated by different chiral chromatographic columns (a): Beta DEX™ 120, (b): Astec CHIRADEXL® B-TA, (c): Astec CHIRALDEX™ B-DM, (d): Astec CHIRALDEX® G-TA, (e): CYCLOSIL-B, (f): HP-CHIRAL-20B, (g): MEGA-DEX DAC Beta, (h): MEGA-DEX DET Beta.
Figure 3
Figure 3
Enantiomeric separation chromatograms of 2-pentanol in representative Baijiu samples of different aroma types using LLE (a): SSB, (b): STB, (c): LTB, (d): RTB.
Figure 4
Figure 4
(a): 2-pentanol enantiomers concentration heat map, (b): Double y-axis box line plot (Red coordinates were (R)-2-pentanol, blue coordinates were (S)-2-pentanol) of 2-pentanol isomer concentration using LLE, (c): Double y-axis box line plot of 2-pentanol enantiomeric ratio using LLE, (d) Box Line plot of 2-pentanol enantiomer content in MT43 and LJ, (e) Box Line plot of 2-pentanol enantiomer content in DK, YHMZL, and WLY.
See this image and copyright information in PMC

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