Ester Aroma Research Articles

Peanut Pairing Baijiu: To Enhance Retronasal Aroma Intensity while Reducing Baijiu Aftertaste.

Liquor-pairing food is a common dietary combination. Baijiu and peanuts are unquestionably a classic pairing in China. But no one has explained why. Its alteration in baijiu flavor was studied using multiple sensory evaluation, as well as nontargeted proton-transfer reaction mass spectrometry coupled with GC × GC-MS. Multiple statistical analyses were used to discover the changes in the retronasal aroma and its contribution to baijiu flavor. It showed that the consumption of peanuts enhances the burst intensity of ester aroma (0.814-1.00) and Jiao aroma (0.889-0.963) but decreases the aftertaste of baijiu (p < 0.05). Meanwhile, it increases the release intensity and advances the burst time of baijiu retronasal aroma (p < 0.05), suppressing its aftertaste through the retention effect of the food matrix, the changes in oral processing, and cross-modal interactions. Hydrophobicity, polarity, and chemical characteristics are key factors of the uneven impact of accompanying food to aroma compounds. Esters, especially ethyl caprylate (2103 ± 927 to 51.9 ± 4.05) is most impacted by peanuts and contributes most to baijiu flavor changes. Pyrazines from peanut enhance the Qu-aroma, grain aroma, and Chen aroma in baijiu flavor. Therefore, we revealed the chemical nature of baijiu-peanut combination and help to optimize baijiu consumption experience.

Methyl salicylate affects fruit quality and aroma compounds of cherry during cold storage

Cherries are easy to soften and rot during the period of storage. This work was performed to assess the impact of different concentrations of methyl salicylate (MeSA, 0.1 mmol·L−1, 1.0 mmol·L−1, 2.0 mmol·L−1) on fruit quality and aroma compounds of cherries (‘Meizao’ and ‘Labins’) during cold storage (0 °C). Results showed that 1.0 mmol·L−1 of MeSA had the greatest effect on decreasing the respiration rate, improving the firmness and maintaining the soluble solids content (SSC) of cherry fruits. The main volatile aroma compounds in ‘Meizao’ and ‘Labins’ cherries were benzyl alcohol, hexanal, trans-2-hexenal, benzaldehyde and 2-hexenal. Additional observations revealed that MeSA could increase the ester aroma compounds and delay the loss of alcohol, aldehyde, ketone and terpenoid aroma compounds in postharvest cherries. Therefore, MeSA could effectively improve the quality and inhibit aroma loss of cherry fruits during cold storage.

Effectiveness of sulfuric acid and hydrochloric acid catalysts in the esterification of frankincense cinnamic acid with ethanol and methanol

This research aims to compare the effectiveness of sulfuric acid and hydrochloric acid catalysts in the esterification of frankincense cinnamic acid (STYRAX paraleoncomud PERK). Esterification of sulfuric acid catalyst is carried out with ethanol and for hydrochloric acid catalyst with methanol. Esterification was carried out by refluxing a mixture of 1:20 cinnamic acid - ethanol and methanol, with 3 mL of each catalyst at a temperature of 60oC for one hour. The results were rinsed with 3 x 50 mL distilled water and dried with anhydrous sodium sulfate. The results were filtered and verified for functional groups using FTIR and composition analysis using GC – MS. The results of FTIR interpretation show a decrease in absorption intensity (-OH) at 3500 cm-1 as a functional group that reacts compared to the ester results as an indication of the ongoing esterification reaction. The resulting ethyl cinnamate has a high conversion of 84.42%. Methyl cinnamate also has a distinctive ester aroma but is clearer and based on GC-MS, the content of methyl cinnamate is relatively low, namely 34.40%, the remaining cinnamic acid is 37.28%, and various side products of 28.32%. Thus, the catalyst that provides better conversion is sulfuric acid, but it requires further purification by examining the appropriate absorbent and bleaching agent. The brown color of the ester product catalyzed by sulfuric acid is thought to occur due to the oxidation of the cinnamic acid double bond by the catalyst.

Jasmonate Promotes Ester Aroma Biosynthesis during Nanguo Pears Storage

Volatile organic compounds (VOCs) have been known to confer the flavor of fruits, characterizing the quality of fruits. Nanguo pear (Pyrus ussuriensis Maxim.) is widely popular among consumers due to its excellent ‘fruity’ aroma derived from ester aroma substances. Jasmonate (JAs) plays an indispensable role in the formation of many qualities in fruit. Therefore, the present study aimed to explore the effect of jasmonate on the VOCs in the Nanguo pear fruit during storage. During storage, the fruits were treated with various concentrations of methyl jasmonate (MeJA) and sodium diethyldithiocarbamate (DIECA, a JAs inhibitor), the inhibitors of JAs biosynthesis. Subsequently, the composition and levels of VOCs in the fruits were determined using GC-MS. The results showed that 100 uM MeJA treatment could promote the accumulation of ester aroma compounds in Nanguo pear fruits, while 100 mM DIECA had the opposite effect. Meantime, MeJA treatment significantly promoted peel degreening, soluble solids content (SSC), fruit softening, and ethylene formation. The RT-qPCR results showed that JAs stimulated the expression of PuAAT1 and repressed the expression of PuCXEs, leading to an increased accumulation of ester aroma compounds. Overall, these results provide a reference for further research on the effect of JAs on fruit aroma.

Inclusion complexes of β-cyclodextrin with isomeric ester aroma compounds: Preparation, characterization, mechanism study, and controlled release

Cyclodextrins (CDs) have been discovered to provide an efficient solution to the limited application of ester aroma molecules used in food, tobacco, and medication due to their strong smell and unstable storage. This work combined molecular modeling and experimental to analyze the conformation and controlled release of isomeric ester aroma compounds/β-CD inclusion complexes (ICs). The investigation revealed that ester aroma compounds could be effectively encapsulated within the β-CD cavity, forming ICs with low binding affinity. Furthermore, the key driving forces in ICs were identified as hydrogen bonds and van der Waals interactions through theoretical simulation. Results from the Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and Isothermal titration calorimetry (ITC) experiments confirmed the intermolecular interaction predicted by the molecular model. Notably, the release rate of aroma compounds from L-menthyl acetate/β-CD (LMA/β-CD) IC exceeded that of terpinyl acetate/β-CD (TA/β-CD) IC. This difference is attributed to the length of the chain of aroma molecules and the variation in the position of functional groups, influencing the stable formation of ICs with β-CD. These findings hold potential implications for refining the application of ICs across diverse industries.

Effects of yeast screened from traditional fermented milk on commercial fermented milk as adjunct flavor culture

Two yeast strains with better overall flavor quality were isolated and screened from traditional fermented milk in western Sichuan, identified as Kluyveromyces marxianus and Saccharomyces cerevisiae, and their role as adjunct cultures in fermented milk was studied. Fermented milk (LS, LSK, LSS and LSKS) were respectively inoculated with Lactobacillus bulgaricus + Streptococcus thermophiles (LS), LS + K. marxianus, LS + S. cerevisiae, and LS + K. marxianus + S. cerevisiae. The obtained LSKS has the best overall quality with moderate ethanol and ester aroma, rich in fermentation aroma, delicate taste, and the highest acidity (87.52 ± 0.44 °T), viscosity (418.18 ± 18.73 mPa·s), and organic acid content (449.736 mg/100 g), as well as the abundant ethyl esters (ethyl ocanoate, ethyl caprate, ethyl hexanoate). Non-targeted metabolomics revealed the metabolites differences for LSKS versus LS. Sixty-five metabolites upregulated and seventy-two metabolites downregulated, which were significantly enriched in arginine biosynthesis and glycerophospholipid metabolism pathway. A large number of short peptides were upregulated, and calenduloside G methyl ester has the potential to be used as a differential biomarker. This study provides a theoretical basis for the application potential of K. marxianus SY11 and S. cerevisiae SY32 to stimulate fermentation with LS as adjunct flavor cultures in commercial fermented milk.

Fermentation-promoting effect of three salt-tolerant Staphylococcus and their co-fermentation flavor characteristics with Zygosaccharomyces rouxii in soy sauce brewing

Staphylococcus is the dominant genus in the fermentation process of soy sauce, but its effect on the flavor of soy sauce has not been clearly established. In order to investigate the role of this genus in soy sauce fermentation, individual fermentation with Staphylococcus spp. screened from the moromi and their co-fermentation with an ester-producing yeast of Zygosaccharomyces rouxii were designed. Through the analysis of physicochemical properties, organic acid composition, volatile flavor compounds (VFCs) and sensory characteristics during fermentation, Staphylococcus was confirmed as a contributor to the acidity, ester aroma and alcohol aroma of soy sauce. In their co-fermentation with yeast, the ester aroma of soy sauce was further enhanced. Moreover, pathway enrichment analysis and network construction of key VFCs also revealed potential metabolic networks for formation of characteristic flavor compounds in co-fermentation. This work will help optimize the fermentation functional microbiota to obtain better soy sauce flavor.

Transcription factors MdMYC2 and MdMYB85 interact with ester aroma synthesis gene MdAAT1 in apple.

Volatile esters in apple (Malus domestica) fruit are the critical aroma components determining apple flavor quality. While the exact molecular regulatory mechanism remains unknown, jasmonic acid (JA) plays a crucial role in stimulating the synthesis of ester aromas in apples. In our study, we investigated the effects of methyl jasmonate (MeJA) on the production of ester aroma in apples. MeJA treatment significantly increased ester aroma synthesis, accompanied by the upregulation of several genes involved in the jasmonate pathway transduction. Specifically, expression of the gene MdMYC2, which encodes a transcription factor associated with the jasmonate pathway, and the R2R3-MYB transcription factor gene MdMYB85 increased upon MeJA treatment. Furthermore, the essential gene ALCOHOL ACYLTRANSFERASE 1 (MdAAT1), encoding an enzyme responsible for ester aroma synthesis, showed increased expression levels as well. Our investigation revealed that MdMYC2 and MdMYB85 directly interacted with the promoter region of MdAAT1, thereby enhancing its transcriptional activity. In addition, MdMYC2 and MdMYB85 directly bind their promoters and activate transcription. Notably, the interaction between MdMYC2 and MdMYB85 proteins further amplified the regulatory effect of MdMYB85 on MdMYC2 and MdAAT1, as well as that of MdMYC2 on MdMYB85 and MdAAT1. Collectively, our findings elucidate the role of the gene module consisting of MdMYC2, MdMYB85, and MdAAT1 in mediating the effects of JA and promoting ester aroma synthesis in apples.

A Thermodynamic and Kinetic Study on Electrochemical Esterification in Aroma-Enhanced Distilled Liquor (Baijiu)

The development of low-alcohol Baijiu is consistent with demand for the industry’s sustainable development. However, the ester aroma of low-alcohol Baijiu is insipid and unstable—mainly due to the hydrolysis of esters during shelf life—thus reducing the industry scale of low-alcohol Baijiu to a significantly small range. An electrochemical method for improving low-alcohol Baijiu’s ester concentration and stability was investigated from the aspects of thermodynamics and kinetics. The key finding is that the new Baijiu’s ester content obtained through distillation is relatively high, exceeding its content in the thermodynamic equilibrium state. Thus, the ester will be hydrolyzed during shelf life. The idea of applying electrochemical catalytic esterification technology to the production of low-alcohol Baijiu in this study is directly derived from the production practice of Baijiu factories; it provides a direction for the further optimization of low-alcohol Baijiu to facilitate the production of an alternative product that will contribute to public health.

Study on the Technology of Low Alcohol Hawthorn Flavor Beer

Hawthorn fruit is bright red in color, contains a variety of nutrients, and has many health effects. In this paper, through the study of yeast, fermentation temperature, acid reduction, high residual sugar and other factors, we finally selected NO303 Aerospace yeast with rich ester aroma and low fermentation degree reserved in the yeast bank of Qilu University of technology for fermentation. Fermentation temperature is 19.0℃, the main fermentation duration is:1-2days, total fermentation time is about 10 days. The physical and chemical indexes of low alcohol hawthorn beer are as follows: Original wort concentration is 11°P, residual sugar is 9.8°P, alcohol level is 0.45 %vol, total acid is 2.55mL/100mL, pH3.87, chroma is 13.5EBC. Finally, low alcohol hawthorn beer with light red color, hawthorn aroma and strong ester aroma was obtained. The beer has low acidity, balanced between acidity and sweetness, unique taste and low alcohol content. It is more like a carbonated beverage with strong killing taste and is suitable for the general public, especially young female consumers.

Characterization of aroma compounds and effects of amino acids on the release of esters in Laimao baijiu.

Laimao baijiu is a typical soy-sauce aroma-type baijiu in China. Amino acids are non-volatile compounds in baijiu and are beneficial to human health. Aroma is one of the important indicators that are used to evaluate the quality of baijiu. The interaction between aroma-active compounds and non-volatile compounds can also affect the release of aroma compounds. In this study, we identified the active-aroma compounds and amino acids in Laimao baijiu by stir bar sorptive extraction (SBSE), gas chromatography-olfactometry (GC-O), gas chromatography-mass spectrometry (GC-MS), and ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). The interaction between amino acids and key esters was investigated by sensory analysis and partition coefficients. A total of 63 aroma compounds and 21 amino acids were identified. Twenty-one esters were identified from them as major aroma-active ester compounds with odor activity values ≥ 1. Finally, sensory analysis revealed that l-alanine had a significant effect on the strength of the aromas of esters, suggesting that low concentrations of amino acids were more likely to promote the release of esters and high concentrations were more likely to inhibit this. The partition coefficient can be a good explanation for this phenomenon. l-Alanine can significantly affect the aroma intensity of key ester aroma compounds in Laimao baijiu, and the effects of different concentrations of amino acids are different. This work shows that amino acids, as non-volatile compounds, have a regulatory effect on the release of aroma compounds in alcoholic beverages, which may provide new technical support for the aroma modulation of alcoholic beverages. © 2022 Society of Chemical Industry.

Detection of the Freshness of Kiwifruit With a TD-GC-MS and a Gas-Sensing Array Based on the Surface-Acoustic-Wave Technique.

An electronic nose is an arrayed gas sensor mimicking the human olfactory system that can analyze and identify a flavour on collecting an odour from an environment. In our experiments, an electronic-nose system based on a surface acoustic wave (SAW) was used to measure the freshness of kiwifruit. 128° YX-LiNbO3 acted as a piezoelectric material; Au was deposited as an electrode and sensing area. With a polymer coating of various types on the sensing area and a connection to an oscillator circuit, a 113-114 MHz SAW was obtained. Depending on the properties of varied polymers, the frequency shift varied due to absorbed volatile organic compounds (VOC). In this way, with four surface-acoustic-wave sensors coated with varied polymers we built a kiwi-flavour database according to results from a TD-GC-MS system. When the concentration of esters increased, the kiwifruit began to ripen, accompanied by increased concentrations and types of VOC. As a result, polystyrene (PS) and fluoropolymer (CYTOP) polymers, which played the role of sensing materials, served as major materials to determine the ester aroma profile. Polyvinyl alcohol (PVA), polyvinyl butyral (PVB) and poly-N-vinylpyrrolidone (PNVP) were used to trap the alcohols and acids during a kiwifruit ripening period. This research proved that discrimination of differences is feasible from an unripe stage to a ripe stage and from a ripe stage to an over-ripe stage.

Comprehensive two-dimensional gas chromatography mass spectrometry-based untargeted metabolomics to clarify the dynamic variations in the volatile composition of Huangjiu of different ages.

Aging plays an important role in the formation of aroma characteristics of Huangjiu, a traditional Chinese alcoholic beverage. Comprehensive two-dimensional gas chromatography mass spectrometry (GC×GC-qMS)-based untargeted metabolomics combined with a multivariate analysis was used to investigate the dynamic variations in the aroma profile of Huangjiu during aging process and to establish the relationship between the changing volatile metabolite profiles and the age-dependent sensory attributes. A total of 144 volatile metabolites were identified by GC×GC-qMS and 63 were selected as critical metabolites based on variable importance in projection values and p-values. Based on the results of principal component analysis, orthogonal partial least-squares discriminant analysis, and hierarchical clustering analysis, the samples of six different ages were divided into three groups: 1Y and 3Y samples, 5Y and 8Y samples, and 10Y and 15Y samples. The partial least-squares analysis results further revealed the relationship between the aromas attributes and variations of these volatile compounds. The high esters, aldehydes, and lactones contents contributed to the high intensities of the sweet and ester aroma attributes of the aged Huangjiu, while the high alcohols and ethyl esters contents contributed to the alcoholic and fruity aroma attributes of the newly brewed Huangjiu. These results improve our understanding of the chemical nature of the aroma characteristics of aged Huangjiu. PRACTICAL APPLICATION: Huangjiu is often labeled with its age as a measure of quality, which influences consumers' choice. Dynamic variations in volatile compounds of Huangjiu during aging and its contribution to the aroma characteristics of Huangjiu were figured out, which will assist the industry to produce better quality aged Huangjiu for consumers.

Electrochemical esterification in distilled liquor via gold catalysis and its application for enhancing ester aroma of low-alcohol liquor

The development of low-alcohol liquor (Baijiu) can represent a tool to solve the problems of excessive alcohol intake. However, low-alcohol liquor has an insufficient ester aroma and a bland taste due to the alcohol dilution process. This study proposes an electrochemical catalysis technology to catalyze the esterification reaction between the acid and alcohol in liquor, thereby enhancing the ester aroma of low-alcohol liquor. In the electrochemical conversion process, the gold electrode with a certain potential promotes the formation of carbocation intermediate from corresponding carboxylic acid, thereby improving the esterification reaction efficiency. The key finding is that the total ester content of liquor treated using this technology is increased by more than 20%, and a strong ester aroma is attained. This study clarifies the electrocatalytic mechanism of the esterification reaction in liquor, and provides a new idea for making low-alcohol liquor become more attractive for aroma and taste aspects trying to obtain an alternative product contributing to the public health.

Screening Low-Ethanol Yeasts for Cider Production from a Perspective of Ester Aroma by Transcriptive Characterization

Screening Low-Ethanol Yeasts for Cider Production from a Perspective of Ester Aroma by Transcriptive Characterization

Influence of indigenous lactic acid bacteria on the volatile flavor profile of light-flavor Baijiu

Baijiu (Chinese liquor) is a type of traditional distilled spirit drink produced by spontaneous fermentation. Lactic acid bacteria as the predominant bacteria during the fermentation of Baijiu may influence the flavor through the production of enzymes and metabolites. Results showed that there was significant difference in lactic acid bacteria counts between different fermentation periods. Indigenous lactic acid bacteria with high alcohol tolerance and esterase activity were selected for fortified fermentation. Inoculation with indigenous lactic acid bacteria significantly changed the flavor profile of Baijiu. All the selected strains promoted the formation of ethyl acetate which is an important flavor in Baijiu. Lactobacillus acetotolerans significantly promoted the formation of ethyl acetate, ethyl lactate, ethanol, acetic acid, and 2,4-di-tert-butylphenol. Sensory analysis revealed higher harmony in the samples fermented with L. hilgardii and L. acetotolerans, and higher intensive ester aroma in the samples fermented with L. planturum. The generation of flavors such as esters, alcohols and acids were species or even strain dependent. The results of this work will broaden our knowledge regarding the role of indigenous lactic acid bacteria during Baijiu manufacturing, and provide a potential approach for improving the flavor of Baijiu.

Analysis of the postharvest storage characteristics of the new red-fleshed apple cultivar ‘meihong’

This study examined the effects of postharvest storage conditions on the fruit quality of a new red-fleshed apple cultivar (‘Meihong’). Mature ‘Meihong’ and ‘Golden delicious’ apples were exposed to room temperature, low temperature, and low temperature and 1-MCP, after which several fruit characteristics were evaluated (i.e., firmness, ethylene release rate, relative content of aroma components, phenolic compounds and antioxidant capacity, fruit softening-related enzyme activities, and related gene expression). Both ‘Meihong’ and ‘Golden delicious’ were ACS1-1/-2 heterozygotes, but the ethylene release rate in ‘Meihong’ fruits was lower than that in ‘Golden delicious’ fruits during storage. Therefore, ‘Meihong’ fruits are more conducive to storage. The low temperature storage with and without 1-MCP delayed fruit softening, decreased the ethylene release rate and ester aroma component content, and maintained total flavonoid and anthocyanin contents. Therefore, storage at low temperatures with 1-MCP or other preservatives may be useful for maintaining the ‘Meihong’ fruit quality.

Methyl jasmonate alleviates the reduced release of aroma‐related esters in ‘Nanguo’ pears by regulating ethylene biosynthesis and signal transduction

SummaryCryopreserved fruits usually develop symptoms, which affects the release of aroma. Our study investigated the impact of exogenous methyl jasmonate (MeJA) upon the synthesis of aromatic esters in ‘Nanguo’ pears after cold storage. It found that exogenous MeJA enhanced ethylene accumulation via improving the activity of 1‐aminocyclopropane‐1‐carboxylic‐acid (ACC) synthase (ACS) and ACC oxidase (ACO) and the expression levels of PuACS1 and PuACO1. After cryopreservation for 90 days, the ester aroma of ‘Nanguo’ pears was effectively improved by MeJA during normal temperature shelf life. In addition, the expression of PuERS1, PuETR1, PuEIN4, PuEIN2 and PuERF1 in MeJA‐treated fruits were obviously increased. Therefore, we infer that the influence of MeJA on production of aroma‐related esters in ‘Nanguo’ pears is closely connected with ethylene biosynthesis and signal transduction, namely increase activity of ACS and ACO, and upregulation of the expression level of PuACS1, PuACO1, PuERS1, PuETR1, PuEIN2, PuEIN4 and PuERF1.

Evaluation of Perceptual Interactions between Ester Aroma Components in Langjiu by GC-MS, GC-O, Sensory Analysis, and Vector Model.

The volatile compounds of three Langjiu (“Honghualangshi, HHL”, “Zhenpinlang, ZPL”, and “Langpailangjiu, LPLJ”) were studied by gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS). The results showed that a total of 31, 30, and 30 ester compounds making a contribution to aroma were present in the HHL, ZPL, and LPLJ samples, respectively. From these esters, 16 compounds were identified as important odour substances, and their odour activity values (OAVs) were greater than 1. The key ester components were selected as: ethyl acetate, ethyl 2-methylbutyrate, ethyl 3-methyl butyrate, ethyl hexanoate, and ethyl phenylacetate by aroma extract dilution analysis (AEDA), odour activity value (OAV), and omission testing. Five esters were studied for perceptual interactions while using Feller’s additive model, OAV, and a vector model. Among these mixtures, they all have an enhancing or synergistic effect. Among these mixtures, one mixture presented an additive effect and nine mixtures showed a synergistic effect.

Characterization of perceptual interactions among ester aroma compounds found in Chinese Moutai Baijiu by gas chromatography-olfactometry, odor Intensity, olfactory threshold and odor activity value.

Ester aroma compounds in Chinese Moutai Baijiu were extracted by liquid-liquid extraction (LLE) or headspace solid-phase microextraction (HS-SPME) and identified and quantified by gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS), and 13 of them were recognized as the important aroma compounds based on their flavor dilution (FD) values and odor activity values (OAVs). The perceptual interactions of ethyl isobutyrate and ethyl isovalerate for the overall esters aroma in 53% aqueous ethanol solution were studied through the odor intensity, olfactory threshold and OAV. The Vector Model showed that odor partial addition had occurred after mixing. The Feller's additive model and OAV analysis revealed that various concentrations of ethyl isobutyrate and ethyl isovalerate gave additive or synergistic odor effects for mixtures. In particular, as the concentration of ethyl isobutyrate was increased before mixing, the trend of increasing degree of interaction was observed in the mixture.