A simple method for incorporating amine groups in hydrogenated castor oil (HCO) to produce wax for beeswax or carnauba wax substitution in packaging and coating was developed. From the conversion rate of the products, HCO was reacted with ethanolamine at 150°C for 5 h, and the molar ratio of HCO and ethanolamine was 1:4. The hardness of the final product was seven times higher than that of beeswax, the cohesiveness of the final product was 1.3 times higher than that of beeswax and approximately one half of that of carnauba wax, and the melting point of the final product is 98°C. The Fourier transform Infrared spectroscopy showed that the amide groups were incorporated to form the amide products. In coating application, the results showed that the force of the final product coating cardboard was higher than that of beeswax and paraffin wax and less than that of carnauba wax. After 24 h soaking, the compression forces were decreased. HCO fatty acid wax can be an alternative wax for carnauba wax and beeswax in coating applications.
The article deals with the use of mixed anhydrides for the synthesis of fatty esters. Both aliphatic and aromatic acids are involved, indicating different behaviors according to the chain length of the aliphatic acid. We describe a novel and efficient method for the synthesis of fatty esters by the esterification reaction of primary, secondary and tertiary alcohols with mixed carboxylic-palmitic anhydrides using resin Amberlyst-15 as heterogeneous acid catalyst. Influence of various reaction parameters such as molar ratio (anhydride/alcohol), catalyst amount, type of alcohol and type of mixed anhydride were studied to optimize the conditions for maximum yield. Among tested anhydrides we quote mainly the 4-chlorobenzoic palmitic anhydride because it was both reactive and selective for the preparation of palmitic acid ester. This anhydride gave a good yield of palmitic ester.
Liquid detergents are more convenient than powdered detergents as they dissolve readily in water, generate less dust and dosing is easy. However, the stability of liquid detergents is an issue of concern. Therefore, the objective of this research is to study the formulation requirement to produce heavy-duty liquid detergents based on palm-based methyl esters sulphonate (MES) with desirable properties and performance. MES is produced from renewable and sustainable feedstock suitable to replace the conventional fossil-based surfactant, linear alkyl benzene sulphonates (LAS). Five palm-based liquid detergents (PBLDs) were formulated using C16/18 MES as the primary surfactant. The physical properties, washing performance, stability and biodegradability of PBLDs were evaluated. Performance of the PBLDs was evaluated against two commercial liquid detergents which use LAS and alcohol glucoside as surfactant (benchmark product) and it was found that the PBLDs exhibited excellent performance. PBLDs can be formulated with or without phosphates and still demonstrate good detergency. The stability study of PBLDs indicated that no appreciable hydrolysis occurred. PBLDs exhibited better biodegradability profiles compared to commercial detergent containing LAS. PBLDs passed the 60% biodegradability level within 3 to 8 d, while commercial detergent took 24 d. It was shown that palm-based C16/18 MES could be potentially formulated into liquid detergents and gave better performance than LAS based liquid detergent. Attributes of C16/18 MES should not be overlooked, which include an abundant and naturally derived palm stearin as raw material and environmental safety profiles that are superior to most synthetic surfactants.
The present study investigates the adsorption of the three-phase emulsion on various solid/water interfaces. Vesicles can be used as emulsifiers in the three-phase emulsions and act as an independent phase unlike the surfactant used in conventional emulsions; therefore, it is expected that the three-phase emulsion formed by the adhesion of vesicles to the oil/water interface will adsorb on various solid/water interfaces. The cationic three-phase emulsion was prepared to encourage emulsion adsorption on negatively charged solid substrates in water. The emulsifier polyoxyethylene-(10) hydrogenated castor oil was rendered cationic by mixing with the surfactant cetyltrimethylammonium bromide and then used to prepare the cationic three-phase emulsion of hexadecane-in-water. Three solid substrates (silicon, glass, and copper) were dipped in the cationic emulsion and the emulsion was found to adsorb on the solid substrates while maintaining its structure. The amount of hexadecane adsorbed on the various surfaces was investigated by gas chromatography and found to increase with increasing hexadecane concentration in the emulsion and eventually plateaued just like molecular adsorption. The maximum surface coverage of the emulsion on the substrates was approximately 80%. However, even the equivalent nonionic three-phase emulsion was found to adsorb on the three solid surfaces. This was attributed to a novel mechanism of irreversible adhesion via the van der Waals attractive force.
Surface modification of PDMS, polycarbonate, and acrylic resin was examined using various methacryl polymers bearing sulfobetaine, phosphoryl choline, and oligoethylene glycol units. We have found that zwitterionic polymers are adsorbed on the PDMS surface treated with plasma. The surface of PDMS is stable to keep high hydrophilicity after a month of the modification. On the other hand, one of sulfobetaine polymers showed distinguished adsorption behavior in the case of polycarbonate surface treated with plasma. Suppression effect for nonspecific adsorption of BSA was evaluated using polycarbonate and acrylic resin modified with the polymers. The modified surfaces showed suppression effect for nonspecific adsorption of BSA compared with the surface only treated with plasma.
The partition coefficients, Kx, of 1,2-alkanediols and α,ω-alkanediols between dodecyltrimethylammonium bromide (DTAB) micelles and water, and the change of the degree of counterion dissociation, dα/dXam, on DTAB micelles associated with solubilization of the alkanediols are determined by a differential conductivity technique. The standard Gibbs energy change of transfer per methylene group, ΔG0(CH2), is estimated from a dependence of logarithmic value of the Kx on the carbon number of alkyl chain in the alkanediols. The dα/dXam is independent of the carbon number of alkyl chain in the alkanediols. Comparing the present results with those of DTAB/1-alkanols system, it is suggested that solubilization states of the alkanediols in DTAB micelles are as follows: 1,2-alkanediols are solubilized as its alkyl chain is oriented to micellar interior just like 1-alkanols, while α,ω-alkanediols are solubilized as its alkyl chain is partly located in micellar surface region.
Although several studies have reported the effects of long-chain polyunsaturated fatty acid (LCPUFA) supplementation on the mood in healthy adults, the effects of LCPUFA on elderly individuals remain unclear. Thus, we hypothesized that LCPUFA supplementation improves mood in the elderly. To address this hypothesis, 115 elderly Japanese men aged 55-64 years were assigned and randomly allocated to the LCPUFA or placebo group. Participants received 4 weeks of supplementation with LCPUFA-containing oil (docosahexaenoic acid (DHA) 300 mg/day, eicosapentaenoic acid (EPA) 100 mg/day, arachidonic acid (ARA) 120 mg/day) or a placebo oil. Mood was assessed using the Profile of Mood States (POMS) before and after supplementation as the secondary outcome in a previously performed randomized controlled trial on cognitive function. A total of 113 participants completed the supplementation period. One hundred participants (LCPUFA, n = 51; placebo, n = 49) who were eligible for evaluation of mood were analyzed. Increases in vigor scores on POMS, reflecting a positive mood, were significantly larger in the LCPUFA group than in the placebo group (LCPUFA, +1.8; placebo, −0.5). No significant differences were observed in changes in other negative mood scores between groups. DHA and ARA content in plasma phospholipids were increased by 0.8% and 0.7%, respectively, in the LCPUFA group, and were significantly larger than those in the placebo group. Dietary DHA, EPA, and ARA intake was unchanged during the study. These results suggest that LCPUFA supplementation may improve vigor (positive mood) in elderly Japanese men.
Conjugated linoleic acids (CLA) intake has been reported to reduce body fat mass or increase lean body mass and to improve exercise outcome by modulating testosterone in humans. These reports have studied mostly overweight subjects; few were athletes. Therefore, in this study, the effect of CLA intake on endurance performance and anti-fatigue in student athletes was investigated. A double-blind, crossover study was conducted with 10 male student athletes. Each subject was administered with either CLA (net 0.9 g/day) or a placebo for 14 days. They were subjected to an exercise tolerance test (steady loading) using a cycle ergometer on days 0 and 14. Peak VO2 was determined for each subject using a graded loading test. The steady loading test was performed with a pedaling exercise load of 50% peak VO2 for 40 min and then with a load of 70% peak VO2 until exhaustion. Blood sampling and measurement of critical flicker frequency (CFF) were performed before and after exercise. The rate of perceived exertion (RPE) was measured serially during exercise. In the results, amount of body weight variation significantly increased and amount of body fat percentage variation tended to decrease by CLA intake, it might have an effect by increase in muscle mass. In addition, amount of exercise time variation significantly increased, amount of variation of CFF before and after exercise tended to increase, that of RPE during exercise tended to decrease, and that of creatine phosphokinase before and after exercise tended to decrease in the CLA group. These results suggested that CLA intake for 14 days might have an effect on endurance performance and anti-fatigue in student athletes.
The present study was carried out to know the sorption mechanism of Pb (II) and Ni (II) in aqueous solution using pea peels under the influence of sorbent dose, pH, temperature, initial metal ion concentration and contact time. SEM and FTIR were used for characterization of pea peels. The study showed that solution pH affects sorption process and the optimum pH for Pb (II) was 6.0 while for that of Ni (II) was 7.0. Pseudo-second order kinetic model was found to be the most suitable one to explain the kinetic data not only due to high value of R2 (>0.99) but also due to the closeness of the experimental sorption capacity values to that of calculated sorption capacity values of pseudo second order kinetic model. It can be seen from the results that Freundlich isotherm explains well the equilibrium data (R2>0.99). Sorption capacity of pea peels was 140.84 and 32.36 for Pb (II) and Ni (II) mg g–1 respectively. The positive value of ΔH° and negative values of ΔG° suggest that sorption of Pb (II) and Ni (II) onto pea peels is an endothermic and spontaneous process respectively.
3-oxohexadecanoyl-CoA was synthesized for the study of D-bifunctional protein (EC 4. 2. 1. 107, EC 4. 2. 1. 119, EC 1. 1. 1. n12) and L-bifunctional protein (EC 4. 2. 1. 17, EC 5. 3. 3. 8, EC 1. 1. 1. 35). First, tetradecanal was subjected to the Reformatsky reaction with ethyl bromoacetate, and the product was then converted into ethyl 3-oxohexadecanoate. After acetalization of the 3-oxo ester with ethylene glycol, 3,3-ethlenedioxyhexadecanoic acid was obtained by alkaline hydrolysis. The acid was condensed with coenzyme A (CoA) by the mixed anhydride method, and the resulting CoA ester was deprotected with 4 M HCl to obtain 3-oxohexadecanoyl-CoA. In addition, the behavior of the CoA ester under several conditions of high-performance liquid chromatography (HPLC) was also investigated. We established separation detection of (R)-3-hydroxyhexadecanoyl-CoA, (S)-3-hydroxyhexadecaboyl-CoA, 3-oxohexadecanoyl-CoA, and trans-2-hexadecenoyl-CoA.
Estolides of ricinoleic acid (RA) have been used as lubricants and pigment dispersant in many industries. In this paper, functional acid ionic liquids (ILs) were firstly used as catalysts to prepare RA estolides by the esterification of RAs in solvent-free system. Different ILs were used as catalysts for the esterification. Effect of reaction variables (IL amount, reaction temperature and reaction time) on the esterification were also investigated and optimized using response surface methodology (RSM). Among all tested ILs, [BSO3HMIM]TS showed the best performance for the esterification. Arrhenius equation for the esterification was lnV0 =14.897-7558.7/T, and the activation energy (Ea) was 62.84 kJ/mol. A high degree of polymerization with an acid value of 48.0±2.5 mg KOH/g was achieved at the optimized conditions (IL load 12%, reaction temperature 140°C, and reaction time 12 h). The effect of reaction variables on the esterification decreased in the order of catalyst loading of IL > reaction temperature > reaction time.
Starfish oil (SO) is characterized by functional lipids, including n-3 polyunsaturated fatty acid (both in the form of triacylglycerol and in the form of phospholipid), and carotenoids, which may exert beneficial effects on metabolic disorders in obesity-associated diseases. In the present study, the effect of SO on dysregulation of lipid metabolism was examined using C57BL/6N mice treated with high-fat (HF) diet. Mice were fed HF, HF with 2% SO, or HF with 5% SO diet for 8 weeks. Weight gain, blood glucose, serum and hepatic lipid contents, and hepatic fatty acid composition were measured. Fatty acid β-oxidation activity was monitored by measuring the catabolic rate of 13C-labeled fatty acid, assessed as 13CO2/12CO2 ratio using isotope ratio mass spectrometry (IR-MS). Although there were no differences in body weight or white adipose tissue weight among the test groups, dietary SO reduced blood glucose, and dose-dependently improved hyperlipidemia and decreased hepatic lipid accumulation. Analysis of hepatic fatty acid composition revealed a significant decrease in the ratio of monounsaturated fatty acid to saturated fatty acid, which is attributed to stearoyl-CoA desaturase activity. IR-MS analysis suggested that β-oxidation activity was enhanced in the mice treated with 5% SO. These results demonstrate that dietary SO improves lipid metabolism measures in HF diet-induced obese mice, suggesting that SO holds promise as an agent for the prevention and treatment of lipid metabolism disorders in the liver.
A novel adsorbent, palm fatty acid coated magnetic Fe3O4 nanoparticles (MNP-FA) was successfully synthesized with immobilization of the palm fatty acid onto the surface of MNPs. The successful synthesis of MNP-FA was further confirmed by X-Ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR) and Energy dispersive X-Ray spectroscopy (EDX) analyses and water contact angle (WCA) measurement. This newly synthesized MNP-FA was applied as magnetic solid phase extraction (MSPE) adsorbent for the enrichment of polycyclic aromatic hydrocarbons (PAHs), namely fluoranthene (FLT), pyrene (Pyr), chrysene (Cry) and benzo(a)pyrene (BaP) from environmental samples prior to High Performance Liquid Chromatography- Diode Array Detector (HPLC-DAD) analysis. The MSPE method was optimized by several parameters such as amount of sorbent, desorption solvent, volume of desorption solvent, extraction time, desorption time, pH and sample volume. Under the optimized conditions, MSPE method provided a low detection limit (LOD) for FLT, Pyr, Cry and BaP in the range of 0.01-0.05 ng mL–1. The PAHs recoveries of the spiked leachate samples ranged from 98.5% to 113.8% with the RSDs (n = 5) ranging from 3.5% to 12.2%, while for the spiked sludge samples, the recoveries ranged from 81.1% to 119.3% with the RSDs (n = 5) ranging from 3.1% to 13.6%. The recyclability study revealed that MNP-FA has excellent reusability up to five times. Chromatrographic analysis demonstrated the suitability of MNP-FA as MSPE adsorbent for the efficient extraction of PAHs from environmental samples.
Sixty Bacillus subtilis strains were investigated for their ability to produce cyclic lipopeptides (CLPs). Among them, B. subtilis NBRC 109107 produced at least three types of CLPs by high-performance liquid chromatography (HPLC) analysis, and these CLPs were thought to be surfactin, iturin A, and fengycin by polymerase chain reaction amplification of respective CLP synthetase-encoding genes. However, after HPLC fractionation and purification, structural analysis of the CLPs revealed that these were surfactin homologues, iturin A, and unknown CLPs, whose surface-tension-lowering activities were 29.4, 56.7, and 48.6 mN/m, respectively. By contrast, fengycin was not detected.
Here, we describe a new method for genetic transformation of thraustochytrids, well-known producers of polyunsaturated fatty acids (PUFAs) like docosahexaenoic acid, by combining mild glass (zirconia) bead treatment and electroporation. Because the cell wall is a barrier against transfer of exogenous DNA into cells, gentle vortexing of cells with glass beads was performed prior to electroporation for partial cell wall disruption. G418-resistant transformants of thraustochytrid cells (Aurantiochytrium limacinum strain SR21 and thraustochytrid strain 12B) were successfully obtained with good reproducibility. The method reported here is simpler than methods using enzymes to generate spheroplasts and may provide advantages for PUFA production by using genetically modified thraustochytrids.
The reactivity and detergency of a horseradish peroxidase reaction system with oleic acid, a non-hydrogen donor used as a soil component, were studied. Under a coexistent system of horseradish peroxidase and p-iodophenol, oleic acid decomposed quickly. In addition, because the coexistence of p-iodophenol provided detergency, a new function of horseradish peroxidase was shown.
Important Announcement for the Contributors of the Journal of Oleo Science;
At 0:00 AM on April 1, 2016 (Japan time), the Journal of Oleo Science will start charging Publication Charge for each case; 1: 20,000 yen (within 8 pages. /more than 8 pages, additional charge is necessary; 2,000 yen per page) for Members of Japan Oil Chemists’ Society (JOCS) (including Asian Members and Support Members), 2: 40,000 yen (within 8 pages. /more than 8 pages, additional charge is necessary; 4,000 yen per page) for Non-Members of JOCS.
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