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On Higher Alkylsulfates
Isamu Utsumi, Yoshishige Sato, Chikara Kowaki, Kiyoshi Harada
1957 Volume 77 Issue 12 Pages
1259-1264
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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In order to increase the stability, emulsifiability, and dispersibility of main drugs and to decrease their irritant properties, attempts were made to give surface active properties to the main drugs. Higher alkylsulfates of antihistamines like 2-dimethylaminoethyl benzhydryl ether, antimicrobial agents like 2-dimethylamino-6-(2-diethylaminoethoxy) benzothiazole, and local anesthetics like 2-diethylaminoethyl
p-aminobenzoate (procaine) were synthesized and their surface tension was measured. At the same time, emulsification test was carried out and it was found that they had better surface activity than the free bases, hydrochlorides, and other mineral acid salts. It was observed that the surface activity and emulsifiability became the greatest when the number of carbon atoms in the alkyl group of alkylsulfates was around 12-14. A good result was obtained in the emulsification of liquid paraffin and water by the use of laurylsulfate of 2-dimethylaminoethyl benzhydryl ether, with the addition of a minute amount of alkali.
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On Higher Alkyisulfates of Thiamine
Isamu Utsumi, Yoshishige Sato, Nobuo Tanaka, Kiyoshi Harada, Naomasa M ...
1957 Volume 77 Issue 12 Pages
1265-1270
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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As a part of series of studies on the surface activation of medicinals, attempts were made to prepare higher alkylsulfates of thiamine. Exchange reaction between 1 mole of thiamine chloride hydrochloride and 2 moles of higher alkylsulfate or its alkali salt afforded thiamine dialkylsulfate in crystalline state, in a good yield. Thiamine monoalkylsulfate was obtained by the exchange reaction between 1 mole of thiamine chloride and 1 mole of silver alkylsulfate or the partial neutralization of thiamine dialkylsulfate with anion exchange resin in hydrous acetone or hydrous ethanol.
Examination of physicochemical properties of these higher alkylsulfates revealed that the bondage between the amine and higher alkylsulfuric acid is mainly an ionic bond as in the salts. They form a micelle in aqueous solution and indicate a strong surface activity. With increasing number of carbon atoms in the alkyl group, the salts become extremely sparingly soluble in water at room temperature and become soluble in some organic solvents, such as alcohols and chloroform. These alkylsulfates have much less bitterness and characteristic odor than the known salts and were found to have better stability.
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Studies on Higher Alkylsulfonates
Isamu Utsumi, Chikara Kowaki, Tatsunori Baba, Tatsuo Takeuchi
1957 Volume 77 Issue 12 Pages
1271-1275
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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Higher alkylsulfonates of anthelmintic piperazine, antimalarial quinine, amino acids like methionine, glycine, and leucine, antihistaminic 2-dimethylaminoethyl benzhydryl ether, and pyridoxine were prepared and they were found to be the salt of these drugs and higher alkylsulfonic acid. The alkylsulfonic acids used were prepared from corresponding higher alcohols of 10-18 carbon atoms. Examination of the surface chemical properties of these alkylsulfonates showed them to be more stable than their mineral acid salts and to have surface activity like emulsification agents in general, and their application to various preparation may be expected.
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Studies on Antiseptics of Alkyl p-Hydroxybenzoates for Foodstuff. (1). A Method of Preparation of Alkyl p-Hydroxybenzoates and their Monohalogen Derivatives
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1276-1278
Published: December 25, 1957
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p-Hydroxybenzoic acid was esterified with corresponding alcohols in benzene, using conc. sulfuric acid as the dehydration agent, and amyl, hexyl, heptyl, and octyl esters were prepared. Iodination, bromination, and chlorination of
p-hydroxybenzoic acid afforded 3-iodo-, 3-bromo-, and 3-chloro-4-hydroxybenzoic acids and their esterification afforded a total of 24 kinds of methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, and octyl esters of these 3-halo-4-hydroxybenzoic acids.
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Studies on Antiseptics of Alkyl p-Hydroxybenzoates for Foodstuff. (2). Antifungal Action of Alkyl p-Hydroxybenzoates and their Monohalogen Derivatives against Soy Sauce
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1279-1282
Published: December 25, 1957
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Antiseptic action against soy sauce was tested with 32 kinds of esters and their monohalogen derivatives of
p-hydroxybenzoic acid. The results obtained may be summarized as follows.
1) The greatest antiseptic action against soy sauce was shown by hexyl
p-hydroxybenzoate.
2) Increase in antiseptic effect by the introduction of one halogen atom in the
ortho position to the hydroxyl group in
p-hydroxybenzoic esters was found only in lower alkyl esters and the effect was rather found to decrease in higher alkyl esters.
3) Amyl ester of the 3-chloro compound, butyl ester of the 3-bromo compound, and propyl ester of the 3-iodo compound showed the strongest antiseptic action. Maximum effect was found in chloro, bromo, and iodo derivatives with one less methylene group.
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Studies on Antiseptics of Alkyl p-Hydroxybenzoates for Foodstuff. (3). Antibacterial Action and Effect of Alkyl p-Hydroxybenzoates and their Monohalogen Derivatives on the Respiration of
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1282-1285
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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p-Hydroxybenzoic acid esters and their monohalogen derivatives show increasingly strong antibacterial action against
Staphylococcus aureus and
Bacillus subtilis with increasing number of carbon atoms in the alkyl chain constituting the ester. Their action against
Escherichia coli is much weaker than that against Staphylococci and
Bac. subtilis. Introduction of a halogen in the 3-position of these esters was found to increase the antibacterial action against Staphylococci and
Bac. subtilis but not so markedly. This introduction of halogen markedly increases respiratory inhibition in
Escherichia coli and this effect is more marked in the lower members of the ester. The effect also differs according to the halogen atom introduced, the effect decreasing in the order of iodine, bromine, and chlorine.
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Studies on Antiseptics of Alkyl p-Hydroxybenzoates for Foodstuff. (4). Relationship between Physical Properties and Biological Activities of Alkyl p-Hydroxybenzoates and their
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1285-1288
Published: December 25, 1957
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A total of 32 compounds, methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, and octyl
p-hydroxybenzoate and their monochloro, monobromo, and monoiodo derivatives were submitted to tests of their solubility in water and lowering of surface tension in aqueous solution. Relationship between these physical properties and biological activities was also examined. It was thereby found that the biological activity of these compounds can be explained to a certain extent from their lowering of surface tension and solubility in water but a better elucidation can be obtained by the consideration of equilibrium between organic and inorganic properties in these compounds.
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Studies on Antiseptics of Alkyl p-Hydroxybenzoates for Foodstuff. (5). A Few Fundamental Studies on the Respiration of Zygosaccharomyces japonicus
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1288-1292
Published: December 25, 1957
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A few experiments were carried out on the respiration of
Zygosaccharomyces japonicus by the use of Warburg manometer. Oxygen consumption was observed only when glucose was used as a substrate on the neutral side or acetic acid as the substrate on acid side, and no absorption of oxygen was detected with various organic acids in the Krebs cycle. This must be due entirely to the permeability through the cell membrane. Lyophilized preparation of the yeast showed activity of succinic dehydrogenase and the activity was found to be inhibited by malonic acid. Succinic dehydrogenase was extracted from
Zygosaccharomyces japonicus and the activity of this cell-free preparation was not affected by sodium dehydroacetate (1×10
-3M) and sodium dodecylsulf ate (1×10
-4) in minimum concentration completely inhibiting the growth of this yeast, but was inhibited 50% by the same concentration (3×10
-3M) of methyl
p-hydroxybenzoate.
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Studies on Antiseptics of Alkyl p-Hydroxybenzoates for Foodstuff. (6). Effect of Antiseptics on the Respiration of Zygosaccharomyces japonicus
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1292-1297
Published: December 25, 1957
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p-Hydroxybenzoic acid esters and their monohalogen derivatives in general inhibit respiration of
Zygosaccharomyces japonicus when glucose is used as a substrate, and this activity of respiration inhibition is in proportion to their antiseptic activity. The respiration of this yeast, with glucose as a substrate, was also inhibited by compounds having antiseptic action, such as sodium dehydroacetate, vitamin K
3, water-soluble vitamin K
3, sodium dodecylsulfate, phenyl isothiocyanate, allyl isothiocyanate, butyl orsellate, and isoamylresorcinol. Furacin, phenylacetic acid, sodium
p-aminosalicylate, and sodium cetylsulfate did not inhibit respiration with glucose as a substrate and all these compounds were found to have hardly any antiseptic activity. Therefore, antiseptic efficacy against soy sauce could be estimated from respiration inhibition. It was also found that non-dissociating molecule of these
p-hydroxybenzoic acid esters was effective in inhibiting the respiration of this yeast.
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Tatsumi Nakashima
1957 Volume 77 Issue 12 Pages
1298-1302
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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By the Grignard reaction of 2-cyano-pyridine and -quinoline, 2-acetyl-, 2-propionoyl-, and 2-benzoyl-pyridines and -quinolines, and 2-phenylacetylpyridine were synthesized. 2-Phenylacetylquinoline was obtained from ethyl quinaldate through 2-(α-cyanophenylacetyl) quinoline. 2-Phenacyl-pyridine and -quinoline come in four desmotropic forms of (A) C
5H
4N⋅CH
2COC
6H
5 or C
9H
6N⋅CH
2COC
6H
5 and (B) C
5H
4N⋅COCH
2C
6H
5 or C
9H
6N⋅COCH
2C
6H
5. The properties of these four compounds were compared with each product synthesized by the following two routes: (i) 2-Picoline or quinaldine → 2-styrylpyridine or -quinoline → dibromide → 2-(2-phenethinyl) pyridine or -quinoline → 2-phenacylpyridine or -quinoline. (ii) 2-Picoline or quinaldine → 2-picolyllithium or quinaldinyllithium → 2-phenacyl-pyridine or -quinoline. Each of the ketones was derived to the oxime and reaction with Fe
2+ was carried out. The red to reddish violet complex formed with 2-acylpyridine was submitted to absorption spectral measurement to examine the effect of alkyl or aryl group of RCO-in the formation of a complex salt. It was found that C
5H
4N⋅CH
2C(=NOH)C
6H
5 and 2-acylquinolines do not form complex salt with Fe
2+.
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Shigeru Aonuma, Tsutomu Mimura, Masaaki Tarutani
1957 Volume 77 Issue 12 Pages
1303-1307
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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Serum cholesterol level, phospholipid level, and the ratio of total cholesterol to total phospholipid (TC/TP value) are said to be important factors in clarifying the mechanism of atherosclerosis and the degree of its progress. Crude drugs said to be effective for this disease from olden times were examined by oral administration in normal, cholesterol-fed, and thyroidectomized rabbit and variation in TC/TP value was examined. The crude drugs used were coptis, scutellaria, rhubarb, bupleurum, and a preparation (San-wo-gan) containing coptis, scutellaria and rhubarb in 1:1:1 ratio as a digest solution. In the case of normal rabbits, all the crude drugs gave no effect, while all except bupleurum gave a good effect on cholesterol-fed rabbits. Bupleurum was found to increase the TC/TP value. San-wo-gan was found to decrease the heightened TC/TP value in thyroidectomized rabbit.
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Isolation of a New Ester Compound
Tsunematsu Takemoto, Tadashi Nakajima
1957 Volume 77 Issue 12 Pages
1307-1309
Published: December 25, 1957
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A new ester of b. p
6 74-76° was isolated as the essential oil component of
Artemisia annua L. (Compositae) and its hydrolysis afforded acetic acid and a new alcohol compound, C
10H
18O, b.p
6 71° [α]
D20-31.8°,
nD20 1.4640. This alcohol colored yellow with tetranitromethane, decolorized potassium permanganate and bromine, and a presence of two double bonds in its molecule was assumed from its infrared spectrum and molecular refraction.
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Structure of l-β-Artemisia Alcohol
Tsunematsu Takemoto, Tadashi Nakajima
1957 Volume 77 Issue 12 Pages
1310-1313
Published: December 25, 1957
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The alcohol compound obtained by hydrolysis of an ester isolated from
Artemisia annua L. was determined from various experimental evidences as 3, 3, 6-trimethyl-1, 5-heptadien-4-ol (I) and was formally designated as
l-β-artemisia alcohol.
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Antioxidative Effect of Sulfur-containing Fatty Acid on Fats and Oils
Masuo Akagi, Isamu Aoki
1957 Volume 77 Issue 12 Pages
1314-1317
Published: December 25, 1957
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Antioxidation effect was examined with 14 kinds of α-thio derivatives of acetic acid, 4 kinds of α-thio derivatives and 14 kinds of β-thio derivatives of propionic acid, 9 kinds of mercaptal, 4 kinds of thiodifatty acid, and six miscellaneous compounds, with methyl oleate as the substrate.
In general, propionic acid derivatives were better than acetic acid derivatives, and the β-thio derivatives of propionic acid were better than the α-thio derivatives. 3-Alkylthiopropionic acids were all effective, the effect decreasing in the order of butyl, octyl, dodecyl, propyl, and ethyl. None of the thiodifatty acids was effective while mercaptal derivatives of vanillin showed fairly strong effect, This latter effect was heightened by the addition of their synergist, phosphoric acid or ascorbic acid stearate. Vanillalacetone was also a strong antioxidant. The effect of 3-arylthiopropionic acid decreased in the order of 3-methoxy-4-hydroxyphenyl, benzyl,
p-hydroxyphenyl, 3, 4-dimethoxyphenyl, phenyl,
p-tolyl,
p-methoxyphenyl, and
p-methoxypeezyl, and 3-(3-methoxy-4-hydroxyphenylthio)propionic acid was equally effective as the commercial antioxidant. Protocatechualdehyde mercaptal-3, 3-dipropionic acid had stronger effect than commercial antioxidant but its toxicity was stronger, minimum lethal dose in mice being 0.11-0.12g./kg. by subcutaneous injection.
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Colorimetric Determination of Chloramphenicol with Hydroxylamine Hydrochloride and Ferric Chloride
Tsutou Aihara, Hideko Machida, Yuki Yoneda
1957 Volume 77 Issue 12 Pages
1318-1321
Published: December 25, 1957
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Physicochemical method of determining chloramphenicol may be classified into two; one utilizing the nitro radical in its structure and the other of determining dichloro-acetic acid formed by hydrolysis. The former includes ultraviolet and infrared spectral measurements, colorimetry after derivation to azo dye, colorimetry using isonicotinic acid hydrazide, and polarographic method. However, these determinations are interfered in the presence of allied compounds possessing a nitro group. In the determination of dichloroacetic acid, the acid is derived to a fluorescent substance and its fluorescent intensity is measured.
The method reported in the present paper is to derive the acid amide in the chloramphenicol molecule to hydroxamic acid by the use of alkali and hydroxylamine hydrochloride, to derive to complex salt with ferric chloride, and colorimetric determination of the color thereby produced. Since the decomposition product of chloramphenicol is usually a base formed by the cleavage of the acid amide linkage, the present method is suitable for the determination of foods changed by long storage and the result obtained agreed with that by bioassay.
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Separatory Determination of Chloramphenicol by Paper Electrophoresis
Tsutou Aihara, Kazuo Sato
1957 Volume 77 Issue 12 Pages
1322-1323
Published: December 25, 1957
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Separatory determination of chloramphenicol and its decomposition product was performed by isolating chloramphenicol by paper electrophoresis and determining it by ultraviolet absorption sptectrum. The result of separatory determination of the acid or alkali hydrolyzate of chloramphenicol and photodecomposition product agreed well with the values obtained by microbiological assay.
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Inhibitory Effect of 2-Methyl-4-amino-5-hydroxymethylpyrimidine on the Growth of Lactic Acid Bacteria and its Reversal by various Vitamins
Eiichi Hiraoka
1957 Volume 77 Issue 12 Pages
1324-1327
Published: December 25, 1957
Released on J-STAGE: February 19, 2010
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In order to examine the effect of antipyridoxine substances on microörganisms, growth inhibition by 2-methyl-4-amino-5-hydroxymethylpyrimidine (OMP) of five kinds of Lactobacteriaceae,
Lactobacillus arabinosus,
L. casei,
L. fermenti,
Leuconostoc mesenteroides, and
Streptococcus faecalis, was examined in a vitamin-deficient medium containing a minimum amount of requisite vitamins. With the exception of
L. arabinosus, growth of all four organisms of Lactobactriaceae was inhibited by OMP in concentrations above 10-100γ/tube. Recovery of growth inhibition was examined by adding various kinds of vitamins with OMP and it was found that only the pyridoxine group vitamins exhibited specific antagonism against OMP. Such observations agree with the results obtained so far with mice, rats, and yeast. It was considered that the reason why
L. arabinosus growth was not inhibited by OMP is because this bacillus can biosynthesize pyridoxine.
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Inhibitory Effect of 2-Methyl-4-amino-5-hydroxymethylpyrimidine Analogs on the Growth of Lactic Acid Bacteria and their Reversal by various Vitamins
Eiichi Hiraoka
1957 Volume 77 Issue 12 Pages
1328-1330
Published: December 25, 1957
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Growth inhibition of five kinds of organism of Lactobacteriaceae by 11 kinds compounds structurally related to 2-methyl-4-amino-5-hydroxymethylpyrimidine (OMP) was examined in vitamin-deficient medium. 2-Methyl-4-amino-5-bromome-thylpyrimidine (BMP) showed about the same inhibition as that of OMP but other allied compounds had little or no inhibitory activity. Recovery of BMP inhibition by various vitamins also showed that BMP, the same as OMP, was specifically antagonistic only with thepyridoxine group.
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Inhibitory Effect of Isonicotinohydrazide and 4-Deoxypyridoxine on the Growth of Lactic Acid Bacteria and their Reversal by various Vitamins
Eiichi Hiraoka
1957 Volume 77 Issue 12 Pages
1331-1332
Published: December 25, 1957
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Through the growth inhibition of organisms of Lactobacteriaceae, whether INAH and 4-deoxypyridoxine are antipyridoxine substance or not was examined. When vitamin-deficient medium was used, 1mg./tube of INAH showed marked inhibition of growth which was recovered by the pyridoxine group vitamins. This indicates also that INAH is an antipyridoxine substance. Since 4-deoxypyridoxine failed to inhibit the growth of the organisms of Lactobacteriaceae, its antipyridoxine activity could not be detected.
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Reversal of the Inhibition of the Growth of Lactic Acid Bacteria by Atoxopyrimidines
Eiichi Hiraoka
1957 Volume 77 Issue 12 Pages
1333-1335
Published: December 25, 1957
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It has been reported that compounds structurally related to 2-methyl-4-amino-5-hydroxymethylpyrimidine (OMP) are antagonistic to OMP against spasms in mice. According to experiments in growth inhibition of organisms of Lactobacteriaceae, using vitamin-deficient medium, such substances as 2-methyl-4-amino-5-aminomethyl-, 2-methyl-4-hydroxy-5-hydroxymethyl-, and 2-methyl-4-hydroxy-5-amino-methylpyrimidine were not antagonistic to OMP. 2-Methyl-4-hydroxy-5-aminomethylpyrimidine showed a slight antagonism against
St. faecalis in 1mg./tube amount but from its weaker recovery and larger amount needed in comparison with antagonism by 1γ/tube of pyridoxine, it could not be considered as the antagonist of OMP.
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A Comparison of the Growth Recovering Activity of Vitamin B6 Groups on Lactic Acid Bacteria
Eiichi Hiraoka
1957 Volume 77 Issue 12 Pages
1335-1338
Published: December 25, 1957
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Since the growth inhibition of organisms of Lactobacteriaceae by OMP, BMP, and INAH was found to be specifically recovered by the pyridoxine group vitamins, their inhibition index was examined. With the same bacillus, recovery of inhibition was of the same order with pyridoxine, pyridoxal, and pyridoxamine, even if the inhibitor was different. The recovery became weaker in the order of pyridoxal, pyridoxamine, and pyridoxine for
L. casei, and in the order of pyridoxamine, pyridoxal, and pyridoxine for
St. faecalis and
L. arabinosus, these orders being the same as their vitamin activity for these bacilli. The degree of growth inhibition by OMP against these bacilli is the same whether estimated by turbidity or by the amount of the acid formed. From these results, it is considered that OMP inhibits enzymes taking part in amino acid metabolism rather than the glycolytic enzyme system.
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Discussion on the Structure of Artemisia Ketone
Tsunematsu Takemoto, Tadashi Nakajima
1957 Volume 77 Issue 12 Pages
1339-1344
Published: December 25, 1957
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The structure of artemisia ketone had heretofore been represented as 2, 5, 5-trimethyl-1, 6-heptadien-4-one (I), shown in Chart 1, but this was corrected to 2, 5, 5-trimethyl-2, 6-heptadien-4-one (II), as shown in Chart 2. All the reactions could be explained rationally by denying the existence of an isoartemisia-ketone.
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On Dihydroartemisia Ketone
Tsunematsu Takemoto, Tadashi Nakajima
1957 Volume 77 Issue 12 Pages
1344-1347
Published: December 25, 1957
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Hydrogenation of artemisia ketone with platinum oxide in methanol afforded dihydroartemisia ketone which was determined as 2, 5, 5-trimethyl-2-hepten-4-one (II) from the reaction system shown in Chart 1 and from its infrared and ultraviolet spectra (Figs. 1 and 2).
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Acetylation and Nitration of Pyrrocoline
Yoshio Arata, Susumu Sakamoto, Sachiko Morosumi, Ryoji Ito
1957 Volume 77 Issue 12 Pages
1347-1349
Published: December 25, 1957
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The diacetylpyrrocoline (A), obtained by heating pyrrocoline (V) with acetic anhydride, is oxidized by hydrogen peroxide to 2-picolinic acid 1-oxide. The diacetyl compound, derived from 2-pyrrocolinecarboxylic acid (I) by acetylation and decarboxylation, is identical with (A), from which it was clarified that (A) is 1, 3-diacetylpyrrocoline. On the other hand, nitration of pyrrocoline (V) with nitric acid gives a dinitropyrrocoline (VI) whose oxidation with hydrogen peroxide similarly gives 2-picolinic acid 1-oxide. (VI) was found to be identical with 1, 3-dinitropyrrocoline (VIII) obtained by the nitration of 1, 3-diacetyl-2-pyrrocolinecarboxylic acid (III) followed by decarboxylation.
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Disappearance of Inhibitiory Action of a Few Anticeptics on the Respiration of Zygosaccharomyces japonicus by Washing
Kunio Hirai
1957 Volume 77 Issue 12 Pages
1350-1351
Published: December 25, 1957
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Treatment of
Zygosaccharomyces japonicus with methyl
p-hydroxybenzoate, sodium dehydroacetate, and sodium dodecylsulfate, in respective concentrations of 1.25×10
-2 M, 5×10
-2 M, and 1.5×10
-3 M, that effect 100% inhibition of respiration in glucose medium, and subsequent washing was found to restore respiration to 80%. It was therefore concluded that the chemical did not penetrate into the cell but was adsorbed on the cell surface, inhibiting the consumption of glucose.
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Yukio Kameda, Etsuko Toyoura, Yukio Kimura, Katsuhiko Matsui, Tomoo Om ...
1957 Volume 77 Issue 12 Pages
1351-1352
Published: December 25, 1957
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The acetone-dried powder of Ehrlich's ascites carcinoma was able to hydrolyze dichloroacetyl-DL-aspartic acid but not the dichloroacetyl derivatives of the following 17 amino acids: Glycine, DL-alanine, DL-α-aminobutyric acid, DL-valine, DL-leucine, DL-phenylalanine, DL-tyrosine, DL-serine, DL-threonine, DL-glutamic acid, ε-benzoyl-DL-lysine, DL-methionine,
erythro-β-phenyl-DL-serine,
threo-β-phenyl-DL-serine,
erythro-β-
p-nitrophenyl-DL-serine,
threo-β-
p-nitrophenyl-DL-serine, and DL-phenylglycine.
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Tatsuji Mazaki, Masakazu Aritomi
1957 Volume 77 Issue 12 Pages
1353-1354
Published: December 25, 1957
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Epifriedelanol (plates, m. p. 282-284°) in ca. 0.3%, and friedelin (needles, m. p. 256-259°) in ca. 0.02% were isolated and identified from dried leaves of
Euonymus alata SIEB., besides quercetin, m. p. 304°, in ca. 0.1%, and dulcitol, m. p. 189°, in ca. 1.1% yield.
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Tatsuji Mazaki, Masakazu Aritomi
1957 Volume 77 Issue 12 Pages
1354-1355
Published: December 25, 1957
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Examinations were made for triterpenes in the acetone extract of the leaves of
Euonymus alata SIEB. forma
Striata MAKINO (Celastraceae family) and epifriedelanol (plates, m. p. 283-284°) was isolated in ca. 0.42% yield and identified.
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On the Emancipation of 1, 8-Cineole Oxide Ring
Isao Ogura, Ai Nakanishi, Masae Yanagida, Naoko Inoue
1957 Volume 77 Issue 12 Pages
1355-1357
Published: December 25, 1957
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It is known that an oxide ring is labile in acidity and the oxide ring of 1, 8-cineole easily undergoes cleavage by acid treatment to form terpin or terpineol. The acidity at which the cleavage occurs was examined by preparing sulfuric acid solutions of pH 1-5. A mixture of 20cc. of the sulfuric acid solution and 20cc. of cineole was reacted in a three-necked flask of 200-cc capacity, in a water bath and a thermostat of 50°, with stirring. The mixtures of pH 1 and 2 were reacted for 16 hours at 2-hours intervals, and those of pH 3-5 at 3-hours intervals. The amount of changed cineole was calculated from the melting point of cre-cineole. The amount of cineole changed was greater, the higher the temperature and longer the reaction time and the amount decreased in a curve and not in a straight line. Iodine value was also found to increase with the decrease of cineole.
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Keijiro Takagi, Hideomi Fukuda, Kokuji Yano
1957 Volume 77 Issue 12 Pages
1358
Published: December 25, 1957
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1957 Volume 77 Issue 12 Pages
e5aa
Published: 1957
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1957 Volume 77 Issue 12 Pages
e5ab
Published: 1957
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1957 Volume 77 Issue 12 Pages
e5ac
Published: 1957
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1957 Volume 77 Issue 12 Pages
e5ad
Published: 1957
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
-
1957 Volume 77 Issue 12 Pages
e5ae
Published: 1957
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
-
1957 Volume 77 Issue 12 Pages
e5af
Published: 1957
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
-
1957 Volume 77 Issue 12 Pages
e5ag
Published: 1957
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS
-
1957 Volume 77 Issue 12 Pages
e5b-e6
Published: 1957
Released on J-STAGE: February 19, 2010
JOURNAL
FREE ACCESS