The aggregation behavior of three alkylammonium perfluorocarboxylates (C_nH_2n+1NH₃⁺C_mF_2m+1COO^-; n+m=15, n=2,4,6) were investigated by rheology and polarization microscopy. The amphiphiles with n=8,10 were quite stable and hardly soluble in water and could not be studied by the method. The above three amphiphiles formed quite large molecular aggregates in diameter of up to 3μm in the solutions at lower concentration of 1.5 mmol dm^-3. At higher concentrations of 50-100 mmol dm^-3, on the other hand, the first two amphiphiles formed fine crystallites which were strongly connected to one another, resulting in high viscosity of the solutions, while the third formed stable leaflet-like crystals of larger size depending on the concentration and on the temperature. The high complex viscosity over the concentration range 20-50 mmol dm^-3 decreases with increasing the oscillating frequency applied to the solution for the first amphiphile, which results from loosening of strong connections among the crystallites due to increasing shear rate.

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In order to obtain information concerning the function of the polar group of polymeric dispersants generally used for pigment particles in a non-aqueous medium, alkylamine, alkylammonium salt, amide, and carboxylic acid were selected as the model dispersants and their adsorption behavior onto the phthalocyanine blue (PhB) pigment was studied by means of ¹H NMR spin-lattice relaxation time using a high-resolution magic angle spinning ¹H NMR probe. The amino group, particularly the primary amino group, was found to be the most effective as the adsorption site for the pigment among the functional groups examined in this study. The results obtained in this work suggest that the coordination of a lone electron pair on the nitrogen atom of an amino group to the Cu(II) of PhB is the driving force for the adsorption.

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In a hydrophilic octaethylene glycol dodecyl ether (C₁₂EO₈)-water system, a micellar cubic phase is formed below 20°C. Upon addition of decane, the maximum temperature of micellar cubic phase (I₁) is increased, and, moreover, the hexagonal liquid crystal region changes to the I₁ phase. Beyond the solubilization limit of decane in the I₁ phase, highly viscous and gel-like O/I₁-emulsions are formed in the two-phase region of I₁+O. In the case of a surfactant mixture (C₁₂EO_4.8) containing C₁₂EO₈+C₁₂EO₃, a single I₁ phase region is not present in a pseudo ternary phase diagram of water/C₁₂EO_4.8/decane system, but an I₁+O region appears in the oil-rich region. C₁₂EO_4.8 forms lamellar liquid crystal in the aqueous system but C₁₂EO₃ in the mixture is dissolved in oil and the mixing fraction of C₁₂EO₈ in the surfactant aggregate increases as oil is added. Finally, a two-phase region of I₁+O appears. It is considered that the O/I₁-emulsion or gel based on the cubic phase corresponds to the gel appeared in the so-called D-phase emulsification process. Upon addition of alkyl polyol such as glycerol or 1,3-butanediol, the transparency of the emulsion in the I₁+O region increases because the difference in refractive index between the cubic phase and excess oil is decreased. The maximum temperature of the I₁ phase decreases with increasing polyol content. Consequently, the addition of alky polyols is not crucial to form O/I₁ gels in an oil-rich region.

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A gamma linolenic acid (GLA, cis-6,9,12-Octadecatrienoic acid) producing fungus was isolated and identified for the first time as Rhizopus nigricans, labeled as SSSD-8. The alteration of carbon and nitrogen sources on the production of GLA by Rhizopus nigricans SSSD-8 was examined in flask cultures for two separate media. The cultivation conditions were optimised for GLA production by appropriate selection of carbon and nitrogen sources and their concentrations, temperature, time of incubation, and pH. On an identical weight basis, soluble starch is the best carbon source and urea the most preferred nitrogen source for GLA yield irrespective of the media composition. A maximum GLA yield of about 1640 mg/L was obtained for Rhizopus nigricans SSSD-8 when incubated at 30°C and at pH 5.5 in the medium containing 15% (w/v) potato extract, 15% (w/v) soluble starch, 0.5% (w/v) yeast extract, and 0.2% (w/v) of urea.

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Soybean-germ oil was extracted from hypocotyle enriched soybean raw material and was found to contain 4 times as much phytosterol as soybean oil. Its capacity for cholesterol diminishing effects in human was evaluated. Ninety-one healthy male volunteers, average age 44 (SD10), and serum total cholesterol (TC) below 260 mg/dl, were made to consume two eggs per day for 3 weeks. Serum TC increased in 39 subjects (≥10mg/dl) due to this consumption. Thirty of the subjects with TC above 180 mg/dl were divided into 3 groups which consumed test food with two eggs everyday for another 3 weeks. The test food was mayonnaise containing 22g cooking oil. The test groups were i) 22g Soybean-germ oil, ii) 11g Soybean-germ oil + 11g Safflower oil and iii) 22g Safflower oil. Serum TC and LDL-cholesterol (LDL-C) increased in the 22g Safflower oil per day control group. Increase in serum TC and LDL-C was noted to decrease in the 11g or 22g Soybean-germ oil per day group. Serum TC and LDL-C differed significantly in the Soybean-germ oil intake and control groups. The daily intake of Soybean-germ oil thus appears effective for lessening serum TC and LDL-C in human subjects.

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We examined the effect of tea catechins on the oxidation of dietary lipids by measuring [¹³C]-carbon dioxide in the expiration released from [1-¹³C] labeled tripalmitin. Sprague-Dawley male rats maintained with the basal diet for two weeks were fasted for 14 hr, then administered lipids containing [1-¹³C] tripalmitin (6.1%) at the dose of 0.33 g/kg body weight. After 2 hr, rats were administrated tea catechin orally at the dose of 300 mg/kg body weight. [¹³C]-Carbon dioxide in the expiration during every two hours after the administration of labeled lipid was collected up to eight hours. Saline without tea catechin was given as a control. The content of ¹³C in the carbon dioxide during 2 to 4 hr after the lipid administration increased significantly (p<0.001) in the tea catechin group as compared with the control group. Effect of the long-term administration of tea catechins was next examined by using rats that had been fed the diet containing 1% tea catechin for 2 weeks. No additional tea catechin was given. The content of ¹³C in the carbon dioxide in the 2-4 hr expiration increased significantly (p<0.001) in the tea catechin group as compared with the control group. These results clearly show that tea catechins, given as a single dose or as a long-term administration, facilitate the oxidation of dietary lipids in rats.

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Capsorubin and related compounds, capsanthin, capsanthin 3,6-epoxide and cycloviolaxanthin isolated from paprika (Capsicum annuum) inhibited the oxidation of methyl linolate in solution initiated by 2,2'-azobis(2,4-dimethyl vareronitrile) (AMVN). The antioxidative activities decreased in the order of capsorubin>capsanthin 3,6-epoxide>capsanthin>cycloviolaxanthin>β-carotene.

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When a mixture of 4-biphenylyl 4-methylbenzoate(1) and anhydrous aluminum chloride (AlCl₃) was boiled in ο-dichlorobenzene, 4-hydroxy-3-biphenylyl 4-methylphenyl ketone(4) was obtained as the main product. The corresponding ο-hydroxyketones, 4-hydroxy-3-biphenylyl 4-chlorophenyl ketone(6) and 4-hydroxy-3-biphenylyl 4-nitrophenyl ketone(8) were also obtained as the main products from 4-biphenylyl 4-chlorobenzoate(2) and 4-biphenylyl 4-nitorobenzoate(3) under the same reaction conditions, in which a small amount of the corresponding 4’-hydroxy-4-biphenylyl ketones(5) were detected. The rate of the Fries rearrangement is as follows; 1>2>3. When the amount of AlCl₃ was increased in the Fries rearrangement, the rate formation of 4’-hydroxy-4-biphenylyl phenyl ketones(5, 7, and 9) was accelerated with the decrease in the rate of the ortho-migration. On the other hand, the yield of 8 increased without formation of 9 by increasing of the amount of AlCl₃ in the Fries rearrangement of 3. Moreover, 4’-Hydroxy-4-biphenyly ketones(5, 7, and 9) were also obtained in the Fries rearrangement of 1, 2 and 3 using ο-dichlorobenzene at boiling temperature. Ortho-Fries rearrangement of 1, 2 and 3 seems to proceed mainly via an intramolecular pathway slightly accompanied by intermolecular rearrangement.

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Docosahexaenoic acid (DHA) supplemented breads were prepared, one of which containing 1g DHA and 0.3g of eicosapentaenoic acid (EPA). Twenty healthy volunteers with hyperlipidemia consumed the two breads daily for 4 weeks. Serum total cholesterol (TC) and triglyceride (TG) significantly decreased at 4 weeks following consumption (TC/before ingestion 232 and after, 222mg/dl, TG/before, 204 and after, 147mg/dl) with concomitant increase in serum DHA and EPA. This lipid of DHA supplemented bread is essentially the same as that of purified DHA capsules in the same amount. This bread could be consumed easily every day and clinically effective for lipid reduction.

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Examination was made of the effects of tea catechins on energy metabolism in 8-wk-old male Sprague-Dawley rats subsequent to 4 or 18 hr food depletion. Energy expenditure within 4 hr after a single dose of tea catechins at 100 mg/kg weight both increased significantly compared with saline administration. At 18-hr food depletion, energy expenditure by fat oxidation significantly exceeded that in the tea catechins group. A single dose of tea catechins is thus clearly shown to induce thermic response in the rats.

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