A convenient synthesis of cis-12-nonadecen-9-one (4a), cis-13-icosen-10-one (4b), the pheromone of peach fruit moth, and cis-5-undecen-2-one (4c), the principal volatile component of the pedal glant exudate of the bontebok is described. (4a) was synthesized starting from 1-nitrononance (1a) and acrolein via three steps. The synthetic route is shown in Scheme-1.
(4b) was easily prepared starting from 1-nitrodecane (1b) in good yield.
Similarly, (4c) could be obtained by the Michael reaction of nitroethane (1c) with acrolein.

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Following the same procedure described in the previous report Yukagaku, 34, 48 (1985), the fry test was conducted so as to compare the efficiency of tocopherol (Toc) with those of other several antioxidants and investigate the synergistic effects of antioxidants along with those of Toc on the oxidation of fried foods. This test was also carried out on L-ascorbyl stearate (AS), lecithin and sucrose fatty acid esters (SE).
1) In the case of potato chips fried in a lard system containing only one of the antioxidants at a time, the time required to attain POV 30 of the chip lipid fraction and for odor to be perceivable during storage at 60°C was in the order of a mixture of d-Tocs (m-Toc) =t-butyl hydroquinone (TBHQ) >propyl gallate (PG) >dibutyl hydroxytoluene (BHT). This order agreed with the results from the transference ratio of each antioxidant to the potato chips (=proportion of antioxidant content in the chip lipid fraction to that added to the lard system).
2) Synergistic effects on the oxidation of potato chips come about as a result of TBHQ treatment or that of PG with m-Toc. However, the effects resulting from treatment with BHT with m-Toc were the equivalent of the combined effects of all the components. However, treatment with isopropyl citrate and m-Toc together was almost the same as that resulting from m-Tocalone.
3) All tested synergists were found to cause m-Toc to have greater effect on the potato chips. The time required to attain POV 30 during storage at 60°C of lecithin>AS>SE. However, addition of lecithin or SE to the fry fat resulted in browning of the potato chips and bubbling of the fat.

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Preparation was made of the following oligomers : poly (sodium vinyloxyacetate) PVOA, poly [(sodium acrylate) -co- (sodium vinyloxyacetate)] P (A-VOA), poly [(sodium acrylate) -co- (sodium allyloxyacetate)] P (A-AOA), poly [(sodium acrylate) -co- (disodium allyloxymalonate)] P (A-AOM), poly [(sodium vinyloxyacetate) -co- (disodium maleate)] P (VOA-Ma), poly [(sodium allyloxyacetate) -co- (disodium maleate)] P (AOA-Ma), poly [(disodium allyloxymalonate) -co- (disodium maleate)] P (AOM-Ma), poly [(sodium N-allylaminoacetate) -co- (disodium maleate)] P (AG-Ma) and poly [(sodium N-allyl-3-aminopropionate) -co- (disodium maleate)] P (AAP-Ma).
Their sequestration capacity toward Ca (II), Cu (II), Cd (II), Ag (I) and Hg (II), the dispersion capacity toward MnO₂ and all their biodegradabilities were determined and compared in these respects with sodium tripolyphosphate (STPP), disodium 3-oxapentanedioate (ODA), poly (sodium acrylate) PA, poly (sodium methacrylate) PMA and poly (disodium fumarate) PF. Their building performance in detergents was also examined.
The polycarboxylate oligomers, except the amino acid type oligomers P (AG-Ma), and P (AA-Ma), showed better sequestration capacity. PF and P (AOM-Ma) showed excellent sequestration capacity. This capacity toward Ca (II) ions was superior to that toward either EDTA or NTA. Sequestration capacity was apparently better when the carboxylate content in the oligomers was large. PVOA, regarded as a carboxymethylation product of polyvinyl alcohol, tended to undergo biodegradation under aerobic conditions. Copolymerization with vinyloxyacetate (VOA) caused their biodegradability to occur more easily than that of the corresponding homopolymers. The oligomers tested in this report showed better detergency building performance than that of ODA, and some were superior to STPP in this respect.

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Sesquiterpene hydrocarbons from the seed oil of Iris tectorum M. were investigated. Fractionation of the hexane extract of the seeds by column chromatography on activated alumina and steam distillation gave monoterpene-free hydrocarbons which showed approximately thirty peaks by capillary gas chromatography. A combination of techniques including a silver nitrate addition procedure, rectification and silver nitrate-impregnated silica gel column chromatography was used to separate the sesquiterpenes.
Twenty-four compounds could be identified on the basis of spectral data (IR, NMR, GC, GC-MS) and chemical transformations. The main components were germacrene D (45%), alloaromadendrene (12%), δ-, γ-cadinene (13%), and β-caryophyllene (7%). These sesquiterpenes in Iridaceae plants were characterized for the first time in the present research.

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The dissolution rates of cholesterol monohydrate as a model of cholesterol gallstone in typical liquid terpenes (ketone, alcohol and ester derivatives) were measured at 37°C by the static disk method. All the terpenes were found to be excellent dissolution agents for cholesterol monohydrate whose dissolution rate was found to depend the number of isoprene residues in the terpene molecules and the rates of terpenes with the same number of isoprene residues decreased in the order of ketone, ester and alcohol.
One of the terpenes was injected directly into the gallbladders of controll mice and found to be an effective dissolution agent for cholesterol gallstones.

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The authors synthesized polyethylenepolyamine base multi-branched high molecular weight nonionic surface active agents and studied their physicochemical properties so as to evaluate their effects for improving the fluidity of coal-water slurry (CWS). The following results were obtained.
1) A surface active agent prepared by the addition of propylene oxide (PO) and ethylene oxide (EO) to polyethylenepolyamine (PEPA) improved the fluidity of CWS.
2) Surface active agents prepared by adding only EO to PEPA brought about less improvement than the above mentioned agent.
3) The effects of the agents depended on the molecular weight of polyoxyalkylene side chain and improvement was best at a molecular weight of 5, 000 or more.
4) Using a small amount of the above agent, Tatung coal CWS with low viscosity and high coal concentration was made.

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Rice bran foots, a by-product in the purification process of rice bran oil was hydrolyzed without stirring at 30°C by lipase drived from Candida cylindracea. The optimum pH range was 57. The degree of the enzymatic hydrolysis reached to more than 88% at the amount of 20U/g-foots at pH 6.8 for 6h. The hydrolysis was also performed with stirring in the presence of some non-polar organic solvents such as hexane, heptane, and isooctane.

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The concentration of bromide ion was measured by an ion electrode method and a titration for the stirred and sonicated aqueous solution of didodecyl-, ditetradecyl-, and dihexadecyl-dimethylammonium bromides. The observed bromide concentration, combined with the surface tension and the molar conductivity, was correlated to the forms of the aggregates in the solution. And the stability of the aggregates was also estimated.

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