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

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.

[1]  Baoguo Sun,et al.  Flavor mystery of Chinese traditional fermented baijiu: The great contribution of ester compounds. , 2021, Food chemistry.

[2]  A. Bula,et al.  Selection, Sizing, and Modeling of a Trickle Bed Reactor to Produce 1,2 Propanediol from Biodiesel Glycerol Residue , 2021, Processes.

[3]  A. Kondo,et al.  Metabolic engineering of 1,2-propanediol production from cellobiose using beta-glucosidase-expressing E. coli. , 2021, Bioresource technology.

[4]  C. Ribeiro,et al.  Separation of Enantiomers Using Gas Chromatography: Application in Forensic Toxicology, Food and Environmental Analysis , 2020, Critical reviews in analytical chemistry.

[5]  Rong Zhang,et al.  Recent advances in Baijiu analysis by chromatography based technology-A review. , 2020, Food chemistry.

[6]  K. Engel Chirality- an important phenomenon regarding biosynthesis, perception and authenticity of flavour compounds. , 2020, Journal of agricultural and food chemistry.

[7]  A. Cifuentes,et al.  Chiral analysis in food science , 2020 .

[8]  Yan Xu,et al.  Characterization of Potent Odorants Causing a Pickle-like Off-Odor in Moutai-Aroma Type Baijiu by Comparative Aroma Extract Dilution Analysis, Quantitative Measurements, Aroma Addition and Omission Studies. , 2020, Journal of agricultural and food chemistry.

[9]  Yulin Zhou,et al.  Characterisation of volatile compounds in Maotai flavour liquor during fermentation and distillation , 2019, Journal of the Institute of Brewing.

[10]  W. Niu,et al.  Metabolic engineering of Escherichia coli for the de novo stereospecific biosynthesis of 1,2-propanediol through lactic acid , 2018, Metabolic engineering communications.

[11]  M. Pinto,et al.  Enantiomeric ratios: Why so many notations? , 2018, Journal of chromatography. A.

[12]  Baoguo Sun,et al.  Effect of Fermentation Processing on the Flavor of Baijiu. , 2018, Journal of agricultural and food chemistry.

[13]  H. Aboul‐Enein,et al.  Multidimensional Gas Chromatography for Chiral Analysis , 2018, Critical reviews in analytical chemistry.

[14]  D. Jeffery,et al.  Chiral analysis of 3-sulfanylhexan-1-ol and 3-sulfanylhexyl acetate in wine by high-performance liquid chromatography-tandem mass spectrometry. , 2018, Analytica chimica acta.

[15]  O. Lasekan Enantiomeric differentiation of three key volatile compounds in three different palm wines (Elaeis guineensis, Borassus flabellifer and Nypa fruticans) , 2018 .

[16]  S. Tempère,et al.  2-Methylbutyl acetate in wines: Enantiomeric distribution and sensory impact on red wine fruity aroma. , 2017, Food chemistry.

[17]  Guangyuan Jin,et al.  Mystery behind Chinese liquor fermentation , 2017 .

[18]  Jianxue Liu,et al.  Characterization of Aromatic Liquor by Gas Chromatography and Principal Component Analysis , 2017 .

[19]  Chaosheng Zhang,et al.  The geographical patterns of Chinese liquors during 1995–2004 , 2017 .

[20]  Baoguo Sun,et al.  The brewing process and microbial diversity of strong flavour Chinese spirits: a review , 2017 .

[21]  B. Han,et al.  Baijiu (白酒), Chinese liquor: History, classification and manufacture , 2016 .

[22]  U. Fischer,et al.  Enantiodifferentiation of 1,2-propanediol in various wines as phenylboronate ester with multidimensional gas chromatography-mass spectrometry , 2016, Analytical and Bioanalytical Chemistry.

[23]  P. Schieberle,et al.  Quantitation and Enantiomeric Ratios of Aroma Compounds Formed by an Ehrlich Degradation of l-Isoleucine in Fermented Foods. , 2016, Journal of agricultural and food chemistry.

[24]  Fangming Jin,et al.  Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO , 2016 .

[25]  D. Dubourdieu,et al.  How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers. , 2015, Analytica chimica acta.

[26]  Baoguo Sun,et al.  Enantioselective syntheses and sensory properties of 2-methyl-tetrahydrofuran-3-thiol acetates. , 2015, Journal of agricultural and food chemistry.

[27]  S. Fanali,et al.  Chiral separations in food analysis , 2013 .

[28]  G. Flores,et al.  Stereodifferentiation of some chiral aroma compounds in wine using solid phase microextraction and multidimensional gas chromatography , 2010 .

[29]  D. Dubourdieu,et al.  Distribution and organoleptic impact of sotolon enantiomers in dry white wines. , 2008, Journal of agricultural and food chemistry.

[30]  S. Ebeler Enantiomeric analysis as a tool for authentication of foods and beverages , 2007 .

[31]  D. Dubourdieu,et al.  Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (Var. Sauvignon Blanc and Semillon). , 2006, Journal of agricultural and food chemistry.

[32]  P. Stremple,et al.  Gas Chromatographic Analysis of Chiral Aroma Compounds in Wine Using Modified Cyclodextrin Stationary Phases and Solid Phase Microextraction , 2001 .

[33]  G. de Revel,et al.  Contribution to the knowledge of malolactic fermentation influence on wine aroma. , 1999, Journal of agricultural and food chemistry.

[34]  K. Kikuchi,et al.  Determination of enantiomers of 1,2-propanediol in beer by gas chromatography , 1997 .

[35]  R. Marchelli,et al.  The potential of enantioselective analysis as a quality control tool , 1996 .

[36]  Helmut Schütz,et al.  Anaerobic Reduction of Glycerol to Propanediol-1.3 by Lactobacillus brevis and Lactobacillus buchneri , 1984 .

[37]  H. Onishi,et al.  Aerobic Dissimilation of l-Rhamnose and the Production of l-Rhamnonic Acid and 1,2-Propanediol by Yeasts , 1968 .