In the previous papers, the authors reported that tocopherol showed the effect to reduce the toxicity of thermally oxidized oil in rats.
The present paper deals with the biological effect of oryzanol on rats fed thermally oxidized oil.
1) The rats fed thermally oxidized oil showed growth depression, whereas better growth was observed those fed the same oil with tocopherol and/or oryzanol. The effect of oryzanol on the weight gain of rats was found less than that of tocopherol.
2) Feeding of thermally oxidized oil reduced the percentages of C_18:2 and C_20:4 in liver, kidney and testicle lipids, however, they were increased by the addition of tocopherol and/or oryzanol in the diets. These results indicated that oryzanol has some antioxidative activity for the oxidation of polyunsaturated fatty acid in tissues, but this activity was weaker than tocopherol.
3) Hemolysis rates of erythrocyte of rats fed thermally oxidized oil was much higher than those of fresh oil or the same oil with oryzanol.

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It is well known that the brown discoloration is observed by the heating of phospholipids. It has long been presumed that this brown discoloration was due to the reaction among amino group and carbonyl compounds which are formed by the heating of phospholipids. However, little knowledge has been obtained on the mechanism of the browning reaction.
in order to elucidate the reaction mechanism of browning, model experiments were carried out. Soybean lecithin was heated with water at 180°C in liquid paraffin, and brown products (BP) thus formed, were isolated by gel-permeation chromatography on Sephadex LH-20 and cellulose column chromatography. The IR absorption spectrum and elemental analysis of BP were similar to those of original lecithin. BP was hydrolyzed by phospholipase A and yielded free fatty acids. In another experiment, acidhydrolysis of BP was carried out, thereby choline and phosphoric acid were noticed in water, and brown compounds (BC) moved into chloroform. Trace amounts of nitogen were determined from BC in chloroform. After reduction of BP with sodium borohydride, colorintensity diminis hed.
From these results, the authors concluded that BP seems to be a polymer retaining the structure of original lecithin and is similar to the products formed in aldol condensation reaction rather than Maillard reaction.

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In a previous paper the authors reported that browning products (BP) which were formed in heated lecithin seemed to be compounds retaining the structure of original lecithin, but polymerized at the fatty acid parts.
The above mentioned properties of BP suggest that fatty acid constituents of original lecithin are modified in the early stage of browning reaction. The present paper deals with isolation of a major intermediate product (IP) from BP. IP was isolated from heated lecithin by silicic acid column chromatography, thus obtained IP was heated and the color of this products was compared with heated lecithin. The results indicated that brown color developed more in heated IP than in heated lecithin. After reduction of carbonyl groups in IP with sodium borohydride, the products did not produce the brown color. These results led the authors to conclude that carbonyl groups participated in browning reaction. From the results of investigation of carbonyl compounds authors found that the main carbonyl compounds were 9-oxo-10, 12-octadecadienoic acid and 13-oxo-9, 11-octadecadienoic acid which were conjugated dienone compounds.
From these results, the authors presumed that conjugated dienone compounds were formed in the early stage of browning reaction by heating of lecithin, and these carbonyl compounds were polymerized by catalytic action of choline and/or phosphoric acid which were constituents of lecithin.

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Several marine oils such as fin whale, turbot, saury pike, mackerel and cod oils were investigated in order to manufacture lower melting hydrogenated oil which will have high oxidation stability and good plastisity. Reactivity and selectivity of hydrogenation, oxidation stability of hydrogenated oil and performance of plastic fat were examined.
Experimental conditions were as follows ; catalyst : 2 wt% of Cu-Cr-Mn catalyst, temperature : 190200°C, pressure : 0.2 kg/cm², agitation speed : 600700 rpm, reaction time : 4 hours.
1. Saturated fatty acids were not almost produced, but a small amount of or a trace of trienoic and polyenoic acids was still remained when the reaction ended. Trans acid contents in hydrogenated oils were about 18% except in hydrogenated turbot oil. The contents of trans acid increased rapidly when iodine value of oil decreased to around 100.
2. The lowest melting hydrogenated oil was turbot oil, while the highest melting one was mackerel oil which contained originally the most amount of saturated fatty acids and polyenoic acids.
3. A trace of catalyst was confirmed after filtration of hydrogenated oil. Cr and Mn were not almost detected, but Cu was found below 1 ppm by atomic absorption method in the oil which was bleached with active clay after washing with phosphoric acid and alkaline water.
4. The oxidation stability of selective hydrogenated oil with Cu-Cr-Mn catalyst was inferior than with nickel catalyst.

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Three samples of sodium 2-n-alkylindole sulfonate [alkyl : heptyl (R-7 : abridged sign of this compound), undecyl (R-11), pentadecyl (R-15)] were prepared by the following process,
_??_-CH₃-NH₂ RCOCl→-HCl_??_-CH₃-NHCOR NaNH₂→-H₂O_??_-N-H-R H₂SO₄→-H₂O NaO₃S+_??_-N-H-R
and identified by elementary analysis, IR and NMR. The physico-chemical properties such as specific gravity, relative viscosity, surface tension, specific electrolytic conductivity. solubilization (dyestuff), sedimentation (CaCO₃), emulsification (liquid paraffin) and wetting efficiency (feltcloth) were measured for the aqueous solution of these surfactants.
The results obtained were as follows ;
1) R-11 decreased the surface tension of water approximately to 4045 dynes per cm.
2) R-15 was most excellent amoung many other surfactants in abilities of the solubilization of dyestuff, deflocculation of calcium carbonate and emulsification of liquid paraffin.

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Solution polymerization of acrylamide was carried out using n-dodecyl amine as a solvent and sodium methoxide or benzoyl peroxide as an initiator. The chemical structures of the obtained telomers are as follows :
by anionic telomerization (LAA series)
C₁₂H₂₅-N- (CH₂-CH₂-CONH) -m (CH₂-CH) n-H-CONH₂- (CH₂-CH₂-CONH) -m' (CH₂-CH) -n'H-CONH₂ (m+m') /P_??_ 0.8
by radical telomerization (LAR series)
C₁₁H₂₃-C-H-NH₂- (CH₂-CH) nH-CONH₂
The degree of polymerization of obtained telomers was as follows ; LAA series =4.722.0, LAR series =1.23.6.
The chemical structures of these telomers were determined by elementary analysis, IR spectrum, Rimini test and hydrolysis test [LAA series were hydrolyzed about 20% of acrylamide unit (monomeric unit) by 0.5 N-NaOH aqueous solution]. Relation between cmc and P_n of LAA series are as follows ;
log cmc=0.051 P_n-1.55
The aqueous solutions of low P_n telomers (LAA and LAR series) have low surface tension, low foamability, low dispersing power (CaCO₃), high emulsifying (benzene, gasoline) and high solubilizing power (Orange OT).

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Diethylene glycol monoterpenyl ethers (containing terpenyl group : isobornyl [11], n-bornyl [16], 1-β-fenchyl [18], α-terpinyl [23] and β-terpinyl [28]), triethylene glycol monoterpenyl ethers (containing terpenyl group : isobornyl [12], n-bornyl [17] 1-β-fenchyl [19] and α-terpinyl [24]) and polyethylene glycol monoterpenyl ethers (containing terpenyl group : isobornyl [13], [14], [15], 1-β- fenchyl [20], [21], [22] and α-terpinyl [25], [26], [27]) were prepared by the reaction of various terpene hydrocarbons such ascamphene [1], tricyclene [2], 2-pinene [3], 2 (10) -pinene [4] and 1, 8-p-menthadiene [5] with diethylene glycol [6], triethylene glycol [7] and polyethylene glycol (MW=200 [8], 400 [9], 600 [10]) in the presence of cation exchange resin at 50°+2°C. These structures were confirmed by physical constants, IR and NMR. Surface activities such as surface tention, foaming property, penetrating power solubilizing power and emulsifying power of these nonionic surfactants were investigated.
As a result, triethylene glycol monoisobornyl ether [12], di-and triethylene glycol mono-α-terpinyl ether [23] and [24] had far better penetrating power than LAS (sodium linear alkyl benzene sulfonate). Polyethylene glycol monoisobornyl ether [13] [15] and polyethylene glycol mono-α-terpinyl ether [25] [27] had far lower foaming property than LAS. And also, [14], [26] had far better penetrating power and solubilizing power than LAS.

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Four kinds of quaternary ammonium compounds were prepared from triethanolamine isobornyl maleate and terpenyl bromides obtained by bromination of terpenealcohols such as isoborneol, geraniol, citronellol, dihydrocitronellol with hydrobromic acid. The triethanolamine isobornyl maleate was prepared from triethanolamine and isobornyl maleic acid half ester obtained by hydrolysis of alkyl isobornyl maleates with dil. alkali aqua. solution.
Antimicrobial activities of these quaternary ammonium compounds were investigated.

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High resolution ¹³C-NMR spectra of maleic anhydride adduct to methyl trans-9, trans-11-octadecadienoate (mp 72.473.2) were obtained by Fourier transform techniques. From the analyses of the spectra, the maleic anhydride adduct was affirmed to be methyl 8- (2, 3-dicarboxylic cyclic anhydride-4-hexyl-5-cyclohexene-1-yl) octanoate. Furthermore, the ¹³C chemical shifts of the adduct was obtained by the assignment of the signals and the ¹³C-H spin-spin coupling constants were also determined from the proton coupling spectrum.

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