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ChemSusChem · 2018 ·Vol. 11 ·期 18 ·3175-3183 · IF 7.411

Biobased Benzoxazine Derived from Daidzein and Furfurylamine: Microwave-Assisted Synthesis and Thermal Properties Investigation

Jinyue Dai,Na Teng,Yunyan Peng,Yuan Liu,Lijun Cao,Jin Zhu,Xiaoqing Liu

Graphical Renewable polymers : A biobased benzoxazine resin (Dz-f) with excellent thermal properties was synthesized from daidzein and furfurylamine by using a microwave heating method. It was then cured and its thermal properties evaluated by differential scanning calorimetry (DSC), TGA, and dynamic mechanical analysis (DMA; see figure). A biobased benzoxazine resin (Dz-f) demonstrating excellent thermal properties was synthesized from daidzein and furfurylamine by using a microwave heating method. The chemical structure of synthesized benzoxazine monomer was identified by FTIR and NMR ( 1 H and 13 C NMR) before it was cured and its thermal properties evaluated by differential scanning calorimetry (DSC), TGA, and dynamic mechanical analysis (DMA). The cured resin p(Dz-f) exhibited a glass transition temperature ( T g ) of 391 °C, a very high char yield of 68.7 %, and outstanding thermal stability; the T g value obtained was the highest thermal stability value ever reported for polybenzoxazine with a high biobased content. Moreover, Dz-f demonstrated a satisfying processability, which was rare for the high-performance thermosetting resins. This work provided us with a new strategy for the preparation of high biocontent resins with excellent thermal properties. In addition, the combination of biobased feedstocks with a microwave-assisted heating method as well as the potential application of this approach in high-end fields might perpetuate remarkable progress towards the sustainable development of the polymeric industry.

研究领域: 材料科学 · 有机化学
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CHEMICAL ENGINEERING JOURNAL · 2020 · IF 10.652

Soy protein adhesive with bio-based epoxidized daidzein for high strength and mildew resistance

Chaojie Xu,Yecheng Xu,Mingsong Chen,Yi Zhang,Jianzhang Li,Qiang Gao,Sheldon Q. Shi

Soy protein based adhesives showed great potential for replacing petroleum derived formaldehyde adhesives in the commercial wood industry. However, soy protein adhesives have several problematic limitations, particularly with respect to low water and mildew resistence. As such, in order for soy protein-based adhesives to be practically applicable on an industrial level, a multi-function bio-based crosslinker that resolves both low water and mildew resistance must be designed. In this study, we synthesized a multifunctional crosslink agent (DDE) by reacting soybean-derived daidzein with epichlorohydrin (ECH) and incorporating it into soy protein to parpare a 100% bio wood adhesive with significantly improved water and mildew resistances. The results showed that by using 6 wt% DDE in the adhesive formulation, the dry and wet shear strength of plywood bonded with the SPI/DDE adhesive increased by 52.3% and 164.4%, respectively, compared with that of SPI adhesive; and was shown to be 22.3% and 69.6% higher than that of the industrially used SPI/PAE adhesive. These improvements were attributed to formation of double cross-linked network and elevated adhesive toughness. Furthermore, the resultant adhesive’s mildew resistance property were also improved with the addition of DDE, which extended the shelf life of adhesive and durability of the resultant plywood. Thus, this resultant DDE can be used to improve the mechanical properties and mildew resistance for bio-hydrogels or bio-based composites and polymers.

研究领域: 材料科学 · 生物化学
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MOLECULES · 2023 ·Vol. 28 ·期 13 ·5077 · IF 4.6

Synthesis of Daidzein and Thiophene Containing Benzoxazine Resin and Its Thermoset and Carbon Material

Zhenhao Yao,Yin Lu,Jianan Song,Kan Zhang

In this work, a novel bio-based high-performance bisbenzoxazine resin was synthesized from daidzein, 2-thiophenemethylamine and paraformaldehyde. The chemical structure was confirmed using nuclear magnetic resonance spectroscopy (NMR) and Fourier-transform infrared spectroscopy (FT-IR). The polymerization process was systematically studied using differential scanning calorimetry (DSC) and in situ FT-IR spectra. It can be polymerized through multiple polymerization behaviors under the synergistic reaction of thiophene rings with benzopyrone rather than a single polymerization mechanism of traditional benzoxazines, as reported. In addition, thermogravimetric analysis (TGA) and a microscale combustion calorimeter (MCC) were used to study the thermal stability and flame retardancy of the resulting polybenzoxazine. The thermosetting material showed a high carbon residue rate of 62.8% and a low heat release capacity (HRC) value of 33 J/gK without adding any flame retardants. Based on its outstanding capability of carbon formation, this newly obtained benzoxazine resin was carbonized and activated to obtain a porous carbon material doped with both sulfur and nitrogen. The CO2absorption of the carbon material at 0 °C and 25 °C at 1 bar was 3.64 mmol/g and 3.26 mmol/g, respectively. The above excellent comprehensive properties prove its potential applications in many advanced fields.Keywords:benzoxazine;daidzein;thiophene;CO2absorption;thermal stability

研究领域: 材料科学 · 化学工程
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POLYMER · 2026 · IF 5.1

Regulating the intrinsic thermal conductivity of daidzein-based liquid crystalline epoxy resins via spacer length

Pan Tian,Wanjing Liu,Yisen Huang,Weiyouran Hong,Junhua Zhang

The continuous advancement toward high integration of electronic devices has placed stringent, synergistic requirements on the intrinsic thermal conductivity and low-dielectric performance of packaging materials. Conventional epoxy resins exhibit extremely low intrinsic thermal conductivity, failing to meet the application demands of high-power devices. In this work, using bio-based daidzein as the rigid mesogenic, four liquid crystalline epoxy monomers with dual mesogenic units and tunable flexible alkyl spacer lengths are designed and synthesized. The monomers were cured with 4,4′-diaminodiphenyl sulfone (DDS) and the fluorinated diamine 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl (BP6FA), respectively, to systematically investigate the regulation mechanism of spacer length on the aggregated structure and properties of the materials. The results demonstrate that extending the flexible spacers significantly promotes the ordered self-assembly of mesogenic units. The stable smectic liquid crystalline structure locked in the crosslinked network after curing enables simultaneous enhancement of intrinsic thermal conductivity and optimization of dielectric properties. The optimal D10E/BP6FA system exhibits an intrinsic thermal conductivity of 0.42 W/(m·K), a low dielectric constant of 2.90 and an ultralow dielectric loss of only 0.0087 at 100 Hz, along with excellent thermal stability and thermomechanical properties. This work sheds light on the rational design of high intrinsic thermal conductivity liquid crystalline epoxy resins, and is expected to advance the high-performance application of such materials in electronic packaging.

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Applied Sciences-Basel · 2026 ·Vol. 16 ·期 18 ·8902 · IF 2.9

Terahertz Spectroscopic Characterization of a Daidzein-Piperazine Crystalline Solid Form Prepared by Liquid-Assisted Grinding

Zhipeng Wang,Haofei Sun,Hailin Cui,Shengbo Zhang,Bo Su,Cunlin Zhang

Daidzein is a natural flavonoid with low aqueous solubility and bioavailability. The low-frequency terahertz spectroscopic characteristics and corresponding vibrational origins of the 1:1 daidzein–piperazine (DAI–PIP) crystalline system remain insufficiently explored. In this study, a DAI–PIP crystalline solid form was prepared by liquid-assisted grinding at a 1:1 starting-material molar ratio and characterized using powder X-ray diffraction (PXRD), differential scanning calorimetry–thermogravimetric analysis (DSC–TGA), terahertz time-domain spectroscopy (THz-TDS), and scanning electron microscopy (SEM). The experimental PXRD pattern exhibited characteristic reflections at 18.62° and 23.19°, while several reflections of the starting materials were absent. The good overall agreement between the experimental and simulated PXRD patterns supported the reasonableness of the periodic crystal-structure models used for the subsequent THz calculations. DSC–TGA revealed distinct endothermic events and multistage mass-loss behavior, while SEM showed finer and relatively uniform particle aggregates after grinding. The DAI–PIP product exhibited experimental THz absorption features at approximately 1.46, 1.84, and 2.28 THz. Periodic DFT calculations reasonably reproduced the principal experimental features. The calculated mode at 1.89 THz was mainly localized on the hydroxyl-substituted aromatic ring of DAI, whereas the modes at 1.35 and 2.20 THz involved coupled motions of DAI and PIP accompanied by intermolecular N–H···O hydrogen-bond deformation. These results provide a structurally supported interpretation of the characteristic low-frequency vibrations of the DAI–PIP crystalline system and demonstrate the value of combining THz-TDS with periodic DFT calculations for investigating its solid-state vibrational behavior.

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COMPOSITES PART B-ENGINEERING · 2019 · IF 6.864

Synthesis of an organophosphorus flame retardant derived from daidzein and its application in epoxy resin

Chao Ma,Juan Li

For the concern of sustainable and green chemical engineering , the development of flame retardants from renewable biomaterials is particularly attractive. Daidzein is an isoflavone found in large amounts in soybeans and other legumes. The structure of daidzein permits easy reaction with flame retardant groups and is beneficial for the formation of char at high temperature. A flame retardant which can work in both the gas phase and the condensed phase may be unusually effective. An organophosphorus flame retardant (DPOD) has been prepared using daidzein and diphenylphosphinyl chloride, and used to modify the flammability of epoxy (EP) resin. The structure and flame retardant mode of action of DPOD in EP were explored. The results showed that DPOD works in both the gas phase and the condensed phase and improves the flame retardancy of EP blends greatly. In addition, the DPOD doesn't deteriorate the glass transition temperature and impact strength of EP blends. This work is a useful attempt to use biobased monomers in the design of flame retardants.

研究领域: 材料科学 · 化学工程
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CHINESE JOURNAL OF ANALYTICAL CHEMISTRY · 2017 · IF 0.795

Preparation, Characterization and Water Solubility of Inclusion Complexes of Daidzein with Amino-Modified β-Cyclodextrins

Ying-Hui DENG,Li-Na SU,Yan-Hua PANG,Ya-Fei GUO,Fen WANG,Xia-Li LIAO,Bo YANG

To improve the water solubility of daidzein, solid inclusion complexes of daidzein with two amino-modified β -cyclodextrins (ACDs), i.e., mono-6-amino-6-deoxy- β -cyclodextrin (NCD) and mono-6-ethylenediamino-6-deoxy- β -cyclodextrin (ENCD), were prepared by the saturated solution method in water with yields of 83% and 67%, respectively, under the optimized conditions including the ratio of daidzein/ACD of 3:1 and the stirring time of 72 h. The formation of the two inclusion complexes was confirmed by X-ray diffractometry (XRD) and thermo gravimetric (TG) analysis. The inclusion stoichiometry of the inclusion complexes was 1:1 from the Job plot and their complexation stability constants ( K S ) were 899.2 and 203.8 M −1 from fluorescence titration, respectively. After formation of inclusion complexes with NCD and ENCD, the water solubility of daidzein was dramatically raised to 15.2 and 13.2 mg mL −1 at 25 °C, increasing by 1800 and 1500-fold compared to native daidzein (8.31 μg mL −1 ).

CAS / MDL: 486-66-8
研究领域: 药物化学 · 材料科学 · 生物化学
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AAPS PHARMSCITECH · 2025 ·Vol. 26 ·期 2 ·60 · IF 4

Experimental and Theoretical Investigation of the Formation of Daidzein Ion-pair Compounds: Solubility, Hydrogen Bonds, Stability

Zhang Zhaoyang,Wang Sheng,Wang Qianlei,Ye Qian,Wang Wenjuan

Ion pairs represent a robust molecular force arising from the union of oppositely charged ions, held together by Coulomb attraction. Daidzein (Dai), categorized as a BCS IV drug, faces limitations in clinical application due to its relatively low solubility. To enhance the drug’s solubility, a Dai ion pair was prepared, and the mechanism underlying ion-pair formation was investigated. A comprehensive approach, combining experimental techniques and theoretical calculations, such as scanning electron microscopy, powder X-ray diffraction, differential scanning calorimetry, Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, X-ray Photoelectron Spectroscopy, and computational simulation was employed to explore the ion-pair formation mechanism. The findings indicate a significant improvement in Dai solubility through the preparation of Arg and Lys ion-pair compounds. The results revealed that the Dai–Lys ion pair exhibited more short hydrogen bonds and fewer long hydrogen bonds than did the Dai–Arg ion pair, strengthening the intermolecular interactions and improving crystal structure stability. This study effectively enhanced the solubility of Dai and offers valuable insights into the mechanisms underlying ion pair formation in ionizable drugs. Graphical

研究领域: 药学 · 药物递送 · 分子药剂学 · 晶体工程 · 计算化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2026 ·Vol. 74 ·期 29 ·22784-22797 · IF 6.7

Daidzein Prevents Stress-Induced Synaptic Plasticity Impairment and Behavioral Dysfunction via ERK/CREB/BDNF Signaling Pathway

Cheng Xin,Wang Jiaxing,Tan Haoyang,Ji Yaxin,Yu Xiaoqing,Hu Jiahuan,Li Siyao,Kang Huijie,Zhang Shuai,Xuanpan Ding,Jiao Wenjing,Fan Honggang,Zhao Yuan

Chronic stress (CS) represents a pivotal environmental trigger for depression. It induces depression-like behaviors primarily by disrupting hypothalamic–pituitary–adrenal (HPA) axis homeostasis and impairing hippocampal synaptic plasticity. Flavonoids are abundant in human diet and possess significant neuroprotective potential. We screened a library of 339 flavonoid compounds. Daidzein (DAI) was identified as the lead compound. Subsequently, in rats subjected to chronic restraint stress (CRS), DAI administration effectively ameliorated depression-like behaviors, and attenuated hippocampal histopathological damage. Network pharmacology and molecular docking analyses suggested that ERK-related signaling may be involved in the protective effects of DAI, and molecular dynamics simulations supported the stability of the DAI-ERK2 complex. Furthermore, DAI activated the ERK/CREB/BDNF signaling cascade, an effect that was partially reversed by ERK inhibitor intervention. Notably, DAI also enhanced dendritic complexity and spine density in hippocampus. In summary, our study demonstrates that DAI alleviates stress-induced synaptic plasticity damage through the ERK/CREB/BDNF signaling pathway.

CAS / MDL: 486-66-8
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RSC Advances · 2025 ·Vol. 15 ·期 33 ·26601-26607 · IF 4.6

Packed-nanofiber solid phase extraction for daidzein, genistein, glycitein in human urine and their simultaneous detection

Yuqi Dai,Lanmei Zhang,Yuemeng Wang,Anni Fu,Lanling Chu,Lei Zhao

In this work, an integrated method based on the novel packed-fiber solid-phase extraction (PFSPE) combined with high-performance liquid chromatography-ultraviolet detector (HPLC-UV) detection system was proposed for the detection of daidzein, genistein and glycitein in human urine. To efficiently adsorb three kinds of isoflavones in biological fluid, polystyrene-based nanofibers were prepared and used as adsorbents in customized solid phase extraction devices. The composition of the nanofibers, the amount of different salt ions added, the type of eluent, and the interaction of eluent volume, the amounts of nanofibers added, and the extraction time were analyzed to find the optimal adsorption conditions, respectively. The method of optimal extraction conditions for the analysis of three soy isoflavones exhibited low limits of detection (LOD) and limits of quantitation (LOQ) of 1.68–2.74 μg L−1 and 5.09–8.3 μg L−1, respectively, and spiked recovery of 95.2–107.1%, and has been successfully applied to human urine samples. This study demonstrated the potential of PFSPE as methods for the adsorption and detection of daidzein, genistein, glycitein in biological fluid concurrently, providing a valuable tool for pharmacokinetic studies and investigations into the metabolism and bioavailability of isoflavones.

研究领域: 分析化学 · 生物分析 · 药代动力学 · 代谢组学 · 纳米技术
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ELECTROANALYSIS · 2015 ·Vol. 27 ·期 7 ·1719-1725 · IF 2.138

A Novel Strategy of Electrochemically Treated ZrOCl2 Doped Carbon Paste Electrode for Sensitive Determination of Daidzein

Ying Li,Yinfeng Li,Jian Gao,Lu Wang,Lina Zou,Baoxian Ye

A novel electrochemically treated ZrOCl 2 doped carbon paste composite electrode was easily prepared by directly incorporating ZrOCl 2 into graphite powder after with an electrochemical treatment for the first time. This sensor showed sensitive voltammetric sensing for daidzein. The surface morphology and electrochemical properties of the electrode were investigated by scanning electron microscopy and cyclic voltammetry. The electrochemical behavior of daidzein was investigated in detail. Under the optimized conditions, the response currents were linearly related to daidzein concentrations in the range of 3×10 −8 to 2×10 −6 mol L −1 with a detection limit of 1×10 −8 mol L −1 in phosphate buffer solution with pH 2.5. The proposed sensor was also applied to the determination of daidzein in pueraria, pharmaceutical preparations and human uric sample with satisfactory results.

CAS / MDL: 486-66-8 13520-92-8
研究领域: 分析化学 · 药物分析
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Food Bioscience · 2025 · IF 5.9

A novel daidzein-betaine cocrystal alleviates obesity by improving lipid metabolism, modulating inflammation, and reshaping gut microbiota

Yanling Sun,Shupeng Li,Rongxin Liu,Ning Ma,Xinghua Zhao,Xin He

Daidzein (DAI) and betaine (BTN) exhibit outstanding therapeutic effects on the treatment of obesity and lipid-related diseases. However, the low solubility and oral bioavailability of DAI, along with the poor stability of BTN, limit the clinical application of both compounds. Here, a novel 1:2 drug-drug cocrystal of daidzein and betaine (DAI-BTN) was successfully prepared using crystal engineering technology. Dynamic vapor sorption analysis showed that the mass change of DAI-BTN was reduced by 58% in a relatively humidity range of 0% to 95% compared to BTN. As compared to pure DAI, the intrinsic dissolution rate and the bioavailability of DAI-BTN were enhanced by 4.34-fold and 3.73-fold, respectively. Furthermore, the effect and mechanisms of DAI-BTN in a mouse model of diet-induced obesity were explored. The results showed that the DAI-BTN can reduce body weight and adipocyte area, which were negatively correlated with the levels of TG, TC, LDL-C, AST, ALT, TNF-α, IL-1β and IL-6. Particularly, DAI-BTN was associated with improving the diversity, structure, and composition of the gut microbiome, promoted the growth of beneficial bacteria (e.g., Proteobacteria and Akkermansia ) and inhibited the proliferation of harmful bacteria (e.g., Desulfovibrio and Flexispira ). Therefore, DAI-BTN hold great promise to be developed as an effective drug combination agent for the alleviation of obesity.

研究领域: 药理学 · 代谢生物学 · 微生物学
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