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Oleic Acid
AAPS PHARMSCITECH · 2024 ·Vol. 25 ·期 6 ·1-14 · IF 3.4

Effects and Action Mode of Oleic Acid and Azone on Release and Penetration Process of Levothyroxine Sodium Patches

Li Xing,Liang Kaili,Dong Yingying,Li Shen,Gao Zhengnan,Wang Qing

In recent years, there has been a significant increase in the prevalence of thyroid diseases, particularly hypothyroidism. In this study, we investigated the impact and mechanisms of Chemical permeation enhancement(CPE) on transdermal permeation of levothyroxine sodium (L-T4) patches.We found that the combination of oleic acid (OA) and Azone (NZ) yielded the best transdermal permeation effect for L-T4.Subsequently, we also investigated the relevant propermeability mechanism.The results demonstrate that the combined application of OA and NZ significantly enhances the transdermal permeation of L-T4 compared to individual applications,it is attributed to two mechanisms: firstly, OA improves drug release by increasing the flowability of the pressure-sensitive adhesive (PSA) matrix; secondly, both OA and NZ act on the stratum corneum, especially facilitating L-T4 permeation through the hair follicle pathway. No skin irritation or cytotoxicity is observed with these final patches, which exhibit a remarkable therapeutic effect on hypothyroidism. this study contributes to the development of transdermal formulations of L-T4. Graphical Abstract

CAS / MDL: 112-80-1
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FOOD CHEMISTRY · 2024 · IF 8.5

Modulating rice digestibility: Mechanisms of ultrasound, oleic acid and moist-heat treatments influence structural, physicochemical and digestive properties

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

The research compared the combined effect of ultrasound (160 W, 2 min), oleic acid (15%, 11 h), and moist-heat treatment (HMT, 25% moisture content, 110 °C, 2 h) with their individual treatment on rice grains. The results showed that ultrasound treatment created pores and cracks in the rice grains, facilitating an easier penetration for oleic acid to develop amylose-oleic acid complex during HMT. Compared to native raw rice (NR), both single and combined treatments significantly altered the morphology, reduced swelling power and solubility, enhanced hydrophilicity, thus changing the moisture distribution, thermal and pasting characteristics. Notably, the combined treatment of three techniques significantly increased the relative crystallinity, accompanied by the highest digestive resistance, and the content of resistant starch was increased from 20.53% in NR to 31.75%, much higher than the other treatments. These findings provide potential for the manufacturers to rationally and flexibly employ this low digestible rice in health food products.

CAS / MDL: 112-80-1
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Journal of Inorganic and Organometallic Polymers and Materials · 2024 · IF 3.9

Synthesis of Nanoscale ZSM-5 Zeolites for the Catalytic Cracking of Oleic Acid into Light Olefins and Aromatics

Liu Hao,Wang Yanlin,Yuan Hong,Luo Wenbo

Nanoscale ZSM-5 zeolites (NZSM-5) having different crystal sizes and Si/tetrapropylammonium hydroxide (TPAOH) molar ratios were synthesized using a hydrothermal method. These materials were characterized by X-ray diffraction, scanning electron microscopy, transmission electron microscopy, and N 2 adsorption–desorption. The results showed that each zeolite was highly crystalline regardless of the Si/TPAOH ratio and that the Brunauer–Emmett–Teller surface areas were in the range of 329−392 m 2 /g. The random aggregation of these nanoparticles resulted in the formation of numerous intergranular mesopores. These NZSM-5 zeolites were applied to the catalytic cracking of oleic acid to prepare light olefins and light aromatics using a laboratory-scale fixed bed reactor. The zeolite having a Si/TPAOH ratio of 10/5 showed the best catalytic activity and provided light olefins yield of 55% and selectivity of BTX in liquid phase products of 18%, respectively, at 500 °C. The small crystal size and abundant intergranular mesopores in this specimen resulted in shorter diffusion paths and an increase in the external specific surface area that both inhibited coke deposition and ensured accessible acid sites. Graphical Abstract

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JOURNAL OF POROUS MATERIALS · 2024 · IF 2.5

Oleic acid decarboxylation to produce C8-C17 alkanes catalyzed by Pt and Ni on a MOF-derived zirconia

Shi Xiang,Wang Ke,Wang Minxin,Yuan Hong

UiO-66 specimens having different acetic acid/ZrCl 4 molar ratios were prepared and pyrolyzed to ZrO 2 as supports for Pt and Ni, intended to catalyze the decarboxylation of oleic acid. Brunauer-Emmett-Teller surface area analyses, NH 3 temperature-programmed desorption and pyridine adsorption infrared spectroscopy showed that the material made using an acetic acid/ZrCl 4 molar ratio of 100 (ZrO 2 -100) had the largest specific surface area, acid amount and acid strength values. The yield of C 8 -C 17 alkanes obtained from Ni/ZrO 2 -100 exceeded that provided by Pt/ZrO 2 -100 because the latter possessed more acidic sites than the former, which excessively cracked long-chain hydrocarbons. The 1 wt% Ni/ZrO 2 -100 catalyst showed the best catalytic performance, with 96.4% conversion of oleic acid and an 80.6% yield of C 8 -C 17 alkanes after 4 h at 340 °C under a CO 2 atmosphere at a pressure of 18 bar. The conversion of oleic acid remained almost unchanged after 4 reuses of this catalyst whereas the yield of C 8 -C 17 alkanes decreased to 66.7%. This result is attributed to a loss of acidic sites and an increase in carbon build-up.

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CHEMICAL ENGINEERING JOURNAL · 2025 · IF 13.2

Manganese-doped oleic acid functionalized whitlockite/polycaprolactone nanocomposite scaffolds enhance bone regeneration through improved dispersibility and antioxidative capacity

Xiaofan Liu,Yang Liu,Peiyu Wang,Ye Tian,Yuping Zhao,Yuxuan Wang,Wenqian Zheng,Yi Wang,Yaru Shi,Yi Xie,Na Zhou,Fermín E. González,Hongchen Sun,Ding Zhou,Xiaowei Xu

Bone defects present significant clinical challenges due to the complexities of healing. While polycaprolactone (PCL) scaffolds offer promising mechanical support for bone tissue engineering, their limited bioactivity and dispersibility issues with bioactive fillers restrict their effectiveness. Here, we develop manganese-doped oleic acid-functionalized whitlockite (Mn-OAWH) nanoparticles designed to enhance both the mechanical and biological properties of PCL scaffolds. The nanoparticles were synthesized via a hydrothermal approach using oleic acid as both solvent and surface ligand, enabling superior dispersibility in dichloromethane and uniform integration with PCL. Characterization of the resulting 3D printed Mn-OAWH/PCL composite scaffolds confirmed enhanced compressive strength, supported by both mechanical testing and finite element analysis. In vitro studies demonstrated that the release of Mn 2+ , Mg 2+ , and Ca 2+ ions significantly promoted osteogenic proliferation, exhibited strong antioxidative properties, and accelerated osteogenic differentiation. Furthermore, in vivo implantation in a rat critical-sized cranial defect model revealed significantly improved bone formation compared to undoped and PCL-only controls. These findings establish Mn-OAWH/PCL composite scaffolds as a promising platform for bone tissue engineering, offering both enhanced mechanical support and biological functionality through improved nanoparticle dispersibility, strong antioxidative properties and osteogenic activity.

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JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY · 2011 ·Vol. 89 ·期 4 ·705-711 · IF 1.587

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi-SO3H-Functionalized Ionic Liquid as an Efficient Catalyst

Li Rui-Jun,Chen Li,Yan Zong-Cheng

Biodegradable trimethylolpropane triesters of oleic acid were synthesized by esterification of trimethylolpropane and oleic acid over a multi-SO 3 H-functionalized strong Brønsted acidic ionic liquid as the catalyst. The results showed that the esterification can proceed satisfactorily over the catalyst at an ambient pressure even without simultaneous removal of water. Under the optimal reaction conditions (temperature: 100 °C, reaction time: 3 h, reactant molar ratio: 3.6:1, and catalyst amount, high conversion rate of trimethylolpropane (99.0%) and selectivity of trimethylolpropane triester (92.1%) were obtained. The ionic liquid was reused six times after the removal of water and no obvious change in catalytic activity was detected. Operational simplicity, high yields along with good reusability makes the multi-SO 3 H-functionalized ionic liquid a promising catalyst for the esterification of trimethylolpropane with oleic acid.

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Molecular Catalysis · 2023 · IF 4.6

Facet-dependent Pd0-O2−-Ce3+ active site for selective hydrogenation of linoleate ester to cis oleic acid ester

Minghao Zha,Hao Yan,Ruiying Li,Yinghao Sun,Ruitong Wang,Yibin Liu,Xiaobo Chen,Xin Zhou,Xiang Feng,Chaohe Yang

Reducing the formation of trans fatty acid in vegetable oil hydrogenation process is of significance to ensure food safety. Herein, Pd 0 -O 2− -Ce 3+ active site was constructed by strong electronic interactions between Pd 0 and CeO 2 -Polyhedrons to promote the formation of cis fatty acid. Results reveal that the abundant oxygen vacancies of CeO 2 (111) facets promote the adsorption and activation of hydrogen, leading to excellent catalytic activity of Pd/CeO 2 -Polyhedrons. Moreover, electronic reconstructed Pd 0 -O 2− -Ce 3+ active site limits the σ-bond rotation of half-hydrogenated intermediates through enhancing π backdonation and weakening the σ-bond, contributing to the reduction of trans products. Under mild conditions (30 °C, 0.3 MPa H 2 , and 2 h), Pd/CeO 2 -Polyhedrons catalyst shows exceptional methyl oleate selectivity of 52.6% with 93.8% conversion for sunflower oil hydrogenation. The catalyst has been further extended to the selective hydrogenation to several other vegetable oils such as sunflower oil, peanut oil, soybean oil, among others, under mild conditions.

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BIOMASS & BIOENERGY · 2026 · IF 5.8

High-defect sulfonated carbon derived from beet molasses for effectively biodiesel production by esterification of methanol and oleic acid

Tianhong Mei,Wugan Wei,Huabo Li,Qing Fang,Yan Fang,Xiaoqian Ren,Jianliang Zhu,Jinhua Liang

A highly defective sulfonated carbon catalyst has been successfully synthesized from beet molasses via carbonization and sulfonation. This catalyst exhibited a high acid density of 2.47 mmol/g. Prepared under optimized conditions (carbonization at 550 °C for 4 h and sulfonation at 110 °C for 8 h), the catalyst exhibited a defective carbon structure with an ID/IG ratio of 1.36 and a high specific surface area of 221.7 m 2 /g. Moreover, the optimized catalyst was used for the esterification of oleic acid with methanol to produce biodiesel. The esterification process was further optimized through single factor and RSM box-behnken design (BBD), and the oleic acid esterification rate reached a maximum of 91.57 % under optimal conditions. Furthermore, the catalyst retained 87.2 % activity after 10 cycles, demonstrating excellent stability. Fuel properties of the produced biodiesel met ASTM D6751 and GB/T 25199-2017 standards. This work presents a sustainable strategy for valorizing industrial molasses waste into an efficient solid acid catalyst, contributing to green biodiesel synthesis and biomass resource utilization.

CAS / MDL: 77-09-8
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CATALYSIS LETTERS · 2026 ·Vol. 156 ·期 3 ·80 · IF 2.5

Seed-Assisted Hierarchical H-ZSM-5: Overcoming Diffusion Barriers for Efficient Recyclable Oleic Acid Isomerization to Commercial Isostearic Acid

Li Xincheng,Huang Pengpeng,Fan Mingming,Zhang Pingbo

Isostearic acid, a bio-based and environmentally friendly chemical, has attracted considerable attention because of its high value as an oleic acid derivative. The synthesis of isostearic acid via oleic acid isomerization over commercial H-ZSM-5 zeolites is limited by low yield and acid value, mainly due to diffusion constraints. To address this issue, a hierarchical-pore H-ZSM-5 zeolite (Meso-5) was synthesized using Silicalite-1(S-1) as a seed crystal to enhance diffusion and catalytic performance. The catalyst was comprehensively characterized by XRD, SEM, BET, TGA, FT-IR, and Py-FTIR. Meso-5 efficiently catalyzed the isomerization of oleic acid, attributed to its abundant Brønsted and Lewis acid sites whose synergistic interaction significantly promoted the formation of branched-chain products. The catalyst delivered a selectivity of 87.3% with a 71.1% yield in the first run, and even after five reuse cycles it maintained 82.1% selectivity with a 55.6% yield. Evidently, the hierarchical pore structure of the catalyst significantly facilitated the diffusion of oleic acid molecules and their isomerized intermediates, thereby enhancing the overall catalytic activity. The resulting isostearic acid was purified via a simple recrystallization procedure to a purity of 83.4% and an acid value of 186.7 mg KOH/g, both meeting the standards of commercial isostearic acid. These findings provide a robust basis for further catalyst optimization and scale-up toward industrial isostearic acid production. Graphical A tandem catalytic route combining ZSM-5-driven isomerization with Ni/C-catalyzed hydrogenation enabled the efficient conversion of oleic acid to isostearic acid. The hierarchical H-ZSM-5 structure enhanced branched-chain formation, ensuring high selectivity and yield toward the desired product

CAS / MDL: 112-80-1
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MICROPOROUS AND MESOPOROUS MATERIALS · 2026 · IF 4.5

Selective regulation of products for oleic acid pyrolysis by adjusting acid strength and the acidic environment of the catalysts

Hanxu Guo,Yao Dai,Hong Yuan,Huakun Zhao

In recent years, the catalytic pyrolysis of biomass to produce benzene, toluene and xylene (BTX) by ZSM-5 zeolite with hierarchical pore structure has received significant research interest. The dendritic ZSM-5 (DZ) zeolite with high specific surface area and hierarchical pore structure was synthesized in present work. The acid strength and acid type of the catalyst were systematically tailored by precisely adjusting the Si/Al molar ratio and incorporating zinc and iron modifications. The crystal structure, morphology, pore characteristics, and acidic properties of the catalyst were systematically characterized by XRD, TEM, FTIR, 27 Al MAS NMR, NH 3 -TPD, and Py-IR. The results show that adjusting the acid strength and acid type effectively promoted the catalytic pyrolysis of oleic acid into BTX. The metal Zn modification could significantly reduce the Brønsted-to-Lewis (B/L) acidity ratio of DZ, which not only optimized the balance of acid site types but also enhanced its catalytic performance. The appropriate modification with Fe not only further optimized the acid site distribution but also enhanced the dispersion of Zn species, leading to the formation of additional ZnOH + activation centers and thereby promoting the aromatization of low-carbon olefins. The 2Fe5Zn/DZ 30-0.05 catalyst achieved a high BTX yield of 14.8% while maintaining stable catalytic performance for up to 40 h.

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FUEL PROCESSING TECHNOLOGY · 2022 · IF 8.129

Biomass-derived hydrophobic metal-organic frameworks solid acid for green efficient catalytic esterification of oleic acid at low temperatures

Yuncong Li,Kaixun Zhu,Yiyuan Jiang,Long Chen,Heng Zhang,Hu Li,Song Yang

Biodiesel , of great significance, is a promising kind of non-polluting renewable energy that can meet world energy needs. However, the by-product water of esterification reaction used for biodiesel production is not conducive to the positive reaction, and even destroys the activity and structure of the used catalyst. In this study, a renewable solid acid catalyst FDCA/SA-Hf with a degree of hydrophobicity was simply prepared by a solvent-free assembly manner using biomass-based materials. FDCA/SA-Hf was found to be efficient for producing biodiesel from the abundant free fatty acid and nonedible raw oils at a low temperature, and its reaction mechanism was also studied. FDCA/SA-Hf showed stable structural properties and excellent hydrophobic network (131.5°), wherein the chemical grafting of stearic acid improved its Lewis acidity and promoted the adsorption of free fatty acid and the desorption of water. Importantly, as promoted by FDCA/SA-Hf in esterification, a high biodiesel yield reached 98.6% (49 °C, 4.1 wt%, 19.5:1 and 9.5 h). After being easily reused, biodiesel yield still achieved 90% even in the presence of 6 wt% water or after six cycles, which was due to the high hydrophobicity and stability. FDCA/SA-Hf shows great potential in heterogeneous acid-mediated catalytic fields, especially for biodiesel production.

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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2023 · IF 5.2

Ultra-rapid transfer of oleic acid-coated hydroxyapatite nanocrystals into water via a sodium citrate-assisted ligand exchange strategy

Junjun Tan,Tao Pan,Ruojiao Su,Miaomiao Wang,Yuwei Jiang

Precise control of the size, morphology and surface hydrophilicity of HA nanocrystals is an important prerequisite for the realization of relevant applications, especially biologically relevant ones. Although sodium oleate-assisted hydrothermal methods have received considerable attention due to their impressive synthesis quality and extremely wide aspect ratio tunability. However, the synthesized nanocrystals are usually hydrophobic due to oleic acid encapsulation, which greatly limits their wide application in biomedical fields. In view of this, we have established a robust ligand exchange strategy with sodium citrate as the exchange ligand and a mixture of water and ethanol as the exchange environment. The ligand exchange reaction requires only 5 min of stirring at 25 °C. DLS and zeta potential results show that the ligand-exchanged HA nanocrystals are highly negatively charged in water and dispersed as individual particles in water. TG and IR results showed that the oleic acid ligands on the surface of the nanocrystals were completely replaced by citric acid ligands. TEM images showed no change in the size and morphology of the nanocrystals before and after ligand exchange. Moreover, the colloidal stability of the ligand-exchanged HA nanocrystals in water could be quickly recovered in a few seconds even after freeze-drying into powder. The success of ligand exchange is mainly attributed to the fact that sodium citrate complexes calcium ions more strongly than sodium oleate , as well as the addition of ethanol eliminates the oil-water interface providing the basis for the approach of sodium citrate molecules to HA nanocrystals. This strategy undoubtedly bridges the gap that oleic acid-coated HA nanocrystals can be quickly and efficiently transferred to water, allowing HA nanocrystals to be used in bio-related applications without any obstacles.

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