Four groups of weanling male rats were fed diets containing 20% (by weight) either palm stearin, soybean oil, their equal weight blend (PS/SO) or fat randomized blend [(E)PS/SO] for 28d. A comparative study was made of serum lipids, cholesterol and its metabolites in the livers and feces of the rats. The physical and chemical properties of the dietary fats were also examined.
1) SFC curves indicated palm stearin rich in saturated triglycerides, mainly tripalmitin, to be considerably hard even at 30°C. However, its blend with soybean oil and further randomization improved plasticity and mouth feel due to decrease in SFC at each step.
2) Serum cholesterol (total) and triglyceride concentrations were significantly higher in the palm stearin group, but similar in the PS/SO and (E)PS/SO groups, compared with those in the soybeanoil group. In the palm stearin, PS/SO and (E)PS/SO groups, C_{16 : 0} rich in dietary fats was preferentially excreted into feces, but the proportion of this fatty acid in liver lipids of the palm stearin group was obviously higher than those of the PS/SO and (E)PS/SO groups.
3) Contents of cholesterol and its metabolites in the feces were basically the same among the palm stearin, PS/SO and (E)PS/SO groups. In contrast, contents of some metabolites, formed by the action of intestinal bacteria, such as coprostanol and deoxycholic acid, in the palm stearin group werelower than those of the other two groups. Thus, the ratio of metabolites to cholesterol in the feces was low only in the palm stearin group, while no differences could be detected among the PS/SO, (E)PS/SO and soybean oil groups.
4) Plam stearin, uniquely rich in C_{16 : 0,} especially in tripalmitin, thus appears to have adverse effect on serum cholesterol, probably due to increase in C_{16 : 0} incorporated into liver, and cholesterol metabolism due to the suppression of intestinal bacteria functions. However, blending palm stearin with liquid vegetable oils and randomization were shown to improve both physical and biological properties.

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Inclusion complexes of α-, β-, and γ-cyclodextrins with tetralin, methyl oleate, methyl linoleate, and methyl linolenate were prepared, and their molar ratios of cyclodextrins to substrates of the inclusion complexes were determined. The affinity of cyclodextrins to the hydroperoxides of the substrates is discussed. Small amounts of aqueous cyclodextrin solutions were added to autoxidized substrates with stirring to obtain the inclusion complexes. POV of the remaining substrates was found to be less than that of the initial POV. This indicates the cyclodextrins to encase hydroperoxides preferentially from autoxidized substrates. To lessen the POV of tetralin, treatment with β-, or γ-cyclodextrins was much more effective than α-cyclodextrin. The most noticeable effect was obtained on using β-cyclodextrin as the host. γ-cyclodextrin was the most potent for lowering the POV of methyl oleate and methyllinolenate, and α-cyclodextrin for methyl linoleate.

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The ene-type chlorination of terpenyl alcohols such as linalool (1 a), geraniol (1 b), nerol (1 c) and citronellol (1 d) with hypochlorous acid gave allylic chlorides (2 a-d) in good yields.
These compounds (2 a-d) reacted with prenylmagnesium chloride in the presence of Cu (I) salt to give S_N 2' type cross coupling products (4 a-d) and (5 a-d) including nerolidol and farnesol, with high regioselectivity as shown in Table-2. Prenyl isopulegol (6) was prepared the by ene-type chlorination of isopulegol (1 e), followed by cross coupling reaction of the resulting product with prenylmagnesium chloride, as shown in Fig.-2.

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The effects of polyhydric alcohols on the viscosity, electric conductivity and phase transition temperature of a octadecyl-trimethylammonium chloride (OTAC)/1-hexadecanol (C₁₆OH)/water system were studied. Propylene glycol had significant effect on the physical properties of this ternary system, while glycerol did not. Following the addition of propylene glycol to the system having a low molar ratio (1.0) of C₁₆OH to OTAC, viscosity decreased considerably accompanied by the disappearance of the rapid rise in electric conductivity at about 43°C. An endothermic peak at about 43°C also disappeared. Association of OTAC, C₁₆OH and water would thus appear to be altered as a result of adding propylene glycol, this being likely due to the amphiphilic feature of the system.

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Monolayer properties and ion-transportation phonomena of amphiphilic crown ethers with various hydrocarbon chains were examined using a special Langmuir trough designed to measure simultaneously the transported amount of ions through an oil phase including various carries and interfacial tension at the oil/water interface.
Under a polar oily condition, the transportation rate of Ba²⁺ was determined mainly by the distribution of a compound between the oil and water phases. In the system including a non-polar oil, the adsorbed monolayer of a crown ether compound formed at the interface was an essential factor determining ion transportation rate. The stability of the adsorbed layer was influenced by the polarity of the oil phase and structure of amphiphile compound; that is, the more lipophilic the crown ether compound, the faster was the transportation rate due to considerable solubility in the oil phase. The crown ether compound with two long hydrocarbon chains (2 C₁₂) was extremely lipophilic, transported metal ions quite well, and could maintain a high transportation rate for a long period. However, the crown ether compound with amino acid residues and 2 C₁₂ showed zero-transportation capacity.

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The formation and solubilization of copper (II) complex in aqueous solution of N-decyl-β-alanine (NDeA) were investigated. When NDeA was dissolved in aqueous copper (II) chloride solution (2 mM), blue fine crystals of NDeA-copper (II) complex, [Cu(NDeA)₂(H₂O)₂], precipitated. Below cmc (13 mM) of NDeA, the amount of precipitate increased with the concentration of NDeA. At the concentration above cmc, the amount of precipitate decreased because the precipitated complex was self-solubilized in the NDeA micelle. The visible spectra (absorption maximum, λ_max=630 nm) of the solubilized copper (II) complex of NDeA were almost the same as the visible diffuse reflection spectra of the complex in the crystalline state. The environment in the vicinity of the coordination sphere of the solubilized complex would thus appear to be similar to that of the crystalline complex. For the NDeA micellar solution solubilizing the copper (II) complex of NDeA, a multibilayer structure with a long spacing of 3.56 nm was observed by dynamic light scattering and low angle X-ray diffraction measurements. A solubilization model is proposed in which extended complex molecules of the trans form are incorporated between bilayers in the lamellar micelle of NDeA.

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The solubilization behavior of complexes composed of sodium alkyl sulfate and water soluble polymer, hydroxypropylcellulose (HPC), was studied. Two kinds of oil-soluble dyes, were used as solubilizates.
The solubility of the dye increased with the concentration of HPC. The weight-average molecular weight (M_w) of HPC showed little effect on dye solubilization in either case. Solubilizing capacity (S_p) increased with chain length of the hydrocarbons of sodium alkyl sulfates. The break point (C_b) showed a tendency opposite to that of S_p. S_p decreased in the order, Oil Yellow OB>Oil Orange SS regardless of the presence of HPC and increased with temperature. The absorption spectra of oil-soluble dyes in n-dodecane, in aqueous solutions of HPC and in sodium alkyl sulfate-HPC-sodium sulfate solution indicated that Oil Yellow OB to possibly be solubilized mainly in the HPC region of sodium alkyl sulfate-HPC complexes, while Oil Orange SS is to be solubilized in the hydrocarbon region of the complexes.

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The hydration of iso-longifolene (1), thujopsene (2) and α-cedrene (3) with water in the presence of several synthetic zeolites was studied.
The following results were obtained.
The hydration of (1) with water in the presence of each synthetic zeolites afforded predominantly 2, 2, 7, 7-tetramethyl tricyclo [6.2.1.0^{1, 6}] undeca-5-en-4-on (4). With water in the presence of 2020 AH, widdrol (8) was obtained as the principal component from (2). With each synthetic zeolite, 2-cedranone (11) and 2-isocedranone (12) were obtained from (3) as the main products at more than 85 % of the hydration products.

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A study was made of the decomposition reactions of (-) -isolongifolene oxide (1), (-) -thu-jopsene oxide (2), and (-) -α-cedrene oxide (3) with formic acid or chlorinated acetic acids, in the presence of synthetic zeolites.
In the reactions of (1), two components were formed at all conditions ; conversion exceeded 90 % irrespective of the type of zeolite used, and in reactions with trichloroacetic acid in 1, 2-dichloroethane using ferrierite type zeolite, (5) was obtained almost quantitatively.
The reactions of (2) yielded four kinds of products, the principal component of which was methyl 6, 10, 10-trimethyl-tricyclo [4.4.0.0^{1, 3}] dec-4-yl ketone (8). Considerable difference in composition was observed depending on the type of acid used. The reactions of (3) also gave the best results under conditions the same as for (1) with quantitative conversion. (-) -2-Cedranone (10) at a composition ratio over 90 %, at 2025°C was obtained.

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Two coumarin derivatives were isolated from hassaku (Citrus hassaku HORT.), zabon (Citrus gradis OSBECK.) and amanatsu (Citrus natsudaidai) peeling. Their structures were determined by means of MS, ¹H-NMR and ¹³C-NMR spectroscopy.
8- (2, 3-dihydroxy-3-methylbutyl) -7-methoxycoumarin (1) and 7- [(6, 7-dihydroxy-3, 7-dimethy1-2 E-octenyl) oxy] coumarin (2) were found.
Compound (1) was intravenously injected into SHR-SP rats (1 mg/100 g body weight) with subsequent rise in blood pressure. Compound (2) was not tested owing to its poor solubility in water.

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Changes in the sterollipids and sphingolipids of Adzuki bean (Vigna angularis) seeds during maturation were examined. Major component sterols in sterollipids, acylsterol (AS), free sterol (FS), sterylglycoside (SG) and acylsterylglycoside (ASG) were usually sitosterol and stigmasterol, the latter being minor in AS. Although the sterol composition of AS was roughly constant during maturation, this parameter for FS, SG and ASG showed remarkable change; the proportion of stigmasterol increased while that of sitosterol decreased. Associated fatty acid and sphingoid compositions of ceramide differed remarkably from those of cerebroside at any stage of seed development. The major ceramide species of cerebroside could usually be identified by reversed-phase HPLC as N-2-hydroxypalmitoyl-trans-4, trans-8-sphingadienine during maturation.

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A description is given of the development by collaborative study of a standardized method for the determination of polymerized triglycerides in oils and fats by gel permeation HPLC. This rapid procedure allows the determination of polymer contents equal to or higher than 3 per cent (w/w) of the total amounts of fats.

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