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This study explores the efficient conversion of castor oil to sebacic acid utilizing iron oxide (Fe2O3) loaded on activated carbons as catalysts. Through a combination of saponification, acidification, and catalytic cracking, sebacic acid was produced with a notable yield improvement. The process involved using liquid paraffin as a thinning agent, overcoming the limitations of traditional toxic agents. The catalysts were prepared via adsorption-precipitation-calcination methods, with ultrasonication pretreatment to enhance iron adsorption on activated carbons. The chemical composition, structure, and morphology properties were investigated by different characterizations; such as scanning electron microscopy (SEM), thermogravimetric analysis (TG/DTG). Systematic investigations into the adsorption capacity, catalytic activity, and operational parameters like temperature, reaction time, and catalyst recycling were conducted. The optimized method achieved a sebacic acid yield of 83.4%, significantly higher than traditional methods (60.2%), with improved safety and environmental impact. The study provides valuable insights into sustainable and efficient sebacic acid production which is crucial for industrial applications in processing of castor oil. [ABSTRACT FROM AUTHOR]

This study explores the use of sebacic acid, a catalyst not previously examined in the literature, for hydrogen production from NaBH4 through methanolysis and ethanolysis reactions. Solutions of sebacic acid with concentrations ranging from 0.1 M to 0.4 M were prepared and tested. At a concentration of 0.3 M, 90% of the hydrogen from a 0.33 M NaBH4 solution was released within 3 s, and full release was achieved in 4 s. Hydrogen production rates reached 4500 mL/min for ethanolysis and 4845 mL/min for methanolysis, with methanolysis reactions proving faster. The activation energies for methanolysis and ethanolysis were calculated as 7.17 kJ/mol and 52.3 kJ/mol, respectively. These results demonstrate that sebacic acid enables rapid and efficient hydrogen production, offering a new approach that significantly advances current hydrogen production methods. [ABSTRACT FROM AUTHOR]

Since monomers in backbone of poly(butylene succinate-co-adipate) (PBSA) are not entirely derived from bio-based sources, limiting its application in the face of increasingly stringent environmental policies. In this study, a novel full bio-based biodegradable random copolyester poly(butylene succinate-co-sebacicate-co-salicylicate) was successfully synthesized. Detailed investigations were conducted on the structural, mechanical, and degradation characteristics resulting from the introduction of salicylicate and sebacicate units. Introduction of salicylicate units effectively enhanced the mechanical performance. In comparison to PBSA, the tensile modulus of copolymer increased by 20.2% with 10% salicylic acid. Introduction of sebacicate units significantly altered the crystalline structure of copolymer and promote the degradation efficiency. Considering both mechanical strength and degradation efficiency, the copolyester with 2% salicylic acid and 20% sebacic acid was found to meet practical application requirements. Relative to PBSA, this copolymer demonstrated a 13.7% increase in tensile modulus and a remarkable 143.1% improvement in degradation efficiency. Importantly, this study focused on the effect of the bio-based rigid monomer salicylic acid and the soft monomer sebacic acid on the degradability of biodegradable polymers. The insights gained provide valuable guidance for tailoring the synthesis of degradable plastics to meet diverse degradation cycle requirements. [ABSTRACT FROM AUTHOR]

The popularity of royal jelly (RJ) as a functional food has attracted attention from various industries, especially nutraceuticals, due to the increasing demand from health enthusiasts. Sebacic acid, 10‐hydroxy decanoic acid, and trans‐10‐hydroxy‐2‐decanoic acid are the primary medium‐chain fatty acids (MCFAs) within RJ responsible for their health benefits. This review aims to consolidate information on these MCFAs' metabolic relationship and health functionalities in nutraceutical applications. We also investigated the natural characteristics mediated by these MCFAs and their metabolism in organisms. Finally, the production of these MCFAs using conventional (from castor oil) and alternative (from RJ) pathways was also discussed. This review can be a reference for using them as functional ingredients in nutraceutical industries. [ABSTRACT FROM AUTHOR]

[Display omitted] The development of gels capable to adapt and act at the interface of rough surfaces is a central topic in modern science for Cultural Heritage preservation. To overcome the limitations of solvents or polymer solutions, commonly used in the restoration practice, poly(vinyl alcohol) (PVA) "twin–chain" polymer networks (TC-PNs) have been recently proposed. The properties of this new class of gels, that are the most performing gels available for Cultural Heritage preservation, are mostly unexplored. This paper investigates how chemical modifications affect gels' structure and their rheological behavior, producing new gelled systems with enhanced and tunable properties for challenging applications, not restricted to Cultural Heritage preservation. In this study, the PVA-TC-PNs structural and functional properties were changed by functionalization with sebacic acid into a new class of TC-PNs. Functionalization affects the porosity and nanostructure of the network, changing its uptake/release of fluids and favoring the uptake of organic solvents with various polarity, a crucial feature to boost the versatility of TC-PNs in practical applications. The functionalized gels exhibited unprecedented performances during the cleaning of contemporary paintings from the Peggy Gugghenheim collection (Venice), whose restoration with traditional solvents and swabs would be difficult to avoid possible disfigurements to the painted layers. These results candidate the functionalized TC-PNs as a new, highly promising class of gels in art preservation. [ABSTRACT FROM AUTHOR]

This study explores the efficient conversion of castor oil to sebacic acid utilizing iron oxide (Fe2O3) loaded on activated carbons as catalysts. Through a combination of saponification, acidification, and catalytic cracking, sebacic acid was produced with a notable yield improvement. The process involved using liquid paraffin as a thinning agent, overcoming the limitations of traditional toxic agents. The catalysts were prepared via adsorption-precipitation-calcination methods, with ultrasonication pretreatment to enhance iron adsorption on activated carbons. The chemical composition, structure, and morphology properties were investigated by different characterizations; such as scanning electron microscopy (SEM), thermogravimetric analysis (TG/DTG). Systematic investigations into the adsorption capacity, catalytic activity, and operational parameters like temperature, reaction time, and catalyst recycling were conducted. The optimized method achieved a sebacic acid yield of 83.4%, significantly higher than traditional methods (60.2%), with improved safety and environmental impact. The study provides valuable insights into sustainable and efficient sebacic acid production which is crucial for industrial applications in processing of castor oil.

This study explores the use of sebacic acid, a catalyst not previously examined in the literature, for hydrogen production from NaBH4 through methanolysis and ethanolysis reactions. Solutions of sebacic acid with concentrations ranging from 0.1 M to 0.4 M were prepared and tested. At a concentration of 0.3 M, 90% of the hydrogen from a 0.33 M NaBH4 solution was released within 3 s, and full release was achieved in 4 s. Hydrogen production rates reached 4500 mL/min for ethanolysis and 4845 mL/min for methanolysis, with methanolysis reactions proving faster. The activation energies for methanolysis and ethanolysis were calculated as 7.17 kJ/mol and 52.3 kJ/mol, respectively. These results demonstrate that sebacic acid enables rapid and efficient hydrogen production, offering a new approach that significantly advances current hydrogen production methods.

Castor oil is a widely used biomass energy source. In this paper, the process conditions for the preparation of sebacic acid by cracking castor oil using the microwave method were investigated using environmentally friendly and recyclable liquid paraffin (petrolatum) as a solvent. The optimum conditions for the reaction were determined in the experiments as follows: the mass ratio of solvent: castor oil: sodium hydroxide was 4:1:2.5 and the concentration of sodium hydroxide solution was 50% (w/t). The average microwave power was 210 W, the temperature was about 280 °C, the cracking time was 25 min under nitrogen protection, and the yield of sebacic acid was measured to be 85%. The solvents can be recycled and the recovered solvent can be used again without affecting the yield of sebacic acid. The solvent recovery was more than 92%.

A series of epoxy vitrimers (EVs) with enhanced glass transition temperatures (Tgs) were synthesized by curing epoxy resin E51 with different ratios of phthalic anhydride and sebacic acid as curing agents, and 1,5,7-triazabicyclic [4.4.0] dece-5-ene as a transesterification catalyst, and their curing dynamics, rheological properties, mechanical properties, and thermal stability were comprehensively investigated. By adjusting the molar ratio of the anhydride to the carboxylic acid in the curing agent, the Tgs of the EVs increased from 79 to 143 °C with the increase in the anhydride content. In particular, the material EV-5.5 with a high usable Tg of 98 °C could undergo stress relaxation through the transesterification reaction when exposed to high temperatures (160 to 200 °C), and the correlation between the relaxation time and temperature follows the Arrhenius equation. Moreover, EV-5.5 exhibited elastomeric behavior, where brittle fractures occurred before yielding, which demonstrated a tensile strength of 52 MPa. EV-5.5 also exhibited good thermal stability with a decomposition temperature (Td5) of 322 °C. This study introduces new possibilities for practical applications of thermoset epoxy resins under special environmental conditions. [ABSTRACT FROM AUTHOR]

An efficient synthesis of optically pure macrocyclic mono- and binuclear polylactones has been proposed. The synthesis is based on the condensation of natural triol, castor oil, with sebacoyl dichloride in 1 : 1 or 1 : 2 ratios in boiling carbon tetrachloride in the presence of triethylamine and N,N-dimethylaminopyridine as a catalyst. [ABSTRACT FROM AUTHOR]

The consistency and tribological measurements of bio-grease, which consists of calcium 12-hydroxy stearic acid as a thickener with a complexing agent like sebacic acid dispersed in rice bran oil (RBO) at different formulation parameters, were examined. The calcium complex thickener was obtained by mixing calcium hydroxide to 12-hydroxy stearic acid (12 HSA) at a ratio of 1:1, and the concentration of sebacic acid added was varied from 1/3 to 1/6 of 12 HSA concentration. The weight percentage of thickener, saponification time, and holding time to dissolve sebacic acid spanned the ranges 5–11 wt.%, 1–2.5 h, and 10–25 min, respectively. The maximum temperature for formulating calcium complex grease was maintained at 160 °C. The present work experimentally investigated the effect of these grease formulation parameters on the formulated greases' consistency and tribological measurements as per ASTM standards. The experimental results obtained from the developed calcium complex greases (sixteen samples) have indicated that these formulation parameters' variation plays a vital role in the evaluated properties. [ABSTRACT FROM AUTHOR]

Vegetable oil-based lubricants are environment-friendly options as against conventional lubricants. This paper discusses the synthesis as well as characterisation of esters from ricinoleic acid and sebacic acid whose main source is castor oil. Physicochemical properties, tribological study as well as oxidation study have been carried out for the esters. With the increase in ester chain length, extreme pressure properties, viscosity index and pour point has improved, whereas oxidation stability had a detrimental effect. The coefficient of friction for commercial base stocks was better than any of the studied esters.

Castor oil is one important raw material that could serve as a renewable feedstock for industries in the age of exhausting fossil fuels. The chemical composition of oil and the structure of hydroxyl fatty acid are responsible for its unique physicochemical properties. The oil has diverse applications from pharmaceuticals to polyamides, from the manufacturing of ski boots to durable frames, and from lubricants to laxatives. The present review gives an insight into the physicochemical properties of castor oil and its application. The oil is used for the production of a great variety of its derivatives. Out of many derivatives of castor oil, four are produced and utilized at a larger scale. The names of the four derivates are ricinoleic acid, sebacic acid, undecylenic acid, and γ‐decalactone. The review will aim toward an insight into the evolved techniques for the manufacturing of these derivatives of castor oil, the biotechnological route of production, and metabolic engineering approaches. Though the industrial significance of castor oil and its derivatives had been known for ages, methods for their production are continuously changing. [ABSTRACT FROM AUTHOR]

This work describes the development and characterization of mechanical flexible epoxy resins based on epoxidized vegetable oils (EVO) and sebacic acid. Different oil types (linseed oil, hempseed oil, and soybean oil) with varying epoxy equivalent weight (EEW) were used. Formulation and processing parameters were systematically optimized by differential scanning calorimetry and Fourier‐transform infrared spectroscopy. The effect of the EVO type and EEW on thermo‐mechanical and mechanical properties were investigated by dynamic mechanical analysis and tensile tests at different temperatures. The EVO type had a strong effect on the thermo‐mechanical and mechanical properties of the resin. However, for the investigated commercial epoxidized linseed oils, the EEW had no effect on these properties. With epoxidized linseed oil the highest Tg and the best mechanical properties (highest tensile strength and toughness) were achieved. [ABSTRACT FROM AUTHOR]

A series of epoxy vitrimers (EVs) with enhanced glass transition temperatures (Tgs) were synthesized by curing epoxy resin E51 with different ratios of phthalic anhydride and sebacic acid as curing agents, and 1,5,7-triazabicyclic [4.4.0] dece-5-ene as a transesterification catalyst, and their curing dynamics, rheological properties, mechanical properties, and thermal stability were comprehensively investigated. By adjusting the molar ratio of the anhydride to the carboxylic acid in the curing agent, the Tgs of the EVs increased from 79 to 143 °C with the increase in the anhydride content. In particular, the material EV-5.5 with a high usable Tg of 98 °C could undergo stress relaxation through the transesterification reaction when exposed to high temperatures (160 to 200 °C), and the correlation between the relaxation time and temperature follows the Arrhenius equation. Moreover, EV-5.5 exhibited elastomeric behavior, where brittle fractures occurred before yielding, which demonstrated a tensile strength of 52 MPa. EV-5.5 also exhibited good thermal stability with a decomposition temperature (Td5) of 322 °C. This study introduces new possibilities for practical applications of thermoset epoxy resins under special environmental conditions.

Polyglycerol sebacate (PGS) is elastomeric biodegradable polymer with potential biomedical and green packaging applications. This study focuses on the synthesis of vitrimer-like PGS utilizing various catalysts, including Zinc acetate, Zinc oxide and Amberlyst-15. The investigation of vitrimer-like of PGS polymer by polycondensation of glycerol and sebacic acid with various molar ratio of 1:1, 1:1.25 and 1:1.5 will be studied. The synthetic time and temperature were controlled at 72 h, 120 °C, respectively. The prepolymer of PGS had a weight-average molecular weight (Mw.) of 1743. The result of functional group was confirmed by Fourier transforms Infrared spectroscopy (FTIR). The intense CO stretch at 1737 cm−1 confirms the formation of ester bonds. The intense OH stretch at 3454 cm−1 indicated hydroxyl groups from hydrogen bonded. When the quantity of catalyst is increased, the results of hardness are rising but swelling (%) becomes lower. The results showed a polymer network has higher cross-link when the catalyst increases. In addition, the proton nuclear magnetic resonance spectroscopy (1H NMR) analysis found that PGS using catalyst does not have peaks of glycerol.

Valorizing the fatty content of agricultural waste in material synthesis is an interesting topic. This work focused on utilizing oleic acid from the solid waste of olive mills in Saudi Arabia to synthesize biodegradable polyanhydrides based on sebacic acid which terminated with different concentrations of fatty acid (10, 30, 50, and 70 wt%), then characterize the final polymer samples and study the effects of termination on polyanhydrides properties, such as molecular weight and degradation profile. The fatty content of the solid waste was extracted, purified, and analyzed prior to and after separating the saturated and unsaturated fractions by urea crystallization, then the microwave-assisted melt polycondensation technique was used in the synthesis of the final polymers. Molecular weights were determined by gel permeation chromatography (GPC), and the degradation profile of the prepared samples was examined by determining the weight loss percentage of the polymer mass and FT-IR scanning for the anhydride bond before and after sample degradation. Results showed a linear degradation profile for most samples with no significant change in the molecular weights due to termination. [ABSTRACT FROM AUTHOR]

Sebacic acid (1,10-decanedioic acid) is an important chemical intermediate. Traditional chemical oxidation methods for sebacic acid production do not conform with "green" manufacturing. With the rapid development of enzymatic technologies, a biocatalytic cascade method based on the Baeyer–Villiger monooxygenase was developed. The most attractive point of the method is the oleic acid that can be utilized as raw material, which is abundant in nature. However, this bio-catalysis process needs co-factor electron carriers, and the high cost of the co-factor limits its progress. In this piece of work, a co-factor in situ regeneration system between ADH from Micrococcus luteus WIUJH20 (MlADH) and BVMO is proposed. Since the co-factors of both enzymes are different, switching the co-factor preference of native MlADH from NAD+ to NADP+ is necessary. Switching research was carried out based on in silico simulation, and the sites of Tyr36, Asp 37, Ala38, and Val39 were selected for mutation investigation. The experimental results demonstrated that mutants of MlADH_D37G and MlADH_D37G/A38T/V39K would utilize NADP+ efficiently, and the mutant of MlADH_D37G/A38T/V39K demonstrated the highest sebacic acid yield with the combination of BVMO. The results indicated that the in situ co-factor generation system is successfully developed, which would improve the efficiency of the biocatalytic cascade for sebacic acid production and is helpful for simplifying product isolation, thus, reducing the cost of the enzymatic transformations process. [ABSTRACT FROM AUTHOR]

Unsaturated Polyester Resin (UPR) is widely synthesized using non-renewable resources. However, the use of bio-based material is a need in today's world to ensure sustainable development. The presented investigation defines the use of bio-based itaconic acid (IA) as a replacement of conventional maleic anhydride (MAn) in UPR. The reactions of IA and MAn at varying ratios in the presence of sebacic acid (SA) and neopentyl glycol (NPG) were carried out. The objective was to investigate the effects of such replacement to bring more insight into structure–property relations. The synthesized resins were characterized by Fourier Transforms Infrared Spectroscopy (FTIR), Rheology, Gel Permeation Chromatography (GPC),Thermo-mechanical and other physical properties including viscosity and density. The addition of IA as a complete replacement to MAn increased the peak exotherm to 500C as opposed to 380C for polyester based on MAn alone. This led to quicker gelation and curing. Molecular weight Mn and Mw were found to be reduced to around 66% and 47% respectively leading to reduced viscosity. [ABSTRACT FROM AUTHOR]

BACKGROUND: As a bio‐derived platform molecule, levulinic acid can be converted to liquid fuels with similar components as aviation kerosene after undergoing aldol self‐condensation and successive hydrodeoxygenation reactions. In view of its complicated composition, sebacic acid was selected as a model compound for the investigating the hydrodeoxygenation performance of the product of levulinic acid self‐condensation in this work. RESULTS: Firstly, a series of supported metal catalysts were screened and characterized by temperature‐programmed desorption of NH3 and CO2, X‐ray diffraction, transmission electron microscopy, X‐ray photoelectron spectroscopy and CO pulse chemisorption. The results indicated that Ru/TiO2 showed the highest selectivity to total long‐chain alkanes at the complete conversion of sebacic acid. Then, the influence of preparation conditions on the catalytic performance of Ru/TiO2 and the effect of reaction conditions on the hydrodeoxygenation of sebacic acid were studied. On this basis, possible hydrodeoxygenation reaction routes were discussed. CONCLUSION: The excellent catalytic performance of Ru/TiO2 is attributed to a moderate degree of Ru reduction and dispersion, along with its unique acid–base characteristics. © 2022 Society of Chemical Industry (SCI). [ABSTRACT FROM AUTHOR]

Jules Bouis (1822-1886) was a French pharmacist that made a detailed study of castor oil. With the help of heat and distillation he separated and prepared a variety of compounds, such as œnantol, ricinolamide, ricinelaidic, caprylic, phosphocaprylic, and sebacic acids, ricinelaidine, caprylic alcohol, caprylene, capryl halides, sulfocaprylates, and capril amine. He also provided a detailed description of the physical and chemical properties of these compounds. Bouis analyzed the phenomena of solidification and fusion, particularly of fatty materials, and proposed a new method for their best determination based on covering the bulb of the thermometer with a thin layer of the material being tested. He explained the changes in the values of these parameters, when repeating the fusion-solidification cycle, as caused by a change in the structure of the solid phase. He gave a detailed tabulation of the variation of these parameters with the composition of a fatty mixture. Bouis studied the action of chlorine on mercury(I) cyanide in the dark and under the influence of sunlight and discovered a new derivative of formula C8N4Cl8,C4Cl6, methylene chloromesitate, and the existence of several cyanogene chlorides. Bouis studied the action of hydrogen on wrought iron and steel and found that it always generated ammonia from the outer layer of the metal and that steel contained much less nitrogen than wrought iron. This treatment transformed wrought iron into a very crystalline and fragile material that did not keep magnetism. [ABSTRACT FROM AUTHOR]

Royal jelly (RJ) intake has been reported to be effective for reducing serum lipids; however, the mechanism is not fully understood. Angiopoietin-like protein 8 (ANGPTL8), a secreted protein, plays a key role in lipid metabolism. In this study, we investigated the effects of specific fatty acids included in RJ (RJ fatty acids), such as 10-hydroxy-2-decenoic acid, 10-hydroxydecanoic acid, and sebacic acid (SA), on expression of ANGPTL8 in human hepatoma HepG2 cells. SA markedly reduced the expression of ANGPTL8. Reporter assay revealed that SA suppressed ANGPTL8 promoter activity. In addition, we identified a functional binding site of hepatocyte nuclear factor-4γ(HNF4α), a liver-enriched transcription factor, in the ANGPTL8 promoter. SA reduced the levels of HNF4γprotein and the binding of HNF4γto the ANGPTL8 promoter. Moreover, siRNA knockdown of HNF4γsuppressed the expression of ANGTPL8 mRNA. Taken together, we conclude that SA downregulates ANGPTL8 expression via the decrease in HNF4γprotein. [ABSTRACT FROM AUTHOR]

This work describes the synthesis of sebacic acid capped silver nanoparticles (SA-AgNPs) by the wet chemical method for the detection of l-Histidine in blood serum and urine samples. The synthesized SA-AgNPs were characterized by several techniques. The obtained particles were spherical in shape and the average diameter was calculated by HR-TEM images to be 11 nm. Moreover, the synthesized SA-AgNPs were stable for more than 3 months in solution. The synthesized SA-AgNPs showed the surface plasmon resonance (SPR) band at 420 nm. Interestingly, after the addition of 18.1 μM of l-Histidine into the SA-AgNPs solution, the SPR band absorbance decreased and the colour of the solution changed from brown to colourless. Based on the changes in the SPR band, we calculated the lowest detection limit to be 122 nM. The observed colour shift and spectral changes were due to the aggregation of SA-AgNPs induced by l-Histidine via hydrogen bonding interaction. Additionally, a possible mechanism is discussed. Furthermore, a 268-fold excess of common interferences did not interfere with the detection of 18.1 μM of l-Histidine. We successfully applied the SA-AgNPs probe for the detection of l-Histidine in blood serum and urine samples. Further, we validated our system with the HPLC technique. Importantly, we prepared a portable smartphone aided paper-based kit for on-site monitoring of l-Histidine. We strongly hope that this facile synthesis of SA-AgNPs and the portable paper-based kit will represent a step forward in the field of biosensing and materials science.

A simple and alternate organic synthetic route for sebacic acid, a high value ten‐carbon aliphatic dicarboxylic acid from castor oil is described in this study. Castor oil methyl esters are purified to obtain methyl ester of ricinoleic acid that is used as the starting material for the preparation of sebacic acid. The hydroxyl group of methyl ricinoleate is oxidized to corresponding 12‐oxo derivative followed by isomerization of the cis 9, 10 olefinic bond to trans 10, 11 isomer. The isomerized compound is subjected to dihydroxylation followed by oxidative cleavage and subsequent methylation to obtain dimethyl decanedioate. The dimethyl decanedioate is finally hydrolyzed to obtain sebacic acid. The intermediate compounds and final product are purified and characterized by chromatographic and spectral analysis. The final compound is analyzed by 1H and 13C‐NMR as well as high resolution mass spectrometry and compared with standard compound for the confirmation of the structure. Practical Applications: The design and preparation of sebacic acid by the novel alternate route is described. Castor oil, a renewable source, is utilized as the raw material for the preparation of sebacic acid. Isomerization of the 9, 10 cis bond to 10, 11 trans bond is the key step in the synthesis of sebacic acid. The chemical transformation of castor oil to sebacic acid by newer route is investigated. [ABSTRACT FROM AUTHOR]

Valorizing the fatty content of agricultural waste in material synthesis is an interesting topic. This work focused on utilizing oleic acid from the solid waste of olive mills in Saudi Arabia to synthesize biodegradable polyanhydrides based on sebacic acid which terminated with different concentrations of fatty acid (10, 30, 50, and 70 wt%), then characterize the final polymer samples and study the effects of termination on polyanhydrides properties, such as molecular weight and degradation profile. The fatty content of the solid waste was extracted, purified, and analyzed prior to and after separating the saturated and unsaturated fractions by urea crystallization, then the microwave-assisted melt polycondensation technique was used in the synthesis of the final polymers. Molecular weights were determined by gel permeation chromatography (GPC), and the degradation profile of the prepared samples was examined by determining the weight loss percentage of the polymer mass and FT-IR scanning for the anhydride bond before and after sample degradation. Results showed a linear degradation profile for most samples with no significant change in the molecular weights due to termination.

Sebacic acid (1,10-decanedioic acid) is an important chemical intermediate. Traditional chemical oxidation methods for sebacic acid production do not conform with “green” manufacturing. With the rapid development of enzymatic technologies, a biocatalytic cascade method based on the Baeyer–Villiger monooxygenase was developed. The most attractive point of the method is the oleic acid that can be utilized as raw material, which is abundant in nature. However, this bio-catalysis process needs co-factor electron carriers, and the high cost of the co-factor limits its progress. In this piece of work, a co-factor in situ regeneration system between ADH from Micrococcus luteus WIUJH20 (MlADH) and BVMO is proposed. Since the co-factors of both enzymes are different, switching the co-factor preference of native MlADH from NAD+ to NADP+ is necessary. Switching research was carried out based on in silico simulation, and the sites of Tyr36, Asp 37, Ala38, and Val39 were selected for mutation investigation. The experimental results demonstrated that mutants of MlADH_D37G and MlADH_D37G/A38T/V39K would utilize NADP+ efficiently, and the mutant of MlADH_D37G/A38T/V39K demonstrated the highest sebacic acid yield with the combination of BVMO. The results indicated that the in situ co-factor generation system is successfully developed, which would improve the efficiency of the biocatalytic cascade for sebacic acid production and is helpful for simplifying product isolation, thus, reducing the cost of the enzymatic transformations process.

Existing research has shown that the inclusion of polyethylene terephthalate (PET)-based additives can help in improving the performance of crumb rubber-modified bitumen (CRMB). However, its field applicability is limited as a result of inadequate storage stability and phase separation issues. This study was concerned with the further improvement in the stability of such binders by the incorporation of a dicarboxylic acid group into the blend, achieved with the addition of sebacic acid. The CRMB binders were prepared by the additives synthesised from waste PET and sebacic acid at different proportions, and tested through various conventional binder tests, storage stability test, superpave performance grading, Marshall Stability tests and Hamburg wheel tracking tests. The results indicated that the combination of sebacic acid and PET additives considerably improved the storage stability of CRMB, to within the acceptable limits for field applicability. It was further proposed that the chemical interaction of these additives with bitumen will help in increasing the phase integrity of CR in the bitumen matrix. From the various rheological tests conducted, it was also seen that the modified binders provided comparative performance at high temperatures when compared to CRMB, and improved performance at intermediate and low temperatures. [ABSTRACT FROM AUTHOR]

Royal jellies (RJs) possess moisturizing, emulsifying, and stabilizing properties, and several pharmacological activities have also been found to be present, which make them an ideal component for cosmetic and skin care products. However, despite the abundant efficacies, there is a lack of studies that explore the chemical composition of RJ using metabolome analysis. Furthermore, an evaluation of the chemical composition of Indonesian RJs collected from different regions has yet to be carried out. Therefore, the main objective of this study was to identify any differences in the chemical composition of such RJs. Chemical profiling was also carried out to enable more targeted utilization based on the actual compositions. Chemical profiling is also important given the rich Indonesian biodiversity and the high dependence of the RJ compositions on the botanical source. In this research, ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry was used as part of an untargeted metabolomics approach. From the chemical profiling, >30 compounds were identified across four RJ samples. The major constituents of the samples were found to be oligosaccharides, fatty acids, and adenosine monophosphate derivatives. Meanwhile, sucrose and planteose were found to be highest in the samples from Banjarnegara and Kediri, whereas dimethyloctanoic acid was found to be unique to the sample from Banjarnegara. It was also discovered that the RJs from Demak and Tuban contained more organic fatty acids and oligosaccharides than the other samples. Although the sample from Demak demonstrated good potential for use in the cosmetic, skin care, and bio-supplement industries, the higher abundance of fatty acids and oligosaccharides in the sample from Tuban indicated that it is perhaps the most suitable RJ for use in this field.

Macrophages produce many inflammatory mediators, such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6), in innate immune responses. However, excess production of these mediators by activated macrophages triggers deleterious effects, leading to disorders associated with inflammation. Royal jelly (RJ), a milky-white substance secreted by worker bees, contains unique fatty acids, including 10-hydroxy-2-decenoic acid (10H2DA) and sebacic acid (SA). 10H2DA has been reported to have various biological functions, such as anti-inflammation. However, the anti-inflammatory effect of SA is not fully understood. In this study, we investigated the effects of SA on lipopolysaccharide (LPS)-induced cytokine expression using differentiated human THP-1 macrophage-like cells. SA dose-dependently decreased LPS-induced mRNA expression of IL-6, but not TNF-α and IL-1β. SA suppressed the phosphorylation of signal transducers and activators of transcription 1 (STAT1) and STAT3, but hardly affected the activation of JNK, p38, or NF-κB. In addition, SA decreased LPS-induced interferon-β (IFN-β) expression, and the addition of IFN-β restored the inhibition by SA of LPS-induced STAT activation and IL-6 expression. Furthermore, SA suppressed LPS-induced nuclear translocation of interferon regulatory factor 3 (IRF3), a transcription factor responsible for IFN-β expression. Taken together, we conclude that SA selectively decreases LPS-induced expression of IL-6 mRNA through inhibition of the IRF3/IFN-β/STAT axis., Competing Interests: HH received a research grant from API Co., Ltd. However, the company was not involved in the study design, collection, analysis and interpretation of the data, or preparation of the manuscript. All other authors declare no conflict of interest., (Copyright © 2024 JCBN.)

Abstract Biotransformation of fatty acid methyl esters to dicarboxylic acids has attracted much attention in recent years; however, reports of sebacic acid production using such biotransformation remain few. The toxicity of decanoic acid is the main challenge for this process. Decane induction has been reported to be essential to activate the enzymes involved in the α,ω-oxidation pathway before initiating the biotransformation of methyl decanoate to sebacic acid. However, we observed the accumulation of intermediates (decanoic acid and 10-hydroxydecanoic acid) during the induction period. In this study, we examined the effects of these intermediates on the biotransformation process. The presence of decanoic acid, even at a low concentration (0.2 g/L), inhibited the transformation of 10-hydroxydecanoic acid to sebacic acid. Moreover, about 24–32% reduction in the decanoic acid oxidation was observed in the presence of 0.5–1.5 g/L 10-hydroxydecanoic acid. To eliminate these inhibitory effects, we applied substrate-limiting conditions during the decane induction process, which eliminated the accumulation of decanoic acid. Although the productivity of sebacic acid (34.5 ± 1.10 g/L) was improved, by 28% over that achieved using the previously methods, after 54 h, the accumulation of 10-hydroxydecanoic acid was still detected. The accumulation of 10-hydroxydecanoic acid even under the decane limiting conditions could be an evidence that oxidation of 10-hydroxydecanoic acid could be the rate-limiting step in this process. The improvement of this reaction should be an important objective for further development of the production of sebacic acid using biotransformation.

Castor oil and its three derivatives including methyl ricinoleate, sodium ricinoleate and ricinoleic acid were used as the raw material for alkali fusion to prepare sebacic acid. The reaction parameters including catalyst, ratio of oleochemicals/NaOH, reaction time and reaction temperature were optimized. It was found that Pb3O4 (1%) showed the best catalytic performance, and 553 K was considered as the most suitable reaction temperature. The oleochemicals/NaOH ratios of 15:14, 15:14, 15:12 and 15:14 were determined as the optimal ratio for alkali fusion of castor oil, methyl ricinoleate, sodium ricinoleate and ricinoleic acid, respectively. In addition, the optimal reaction time of alkali fusion of castor oil was 5 hours, and that of its derivatives was 3 hours. The maximum yield in sebacic acid of 68.8%, 77.7%, 80.1%, 78.6% can be obtained by using castor oil, methyl ricinoleate, sodium ricinoleate and ricinoleic acid as the raw material, respectively. High purity of sebacic acid was confirmed by GC and melting point analysis. ICP‐OES results illustrated that the content of Pb in sebcic acid was less than 1 mg kg−1. Separating glycerol from castor oil was beneficial for alkali fusion, by which, the yield of sebacic acid was increased of approximately 10%, and the reaction time was reduced from 5 to 3 hours. This study provided guiding significance for the future industrial production of sebacic acid. [ABSTRACT FROM AUTHOR]

The electric discharge bases of the technological advantages of diamond spark grinding make it possible to consider this processing method among the environmentally promising in nature. A decrease in the thermo-mechanical tension of mass micro-cutting in the zone of diamond spark grinding, which is ensured by the development of its working relief, supported by the action of electric discharges on the bond of the wheel, also makes it possible to consider approaches to organizing this process using the minimum lubrication methodology. The paper presents and summarizes the experimental results of using a number of solid lubricants, gives practical recommendations and defines the tasks of further research. Work in this direction is focused on reducing the use of water in servicing industrial needs, which is an urgent global environmental challenge to the development of civilization and meets the modern technocratic strategies of the European Union (Industry 4.0), Japan (Society 5.0), China (Made in China 2025) and other leading world economies. [ABSTRACT FROM AUTHOR]

The potential of sebacic acid as a corrosion inhibitor for hot‐dip galvanized steel in 0.1 M NaCl solution has been investigated. Different concentrations of the organic acid have been tested in order to understand the inhibition mechanism of the compound. The electrochemical test revealed a competitive mechanism between the dissolution of the metal in the acidified solution and the inhibition provided by the dicarboxylic species. The formation of a whitish layer consisting of zinc carboxylates and corrosion products was proved by means of scanning electron microscopy (SEM) investigation combined with Fourier transform infrared (FT‐IR) analysis. A bidentate bridging coordination between the Zn(II) and the carboxylic species is suggested. [ABSTRACT FROM AUTHOR]

In situ forming implants (ISFIs) appear to be a convenient drug delivery system, alternative to conventional preformed implants and microparticles for parenteral drug delivery applications. It has been shown that they offer several advantages including easy and minimally invasive application, potential for local/site‐specific drug delivery that allows reduction of side effects associated with systemic administration of drug. A few ISFI formulations based on poly(α‐hydroxy acids), solidifying by solid phase separation, are currently commercially available. In this work, polyesters based on sebacic acid, isosorbide, and optionally 1,2‐propanediol were synthesized and characterized. Poly(isosorbide sebacate‐co‐1,2‐propylene sebacate) (PISEBPG) was chosen as an essential constituent of new ISFI formulations dedicated to controlled release of doxycycline hyclate (DOXY). Basic characteristics of new ISFI formulations were investigated. In particular, the influence of addition of a relatively hydrophobic cosolvent (triacetin, TA) to a more hydrophilic 1‐methyl‐2‐pyrrolidone (NMP) as well as the presence of calcium carbonate (CAC) on the morphology of resulted depots and DOXY release profile was evaluated. Scanning electron microscopy (SEM) analysis revealed that the presence of TA resulted in more porous morphology of the depots. DOXY has been releasing continuously from depots in vitro within 12 weeks depending on the composition. The release profile of the PISEBPG‐based formulation containing CAC indicates that it could be useful where short‐term (up to 14 d), rapid release of the antibiotic is required, while formulation without CAC, where after 21 days about 50% of the drug loaded may still be available for release, may be better for the long‐term delivery of DOXY. [ABSTRACT FROM AUTHOR]

Abstract A new epoxy-based polymer sensor 1 incorporating 1-naphthylamine and sebacic acid moieties was synthesised. The sensor shows ON-OFF type fluorescence selectivity for Fe3+ over other coexistent metal ions such as Cu2+, Zn2+, Co2+, Ni2+, Cd2+, Hg2+, Mg2+, Sr2+, Pb2+ and Ca2+ ions. Graphical abstract Image 1035 Highlights • New epoxy-based polymer sensor incorporating 1-naphthylamine and sebacic acid moieties is synthesised. • Polymer is characterized by UV–vis, FTIR and NMR spectroscopies. • Polymer probe displays turn-OFF fluorescence sensitivity and selectivity for Fe3+ ion detection. [ABSTRACT FROM AUTHOR]

A phosphorus-containing epoxy resin has been derived from a renewable resource, sebacic acid (SA), and formulated for flame-retardant applications. The synthesized epoxy resin was characterized by physicochemical and spectral analysis including Fourier-transform infrared (FTIR), 1H and 31P nuclear magnetic resonance spectroscopies. Curing of the epoxy resin mixture was carried out with polyamide hardener at 1:1 stoichiometry on equivalent weight basis. The developed coatings were characterized in terms of their mechanical, solvent, gel content, water absorption, chemical, thermal, and flame-retardant properties, while the glass-transition temperature and thermal stability of the coatings were analyzed by differential scanning calorimetry and thermogravimetric analysis, respectively. The results revealed that the coatings with added SA-based epoxy resin showed good mechanical, chemical, and solvent-resistance properties. The thermal profile of the coatings manifested that the char yield increased with the concentration of the SA-based epoxy resin. Limiting oxygen index (LOI) and UL-94 tests were performed to understand the flame-retardancy behavior of the synthesized coatings, revealing an enhancement as the concentration of phosphorus-containing epoxy resin was increased. [ABSTRACT FROM AUTHOR]

Currently, nanoparticles (NPs) made of amphiphilic block copolymer are still an essential part of drug delivery system. Here, we report a novel amphiphilic block copolymer and paclitaxel (PTX)-loaded copolymer NPs for the controlled delivery of PTX. The block copolymer was synthesized via melt polycondensation method of methoxy poly(ethylene glycol) (mPEG), sebacic acid (SA) and ricinoleic acid (RA). A series of characterization approaches such as Fourier Transform Infrared Spectroscopy (FTIR), 1Hydrogen-Nuclear Magnetic Resonance (1H-NMR), Differential Scanning Calorimetry (DSC), X-Ray Diffraction (XRD) and Gel Permeation Chromatography (GPC) applied have shown that the amphiphilic block copolymer was prepared as designed. NPs prepared by nanoprecipitation method consist of mPEG segments as the hydrophilic shell and RA-SA segments as the hydrophobic core, hydrophobic PTX was encapsulated as model drug. Subsequently, Transmission Electron Microscopy (TEM) analysis indicated that the spherical NPs have effective mean diameters ranging from 100 to 400 nm. Dynamic Light Scattering (DLS) analysis also revealed the controllable NPs diameter by modulating the mass ratio of RA to SA and drug loading amount (DLA). Besides, biphasic profile with zero order drug release was observed in general in vitro release behaviors of PTX from NPs. Further investigation confirmed that the release behaviors depend on the crystallinity of hydrophobic RA-SA segments. Results above suggest that NPs with amphiphlic block copolymer mPEG-b-P(RA-SA)-b-mPEG have a remarkable potential as a carrier for hydrophobic drug delivery in cancer therapy. [ABSTRACT FROM AUTHOR]

Latent heat thermal energy storage system using phase change materials was widely used in solar thermal systems. Here, a novel form-stable phase change composite was successfully prepared. The sebacic acid is encapsulated by carbon nanotube sponge. The as-prepared composite is determined by SEM, FT-IR and XRD and the results show that the paraffin is mostly encapsulated in the pores of carbon nanotube sponge. The DSC measurements indicate that the melting temperature and latent heat of the composite are 121.1 °C and 131.8 J g −1 , respectively. The phase change composite could maintain its phase transition perfectly after 200 melting−freezing cycles, and no leakage of sebacic acid was observed by further SEM observation. The as-prepared composite shows 27-fold thermal conductivity enhancement as compared to the pure sebacic acid. Further, the as-prepared composite shows great photo-thermal performance when under simulated solar irradiation. Hence, the carbon nanotube sponge based high temperature phase change composite has great potential in solar thermal application. [ABSTRACT FROM AUTHOR]