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Volume 71, Issue 7
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Kohei Kojima, Yasuko Ando1951 Volume 71 Issue 7 Pages 625-626
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTwo kinds of alkaloids, protopine, m.p. 207-208, ° and α-allocryptopine, m.p. 159-161°, were obtained from Pteridophyllum racemodium Sieb. et Zucc., in ca. 0.1% and ca. 0.6% yield, respectively, of dried whole plant.View full abstractDownload PDF (418K) -
Kohei Kojima, Tsune Asada1951 Volume 71 Issue 7 Pages 626-629
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy the condensation of N4-acetylsulfanilamide and acid chloride in xylene or pyridine, N1-acyl-N4-acetylsulfanilamide was obtained. Deacetylation of these compounds in diluted caustic alkali yielded several kinds of N1-acylsulfanilamide. Acids used were anisic, piperonylic, 2, 5-dimethoxybenzoic, 2, 4-dimethoxybenzoic, 3, 4-methylenedioxycinnamic, 3, 4-methylenedioxyhydrocinnamic and o-methoxycinnamic acids. Formation of N1, N4-diacyl compounds was observed in case xylene was used in the condensation.View full abstractDownload PDF (837K) -
On the Formation of Vitamin B1. (1)Taizo Matsukawa, Shojiro Yurugi1951 Volume 71 Issue 7 Pages 629-632
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to clarify the mechanism of biosynthesis of thiamine, the manner of thiamine formation by the following reactions at a comparatively low temperatures of 21° and 30° was examined by the thiochrome method. Formic acid was used as reaction solvents in all the cases.
A) 2-Methyl-4-amino-5-formaminomethylpyrimidine hydrochloride (IV) and γ-aceto-γ-mercaptopropyl acetate (V).
B) (IV), γ-aceto-γ-chloropropyl acetate (VI) and H2S.
C) (IV) and γ-thioaceto-γ-chloropropyl acetate (VII).
D) (IV) and γ-thioacetopropyl acetate (VIII).
E) 2-Methyl-4-amino-5-thioformaminomethylpyrimidine (IX) and (VI).
Reactions A, B, C and E all showed the formation of thiamine but reaction D failed to give any indication of thiamine formation.View full abstractDownload PDF (741K) -
On the Formation of Vitamin B1. (2)Taizo Matsukawa, Shojiro Yurugi1951 Volume 71 Issue 7 Pages 633-636
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn continuation of the previous report, the manner of thiamine formation at 30° was examined by the thiochrome method. Formic acid was used as a solvent in all reactions.
A) 2-Methyl-4-amino-5-formaminomethylpyrimidine hydrochloride (I), γ-aceto-γ-chloropropyl acetate (III) and a thioketone, such as ethyl thioacetoacetate (V) or γ-thioacetopropyl acetate (VI).
B) (I) and ethyl β-(α′-aceto-γ′-acetoxypropyl)-mercaptocrotonate (VII).
C) (I) and γ-aceto-γ-mercaptopropyl alcohol (VIII).
D) (I) and γ-thioaceto-γ-chloropropyl alcohol (X).
E) (I), γ-aceto-γ-chloropropyl alcohol (IX) and a thioketone, (V) or (VI).
F) (I), γ-aceto-γ-hydroxypropyl alcohol (XI) and H2S.
G) (I), (XI) and cysteine or (V).
Thiamine formation was indicated in reactions A, B, C, D, E and F, but not in G.View full abstractDownload PDF (688K) -
On the Formation of Vitamin B1. (3)Taizo Matsukawa, Shojiro Yurugi1951 Volume 71 Issue 7 Pages 636-638
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFormation of thiamine by the following new reactions had been confirmed by the thiochrome method but thiamine was isolated as crystalline thiamine hydrochloride during the present experiments and the formation of thiamine definitely proved. Formic acid was used as a solvent in all reactions which were carried out at 100°.
A) 2-Methyl-4-amino-5-formaminomethylpyrimidine hydrochloride (I) and γ-thioaceto-γ-chloropropyl alcohol (III) or acetate (II).
B) (I) and γ-aceto-γ-mercaptopropyl alcohol (IV).
C) (I), γ-aceto-γ-chloropropyl alcohol (V) or acetate (VI) and a thioketone, such as γ-thioacetopropyl acetate (VII) or ethyl thioacetoacetate (VIII).
D) (I) and ethyl β-(α′-aceto-γ′-acetoxypropyl)-mercaptocrotonate (IX).View full abstractDownload PDF (556K) -
Shoshichiro Kimoto, Hiroshi Kimura, Shin-ichiro Sakai1951 Volume 71 Issue 7 Pages 639-640
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA method of synthesizing 3-bromoveratrol in a good yield was deviced. By the reaction of 3-bromoveratrol and p-cresol, 2, 3-dimethoxy-4′-methylbiphenyl ether was prepared, oxidized by potassium permanganate to an acid and led to 2, 3-dimethoxybiphenyl ether-4′-acetic acid by rearrangement according to the Arndt-Eistert method.View full abstractDownload PDF (337K) -
Studies on 4′-Chloro, -Bromo and -Hydroxy-4-nitrophenyl Ethers by Polarographic Method and Supplement to the Study on Partial Reduction of 4, 4′-Dinitrodiphenyl EtherYasushi Mashiko1951 Volume 71 Issue 7 Pages 640-643
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSElectrolytic potentials of 4-nitro-4′-bromo-(I), 4-nitro-4′-chloro (II), and 4-nitro-4′-hydroxy (III) derivatives of biphenyl ether were determined by the use of mercury dropping electrodes by polarography. The samples were saturated in 50 vol.% methanol of pH 7.0 and E1/2 was determined with 1-N-calomel electrode as the standard. Values obtained were: -0.813 volt for (I), -0.829 volt for (II) and -0.863 volt for (III). Partial hydrolysis of 4, 4′-dinitrobiphenyl ether, described in the previous report, was carried out further using Na2S and SnCl2 as the reducing agents. Na2S gave the best results and SnCl2 gave a poor yield. S″ is assumed to be oxidized to S2O3″ by which NO2 is reduced to NH2. The results of partial reduction and electrolytic reduction of 4, 4′-dinitrobiphenyl ether and 4-amino-4′-nitrobiphenyl ether by polarography were in good agreement.View full abstractDownload PDF (716K) -
Komei Miyaki, Nisaburo Ikeda, Yoshimi Ito, Daiji Mizuno1951 Volume 71 Issue 7 Pages 643-646
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSMethyl-, ethyl-, chloro-, hydroxy-, amino-, anilino-, anisidino-, phenetidino-, methylmercapto- and ethylmercapto-1, 4-naphthoquinones were synthesized and their antibacterial properties examined. During the synthesis of 2-methylmercapto derivative, 2, 3-dimethylmercapto derivative was obtained as a byproduct and a good method for its synthesis was found. In the same manner, 2, 3-diethylmercapto derivative was also obtained. The results of their antimicrobial tests against bacteria, fungi, yeast and trichophyton are given in Tables I and II. Antimicrobial actions of 2-amino-, 2-methylmercapto-, 2-ethylmercapto-, 2, 3-dimethylmercapto- and 2, 3-diethylmercapto-1, 4-naphthoquinones are generally strong. 2-Methylmercapto-1, 4-naphthoquinone possesses a structure similar to menadione and therefore, its general pharmacological properties were examined. As a result, it was found to possess actions similar to menadione in promoting blood coagulation and shortening of prothrombine time.View full abstractDownload PDF (727K) -
Taichiro Komeno1951 Volume 71 Issue 7 Pages 646-648
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA few hydantoin derivatives containing pyridine or quinoline nucleus were synthesized by the Bucherer's reaction.View full abstractDownload PDF (545K) -
New Facts on Akabori ReactionEiichi Takagi1951 Volume 71 Issue 7 Pages 648-651
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs a result of studies on Akabori reaction (A formula), the following facts were found: (1) In the reaction between benzaldehyde and dl-N-methylalanine, dl-ephedrine and dl-φ-ephedrine are obtained irrespective of the use of pyridine. (2) Similarly, two kinds of dl-compounds of 1-(3, 4-methylenedioxyphenyl)-2-methylaminopropane-1-ol are obtained by heating directly piperonal and dl-N-methylalanine. (3) A new reaction (B formula), differing from the Akabori reaction, takes place by heating directly benzaldehyde and dl-alanine by which benzylamine, 1, 2-diphenylethanolamine (2 kinds of dl-compounds), acetaldehyde and carbon dioxide are formed. From above results, it has been assumed that, when the amino radical in the amino acids used is primary, the reaction of B-type occurs, while when it is secondary, the A-type reaction occurs.View full abstractDownload PDF (1022K) -
A New Reaction giving Alkamines and 1, 2-Diphenylethanolamine Series. (1)Eiichi Takagi, Hiroshi Ichikawa, Isao Ensaka1951 Volume 71 Issue 7 Pages 652-655
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt has been found that the new reaction that took place as a result of reacting benzaldehyde and dl-alanine was a common reaction among the allied aliphatic α-amino acids. The basic substances obtained by reacting benzaldehyde with dl-α-aminoisobutyric acid, dl-α-aminobutyric acid and glycine, respectively, were found to he benzylamine and two kinds of dl-compounds of 1, 2-diphenylethanolamine. The carbonyl compounds obtained as their by-product, were found to be acetone and propionaldehyde in the first two cases, but the third was not the formaldehyde expected. From the considertions of the present and the previous experiments on dl-alanine, it seems that these reactions follow the general reaction as represented by equation (I).View full abstractDownload PDF (847K) -
A New Reaction giving Alkamines and 1, 2-Diphenylethanolamine Series. (2)Eiichi Takagi1951 Volume 71 Issue 7 Pages 655-657
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe new reaction previously found was tested with (i) anisaldehyde and dl-alanine; (ii) piperonal and dl-alanine, and (iii) piperonal and dl-α-aminoisobutyric acid, and in these cases, also, the new reactions were found to take place. A reaction of aliphatic α-amino acids possessing a tertiary amino group, such as dl-dimethylalanine and dl-α-dimethylaminoisobutyric acid, with benzaldehyde was tried but decarboxylation failed to take place in these cases. It has been known that the reaction of benzaldehyde and dl-alanine in the presence of pyridine yields dl-ψ-norephedrine but, in this case too, the new reaction was found to have taken place. Summarizing the results obtained in the past three reports, it can be said that the reaction between aromatic aldehydes and aliphatic α-amino acids proceed in three different ways according to the kind of the amino group present: (i) The new reaction occurs with primary amino group; (ii) Akabori reaction chiefly takes place with secondary amino group; and (iii) no reaction occurs in the case of tertiary amino group.View full abstractDownload PDF (751K) -
Eiichi Takagi1951 Volume 71 Issue 7 Pages 658-662
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn connection with the reaction of aromatic aldehydes and α-amino acids, Akabori reactions of optically active amino acids were examined in the case of benzaldehyde and l(+)-N-methylalanine, and it was found that no optically active product could be obtained. As a general summarization of the experimental results obtained to date, the differences in reactions due to primary, secondary and tertiary amino groups were considered from the reaction mechanism and explanations reached through the electronic theory. In addition, from a qualitative observations on the reactions between aromatic aldehydes and α-amino acids, the following were found to be true: (i) The acyl derivatives of α-amino acids do not react; (ii) compounds such as anthranilic acid in which the amino group is directly attached to the aromatic nucleus also fail to react; and (iii) special kinds of carbonyl compounds, such as enanthaldehyde, cinnamaldehyde and benzoin, also react as aldehydes.View full abstractDownload PDF (919K) -
Synthesis of PyridothiazolesYuzuru Yamamoto, [in Japanese]1951 Volume 71 Issue 7 Pages 662-667
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS2-Bromo-, 2-isopropoxy- and 2-allyloxy-5-aminopyridines were prepared as the original materials. By the application of natant dithiocyanogen to 95% acetic acid solutions of 3 (5)-aminopyridines, nine kinds of pyridothiazoles were obtained. 2- and 5-aminopyridines are comparatively easily affected by dithiocyanogen, when a substituent that shows a large enough -E effect to compensate for the +E effect of the nuclear nitrogen is present in the 6- and 2-positions, respectively, and form thiocyano derivatives which change to pyridothiazoles. The ultraviolet absorption, maxima of pyridothiazoles, 2-methoxy-5-aminopyridine, 2-aminothiazole, and 2-amino-6-methoxybenzothiazole were comparatively studied.View full abstractDownload PDF (1245K) -
Mechanism for the Formation of N-Substituted Thiothiazolone-(2) Compounds. (2)Taizo Matsukawa, Takeo Iwatsu1951 Volume 71 Issue 7 Pages 667-670
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPreviously, Tomita and the others reported (This Journal: 68, 151 (1948)) that the substance obtained by the reaction of ammonium (2-methyl-4-aminopyrimidyl-(5))-methyldithiocarbamate (I) and γ-aceto-γ-chloropropyl alcohol (V) was 2-mercapto-3-(2′-methyl-4′-aminopyrimidyl-(5′))-methyl-4-methyl-5-β-hydroxyethylthiazolium chloride (III), but, according to reexamination of the reaction by the authors, the substance was found to be not (III) but the hydrochloride, m.p. 180° (decomp.), of α-aceto-γ-(2-methyl-3-chlorotetrahydrofuryl-(2))-oxypropyl (2′-methyl-4′-aminopyrimidyl-(5′))-methyldithiocarbamate (IX), m.p. 170-200° (decomp.). The chief reaction product in this case is (IX), and a small amount of 2-thio-7-methyl-1, 2, 3, 4-tetrahydropyrimido-(4, 5-α)-pyrimidine (VII) is also formed. Similarly, (IX) and (XI) are obtained by the condensation of 2-methyl-4-amino-5-aminomethyl-pyrimidine and γ-aceto-γ-chloropropyl-(α) 2-methyl-3-chlorotetrahydrofuryl-(2) ether with carbon disulfide under the presence of ammonia.View full abstractDownload PDF (918K) -
Mechanism of Growth Promoting Action of IndoleIwao Arai1951 Volume 71 Issue 7 Pages 671-673
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy the measurement of absorption spectrum of the colored solution obtained by the application of p-dimethylaminobenzaldehyde reagent to bacterial cells, it was determined that tryptophane is synthesized in the bacterial cells of Bacillus typhosus cultivated either on synthetic medium containing indole or in asparagine-cystine medium.View full abstractDownload PDF (566K) -
Mechanism of Growth Promoting Action of Tryptophane. (2). With Additional Observations on the Inhibition of Growth of B. Typhosus by Several Indole DerivativesIwao Arai1951 Volume 71 Issue 7 Pages 673-677
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe growth promoting actions against Bacillus typhosus were examined with the following seven compounds: tryptophane methyl ester hydrochloride (I), acetyltryptophane (II), N-methyltryptophane (Abrin) (III), indole-pyruvic acid (IV), indole-3-ethylamine hydrochloride (V), 2-methyltryptophane (VI) and 5-methyltryptophane (VII). Only (I), (III) and (IV) were found to be effective in promoting growths and these compounds are those that possess, or have the ability to acquire, peptide bonding. 2- and 5-methyltryptophane were fonnd to inhibit the growth promoting action of indole but their antagonism against tryptophane was not so apparent. 2- and 5-methylindole do have the tendency to inhibit the utilization of tryptophane by Bacillus typhosus but their antagonism against indole were found to be very strong.View full abstractDownload PDF (811K) -
Syntheses of 2- and 5-MethyltryptophaneIwao Arai1951 Volume 71 Issue 7 Pages 677-679
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt was found that 2- and 5-methyltryptophane can be prepared in a good yield from 2- and 5-methylgramine, respectively, by their condensation with diethyl nitromalonate to ethyl α-nitro-α-carbethoxy-β-(x-methyl-3-indole)-propionate with subsequent decarboxylation, reduction and hydrolyses.View full abstractDownload PDF (532K) -
Mechanism of the Co-operative Growth Promoting Action of SH-CompoundsIwao Arai1951 Volume 71 Issue 7 Pages 679-681
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe growth promoting action of tryptophane and indole against Bacillus typhosus are remarkably accelerated in the presence of compounds -SH group, such as cystine. No difference in their co-operative growth promoting effects was found when cystine was replaced by ascorbic acid. This seems to signify that cystine acts as an adjustor of oxido-reduction potentials suitable for bacterial growth.View full abstractDownload PDF (468K) -
Tsutomu Momose, Tatsuo Shoji1951 Volume 71 Issue 7 Pages 681-683
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSp-Aminomethylphenyl sulfone compounds of acetone, acetic acid, ethanol, methyl iodide and acetophenone were synthesized from sodium p-formylamino- or p-phthaliminomethylphenylsulfinate by condensation with monochloroacetone, monochloroacetic acid and its ester, ethylene chlorohydrin, methylene iodide and bromoacetophenone, with subsequent deformylation or dephthalylation. The antibacterial actions of these compounds were found to be very weak, being far inferior than that of p-aminomethylphenyl methyl sulfone. However, the latter compound was quite easily obtained from p-aminomethylphenyl sulfone-acetone by deacetylation, or from p-aminomethylphenyl sulfone-acetic acid by decarboxylation.View full abstractDownload PDF (560K) -
Tsuneo Matsuo1951 Volume 71 Issue 7 Pages 684-685
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to test the physiological property of “Kôha”, a thiocyanine dyestuff, the following dyes possessing various styril groups in the 2-position of thiazole nucleus were synthesized by the condensation of 2, 4-dimethylthiazole and the following aldehydes: Benzaldehyde, salicylic aldehyde, p-hydroxybenzaldehyde, o-methoxybenzaldehyde, anisaldehyde, protocatechualdehyde, vanillin, veratrumaldehyde, piperonal, p-phenoxybenzaldehyde, p-bromobenzaldehyde, m-nitrobenzaldehyde, p-nitrobenzaldehyde, p-dimethylaminobenzaldehyde, cinnamic aldehyde, furfural and chloral.View full abstractDownload PDF (458K) -
Sedative and Hypnotic ActionsYosoji Ito, Haruo Kitagawa, Tameo Hiramori, Yukio Suzuki, Michiko Yama ...1951 Volume 71 Issue 7 Pages 686-692
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTwenty-three kinds of coumarin derivatives were prepared and their analgesic and hypnotic actions were examined using mice. The potency and toxicity of each drug were compared by the values of HD50 (hypnotic dose), SD50 (sedative dose) and LD50 (lethal dose) which were determined by van der Waerden's “Flächemethode” and by Behrens-Kärber method. As a result, the following were assumed: (1) The double bond between-3-and 4-positions in the coumarin nucleus plays an important rôle for the appearance of the efficacy. (2) The potency was found to be in the order of coumarin nucleus with α-pyrone ring condensed with naphthalene at the ortho, the same condensed with benzene, and the benzene condenesed to the 6-position of α-pyrone. (3) Both α- and β-compounds were ineffective in the ethyl naphthopyrone-acetate and 4-methylnaphthopyrone series. (4) A very powerful effect was found in ethyl coumarin-3-carboxylate alone in the ethyl coumarin-carboxylate series. (5) No remarkable difference was found to exist between α- and γ-pyrone rings. (6) The nature of hypnotic actions of carboxylic acid derivatives and alkylcoumarins is different.View full abstractDownload PDF (1136K) -
Synthesis of PyrrylpyrrolHeisaburo Kondo, Setsuro Ohno1951 Volume 71 Issue 7 Pages 693-694
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCondensation of ethyl aminoacetoacetate and pyrroylacetic ester in 75% acetic acid did not proceed as planned but the condensation of aminopyrroylacetic ester and acetoacetic ester was successfully concluded to yield sandy crystals, m.p. 229-231° (decomp.), which was assumed to possess a structure as shown in (VII).View full abstractDownload PDF (316K) -
Tertiary Amine Salts of PenicillinSueo Tatsuoka, Hiromu Hitomi, Masuo Miyamoto, Minoru Kawashima1951 Volume 71 Issue 7 Pages 694-698
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to find a method convenient to the purification and determination of penicillin, several kinds of tertiary amines were reacted on crude penicillin by which stable amine salts were obtained in a pure state. It was found possible to obtain alkali salts of total penicillin in pure form from these amine salts. Total penicillin was separated into various penicillins, and penicillin F and G isolated, by partition chromatography.View full abstractDownload PDF (916K) -
Primary and Secondary Amine Salts of PenicillinSueo Tatsuoka, Akira Morimoto, Hiromu Hitomi, Takashi Tamura1951 Volume 71 Issue 7 Pages 698-701
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPenicillin was said to be unstable against primary and secondary amines but the authors obtained amine salts by the application of several kinds of primary and secondary amines. These amine salts were found to be convenient for the purification and identification of penicillin and from which alkali salts of penicillin were obtained in pure forms.View full abstractDownload PDF (758K) -
Preparation of Metal Salts of PenicillinSueo Tatsuoka, Hiromu Hitomi1951 Volume 71 Issue 7 Pages 701-702
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe various amine salts of penicillin obtained from crude penicillin or final rich water were put to exchange reactions with metallic alcoxide or phenoxide in organic solvents by which metal salts of pure penicillin were obtained.View full abstractDownload PDF (341K) -
Synthesis of Acetaminomalonic Ester and Acetaminocyanoacetic EsterSueo Tatsuoka, Tomoji Kinoshita, Ritsuo Nakamori1951 Volume 71 Issue 7 Pages 702-704
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSEthyl acetaminomalonate was obtained in a good yield by the treatment of ethyl isonitrosomalonate with zinc, acetic acid and acetic anhydride in the presence of carbontetrachloride or chloroform. Reduction of isonitrosocyanoacetic ester with diluted acetic acid and zinc, followed by acetylation with acetic anhydride, or reduction of acetyloximino-cyanoacetic ester with zinc and diluted acetic acid, yield acetaminocyanoacetic ester in a good yield.View full abstractDownload PDF (546K) -
Masaichiro Masui, Yuichi Kamura1951 Volume 71 Issue 7 Pages 705-708
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSVolumetric analysis in which the end point is given by high frequency has become the object of interest. The authors devised and prepared an apparatus, using a very common vacuum tube, UX-12A, which was simple as well as stable and sensitive. It was chiefly an improvement on the method of Jensen and Parrack. The mechanism of the loading effect that makes up the principle of the titration method, was assumed to be caused by the capacitative and conductive properties, and the utilization of these properties were shown to be most important. From these facts, the relationship between the concentration and sensitivity, or concentration and frequency becomes apparent. This method, as long as it does not interfere with titration reaction, is not affected by the occlusion of any foreign matter. It follows, therefore, that neutralization titration in the presence of KMnO4 or Cr2O7″, which is hardly performed by other means, can correctly be estimated by this method.View full abstractDownload PDF (737K) -
Yoshio Tajika, Yoshihiro Nitta, Jitsuho Yomoda, Hiroshi Oya1951 Volume 71 Issue 7 Pages 709-710
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn accordance with the reactions carried out by King and the others, several kinds of 2-aminothiazole derivatives were synthesized and their antibacterial actions tested against Staphylococcus aureus.View full abstractDownload PDF (350K) -
Isonitrosoaceto-p-anisidide and 5-MethoxyisatinMasaru Akahoshi1951 Volume 71 Issue 7 Pages 710-711
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDuring the course of examination on the isatin synthesis by the isonitrosoacetanilide method, some questions arose as to its reaction mechanism and, therefore, some unknown derivatives of isatin were synthesized by this method. Those obtained were 5-methoxyisatin and its phenylhydrazone from isonitroso-p-aniside synthesized from p-anisidine.View full abstractDownload PDF (360K) -
Fukujiro Fujikawa, Hiroshi Fujii, Yuhei Hitosa1951 Volume 71 Issue 7 Pages 712
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAntiseptic actions against soy sauce were tested with 3-methyl-4-thiocyano-6-isopropylphenol (I), 2-chloro-3-methyl-4-thiocyano-6-isopropylphenol (II), 4-cyclohexyl phenol (III), and 4-cyclohexyl-2-chlorophenol (IV). (II) and (III) at a concentration of ca. 0.005%, and (I), at a concentration of about 0.003%, were found to inhibit growth of mold during a 50-day test period.View full abstractDownload PDF (145K) -
Synthesis of o-Aminophenol Higher Alkyl Ethers and Their Bacteriostatic Actions on Mycobacterium tuberculosisRyuzaburo Nodzu, Hiroshi Watanabe, Shinzaburo Oka, Chuzo Nagaishi, Tak ...1951 Volume 71 Issue 7 Pages 713-716
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSome higher alkyl ethers of o-aminophenol were prepared and antibacterial actions of their hydrochlorides against human type tubercle bacilli were tested in vitro (Kirchner medium) and by S. C. C. method. Compounds synthesized were ethers of methyl, ethyl, butyl, hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl and benzyl. As long as the alkyl group in these ethers are straight-chain, saturated carbons of even number, there is a definite relationship between the length of the alkyl chain and the antibacterial action, the latter increasing with the increase of the number of carbon atoms. The maximum action (1:128, 000, by S. C. C. method) was found with an alkyl chain of 12 carbons, increase of carbon atoms above that resulting in the decrease of antibacterial action.View full abstractDownload PDF (868K) -
Alkylation of Ethyl Acetoaminocyanoacetate with EstersSueo Tatsuoka, Hiroshige Miyazaki1951 Volume 71 Issue 7 Pages 716-718
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy reacting dimethyl sulfate and various alkyl p-toluenesulfonate to ethyl acetaminoacetate, corresponding ethyl alkylacetaminocyanoacetates were prepared. The preparative method for β-methylmercaptoethanol was simplified, and its p-tosyl ester was prepared.View full abstractDownload PDF (594K) -
Resolution of Racemic MethionineSueo Tatsuoka, Mikio Honjo, Tomoji Kinoshita1951 Volume 71 Issue 7 Pages 718-719
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOptical resolution of methionine was carried out by bonding α-bromo-d-camphor-π-sulfonic acid to racemic methionine methyl ester.View full abstractDownload PDF (392K) -
Mechanism for the Formation of N-Substituted Thiothiazolone-(2) Compounds. (3)Taizo Matsukawa, Takeo Iwatsu1951 Volume 71 Issue 7 Pages 720-724
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPreparation of α-aceto-γ-(2-methyl-3-chlorotetrahydrofuryl-(2))-oxypropyl (2′-methyl-4′-aminopyrimidyl-(5′))-methyldithiocarbamate (III) and its hydrochloride (IV) by the condensation of ammonium (2-methyl-4-aminopyrimidyl-(5))-methyldithiocarbamate (I) and γ-aceto-γ-chloropropyl-(α) 2-methyl-3-chlorotetrahydrofuryl-(2) ether (II), was described in the previous (19th) report. In order to confirm the structures of (III) and (IV), (III) was treated with HCl, and (IV) heated to 180°, by which 3-(2′-methyl-4′-aminopyrimidyl-(5′))-methyl-4-methyl-5-β-hydroxyethylthiothiazolone (2) (V) was obtained besides some oily substance which was led to 3-(2′-methyl-4′-hydroxypyrimidyl-(5′))-methyl-4-methyl-5-β-hydroxyethylthiothiazolone-(2) (IX) or 2-amino-4-methyl-5-β-hydroxyethylthiazole (X), by which the oily substance was proved to be γ-aceto-γ-chloropropyl alcohol (VI) or (II). These have proved, beyond doubt, that the assumed structures for (III) and (IV) were correct.
(II) changes to (VI) by a short-time heating with a small amount of water. Condensation of (VI) with 2-methyl-4-amino-5-aminomethylpyrimidine (XIV), CS2 and NH3, yields α-aceto-γ-hydroxypropyl (2-methyl-4-aminopyrimidyl-(5))-methyldithiocarbamate (XV) which changes to (V) upon treatment with HCl, and to 2-thio-7-methyl-1, 2, 3, 4-tetrahydropyrimido-(4, 5-d)-pyrimidine (XVI) by the application of alkali hydroxide or by heating its crystals to 190-200°.View full abstractDownload PDF (951K) -
Synthesis of 3, 4-bis-(3-Hydroxy-4-ethoxyphenyl)-n-hexaneAkira Sakuma1951 Volume 71 Issue 7 Pages 724-726
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS3, 4-bis-(3-Hydroxy-4-ethoxyphenyl)-n-hexane (III) was obtained by the reaction of 3, 4-bis-(3, 4-methylenedioxyphenyl)-n-hexane and methylmagnesium iodide. (III) is dimorphous and is obtained with m.p. 127° and 134°, the lower m.p. compound transiting to that of the higher m.p. by fusion. Heating (III) with HBr yields a tetrahydroxy compound. Thermal decomposition of the hydrogenated product of 3-methoxy-4-ethoxypropiophenone azine yields a dimethyl ether of (III).View full abstractDownload PDF (714K) -
Nitration of 6-Substituted Quinoline-N-oxidesToshihiko Okamoto1951 Volume 71 Issue 7 Pages 727-730
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe effect of the N-oxide group in quinoline-N-oxide is more striking at a higher temperature. Nitration of 6-methyl-, 6-chloro-, and 6-bromo-quinolines at a low temperature gives 5-nitro compounds, while that at a higher temperature gives 4-nitro compounds. Due to the effect of the methoxyl group, 6-methoxyquinoline-N-oxide does not yield a 4-nitro compound. 4-Nitro comound is quantitatively obtained from 6-nitroquinoline-N-oxide by nitration at a low temperature.View full abstractDownload PDF (989K) -
Shichiro Akiya, Setsuzo Tejima, Hirotomi Harada1951 Volume 71 Issue 7 Pages 730-736
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe agar substance from the agar preparation made from Gracilaria Confervoides Grev., was purified and chemically studied. It was hydrolyzed completedly with 1N-H2SO4, and d-galactose isolated as crystals. By partial hydrolysis in a short period of time with 0.02 N- or 0.01 N-H2SO4, five kinds of oligosaccharide were obtained whose analytical values and molecular weights were compared with those of the original agar substance. Acetyl- and methyl-agar were prepared and their properties were found to be very similar to those of agar substance obtained from Gelidium Amansii Lam. However, complete methylation product of the former could not be obtained. The content of sulfuric acid was found to be much less in the agar from Gracilaria Confervoides than that from Gelidium Amansii.View full abstractDownload PDF (1280K) -
Electrolytic Oxynitration of TolueneJun Mizuguchi, Shoji Matsumoto1951 Volume 71 Issue 7 Pages 737-740
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSElectrolytic oxynitration of toluene was carried out with platinum or electrodeposited lead peroxide as an anode and 40% nitric acid as the electrolytic solution. The oxidation products obtained were benzaldehyde, benzoic and oxalic acids, nitration product was p-nitrotoluene, and the oxynitration products, 4-nitro-o-cresol and benzyl nitrate. It is an interesting fact that the intermediates of electrolytic oxidation, benzyl alcohol and o-cresol were determined as benzyl nitrate and 4-nitro-o-cresol, respectively.
It was found as a result of close observation on electrolysis products that, in this reaction, the lead peroxide anode shows remarkable surface activity.View full abstractDownload PDF (802K) -
Takeo Tsukamoto, Takeo Ohtaki1951 Volume 71 Issue 7 Pages 741-742
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOvaries, testicles and adipose bodies in their neighborhood were isolated from a total of about 7, 300 toads, Bufo melanostictus Schneider, caught in the suburbs of Taipei City, Formosa, between March and the middle of August. Those separated articles were divided by sexes and by seasons, and each were digested with hot carbon tetrachloride to determine constants of the fats thereby obtained.View full abstractDownload PDF (359K) -
Takeo Ohtaki1951 Volume 71 Issue 7 Pages 742-743
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs a continuance of examination of general properties of fatty substance obtained from the testicles of Formosan toads, Bufo melanostictus Schneider, studies were made on the products obtained by its saponification by 10% methanolic potash. Results obtained shows: (i) The non-saponifiable matter include carotenoid (detected by antimony trichloride reaction), cholesterol (proved as dibromoacetate) and a steroid that gives an acetate of needles, m.p. 119-125°. (ii) The acid portion is composed mostly of liquid acid in which a very minute amount of higher unsaturated acid is present, and solid acid of C16 and C18.View full abstractDownload PDF (382K) -
Takeo Tsukamoto, Takeo Ohtaki1951 Volume 71 Issue 7 Pages 743-744
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOvaries of 1062 toads, Bufo melanostictus Schneider caught in the suburbs of Taipei, Formosa, during July and August, were digested with hot carbon tetrachloride and 209g. (about 10% of the weight of ovaries) of fatty oil was obtained as dark reddish brown, viscous oil at a room temperature, with a characteristic odor. The constants of the oil were: d415 0.9670; nD27 1.4850; acid number 24.0; saponification number 193.0; iodine number 85.2; nonsaponifiable matter 2.95%; hexabromide value 3.98. In other words, it is composed of 84.44% triglyceride, 12.61% of free fatty acids and 2.95% of nonsaponifiable matter.View full abstractDownload PDF (339K) -
Takeo Ohtaki1951 Volume 71 Issue 7 Pages 744-746
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFollowing results were obtained by examination of the total fatty acids and the non-saponifiable matter yielded by saponification of 30g. of ovary oil by alcoholic potash: (i) Total fatty acids yielded solid acids composed of palmitic and stearic acids, and liquid acids composed chiefly of oleic acid with a small amount of higher unsaturated acid mixed in it. (ii) The non-saponifiable matter yielded a large amount of cholesterol and a minute amount of steroid that gave an acetate of m.p. 129-129.5°. The presence of carotenoid was assumed from the striking coloration shown by antimony trichloride.View full abstractDownload PDF (500K) -
Takeo Ohtaki1951 Volume 71 Issue 7 Pages 747-751
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS35g. of free fatty acids was isolated from 115g. of ovary oil of Bufo melanostictus Schneider and the acids contained palmitic and stearic acids, and some unsaturated C16 and C18 acids. Fractionation of the bromination products of the neutral fatty portion by the difference of solubility in various solvents proved the presence of linoleo-dilinolein bromide, palmito-diolein bromide and triolein bromide, the latter two composing majority of bromoglycerides. No substances containing steroid were obtained in the present studies.View full abstractDownload PDF (885K) -
Takeo Ohtaki1951 Volume 71 Issue 7 Pages 751-753
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSome oil was obtained from the ovaries of Bufo melanostictus Schneider caught in the suburbs of Taipei, Formosa, during March-May and June-July. Examination of the non-saponifiable matter of this oil, in both cases, revealed the presence of cholesterol and γ-sitosterol. The ratio of these two substances were in a reverse order in spring (oviposition season) and in the summer, the amount of γ-sitosterol being larger in the spring, and that of cholesterol smaller, while the situation was vice versa in the summer.View full abstractDownload PDF (602K) -
Fukujiro Fujikawa, Kunio Nakajima1951 Volume 71 Issue 7 Pages 754-755
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe molding of soy sauce was already apparent at 8.5th day of the test with the use of 4-benzylresocinol in an approximate concentration of 0.01%. However, its monohalogen derivatives, 6-chloro-4-benzylresorcinol, at ca. 0.005%, and 4′-chloro- and 4′-bromo-2, 4-dihydroxydiphenylmethane, at ca. 0.007%, sucessfully inhibited the growth of mold in soy sauce during a 50-day test period. On the other hand, 2′-chloro-2, 4-dihydroxydiphenylmethane, at ca. 0.01% concentration, was not able to stop mold-growth after 42 days. In the dichloro derivatives, 5, 4′-dichloro-2, 4-dihydroxydiphenylmethane, in a concentration of ca. 0.003%, and 3′, 4′-dichloro-2, 4-dihydroxydiphenylmethane, at ca. 0.007%, were also able to inhibit mold-growth during a 50-day test period. From above results, it is seen that the halogen substitution strengthens antiseptic action although there is a good deal of difference according to the position of the halogens substituted.View full abstractDownload PDF (381K) -
Syntheses of Imidazo Compounds. (1)Taizo Matsukawa, Syoiti Ban1951 Volume 71 Issue 7 Pages 756-759
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS6-p-Nitrophenylimidazo-(2, 1-b)-thiazole, 6-p-nitrophenyl-3-methylimidazo-(2, 1-b)-thiazole, 6-p-nitrophenyl-3-methyl-2-β-hydroxyethylimidazo-(2, 1-b)-thiazole, 6-p-nitrophenyl-3-methyl-2-β-acetoxyethylimidazo-(2, 1-b)-thiazole, 6-p-nitrophenyl-3-methyl-2-carbethoxyimidazo-(2, 1-b)-thiazole, and ethyl 6-p-nitrophenyl-3-methylimidazo-(2, 1-b)-thiazolyl-(2)-acetate were prepared by the respective reaction of p-nitro-α-bromoacetophenone and 2-amino-, 2-amino-4-methyl-, 2-amino-4-methyl-5-β-hydroxyethyl-, 2-amino-4-methyl-5-β-acetoxyethyl- and 2-amino-4-methyl-5-carbethoxy-thiazoles and ethyl 2-amino-4-methylthiazolyl-(5) acetate, in ethanol, acetone or benzene solutions. The nitro groups of these compounds were reduced to corresponding amino groups by reduction with stannous chloride and hydrochloric acid, or with zinc dust and acetic acid, then led to their acetate with acetic anhydride. The present studies were undertaken in connection with a research on chemotherapeutics for tuberculosis.View full abstractDownload PDF (890K) -
Syntheses of Imidazo Compounds. (2)Taizo Matsukawa, Syoichi Ban1951 Volume 71 Issue 7 Pages 760-763
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS2-p-Nitrophenylimidazo-(1, 2-a)-pyridine, 2-p-nitrophenyl-imidazo-(1, 2-a)-pyrimidine, 2-p-nitrophenyl-5-methylimidazo-(1, 2-a)-pyrimidine and 2-p-nitrophenyl-5-methyl-7-hydroxy-imidazo-(1, 2-a)-pyrimidine were prepared by the respective reaction of p-nitro-α-bromoacetophenone with 2-aminopyridine, 2-aminopyrimidine, 2-amino-4-methylpyrimidine and 2-amino-4-methyl-6-hydroxypyrimidine in ethanol solution. The nitro groups in these compounds were reduced with stannous chloride and hydrochloric acid to obtain corresponding amino compounds which were further led to acetates by acetic anhydride.
Condensation products were not obtained in the reaction of p-nitro-α-bromoacetophenone with 2-amino-4-methyl-6-carbethoxy-, 2-amino-4-methyl-5-carbethoxy-, 2-amino-4-methyl-6-chloro-, 2-methyl-4-amino-5-aminomethyl- and 2-methyl-4-amino-5-cyanopyrimidines. These experiments were conducted in connection with studies on chemotherapeutics for tuberculosis.View full abstractDownload PDF (904K) -
Hiroshi Mitsuhashi1951 Volume 71 Issue 7 Pages 764-765
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSantonin was treated with acetic anhydride and a drop of concentrated sulfuric acid to obtain qualitatively l-α-desmotroposantonin acetate. By using the latter, saponification and hydrolysis could be effected simultaneously and the quantitative estimation of santonin was made by measuring the amount of alkali used. By this means, the estimation could be carried out with the same accuracy as by earlier method with one-half the amount of sample.View full abstractDownload PDF (356K) -
Michihiro Hirai, Ryoichi Hayatsu1951 Volume 71 Issue 7 Pages 765-766
Published: July 25, 1951
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA microdetermination of nitrogen using a micro-Kjeldahl apparatus by heating and decomposing 2-3mg. of acid amides with 10cc. of 40% NaOH, and collecting the ammonia that generates in 0.01N-HCl. Error is ±0.5%.View full abstractDownload PDF (304K)
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