The ultraviolet absorption spectra of hydroxytetralins, hydroxytetralones, their acetates, and their methyl ethers are compared. The spectra of hydroxytetralin derivatives consist of two bands, and that of hydroxytetralone derivatives, three bands. The introduction of a hydroxyl group to the aromatic ring of tetralin displaces the absorption band to a longer wave length region, increasing the intensity. The introduction of two hydroxyl groups, especially in 1, 4-positions, is more effective. The acetylation and the methylation of the hydroxyl group decrease the spectral effect of hydroxyl group in varying rates. Syntheses of some tetralin and tetralone derivatives are also described.

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β-(5-Nitro-2-furyl)-α-methylacrolein and β-(5-nitro-2-furyl)-α-ethylacrolein were prepared by the condensation of 2-(5-nitro) furfural with propionaldehyde and butyraldehyde, respectively, in the presence of piperidinium acetate as a catalyst. Preparation of β-(5-nitro-2-furyl)-α-bromoacrolein was accomplished by bromination in the usual manner. These new compounds were used as an antibacterial group in the preparation of Schiff bases with semicarbazides, hydrazides, and amines, and then antibacterial screening of these bases was carried out. From the screening results, β-(5-nitro-2-furyl)-α-methylacrolein semicarbazone, β-(5-nitro-2-furyl)-α-methylacrolein oxime, and 1-[β-(5-nitro-2-furyl)-α-bromoacrylidene]-2-isonicotinylhydrazine were found to exert great activity against tubercle bacilli.

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2, 4-Lutidine 1-oxide was converted to 2-hydroxymethyl-4-methylpyridine and 2-methyl-4-hydroxymethylpyridine by reaction with acetic ahydride, and its formation ratio was about 5 : 1. Besides these, 3-hydroxy-2, 4-lutidine was obtained as a phenolic base. In the case of the reaction of 2, 4-dimethylquinoline 1-oxide with acetic anhydride, 2-hydroxymethyllepidine and a small amount of 3-hydroxy-2, 4-dimethylquinoline were obtained but not 4-hydroxymethylquinaldine.

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1) β-Haloethyl esters of carboxylic acid was formed by the reaction of a carboxylic acid with ethylenehalohydrin in carbon tetrachloride, with a few drops of sulfuric acid as a catalyst. The β-haloethyl carboxylates thereby obtained were reacted with secondary or tertiary amines and several kinds of aminoalkyl carboxylate derivatives possessing antispasmodic action were prepared. 2) In the esterification of benzilic acid with ethylenehalohydrin, only the esterification occurs when the amount of sulfuric acid catalyst is small but in the presence of a large amount of the acid, concurrent etherification was found to occur. This was utilized in preparation of β-bromoethyl O-(β'-bromoethyl) benzilate (XIV) which was reacted with a secondary or tertiary amine and some novel derivatives of aminoalkyl carboxylate were obtained. 3) Application of tertiary amines with branched alkyl chain, such as diisopropylmethylamine, to β-bromoethyl diphenylacetate (IV) failed to cause the anticipated quaternization.

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Applicability of submerged culture was tested in order to obtain a suitable mycelial preparation of Trichophyton gypseum for respiratory study. The submerged culture supplied a very fine mycelial suspension, which could make quantitative handling of the preparation possible, as early as 4 days after inoculation. The suspension thus obtained was found to be more preferable than the slice or bored disc of the mycelial pad obtained by surface growth, in respiratory experiments, because the former, which showed a considerably shorter lag phase in the oxidation of glucose, was permeable to many substrates which were not apparently oxidized by the surface pad preparation, and was susceptible to respiratory inhibitors such as cyanide, azide, iodoacetate, and arsenite.

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The metabolic fate of PAS and Ac-PAS in rabbits was studied comparatively. About 74% of the 1g./kg. dose of PAS administered orally is excreted in the urine. Of this, 23∼60% are unchanged, 17∼42% as acetylated compounds, and 2∼3% as a glucuronide. About 1% of a 1.27g./kg. dose of Ac-PAS administered orally is deacetylated and 42∼68% is excreted in the unchanged form. PAS glucuronide was identified by means of paper chromatography. There were three unknown metabolites containing a free amino group in the urine and no increase in ethereal sulfate nor considerable decarboxylation of either PAS or Ac-PAS were observed.

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A new assay method of benzalkonium chloride was established, and it can be carried out rapidly and accurately. Its principle is to measure the intensity of a blue color that is developed by adding a stannous chloride solution to a solution of the combined substance made from benzalkonium chloride and phosphomolybdic acid.

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Culture samples collected at regular intervals during the tank culture of Eremothecium ashbyii were separated into the mycelium and broth. The mycelium was extracted with various solvents and the extracts were examined by paper chromatography and paper electrophoresis. The broth, as such or after concentration, was also investigated by the same methods. Development with the solvent system of butanol-ethanol-water afforded detection of the greatest number of substances in the mycelium and gave the best separation. From the spots fixed by various methods it was found that adenosine was formed besides riboflavin and FAD, in the early stage of the culture and then ATP was produced gradually. Despite many experiments FMN was never detected. On the other hand, formation process of ATP and FAD in the mycelium was also observed, and the conclusion was reached that in the culture of E.ashbyii FAD was produced from riboflavin and ATP.

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By successive oxidation with selenium dioxide and sodium dichromate followed by introdution of a hydroxymethylene group, a partial structure -C=C-CH₂-CH₂- was given for a diterpenic acid C₂₀H₃₀O₂ (II) which was isolated from the fruits of Japanese juniper. Further, as the acid (II) gave tetrahydro-7-isodextropimaric acid after consumption of two moles of hydrogen, the structure of (II) was concluded to be represented by △^{13, 14}-7-isodextropimaric acid. The structure of a doubly unsaturated compound obtainable from a hydroxymethyl ester (VI), an oxidation product of (V), was proposed to be △^{5, 13 : 9, 14}-7-isodextropimaric acid.

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A new simple estimation method of the distance r between the two carboxyl groups of a dicarboxylic acid by high frequency titration in nonaqueous medium is described. This method is based on the Coulomb's force between the two groups. In spite of its being very simple, relatively good results were obtained.

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O-Methyldauricine (VI) was synthesized by the Ullmann reaction of l-armepavine (VIII) and l-3'-bromo-O-methylarmepavine (X). It was characterized as the dimethiodide, which was confirmed to be identical with that of natural dauricine.

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Isochinolin-N-oxyd (I) geht beim Erhitzen mit Essigsaureanhydrid in Isocarbostyril (II) uber. Die Reaktion von (I) mit Tosylchlorid begleitet eine andere Umlagerung. (I) gibt beim Erhitzen mit Tosylchlorid in Chloroform eine syrupose Masse, die sich beim Behandeln mit wenig Methanol kristallinisch erstarrt. Sie bildet beim Umkristallisieren aus Methanol Nadeln vom Schmp. 184∼185° (III), deren Analysenzahlen mit C₁₆H₁₃O₃NS·C₇H₇O₂ClS ubereinstimmen. Aus ihrer Mutterlauge wurde (II) isoliert. (III) entsteht dabei in uberwiegender Menge. (III) wandelt sich beim Behandeln mit verd. Soda-Losung in Wurfeln vom Schmp. 92∼93° um, von der Zusammensetzung C₁₆H₁₃O₃NS (IV), welche als 4-Tosyloxyisochinolin identifiziert wurden. (III) entsteht in praktisch quautitativer Ausbeute, wenn man (IV) mit Tosylchlorid in chloroform erhitzt. Fur die Entstehung von (IV) bzw. (II) aus (I) schlagen die Verfasser eine anionotrope Umlagerung vor. (IV) gibt beim Erhitzen mit Schwefelsaure (38%) oder mit Natronlauge (20%) 4-Oxyisochinolin (V) neben einer kleinen Menge von (II). (V) gibt bei der katalytischen Reduktion mit Platinoxyd in Eisessiglosung 4-Oxy-Bz-tetrahydroisochinolin mit ca. 75% iger Ausbeute.

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The excretion rates of EHB and 3-keto-EHB in the urine of intact or partially hepatectomized animals receiving EHB or 3-keto-EHB were determined by use of paper chromatography in conjunction with ultraviolet spectrophotometry. Unchanged EHB was undetectable in the urine of intact animals. Approximately 44% of EHB administered was converted to 3-keto-EHB and excreted independently of the dosage. The excretion of 3-keto-EHB began in a period of the first 3 hrs. after an administration of EHB and completed within 24 hrs. (100 or 200 mg./kg.) or 48 hrs. (400 mg./kg.). About 32% of 3-keto-EHB administered was rapidly excreted but the fate of the remainder was undetectable. Partial hepatectomy prolonged the period of excretion of 3-keto-EHB and decreased the quantity of that. Unchanged EHB was detected in partially hepatectomized rats.

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N-Alkylephedrines were synthesized by heating a mixture of ephedrine and alkyl bromide under pressure. The alkylation proceeded with decreasing yield of the desired substance as the number of carbons of alkyl bromide increased, and there was, in the end, no yield at C₅, viz., amyl bromide. With alkyl bromides of higher moleculer weight than amyl, the alkylation was successfully carried out by the addition of equimolar amount of pulverized KOH. The N-alkylephedrines thus obtained were converted to the ammonium salts with methyl or ethyl iodide. The pharmacological effects of the compounds synthesized were examined by the Magnus method and these effects were compared with that of l-ephedrine. Among these compounds, N-butyl-, N-hexyl-, N-heptylephedrines, and dimethylbutyl-(β-phenyl-β-hydroxyisopropyl) ammonium iodide were found to have pharmacological effects almost equal to that of l-ephedrine, in the balance of inhibitory effect on tonic contractions by acetylcholine, histamine, and barium chloride.

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Flavonoids were explored in 290 kinds of ferns by paper chromatography, developed with AcOH·H₂O (3 : 2 and 3 : 17) and PhOH saturated with water, by one-dimensional ascending chromatography. As a result, luteolin, apigenin, quercetin, and kaempferol were found in some ferns, but many unknown spots were found which were assumed to be new materials or rare flavonoids.

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A simple mercury drop-time regulator shown in Fig.1 was assembled for polarographic study. It was clarified that this regulator did not disturb the diffusion layer of a cell solution and it had the practical utility for polarographic purpose.

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