MOLECULES
·
2024
·Vol. 29
·期 15
·3597
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IF 4.2
Xun Liu,Wenli Quan
As one of the most essential types of heterocyclic compounds, pyrazines have a characteristic smell and taste and have a wide range of commercial applications, especially in the food industry. With the development of the food industry, the demand for pyrazines has increased. Therefore, understanding the properties, functions, and synthetic pathways of pyrazines is one of the fundamental methods to produce, control, and apply pyrazines in food or medical systems. In this review, we provide an overview of the synthesis pathways and physiological or pharmacological functions of naturally occurring pyrazines. In particular, we focus on the biosynthesis and pharmacological effects of 2,3,5,6-Tetramethylpyrazine (TTMP), 2,5-Dimethylpyrazine (2,5-DMP), and 2,3,5-trimethylpyrazine (TMP). Furthermore, areas where further research on pyrazines is needed are discussed in this work.
研究领域:
食品科学
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医药学
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生物化学
✓ 已验证
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2021
·
IF 7.514
Yun-Jiao Ma,Xiao-Yuan Wang,Bei-Wei Zhu,Ming Du,Liang Dong,Xiu-Ping Dong,Xian-Bing Xu
Vinylpyrazine compounds are widely present in foods , especially in hot-processed foods, as a class of flavor compounds ; however, their formation mechanism in food systems is still unclear. Therefore, in this study, 2-vinylpyrazine and 2-vinyl-6-methylpyrazine were identified in the Maillard model reaction of d -glucose and glycine. The Maillard model reaction of glucose–glycine was constructed to explore the effects of reaction parameters on vinylpyrazines and the related products. The Maillard reaction of [U- 13 C 6 ] glucose and glycine was established, and alkylpyrazines and formaldehyde were determined via isotope tracing technique as the precursors of vinylpyrazines. The formation of vinylpyrazines was verified by building a model reaction between alkylpyrazines and formaldehyde. The H/D exchange experiment confirmed that the active site of alkylpyrazines was on the methyl group , which was the reaction site for the condensation reaction of alkylpyrazines with formaldehyde. Results suggest that vinylpyrazines are formed by the condensation reaction of alkylpyrazines and formaldehyde.
研究领域:
食品科学
·
化学
✓ 已验证
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2025
·
IF 9.8
Tong Zhou,Qingqing Chai,Man Zhang,Heping Cui,Ahmad Mohammad,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
Exogenous xylose (Xyl) could promote 2-furfural formation but inhibit pyrazines generation during its co-heating with alanine (Ala)-Xyl Amadori rearrangement product (AX-ARP). The activation energy of AX-ARP formation from Ala and Xyl was considerably lower than that of pyrazine formation from Ala and glyoxal (GO). Accordingly, the preferential interaction of exogenous Xyl with regenerated Ala triggered a continuous cycle of consumption and regeneration of Ala in AX-ARP-Xyl model. In this way, functioning as a catalyst, regenerated Ala facilitated the continuous conversion of AX-ARP into deoxyxylosones (DXs). However, exogenous Xyl accelerated the pH drop during the thermal treatment of AX-ARP, which favored the conversion of DXs into 2-furfural while limiting the transformation of their α-dicarbonyl fragments into pyrazines. Model reactions of AX-ARP-[ 13 C 5 -Xyl] further confirmed that exogenous Xyl was progressively converted into 2-furfural, while its downstream products, such as GO and methylglyoxal (MGO), did not exhibit an enhanced tendency to form pyrazines.
研究领域:
食品科学
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生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
MATERIALS LETTERS
·
2023
·
IF 3
Lili Gao,Ping Hu,Yingzhen Hu,Yingjie Hu,Jing Zhang
Here, the crystal synthesis, crystal structures, optical band gaps and application in devices of (C 4 N 2 H 6 )PbI 3 and (C 4 N 2 H 6 )PbBr 3 are researched and discussed. Novel hybrid 1D perovskite single crystals based on pyrazine were obtained by reacting the organic cation C 4 N 2 H 6 with lead iodide and bromide. The band gaps of (C 4 N 2 H 6 )PbI 3 and (C 4 N 2 H 6 )PbBr 3 compounds are 2.71 and 2.82 eV, respectively, which consistent with the structure distortion. The 1D crystals of (Py)PbI 3 and (Py)PbBr 3 assisted the device efficiency from 20.15% to 22.12 and 22.38%, respectively.
研究领域:
材料科学
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光学
✓ 已验证
产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2025
·
IF 9.8
Han Zhang,Heping Cui,Xue Xia,Shahzad Hussain,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
Exogenous xylose exhibited a significant temperature-dependent regulatory effect on the furans and pyrazines formation during the degradation of dual-glycated Amadori rearrangement product of lysine (Lys), N α ,N ε -di(1-deoxy- d -xylulos-1-yl)lysine ( N α ,N ε -di-Xul-Lys ARP). At 100 °C, xylose primarily enhanced the dehydration pathway of deoxypentosone. This significantly increased furans yield, while delaying lysine release by interacting with mono-glycated Lys-ARPs, thereby inhibiting the early formation of pyrazines. 120 °C accelerated the dehydration and retro-aldolization of deoxypentosone, markedly boosting furans formation and further promoting the substantial production of α -dicarbonyl compound with extra-added xylose. Additionally, xylose buffered the rapid pH decline, enhancing the α -aminoketones electrophilicity and facilitating pyrazines formation in N α ,N ε -di-Xul-Lys ARP. At 140 °C, xylose hindered furans formation but notably increased methylpyrazine levels during 30–60 min. Furthermore, increasing the xylose concentration to 60 mmol/L at 120 °C markedly enhanced glyoxal and methylglyoxal production, yielding the highest pyrazine concentration of 98.04 μg/L within 60 min.
研究领域:
食品科学
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生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
ACS Catalysis
·
2025
·
IF 13.1
Zhitong Zhou,Weixiang Guan,Xiaoli Pan,Aiqin Wang,Tao Zhang
One-pot amination coupling of vicinal diols toward the synthesis of pyrazines provides an efficient and economically viable route to access N-heterocycles from biomass, yet the current methodology relies on a fragile homogeneous catalyst system, which limits the sustainability of the chemistry. In this work, we developed a highly efficient heterogeneous catalyst 0.8Pt/13CeO2/Al2O3 which afforded diverse substituted pyrazines from readily available vicinal diols and ammonia with a yield up to 94% under mild reaction conditions and could be reused at least 6 times without obvious activity decay. Compared to the Pt/Al2O3 catalyst, the 0.8Pt/13CeO2/Al2O3 catalyst exhibited a 30-fold faster conversion rate of diols and an increased pyrazine selectivity from 48% to 79%. Characterizations revealed that doped CeO2 improved the dispersion of Pt, increased the electron density on the Pt sites, optimized the acid/basic property of the catalyst, and enhanced the adsorption strength and dehydrogenation ability of diols. All these features contributed to the increased activity and selectivity.
研究领域:
化学工程
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催化化学
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生物质利用
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2022
·
IF 5.895
Tong Zhou,Xue Xia,Heping Cui,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
The intervention of cysteine (Cys) on the formation of 2,3-butanedione and pyrazines was evaluated during the thermal processing of the alanine-xylose Amadori compound (AX-ARP). With the involvement of Cys, the competitive formation of 2,3-butanedione and pyrazines was induced. The formation of 2,3-butanedione in the AX-ARP/Cys model was suppressed due to the inhibitory effect of the precursors of 2,3-butanedione like deoxypentosones, while the added Cys in the AX-ARP/Cys model competed with the recovered alanine (Ala) to capture glyoxal and methylglyoxal to make up for the absence of pyrazines in the AX-ARP model at an initial pH value of 7. The content of pyrazines increased from 0 up to 16.48 μg/L (120 °C, 120 min). Exogenous Cys itself showed lower reactivity with 2,3-butanedione through the Strecker degradation reaction; while the pH was increased to 8, the degradative products of Cys were facilitated to consume the residual 2,3-butanedione giving rise to the formation of 2,4,5-trimethylthiazole at 120 °C. It was the degradative products of Cys that accelerated the reaction for consumption of 2,3-butanedione rather than Cys itself. Additionally, the inhibitory effect of Cys on 2,3-butanedione formation was weakened under a basic condition, while the promotional effect on the formation of pyrazines was further boosted. With more Cys participating in the process of AX-ARP thermal degradation, the formation of 2,3-butanedione was further inhibited, while the yields of pyrazines were increased.
研究领域:
食品科学
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生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2023
·
IF 6.1
Tong Zhou,Xue Xia,Heping Cui,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
The contribution of glutathione (GSH) and free amino acids degraded from GSH to the generation of pyrazines and 2,3-butanedione was illustrated during their interaction in the thermal treatment of the Amadori compound of alanine and xylose (ARP). GSH-degraded amino acids, glutamic acid (Glu), cysteine (Cys), and glycine (Gly), but not pyroglutamic acid (pGlu), could effectively capture α-dicarbonyls to facilitate the formation of pyrazines when ARP was heated with GSH. Deoxypentosones, the precursors of 2,3-butanedione, were largely consumed in the ARP–GSH model by the interaction with GSH and its degradative Cys compared with the ARP model. The addition of GSH and deoxypentosones inhibited the further degradation of deoxypentosones, resulting in less formation of 2,3-butanedione and other α-dicarbonyl compounds. Meanwhile, the reaction between GSH-degraded Cys and deoxypentosones to form sulfur-containing compounds such as thiols accelerated the consumption of deoxypentosones; thereby, the formation of 2,3-butanedione was severely interfered. However, this inhibition was compensated for by the GSH-degraded Gly through the addition between Gly and MGO and the subsequent deamination. The involvement of exogenous GSH could simultaneously boost the yields of 2,3-butanedione and pyrazines compared with those of ARP heated alone. As the degree of GSH degradation strengthened in the ARP-thermal-degraded GSH models, the yields of both pyrazines and 2,3-butanedione steadily increased.
研究领域:
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2024
·
IF 3.3
Yuxia Yuan,Khizar Hayat,Jibao Cai,Da Xu,Shuqin Xia,Heping Cui,Jingyang Yu
BACKGROUND The typical aroma compounds in methionine-glucose Maillard products often undergo further degradation and polymerization during storage and thermal processing, leading to flavor dispersion and aroma distortion. It is crucial to identify measures that enhance typical aroma substances in such flavor matrices. RESULTS The effect of oxygen on the flavor formation of methionine-glucose thermal reaction system was explored by determining typical flavor substance contents and flavor differences. Compared with the oxygen concentration in the air (21%), a high oxygen concentration (30% and 40%) effectively promoted the formation of typical flavor substances. Pyrazines increased by 44% and thioethers increased by 13%. The reaction process and the content of key substances were both measured to explain the involvement of oxygen. It was found that high oxygen concentration increased the reaction efficiency of glucose and methionine and promoted the formation of α -dicarbonyl compounds, including glyoxal, methylglyoxal and 3-deoxyglucosinone. Moreover, a glyoxal-methylglyoxal-methionine model system was established to verify the effect of oxygen intervention on the formation of pyrazines and thioethers generating from α -dicarbonyl compounds. It was confirmed that a high oxygen concentration promoted the consumption of glyoxal and methylglyoxal, which were more readily converted into pyrazines and thioethers without forming melanoidins. CONCLUSION A high concentration of oxygen promoted the formation of pyrazines and thioethers during the Maillard reaction of methionine and glucose, and effectively inhibited the occurrence of browning. The present study provides a new concept for the typical flavor enhancement of methionine-glucose Maillard reaction products. © 2024 Society of Chemical Industry.
研究领域:
食品科学
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化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Qiuyan Liu,Wenjing Huang,Caiyan Sheng,Yida Wu,Mingxia Lu,Tiehan Li,Jixin Zhang,Yuming Wei,Yujie Wang,Jingming Ning
Large-leaf yellow tea (LYT) is processed from both leaves and stems, resulting in a distinctive rice crust–like aroma. Tea stems may contribute differently to the aroma of LYT than leaves. This study aimed to clarify the specific contribution of stems to LYT. The volatile compounds in different components of LYT were extracted and analyzed using a combination of headspace solid-phase microextraction and stir bar sorptive extraction coupled with gas chromatography-olfactory-mass spectrometry. The results revealed high concentrations of compounds with roasty attributes in stems such as 2-ethyl-3,5-dimethylpyrazine (OAV 153–208) and 2-ethyl-3,6-dimethylpyrazine (OAV 111–140). Aroma recombination and addition experiments confirmed that the roasty aroma provided by stems plays a pivotal role in the formation of the distinctive flavor of LYT. This study offers novel insights into the contribution of stems to the aroma of LYT, which can be used for processing and quality enhancement of roasted tea.
研究领域:
食品科学
·
茶叶加工学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMICAL PHYSICS LETTERS
·
2022
·
IF 2.719
Jianghui Liu,Juan Cui,Jianfeng Gao,Huahua Guo,Xu Chai
In this study, activated carbon operated by microwave (MW) pretreatment and further MW regeneration was used to remove sulfachloropyridazine (SCP) to explore the influence of MW on activated carbon. The results reveal the adsorption capacity (q e , exp ) of pretreated activated carbon (PAC) was double that of the original activated carbon (OAC). With an increase in adsorption/MW times, the q e , exp of regenerated activated carbon (RAC) did not change much. Through Brunauer-Emmett-Teller (BET) analyses, the Micropore volume of PAC (V micro = 0.4035 cm 3 g −1 ) was higher than that of OAC (V micro = 0.1548 cm 3 g −1 ), this indicated that PAC creates a large number of micropores as a result of MW pretreatment. Also, S BET of RAC kept within a stable range (824.97–868.88 cm 2 g −1 ), and S BET of 6th-RAC was still as high as 861.18 m 2 g −1 after 6 continuous adsorption/MW cycles, which indicated the activated carbon restored stable properties after multiple microwave regeneration.
研究领域:
环境科学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2018
·
IF 6.14
Mengjie Wu,Hui Ma,Zhongyi Ma,Yufang Jin,Chunyan Chen,Xiaoya Guo,Yan Qiao,Christian Marcus Pedersen,Xianglin Hou,Yingxiong Wang
Deep eutectic solvents (DESs) exhibit similar physicochemical properties to the ionic liquids. They are inexpensive, renewable, nontoxic, and environmentally benign solvents and have gradually attracted attention in several fields, for example, biorefinery. Here choline chloride-based DESs have been used as solvents and catalysts for the preparation of deoxyfructosazine (DOF) through a self-condensation reaction of d-glucosamine (GlcNH2). The catalytic performances of a “green cocatalyst”, amino acids, and the reaction mechanism were also studied. The results displayed that choline chloride/urea was capable to convert GlcNH2 efficiently, with a 13.5% yield of DOF at low temperature and with a short reaction time (100 °C, 150 min). Among the screened amino acids, arginine showed the highest activity and gave the highest yield of DOF (30.1%) under the optimized reaction conditions. Nuclear magnetic resonance (NMR) studies revealed a strong hydrogen bond interaction between GlcNH2 and arginine. Moreover, a detectable intermediate, namely dihydrofructosazine, in the condensation of GlcNH2 to DOF/fructosazine (FZ) was captured by in situ NMR technique.
研究领域:
有机化学
·
绿色化学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）