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Flavor of Traditional Chinese Liquor By IDENTIFICATION OF COMPOUNDS RESPONSIBLE FOR THE CHARACTERISTIC “SOY SAUCE” FLAVOR OF TRADITIONAL CHINESE LIQUOR BY WENQI ZHU DISSERTATION Submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Food Science and Human Nutrition in the Graduate College of the University of Illinois at Urbana-Champaign, 2018 Urbana, Illinois Doctoral Committee: Professor Hao Feng, Chair Professor Keith R. Cadwallader, Director of Research Professor Michael J. Miller Dr. Dawn M. Bohn I Abstract Soy sauce aroma liquor is one of the most popular types of traditional liquors in China, with the annual commercial value as high as 8.2 billion USD. The most famous soy sauce aroma liquor is the Chinese national liquor Moutai (MT), which was first developed around 206 BC. The flavor of MT is unique and highly appreciated by both experts and consumers. It received gold awards at the 1915 San Francisco “World's Fair” and at the 12th International Food Fair in Paris in 1986, which is testimony to the outstanding flavor and premium quality of this liquor product. However, significant as it is economically and culturally to China, knowledge about the characteristic flavor profile of MT is quite limited. Many scientists have studied this topic for decades and raised several hypotheses with respect to the compounds that are responsible for MT’s unique and characterizing flavor. However, despite much effort the compounds actually responsible for the characterizing “soy sauce” aroma of soy sauce aroma liquors are still unknown. The lack of this information has hindered the optimization of the brewing and blending technology to achieve liquors with better and more consistent aroma profiles. This research aims to identify the key and characterizing odorants in soy sauce aroma liquor in the case of MT. Through the use of advanced separation and analytical methods, 143 odor-active components were detected. The relative potencies of the odorants were assessed by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). Based on the results of AEDA, the most potent odorants in MT were: acetal; ethyl 2-methylpropanoate; ethyl butanoate; ethyl 2-methylbutanoate; ethyl 3-methylbutanoate; ethyl pentanoate; ethyl 2- methylpentanoate; ethyl 4-methylpentanoate; isopentyl hexanoate; β-damascenone and ethyl phenylpropionate, 2-phenylethanol, 3-methybutanal, 2-methyl-3-furanthiol, 2-methyl-3- (methyldithio)furan, dimethyl trisulfide and 3-hydroxy-4,5-hydroxy-2(5H)-furanone (sotolon). Four sulfur-containing odorants which might provide “savory” top notes to the flavor of MT were identified as 2-methyl-3-furanthiol (MFT), 2-methyl-3-(methyldithio)furan (MFT-MT), 2- furfurylthiol, and bis(2-methyl-3-furyl) disulfide (MFT-MFT). To the best of our knowledge, MFT, MFT-MT and MFT-MFT have not been previously identified in Moutai or any other type of Chinese soy sauce aroma liquor. II Thirty-nine of the selected potent odorants were quantitated or semi-quantitated in MT. Among these, 35 were determined by stable isotope dilution analysis (SIDA)-gas chromatography-mass spectrometry (GC-MS). The concentration of each odorant was used for the calculation of its odor activity value (OAV; ratio of the concentration of an odorant to its odor detection threshold). Based on the flavor dilution (FD) factors from AEDA and OAVs, 36 potent odorants were selected for construction of an aroma recombinant model of MT. The model was created by adding 36 high purity standards at appropriate concentrations to matrix consisting of 53% alcohol by volume (ABV). Triangle difference tests were performed using 24 sensory panelists for the purpose of determining whether the aroma recombinant model differed in terms of overall aroma from the original MT liquor. According to the results, among 48 judgements, 19 answers were correct, which indicated that the aroma model and the original liquor product did not differ significantly (P ≤ 0.05). Thus, these selected 36 odorants in the concentration determined in this study provide the typical aroma of the soy sauce aroma liquor MT. This project provides a better understanding of the complex flavor chemistry system of Moutai. Some important are the odorants are identified herein for the first time, including several with very low odor detection thresholds which contribute savory, meaty and beefy top notes to the overall aroma profile of Moutai. The aroma recombination model achieved through this project was proven to have no detectable aroma difference from the original liquor, which indicates that the essential characteristic odorants responsible for Moutai-flavor were successfully identified and accurately quantitated. III Acknowledgements First and foremost I would like to express my sincerest gratitude to my advisor Dr. Keith R. Cadwallader to offer me the opportunity to pursue my PhD program under his guidance. I am always proud of being a member of Cadwallader group. Thank you for your invaluable advice and enormous support in this project. I would like to thank my committee members Dr. Hao Feng, Dr. Michael J. Miller and Dr. Dawn Bohn for their time, effort, support and willingness to serve on my committee. Thanks to my parents Professor Xiaojun Zhu and Professor Chunfang Liang for their great encouragement and support throughout this process. Thanks to all my lab mates for their help, patience and understanding. IV Table of Contents Chapter 1: Introduction......................................................................................................1 Chapter 2: Literature Review.............................................................................................9 Chapter 3: Identification of Potent Odor-Active Components in Moutai.........................22 Chapter 4: A Streamlined Approach for Careful and Exhaustive Aroma Characterization of Aged Liquors...................................................................53 Chapter 5: Quantitation of Selected Potent Odorants in Moutai.......................................88 Chapter 6: Sensory Studies of an Aroma Recombination Model of Moutai....................103 Chapter 7: Aroma Chemistry of Moutai: Summary and Future Recommendations........109 V Chapter 1: Introduction Flavor is the integrated and nearly simultaneous response to the perception of taste, aroma and somatosensory (nerve) stimuli present in the oral and nasal cavities, generally as a consequence of the consumption of a food or beverage1. Although the peripheral sensory organs involved in the detection of taste and smell stimuli are distinct, their signals are integrated in the orbitofrontal and other areas of the cerebral cortex of the brain to generate the perception of “flavor”2. Most flavor researchers agree that in most instances olfaction (aroma or odor) plays the predominant and characterizing role in food flavor quality, including recognition and overall food acceptance 3. This is true in the case of most distilled spirits, and especially for the traditional Chinese liquors including the soy sauce aroma liquors which are highly aromatic. The various types of distilled beverages and liquors produced worldwide involve the use of different fermentation technologies, including use of different cultures, substrates, distillation methods and aging practices. These processes are often highly developed and sometimes even prescribed or regulated across the different types of spirts to achieve a consistent and characteristic flavor for each type of spirit. The potent odorants responsible for the unique flavor of a spirit or liquor are mainly derived through the fermentation and aging processes and sometimes even directly from the substrate materials. The flavor of most spirits is caused by the volatile odor-active substances; however, in some cases, e.g. whiskies, some taste-active components are extracted from the containers (e.g. oak) used for aging the spirit. Traditional Chinese distilled liquors (baijiu) differ from wood-aged spirits because they are usually aged in pottery. For this reason, the extraction or generation of taste-active components in baijiu is quite limited. That said, baijiu is not totally devoid of non-volatile substances. For example, lichenysin, a cyclooctapeptide produced by Bacillus licheniformis, can modulate the aroma-profile of some baijius by selectively changing the partitioning of the odorants via hydrogen bonding4,5. The various kinds baijius are roughly classified into 12 groups based on their typical or expected flavor attributes, which include: soy sauce aroma liquors (Moutai flavor liquors), strong aroma liquors (Luzhou-flavor liquors), Fen-flavor liquors, rice-flavor liquors, mixed-flavor liquors, Feng-flavor liquors, Fuyu-flavor liquors, Dong-flavor liquors, site-flavor liquors, Yubingshao- 1 flavor liquors, sesame-flavor liquors and Laobaigan-flavor liquors6. The grouping of these liquors is largely based on their unique and distinguishing flavors. This is possible because each baijiu type possesses a unique set of potent odorants which determines its characteristic flavor. For instance, ethyl hexanoate is the main characterizing odorant of strong aroma liquors, while ethyl acetate is responsible for the characteristic flavor of Fen-flavor liquors7 and methional and ethyl hexanoate are important for the characteristic flavor of sesame flavor liquors8. Due to the limitation of expertise and technology in flavor chemistry research, not all of the 12 types of Baijiu are chemically defined with respect to their characterizing
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