By heating a fresh soybean oil up to 180°C, two kinds of racid oils with different degrees in thermal oxidation were prepared. Then, they were administered to rats at the rate of 15% as against the basic feed. In this way, the digestive metabolic function of the dimer and secondary product in the thermally oxidized soybean oil was examined. The results obtained were as follows : In proportion to the advanced degree of thermal oxidation, the rats appeared to suffer from a deteriorated growth while their excrements and the extracted oil from their livers increased in quantity. The excrements of such rats administered with the higher-thermally oxidized oil, as compared with those given a fresh oil, were found to contain more dimer and secondary product of the fatty acid. In the livers, the dimer and secondary product were seen to exist only in a small amount in both the rats given a fresh oil and those given a thermally oxidized oil, and the result of which was almost identical, showing no difference at all in this connection. Accordingly, the dimer and secondary product in the thermally oxidized oil are believed not to be digested. As for the composition and content of the fatty acid monomer part in the excrements and liver, it was confirmed that, when the fresh oil was administered, the excrements contained less C18 : 2, C18 : 3, while the livers contained a larger quantity. In the case of thermally oxidized oil being administered, the excrements contained more and the livers less. From this fact, it was assumed that the fresh oil was more likely to be absorbed while the thermally oxidized oil was less likely.
Erucic acid (I) as starting material has been used to synthesize 1, 14-tetradecanolide in the macrocyclic lactones, which has practical value as musk like odor. Erucyl bromide (IV) was synthesized by reduction of ethyl erucinonate (II) into erucyl alcohol (III) followed by bromination. As method (a), prepared the nitrile by usual method, and nitrile was esterified by hydrogen chloride with ethanol, the resulting ethyl ester was reduced to the primary alcohol by lithium aluminium hydride, thus yielding tricosene-14-ol-1 (V). As another method (b), magnesium and formaldehyde were reacted with IV in tetrahydrofurane solution, thus prepared the V. As next reaction (a), after V was converted to bromide, and this was oxidized with potassium permanganate in acetone solution, obtaining ω-bromomyristic acid (VI). Futhermore, as another reaction (b), V was oxidized with hydrogen peroxide and formic acid, preparing triol, and the resulting triol was treated with lead tetraacetate or periodic acid, thus obtaining ω-hydroxymyristic acid. This was treated with hydrobromic acid to prepare VI. After VI was converted into the silver salt, cyclized to 1, 14-tetradecanolide (VII) in acetone solution.
The authors have developed an artificially soiled cloth, the washing behavior of which was similar to that of naturally soiled cloth, but overall behavior of the artificial soil was still insufficient to estimate detergency of alkaline builders under various conditions. Therefore, the effect of clay, which is a main component of the artificial soil prepared in our laboratory, on detergency was investigated. 1) The crystal structure of clay had much influence on detergency. The artificial soil prepared from the crystalline clay was removed more easily than the soil obtained by calcining the crystalline clay. 2) The crystalline clay adsorbed far more ABS and STPP than the amorphous clay. 3) The particle size and the moisture content of clay did not affect on detergency.
Surface active properties of the binary aqueous solutions of polyoxyethylene cetyl ether (18 mole adduct; C16-18) -alkaline or alkali earth metal soaps (5 : 1 in molar ratio) were investigated. In the emulsifying characteristics, C16-18 was found most suitable for the emulsification of kerosene, and no marked change was observed with the mixed solutions as compared to the nonionic agent except those containing barium laurate which decreased the emulsifying rate of kerosene and liquid paraffin. In the case of dispersing power, no marked change was observed with the mixed solutions for titanium dioxide, carbon black, etc.; but they showed a considerable synergistic effect on manganese dioxide. Neither C16-18 alone nor the mixed solutions showed anti-bacterial action against several yeasts and moulds. The results of the rust-preventive power study are as follows : For soft iron, owing to the preventive effect of soap, the mixtures did not rust the metal particularly in the vicinity of 0.001 : 0.0002mol/l in spite of the corrosive properties of C16-18; while in the case of aluminium, C16-18 and the mixtures did not rust it practically above 0.001 : 0.0002mol/l. The barium laurate mixtures were somewhat effective below this concentration. Although changes were very slight for brass, the mixtures were superior than C16-18 alone in general. Ultimately, the mixed solutions of laurate and ricinoleate of barium etc. were effective especially for the dispersion of manganese dioxide and the rust-prevention of soft iron and aluminium.
The properties of the fatty substances of three mushrooms (F. fomentarius, T. orientalis and A. tabescens) and their components related to the fatty acids and unsaponifiable matters were investigated. The mushrooms were dried, crushed and then extracted with ether. The oil contents of the dried matter were 2.7% (F. fomentarius), 0.6% (T. orientalis) and 5.7% (A. tabescens). The main fatty acids were C16 : 0 and C18 : 2 (F. fomentarius and T. orientalis) and C18 : 0 and C18 : 2 (A. tabescens). The Δ5, 7-sterol-contents in their unsaponifiable matters were 4.2% (F. fomentarius), 11.5% (T. orientalis) and 21.0% (A. tabescens). The main sterols seemed as Ergosterol in each, but 22, 23-dihydroergosterol was found in A. tabescens being 31% content. The non-sterol parts of the unsaponifiable matters were believed mainly consisting of long-chain alcohols in F. fomentarius and hydrocarbons in T. orientalis and A. tabescens. Moreover a carbonyl compound having mp 246°C was found in the unsaponifiable matter of T. orientalis.
The properties of the oils of Confragosa and Tricolor (Table-1), the composition of the fatty acid (Table-2) and the unsoponifiable matters were examined. These mushrooms were dried and extracted with ether. The mixed fatty acids were esterified into methyl esters with methanol and p-toluen sulfonic acid, then the fatty acid composition was examined by gaschromatography. The composition of conjugated polyenoic acid and total polyenoic acid were calculated from the UV absorption spectra with the mixed fatty acids and their isomerized derivatives (Table-3). The both unsaponifible matters were soft orange-yellow solid. The content of sterols in unsaponifiable matters was shown in (Table-4). The main sterols were purified by means of silica-gel column liquidchromatography and recrystalization, followed by analysis by gaschromatography after treatment with TMSE. The composition of sterol was ergosterol (30.1%) and 22, 23-dihydroergosterol (24.7%) for Confragosa, and ergosterol (8.2%) and 22, 23-dihydroergosterol (8.9%) for Tricolor.