The cause of mass poisoning by dried salted fish was followed in continuation of the previous reports. Paper chromatography revealed the presence of histamine, tyramine, agmatine, arcaine, methylguanidine, phosphorylcholine, choline, and trimethylamine (cf. Fig. 1). Adsorption chromatography through alumina suggested the fraction working synergistically with histamine included agmatine, arcaine, methylguanidine, and phosphorylcholine (cf. Fig. 2). Lethal dose-sigmoid curve for mice was prepared and the synergistic action of these amines with histamine at lethal toxicity was confirmed (cf. Fig. 4, Table I). From these results, the principal cause of this mass poisoning was concluded to be histamine with synergistic action of agmatine, arcaine, and methylguanidine present.

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Reaction of N-chloroacetylaniline with phenyl- and diphenylthiourea, in ethanol, results in the liberation of aniline and hydrogen chloride to respectively form 2-phenylimino-4-thiazolidone (I) and 2-phenylimino-3-phenyl-4-thiazolidone (II). Condensation of N-chloroacetyl-p-nitroaniline and diphenylthiourea also yields (II) by the liberation of p-nitroaniline and hydrogen chloride. Therefore, the aniline liberated in the first reaction must have been from N-chloroacetylaniline. By a similar reaction mechanism, condensation of N-chloroacetylaniline with thiosemicarbazide and phenylthiosemicarbazide respectively yielded bis (4-oxothiazolidylidene-(2) )-hydrazine (IV) and 2-phenylhydrazono-4-thiazolidone (V). It was assumed that (IV) was formed by the condensation of 2 moles of 2-hydrazono-4-thiazolidone (III) formed as an intermediate of this reaction.

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As one of the new and simple synthetic procedures for 2-alkylidene- or arylidenehydrazono-4-thiazolidone derivatives, condensation of α, β-dichlorovinyl alkyl ethers with thiosemicarbazone of acetone, acetophenone, salicylaldehyde, and benzaldehyde was carried out and 2-isopropylidene-, 2-methylbenzylidene-, and 2-salicylidene-hydrazono-4-thiazolidone and 2-benzylidenehydrazono-5-benzylidene-4-thiazolidone were respectively formed. The formation of the last named compound was assumed from experimental results to have been the secondary decomposition of initially formed 2-benzylidenehydrazono-4-thiazolidone to benzaldehyde which reacted with the non-decomposed initial substance to form such a compound.

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Condensation of N-chloroacetylaniline with various monosubstituted derivatives of thiourea and thiosemicarbazide results in the formation of 2-substituted hydrazono (or imino)-4-thiazolidone derivatives with liberation of aniline. The same reaction with thiosemicarbazide substituted in the 1- and 4-positions yields 2-substituted hydrazono-3-substituted 4-thiazolidones. The similar reaction with thiosemicarbazones or arylthiosemicarbazones of acetone and aldehydes yields 2-alkylidene (or arylidene) hydrazono-4-thiazolidones or 2-alkylidene (or arylidene) hydrazono-3-aryl-4-thiazolidones. The use of such aniline derivatives is a novel and characteristic method for the preparation of 2-hydrazono (or imino)-4-thiazolidone derivatives and is especially an improved method for the preparation of 3-substituted derivatives.

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1) Thirteen kinds of styryl dyes were obtained by the respective condensation of the alkyl iodides of pyridines and quinolines possessing active methyl or ethyl group, and 2-methyl-6-chlorobenzothiazole, with aromatic aldehydes and furfurol, in the presence of piperidine. Seven kinds of quaternary salts with an organic acid residue bonded to the nitrogen in the hetero-ring were obtained by the application of the sodium or silver salt of organic acid to the styryl dyes obtained.
2) Five kinds of dyes containing a divinyl group were obtained by the application of cinnamic aldehyde derivatives to the alkyl halides of 6-chloro (or dimethylamino)-quinaldine and 6-chlorobenzothiazole.
3) An aminovinyl compound was obtained by the fusion of 6-dimethylaminoquinaldine ethiodide and p, p′-di (ethylcarbonyloxy) diphenylformamidine.
4) By the respective application of bromopropene and pentadiene dianils to 6-dimethylaminoquinaldine methiodide, 2-γ-bromo-δ-acetanilino-α, γ-butadienyl- and 2-ω-acetanilino-α, γ, ε-hexatrienylquinoline derivatives were obtained. The -N(Ac)-C₆H₅ group in the latter compounds could be substituted with -N(C₂H₅)₂ or -NH(CH₂)₂C₆H₅.
5) Two kinds of monomethine cyanines were prepared from 2-methylthiobenzothiazole methiodide.

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1) A series of ketomethine-type dyes were prepared by the application of aromatic aldehydes to pyrido [1, 2:3′, 2′] imidazolone-(5′) derivatives.
2) A series of merocyanine dyes were prepared by the application of compounds possessing an active methylene group to each of 2-methyl-6-chlorobenzothiazole, 6-dimethylaminoquinaldine and quaternary salts of its derivatives, and α-1-phenyl-3-methyl-5-hydroxypyrazole (4)-α, γ-pentadiene-ε-2′, 4′-dinitroanil.

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A pure digitonin was isolated from the seeds of domestic Digitalis purpurea L. For the purification of digitonin, especially the removal of gitonin, fractional crystallization from ether-saturated aqueous solution, followed by recrystallization from hydrated ethanol were repeated. It has been found that paper chromatography could be utilized for the purity test of digitonin and this was also used for the purification of digitonin.

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Attempt to prepare 7, 8-phenylenedioxyquinoline (II) by the Ullmann reaction of o-dibromobenzene and quinoline-7, 8-diol failed but (II) was obtained by the same reaction of o-bromophenol and 7-hydroxy-8-bromoquinoline, obtained by the bromination of 7-hydroxyquinoline.

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The benzoin condensation of 2-formylbenzoselenazole yields benzoselenazoin as red crystals of m.p. 274-275° (decomp.) which reacts with enediol reagent and forms a diacetate. Air oxidation of benzoselenazoin carried out in xylene yields benzoselenazil (I), m.p. 224-225°, which forms a hydrazone and a quinoxaline compound. Oxidation of benzoselenazoin in ethanolic potash solution yields benzoselenazolyl-2-carboxylic acid. Ultraviolet absorption spectrum of benzoselenazoin shows maximum absorption at 417 and 440mμ, and the shape of this absorption curve in this range is similar to those of benzothiazoin and quinaldoin. From the examination of foregoing chemical and physical properties, the structural formula shown by (II) is proposed for this benzoselenazoin.

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It had previously been shown, that the nitration of lepidine 1-oxide occurred int he 8-position by converting the nitration product to 8-aminolepidine. In the present series of experiments, further evidence of the above fact was provided by converting the nitration product to nitrolepidine with phosphorous trichloride, and confirmed by admixture with the known 8-nitrolepidine and by comparison of their ultraviolet absorption spectra. This substance was further derived to 8-nitroquinoline, also confirmed by admixture and comparison of the ultraviolet absorption spectra.

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Hey and Adams reported that the nitration of 2-chlorolepidine yielded a product of m.p. 142-143°, which they assumed to be 5-nitro-2-chlorolepidine, together with two substances of m.p. 213-214° and 133-135°. In Part III of this series, it was shown that the nitration product of m.p. 142-143° was 8-nitro-2-chlorolepidine. In order to solve this discrepancy, the procedures employed by Hey and Adams were followed and as a result of chromatographic separation, ultraviolet and infrared spectral analyses, and thermal analysis, the product of m.p. 142-143° was established as the 8-nitro compound. The product of m.p. 133-135° was found to be a mixture of 6- and 8-nitro compounds from which, by the Wolff-Kishner reduction with CuSO₄ instead KOH, only 8-aminolepidine was obtained. Nitration of lepidine yields 8-nitrolepidine and a product of m.p. 127-129, which is assumed to be 5-nitrolepidine from its ultraviolet absorption spectrum.

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Carpesia lactone, C₁₅H₂₀O₃, absorbs 1 mole of hydrogen on catalytic reduction with platinum oxide and the dihydro compound so obtained forms a 2, 4-dinitrophenylhydrazone, from which it is seen that carpesia lactone contains 1 each of keto and lactone group, and 1 double bond. The lactone grouping is extremely stable to alkalis and γ-lactone is indicated even from its infrared absorption spectrum. Ozonolysis of the lactone does not form a volatile substance and since the lactone shows the reaction for methyl ketone and forms acetic acid on permanganate oxidation, it was assumed to possess a partial structure of CH₃CR₁=CR₂R₃. The infrared absorption spectrum revealed the double bond characteristic absorption for -CH=CR- and the conjugation of the double bond with the keto grouping was anticipated from molecular refraction and ultraviolet absorption spectrum that the structure shown in Fig. 5 is proposed for carpesia lactone.

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In order to elucidate the antibacterial mechanism of the tricarbonylmethane-type structure, several number of acyl groups were introduced into the 3-position of triacetic acid lactone, by reacting an acid chloride with conc. sulfuric acid as a catalyst. 3-Acyl-6-methyl-1, 2-pyran-2, 4 (3)-dione with the acyl radical of saturated fatty acids such as C₂H₅CO-, and C₆H₅CH₂CO-, C₆H₅CH₂CH₂CO-, C₆H₅CH=CHCO-, and CH₃(CH=CH)₂CO- in the 3-position were prepared. Of the compounds formed, 3-cinnamoyl compound, m.p. 131-132°, does not agree with the substance of m.p. 105-106° reported to have been obtained by Hale on the condensation of dehydroacetic acid and benzaldehyde. The attempts to obtain this substance by following the method of Hale failed and the substance agreeing with it was not obtained by the reaction with cinnamoyl chloride. It seems likely from analytical values and other properties that the substance of m.p. 131-132° obtained in the present experiments is the one with the correct structure.

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Comparative examination was carried out on the antibacterial power of the tricarbonylmethane-type compounds, such as 3-acyl-6-methyl-1, 2-pyran-2, 4(3)-dione, and the γ-pyrone derivatives. It was thereby found that the compounds possessing a tricarbonylmethane-type structure in their molecule showed both antifungal and antibacterial properties. As for the acyl side-chain, those with lower, saturated acyl groups were found to show better antifungal properties while those with higher acyl group (C₉H₁₉CO-, etc.) or benzene-substituted acyl groups showed strong antibacterial power. It was also found that the tricarbonylmethane-type compounds possessed the growth inhibition of Staphylococcus aureus by extending the lag phase of growth. From experiments on the addition of cysteine and thioglycolic acid, there seemed to be no inhibition of the thiol group. These facts indicate that the antibacterial action of dehydroacetic acid homologs is not the inhibition of respiratory metabolism but obstruction of the formation of enzyme system.

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The sequence of following reactions was studied: L(+)-ψ-ephedrine→L(+)-N-acetyl-ψ-ephedrine→L-N-acetyl-ψ-ephedrine chlorosulfinate→L(-)-ephedrine hydrochlorid and L(-)-ephedrine→L(+)-N-acetylephedrine→L-N-acetylephedrine chlorosulfinate→L(+)-ψ-ephedrine hydrochloride. By these steps L(+)-ψ-ephedrine was converted to L(-)-ephedrine hydrochlorid, the yield of which was 70-75% of the theoretical amount based on N-acetyl-ψ-ephedrine.

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Quaternary salt of dl-threo-1-p-dimethylaminophenyl-2-dichloroacetamido-1, 3-propanediol, a chloramphenicol whose nitro group had been substituted with a quaternary ammonium salt, was prepared starting with p-dimethylaminoacetophenone. These quaternary ammonium salts failed to show any antibacterial action against typhoid bacilli.

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Anthelmintic tests in vitro and in vivo were carried out on numerous anilides and naphthalides of 5-nitro-2-furanacrylic acid using mouse string worm, Syphacia obvelata and Aspiculuris tetraptera, and following results were obtained.
1) Even in a small dose, the action of 2-(5-nitro)-furanacryl-p-chloroanilide (F 2022) in removing string worm is reliable, while benzyl phenylcarbamate hexylresorcinol, and santonin are ineffective in this case.
2) F 2022 does not show anthelmintic action in vitro.
3) The toxicity of F 2022 is only about 1/50 of Furacin.
4) F 2022 is very effective for human Ancylostoma duodenale, Trichocephalus trichiuru complete expelling of the worm being effected by an oral administration of a small dose without any sideeffects.
5) F 2022 is a stable compound and comes as yellow needles, m.p. 214°, sparingly soluble in water.

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The usual method of preparing the amide or anilide of 2-(5-nitro)-furanacrylic acid is to derive the acid to acid chloride with thionyl chloride and reacted with amine or aniline. However, the yield and purity of the acid chloride in such a case were not good that 2-(5-nitro)-furanacrylic acid, m.p. 235° (decomp.), was warmed with acetic anhydride and derived to 2-(5-nitro)-furanacrylic acetic anhydride, m.p. 126°, which was derived to the chloride in a good yield by warming with thionyl chloride. Considerations were made on this reaction mechanism.

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Electrophoresis, ultraviolet absorption spectral measurements, and polarography were carried out on crude parotin (EB-1), and the precipitates obtained during purification process by ammonium sulfate fractionation (cf. Fig. 1) at 25% (NH₄)₂SO₄ (EB-2), 20% (NH₄)₂SO₄ (EB-3), and 15% (NH₄)₂SO₄ (EB-4), and following results were obtained.
1) Electrophoresis showed that the order of purity was EB-1, EB-2 (EB-3), and EB-4, the last being the purest.
2) All the products of various purity show the maximum absorption at 277±0.5mμ in an aqueous solution of pH 7.0 (Fig. 2). The value of extinction, E_1cm^1% at this wave length, becomes larger in the order of EB-1, EB-2 (=EB-3), and EB-4 (cf. Fig. 2) and shows a linear relationship with the concentration of parotin in a definite range of concentrations (cf. Fig. 3).
3) All the products of various purity show three-step wave in their polarogram, in ammonium chloride-ammonia buffer solution, in the presence of bivalent or trivalent cobalt salts (cf. Fig. 4 and Table II). The 1st wave agrees with the potential of cobalt ion precipitation, the 2nd wave with the specific protein wave of parotin protein, and the 3rd wave with cystine in the parotin molecule (cf. Tables III and IV). The wave height of the 2nd wave increased in the order of ED-1, ED-2 (=ED-3), and ED-4 (cf. Fig. 5) and the wave height is in linear relationship with the concentration of parotin within a definite range of concentrations (cf. Fig. 5).

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In order to elucidate the structure of the flavone obtained by the degradation of ginkgetin, 8-(β-anisoylethyl)-5, 7, 4′-trihydroxyflavone methyl ethers were prepared by the following two processes:
1) Condensation of 8-chloromethylacacetin-7 methyl ether (IV) and ethyl anisoyl-acetate (V), in the presence of sodium ethoxide, followed by saponification and decarboxylation, gave 8-(β-anisoylethyl)-5-hydroxy-7, 4′-dimethoxyflavone (VIII), m.p. 198°, in a good yield, and its methylation gave the methyl ether (IX), m.p. 152°, whose properties were vastly different from those of the corresponding methyl ethers derived from the flavone from ginkgetin.
2) 8-(β-carbaminoethyl) compound (XVI) was prepared from 1-(β-carboxyethyl) 2-hydroxy-4, 6-dimethoxybenzene (X) by acetylation, methylation, anisoylation, rearrangement, and cyclization. Further saponification of (XVI) and polyphosphoric acid condensation with anisole yielded (IX). The yield of the last process was very poor.

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Kainic acid, C₁₀H₁₅O₄N⋅H₂O, the anthelmintic principle, was extracted from Digenea simplex Ag., in 0.02-0.06% yield. Kainic acid is soluble in water, forming an acid solution, and is sparingly soluble or insoluble in ethanol, acetone, ether, and benzene. Molecular weight, 213; pK′, 2.16, 4.57, 10.42; [α]_D²⁵: -12.7°. It gives positive reaction for secondary amine, colors yellow with ninhydrin, and this yellow substance possesses the absorption maximum at 429mμ. The dry distillation of kainic acid resulted in evolution of carbon dioxide, formation of a pyrrole-like substance giving positive pine splinter and Ehrlich reactions, and needle crystals of m.p. 140°, corresponding to the formula C₁₆H₁₈O₂N₂. Kainic acid possesses one double bond and forms dihydrokainic acid, m.p. 285° (decomp.), C₁₀H₁₇O₄N, [α]_D²⁵: -37°. Acetylation of kainic acid with acetic anhydride gives N-acetylkainic anhydride, C₁₂H₁₅O₄N, and the same with dihydrokainic acid gives N-acetyldihydrokainic anhydride, C₁₂H₁₇O₄N. Esterification of kainic and dihydrokainic acid respectively yields the dimethyl ester of b.p₃ 133° and b.p₃ 140°. Kainic acid does not show a marked absorption in the ultraviolet region but the absorptions of -NH, -COOH, and -COO- appear in the infrared region. From the foregoing results, a structure of unsaturated imido acid of (C₈H₁₂) (COOH)₂⋅NH⋅H₂O with one double bond has been proposed.

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Assuming that kainic acid possesses a five-membered ring containing nitrogen, the Emde degradation of kainic acid and dimethyl kainate was carried out but the degradation was not effected. The Hofmann degradation of dimethyl dihydrokainate failed to cause the ring opening. Dry distillation of kainic acid with soda-lime yielded a pyrrole-like oil at b.p₂₅ 67°, C₈H₁₃N, giving positive pine splinter and the Ehrlich reactions. The oil immediately colors on contact with air and resinification gradually sets in. Oxidation of this oil with chromium trioxide yielded isopropylmaleinimide, m.p. 82°, confirmed with an authentic specimen prepared. The oxidation of the same oil with nitrous acid yielded isopropylmaleinimide monoxime of m.p. 187°, C₇H₁₀O₂N₂, whose saponification gave the same maleinimide as above of m.p. 82°. The same treatment of dihydrokainic acid also yielded the same isopropylmaleinimide.
From the fact that the oxidation of the oil yielded a maleinimide compound and a decrease of one methyl, this oil was assumed to be α- or α′-methyl-β′-isopropylpyrrole and was confirmed to be not identical with α′-methyl-β′-isopropylpyrrole by comparison with the synthetic specimen. It follows, therefore, that kainic acid would be represented by the tentative formula (A), with a five-membered, hetero-ring with nitrogen.

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1) Friedelin was obtained from the bark of Shiia Sieboldii Makino (Fagaceae), Clerodendron trichotomum Thunb. (Verbenaceae), Zelkowa serrata Makino (Ulmaceae), and Salix japonica Thunb. (Salicaceae).
2) A new triterpenoid of m.p. 274° was obtained from the bark of Salix japonica and was designated as epifriedelinol, C₃₀H₅₂O. Epifriedelinol is oxidized to friedelin by chromic oxidation and undergoes isomerization to friedelinol on heating with sodium isoamyloxide.
3) Epifriedelinol and friedelinol are diastereomers with reverse steric configuration of the hydrogen and hydroxyl in their secondary alcohol.
4) Optical rotation of epifriedelinol and eriedelinol and their acetates are as follows: Epifriedelinol, m.p. 274°, [α]_D²⁸: +8.7°, and epifriedelinol acetate, m.p. 289°, [α]_D²⁸: +24.7°. Friedelinol, m.p. 297° (Drake, m.p. 301-304°), [α]_D²⁸: +16.1°, and friedelinol acetate, m.p. 306° (Drake, m.p. 316°), [α]_D²⁸: -13.7°.
5) Picein was obtained from the bark of Salix japonica.

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The course by which acetylcholine appears in honey is an important problem in connection with other minute components in honey. The presence of acetylcholine in the nectar of flowers of Japanese camelia and 7 kinds of pollens was examined by the Magnus method and by paper chromatography. Acetylcholine and histamine are not contained in the nectar of flowers of Camellia japonica L. Acetylcholine is absent in most of the pollens except in those of Alnus Sieboldiana Matsumura, though they contain histamine. These results confirmed that acetylcholine is not present originally in the nectar of flowers nor had dissolved out from the pollens occluded in the honey.

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In order to follow the course whereby acetylcholine appears in honey, honey bees were fed with sugar solution free from acetylcholine (glucose: fructose: water=3.5:3.5:3.0) and one added with 10γ/cc. of acetylcholine chloride, shut off from outside influence. Honey that accumulated in a new comb was collected and the presence of acetylcholine was examined by the Magnus method in both cases. The honey from bees fed on simple sugar solution clearly indicated contraction of guinea pig intestine, the amount of contraction being equal to about 0.2γ/cc. of acetylcholine. The one from bees fed on sugar solution containing acetylcholine showed a slightly stronger contraction than the former. From the present experimental results and those recorded in Part VIII of this series, it became clear that acetylcholine in honey is not derived from nectar of flowers or the pollens but is biogenetically formed in the honey bee itself and secreted into honey. Determination of acetylcholine in three different kinds of domestic Royal jelly by the paper chromatography and the Magnus method showed the content to be 1250-1625γ/g., an average of 1500γ/g., which is almost 100 times more than that in the honey. It was also confirmed that Royal jelly does not contain histamine and other factors which effects contraction of small intestine, acetylcholine being almost the only factor present.

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In connection with the presence of acetylcholine in honey and Royal jelly, the acetylcholine-like substance in the larvae and adult working and male bees was examined by the Magnus method. In the larvae, the majority was an acetylcholine-like substance, the amount being approximately 16γ/g. as acetylcholine chloride in working bees and 40γ/g. in male bees, practically without the presence of histamine. On the other hand, the amount of histamine in the adult working honey bee was 84γ/g. and 100γ/g. in the adult Vespa mandarinia Smith, the amount being larger than that of acetylcholine.

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Antibacterial properties and the presence of the vitamin B group were examined in 3 kinds of Royal jelly collected in the season when the honey is collected from rape, clover, horse chestnut, and Robinia pseudo-acacia L. There were no antibacterial action but the presence of the vitamin B group was found to be generally high, especially acetylcholine (1, 500γ/g.), pantothenic acid (170γ/g.), and biotin (3.5γ/g.), being one of the natural products of high vitamin B content. This fact suggests the significance of these vitamins for the growth of bee larvae.

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The structure of carpesia lactone was assumed as (I) (Fig. 2), in the previous paper. Dihydrocarpesia lactone is derived to diethyldithioacetal with ethanethiol and its reduction with Raney nickel gives desoxydihydrocarpesia lactone (II). Saponification of (II) with alkali to hydroxy acid and oxidation with chromium trioxide and pyridine yields desoxydihydro-oxocarpesic acid (IV). This keto acid gives negative Legal reaction, does not form a benzylidene compound, and does not undergo condensation with p-nitrosodimethylaniline that the formula (IV A) was assumed. It follows, therefore, that the structure of carpesia lactone would be represented by (I A). Condensation of dihydrocarpesia lactone with p-nitrosodimethylaniline and decomposition with sulfuric acid gave dihydrooxocarpesia lactone (VI) (cf. Fig. 2).

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Application of p-nitrophenylhydrazine to the periodate oxidation product of N-acetylglucosylamine yields, according to the amount of the reagent added, monohydrazone compound first, and then dihydrazone compound. Purification of the oxidation product with baryta and application of p-nitrophenylhydrazine results in the formation of α-acetiminoacetaldehyde p-nitrophenylhydrazone. The structures of the foregoing three compounds were determined by their decomposition and catalytic reduction.

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In order to examine the reaction of secondary arylamine N-glucosides and periodic acid, preparation of p-nitro-N-methylaniline N-glucoside tetraacetate was carried out. This was not successful by the general method of synthesizing N-glucosides but the objective compound was obtained, though in a poor yield, by the methylation of p-nitroaniline N-glucoside tetraacetate with methyl iodide and silver salts.

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1) Ethyl ester, m.p. 253°, and hydrazide, m.p. 275°, of purpurogallin-carboxylic acid were prepared.
2) These three compounds were ineffective against Staphylococcus aureus Terashima and Escherichia coli communior in 100, 000 dilution but was effective against Aoyama B strain of tubercle bacilli in 100, 000 dilution.

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A method of idenfying atropine or scopolamine in Opium Alkaloid-Atropine or -Scopolamine Injections was established. The parenteral solution is basified with ammonia by which papaverine, narcotine, and most of morphine precipitate. This is filtered and the filtrate is extracted with ether by which codeine and atropine or scopolamine dissolve in the organic solvent. Codeine and atropine are isolated by the Marmes' reagent and identified by the Vitali reaction. Atropine could not be identified in Eukodalhydrocotarnine-atropine injection by this method and this was effected by the addition of 2, 4-dinitrophenylhydrazine to the parenteral solution by which Eukodal precipitates. To this is added acetone to precipitate the excess reagent and centrifuged. The clear, supernatant solution is extracted with benzene into which transit atropine and hydrocotarnine. Atropine and hydrocotarnine are isolated by paper chromatography, the atropine band is extracted with methanol, and identified by the Vitali reaction.

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Three isomers of propanediol monostearate and two isomers of the distearate were prepared in pure state and the erroneous data in the existing literature for these compounds were corrected as follows: 1, 2-Propanediol monostearate-(1), m.p. 41.5°; monostearate-(2), m.p. 44.0°; and distearate-(1, 2), m.p. 59.0°. 1, 3-Propanediol monostearate-(3), m.p. 51.0°; distearate-(1, 3), m.p. 61.5°.

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Three kinds of bromopropanol were prepared by a more simple method and in a better yield than by the existing processes by the use of lithium aluminum hydride. 1-Bromopropanol-(2) was obtained in 48% yield from bromoacetone and 2-bromopropanol-(1) from α-bromopropionaldehyde or α-bromopropionyl bromide in 60% or 73% yield. Trimethylene glycol, the raw material for 3-bromoproanol-(1), was obtained in 37% yield by the reduction of diethyl malonate with lithium aluminum hydride.

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The influence of increasing portion of acetone on the ion exchange between sodium and hydrogen ion in cation exchangers was investigated. The equilibrium constants were measured by passing acetone-water solution of sodium chloride and hydrochloric acid (containing 0.05N of each cation) through the column of cation exchange resin, Results indicated that the selectivity of sodium ion increased with the acetone content of thesolution, in a manner where the reciprocal of logarithms of equilibrium constant was in linear relationship with the dielectric constant of the mixed solution.

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The enzymatic resolution of DL-methionine was carried out by employing commercial enzyme preparations, and optically active methionine was obtained in a good yield. To establish the optimum conditions for the resolution, various factors influencing the asymmetric hydrolysis of acetyl-DL-methionine were investigated.

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