FOOD RESEARCH INTERNATIONAL
·
2024
·
IF 7
Jing Wei,Jingtao Cui,Yanchi Zhou,Tong Li,Qiaozhu Wei,Tian Li,Weimin Zhang
The effects of cis – trans isomerization on the oxidation products of oleic acid (composites and structure characterization) were investigated. The reduction of thermal oxidation reaction of methyl elaidate (ME) was 6.72 % lower than that of methyl oleate (MO), and the oxidation products (core aldehydes) first increased and then decreased with the prolongation of thermal oxidation time. ME exhibited better oxidation stability than MO in free radicals, hydroperoxides, double bonds, aldehydes, and glycerides. The oxidation products were mainly 11-oxo-9-undecenoate (initial stage) and methyl 9-oxononanoate (later stage), following the free radical chain reaction mechanism. The H8 in double bond was more easily dehydrogenated in the chain initiation stage than H11, followed by the formation of core aldehyde through three intermediates and two transition states each pathway. ME required a higher energy barrier (1.3–13.6 kJ/mol) than MO reaction, making it more difficult for ME to undergo thermal oxidation reaction. The transition state 4 and 5 were rate determining steps of chain initiation reaction and proliferation reaction, respectively. This study was of great significance to further control the formation of these trans fats and their oxidation products.
研究领域:
食品科学
·
化学动力学
·
脂质氧化
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DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2023
·Vol. 103
·期 7
·3489-3500
·
IF 4.1
Yihang Liu,Qingzhi Wang,Chen Liu,Haonan Yang,Li Jia,Litao Zhao,Fayong Gong,Chen Tan,Hongxun Tao,Wen-Sen He
BACKGROUND Oxidation is a major problem for oils and fats, which can be mitigated by antioxidants. Rutin has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. In this study, an efficient enzymatic synthesis route of lipophilic rutin ester was established using oleic acid as an acyl donor, and the antioxidant potential of rutin oleate was evaluated for the first time by proton ( 1 H) nuclear magnetic resonance (NMR) spectroscopy. RESULTS The synthesized product was finally identified as rutin oleate by Fourier transform infrared, high-performance liquid chromatography–mass spectrometry, and 1 H, carbon-13, and DEPT-135 NMR analyses, and the acylation site was the 4‴-OH of the rhamnose group in the rutin molecule. The maximum conversion was over 93% after 48 h of reaction using Novozym 435 as catalyst under the best conditions among these tests. The conversion of rutin ester decreased with the increase of carbon chain length and the number of carbon–carbon double bonds of the fatty acid molecule. Most importantly, rutin oleate exhibited antioxidant capacity comparable to butylated hydroxytoluene and its counterparts (rutin and oleic acid) at low temperatures (60° C), but had a significant advantage at high temperatures (120° C). CONCLUSION The antioxidant activity of rutin was significantly enhanced by lipase-mediated esterification with oleic acid. Therefore, rutin oleate could be further developed as a novel antioxidant for use in oil‑ and fat-based foods. © 2023 Society of Chemical Industry.
研究领域:
食品科学
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生物化学
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分析化学
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产品关联
DOI
PubMed
高影响因子
TRANSACTIONS OF TIANJIN UNIVERSITY
·
2024
·
IF 6.7
Meng Zhaohui,Liao Ying,Liu Ling,Li Yaqian,Yan Hao,Feng Xiang,Chen Xiaobo,Liu Yibin,Yang Chaohe
Improving the efficiency of metal/reducible metal oxide interfacial sites for hydrogenation reactions of unsaturated groups (e.g., C=C and C=O) is a promising yet challenging endeavor. In our study, we developed a Pd/CeO 2 catalyst by enhancing the oxygen vacancy (O V ) concentration in CeO 2 through high-temperature treatment. This process led to the formation of an interface structure ideal for supporting the hydrogenation of methyl oleate to methyl stearate. Specifically, metal Pd 0 atoms bonded to the O V in defective CeO 2 formed Pd 0 –O V –Ce 3+ interfacial sites, enabling strong electron transfer from CeO 2 to Pd. The interfacial sites exhibit a synergistic adsorption effect on the reaction substrate. Pd 0 sites promote the adsorption and activation of C=C bonds, while O V preferably adsorbs C=O bonds, mitigating competition with C=C bonds for Pd 0 adsorption sites. This synergy ensures rapid C=C bond activation and accelerates the attack of active H* species on the semi-hydrogenated intermediate. As a result, our Pd/CeO 2 -500 catalyst, enriched with Pd 0 –O V –Ce 3+ interfacial sites, demonstrated excellent hydrogenation activity at just 30 °C. The catalyst achieved a Cis–C18:1 conversion rate of 99.8% and a methyl stearate formation rate of 5.7 mol/(h·g metal ). This work revealed the interfacial sites for enhanced hydrogenation reactions and provided ideas for designing highly active hydrogenation catalysts.
研究领域:
催化化学
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材料科学
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产品关联
DOI
高影响因子
ACS Omega
·
2020
·
IF 2.87
Xiaobing Chen,Zhenhua Li,Yuan Chun,Fan Yang,Haocheng Xu,Xingcai Wu
Many researchers reported that a sigmoid kinetic curve was obtained in oil transesterification with methanol catalyzed by CaO and gave different explanations for this formation. In this paper, heterogeneously catalyzed transesterification of soybean oil with methanol using CaO has been investigated. The solid catalyst and the liquid reaction mixture under different reaction time periods were characterized by X-ray diffraction (XRD), Fourier transform infrared (FT-IR) spectroscopy, and high-performance liquid chromatography (HPLC) to reveal the formation of an S-shape kinetic curve. The appearance of calcium hydroxide, calcium methoxide, calcium glyceroxide, fatty acid calcium, diglycerides, and monoglycerides and their contributions to the kinetic curve have been discussed. The low reaction rate in the induction period can be attributed to mass transfer in this three-phase system. However, the formation of surfactants, diglycerides and monoglycerides, promotes the emulsification of the reaction mixture and numerous emulsion reactors are generated. These emulsion reactors can improve the contact of the solid catalyst with the reactants and thus accelerate the reaction.
研究领域:
化学工程
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催化反应
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产品关联
DOI
PubMed
高影响因子
TRIBOLOGY LETTERS
·
2023
·Vol. 71
·期 4
·1-11
·
IF 3.2
Tang Qiong,Zhao Zhiping,Li Ting,Ge Leizhen,Xu Hong,Liu Lei,Dong Jinxiang
A novel dual-functional group base oil was synthesized by alkylation of methyl oleate from biomass and tetralin from coal chemical industry. Interestingly, the monoalkylated product (MOAT) exhibited low pour point, high flash point, and viscosity index compared with the traditional alkyl aromatic lubricating oil (AN5), owing to the combination of the naphthenic aromatic (tetralin) and the methyl oleate framework. MOAT as co-base oil with PAO8 was studied to prepare lithium-based greases for the first time, and their rheological and tribological properties were evaluated in detail. The microstructure of the MOAT-based grease displayed high entanglement of lithium fiber. The 20% MOAT-based grease markedly reduced friction and wear compared with PAO8-based grease and 20% AN5-based grease. The excellent tribological performances were attributed to the strong interaction between the ester group and the soap fiber that provides more relative elasticity of grease and improves tribological behavior. Our finding clearly demonstrated that MOAT had the potential as a new class of base oil for obtaining high-performance lithium grease. Graphical Abstract
研究领域:
化学工程
·
材料科学
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DOI
高影响因子
ADVANCES IN POLYMER TECHNOLOGY
·
2019
·
IF 2.663
Anping Wang,Heng Zhang,Hu Li,Song Yang
Biomass-based polymers are eco-friendly, nontoxic and biodegradable materials. In this work, in order to prepare green, low-cost and high-efficient catalysts under mild conditions, we chose biomass-based chitosan as raw material and prepared a new solid acidic catalyst by an acid functionalization method. FT-IR, XRD, SEM, TGA, BET, neutralization titration and other analytical methods were used to characterize the catalyst. The results showed that CS-SO3H morphology exhibited a sphere of about 10 μm diameter, and the acid density was as high as 3.81 mmol/g. The catalyst exhibits good catalytic activity in the esterification of oleic acid and methanol, which is a model reaction of the pre-esterification process in the preparation of biodiesel from feedstocks with high acid values. Under the optimum reaction conditions (15/1 methanol/oleic acid mole ratio and 3 wt% catalyst dosage at 75°C for 3 h), the yield of methyl oleate can reach 95.7%. Even if the mass of oleic acid in the reactant increased to 20 g, solid acid showed good catalytic performance, and the yield of methyl oleate was 94.4%. After four times of reuse, the yield of the catalyst can still reach 85.7%, which indicates that the catalyst has good catalytic activity and stability, and has potential application prospects.
研究领域:
化学工程
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可再生资源
·
催化材料
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产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF PHARMACEUTICS
·
2018
·
IF 3.862
Wei Dong,Xiuhua Wang,Chang Liu,Xiao Zhang,Xin Zhang,Xianzhi Chen,Yongqiang Kou,Shirui Mao
In the present study, chitosan based polymer-lipid hybrid nanoparticles (PLNs) were prepared by a self-assembly method and their use as the carrier for oral absorption enhancement of enoxaparin was evaluated. The enoxaparin-loaded nanoparticles were composed of chitosan as the polymer and glyceryl monooleate as the lipid with a lipid/polymer mass ratio ranging from 0 to 0.3, and F127 was added as a stabilizer. It was found that the PLNs showed a higher surface hydrophobicity but mucoadhesive properties similar to those of chitosan based nanocomplexes. Results from DSC experiments and NMR solvent relaxation study indicate that glyceryl monooleate was completely incorporated into the nanoparticles and the lipid/polymer ratio affected the extent of lipid-polymer interaction inside the nanoparticles and the resultant internal structures. The stability of the PLNs in simulated gastrointestinal fluids was also affected by the lipid/polymer ratio; the best stability was shown by nanoparticles with a lipid/polymer ratio of 0.2. Nanoparticles with the optimal composition significantly enhanced the oral bioavailability of enoxaparin with a 4.5-fold increase in AUC in comparison with a solution of enoxaparin. In conclusion, GMO/CS based PLNs can provide a new insight to develop orally applicable delivery system for hydrophilic macromolecules. Their absorption can be enhanced with proposed PLNs and preparation of this PLNs was also found to be easy comparing to other similar methods.
研究领域:
药剂学
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生物材料
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药物递送系统
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产品关联
DOI
PubMed
高影响因子
Journal of Materials Chemistry B
·
2014
·Vol. 3
·期 2
·316-322
·
IF 0
Wen-Xing Gu,Mingran Zhu,Nan Song,Xiaoxu Du,Ying-Wei Yang,Hui Gao
A series of linear and star-shaped amphiphilic polyethylene glycol block polylactide (PEG-b-PLA) and β-cyclodextrin (CD) conjugated PEG-b-PLA (PEG-b-PLA-CD) copolymers were synthesized. Bovine serum albumin (BSA) aqueous solution was emulsified in the copolymer organic solutions to fabricate reverse micelles (RMs), and was then further transferred into ethyl oleate (EO), a pharmaceutically acceptable vehicle, by the RMs. As identified by 1H NMR, the RMs were formed with a hydrophilic core of PEG and CD, covered with a hydrophobic corona of PLA moiety, and were spherical in shape, as observed by a scan electronic microscope. Compared with the PEG-b-PLA RMs, the PEG-b-PLA-CD RMs presented higher encapsulation efficiency. The release of BSA was influenced by the copolymer composition and architecture. BSA stability in the release aqueous phase was confirmed by circular dichroism spectroscopy. The oil-based formulation fabricated from biodegradable copolymers with high drug loading showed a great potential for protein delivery.
研究领域:
生物材料
·
药物递送
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产品关联
DOI
PubMed
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
·
2014
·Vol. 92
·期 1
·133-140
·
IF 1.62
Wang Aili,Chen Li,Xu Fan,Yan Zongcheng
Glycerol trioleate-based ionic liquid microemulsions are promising biolubricant alternatives. This study presents the formation and the phase behavior of glycerol trioleate-based ionic liquid microemulsions. Areas of the single-phase domain were calculated to illustrate the phase-forming capacities of the designed systems. The effects of ionic liquid anions and cations, oxyethylene groups’ number of surfactant, mass ratio of surfactant to co-surfactant, chain length of co-surfactant, and temperature on the phase behavior and phase-forming capacities of glycerol trioleate-based ionic liquid microemulsions were investigated using pseudo-ternary phase diagrams. The results showed that the phase-forming capacities of glycerol trioleate-based ionic liquid microemulsions with different ionic liquids were Tf 2 N − -based > PF 6
− -based > BF 4
− -based, OMIM + -based > HMIM + -based > BMIM + -based > EMIM + -based. The designed systems contained ionic liquid-glycerol trioleate amphiphilic balance; thus, glycerol trioleate-surfactant micelles achieved the maximum solubilization capacity for the ionic liquid when the surfactant had approximately five oxyethylene groups with a surfactant to co-surfactant mass ratio of 4:1. Moreover, increasing the temperature and the aliphatic chain length of co-surfactant from C2 to C6 enhanced the ability of glycerol trioleate and ionic liquids to form microemulsions.
研究领域:
化学
·
材料科学
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DOI
高影响因子
MICROPOROUS AND MESOPOROUS MATERIALS
·
2022
·
IF 5.876
Xiu Gao,Yingqi Zhang,Yanping Hong,Beining Luo,Xianzai Yan,Guoqiang Wu
Methyl oleate (MO) macromolecules are unable to access the microporous channel of conventional titanium silicalite-1 (TS-1) zeolite , which leads to the low catalytic activity of epoxidation of MO. Herein, the small-size TS-1 (TS-1-s) zeolite with a large surface area was synthesized successfully through steam-assisted crystallization, and then a novel blocked TS-1-s supported molybdenum (Mo/TS-1-bs) catalysts were prepared for efficient epoxidation of MO with clean H 2 O 2 to produce epoxidized methyl oleate (EMO). Various characterization results show the introduced Mo species are highly dispersed on the outer surface of TS-1-s without destroying the structure of the MFI type zeolite and the tetrahedral framework titanium (Ti 4+ ). Interestingly, a large number of Mo 6+ species exhibit certain epoxidation activity attributing to the generating of electrophilic molybdenum hydroperoxide (Mo–OOH) species via Mo species combined with H 2 O 2 , which could adsorb and react easily with MO molecules. Furthermore, the Mo species are also coordinated with Ti 4+ species through the O atom resulting in the facile attack of the Ti–O bonds by H 2 O 2 and easy to form an active intermediate. Therefore, compared with the conventional TS-1, the Mo/TS-1-bs shows higher catalytic activity in the epoxidation reaction. However, the acidity of Mo/TS-1-bs catalysts increases with increasing the Mo-loading owing to the formation of Lewis acid, which leads to the side reactions and the decrease of EMO selectivity. As a consequence, the efficient, non-corrosive and green catalytic system for epoxidation of MO was developed, and the activity improvement of Mo species and the influence of acid were also demonstrated.
研究领域:
催化化学
·
材料科学
·
绿色化学
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产品关联
DOI
高影响因子
ACS Applied Materials & Interfaces
·
2015
·
IF 6.723
Limei Li,Yi Zuo,Qin Zou,Boyuan Yang,Lili Lin,Jidong Li,Yubao Li
To improve the mechanical properties of bone tissue and achieve the desired bone tissue regeneration for orthopedic surgery, newly designed hydroxyapatite/polyurethane (HA/PU) porous scaffolds were developed via in situ polymerization. The results showed that the molecular modification of PU soft segments by glyceride of castor oil (GCO) can increase the scaffold compressive strength by 48% and the elastic modulus by 96%. When nano-HA (n-HA) particles were incorporated into the GCO–PU matrix, the compressive strength and elastic modulus further increased by 49 and 74%, from 2.91 to 4.34 MPa and from 95 to 165.36 MPa, respectively. The n-HA particles with fine dispersity not only improved the interface bonding with the GCO–PU matrix but also provided effective bioactivity for bonding with bone tissue. The hierarchical structure and mechanical quality of the n-HA/GCO–PU composite scaffold were determined to be appropriate for the growth of cells and the regeneration of bony tissues, demonstrating promising prospects for bone repair and regeneration.
研究领域:
生物材料学
·
组织工程学
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DOI
PubMed
高影响因子
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
·
2017
·
IF 3.756
Ning Li,Peng Quan,XiaoCao Wan,Chao Liu,Xiaochang Liu,Liang Fang
In this paper, based on the optimized formulation of olanzapine (OLN) transdermal patch, the role of sorbitan monooleate (SP) in OLN release and percutaneous absorption processes was probed in vitro and in vivo . Rheological test, DSC , FT-IR and molecular modeling were conducted to elucidate the effect of SP on the release process of OLN from transdermal patch . Additionally, the action of SP on the percutaneous absorption process was probed using tape stripping transdermal experiment, confocal laser scanning microscopy (CLSM), ATR-FTIR and molecular docking. The results showed that the hydrogen bonding interaction between OLN and pressure sensitive adhesive (PSA) was weakened by SP, which resulted in a decrease in the cohesive interaction between polymer chains and an increase in the formation of free volume of PSA, thus, the release of OLN from patch was promoted. Meanwhile, the O H groups of SP interacted with the polar head groups of the ceramides , which increased the fluidity of the skin lipids , thereby improved the ability of OLN percutaneous absorption. In summary, this study demonstrated that not only the release but also the percutaneous absorption processes were promoted by SP. This study provided comprehensive molecular level understanding on the effect of penetration enhancer on transdermal patch and strategies for rationally selection of chemical enhancer for transdermal drug delivery systems .
研究领域:
药剂学
·
分子生物学
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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）