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Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Flavours and Fragrances".

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 46394

Special Issue Editor

Prof. Dr. Michael C. Qian

E-Mail Website1 Website2
Guest Editor
Department of Food Science and Technology, Oregon State University, Corvallis, OR, USA
Interests: flavor chemistry; wine; volatile analysis; dairy science; GC-MS
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Dr. Gary Reineccius is a Professor Emeritus, from the Department of Food Science and Nutrition, University of Minnesota, St. Paul, Minnesota. He has been actively involved in flavor research since he began his MS graduate studies in 1964.

Dr. Reineccius is the world-renowned expert in flavor science. He received his Ph.D. from Pennsylvania State University in 1970 and started his academic career at the Unversity of Minnesota immediately after graduation as an assistant professor. During his tenure at the University of Minnesota, he advanced to a full professor in 1982 and later served separate terms as the Department head. Dr. Reneccius’s research expanded to a wide range of areas related to flavor chemistry, flavor analysis, flavor encapsulation, flavor application, and flavor technology. He has edited or co-edited four books and several book chapters, and authored over 240 research papers.

Dr. Reineccius is a great educator. He has taught the chemical and instrumental analysis of foods, food chemistry, food processing, as well as flavor chemistry and technology at the University of Minnesota to undergraduate and graduate students. He has graduated more than 70 MS and Ph.D. students, and many of them have become the leaders in the field of flavor science. Over his career, he has organized and/or contributed to numerous in-house flavor workshops including basic flavor systems, reaction flavors, encapsulation, analysis, applications, and off-flavors in foods. He contributed to many short courses sponsored by the American Association of Ceral Chemists, the American Chemical Society and the Institute of Food Technologist. He has trained numerous academic researchers and industrial scientists. He extended global outreach and taught flavor short courses at the University of Otago for eight years, the National University of Colombia, and Tecnas.

Dr. Gary Reneccius was the co-organizer of the First International Flavor and Fragrance Conference in Colombia, the Second International Flavor and Fragrance Conference in China, and the Third International Flavor and Fragrance Conference in Chile. He served as an Associate Editor for the Flavor and Fragrance Journal for 8 years and is a frequent reviewer for numerous journals.

Dr. Reineccius has spent sabbatical leaves with Fritzsche Dodge and Olcott (New York City, flavor creation and production), Nestle (Switzerland, process flavors), and Robertet S.A. (France, taste modifiers and manufacturing).

Dr. Reineccius has received numerous awards during his career. He has been granted the Palmer Award for his contribution to chromatography by the Minnesota Chromatography Forum. He was awarded as the honorary member of the Society of Flavor Chemists for his contribution to flavor science. He was presented the Stephen S. Chang Award by the Institute of Food Technologists for his contribution to advance flavor chemistry. FEMA (Flavor Extract Manufacturers Association) has given him their most coveted award for lifetime contributions to the flavor industry with an exceptional track record of discovery in the field of flavor science, including chemistry, biotechnology, analytical, and delivery. He has received the Distinguished Achievement and Service Award in Agricultural and Food Chemistry from the American Chemical Society, and become a Fellow by the American Chemical Society. He is also is the recipient of IFT’s Chicago Section Tanner Award and the Macy Award by the Minnesota Section of the IFT for his outstanding contributions to the development and industrial application of research in the food industry.

This Special Issue is dedicated to Professor Gary Reineccius for his lifetime contribution to flavor science and education. Original review articles and research papers related to flavor chemistry and biochemistry, flavor technology, flavor analysis, flavor perception will be collected to honor Dr. Reineccius.

Prof. Dr. Michael C. Qian *
Guest Editor

* Professor Michael C. Qian received his Ph.D. degree from the University of Minnesota advised by Dr. Gary Reineccius.

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Keywords

  • Flavor chemistry
  • Flavor technology
  • Flavor encapsulation
  • Aroma and flavor analysis
  • Aroma and flavor perception

Published Papers (16 papers)

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16 pages, 2959 KiB  
Article
Isolation, Characterization, and Compositional Analysis of Polysaccharides from Pinot Noir Wines: An Exploratory Study
by Danye Zhu, Armando Alcazar-Magana, Yan Ping Qian, Yongsheng Tao and Michael C. Qian
Molecules 2022, 27(23), 8330; https://doi.org/10.3390/molecules27238330 - 29 Nov 2022
Cited by 4 | Viewed by 1537
Abstract
It has been reported that polysaccharides in wine can interact with tannins and other wine components and modify the sensory properties of the wine. Unfortunately, the contribution of polysaccharides to wine quality is poorly understood, mainly due to their complicated structure and varied [...] Read more.
It has been reported that polysaccharides in wine can interact with tannins and other wine components and modify the sensory properties of the wine. Unfortunately, the contribution of polysaccharides to wine quality is poorly understood, mainly due to their complicated structure and varied composition. In addition, the composition and molecular structure of polysaccharides in different wines can vary greatly. In this study, the polysaccharides were isolated from pinot noir wine, then separated into high-molecular-weight (PNWP-H) and low-molecular-weight (PNWP-L) fractions using membrane-based ultrafiltration. Each polysaccharide fraction was further studied using size exclusion chromatography, UV–Vis, FT-IR, matrix-assisted laser desorption/ionization–high-resolution mass spectrometry, and gas chromatography-mass spectrometry (GC-MS). The results showed that PNWP-L and PNWP-H had different chemical properties and compositions. The FT-IR analysis showed that PNWPs were acidic polysaccharides with α- and β-type glycosidic linkages. PNWP-L and PNWP-H had different α- and β-type glycosidic linkage structures. FT-IR showed stronger antisymmetric and symmetric stretching vibrations of carboxylate anions of uronic acids in PNWP-L, suggesting more uronic acid in PNWP-L. The size exclusion chromatography results showed that over 72% of the PNWP-H fraction had molecular sizes from 25 kDa to 670 kDa. Only a small percentage of smaller molecular polysaccharides was found in the PNWP-H fraction. In comparison, all of the polysaccharides in the PNWP-L fraction were below 25 KDa, with a majority distributed approximately 6 kDa (95.1%). GC-MS sugar composition analysis showed that PNWP-L was mainly composed of galacturonic acid, rhamnose, galactose, and arabinose, while PNWP-H was mainly composed of mannose, arabinose, and galactose. The molecular size distribution and sugar composition analysis suggested that the PNWP-L primarily consisted of rhamnogalacturonans and polysaccharides rich in arabinose and galactose (PRAG). In comparison, PNWP-H were mostly mannoproteins and polysaccharides rich in arabinose and galactose (PRAG). Further research is needed to understand the impacts of these fractions on wine organoleptic properties. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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11 pages, 1170 KiB  
Article
Optimization of Jinhua Ham Classification Method Based on Volatile Flavor Substances and Determination of Key Odor Biomarkers
by Ying Xu, Mengzhu Shui, Da Chen, Xiaozhong Ma and Tao Feng
Molecules 2022, 27(20), 7087; https://doi.org/10.3390/molecules27207087 - 20 Oct 2022
Cited by 9 | Viewed by 1535
Abstract
Jinhua ham is a traditional cured meat food in China. For a long time, its grade has mainly been evaluated by the human nose through the three-sticks method, which is highly subjective and is not conducive to establishing evaluation standards through odor markers. [...] Read more.
Jinhua ham is a traditional cured meat food in China. For a long time, its grade has mainly been evaluated by the human nose through the three-sticks method, which is highly subjective and is not conducive to establishing evaluation standards through odor markers. In this paper, we analyzed the well-graded Grade I–III hams provided by Jinzi Ham Co., Ltd. (Jinhua, China). Firstly, we used different extraction fibers, extraction temperatures, and extraction time to determine the optimal conditions for headspace solid-phase microextraction (HS-SPME). Then, the aroma components of Jinhua ham were analyzed by headspace solid-phase microextraction combined with gas chromatography–mass spectrometry (GC–MS), and OAV was calculated to screen the key aroma volatiles of three kinds of Jinhua ham. It was found that a total of 56 components were detected in the three types of ham. Among them, there are 21 kinds of key aroma volatiles. Aldehydes, alcohols, and acids are the three main components of Jinhua ham, and the content of aldehydes gradually decreases from Grade I to Grade III ham. The content of acids gradually increased, and we speculated that the increase in acid content was caused by the proliferation of microorganisms in Grade III ham. The key flavor volatiles in Grade I hams was hexanal and 2-methylbutanal. Grade I hams had a strong meat aroma, pleasant fatty, and roasted aroma without any off-flavors. In Grade II ham, the characteristic volatiles (E,E)-2,4-decadienal and ethyl isovalerate were detected. These two volatiles contribute greatly to the flavor of Grade II ham, which makes the flavor of Grade II ham have a special fruity aroma. They also may be prone to sourness and affect the flavor of the ham. Volatiles with low threshold values, such as pyrazines, furans, and sulfur-containing compounds, were relatively high in Grade III hams. This may also contribute to the poorer flavor quality of Grade III hams. This experiment provided a reliable test method and evaluation basis for the rating of Jinhua ham. These results have positive implications for the establishment of odor markers-based grading criteria. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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16 pages, 2295 KiB  
Article
Composition of Pinot Noir Wine from Grapevine Red Blotch Disease-Infected Vines Managed with Exogenous Abscisic Acid Applications
by Ling Huang, Armando Alcazar Magana, Patricia A. Skinkis, James Osborne, Yanping L. Qian and Michael C. Qian
Molecules 2022, 27(14), 4520; https://doi.org/10.3390/molecules27144520 - 15 Jul 2022
Cited by 1 | Viewed by 1703
Abstract
Grapevine red blotch disease (GRBD) has negative effects on grape development and impacts berry ripening. Abscisic acid (ABA) is a plant growth regulator involved in the initiation of berry ripening. Exogenous abscisic acid application was compared to an unsprayed control on GRBD-positive Pinot [...] Read more.
Grapevine red blotch disease (GRBD) has negative effects on grape development and impacts berry ripening. Abscisic acid (ABA) is a plant growth regulator involved in the initiation of berry ripening. Exogenous abscisic acid application was compared to an unsprayed control on GRBD-positive Pinot noir vines during two vintages, and the total monomeric anthocyanin, total phenolics, phenolic composition, and volatile profile were measured in wines. In addition, untargeted metabolites were profiled using high-resolution LC-MS/MS. Results showed that the wine composition varied by vintage year and was not consistent with ABA application. Wines from the ABA treatment had a lower total anthocyanin and total phenolic content in one year. The untargeted high-resolution LC-MS/MS analysis showed a higher abundance of phenolic compounds in ABA wines in 2019, but lower in 2018. The wine volatile compounds of ABA treatments varied by vintage. There were higher levels of free β-damascenone, β-ionone, nerol, and several fermentation-derived esters, acids, and alcohols in ABA wines, but these were not observed in 2019. Lower 3-isobutyl-2-methoxypyrazine (IBMP) was also observed in wines with ABA treatment in 2019. The results demonstrated that ABA application to the fruit zones did not consistently mitigate the adverse impacts of GRBD on Pinot noir wines. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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15 pages, 1277 KiB  
Article
Odor Characteristics of Novel Non-Canonical Terpenes
by Svenja Sommer, Leon M. Lang, Laura Drummond, Markus Buchhaupt, Marco A. Fraatz and Holger Zorn
Molecules 2022, 27(12), 3827; https://doi.org/10.3390/molecules27123827 - 14 Jun 2022
Cited by 3 | Viewed by 2073
Abstract
Several non-canonical, methylated terpenes have been described as products of genetically modified Escherichia coli recently, and the aroma properties of 28 odor-active methylated derivatives of prenol, isoprenol, bornane, camphene, carene, citronellol, fenchol, geraniol, limonene, linalool, terpineol, and farnesol were characterized for the first [...] Read more.
Several non-canonical, methylated terpenes have been described as products of genetically modified Escherichia coli recently, and the aroma properties of 28 odor-active methylated derivatives of prenol, isoprenol, bornane, camphene, carene, citronellol, fenchol, geraniol, limonene, linalool, terpineol, and farnesol were characterized for the first time in the current study. Twelve methylated monoterpenes exhibited a particularly intense and pleasant odor and were therefore chosen for the determination of their respective odor thresholds (OTs) in comparison to their non-methylated equivalents. In addition to the determination of OTs based on the literature value for the internal standard, (2E)-decenal, the threshold values of the compounds with individually determined OTs of the participants were calculated. This enabled a more precise identification of the OTs. Among the non-canonical terpenes, the lowest OTs in the air were found for 2-methyllinalool (flowery, 1.8 ng L−1), 2-methyl-α-fenchol (moldy, 3.6 ng L−1), 2-methylgeraniol (flowery, 5.4 ng L−1), 2-methylcitronellol (citrus-like, 7.2 ng L−1), and 4-methylgeraniol (citrus-like, 16 ng L−1). The derivatives of geraniol, linalool, and citronellol showed very pleasant odor impressions, which could make them interesting for use as flavoring agents in the flavor and fragrance industry. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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19 pages, 634 KiB  
Article
The Effects of Antioxidants on the Changes in Volatile Compounds in Heated Welsh Onions (Allium fistulosum L.) during Storage
by Sang Mi Lee, Dami Kim and Young-Suk Kim
Molecules 2022, 27(9), 2674; https://doi.org/10.3390/molecules27092674 - 21 Apr 2022
Cited by 3 | Viewed by 1299
Abstract
Welsh onion (Allium fistulosum L.) is usually used to enhance the flavor characteristics of various foods. Volatile compounds in Welsh onions, including sulfur-containing compounds, may vary during heat process and storage. Accordingly, the changes in the volatile compounds in Welsh onions, subjected [...] Read more.
Welsh onion (Allium fistulosum L.) is usually used to enhance the flavor characteristics of various foods. Volatile compounds in Welsh onions, including sulfur-containing compounds, may vary during heat process and storage. Accordingly, the changes in the volatile compounds in Welsh onions, subjected to heat and antioxidant (ascorbic acid and glutathione) treatments during storage, are investigated in the present study. The majority of sulfur-containing compounds in Welsh onions showed significant differences between the untreated Welsh onions and heated Welsh onions. During the heating of the Welsh onions, some sulfur-containing compounds, such as 2-methylthiirane, 1-(methyldisulfanyl)prop-1-ene, 1-[[(E)-prop-1-enyl]disulfanyl]propane, 1-(propyltrisulfanyl)propane, 1-[[(E)-prop-1-enyl]trisulfanyl]propane, and (methyltetrasulfanyl)methane, showed significant differences between the untreated and heated Welsh onions (p < 0.05). In addition, partial least square discriminant analysis (PLS-DA) was applied to discriminate the heated Welsh onion samples added with different antioxidants. The heated Welsh onion samples added with ascorbic acid was mainly associated with 2-phenylacetaldehyde, acetic acid, methylsulfanylmethane, prop-2-ene-1-thiol, undecan-2-one, and (2E,4E)-deca-2,4-dienal. Moreover, the key volatile compounds in the heated Welsh onion samples added with glutathione were 3-ethylthiophene, 1-(methyldisulfanyl)-1-methylsulfanylpropane, 1-methylsulfanylpentane, 2-prop-2-enylsulfanylpropane, and 1-propan-2-ylsulfanylbutane. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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16 pages, 2238 KiB  
Article
Free Amino Acids and Volatile Aroma Compounds in Watermelon Rind, Flesh, and Three Rind-Flesh Juices
by Xiaofen Du, Mindy Davila, Jessica Ramirez and Cierra Williams
Molecules 2022, 27(8), 2536; https://doi.org/10.3390/molecules27082536 - 14 Apr 2022
Cited by 9 | Viewed by 2408
Abstract
Watermelon rind is treated as agricultural waste, causing biomass loss and environmental issues. This study aimed to identify free amino acids and volatiles in watermelon rind, flesh, and rind-flesh juice blends with ratios of 10%, 20%, and 30%. Among the 16 free amino [...] Read more.
Watermelon rind is treated as agricultural waste, causing biomass loss and environmental issues. This study aimed to identify free amino acids and volatiles in watermelon rind, flesh, and rind-flesh juice blends with ratios of 10%, 20%, and 30%. Among the 16 free amino acids quantified, watermelon rind alone contained higher total amino acids (165 mg/100 g fresh weight) compared to flesh alone (146 mg/100 g). The rind had significantly higher (1.5×) and dominant amounts of citrulline and arginine (61.4 and 53.8 mg/100 g, respectively) than flesh. The rind, however, contained significantly lower amounts of essential amino acids. Volatile analysis showed that watermelon rind total volatiles (peak area) comprised only 15% of the flesh volatiles. Of the 126 volatiles identified, the rind alone contained 77 compounds; 56 of these presented in all five samples. Aldehydes and alcohols were most prevalent, accounting for >80% of the total volatiles in all samples. Nine-carbon aldehyde and alcohol compounds dominated both the flesh and rind, though the rind lacked the diversity of other aldehydes, alcohols, ketones, terpenes, terpenoids, esters and lactones that were more abundant in the watermelon flesh. Watermelon rind was characterized by the major aroma compounds above their thresholds, including 17 aldehydes and six unsaturated nine-carbon alcohols. This study demonstrated the potential for rind as a food or beverage supplement due to its key features such as concentrated citrulline and arginine, relatively low odor intensity, and valuable volatiles associated with fresh, green, cucumber-like aromas. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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16 pages, 1310 KiB  
Article
Identification of Non-Volatile Compounds Generated during Storage That Impact Flavor Stability of Ready-to-Drink Coffee
by Hao Lin, Edisson Tello, Christopher T. Simons and Devin G. Peterson
Molecules 2022, 27(7), 2120; https://doi.org/10.3390/molecules27072120 - 25 Mar 2022
Cited by 7 | Viewed by 2914
Abstract
Coffee brew flavor is known to degrade during storage. Untargeted and targeted LC/MS flavoromics analysis was applied to identify chemical compounds generated during storage that impacted the flavor stability of ready-to-drink (RTD) coffee. MS chemical profiles for sixteen RTD coffee samples stored for [...] Read more.
Coffee brew flavor is known to degrade during storage. Untargeted and targeted LC/MS flavoromics analysis was applied to identify chemical compounds generated during storage that impacted the flavor stability of ready-to-drink (RTD) coffee. MS chemical profiles for sixteen RTD coffee samples stored for 0, 1, 2, and 4 months at 30 °C were modeled against the sensory degree of difference (DOD) scores by orthogonal partial least squares (OPLS) with good fit and predictive ability. Five highly predictive untargeted chemical features positively correlated to DOD were subsequently identified as 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3-O-feruloylquinic acid, and 5-O-feruloylquinic acid. The increase in the six acidic compounds during storage was confirmed by sensory recombination tests to significantly impact the flavor stability of RTD coffee during storage. A decrease in pH, rather than an increase in total acidity, was supported to impact the coffee flavor profile. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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10 pages, 3225 KiB  
Article
Encapsulation of Orange Oil Using Fluidized Bed Granulation
by Gary Reineccius, Shardul Patil and Vaidhyanathan Anantharamkrishnan
Molecules 2022, 27(6), 1854; https://doi.org/10.3390/molecules27061854 - 12 Mar 2022
Cited by 6 | Viewed by 2097
Abstract
The primary objective of this research is to determine how granulation compares to spray drying/agglomeration for producing larger, more dense flavoring particles. Granulation can yield large, dense particles and thereby negate the need for a two-step process (spray drying followed by agglomeration) to [...] Read more.
The primary objective of this research is to determine how granulation compares to spray drying/agglomeration for producing larger, more dense flavoring particles. Granulation can yield large, dense particles and thereby negate the need for a two-step process (spray drying followed by agglomeration) to achieve improved flow/handling properties of dry flavorings. In this study, a 55% solids slurry (blend of OSAn-modified starch and maltodextrin 15DE) was prepared and then single-fold orange peel oil was added at 20 or 25% of the carrier solids level. The 20% flavoring emulsion was spray dried (SD), and a portion of the resultant powder then agglomerated (Agg) in a bottom spray, fluidized bed. A second emulsion of the same carrier composition but using 25% orange oil based on carrier solids was prepared and subjected to fluidized bed granulation (FBG). Particle size, density, orange oil retention and oxidative stability on storage were determined. Overall, it is observed during this study that FBG produces orange oil encapsulates that possess better properties, such as more resistance to oxidation, a better retention of orange oil and a higher density than SD or SD/Agg powders. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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10 pages, 1655 KiB  
Article
Mechanisms of Rebaudioside A Degradation and Ingredient-Sweetener Interactions in Beverages during Storage
by Benjamin S. Gelinas, Edisson Tello and Devin G. Peterson
Molecules 2022, 27(4), 1385; https://doi.org/10.3390/molecules27041385 - 18 Feb 2022
Viewed by 1659
Abstract
The instability of rebaudioside A (Reb A) in food product applications during storage challenges their utilization. The pathways of Reb A degradation in aged acidic beverages were investigated. Three Reb A degradation compounds of known sensory importance were monitored, consisting of (1 [...] Read more.
The instability of rebaudioside A (Reb A) in food product applications during storage challenges their utilization. The pathways of Reb A degradation in aged acidic beverages were investigated. Three Reb A degradation compounds of known sensory importance were monitored, consisting of (1) a rearrangement, (2) a hydration, and (3) an epoxidation/rearrangement product. Using deuterium-labeled water (D2O) experiments, compounds 1–2 were reported to be generated by acid-catalyzed mechanisms involving the formation of a carbocation on carbon position 16, followed by either deprotonation via E1 elimination on C15 to form the more thermodynamically stable trisubstituted alkene (compound 1), or by the Markovnikov addition of water via SN1 substitution to form a tertiary alcohol (compound 2). Compound 3 was generated by epoxidation of the exomethylene at the C16–17 positions, followed by the opening and rearrangement of the ring to form a new alkene bond between C15–C16 and a primary alcohol on C17. Further analysis of the effect of beverage ingredients indicated the addition of caramel color significantly increased (p < 0.0001) the concentrations of compounds 1–2 compared to the aged control by 89 and 83%, respectively, whereas a specific coffee flavor and caramel color were reported to significantly reduce (p < 0.0001) the formation of compound 3 compared to the aged control during storage by 90 and 79%, respectively. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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13 pages, 2106 KiB  
Article
Volatile Analysis of Wuliangye Baijiu by LiChrolut EN SPE Fractionation Coupled with Comprehensive GC×GC-TOFMS
by Jia Zheng, Zhanglan He, Kangzhuo Yang, Zhipeng Liu, Dong Zhao and Michael C. Qian
Molecules 2022, 27(4), 1318; https://doi.org/10.3390/molecules27041318 - 15 Feb 2022
Cited by 9 | Viewed by 2543
Abstract
Wuliangye baijiu is one of the most famous Chinese liquors with a protected geographical indication. This study used LiChrolut® EN-based solid-phase extraction (SPE) and fractionation combined with comprehensive two-dimensional chromatography-time-of-flight mass spectrometry (GC×GC-TOFMS) to unveil its volatile composition. The volatiles were isolated [...] Read more.
Wuliangye baijiu is one of the most famous Chinese liquors with a protected geographical indication. This study used LiChrolut® EN-based solid-phase extraction (SPE) and fractionation combined with comprehensive two-dimensional chromatography-time-of-flight mass spectrometry (GC×GC-TOFMS) to unveil its volatile composition. The volatiles were isolated with LiChrolut® EN-based SPE and traditional liquid-liquid extraction (LLE). The neutral/basic fractions from LLE and the SPE were fractionated on a LiChrolut® EN SPE column and analyzed by comprehensive GC×GC-TOFMS. Compared with LLE, more esters and alcohols were detected in the SPE-based extraction. The SPE fractionation and GC×GC-TOFMS analysis resulted in the identification of about 500 volatile compounds in more than 3000 peaks of the Wuliangye baijiu. The approach simplifies the complex baijiu composition into functional group-based fractions for reliable identification and analysis. This study provided a confidence volatile identification approach for Chinese baijiu based on the SPE fractionation GC×GC-TOFMS. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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12 pages, 1061 KiB  
Article
Characterization of Volatile Compounds of Rosa roxburghii Tratt by Gas Chromatography-Olfactometry, Quantitative Measurements, Odor Activity Value, and Aroma Intensity
by Yunwei Niu, Ruolin Wang, Zuobing Xiao, Xiaoxin Sun, Pinpin Wang, Jiancai Zhu and Xueying Cao
Molecules 2021, 26(20), 6202; https://doi.org/10.3390/molecules26206202 - 14 Oct 2021
Cited by 7 | Viewed by 1779
Abstract
Rosa roxburghii tratt (RRT), widely distributed in the southwest of China, is favored by consumers for its good taste and healthy functions. In this study, thirty-seven compounds of Rosa roxburghii Tratt (RRT) were identified and quantified by gas chromatography–olfactometry (G–O) and gas chromatography–mass [...] Read more.
Rosa roxburghii tratt (RRT), widely distributed in the southwest of China, is favored by consumers for its good taste and healthy functions. In this study, thirty-seven compounds of Rosa roxburghii Tratt (RRT) were identified and quantified by gas chromatography–olfactometry (G–O) and gas chromatography–mass spectrometry (GC–MS) analysis. Furthermore, ethyl 2-methylpropanoate, ethyl butanoate, ethyl 2-methylbutyrate, and ethyl hexanoate were present with much higher odor activity values (OAVs) than other compounds. The key notes were confirmed by omission tests. Possible interaction among key notes was investigated through odor intensity determination and sensory analysis. It showed fruity and woody notes had synergistic effects. Full factorial design was used to evaluate the notes contribution to the whole odor. One important finding is the major effect of order interactions, fruity note (X1) and woody note (X4) especially, emphasizing the existence of complex interactions occurring between odor notes. The interaction X1X4 was further investigated. The woody note has a positive effect when the fruity note is also in the mixture but tends to show a negative effect otherwise. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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16 pages, 1498 KiB  
Article
Tandem Solid-Phase Extraction Columns for Simultaneous Aroma Extraction and Fractionation of Wuliangye and Other Baijiu
by Zhanglan He, Kangzhuo Yang, Zhipeng Liu, Mingzhe An, Zongwei Qiao, Dong Zhao, Jia Zheng and Michael C. Qian
Molecules 2021, 26(19), 6030; https://doi.org/10.3390/molecules26196030 - 04 Oct 2021
Cited by 4 | Viewed by 2406
Abstract
Wuliangye baijiu is one of the most famous baijiu in China, with a rich, harmonic aroma profile highly appreciated by consumers. Thousands of volatiles have been identified for the unique aroma profile. Among them, fatty acid esters have been identified as the main [...] Read more.
Wuliangye baijiu is one of the most famous baijiu in China, with a rich, harmonic aroma profile highly appreciated by consumers. Thousands of volatiles have been identified for the unique aroma profile. Among them, fatty acid esters have been identified as the main contributors to the aroma profile. In addition, many non-ester minor compounds, many of which are more polar than the esters, have been identified to contribute to the characteristic aroma unique to Wuliangye baijiu. The analysis of these minor compounds has been challenging due to the dominance of esters in the sample. Thus, it is desirable to fractionate the aroma extract into subgroups based on functional group or polarity to simplify the analysis. This study attempts a new approach to achieve simultaneous volatile extraction and fractionation using tandem LiChrolut EN and silica gel solid-phase extraction (SPE) columns. A baijiu sample (10 mL, diluted in 40 mL of water) was first passed through the LiChrolut EN (1.0 g) column. The loaded LiChrolut EN column was then dried with air and coupled with a silica gel (5.0 g) SPE column with anhydrous Na2SO4 (10.0 g) in between. The volatile compounds were eluted from the LiChrolut EN column and simultaneously fractionated on the silica gel column based on polarity. The simultaneous extraction and fractionation technique enabled the fractionations of all fatty acid esters into less polar fractions. Fatty acids, alcohols, pyrazines, furans, phenols, hydroxy esters, and other polar compounds were collected in more polar fractions. This technique was used to study the volatile compounds in Wuliangye, Moutai, and Fengjiu baijiu. In addition to fatty acid esters, many minor polar compounds, including 2,6-dimethylpyrazine, 2-ethyl-6-methylpyrazine, 2-ethyl-3,5-dimethylpyrazine, p-cresol, and 2-acetylpyrrole, were unequivocally identified in the samples. The procedure is fast and straightforward, with low solvent consumption. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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18 pages, 1078 KiB  
Article
Characterization of Aroma Compounds in Cooked Sorghum Using Comprehensive Two-Dimensional Gas Chromatography-Time-of-Flight Mass Spectrometry and Gas Chromatography-Olfactometry-Mass Spectrometry
by Shuang Chen, Li Wang, Derang Ni, Lin Lin, Heyu Wang and Yan Xu
Molecules 2021, 26(16), 4796; https://doi.org/10.3390/molecules26164796 - 07 Aug 2021
Cited by 5 | Viewed by 2642
Abstract
Sorghum is the major raw material for the production of Chinese Baijiu (Chinese liquor) and has a great effect on the flavor of Baijiu. Volatiles in cooked glutinous and non-glutinous sorghum samples were extracted using solid-phase microextraction (SPME) and analyzed via comprehensive two-dimensional [...] Read more.
Sorghum is the major raw material for the production of Chinese Baijiu (Chinese liquor) and has a great effect on the flavor of Baijiu. Volatiles in cooked glutinous and non-glutinous sorghum samples were extracted using solid-phase microextraction (SPME) and analyzed via comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC×GC-TOFMS) and gas chromatography-olfactometry/mass spectrometry (GC-O/MS). A total of 145 volatile compounds and 52 potent odorant compounds were identified from both sorghum types according to the retention index, MS, aroma, and standards. Based on their aroma features, the compounds were grouped into eight general categories, and the intensities of each aroma group were summed. Moreover, most of the compounds detected in the cooked sorghums were also detected in commercial Chinese Baijiu, indicating that the aroma compounds produced during the sorghum cooking process have a direct and significant influence on the final flavor quality of Baijiu. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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15 pages, 314 KiB  
Article
Identification of Rotundone as an Important Contributor to the Flavor of Oak-Aged Spirits
by Elizabeth Genthner-Kreger and Keith R. Cadwallader
Molecules 2021, 26(14), 4368; https://doi.org/10.3390/molecules26144368 - 20 Jul 2021
Cited by 7 | Viewed by 2735
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)

Review

Jump to: Research

16 pages, 1521 KiB  
Review
Role of Lipids in Food Flavor Generation
by Fereidoon Shahidi and Abul Hossain
Molecules 2022, 27(15), 5014; https://doi.org/10.3390/molecules27155014 - 06 Aug 2022
Cited by 91 | Viewed by 10009
Abstract
Lipids in food are a source of essential fatty acids and also play a crucial role in flavor and off-flavor development. Lipids contribute to food flavor generation due to their degradation to volatile compounds during food processing, heating/cooking, and storage and/or interactions with [...] Read more.
Lipids in food are a source of essential fatty acids and also play a crucial role in flavor and off-flavor development. Lipids contribute to food flavor generation due to their degradation to volatile compounds during food processing, heating/cooking, and storage and/or interactions with other constituents developed from the Maillard reaction and Strecker degradation, among others. The degradation of lipids mainly occurs via autoxidation, photooxidation, and enzymatic oxidation, which produce a myriad of volatile compounds. The oxidation of unsaturated fatty acids generates hydroperoxides that then further break down to odor-active volatile secondary lipid oxidation products including aldehydes, alcohols, and ketones. In this contribution, a summary of the most relevant and recent findings on the production of volatile compounds from lipid degradation and Maillard reactions and their interaction has been compiled and discussed. In particular, the effects of processing such as cooking, drying, and fermentation as well as the storage of lipid-based foods on flavor generation are briefly discussed. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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16 pages, 2095 KiB  
Review
Key Aspects of Amadori Rearrangement Products as Future Food Additives
by Yue Luo, Shiming Li and Chi-Tang Ho
Molecules 2021, 26(14), 4314; https://doi.org/10.3390/molecules26144314 - 16 Jul 2021
Cited by 24 | Viewed by 4956
Abstract
Flavor is one of the most important factors in attracting consumers and maximizing food quality, and the Maillard reaction (MR) is highly-involved in flavor formation. However, Maillard reaction products have a big drawback in their relatively low stability in thermal treatment and storage. [...] Read more.
Flavor is one of the most important factors in attracting consumers and maximizing food quality, and the Maillard reaction (MR) is highly-involved in flavor formation. However, Maillard reaction products have a big drawback in their relatively low stability in thermal treatment and storage. Amadori rearrangement products (ARPs), MR intermediates, can alternatively act as potential flavor additives for their better stability and fresh flavor formation ability. This review aims to elucidate key aspects of ARPs’ future application as flavorings. The development of current analytical technologies enables the precise characterization of ARPs, while advanced preparation methods such as synthesis, separation and drying processes can increase the yield of ARPs to up to 95%. The stability of ARPs is influenced by their chemical nature, pH value, temperature, water activity and food matrix. ARPs are associated with umami and kokumi taste enhancing effects, and the flavor formation is related to amino acids/peptides of the ARPs. Peptide-ARPs can generate peptide-specific flavors, such as: 1,6-dimethy-2(1H)-pyrazinone, 1,5-dimethy-2(1H)-pyrazinone, and 1,5,6-trimethy-2(1H)-pyrazinone. However, further research on systematic stability and toxicology are needed. Full article
(This article belongs to the Special Issue Flavor Chemistry and Technology: A Themed Issue in Honor of Professor Gary A. Reineccius)
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