RSC Advances
·
2021
·Vol. 11
·期 52
·32654-32670
·
IF 3.361
Chang Yu,Min Liang,Su-Yi Dai,Hai-Jun Cheng,Li Ma,Fang Lai,Xiong-Min Liu,Wei-Guang Li
Cinnamaldehyde, cinnamyl alcohol, β-methylstyrene and cinnamic acid are four important biomass 3-phenyl-2-propene compounds. In the field of perfume and organic synthesis, their thermal stability and oxidation pathways deserve attention. This paper reports a new attempt to investigate the thermal stability and reactivity by a custom-designed mini closed pressure vessel test (MCPVT). The pressure and temperature behaviors were measured by MCPVT under nitrogen and oxygen atmosphere. The temperature of initial oxygen absorption (Ta) and rapid oxidation (TR) were calculated. The results showed that four 3-phenyl-2-propene compounds were stable under nitrogen atmosphere. The Ta of cinnamaldehyde, cinnamyl alcohol, β-methylstyrene, and cinnamic acid was 271.25 K, 292.375 K, 323.125 K, and 363.875 K, and their TR was 301.125 K, 332.75 K, 357.91 K, and 385.375 K, respectively. The oxidation reactivity order was derived to be cinnamaldehyde > cinnamyl alcohol > β-methylstyrene > cinnamic acid. The oxidation kinetics were determined using n versus time (n–t) plots, which showed a second-order reaction. Peroxide was determined by iodimetry, and the oxidation products were analyzed by gas chromatography-mass spectrometry (GC-MS). The results showed that the peroxide value of cinnamaldehyde, cinnamyl alcohol, β-methylstyrene, and cinnamic acid reached 18.88, 15.07, 9.62, and 4.24 mmol kg−1 at 373 K for 6 h, respectively. The common oxidation products of four 3-phenyl-2-propene compounds were benzaldehyde, benzoic acid, and epoxide, which resulted from the carbon–carbon double bond oxidation. The substituents' oxidation products were obtained from the oxidation of cinnamaldehyde, cinnamyl alcohol, and β-methylstyrene. In particular, the difference is that no oxidation products of the carboxyl group of cinnamic acid were detected. The common oxidation products of the four 3-phenyl-2-propene compounds were benzaldehyde, benzoic acid, and epoxide, which resulted from the carbon–carbon double bond oxidation. The substituents' oxidation products were caught in the oxidation of cinnamaldehyde, cinnamyl alcohol, and β-methylstyrene. In particular, the difference is that no oxidation products of the carboxyl group of cinnamic acid were detected. According to the complex oxidation products, important insights into the oxidation pathways were provided.
研究领域:
有机化学
·
生物质化学
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DOI
高影响因子
Journal of Food Measurement and Characterization
·
2024
·
IF 2.9
Zhou Zhen,Liu Shengkai,Cui Liying,Liu Zhongkai,Li Xiaoyu,Liu Zhiguo,Fu Yujie
This study explored the ultrasonic-microwave synergistic extraction technique for obtaining cinnamaldehyde and cinnamic acid from cinnamon twigs, and determined the most favorable extraction conditions. The optimization of extraction parameters, including extraction time, ethanol concentration, liquid-to-solid ratio, and microwave power, was achieved through single-factor experiments and the response surface method. The results of the significance analysis indicated that ethanol concentration and extraction power were the two primary factors affecting the extraction rates of cinnamaldehyde and cinnamic acid. Under the optimal conditions—600 W microwave power, 75% ethanol concentration, a liquid-to-solid ratio of 1:15, and a 20-min extraction time——the extraction efficiency of cinnamaldehyde and cinnamic acid was significantly improved compared to traditional methods. Moreover, the use of the ultrasonic-microwave synergistic extraction technique demonstrated higher efficiency and lower environmental impact due to reduced waste production. The study also revealed that cinnamaldehyde and cinnamic acid in cinnamon twigs exhibited strong polarity characteristics and microwave absorption capacity, contributing to enhanced cell disruption and increased natural product release. These findings provide a robust basis for the development of an efficient and environmentally friendly extraction process for these valuable bioactive compounds.
研究领域:
化学工程
·
药学
·
环境科学
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产品关联
DOI
高影响因子
TALANTA
·
2017
·
IF 4.162
Rui Xiao,Xiaoting Zhang,Xiaona Zhang,Jiahua Niu,Minghua Lu,Xiuhua Liu,Zongwei Cai
In this article, a method for the analysis of flavors and fragrances including ethyl vanillin , trans-cinnamic acid, methyl cinnamate , ethyl cinnamate , and benzyl cinnamate in foods by HPLC with Fe 3 O 4 @GO nanocomposite as the adsorbent of magnetic solid-phase extraction was developed. The magnetic Fe 3 O 4 @GO nanocomposite was prepared and characterized by transmission electron microscope, infrared spectroscopy , X-ray diffraction and vibrating sample magnetometer. The as-prepared Fe 3 O 4 @GO nanocomposite was used as adsorbent for extraction and preconcentration of flavors and fragrances in foods. The extraction and desorption conditions including amount of materials, extraction time and desorption solvents were investigated. The analytes were separated within 10 min and detected with LODs ranged from 0.02 to 0.04 μg/mL. The recovery obtained from the analysis of spiked juice sample was between 71.5% and 112.4% with RSDs lower than 4.14%. The developed method was successfully applied to the analysis of real samples including orange juice, chocolate and fruit sugar.
研究领域:
分析化学
·
食品科学
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产品关联
DOI
PubMed
高影响因子
APPLIED CATALYSIS A-GENERAL
·
2019
·
IF 4.63
Yihu Dai,Xiaofang Chu,Jingjing Gu,Xing Gao,Min Xu,Di Lu,Xiaoyue Wan,Wei Qi,Bingsen Zhang,Yanhui Yang
The CeO 2 -supported ternary RuSnB catalysts were synthesized by incipient wetness impregnation procedures and applied in hydrogenation of cinnamaldehyde in pure water as the solvent. A synergy effect between Ru-based catalysts and water molecules has afforded the efficiently selective transformation of cinnamaldehyde to cinnamyl alcohol with the satisfactory conversion and selectivity. Structural characterization results suggested the incorporation of Ru sites into the SnO x matrix and the electronic interaction between Ru and B additives in RuSnB/CeO 2 catalyst. The isotopic exchange studies have demonstrated that both dissociative activation of H 2 and H 2 O (deuterated D 2 and D 2 O) were apparently affected by the status of Ru sites. Furthermore, the kinetics tests in D 2 O solvent have also revealed the co-existence of water-involved hydrogen-exchange route with the direct hydrogenation route using dissociative H 2 during the hydrogenation reaction. The optimal Ru 2 Sn 1 B 1 /CeO 2 catalyst could afford the best H 2 O-activation capability and thus accelerate the reaction rate in the H 2 O-involved hydrogenation.
研究领域:
催化化学
·
绿色化学
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DOI
高影响因子
METABOLIC ENGINEERING
·
2025
·
IF 6.8
Shan Yuan,Chao Xu,Miaomiao Jin,Xinglin Jiang,Wei Liu,Mo Xian,Ping Jin
Aldehydes are ubiquitous metabolites in living cells. As reactive electrophiles, they have the capacity to form adducts with cellular protein thiols and amines, leading to potential toxicity. Dynamic regulation has proven to be an effective strategy for addressing the accumulation of toxic metabolites. However, there are limited reports on applying dynamic control specifically to mitigate aldehyde accumulation. In this study, the cinnamaldehyde accumulation in the biosynthesis of cinnamylamine was used as a model to evaluate a two-way dynamic regulation strategy. First, we utilized whole-genome transcript arrays to identify the cinnamaldehyde-responsive promoters: the upregulated promoter P 4 and the downregulated promoter P d . They were then employed as biosensors to dynamically regulate the synthesis and consumption of cinnamaldehyde, mitigating its toxic effects on the host. This strategy successfully reduced cinnamaldehyde accumulation by 50% and increased the production of cinnamylamine by 2.9 times. This study demonstrated a cinnamaldehyde-induced autoregulatory system that facilitated the conversion of cinnamic acid into cinnamylamine without the need for costly external inducers, presenting a promising and economically viable approach. The strategy also serves as a reference for alleviating the inhibitory effects of other toxic aldehydes on microorganisms. Additionally, the biosensors (P d and P 4 ) can respond to a range of aldehyde compounds, offering a rapid and sensitive method for detecting toxic aldehydes in both environmental samples and microorganisms, thus provide a valuable tool for screening strains enhanced aldehyde yield.
研究领域:
合成生物学
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代谢工程
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产品关联
DOI
PubMed
高影响因子
MICROPOROUS AND MESOPOROUS MATERIALS
·
2022
·
IF 5.876
Ruyi Geng,Huanhuan Jia,Youwei Xie,Dahai Pan,Feng Yu,Binbin Fan
UiO-66 supported metal catalysts have shown high catalytic activity and selectivity to cinnamyl alcohol (COL) in the selective hydrogenation (SHYD) of cinnamaldehyde (CAL), but the roles of missing-linker defects (MLDs) in UiO-66 on the catalytic performance of the UiO-66 supported metal catalysts have less been reported. Here, UiO-66 supports with the different amount of MLDs were used as the supports, and three series of UiO-66 supported Pt (Pt/U) catalysts were prepared by sol-impregnation, wet-impregnation as well as in-situ encapsulation methods, respectively. The influences of the MLDs in UiO-66 on the catalytic properties of the prepared Pt/U catalysts in the SHYD of CAL were investigated. The series of Pt/U-720 catalysts with the more MLDs showed higher CAL conversion and selectivity to COL than the corresponding Pt/U-F catalysts with fewer MLDs. The different preparing methods affect the location and dispersion of Pt species on UiO-66 supports and the metal-support interaction, but the location of the supported Pt species on UiO-66 is the critical factor affecting the catalytic properties of Pt/U catalysts. The presence of the MLDs in UiO-66 is the key to preparing UiO-66 supported Pt catalysts with high SHYD performance.
研究领域:
催化化学
·
材料科学
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产品关联
DOI
高影响因子
JOURNAL OF CATALYSIS
·
2018
·
IF 6.759
Yihu Dai,Xing Gao,Xiaofang Chu,Chunyang Jiang,Yao Yao,Zhen Guo,Chunmei Zhou,Chuan Wang,Hongming Wang,Yanhui Yang
A series of carbon nanotube (CNT)-supported bimetallic PtFe nanoparticles were synthesized and employed as catalysts for hydrogenation of cinnamaldehyde in pure water. A synergy between water and bimetallic PtFe catalysts has allowed the efficiently selective production of cinnamyl alcohol. With the aid of water, an initial reaction rate of >1200 h −1 and a high selectivity of >97%, as well as a good cycling stability, were achieved with a Pt 3 Fe/CNT catalyst under mild reaction conditions. Isotopic labeling studies and theoretic calculation results demonstrated that the water-involved hydrogen-exchange pathway occurred with a lower energy barrier, which coexisted with the pathway of direct H 2 dissociation–hydrogenation. This work also suggested that water participated in the catalytic hydrogenation reaction by serving as a hydrogen-exchange bridge.
研究领域:
催化化学
·
绿色化学
✓ 已验证
DOI
高影响因子
Reaction Kinetics Mechanisms and Catalysis
·
2025
·
IF 1.7
Wang Yunqian,Shi Haixiang,Chen Liuyun,Su Tongming,Luo Xuan,Xie Xinling,Ji Hongbing,Qin Zuzeng
NiIn intermetallic compounds are constructed over V 2 CT x MXene for the selective hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL). Ni 4 In/V 2 CT x demonstrated a conversion rate of 93.6% for CAL, with a high selectivity of 77.4% for COL. The COL yield of Ni 4 In/V 2 CT x is much greater than that of Ni 4 In, Ni/V 2 CT x , and Ni 4 In/Al 2 O 3 . Moreover, the V 2 CT x support is the key to the formation of NiIn intermetallic compounds, which effectively inhibit the oxidation of metallic Ni. NiIn metal particles are uniformly distributed on the surface of V 2 CT x , increasing the metal‒support interaction. Electron-deficient metallic Ni and In inhibit the hydrogenation of the C=C bond. Furthermore, the introduction of In provides more abundant and stronger Lewis acid sites, facilitating the adsorption of C=O bonds and thereby enhancing the selectivity for COL.
研究领域:
材料科学
·
催化化学
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产品关联
DOI
高影响因子
MOLECULES
·
2023
·Vol. 28
·期 8
·3336
·
IF 4.6
Mengting Chen,Yun Wang,Limin Jiang,Yuran Cheng,Yingxin Liu,Zuojun Wei
Allylic alcohols typically produced through selective hydrogenation ofα,β-unsaturated aldehydes are important intermediates in fine chemical industry, but it is still a challenge to achieve its high selectivity transformation. Herein, we report a series of TiO2-supported CoRe bimetallic catalysts for the selective hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL) using formic acid (FA) as a hydrogen donor. The resultant catalyst with the optimized Co/Re ratio of 1:1 can achieve an exceptional COL selectivity of 89% with a CAL conversion of 99% under mild conditions of 140 °C for 4 h, and the catalyst can be reused four times without loss of activity. Meanwhile, the Co1Re1/TiO2/FA system was efficient for the selective hydrogenation of variousα,β-unsaturated aldehydes to the correspondingα,β-unsaturated alcohols. The presence of ReOxon the Co1Re1/TiO2catalyst surface was advantageous to the adsorption of C=O, and the ultrafine Co nanoparticles provided abundant hydrogenation active sites for the selective hydrogenation. Moreover, FA as a hydrogen donor improved the selectivity toα,β-unsaturated alcohols.Keywords:cinnamaldehyde;cinnamyl alcohol;CoRe bimetallic catalyst;selective hydrogenation;formic acid
研究领域:
化学工程
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催化化学
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DOI
PubMed
高影响因子
CATALYSIS LETTERS
·
2016
·Vol. 147
·期 1
·102-109
·
IF 2.294
Zhang Yifei,Zhang Shaohua,Pan Xiaoli,Bao Ming,Huang Jiahui,Shen Wenjie
Abstract Uniform Au particles with a mean size of 1.9 nm were initially synthesized with polyvinyl alcohol (PVA) as protecting agent, and then deposited on MgO, Al 2 O 3 , TiO 2 , Fe 2 O 3 , Co 3 O 4 , ZnO and In 2 O 3 . After calcinations at 300 °C in air to remove PVA, Au particles were highly dispersed and immobilized on all the supports, displaying narrow diameter distributions and almost identical mean sizes of 2.5–3.2 nm. The Au-oxides catalysts were further used to catalyze selective hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL). It was found that the selectivity of COL was tightly related to the acidity/basicity of the Au/oxides catalysts. The catalyst with only acidic sites such as the Au/Al 2 O 3 catalyst gave very low selectivity of COL of 15%. The catalysts with only basic sites such as Au/MgO catalyst displayed medium selectivity of COL of 52%. Interesting, the Au catalysts with both acidic and basic sites such as the Au/In 2 O 3 and Au/ZnO catalyts exhibited the highest selectivity of COL of around 86%. The synergistic cooperation of acidic sites and basic sites should be responsible for preferential adsorption and activation of the C=O group than C=C group in CAL, and then preferential hydrogenation of C=O to COL. Graphical Abstract
研究领域:
催化化学
·
材料科学
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产品关联
DOI
高影响因子
ACS Applied Materials & Interfaces
·
2024
·
IF 8.3
Xiaoying Zhao,Ruoyan Miao,Tianze Xu,Xiaolong Du,Xueyan Zhang,Wanyu Zhao,Huidong Xie,Liang Zhang,Jianzheng He,Zhenhui Ma,Hu Liu
Changeable substituent groups of organic molecules can provide an opportunity to clarify the antibacterial mechanism of organic molecules by tuning the electron cloud density of their skeleton. However, understanding the antibacterial mechanism of organic molecules is challenging. Herein, we reported a molecular view strategy for clarifying the antibacterial switch mechanism by tuning electron cloud density of cinnamaldehyde molecule skeleton. The cinnamaldehyde and its derivatives were self-assembled into nanosheets with excellent water solubility, respectively. The experimental results show that α-bromocinnamaldehyde (BCA) nanosheets exhibits unprecedented antibacterial activity, but there is no antibacterial activity for α-methylcinnamaldehyde nanosheets. Therefore, the BCA nanosheets and α-methylcinnamaldehyde nanosheets achieve an antibacterial switch. Theoretical calculations further confirmed that the electron-withdrawing substituent of the bromine atom leads to a lower electron cloud density of the aldehyde group than that of the electron-donor substituent of the methyl group at the α-position of the cinnamaldehyde skeleton, which is a key point in elucidating the antimicrobial switch mechanism. The excellent biocompatibility of BCA nanosheets was confirmed by CCK-8. The mouse wound infection model, H&E staining, and the crawling ability of drosophila larvae show that as-prepared BCA nanosheets are safe and promising for wound healing. This study provides a new strategy for the synthesis of low-cost organic nanomaterials with good biocompatibility. It is expected to expand the application of natural organic small molecule materials in antimicrobial agents.
研究领域:
有机化学
·
纳米技术
·
生物医学工程
·
材料科学
·
药学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF PHYSICAL CHEMISTRY B
·
2024
·
IF 2.8
Xin-Yu Liu,Wen-Zhu Wang,Song-Po Yao,Xue-Ying Li,Rui-Min Han,Dangquan Zhang,Zhijun Zhao,Yapei Wang,Jian-Ping Zhang
Rosemary is one of the most promising, versatile, and studied natural preservatives. Carnosic acid (CA) and carnosol (CARN), as the primary active ingredients of rosemary extracts, have little difference in structure, but their antioxidant activities vary significantly, depending on the system studied. The underlying molecular mechanisms remain unclear. By means of optical spectroscopies, stopped-flow, laser photolysis, and density functional theory (DFT) calculations, we have compared CA and CARN between their reaction dynamics of radical scavenging, metal ion chelation, and oxidation inhibition in lipid emulsion and beef, as well as between their interactions with β-carotene (β-Car). For reference, 3-isopropyl catechol (IC), which is structurally similar to the active groups of CA and CARN, was studied in parallel. It is found for CA that the intramolecular hydrogen bond can boost the acidity of its phenol hydroxyl and that the synergistic effect with β-Car can substantially enhance its antioxidation activity in the model systems of lipid and meat via the CA-to-β-Car electron transfer reaction. The substitution of A and B rings on the catechol group in both CA and CARN limits browning caused by their formation of oxidative products as antioxidants.
研究领域:
食品科学
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分子生物学
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植物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）