Comparison of Potent Odorants in Traditional and Modern types of Chinese Xiaoqu Liquor (Baijiu) Based on Odor Activity Values and Multivariate Analyses

Predominant odorants in modern and traditional types of Chinese xiaoqu liquor (Baijiu) were identified and compared by the combined use of gas chromatography−olfactometry, odor activity values (OAVs), and multivariate analyses. A total of 79 aroma compounds were identified in a typical modern type xiaoqu Baijiu (M) and a typical traditional type xiaoqu Baijiu (T), 42 of them had OAV > 1 in both M and T samples. The main differences between the two samples were obtained for the concentration of 23 aroma-active compounds. A total of 22 samples made by different brewing processes were analyzed to confirm the differences. Partial least squares discriminant analysis confirmed that 20 compounds could be used as potential markers for discrimination between modern type xiaoqu Baijiu and traditional type xiaoqu Baijiu. Their difference in content is between 1.5 and 17.9 times for modern type xiaoqu Baijiu and traditional type xiaoqu Baijiu. The results showed the aroma characteristics of modern and traditional type xiaoqu Baijiu clearly and comprehensively, which will provide guidance for modern Baijiu quality control and evaluation.

Identification of Rotundone as an Important Contributor to the Flavor of Oak-Aged Spirits

Experiments were conducted to identify a compound responsible for a spicy, woody, incense-like odor note in oak-aged spirits. The target compound was extracted from oak wood and various oak-aged spirits and analyzed by multidimensional (heart-cut) gas chromatography–mass spectrometry–olfactometry (MD–GC–MS–O), and was unambiguously identified as the sesquiterpene ketone, 5-isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexadydro-1(2H)-azulenone (rotundone). Quantitation of the trace-level target compound was done by stable isotope dilution analysis (SIDA) in a variety of oak-aged spirits, including bourbon, rye, Tennessee whiskey, scotch, rum, and tequila. The content of rotundone was found to increase as a function of years of barrel aging for 4-, 8-, and 12-year-old bourbons obtained from the same manufacturer, thus confirming its origin to be from oak. In addition, odor-activity values (OAVs) were compared for selected potent odorants, including rotundone, in the same 4-, 8-, and 12-year-old bourbons, which indicated the relative importance of rotundone in the overall flavor of oak-aged spirits.

Characterization of the Key Aroma Compounds in the Fruit of Litsea pungens Hemsl. (LPH) by GC-MS/O, OAV, and Sensory Techniques

The key aroma compounds in the fruit of Litsea pungens Hemsl. (LPH) were concentrated through solvent-assisted flavor evaporation (SAFE) and characterized by gas chromatography-mass spectrometry-olfactometry (GC-MS/O), quantitative descriptive analysis (QDA), odor activity values (OAVs), and addition test. The results showed that LPH contained 31 aroma-active compounds (flavor dilution, FD = 9). Among them, 30 odorants were quantified by the standard curve method. The OAV analysis results showed that 25 odorants had OAVs ≥ 1, which could be considered as the potent odorants. D-Limonene and 3,7-dimethyl-2,6-octadienal had the highest OAVs (OAV = 9803 and 8399), followed by (Z)-3,7-dimethylocta-2,6-dienal (OAV = 1893), β-myrcene (OAV = 1798), (E)-3-phenyl-2-propenoic acid ethyl (OAV = 1603), and β-caryophyllene (OAV = 1129). Addition experiments further confirmed that 3,7-dimethyl-2,6-octadienal, (Z)-3,7-dimethylocta-2,6-dienal, and D-limonene contributed to lemon attribute, β-myrcene contributed to green attribute, citronellal contributed to mint and fresh note, and eucalyptol contributed to eucalyptus-like note were the key odorants.

Characterization of the Key Aroma Compounds in Traditional Hunan Smoke-Cured Pork Leg (Larou, THSL) by Aroma Extract Dilution Analysis (AEDA), Odor Activity Value (OAV), and Sensory Evaluation Experiments

The key aroma compounds in smoke-cured pork leg were characterized by gas chromatography–olfactometry coupled with aroma extract dilution analysis (GC–O/AEDA), odor activity value (OAV), recombination modeling, and omission tests. Ranking analysis showed that pork leg smoke-cured for 18 days had the best sensory qualities, with strong meaty, smoky, roasty, woody, and greasy attributes. Thirty-nine aroma-active regions with flavor dilution (FD) factors ranging from 9 to 6561 were detected. Overall, 3-ethylphenol had the highest FD factor of 6561, followed by 2,6-dimethoxyphenol, 3,4-dimethylphenol, 4-ethylguaiacol, 4-methylguaiacol, 3-methylphenol, and 2-acetyl-1-pyrroline, with FD ≥243. Among 39 aroma compounds, 27 compounds with OAVs ≥1 and were potent odorants. A similarity of 90.73% between the recombination model and traditional Hunan Smoke-cured Pork Leg (THSL) sample was obtained. Omission tests further confirmed that (E)-2-nonenal, 2-methoxy-4-vinylphenol, guaiacol, 3-ethylphenol, 2,6-dimethylphenol, 2-acetyl-1-pyrroline, and methional were key odorants in smoke-cured pork leg. Additionally, 2-acetyl-1-pyrroline (38.88 μg/kg), which contributes to a roasty aroma, was characterized here as a key odorant of smoke-cured pork leg for the first time.

Continuous-Flow Biocatalytic Process for the Synthesis of the Best Stereoisomers of the Commercial Fragrances Leather Cyclohexanol (4-Isopropylcyclohexanol) and Woody Acetate (4-(Tert-Butyl)Cyclohexyl Acetate)

Leather cyclohexanol (4-(isopropyl)cyclohexanol) and woody acetate (4-(tert-butyl)cyclohexyl acetate) are commercialized for functional perfumery applications as mixtures of cis- and trans-isomers. The cis-isomers are more potent odorants than the corresponding trans counterparts, but they are the less favoured products in most of the classical synthetic routes. Known stereoselective routes to cis-4-alkylcyclohexanols are characterized by a high environmental burden and/or troublesome reaction work-up. In this work, we examine the use of commercial alcohol dehydrogenases (ADHs) to produce cis-4-alkylcyclohexanols, including the two derivatives with isopropyl and tert-butyl substituents, by the stereoselective reduction of the corresponding ketones. High conversions and diastereoisomeric excess values were achieved with five of the eighteen tested ADHs. To complete the synthetic approach to woody acetate, Candida antarctica A (CALA) was employed as a catalyst for the enzymatic acetylation of cis-4-(tert-butyl)cyclohexanol. In order to provide a technological upgrade to the production of the most odorous isomers of the two commercial fragrances, we designed a continuous-flow process based on the combination of in-line enzymatic steps with in-line work-up, effectively providing samples of cis-leather cyclohexanol and cis-woody acetate with high diastereoisomeric purity.