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Showing papers in "Journal of Oleo Science in 2005"


Journal ArticleDOI
TL;DR: It is demonstrated that DMH-induced ACF formation could be inhibited in mouse large intestine by maize and yeast cerebrosides, which may serve to suppress colon carcinoma in humans.
Abstract: For clarification of physiological effects of dietary maize and yeast sphingolipids on colon cancer in vivo, we investigated the effects of dietary maize and yeast cerebrosides on 1,2-dimethylhydrazine (DMH) -induced aberrant crypt foci (ACF) formation in mouse large intestine. After 10 weeks of maize and yeast cerebroside feeding and DMH administration, DMH-induced ACF formation was significantly suppressed in all large intestines of these mice. When lipids in the feces of mice fed maize and yeast cerebrosides were analyzed, maize and yeast cerebrosides decomposed by intestinal enzyme and/or microflora were observed. The present study demonstrated that DMH-induced ACF formation could be inhibited in mouse large intestine by maize and yeast cerebrosides. Daily ingestion of these compounds may serve to suppress colon carcinoma in humans.

54 citations


Journal ArticleDOI
TL;DR: In this article, an inhibitory compound was identified from the ethyl acetate extract and identified as sitosterol-β -D-glucopyranoside (1) by EI-MS, FAB-MS and IR, 1H and 13C NMR spectroscopy.
Abstract: Methanol extract from Arctium lappa L. showed an inhibitory activity of α-glucosidase. The methanol extract was re-extracted with ethyl acetate and water. The ethyl acetate extract showed inhibitory activity. The inhibitory compound was isolated from the ethyl acetate extract and identified as sitosterol-β -D-glucopyranoside (1) by EI-MS, FAB-MS, IR, 1H and 13C NMR spectroscopy. Compound 1 inhibited 97.3% of α-glucosidase activity at a concentration of 200.0 μ mol/mL, and the ID50 (50% inhibition dose) value was 30 μ mol/mL. In addition, the inhibitory compounds from the ethyl acetate extract were also identified as methyl palmitate (2), methyl linoleate (3) and methyl linoleneate (4) by GC-MS analysis. Compound 2-4 inhibited 73.4%, 66.5% and 68.5% of α-glucosidase activity at a concentration of 200 μ mol/mL, and the ID50 values were 52.8, 47.5 and 46.7 μ mol/mL. To research the structure-activity relationship, methyl steareate (5), methyl oleate (6), palmitic acid (7), linoleic acid (8), linolenic acid (9), stearic acid (10) and oleic acid (11) were also assayed.

44 citations


Journal ArticleDOI
TL;DR: It is concluded that the study product is useful as a food additive that improves serum cholesterol concentrations and is expected to decrease the risk of atherosclerosis for people with a slightly elevated total cholesterol level.
Abstract: We performed a clinical study using healthy male and female subjects who had slightly elevated cholesterol levels in their serum to examine the effects of food tablets containing apple polyphenols (Applephenon®), which are effective for improving serum cholesterol concentrations in rats, on lipid metabolism in humans. The total period of this study was four weeks and we obtained blood samples at week 0 and week 4. Total cholesterol levels of the intervention groups decreased significantly and dose-dependently compared with that of the control group. We also found LDL-cholesterol decreased significantly and HDL-cholesterol increased. No abnormalities were detected in biochemical examinations of any of the subjects during the test period. We concluded that the study product is useful as a food additive that improves serum cholesterol concentrations. Such improvement is expected to decrease the risk of atherosclerosis for people with a slightly elevated total cholesterol level.

43 citations


Journal ArticleDOI
TL;DR: In this paper, the scale-up synthesis of wax esters by alcoholysis of palm oil (PO) with oleyl alcohol (OA) using Lipozyme in a bioreactor was investigated.
Abstract: Wax esters, one of the important ingredients in cosmetic industry, are long-chain esters that exhibit wetting behavior with non-greasy feeling. Wax esters derived from long chain fatty acids and long chain alcohols with chain lengths of 12 carbons or more. These compounds have many potential applications in cosmetics, pharmaceutical and food industries. The present work focuses on the scale-up synthesis of wax esters by alcoholysis of palm oil (PO) with oleyl alcohol (OA) using Lipozyme in a bioreactor. Response surface methodology (RSM) and a 5-level-5-factor central composite rotatable design were adopted to evaluate the effects of synthesis parameters, such as temperature (40-60°C), amount of enzyme (14-22% by weight of PO), amount of palm oil (80-240 mmol), amount of oleyl alcohol (240-720 mmol) and impeller speed (100-400 rpm) on the percentage yield of palm-based wax esters. Based on Design Expert Software (version 6.0.4), optimum alcoholysis conditions were: temperature, 50.4°C, amount of enzyme, 16.0% by weight of palm oil, amount of palm oil, 200.0 mmol, amount of oleyl alcohol, 600.0 mmol, palm oil/oleyl alcohol ratio, 3:1 and impeller speed, 242.1 rpm. The corresponding predicted value of percentage yield and productivity was 91.5% and 106.4 mmol/h respectively compared to the actual experimental value 92.3% yields and 110.8 mmol/h productivity.

38 citations


Journal ArticleDOI
TL;DR: Oleyl oleate, a liquid wax ester was synthesized by an immobilized Candida antartica lipase B (Novozym 435) as biocatalyst using oleic acid and oleyl alcohol as mentioned in this paper.
Abstract: Oleyl oleate, a liquid wax ester was synthesized by an immobilized Candida antartica lipase B (Novozym 435) as biocatalyst using oleic acid and oleyl alcohol. The effects of various reaction parameters were optimized to obtain a high yield of liquid wax esters. Investigation in large scale production was performed in batch mode of stirred tank reactor (STR) with one multi-bladed impeller. The optimum condition to produce liquid wax ester was, reaction time (RT); 30 min, temperature (T); 50 °C, amount of enzyme (E); 90 g (900,000 PLU), agitation speed (A) of 400 rpm, number of impeller tip (N) of 2 and molar ratio of oleyl alcohol to oleic acid (M); 2:1. Analysis of the yield showed that at optimum condition, >90% liquid wax esters were produced. The stability of Novozym 435 showed at high percentage (>80%) up to 4 cycles.

30 citations


Journal ArticleDOI
TL;DR: Bis(sodium sulfate) surfactants each bearing two alkyl groups were easily prepared by acid-catalyzed transesterification of diethyl tartrate with fatty alcohols and subsequent sulfation with sulfamic acid without any expensive reagents and special equipment.
Abstract: Bis(sodium sulfate) surfactants each bearing two alkyl groups were easily prepared by the acid-catalyzed transesterification of diethyl tartrate with fatty alcohols (octyl, decyl, or dodecyl) and subsequent sulfation with sulfamic acid without any expensive reagents and special equipment. These surfactants had better water-solubility, smaller critical micelle concentration (cmc) and lower surface tension at cmc compared to sodium dodecylsulfate and sodium tetradecylsulfate. These surfactants bearing octyl or decyl chains had low-foaming properties and good solubility in hard water. They decomposed easily into nonsurface-active species under acidic or alkaline conditions. Their biodegradabilities were almost the same as that of sodium dodecanoate.

26 citations


Journal ArticleDOI
TL;DR: The salt-fermented shrimp paste was found to obtain potent antioxidative substances and large amount of EPA, DHA, and amino acids, and it is expected to act as an effective antioxidant in the authors' body and to be a good source of these nutrients.
Abstract: Shrimp (Acetes sp.) was mixed with salt in a ratio of 3:1 and allowed to ferment at room temperature (28-30°C). From the shrimp paste samples collected at the initial (1 day) and end (10 days) of fermentation, 85% ethanol extracts were prepared for their antioxidative assays. Both extracts exhibited high free radical scavenging property against 1,1 diphenyl 2-picrylhydrazyl and suppressed peroxidation of methyl linoleate initiated by 2,2′azobis 2-amidinopropane dihydrochloride. These antioxidative activities, however, did not change significantly during fermentation for 10 days, thus suggesting that the observed antioxidative activities could have mainly due to original antioxidants present in shrimp but not to its fermentative products. The salt-fermented shrimp samples contained large amount of polyunsaturated fatty acids including EPA and DHA, although the polar lipids like phospholipids were hydrolyzed during fermentation to produce the corresponding amount of free fatty acids. In addition, free amino acids of the shrimp sample significantly increased during the fermentation and could be responsible for the unique flavor of salt-fermented shrimp paste. Since the salt-fermented shrimp paste was found to obtain potent antioxidative substances and large amount of EPA, DHA, and amino acids, it is expected to act as an effective antioxidant in our body and to be a good source of these nutrients.

26 citations



Journal ArticleDOI
TL;DR: In this article, the compositions of the essential oil from woods of Prunus mume Sieb et al. (ume), have been investigated by capillary GC and GC/MS, and the oil was found to contain 97 components, representing 92.41% of the total oil.
Abstract: The compositions of the essential oil from woods of Prunus mume Sieb. et Zucc. (ume), have been investigated by capillary GC and GC/MS. The oil was found to contain 97 components, representing 92.41% of the total oil. The main constituents were 6,10,14-trimethyl-2-pentadecanone (15.83%), α-acorenol (9.36%), (Z)-α-bisabolene (7.49%), benzaldehyde (3.87%), isopropyltiglate (3.84%), terpinen-4-ol (3.41%).

22 citations


Journal ArticleDOI
TL;DR: In this paper, the Mandarin peels were pre-treated with enzyme by varying its concentration from 0.1% to 0.3% and the increase in the yield of essential oil as compared to control samples obtained were up to 15%.
Abstract: The Mandarin (Citrus reticulata) peels were utilized for recovery of essential oil. The essential oil is one of the important ingredients widely used in various food products. The flavedo part of peels of mandarin fruit was utilized for extraction of essential oil by hydro-distillation method and cold pressing extraction method. The peels were pre-treated with enzyme by varying its concentration from 0.1% to 0.3%. Essential oil was recovered from these enzyme treated samples and yield obtained was compared with control samples. By varying the concentration of enzyme in pre-treatment the increase in the yield of essential oil as compared to control samples obtained were up to 15%. This increase in recovery may be due to rupture of oil sacs/glands by enzymatic action, resulting excess release of essential oil from oil sacs. The effect of concentration of enzyme at pH 4.5 and contact time 3 hrs on the yield obtained was studied during extraction.

20 citations


Journal ArticleDOI
TL;DR: Taking into account the drawbacks and benefits of oils and fats, the production of Structured Lipids (SLs) containing especial fatty acids has been now a days attracting more and more attention.
Abstract: Awareness regarding the harmful effects of excessive oils and fats intake is universal. Consequently, health conscious individuals are modifying their dietary habits and eating less fat , as high fat intake specially saturated fat is associated with increased risk for obesity, high blood cholesterol, coronary heart disease, cancer, and arteriosclerosis. Although oils and fats are not only the concentrated source of energy but also the source of essential fatty acids (EFA). Taking into account the drawbacks and benefits of oils and fats, the production of Structured Lipids (SLs) containing especial fatty acids has been now a days attracting more and more attention.

Journal ArticleDOI
TL;DR: In this paper, simple, rapid and reliable colour tests such as Sodium azide test, Modified nitric acid test, Azo dye test, Boudouin test, Hexabromide test and Halphen's test, Molybdate method and Solvent partition test have been reported for the detection of adulterants in edible oils.
Abstract: In the present paper, simple, rapid and reliable colour tests such as Sodium azide test, Modified nitric acid test, Azo dye test, Boudouin test, Hexabromide test, Halphen’s test, Molybdate method and Solvent partition test have been reported for the detection of adulterants in edible oils. These are performed for synthetic mustard oil, argemone oil, physically refined rice bran oil, sesame oil, linseed oil, cottonseed oil, castor oil and palmolein respectively (respective sensitivity level as 0.1%, 0.1%, 2.5%, 0.2%, 1.0%, 0.5% and 2.0%).

Journal ArticleDOI
TL;DR: In this article, the authors examined the effects of sugar addition on the hydrophile-lipophile balance of polyoxyethylene sorbitan monooleate (MOPS) and the D phase emulsification of triglyceride by MOPS.
Abstract: Sucrose, D-glucose and D-maltose were examined for their effects on the hydrophile-lipophile balance (HLB) of polyoxyethylene sorbitan monooleate (MOPS) and the D phase emulsification of triglyceride by MOPS. With rise in concentration, each was found to decrease HLB of MOPS with reduction in MOPS cloud point. In the phase diagram of the MOPS/aqueous solution/triglyceride three component system, the D phase region was noted to expand with sucrose addition. Regardless of the sugar, an O/D emulsion gel formed at high triglyceride content on adding oil to a 40 wt% aqueous sugar and MOPS mixture. Mean O/W emulsion droplet size subsequent to O/D emulsion gel dilution was ca.1 μm while with agent-in-oil emulsification, ca. 10 μm. Droplet distribution of the emulsion prepared by agent-in-oil emulsification was broad and that of the emulsion produced by D phase emulsification, narrow. It thus may be concluded that the addition of sugars as the 4th ingredient to a MOPS/water/triglyceride system is a promising means for D phase emulsification in the industry.

Journal ArticleDOI
TL;DR: In this article, the use of immobilized lipase as the catalyst for the preparation reaction provides an easy isolation of the enzyme from the products and other components in the reaction mixture and also allows the reaction to be carried out under mild conditions, which reduces the reaction's side products.
Abstract: Fatty hydroxamic acids (FHA) have been successfully synthesized from palm oils by a one-step lipase catalyzed reaction. The use of immobilized lipase as the catalyst for the preparation reaction provides an easy isolation of the enzyme from the products and other components in the reaction mixture. In addition, it also allows the reaction to be carried out under mild conditions, which reduces the reaction’s side products. The percentages of conversion of commercial palm olein (CPOn), RBD (refined, bleached and deodorized) palm olein (POn), RBD palm oil (PO), RBD palm stearin (PS) and RBD palm kernel olein (PKOn) into their fatty hydroxamic acids are 89, 79, 77, 90 and 98, respectively.

Journal ArticleDOI
TL;DR: In this paper, the phase behavior of environment-friendly surfactants, polyoxyethylene phytosterylether (PhyEOm) in water and C12EO4 systems was studied.
Abstract: The phase behavior of environment-friendly surfactants, polyoxyethylene phytosterylether (PhyEOm) in water and water/polyoxyethylene dodecylether (C12EO4) systems was studied. In the PhyEO10/water binary system, micellar solution (Wm), unidentified optically anisotropic liquid crystal (X) phase and lamellar (L α) phases are formed successively with increasing surfactant concentration at room temperature. With hydrophilic PhyEO20, the Wm, micellar cubic and hexagonal phases are formed in the binary system. With addition of C12EO4 to the dilute micellar solution of both PhyEOm type surfactants, a highly viscoelastic solutions of worm-like micelles are formed. Addition of C12EO4 to the liquid crystalline phases formed in binary system results in the formation of the L α phase, which extends over wide concentration range. In the PhyEO10/C12EO4/water system, the X-Lα phase transformation occurs via rectangular ribbon phase. The phase behavior of 5% PhyEOm with various EO-chain length, ranging from m = 5 to 20 was studied in a wide range of temperature (20°-100 °C). A phase separation occurs in the lipophilic PhyEOm (m < 8) aqueous systems at all temperature. In the PhyEOm with intermediate EO-chain length (11 < m < 16), small micelles undergo enormous one-dimensional growth upon increasing the temperature and form viscoelastic solution, followed by a phase separation; whereas in the long EO-chain PhyEOm (m = 17-20), the Wm phase of small aggregates exists in the entire temperature range.

Journal ArticleDOI
TL;DR: It is concluded that flaxseed oil consumption has a statistically significant effect on slowing bleeding time thus likely reducing the risk of myocardial infarction and that such effect is more profound in males than females suggesting a greater efficacy of flax Seed Oil administration for type 2 diabetic males.
Abstract: Platelet hyper-aggregation is a serious manifestation of type 2 diabetes and a precipitating factor in the most frequent cause of death in type 2 diabetes-myocardial infarction. Consumption of flaxseed oil as a dietary supplement containing alpha-linolenic acid (ALA, 18:3 n-3) through its metabolism to eicosapentaenoic acid (EPA, 20:5 n-3) and subsequent production of anti-aggregatory eicosanoids may reduce such aggregation in vivo. Lp (a) may also influence platelet aggregation in vivo. Furthermore, serum Lp(a) concentrations are increased and bleeding time is decreased in type 2 diabetics presenting an enhanced risk of myocardial infarction. It was hypothesised that Lp(a) and bleeding time would be correlated due to the considerable molecular homology between apolipoprotein (a) and plasminogen which should decrease bleeding time. Bleeding time is an excellent measure of in vivo platelet aggregability. One purpose of this study was to determine the impact flaxseed oil consumption on bleeding time compared to those on safflower oil and to determine the impact of Lp(a) on bleeding time. It was a secondary purpose to determine if there were any gender differences pre- or pre-post treatment in bleeding time. Subjects (N = 40) were randomly divided to take either the treatment, flaxseed oil (N = 20) or the placebo, safflower oil (N = 20). Each of the treatment or placebo groups contained equal numbers of males (N = 10) and females (N = 10). Some subjects dropped from the study due to reasons not related to treatment side effects. Subjects came for 3 visits, each 3 months apart. On each visit age, gender and BMI were recorded and bleeding time was performed. At the completion of visit 2, subjects were randomly assigned to take 1 gram of oil per 10 kg body weight each day for 3 months. Comparing pre- and post-treatment, there was a statistically significant increase in bleeding time in the flaxseed oil group including each of males and females while there was no change in the safflower group in total or by gender. Males had a statistically shorter bleeding time pre-treatment while males and females showed no difference post-treatment with flaxseed oil consumption. Males and females showed a non-significant correlation and statistically significant correlation respectively between pre-treatment values for Lp(a) and bleeding time. The statistically significant correlation also held for the whole population though at a lower value than females. It is concluded that flaxseed oil consumption has a statistically significant effect on slowing bleeding time thus likely reducing the risk of myocardial infarction and that such effect is more profound in males than females suggesting a greater efficacy of flaxseed oil administration for type 2 diabetic males. It is concluded that type 2 diabetic females take better advantage of elevated Lp(a) concentrations than do males thus, at least in part rendering the impact of flaxseed oil on bleeding time greater in males.

Journal ArticleDOI
TL;DR: New troponoid liquid crystals with bis(tropon-2-yl)-4,4'-azobisbenzoate core were prepared in this paper, which had intermolecular π-π interactions between azobenzene planes and between tropone rings.
Abstract: New troponoid liquid crystals with bis(tropon-2-yl)-4,4’-azobisbenzoate core were prepared. Compound (1) had enantiotropic nematic and/or smectic C phase. The crystals of 1a had intermolecular π-π interactions between azobenzene planes and between tropone rings. The nematic liquid crystal (1a) did not form any layer structure in crystal state. X-ray diffraction studies revealed that 1c and 1d formed the tilted layers in the smectic C phase.

Journal ArticleDOI
TL;DR: The 6-methoxy-N-(3-sulfopropyl)quinolinium (SPQ) fluorescence probe was used in this article for measurement of halide concentrations dissociated from the surfactant monomer and micelle.
Abstract: The halide sensitive fluorescence probe, 6-methoxy-N-(3-sulfopropyl)quinolinium (SPQ), provides a direct approach for measurement of halide concentrations dissociated from the surfactant monomer and micelle. The gel filtration method confirms that the water-soluble SPQ probe will tend to partition in aqueous bulk phase without trapping in cationic micelles. The fluorescence of SPQ is quenched by free halide ions with a linear Stern-Volmer relation below the CMC of cationic surfactants. The Stern-Volmer plot gave a distinct break at CMC owing to the counterion binding to micelles. The CMC and degree of micellar counterion binding (β) are generally in agreement with those obtained by conductivity method. The SPQ fluorescence quenching had high sensitivities with Stern-Volmer constants of 125 M-1 (chloride) and 223 M-1 (bromide), while it was insensitive to nitrate ion. The selective quenching behavior shows that the nitrate ions bind to micelles displacing bromide for tetradecyltrimethylammonium micelles. The increase in counterion binding to micellar surface lower the CMC of surfactants, TTAOAc (tetradecyltrimethylammonium acetate) > TTAC (tetradecyltrimethylammonium chloride) > TTAB (tetradecyltrimethylammonium bromide) > TTAN (tetradecyltrimethylammonium nitrate).

Journal ArticleDOI
TL;DR: Characteristics indicate that the novel Vitamin C derivative presented here, VCP-IS-Na, may be effective pro-Vitamin C for skin care application.
Abstract: A novel alkyl ester of Vitamin C derivative, originated in a stable ascorbate derivative, sodium L-ascorbic acid 2-phosphate (VCP-Na), was chemically synthesized. The thermal stability, surface tension, distribution between organic and water phase, and in vitro skin permeability were evaluated. This monoalkyl ester derivative was identified as sodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-Na) by UV spectra, infrared spectra, mass spectra, and nuclear magnetic resonance spectroscopy. The reaction afforded VCP-IS-Na in a high yield (60%). VCP-IS-Na exhibited satisfactory stability in neutral solution comparable to that of a typical stable derivative, VCP-Na. Increased skin permeability was superior to those of VCP-Na and ascorbic acid (VC). VCP-IS-Na that is susceptible to the enzymatic hydrolysis by tissue esterase and/or phosphatase released VC in the skin tissues. Thus, these characteristics indicate that the novel Vitamin C derivative presented here, VCP-IS-Na, may be effective pro-Vitamin C for skin care application.

Journal ArticleDOI
TL;DR: In this article, the authors obtained the degree of counterion binding (β) of dodecylpyridinium bromide and iodide (DPI) and tetradecylpyriniumbromide (TPB) micelles in aqueous sodium halide solutions with concentrations of 0 - 20 mM.
Abstract: From electromotive force measurements with surfactant and halide ion-selective electrodes, we obtained the degree of counterion binding (β) of dodecylpyridinium bromide (DPB) and iodide (DPI) and tetradecylpyridinium bromide (TPB) micelles in aqueous sodium halide solutions with concentrations of 0 - 20 mM. Under a geometrical consideration the micelle shapes and the surface densities of head group (s-1) of these micelles were deduced from aggregation numbers evaluated from their relationships to the added salt concentration previously reported. The spherical micelles of TPB having the shape of an oblate ellipsoid had a constant β, 0.76, independently of s-1. In the case of the spherical micelles of DPB, β was found to be 0.79 for sphere-shaped micelles and 0.82 for ellipsoidal ones. For DPI we obtained β values of 0.84 and 0.99 for the spherical micelles with the shape of an oblate ellipsoid and the rodlike micelles, respectively. From these dependences of β on micelle shape and s-1, we conclude that β of micelles investigated increases in the order of sphere-shaped < oblately ellipsoidal < rodlike micelles but is independent of the micelle size unless the micelle shape changes.

Journal ArticleDOI
TL;DR: The shape of mixed dipalmitoylphosphatidylcholine (DPPC)/stearylamine (SA) liposomes prepared by the Bangham method was examined using freeze-fracture electron microscopy and indicated that the shape of the DPPC/SA liposome is that of LUVs.
Abstract: The shape of mixed dipalmitoylphosphatidylcholine (DPPC)/stearylamine (SA) liposomes prepared by the Bangham method was examined using freeze-fracture electron microscopy. The shape of the mixed DPPC/SA liposomes (XSA = 0.05) was not that of multilamellar vesicles (MLVs) but large unilamellar vesicles (LUVs) with a diameter of approximately 1.0 μm. These facts overthrow the preconceived idea that the shape of the DPPC/SA liposomes prepared by the Bangham method is that of MLVs. The trapping efficiency of the mixed DPPC/SA liposomes (XSA = 0.05) was ten times greater than that of the DPPC liposomes, since the DPPC liposomes were MLVs. The data of the DSC peak for the DPPC/SA liposomes also indicated that the shape of the DPPC/SA liposomes is that of LUVs. We emphasize that the shape of the DPPC liposomes changes from that of MLVs to LUVs by the mixing of a small amount of SA into the DPPC liposomes.

Journal ArticleDOI
TL;DR: In this article, sulfate-type hybrid surfactants with an ethylene spacer in their molecule, CmF2m+1C2H4CH(OSO3Na)CnH2n+1 (FmEHnOS: m = 4, 6, 8; n = 3, 5, 7), were synthesized.
Abstract: Nine sulfate-type hybrid surfactants with an ethylene spacer in their molecule, CmF2m+1C2H4CH(OSO3Na)CnH2n+1 (FmEHnOS: m = 4, 6, 8; n = 3, 5, 7), were synthesized. FmEHnOS were obtained in a yield higher than those for the hybrid surfactants previously synthesized. While FmEHnOS were hardly susceptible to hydrolysis in aqueous weakly acidic through strongly alkaline media, these surfactants were hydrolyzed in highly acidic media to give alcohol derivatives, FmEHnA. They were highly water-soluble and highly surface-active. Their critical micelle concentrations (cmc) determined by surface tension measurements were about 3.5 times higher than those of sulfate-type hybrid surfactants with a benzene ring spacer, CmF2m+1C6H4CH(OSO3Na)CnH2n+1 (FmPHnOS: C6H4 = p-phenylene), and the cmcs were found to obey the Klevens’ rule. Changes in the chemical shifts of ω-CF3 and ω-CH3 groups in the NMR spectra of the newly synthesized surfactants at different concentrations suggested that the fluorocarbon and hydrocarbon chains in F4EH3OS micelles undergo an intramicellar phase separation. Thermoresponsive surfactant gel formation was observed for 10 wt% F8EH3OS solution.

Journal ArticleDOI
TL;DR: In five acidic glycerophospholipids from grains of japonica and indica rices, phosphatidylglycerol had commonly the lowest unsaturation index and cardiolipin had the highest and the order of unasaturation index in each lipid did not depend on the variety of rice.
Abstract: In five acidic glycerophospholipids (phosphatidylglycerol, phosphatidylinositol, cardiolipin and two N-acyl phospholipids containing ethanolamine) from grains of japonica and indica rices, phosphatidylglycerol had commonly the lowest unsaturation index and cardiolipin had the highest. The order of unasaturation index in each lipid did not depend on the variety of rice. It was assumed that unsaturation index of the lipids changed with temperature during grain ripening except for cardiolipin. Cardiolipin usually had a high level of linoleic acid and a low level of palmitic acid compared with other lipids.

Journal ArticleDOI
TL;DR: In this paper, the micelle concentration and micelle ionization degree for 2-hydroxy-1,1,2,3,3-pentahydropefluoroundecyldiethylammonium halides in D2O were lower than those in H2O.
Abstract: Solvent isotope effects on the micellization behavior of fluorosurfactants have been investigated. The critical micelle concentration and the micelle ionization degree for 2-hydroxy-1,1,2,3,3-pentahydropefluoroundecyldiethylammonium halides in D2O were lower than those in H2O. The stronger hydrogen bonding in D2O enhanced the micelle growth accompanying counterion binding.

Journal ArticleDOI
TL;DR: In this article, an optimization study has been carried out to evaluate synergistic effects of natural antioxidants on physico-chemical characteristics of flaxseed oil during heating, and the results showed that the use of oleoresin rosemary extract, sage extract and citric acid improved the stability of the oil during 20 times of frying.
Abstract: An optimization study has been carried-out to evaluate synergistic effects of natural antioxidants on physico-chemical characteristics of flaxseed oil during heating. Results showed that the use of oleoresin rosemary extract, sage extract and citric acid improved the stability of the oil during 20 times of frying. This study also revealed that the addition of these antioxidants effectively retarded flaxseed oil deterioration after as early as 5 times of frying of potato chips. Analyses from Response Surface Methodology (RSM) indicated that for all physico-chemical characteristics of flaxseed oil evaluated, all mathematical models or equations could be developed with high confidence, where all R2 values greater than 0.87. From this study, the highest R2 (0.98) was shown by yellow colour, followed by absorbance at 268 nm (0.97), saturated /unsaturated fatty acid ratio (0.95), absorbance at 232 nm (0.93), and AnV (0.92). R2 values for four other parameters were 0.88 (PV and IV) and 0.87 (FFA and red colour). This meant that the R2 values obtained from this study were all satisfactory and considered accurate enough, not only for prediction purposes, but also for optimization purposes.

Journal ArticleDOI
TL;DR: In this paper, the authors examined the physicochemical properties and bioactivities of trans eicosapentaenoic acid (TEPA) prepared using p-toluenesulfinic acid.
Abstract: Although trans geometric isomers of unsaturated fatty acids are formed during heat treatment, little is known about the physicochemical properties and the bioactivities of trans eicosapentaenoic acid (TEPA). We examined the oxidative stability and the anti-inflammatory activity of TEPA prepared using p-toluenesulfinic acid. TEPA was more stable to oxidation induced by radical generators than eicosapentaenoic acid (EPA) in organic and in aqueous solutions, and was less suitable as a substrate for 15-lipoxygenase oxidation than was EPA. These results suggest that the trans conformation may be a more stable structure to oxidation. In addition, the release of leukotriene B4 (LTB4) from Ca-ionophore-stimulated rat peritoneal exudate cells (PEC) was not affected by treatment with TEPA, and TEPA was taken up into PEC at lower levels compared to EPA. These results suggest that dietary TEPA has different physiological effects than EPA.

Journal ArticleDOI
TL;DR: In this paper, the authors focus on tuna shavings as a natural resource which hither to has been unused, they contain a high concentration of phospholipids including docosahexaenoic acid (DHA-PL) and are a byproduct of factory processed tuna.
Abstract: The authors focus on tuna shavings as a natural resource which hither to has been unused, they contain a high concentration of phospholipids including docosahexaenoic acid (DHA-PL) and are a by-product of factory processed tuna. Supercritical carbon dioxide (SC-CO2) although a suitable substance in the extraction of non-polar substances (triacylglycerides), has not proven effective in the extraction of polar substances. The efficient use of SC-CO2/ethanol to extract and fractionate phospholipids from tuna shavings was therefore investigated. Extraction was performed at low pressure and temperature (17.7 MPa and 33°C) to avoid oxidation of polyunsaturated fatty acids. Phospholipids were extracted and fractionated with more than 5%-ethanol in SC-CO2. To reduce the amount of consumed ethanol is an important problem to overcome in extracting on an industrial scale. The tuna shavings were soaked in the same volume of ethanol before extraction with neat SC-CO2. For performance on an industrial scale, the extracting conditions were evaluated using a 10 mL-laboratory scale reactor. 182.8 kg of soaked tuna shavings was finally extracted and 4.2 kg of DHA-PL (DHA content = 29%) was obtained in a series of industrial processes.

Journal ArticleDOI
TL;DR: Improvement of the duration and severity of PMS symptoms as a whole, as well as that of irritability, was significantly more pronounced in the GLA than in the placebo group.
Abstract: Evening primrose oil, which includes GLA, is one of the most popular of many treatments available for PMS. It has been reported that diagnosis of PMS on the basis of prospective daily rating is essential. However, few studies on alleviation by GLA of the symptoms of PMS have been performed using prospective daily rating. We examined the alleviating effect of GLA on symptoms of PMS diagnosed by prospective daily rating. Twenty-eight women diagnosed with PMS consumed vegetable oil containing about 180 mg/day of GLA for three luteal phases in a randomized, double-blind, parallel protocol, and were examined for duration and severity of PMS symptoms. Levels of DGLA in plasma phospholipid were significantly lower in women with PMS than in those without it (DGLA, P < 0.01) before treatment regardless of phase in menstrual cycle. After GLA administration, the levels of GLA and DGLA in plasma phospholipid in the GLA group were significantly higher than those both in the placebo group and before treatment. Improvement of the duration and severity of PMS symptoms as a whole, as well as that of irritability, was significantly more pronounced in the GLA than in the placebo group. These findings indicate that GLA can be effective for treating the symptoms of PMS, and that GLA and DGLA in plasma phospholipid may play a role in the onset of PMS.

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TL;DR: In this article, the micelle formation in aqueous solution of novel hybrid surfactants with phosphate head group was investigated and critical micelle concentrations (CMC) were determined as a function of temperature by surface tension measurements.
Abstract: Micelle formation in aqueous solution of novel hybrid surfactants with phosphate head group was investigated. The critical micelle concentrations (CMC) were determined as a function of temperature by surface tension measurements. The results of electrical conductivity measurements were analyzed according to the mixed electrolyte model of the micellar solution to estimate the micellar aggregation number and the degree of counter-ion binding on the micelle. Thermodynamic parameters for the micelle formation were estimated on the basis of these results. Discussion is given on the micelle formation of the present surfactant species comparing with the sulfonate-type hybrid surfactants.

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TL;DR: A series of optically active 1,4-amino alcohols were synthesized from the corresponding lactones, which were prepared from (+)-camphor and (-)-fenchone, via hydroxy amides as discussed by the authors.
Abstract: A series of optically active 1,4-aminoalcohols were synthesized from the corresponding lactones, which were prepared from (+)-camphor and (-)-fenchone, via hydroxy amides. The addition reactions of diethylzinc to aldehydes using the 1,4-aminoalcohols as chiral catalysts were investigated. 1,4-Aminoalcohol catalysts derived from (+)-camphor resulted in secondary (S)-alcohols as the major product. The 1,4-aminoalcohols bearing two propyl groups achieved the highest enantioselectivity; the enantiomeric excess was 95%. 1,4-Aminoalcohol catalysts derived from (-)-fencone resulted in secondary (R)-alcohols as the major product. In the chiral 1,4-aminoalcohols from (-)-fencone, the alcohol containing a morpholine structure appended to the amino group possessed the highest enantioselectivity; with an enantiomeric excess of 79%.