Ethyl Benzoate Research Articles

Synthesis and Characterization of Ester Derivatives of N-Phenylanthranilic Acid

N-Phenylanthranilic acid (fenamic acid) serves as the fundamental structure for synthesizing several non-steroidal anti-inflammatory drugs, antibacterial drugs and also functions as a modulator of membrane transport. To reduce the dose-related side effects of existing drugs, research is focussing to improve fenamic acid derivative solubility and bioavailability. A series of ester derivatives of N-phenylanthranilic acid (MB-1 to MB-5) viz. 2-(phenyl amino)methyl benzoate, 2-(phenyl amino)ethyl benzoate, 2-(phenyl amino)isopropyl benzoate,2-(phenyl amino)butyl benzoate and 2-(phenyl amino)phenyl benzoate were synthesized. The chemical structures and functional groups of these derivatives were confirmed using elemental analysis and spectral data. Furthermore, the derived compounds were evaluated for their antibacterial activity against Escherichia coli (Gram-negative) and Staphylococcus aureus (Gram-positive) strains using the agar-well diffusion method followed by molecular docking studies to predict binding interactions of the synthesized compounds with DNA gyrase.

Molecular Sensomics Combined with Random Forest Model Can Reveal the Evolution of Flavor Type of Baijiu Based on Differential Markers.

Baijiu is popular with a long history and balanced flavor. Flavor type is the most widely used classification mode for Baijiu. However, the evolutionary relationships of Baijiu flavor types and the differential markers between flavor types are still unclear, significantly impacting the development of the Baijiu industry. In this study, a total of 319 trace components were identified using gas chromatography-olfactometry-mass spectrometry and gas chromatography-mass spectrometry. Among them, 91 trace components with high odor active values or taste active values were recognized as flavor components. Then random forests were conducted to screen differential markers between the derived and basic flavor types, while a principal component analysis assessed their effectiveness in distinguishing the flavor types of Baijiu. Finally, 19 differential markers (including 3-methylbutyric acid, pentanoic acid, 2-butanol, 2,3-butanediol, ethyl pro-panoate, isobutyl acetate, ethyl butanoate, ethyl hexanoate, ethyl heptanoate, ethyl lactate, ethyl 2-hydroxy butanoate, isopentyl hexanoate, ethyl nonanoate, isopropyl myristate, ethyl tetradecanoate, ethyl benzoate, 2,4-di-t-butylphenol, 2-methylbutanal and 3-octanone) were screened and proven to effectively reveal the evolution of Baijiu flavor types; these were further verified as key differential markers using addition tests and a correlation analysis.

In Silico Study, Synthesis and Evaluation of Cytotoxic Activity of New Sulfonamide-Isatin Derivatives as Carbonic Anhydrase Enzyme Inhibitors

Aim: Design, molecular docking, synthesis, and evaluation of cytotoxic activity of new compounds I, II, III, and IV that have isatin-sulfonamide derivatives. Materials and Methods: for chemical synthesis, chemical compounds such as sulfonamide, 4-amino ethyl benzoate, isatin, and its derivatives were used. For the docking study (MOE), software program version 2015.10 was used. The MTT assay was utilized to predict the cytotoxic activity. Results: The synthesized compounds demonstrated significant inhibition of carbonic anhydrase XII activity through molecular docking, as well as significant inhibition of cancer cell viability. Compounds II and IV show higher S-scores than acetazolamide. Also, the MTT assay shows that compounds II and IV have IC50 values of 0.06 µM and 0.105 µM against MCF-7 cells, respectively, while acetazolamide has an IC50 value of 0.394 µM. While acetazolamide had an IC50 of 0.901 µM, compounds II and IV had IC50s of 0.063 µM and 0.114 µM against Hct116 cells, respectively. The MTT assay explains compounds II and IV have better cytotoxic activity compared with acetazolamide. Conclusion: New compounds that were produced showed signs of cytotoxicity and carbonic anhydrase inhibitory qualities.

Comparison of Volatile Compounds in Jingshan Green Tea Scented with Different Flowers Using GC-IMS and GC-MS Analyses.

Scented green tea (Camellia sinensis) is a type of reprocessed green tea produced by scenting with flowers. To investigate the differences in the volatiles of scented green tea processed with four different flowers (Jasminum sambac, Osmanthus fragrans, Michelia alba, and Rosa rugosa), gas chromatography-ion mobility spectrometry (GC-IMS) and gas chromatography-mass spectrometry (GC-MS) were employed to detect and identify the volatile compounds in the four types of scented teas. GC-IMS and GC-MS identified 108 and 101 volatile compounds, respectively. The key characteristic volatile compounds, namely indole, linalool, β-myrcene, benzyl acetate, and ethyl benzoate (jasmine tea); cedrol, (E)-β-ionone, γ-decalactone, and dihydro-β-ionol (osmanthus tea); geraniol, phenylethyl alcohol, jasmone, methyl jasmonate, hexadecanoic acid, 4-ethyl-benzaldehyde, 2-methylbutyl hexanoate, and indole (michelia tea); and 3,5-dimethoxytoluene, (E)-β-ionone, and 2-methylbutyl hexanoate (rose tea), were identified through chemometric analysis combined with relative odor activity values (ROAVs) and sensory evaluation. This study provides new insights into the formation of aroma molecular fingerprints during green tea scenting with flowers, providing theoretical guidance for infusing distinct aroma characteristics into green tea during scented tea processing.

The Fumigation Toxicity of Three Benzoate Compounds against Phosphine-Susceptible and Phosphine-Resistant Strains of Rhyzopertha dominica and Sitophilus oryzae.

Phosphine (PH3) has been widely used as a fumigant in food storage, but increasing PH3 resistance in major pests makes finding alternative fumigants urgent. Methyl benzoate (MBe), a volatile organic compound regarded to be a food-safe natural product, has recently demonstrated significant toxicity against a variety of insect pests. This study is the first evaluation of the fumigation toxicity of three benzoate compounds, MBe, vinyl benzoate, and ethyl benzoate, against PH3-susceptible and PH3-resistant strains of Rhyzopertha dominica and Sitophilus oryzae. All strains were exposed to the compounds at concentrations up to 20 µL/1.5 L air for 24 h. Compared to vinyl benzoate and ethyl benzoate, MBe induced higher mortality rates in all strains at all concentrations. When food was made available, the lethal median concentration for MBe was 10-17-fold higher than when tested without food. Moreover, no significant differences were observed between the responses of the PH3-susceptible and PH3-resistant strains to the compounds. Notably, S. oryzae was more susceptible to MBe. In laboratory settings, MBe successfully controlled PH3-resistant strains of R. dominica and S. oryzae, making it a viable option for PH3-resistance management. Thus, MBe might be suitable for food security programs as an environmentally benign alternative fumigant.

Exploring the Impact of Various Wooden Barrels on the Aromatic Profile of Aceto Balsamico Tradizionale di Modena by Means of Principal Component Analysis.

The study examines the unique production process of Aceto Balsamico Tradizionale di Modena PDO (ABTM), emphasizing its complex phases and the impact of raw materials and artisanal skill on its flavor characteristics. Analytical tests focused on the volatile composition of vinegars from different wood barrels at different aging stages, using solid-phase micro-extraction (SPME) coupled with gas chromatography, either with mass spectrometry (GC/MS) or flame ionization detector (FID). Multivariate analysis, including principal component analysis (PCA), was employed to investigate the presence of peculiarities among the volatile profiles of samples of different barrel origin. The research focuses on characterizing the volatile composition of vinegars sourced from individual wood barrels, such as Cherry, Chestnut, Mulberry, Juniper, and Oak. Although it was not possible to identify molecules directly connected to the woody essence, some similarities emerged between vinegar samples from mulberry and cherry barrels and between those of juniper and oak. The former group is characterized by analytes with high molecular weights, such as furfural and esters, while the latter group shows more intense peaks for ethyl benzoate. Moreover, ethyl benzoate appears to predominantly influence samples from chestnut barrels. Due to the highly complex production process of ABTM, where each battery is influenced by several factors, this study's findings are specific to the current experimental conditions.

Assessing the Cooperating Ability of 6‐Hydroxypicolinic Acid and Pyridyl‐Amide Ligands in Palladium‐Mediated C−H Activation

AbstractThe behavior of 6‐hydroxypicolinic acid (pic‐6‐OH) and pyridyl‐amides as cooperating ligands in the C−H activation of arenes has been studied experimentally. When deprotonated, both compounds are chelating ligands and bear either a pyridone moiety or an N‐acyl substituent that can assist the C−H cleavage in the same way as the successful bipyridone ligands and MPAAs do. In addition, they are easily available, commercially or via straightforward syntheses. Palladium complexes of formula (NBu4)[Pd(κ2‐O, N‐pic‐6‐O)(C6F5)py] (2) and [Pd(κ2‐N, N‐ py‐CH2N(COCF3)(C6F5)py] (6) have been synthesized and their decomposition in the presence of an arene gives the C6F5‐arene coupling product, showing that the ligands enable the C−H activation of the arene (arene=pyridine, toluene, ethyl benzoate). The amount of C6F5‐arene products observed leads to the following trend in cooperating ability: pic‐6‐OH > pyridyl‐amide. DFT calculations on the pyridine activation are consistent with the experimental findings. The C−H activation does not occur for the isomeric complex (NBu4)[Pd(κ2‐O, N‐pic‐4‐O)(C6F5)py] (4) with the pyridone oxygen far from the metal, showing the involvement of this moiety in the C−H cleavage. The performance of these ligands in the direct arylation of arenes has been evaluated.

Effect of hydrolyzed soybean on the volatile flavors and microbial community in the traditional brewing process of chi-flavor Baijiu.

Addition of soybean in raw materials could improve the flavor of chi-flavor Baijiu (CFB) in production. For investigating the mechanism of flavor improvement during fermentation, the changes of volatile flavors and their relationship with microbial community were analyzed. The results showed that the average contents of lactic and acetic acid in EG (added with hydrolyzed soybean) samples were higher those of CK (without hydrolyzed soybean) samples. The contents of main volatile esters, including ethyl acetate, ethyl palmitate, and ethyl benzoate, in EG samples were higher than those in CK samples at the end of fermentation. The content of alcohols in EG sample was 140.55mg/L, higher than that in CK sample at the end of fermentation. Especially, the average content of characteristic flavor β-phenylethanol in EG samples increased 17.6% in comparison with that in CK samples during fermentation. Lactobacillus and Pediococcus were the dominant bacterial genera, whereas Saccharomyces, Mortierella, and Trichosporon were dominant fungal genera in both CK and EG samples. Lactobacillus and Weissella confusa showed strong positive correlation with β-phenylethanol, ethyl acetate, and ethyl benzoate. This study provides an in-depth analysis of the effects of hydrolyzed soybeans on the volatile flavor compounds and microbial communities of CFB and theoretical guidance for improving the quality of CFB.

Photoactivated ultralong room‐temperature phosphorescence from epoxy polymer films doped with carbazole derivatives for erasable light printing

AbstractThe development of polymer‐based luminescent materials with efficient and switchable ultralong organic phosphorescence (UOP) under ambient conditions is of great importance but remains challenging. In this work, three new organic luminogens have been developed by attaching the ethyl benzoate to the nitrogen atoms of carbazole, 7H‐benzo[c]carbazole, and 7H‐dibenzo[c,g]carbazole via the Buchwald‐Hartwig coupling reaction, respectively. Subsequently, they are embedded into epoxy polymers through doping into the mixtures of bisphenol A diglycidyl ether and 1,3‐propylenediamine, followed by a thermal curing reaction. It is found that the resulting polymer films EB‐BCz@EP and EB‐2BCz@EP show unique photoactivated UOP properties. After UV light irradiation, their phosphorescence quantum yields are up to 7.6%, and the lifetimes reach 1.84 and 1.18 s, respectively. These observations suggest that it is possible to elevate the UOP lifetime without reducing the phosphorescence quantum yield by tuning the molecular structure of the guest luminogen. Upon thermal annealing, the photoactivated polymer films can recover to the pristine state, demonstrating switchable UOP characteristics of the polymer films in the air. Inspired by these exciting results, the EB‐2BCz@EP has been successfully explored as a transparent polymer film for erasable light printing.

GC/MS-based untargeted metabolomics reveals the differential metabolites for discriminating vintage of Chenxiang-type baijiu

The “outstanding and unique aged aroma” of Chinese Chenxiang-type baijiu (CXB)–Daoguang 25 (DG25) mainly originates from a “extraordinary storage technology” of Mujiuhai (a wooden container), so it is mysterious and interesting. In this study, an untargeted GC/MS-based metabolomics was used to reveals the volatile differential metabolites for discriminating six different vintages of DG25 combing with chemometrics. A total of 100 volatile metabolites (including unknowns) were extracted and identified, including esters (41%), alcohols (10%) and acids (7%) so on. Finally, 33 differential metabolites were identified as aging-markers. Among them, 25 aging-markers showed a downtrend, including 17 esters such as ethyl acetate, ethyl hexanoate and ethyl palmitate so on. Moreover, it was interesting and to further study that furans showed a significant downtrend. Statistically speaking, ethyl benzoate played an important role in discriminating vintage of 1Y and 3Y, and the other 24 differential metabolites with downtrend discriminating the unstored (0Y-aged) DG25. Eight differential metabolites, such as ethyl octanoate, benzaldehyde, 3-methylbutanol and 1,1-diethoxyaccetal so on increased during aging of DG25, and they played a statistical role in discriminating the 5Y-, 10Y- and 20Y-aged DG25. This study provides a theoretical basis way for the formation mechanism of aging aroma for CXB.

Novel insights into flavor formation in whey fermented wine: A study of microbial metabolic networks

In this study, the alterations in the flavor components of whey fermented wine (WFW) were analyzed using gas chromatography–mass spectrometry (GC-MS). Moreover, the changes in the bacterial community structure of WFW were examined using high-throughput sequencing technology. The results showed that the pH value decreased from 5.61 to 3.51 between 0 d and 28 d of fermentation. Meanwhile, the content of total acids (1.31°T to 7.32°T), alcohol (8.83%–12.57%), flavonoids (33.98–60.52 mgRE/100 mL), and polyphenols (120.24–230.34 mgGAE/100 mL) increased during fermentation. At the early stage of fermentation, Lactobacillus was the predominant bacterial genus in WFW. However, as fermentation progressed, Lactobacillus and Lactococcus gradually became the dominant genera. Using GC-MS, 102 volatile compounds were identified during fermentation. Among them, 15 substances — including ethyl benzoate, phenyl ethyl acetate, and ethyl butyrate — were identified as the important aroma components of WFW. Fourteen amino acids were detected during fermentation, among which leucine (260.78 μg/L) and tyrosine (250.37 μg/L) showed the highest content. Correlation analysis revealed that Lactococcus was positively correlated with most ester compounds, and Lactobacillus was positively correlated with ethyl phenylpropionate, acetaldehyde, and caprylic acid. Meanwhile, Klebsiella exhibited a significant positive correlation with histidine, aspartic acid, and alanine.

Effect of Laterally Substituted Methoxy Group on the Liquid Crystalline Behavior of Novel Ester Molecules

Background: The aim of this research is to study the effect of length-to-width ratio on mesomorphism to enhance the understanding of its potential applications. This will be achieved by synthesizing a unique and innovative series of identical ester molecules, including lateral methoxy groups and terminal ethyl benzoate groups. In this research, we aim to find new insights into the relationship between molecular structures and mesomorphic behaviors, which could have significant implications for the development of advanced materials with adapted properties. : The objective of the study is to investigate the mesophase behavior of new ester mesogens and determine how they are influenced by lateral methoxy groups. By identifying the underlying perspectives and relationships between these variables, we hope to better understand the unique properties and potential applications of these materials. Method: In this research work, the focus is on the synthesis of ethyl(E)-4-((3-(4-alkoxy-3- methoxyphenyl)acryloyl)oxy)benzoate, which is prepared from Steglich esterification method by using (E)-3-(4-alkoxy-3-methoxyphenyl)acrylic acid and ethyl 4- hydroxybenzoate. Synthesis processes involve precise reaction sequences designed to ensure maximum yield and purity of the final product. By providing a detailed report on the experimental process, this study contributes to the ongoing research efforts aimed at the development of innovative compounds with various applications in liquid crystals Result: A new set of liquid crystal derivatives has been synthesized and studied to investigate the effect of molecular structure on the behavior of liquid crystals, with particular attention to the group -OCH3 located laterally. This series was composed of 12 derivatives (C1-C16). Among them, the first six derivatives (C1-C6) did not have the characteristics of a liquid crystal, while the remaining derivatives (C7 and C8) had a monotropic behavior, and C10-C16 had an enantiotropic smectogenic liquid crystal behavior without exhibition of the nematic phase. The average thermal stability of the smectic property was 87.33 °C, and the mesophase range was 2 °C to 14 °C. The molecular structure was confirmed by analytical and spectral analysis. The properties of liquid crystals of this new series were compared with those of other known structurally similar homologous series. The transition temperatures were determined with an optical polarizing microscope equipped with a heating phase. Conclusion: The mesomorphic thermal and optical properties of the compounds have been validated by DSC and POM techniques. The result shows that the length of the alkyl chain has a significant influence on the mesomorphic characteristics and thermal stability of the different mesophases. Evaluation of the compounds studied indicates that the molecules are sensitive to their lateral substituent, which influences the thermal characteristics and stability of the mesophase.

Effect of internal and external electron donors on stereospecific polymerization of isoprene with TiCl4/MgCl2 type Ziegler-Natta catalysts

Two TiCl4/MgCl2 type Ziegler-Natta catalysts containing ethyl benzoate (EB) and dibutyl phthalate (DBP) as internal electron donors (ID) were prepared for isoprene polymerizations using five kinds of external electron donors (ED) (phenyltrimethoxysilane (ED-1), dicyclopentyl(dimethoxy)silane (ED-2), 2-butyl-2-ethyl-1,3-dimethoxypropane (ED-3), 1,3-dimethoxypropane (ED-4) and di(2-ethylhexyl)phthalate (ED-5)). The structure features of TiCl4/ID/MgCl2 catalysts were characterized and the effect of ID and ED on polymerization behaviors was studied. EB had higher adsorption content on catalyst surface, higher catalytic activity and lower trans-1,4 stereoselectivity than DBP. Appropriate introduction of ED-1 and ED-2, expect ED-3, ED-4 and ED-5, caused the enhancement in polymerization activity and trans-1,4 content, while excess addition led to the deactivation. The effect of ED on equilibrium between selective activation and deactivation of active species significantly relied on the electron donor type and concentration.

Synthesis, Antimalarial, Antileishmanial, and Cytotoxicity Activities and Preliminary In Silico ADMET Studies of 2-(7-Chloroquinolin-4-ylamino)ethyl Benzoate Derivatives.

A series of heterocyclic chloroquine hybrids, containing a chain of two carbon atoms at position four of the quinolinic chain and acting as a link between quinoline and several benzoyl groups, is synthesized and screened in vitro as an inhibitor of β-hematin formation and in vivo for its antimalarial activity against chloroquine-sensitive strains of Plasmodium berghei ANKA in this study. The compounds significantly reduced haeme crystallization, with IC50 values < 10 µM. The values were comparable to chloroquine's, with an IC50 of 1.50 ± 0.01 µM. The compounds 4c and 4e prolonged the average survival time of the infected mice to 16.7 ± 2.16 and 14.4 ± 1.20 days, respectively. We also studied the effect of the compounds 4b, 4c, and 4e on another important human parasite, Leishmania mexicana, which is responsible for cutaneous leishmaniasis, demonstrating a potential leishmanicidal effect against promasigotes, with an IC50 < 10 µM. Concerning the possible mechanism of action of these compounds on Lesihmania mexicana, we performed experiments demonstrating that these three compounds could induce the collapse of the parasite mitochondrial electrochemical membrane potential (Δφ). The in vitro cytotoxicity assays against mammalian cancerous and noncancerous human cell lines showed that the studied compounds exhibit low cytotoxic effects. The ADME/Tox analysis predicted moderate lipophilicity values, low unbound fraction values, and a poor distribution for these compounds. Therefore, moderate bioavailability was expected. We calculated other molecular descriptors, such as the topological polar surface area, according to Veber's rules, and except for 2 and 4i, the rest of the compounds violated this descriptor, demonstrating the low antimalarial activity of our compounds in vivo.

Characterization and comparison of key aroma compounds in traditional and rapid Yongchuan douchi by molecular sensory science

Yongchuan douchi is a famous soybean product that is widely used as a condiment in China due to its attractive aroma and can be categorized into traditional and rapid Yongchuan douchi (TYD and RYD). However, the key aroma compounds in TYD and RYD and their differences remain poorly understood. In the present study, the key aroma compounds in TYD and RYD were characterized and compared by a molecular sensory approach. The results obtained by multidimensional gas chromatography-mass spectrometry/olfactometry (MDGC−MS/O) demonstrated that a total of 125 volatiles and 71 aroma-active compounds were identified. Moreover, 36 aroma-active compounds with relative odor activity values (rOAVs) ≥ 1 and flavor dilution (FD) ≥ 16 were screened and quantified by an external standard method. The recombination and omission experiments revealed that TYD and RYD contained 18 and 13 key aroma compounds, respectively. TYD and RYD contained 10 identical compounds, whereas 8 (ethyl 2-methylbutyrate, ethyl 3-methylbutyrate, ethyl isobutyrate, ethyl caproate, ethyl acetate, ethyl benzoate, 4-methyl-2-phenyl-2-pentenal, acetophenone) and 3 (phenylacetaldehyde, 4-ethyl guaiacol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone) were unique to TYD and RYD, respectively. This is the first report of key aroma compounds in TYD and RYD, and it provides insights into improving the aroma of Yongchuan douchi.

Importance of hydrogen bonding in base-catalyzed transesterification reactions with vicinal diols

The transesterification reaction kinetics of 2-(benzoyloxy)ethyl benzoate with various alcohols (ethylene glycol, 1,3-propanediol, 1-butanol, propylene glycol and 1,2-butylene glycol) using various cyclic amidine catalysts were investigated. For transesterification with excess glycol (glycolysis), the rate was nearly zero order in diester and glycol concentration, which is substantially different from classical transesterification kinetics with mono-alcohols. The measured kinetic parameters during glycolysis are consistent with a reaction path that is kinetically limited by the decomposition of the reaction intermediate formed from the alkoxide and diester. The DFT-calculated reaction energy and activation barrier for decomposition of this intermediate reveal a critical role of intramolecular hydrogen-bond stabilization made possible by the vicinal –OH of the glycol that effectively increases the concentration of the intermediate during reaction resulting in acceleration of the overall transesterification rate. These findings indicate the nature of both the alcohol solvent and the catalyst influence transesterification rate, and results suggest they are also important in the deconstruction of carbonyl-containing condensation polymers.

A BAHD acyltransferase contributes to the biosynthesis of both ethyl benzoate and methyl benzoate in the flowers of Lilium oriental hybrid 'Siberia'.

Lily is a popular flower worldwide due to its elegant appearance and pleasant fragrance. Floral volatiles of lily are predominated by monoterpenes and benzenoids. While a number of genes for monoterpene biosynthesis have been characterized, the molecular mechanism underlying floral benzenoid formation in lily remains unclear. Here, we report on the identification and characterization of a novel BAHD acyltransferase gene that contributes to the biosynthesis of two related floral scent benzoate esters, ethyl benzoate and methyl benzoate, in the scented Lilium oriental hybrid 'Siberia'. The emission of both methyl benzoate and ethyl benzoate in L. 'Siberia' was found to be tepal-specific, floral development-regulated and rhythmic. Through transcriptome profiling and bioinformatic analysis, a BAHD acyltransferase gene designated LoAAT1 was identified as the top candidate gene for the production of ethyl benzoate. In vitro enzyme assays and substrate feeding assays provide substantial evidence that LoAAT1 is responsible for the biosynthesis of ethyl benzoate. It was interesting to note that in in vitro enzyme assay, LoAAT1 can also catalyze the formation of methyl benzoate, which is typically formed by the action of benzoic acid methyltransferase (BAMT). The lack of an expressed putative BAMT gene in the flower transcriptome of L. 'Siberia', together with biochemical and expression evidence, led us to conclude that LoAAT1 is also responsible for, or at least contributes to, the biosynthesis of the floral scent compound methyl benzoate. This is the first report that a member of the plant BAHD acyltransferase family contributes to the production of both ethyl benzoate and methyl benzoate, presenting a new mechanism for the biosynthesis of benzoate esters.

Effects of traditional starter and the Round‐Koji‐Maker starter on microbial communities and volatile flavours of Chi‐Flavour Baijiu

SummaryThe mechanised starter‐making has been widely applied to the brewing of Baijiu. However, the effect of mechanical production on microbial flora and volatile flavour compounds of Chi‐Flavour Baijiu was still unknown. This study was to investigate the differences in microbial flora and volatile flavours between the traditional starter Baijiu (BQ) and Round‐Koji‐Maker Starter Baijiu (SQ) during brewing. The results showed that the contents of alcohol, total acidity and organic acid in BQ were significantly higher than those in SQ at the end of fermentation (P &lt; 0.05). The dominant bacterial and fungal genera in SQ and BQ were Lactobacillus and Saccharomyces, respectively. The relative content of Pediococcus and Weissella in BQ was significantly higher than those in SQ in the prophase of fermentation. In respect of volatile flavours, there were 117 kinds of volatile flavours detected in SQ, higher than 90 kinds of those in BQ during the fermentation. The characteristic volatile flavours of Chi‐Flavour Baijiu were all detected with no significant difference between BQ and SQ, and the difference in flavours mainly came from 2‐methoxy‐4‐methylphenol, ethyl decanoate, (E)‐hept‐2‐enal. Lactobacillus was significantly positively correlated with ethyl decanoate and ethyl benzoate in BQ and phenethyl acetate in SQ. In addition, Candida had a strong positive correlation with β‐phenylethanol and ethyl myristicate in BQ and SQ. This study provides an in‐depth analysis of the difference between traditional and mechanical Xiaoqu starters in Baijiu fermentation and theoretical guidance for the standard production and quality improvement of Chi‐Flavour Baijiu.

Characterization of the volatile profile of feijoa (Acca sellowiana) fruit at different ripening stages by HS-SPME-GC/MS

This study investigated the changes of volatile organic compounds (VOCs) in feijoa fruits during ripening. The VOCs were determined by head space solid phase microextraction and gas chromatography coupled to mass spectrometry (HS-SPME-GC/MS). Results showed that 78 VOCs were identified, mainly containing esters, terpenoids, aldehydes and alcohols. Only the minority of VOCs had relatively higher contents in unripe feijoa fruits, while most VOCs were highly accumulated in mid-ripe and ripe feijoa fruits. In the early stage, aldehydes and alcohols were the main flavor compounds which provided fruity and green aroma. The contribution of esters and terpenoids increased during the ripening process, leading to strong fruity and flower fragrance. Hexanal was the main volatile component of unripe feijoa fruits, while methyl benzoate, ethyl benzoate and 3-carene were the main volatile components of mid-ripe and ripe feijoa fruits. According to partial least square-discriminant analysis (PLS-DA), 17 VOCs with variable importance in the projection (VIP) > 1 could be used as significant markers to distinguish feijoa fruits during ripening. This study provided a theoretical support for the further study of the formation mechanism of VOCs in feijoa fruits during the ripening process.

GC-MS Silylation Derivative Method to Characterise Black BIC® Ballpoint 2-Phenoxyethanol Ratio Evaporation Profile-A Contribution to Ink Ageing Estimation.

One of the major challenges in forensic document analysis is estimating the age of ink deposition on a manually written document. The present work aims to develop and optimise a methodology, based on the evaporation of 2-phenoxyethanol (PE) over time, that can contribute to ink age estimation. A black BIC® Crystal Ballpoint Pen was purchased in a commercial area, and ink deposition began in September 2016 over 1095 days. For each ink sample, 20 microdiscs were subjected to n-hexane extraction in the presence of an internal standard (ethyl benzoate) followed by derivatisation with a silylation reagent. A gas chromatography-mass spectrometry (GC/MS) method was optimised for PE-trimethylsilyl (PE-TMS) to characterise the ageing curve. The developed method presented good linearity between 0.5 and 50.0 μg mL-1, as well as limits of detection and quantification of 0.026 and 0.104 μg mL-1, respectively. It was possible to characterise PE-TMS concentration over time, which reveals a two-phase decay behaviour. First, there was a substantial decline between the 1st and the 33rd day of deposition, followed a by a stabilisation of the signal, which allowed to detect the presence of PE-TMS up to 3 years. Two unknown compounds were also present and allowed to identify three dating time frames for the same ink stroke: (i) between time 0 and 33 days, (ii) between time 34 and 109 days, and (iii) more than 109 days. The developed methodology allowed to characterise the behaviour of PE over time and to establish a relative dating of three-time frames.