Mold growth was inhibited, in an 80-day test, by ethyl rhodanacetate and Na-salt of dodecyl sulfate at 0.001% concentration, by p-methoxyphenyl-mustard oil, p-chlorophenyl-mustard oil, o-tolyl-mustard oil and phenyl-mustard oil at 0.001-0.003% concentration and by o-methoxyphenyl-mustard oil at 0.003-0.005% concentration. Allyl-isothiocyanate inhibited mold growth at 0.005% concentration for 23 days.
The ar-methiodide of quinine type base or of a base in which C9 position of quinine has been substituted by H or Cl, when heated with an aldehyde in EtOH solution, gives a dyestuff in which the loipon portion has separated and C9 combined with the aldehyde in styril type. If OH radical is present at C9, the base undergoes hydramine conversion and does not decompose. Presence of O-acyl radical at C9 results in partial hydramine conversion with some formation of a styril dye. Use of nitroso-aryl, instead of aldehyde, results in a similar decomposition, forming an anil dye corresponding to the styril.
The authors synthesized monosulfonyl and bis-sulfonyl compounds as listed in Table I, and the ultrax-violet ray absorption spectra of these compounds are shown in Figs. 1, 2, 3 and 4. 3-Acetosulfanilyl-thiazolon-acetosulfanilylimide (2) (Compound II, Table I) gives two crystals of decompn. 130-135° and 190-240°, respectively. As can be seen from Fig. 1, these compounds give identical spectrum so that the two must be the same compound, the former being a hydrate of the latter. Bissulfonyl compounds (Compounds II, III, VI, VIII and X), R2-sulfonylthiazolon-R1-sulfonimide (2), react with diethylamine and guanidine carbonate and quantitatively form 2-R1-sulfonamidethiazole and R2-sulfondiethylamide or R2-sulfonylguanidine. Bis-acetosulfanilimide and bis-p-nitrobenzenesulfonyl compound of 2-amino-4, 6-dimethylpyrimidine do not react either with diethylamine or guanidine carbonate.
Ground baleen whale meat was left at the room temperature (in Summer) for 144 hours with the addition of buffer solution of pH 2, 4.2, 5.9 and 7.7, respectively. The amount of formal titrating N was found to have increased in the two former solutions, but that of volatile basic N did not increase appreciably. Both these N values increased considerably in the latter two cases. The titration curve of baleen whale meat by 2N-HCl showed that the buffer action was week in the range of pH 3-2 and pH 6-5 but appeared comparatively strong in other portions. Whale meat containing a large amount of fat was found to have smaller buffer capacity compared to lean meat. The reaction between whale meat and HCl was found to be of a different nature between those at pH 6-3.5 and at less than pH 2, but both were shown, from titration curves, to have taken place within the range of pH 3.5-2. Tests to determine the feasibility of storing a chunk of whale meat by HCl were unsuccessful.
The present experiments were undertaken according to the same reaction theory as the partial reduction of pyridine derivatives which are the active group of cozymase and coferment reported at the General Meeting of the Pharmaceutical Society of Japan in 1940. The compounds taken up were quinoline methiodide, quinaldine methiodide and lepidine ethiodide which are part of the structure of cyanine dyestuffs. According to the equation Na2S2O4+2H2O→2NaHSO3+H2 2NaHSO3+2NaHCO3→2Na2SO3+2H2O+2CO2 the amount of CO2 here formed was determined volumetrically by Warburg's manometer, and following results were obtained. 1) Approximately 1mol. H2 was absorbed by 1mol. quinoline methiodide. 2) Approximately 2mol. H2 was absorbed by 1mol. quinaldine methiodide. 3) Approximately 1mol. H2 was absorbed by 1mol. lepidine ethiodide. The reduction products of (1) and (2) were experimentally prepared as the known N-melhyl-1, 2, 3, 4-tetrahydroquinoline, N-methyl-o-dihydroquinaldine and N-methyl-1, 2, 3, 4-tetrahydroquinaldine. Comparative studies showed that quinoline methiodide formed a dihydro compound if treated with hydrosulfite in NaHCO3 solution, although it was difficult to decide whether the compound was an ortho or a para substance. It was proved that quinaldine methiodide was reduced to N-methyl-1, 2, 3, 4-tetrahydroquinaldine, via dihydro compound by the action of hydrosulfite in NaHCO3 solution. Lepidine ethiodide reacted very slowly, the determination having made solely by manometer although it is assumed that it forms a dihydro compound.
The mechanism of the decomposition of aryl-stibonic acids was studied for the purpose of preparing stable and non-toxic stibonates. 4-Acetamidophenyl- and 3-chloro-4-acetamidophenyl-stibonic acids, when treated with alkali, gave aniline and 2-chloroaniline, respectively, besides antimonates. 4-Acetamidophenyl stibonic acid decomposed into aniline in a weakly acid condition. The authors presumed, therefore, that aryl-stibonic acids in general would decompose according to the following equation, in which φ represents an aromatic nucleus. φ-SbO3H2+H2O→φ-H+H3SbO4
Neostibosan is the improved Heyden 693 (diethylamine salt of p-aminophenylstibonic acid) but its method of preparation has been kept a secret. The analyses of this compound undertaken by the authors have revealed several new informations and it is assumed that Neostibosan is obtained by the addition of antimonic acid to Heyden 693.
Hasenbäumer gave a formula of C6H5⋅SbO3H2 for phenyl-stibonic acid. According to Schmidt, free stibonic acids are tri-acids composed of φ⋅SbO3H2, where φ stands for an aromatic nucleus. These formulae have been used customarily up to the present without any criticism but, it seems to the author that they are unreasonable. The author, therefore, offers a new formula, H[φ⋅Sb(OH)5] and its condensed form produced by dehydration, on the grounds of four reasons.
During the course of investigations into a substance which inhibited “fogging” in photographic emulsions, crude penicillin was found to be effective in this respect. Further observations proved that this substance was a decomposition product of penicillin and in order to observe its effective mechanism, various 4-carboxy-thiazolidine derivatives were synthesized as allied compounds of thiazolidine, one of the component part of penicillin structure. These synthesized compounds showed similar properties. Theses derivatives were found to be unstable against heat and difficult to recrystallize and the aldehydes possessing a double bond were found to be difficult in combining with cystein and even if they did combine, the condition of combination seemed to be different. It is assumed that the tendency to decompose by heat has some relationship to the mechanism of converting from decreased sensitivity to incrersed sensitivity during the ripening of emulsion.
The authors proved that the reaction product of acetylglycine and phenylhydrazine obtained by Sen (loc. cit.) was nothing but N-acetylglycine-phenylhydrazide, m.p. 204.5-206°, sintering at 200° (cor.). The condensation of hippuric acid with α-benzylphenylhydrazine directly gave α-benzylphenylhydrazone of l-phenylbenzylamine-2-phenyl-5-imidazolone, needles, m.p. 110°.
Esterification of cyanoacetic acid was made with phenolsulfonic acid-formaldehyde resin as a catalyst by which ethyl cyanoacetate was obtained in 80-85% yield. Terpineol was obtained in a good yield by the steam distillation of terpin hydrate J. P. under the presence of the resin. Distillation of cyclohexanol and resin at 150-160° gave cyclohexene in 70% yield.
Application of ethyl formate to ethyl diethyl acetacetate gives ethyl hydroxymethylene-diethylacetacetate which forms dioxodiethylpiperidine via aminomethylene compound. The author obtained this aminomethylene compound in a comparatively good yield by the application of formamidine hydrochloride on the diethyl compound. By other methods, the subject compound was obtained by the application of formalin on diethylacetacetic amide.
Catalytic change of limonene, with metallic catalysts, such as those having Cu, Ni and alkali hydroxides, at 260-360° resulted in obtaining terpinolene, α- and γ-terpinene, menthene-1, menthene-3, cymene and menthane, as well as compounds thought to be acetone, toluene and p-ethyltoluene. It has been revealed by this experiment that limonene, through terpinolene and terpinene, is dehydrogenated to cymene and that menthane is formed by the hydrogenation of terpinene to menthene which is subsquently hydrogenated to menthane. Acetone and toluene are directly formed from terpinolene and p-ethyltoluene.