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Oleic Acid
Materials Today Chemistry · 2023 · IF 7.3

In-situ formation of oleic acid amide ligand boosts persistent luminescence of zinc gallate nanoparticles toward efficient latent fingermark detection

T. Hu,H. Cheng,D. Yang,K. Shao,Y. Teng,Z. Pan

Cr 3+ -doped zinc gallate (ZnGa 2 O 4 :Cr 3+ , ZGOC) nanomaterials feature with near-infrared emission and long afterglow properties. However, simultaneously controlling nanoparticle size and afterglow performance of ZGOC remains very challenging. A novel organic amine-stimulated solvothermal synthesis method for preparing ZGOC nanoparticles was demonstrated in this paper. Controllable synthesis of ZGOC nanoparticles was realized for uniform particle size distribution and excellent afterglow properties via adding different amines in organic phase system. Among them, by the triethylamine-stimulated solvothermal method, ZGOC nanoparticles are subsphaeroidal and narrow size distributed with an average particle size of about 11 nm. The near-infrared luminescence intensity of the nanoparticles was enhanced more than 7 times. The underneath organic amines stimulation mechanism was clarified as the in-situ formation of oleic acid amide ligand, consequently, enhancing the afterglow properties via combination results of surface defects passivation and ligand antenna effect. Furthermore, uniform particle size distribution and excellent afterglow properties make the prepared nanoparticles show great visualization in latent fingermark detection. The current finding of in-situ formation of oleic acid amide ligand offers guidance for the controllable synthesis of nanoparticles by the organic amines-stimulated solvothermal method.

CAS / MDL: 108503-47-5 14783-68-7
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ENDOCRINE · 2019 ·Vol. 64 ·期 3 ·512-524 · IF 3.296

Oleic acid protects insulin-secreting INS-1E cells against palmitic acid-induced lipotoxicity along with an amelioration of ER stress

Liu Xiaohong,Zeng Xin,Chen Xuanming,Luo Ruixi,Li Linzhao,Wang Chengshi,Liu Jingping,Cheng Jingqiu,Lu Yanrong,Chen Younan

Purpose It is demonstrated that unsaturated fatty acids can counteract saturated fatty acids-induced lipotoxicity, but the molecular mechanisms are unclear. In this study, we investigated the protective effects of monounsaturated oleic acid (OA) against saturated palmitic acid (PA)-induced cytotoxicity in rat β cells as well as islets, and mechanistically focused on its regulation on endoplasmic reticulum (ER) stress. Methods Rat insulinoma cell line INS-1E cells and primary islets were treated with PA with or without OA for 24 h to determine the cell viability, apoptosis, and ER stress. SD rats were fed with high-fat diet (HFD) for 16 w, then, HFD was half replaced by olive oil to observe the protective effects of monounsaturated fatty acids rich diet. Results We demonstrated that PA impaired cell viability and insulin secretion of INS-1E cells and rat islets, but OA robustly rescued cells from cell death. OA substantially alleviated either PA or chemical ER stressors (thapsigargin or tunicamycin)-induced ER stress. Importantly, OA attenuated the activity of PERK-eIF2α-ATF4-CHOP pathway and regulated the ER Ca 2+ homeostasis. In vivo, only olive oil supplementation did not cause significant changes, while high-fat diet (HFD) for 32 w obviously induced islets ER stress and impaired insulin sensitivity in SD rats. Half replacement of HFD with olive oil (a mixed diet) has ameliorated this effect. Conclusion OA alleviated PA-induced lipotoxicity in INS-1E cells and improved insulin sensitivity in HFD rats. The amelioration of PA triggered ER stress may be responsible for its beneficial effects in β cells.

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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2019 · IF 3.375

Self-Pillared ZSM-5-Supported Ni Nanoparticles as an Efficient Catalyst for Upgrading Oleic Acid to Aviation-Fuel-Range-Alkanes

Fuxiang Feng,Li Wang,Xiangwen Zhang,Qingfa Wang

HZSM-5 zeolite has been extensively utilized in the petrochemical and fine chemical industry owing to its excellent isomerization/cracking activity and hydrothermal stability. However, it still remains a great challenge for ZSM-5-supported catalysts to upgrade vegetable oils to aviation-fuel-range-alkanes (AFRAs). Herein, an efficient Ni/ZSM-5 catalyst composed of self-pillared (SP) nanosheets along with high external acid fraction and short characteristic diffusion length was synthesized and employed for this reaction. This SP Ni/ZSM-5 nanosheet catalyst shows high deoxygenation, cracking/isomerization activity, and excellent catalytic stability for upgrading oleic acid to AFRAs, which is attributed to the SP nanosheet structure and reasonable acid distribution. Last, a high AFRA yield of 40% with an iso/n-alkanes ratio of 1.8 was achieved.

CAS / MDL: 112-80-1
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Materials Research Express · 2018 ·Vol. 5 ·期 6 ·065316 · IF 1.151

Comparative study of reinforcement of Nano-SiO2 modified by poly(propylene glycol) phosphate ester versus oleic acid for waterborne polyurethane

Xiaoyan Gao,Yu Mao,Lingli Ni,Xiufang Zhu,Suqin Zhou,Shan Yun,Kun Hong,Jinquan Wang

In this work, in order to improve the dispersion and reinforcement of waterborne polyurethane (WPU), nano-SiO2 was modified with a amphiphilic polymeric surfactant poly(propylene glycol) phosphate (PPG Phosphate) and oleic acid for comparison, then incorporated into WPU through in situ polymerization. The results show that both of the PPG phosphate and oleic acid were successfully grafted onto nano-SiO2 surface and significantly improved its hydrophobic property. Scanning electron microscopy (SEM) observation reveals that PPG phosphate modified SiO2 nanoparticles had good compatibility with WPU and uniformly dispersed into WPU matrix. The results also show that the tensile strength, water resistance and thermal stability were all significantly improved by incorporation of nano-SiO2, especially PPG phosphate modified SiO2, which was attributed to its good dispersion in WPU and strong interface adhesion.

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NEW JOURNAL OF CHEMISTRY · 2024 ·Vol. 48 ·期 35 ·15512-15523 · IF 2.7

The L-lysine-assisted synthesis of a nano-ZSM-5 zeolite as a catalyst for oleic acid pyrolysis to BTX

Sen Fu,Hanxu Guo,Hong Yuan

A nano-ZSM-5 zeolite having a hierarchical pore structure was synthesized using L-lysine as a mesopore template and growth inhibitor. The effects of the L-lysine/Si and Si/Al molar ratios on the morphology and pore structure of the zeolite were studied. The products were characterized by scanning electron microscopy, transmission electron microscopy and N2-Brunauer–Emmett–Teller surface area analysis. These assessments showed that the particle size of the ZSM-5 zeolite could be reduced to 60 nm with a surface area as high as 395 m2 g−1 and a high density of mesopores. These zeolites were applied to the catalytic pyrolysis of oleic acid in a fixed-bed reactor to generate benzene, toluene and xylenes (BTX). At a reaction temperature of 500 °C, the catalyst having L-lysine/Si and Si/Al ratios of 0.4 and 30, respectively, gave a BTX yield of 27.4 wt%. This yield decreased with increases in the Si/Al ratio whereas varying the L-lysine/Si ratio did not produce a specific trend. The spent catalyst was characterized by thermogravimetric analysis and exhibited superior anti-coking ability and longer catalytic lifetime compared with a standard ZSM-5 zeolite.

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FOOD CHEMISTRY · 2024 · IF 8.5

Oleic acid treatment of rice grains reduces the starch digestibility: Formation, binding state and fine structure of starch-lipid complexes

Qian Gao,Ran Feng,Meng-Jie Yu,Han Tao,Bao Zhang

Rice contains abundant starch and contributes to a rapid rise in postprandial blood glucose levels. Hence, it is crucial to directly modify rice grains for resistant starch (RS) content elevation while preserving their morphology. In this study, rice grains were treated with 6%–18% concentrations of oleic acid (OA) and 8–20 h of soaking time to promote the formation of starch-lipid complexes, thereby reducing rice digestibility. In OA-treated rice, the OA molecules exist in three binding states. OA-treated rice exhibited a significantly higher complexation index and OA content than natural rice. RS content increased from 20.50% to 32.46%. X-ray diffraction and NMR spectroscopy revealed the development of amylose-OA complexes within the rice grains and a V-crystalline structure of up to 3.62%. Raman spectroscopy and thermogravimetric analysis showed enhanced molecular ordering and structural stability of rice starch. Overall, OA treatment effectively promotes RS formation within rice grains, consequently reducing rice digestibility.

CAS / MDL: 112-80-1
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Minerals · 2021 ·Vol. 11 ·期 1 ·58 · IF 2.644

Effect of Dodecane-Oleic Acid Collector Mixture on the Evolution of Wetting Film between Air Bubble and Low-Rank Coal

Yinfei Liao,Xingwei Song,Maoyan An,Zhe Yang,Xiaodong Hao,Hourui Ren

The wetting film evolution process is essential for flotation, especially in bubble–particle attachment. A mixed collector has been proved effective in promoting flotation. In this paper, the effect of a mixed collector (MC) composed by n-dodecane (D) and oleic acid (OA) on wetting film evolution was investigated using the extended Derjagin–Landau–Verwey–Overbeek (EDLVO) theory, the Stefan–Reynolds model, induction time, and zeta potential measurement. The hydrophobic force constant between bubble and coal treated by different collectors was analyzed. The results showed that MC was superior in reducing the induction time and increasing the zeta potential. When bubbles interacted with coal treated by MC, they had relatively low interaction energy, high critical film thickness, and high drainage rate. The order of hydrophobic force constant was no reagent < D < OA < MC. It indicated that the hydrophobic interaction between bubbles and coal particles treated by MC was the strongest because of the synergistic effect of D and OA.Keywords:wetting film;EDLVO theory;Stefan–Reynolds model;collector;hydrophobic force constant

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Pharmaceutics · 2020 ·Vol. 12 ·期 7 ·680 · IF 4.421

Oleic Acid Copolymer as A Novel Upconversion Nanomaterial to Make Doxorubicin-Loaded Nanomicelles with Dual Responsiveness to pH and NIR

Jin Zhang,Xiaoyue Tang,Chuanqing Huang,Zeyu Liu,Yong Ye

Oleic acid (OA) as main component of plant oil is an important solvent but seldom used in the nanocarrier of anticancer drugs because of strong hydrophobicity and little drug release. In order to develop a new type of OA nanomaterial with dual responses to pH and near infrared light (NIR) to achieve the intelligent delivery of anticancer drugs. The novel OA copolymer (mPEG-PEI-(NBS, OA)) was synthesized by grafting OA ando-nitrobenzyl succinate (NBS) onto mPEGylated polyethyleneimine (mPEG-PEI) by amidation reaction. It was further conjugated with NaYF4:Yb3+/Er3+nanoparticles, and encapsulated doxorubicin (DOX) through self-assembly to make upconversion nanomicelles with dual response to pH and NIR. Drug release behavior of DOX, physicochemical characteristics of the nanomicelles were evaluated, along with its cytotoxic profile, as well as the degree of cellular uptake in A549 cells. The encapsulation efficiency and drug loading capacity of DOX in the nanomicelles were 73.84% ± 0.58% and 4.62% ± 0.28%, respectively, and the encapsulated DOX was quickly released in an acidic environment exposed to irradiation at 980 nm. The blank nanomicelles exhibited low cytotoxicity and excellent biocompatibility by MTT assay against A549 cells. The DOX-loaded nanomicelles showed remarkable cytotoxicity to A549 cells under NIR, and promoted the cellular uptake of DOX into the cytoplasm and nucleus of cancer cells. OA copolymer can effectively deliver DOX to cancer cells and achieve tumor targeting through a dual response to pH and NIR.

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LWT-FOOD SCIENCE AND TECHNOLOGY · 2024 · IF 6

Oleic acid and whey protein reduced the digestion of oxidized and/or hydroxypropyl starches by changing their properties and microstructure

Jing Sun,Shuang-yi Zheng,Hai-long Zhang,Run-jiao Zhang,Shen-sheng Xiao,Xue-dong Wang,Jing Du

Fatty acids and protein play a crucial role in reducing starch digestion. To investigate the effect of oleic acid (OA) and whey protein (WP) on the digestion of oxidized and/or hydroxypropyl starches and its mechanism, the changes on digestion, properties and microstructure of starch before and after complexation with OA and WP were analyzed using rapid viscosity analyzer (RVA), rheometer, scanning electron microscope (SEM), Fourier transformation infrared spectroscopy (FT-IR) and X-ray diffractometer (XRD). Results showed that starches with OA and WP showed cooling peaks in RVA curve due to starch-OA-WP complexes formation. Additionally, OA and WP had synergistic effects on the increase of storage modulus (G′), the decrease of gel pore size and digestion of starches. OA and WP had a greater effect on digestion of oxidized hydroxypropyl starch (OHPS) than that of hydroxypropyl starch (HPS) and oxidized starch (OS). Specifically, resistant starch content in HPS, OS and OHPS was increased by 82.41%, 58.67% and 279.18%, respectively, due to OA and WP incorporation. This was attributed to the decrease of solubility and increase of order degree of OHPS caused by OA and WP. Therefore, the appropriate hydrophilic and lipophilic properties of OHPS was helpful to complex with OA and WP.

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FUEL PROCESSING TECHNOLOGY · 2019 · IF 4.507

Citric-acid-induced mesoporous SAPO-11 loaded with highly dispersed nickel for enhanced hydroisomerization of oleic acid to iso-alkanes

Lingmei Yang,Shiyou Xing,Hongzhe Sun,Changlin Miao,Ming Li,Pengmei Lv,Zhongming Wang,Zhenhong Yuan

In this study, a series of Ni/SAPO-11 catalysts with different Ni loadings were prepared by citric acid-assisted impregnation for the hydroisomerization of oleic acid to iso-alkanes. Serving as a chelating ligand, citric acid first promoted the dispersion of Ni nanoparticles loaded on SAPO-11. Because of its acid properties, citric acid facilitated the removal of aluminium oxide species, contributing to the formation of a mesoporous SAPO-11 structure. A maximum of 67.3 mol% of iso-alkanes was formed using 7Ni/SAPO-11 as a catalyst under optimal conditions of 360 °C, 4 h, and 4.0 MPa H 2 . After reusing for five cycles, the catalyst still exhibited 21.5 mol% isomer selectivity. The reaction pathways and catalytic mechanisms concerning the oleic acid hydroisomerization process were proposed and discussed. The hydroisomerization of oleic acid mainly depended on the catalyst's Lewis acid sites, with the assistance of the metal centre and Brönsted acid sites. The mesoporous structure of SAPO-11 facilitated the availability of a significant number of catalytic Lewis acid sites, which, together with the highly dispersed Ni centres, contributed to the enhanced product isomerization.

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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2025 ·Vol. 105 ·期 7 ·3931-3941 · IF 3.5

Selective synthesis of triacylglycerols by the ADS-17-supported Candida antarctica lipase B through esterification of oleic acid and glycerol

Jiawei Zheng,Qiangyue Zhang,Nanjing Zhong

BACKGROUND Immobilized enzyme possessing both high activity and good selectivity is important in practice. In this study, Candida antarctica lipase B (CALB) was immobilized onto the macroporous resin ADS-17 for triacylglycerol (TAG) synthesis through esterification of oleic acid and glycerol. The reaction conditions were optimized by single-factor study and orthogonal test, and the reusability of the immobilized CALB (CALB@ADS-17) was evaluated. In addition, the mechanism of lipase immobilization was studied and the catalytic mechanism of CALB@ADS-17 was investigated. RESULTS Oleic acid conversion up to 99.20% and TAG content at 91.58 wt% could be obtained under optimal conditions. In addition, the CALB@ADS-17 retained 84.28% of its initial activity after 11 cycles of reuse. The mechanism of lipase immobilization was through hydrophobic adsorption. The relationship between temperature and oleic acid conversion was ln V 0 = 6.3316 − 4.3321/ T , and the activation energy ( E a ) was 36.02 kJ mol −1 . CALB@ADS-17 did not exhibit an obvious interfacial activation phenomenon. Its kinetic behavior can be described by the Michaelis–Menten model, whose kinetic parameters of v max , k cat , K m , K i , and k ca t /K m were 0.01265 μmol L −1 s −1 , 9310.72 s −1 , 0.4907 mmol L −1 , 3.997 mmol L −1 , and 1.90 × 10 4 L mmol −1 s −1 , respectively. CONCLUSION CALB@ADS-17 showed good esterification performance and exhibited good selectivity towards TAG generation. In addition, CALB@ADS-17 exhibited good reusability in esterification reactions and has potential in practical applications. © 2025 Society of Chemical Industry.

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WATER AIR AND SOIL POLLUTION · 2026 ·Vol. 237 ·期 22 ·1284 · IF 3.5

Assessment of Pyrethroid Accumulation and Compartmental Distribution in a Zebrafish-Myriophyllum Spicatum Aquatic Microcosm Using Oleic Acid-embedded Cellulose Acetate Membranes

Feng Xiaojian,Wang Haoxin,Xu Yanjun,Wu Chi,Pang Sen,Chen Yajie

Pyrethroids (PYRs) frequently occur in aquatic environments, but their distribution and accumulation in multi-compartment systems remain poorly understood. Permethrin (Per), fenpropathrin (Fen), and bifenthrin (Bif) were investigated in a 21-day water–sediment-zebrafish ( Danio rerio )- Myriophyllum spicatum microcosm. Per was added to water, whereas Per, Fen, and Bif were separately added to sediment. Concentrations in oleic acid-embedded cellulose acetate membranes (OECAMs) were converted to equivalent aqueous exposure concentrations using compound-specific OECAM-water partition coefficients. These values were used to derive apparent bioconcentration factors (BCFs) for zebrafish and accumulation factors for M. spicatum during the late exposure phase. At 504 h, sediment accounted for 58.46% of recovered Per in the water-spiked treatment, while zebrafish and M. spicatum accounted for 18.46% and 17.16%, respectively. In the sediment-spiked treatments, 99.43%-99.87% of recovered PYRs remained in sediment. After correction for pesticide removed by repeated sampling, recoverable parent mass decreased by 67.90% in the water-spiked treatment and by 27.64%-39.27% in the sediment-spiked treatments. OECAM-normalized apparent BCFs ranged from 389.31 to 970.11 L kg −1 wet weight in zebrafish, while accumulation factors ranged from 262.94 to 769.58 L kg −1 wet weight in M. spicatum . The OECAM-derived metric provided an exposure-related basis for interpreting organism accumulation under dynamic aqueous conditions, particularly when conventional water measurements became limited by low concentrations.

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