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KATSUHIDE MATOBA, TAKAO YAMAZAKI
1972 Volume 92 Issue 3 Pages
213-220
Published: March 25, 1972
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3-Methoxy-4-hydroxy-5-methyl-2-cyclopentenone (VI), a good model for five-membered vinylogous ester of acutumine (I), was reduced with lithium aluminum hydride, to 4-methyl-5-hydroxy-2-cyclopentenone (X), 2-methyl-4-cyclopentene-1, 3-diol (XI
(VI)) and 2-methyl-cyclopentane-1, 3-diol (XII
(VI)). 3-Methoxy-4-methyl-5-hydroxy-2-cyclopentenone (VII) was reduced to 4-hydroxy-5-methyl-2-cyclopentenone (XIII). The revised mechanism was proposed and the errors in the previous papers based on ambiguous experimental data were corrected.
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MASAYOSHI KOBAYASHI, TAKEO MORIMOTO, MASAAKI YAMAMOTO
1972 Volume 92 Issue 3 Pages
221-225
Published: March 25, 1972
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Presence of a substance inhibiting gastric secretion in salivary glands, which may be considered as the secretory source of sialogastrone (the substance in the saliva, inhibiting gastric secretion) was studied in comparison with other organs. Submaxillary glands and other organs of mice, rats, rabbits, and dogs were used as material and their aqueous extract was assayed for the gastric secretion inhibiting activity. Simultaneously, the difference from pyrogenic substance, which also exhibits similar gastric secretion inhibiting activity, was clarified. First, the gastric secretion inhibitory activity (G) and pyrogenic activity (P) of the pyrogenic substance (X-3) extracted from the saliva were assayed and the ratio G/P of the antisecretory activity to pyrogenic activity was calculated. The result of the assay showed that the ratio did not change in the presence of an inert protein. Therefore, the specificity of antisecretory activity of the extract fractions was judgeb from the ratio of G/P. Aqueous extracts from various organs were fractionated by gel filtrations on Sephadex G-100. The antisecretory activities of the total 253 fractions so obtained were assayed. The specific activity was found only in two fractions obtained from the submaxillary glands of mice, although the activity was also found in six fractions obtained from the stomach, pancreas, kidney, and spleen of mice and rats. However, the latter fractions could not be judged as the specific activity from the ratio of G/P, because of not being distinguishable from the antisecretory activity of mixed pyrogenic substances, and all the remaining fractions did not exhibit any antisecretory activity or did exhibit enhanced pyrogenic activity.
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MASAYOSHI KOBAYASHI, MASAAKI YAMAMOTO
1972 Volume 92 Issue 3 Pages
226-231
Published: March 25, 1972
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Since a specific inhibitory activity against gastric secretion was found in the submaxillary glands of mice, an attempt was made to extract and purify the active substance. An aqueous extract of the submaxillary glands of adult male mice was purified by a successive process in the order of gel filtration on Sephadex G-100, column chromatography on DEAE-cellulose, and a second gel filtration on Sephadex G-100. This process resulted in a higher purified fraction (Frac. 4B), which exhibited an enhanced activity 100 times that of the crude extract. This fraction was still proved to contain a small amount of contamination by electrophoresis, but the activities of protease, histaminase, and kallikrein werenegligible. However, this fraction showed esterase activity 3.2 times that of trypsin. The antisecretory activity was lost by proteolysis or heat treatment. The active substance was assumed to be a protein having a molecular weight of about 50000 from the result of gel filtration. In the antisecretory activity of the active substance obtained from the submaxillary galnds, definite sexual dimorphism like the case of nerve growth factor (NGF) and esterase was not recognized.
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YOSHINOBU AKADA, HIDETAKA YUKI, KIYOSHI TAKIURA
1972 Volume 92 Issue 3 Pages
232-237
Published: March 25, 1972
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Cinnamic acid derivatives and molar ratios of componental monosaccharides contained in the four purified senega saponins, S-A, S-B, S-C, and S-D isolated from Senegae radix (Polygala senega LINNE var. latifolia TORRY et GRAY, Polygalaceae), were investigated. 4-Methoxy- and 3, 4-dimethoxy-cinnamic acids were detected in S-A and S-B (molar ratio, 1 : 1). 4-Methoxycinnamic acid was also detected in S-C, but not 3, 4-dimethoxycinnamic acid. Cinnamic acid derivative was not found in S-D. The molar ratios of rhamnose, fucose, xylose, glucose, and galactose were 2 : 1 : 1 : 2 : 2 in S-A, S-B and S-D, and 3 : 1 : 1 : 2 : 2 in S-C. Mild acid hydrolysis of the crude saponin gave six kinds of oligosaccharides, xyl-rham*, gal-xyl*, gal-glu*, (glu, gal)-xyl*, (xyl, rham)-fuc*, (gal, xyl, rham, fuc)-glu*, in addition to the above-mentioned monosaccharides, were detected. (The asterisk indicates the termi nal, reducing portion.)
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TETSUJI KAMETANI, KIYOSATO NYU, ISAO NOGUCHI, MASATAKA IHARA
1972 Volume 92 Issue 3 Pages
238-240
Published: March 25, 1972
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Several aryl esters (XIV, XVa-c, and XVI), which were expected as a hypotensive agent, were synthesized by the Schotten-Baumann reaction of 2, 3-dimethoxy-11-hydroxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (VII) with the corresponding acid chlorides.
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OSAMU OHODAIRA, NAOHIRO YOSHITANI, FUMIKO SAGARA
1972 Volume 92 Issue 3 Pages
241-249
Published: March 25, 1972
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Regression analyses (stepwise procedure) were carried out using a FACOM 270-20/30 computer on the working porosity and the coefficient of weight variation of strip-packages. The results showed that 85% of the variance in the working porosity could be accounted for by the factors μi/k, α, and S, and that 79% of the variance in the coefficient of weight variation could be accounted for by the factors D
p/D
die and S. In addition, the results of analysis of variance (ANOVA) showed that the overall variance in weight variation might be reduced to acceptable values by minimizing the volume difference among dies, and by sifting off the cohesive fines. The effect of glidants on the reduction of die wall friction was evaluated by the regression equation, which gave estimated values for the working porosity and the coefficient of weight variation of the modified particles.
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TADASHI FUJITA
1972 Volume 92 Issue 3 Pages
250-256
Published: March 25, 1972
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1) In vitro experiment was made to clarify the interrelationship among lipid peroxidation, lipid compositions, and cytochrome oxidase activity in rat liver mitochondria. 2) Ascorbic acid and metal ions (Fe
2+, Fe
3+, Cu
2+) catalysed lipid peroxidation in mitochondria, but Ca
2+ inhibited it. 3) Combined application of ascorbic acid with Fe
2+ (or Fe
3+) markedly, increased the formation of lipid peroxide in mitochondria but that of ascorbic acid with Ca
2+ or Cu
2+ did not. 4) Linoleic acid and LAHPO did not affect the peroxidation process in liver mitochondria, in vivo or in vitro. 5) Lipid peroxidation in vitro promoted by ascorbic acid and Fe
2+ was accompanied by the decrease of cytochrome oxidase activity and unsaturated fatty acid (C
18 : 2, C
20 : 4, C
22 : 6) content of mitochondria. Among the fatty acid compositions of phosphatidylserine and phosphatidylinositol, diminution of linoleic acid and arachidonic acid was predominant. 6) Relationship among lipid compositions, lipid peroxidation, and cytochrome oxidase activity in rat liver mitochndria was discussed.
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YURIKO KATO, TSUNEKO OHUCHI
1972 Volume 92 Issue 3 Pages
257-263
Published: March 25, 1972
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Solubility of phenobarbital, salicylic acid, and caffeine in a mixture of 12 kinds of solubilizing agent and water was measured, and the relationship between the solubility and dielectric constant was examined. In a mixed solvent of water and ethylene glycol, diethylene glycol, or triethylene glycol, possessing only a hydrophilic group, a plot of dielectric constant against the logarithm of solubility expressed by molar fraction gave a straight line, and it would be difficult to consider that these solubilizing agents undergo association in the mixed solvent. In contrast, in the mixed solvent of water and cellosolve, carbitol, dipropylene glycol, methylcarbitol, or 1-methoxy-2-propanol, which possess both hydrophobic and hydrophilic groups, the same plot gave one flexion in the straight line, indicating that these solubilizing agents undergo association at a specific concentration, some kind of a sudden change occurs in the internal structure of the mixed solvent, and a change in the solubility of phenobarbital and salicylic acid occurs at this concentration, and a maximum solubility in caffeine. Further, in the mixed solvent of water and butylcellosolve, butylcarbitol, hexylene glycol, or isopropylcellosolve, there were two flexions in the straight line, suggesting that these solubilizing agents undergo stronger association.
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ITSUO MORI
1972 Volume 92 Issue 3 Pages
264-269
Published: March 25, 1972
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Spectrophotometric determination of thorium (IV), zirconium (IV), and fluorine ion was carried out using 3, 4, 5, 6-tetrachloro 3', 4', 5', 6'-tetrahydroxyfluoran methyl ester as the reagent. To a solution containing thorium (IV) and zirconium (IV), 1.0ml of 5.0×10
-2M F
- solution, 1.5 ml of 1.0×10
-2M cetylpyridinium chloride solution, 2.0ml of acetic acid-sodium acetate solution of pH 4.6, and 1.5-2.0ml of 1.0×10
-3M 3, 4, 5, 6-tetrachloro 3', 4', 5', 6'-tetrahydroxyfluoran methyl ester (Cl-gall-CH
3) solution were added and the whole volume was brought to 10.0ml with water. The absorbance of this solution was measured at 590 and 660 nm and the amount of zirconium (IV) was calculated from the calibration curve for zirconium (IV) prepared with the same solution in which thorium (IV) was masked by F
-. Another calibration curve for thorium (IV) was prepared by the same procedure as above, in the presence of zirconium (IV), and the amount of thorium (IV) was calculated from the absorption of Cl-gall-CH
3-thorium (IV) complex and -zirconium (IV) complex colored by the same procedure as above except for exclusion of F
-. Discoloration of 2.5×10
-5M thorium (IV)- or zirconium (IV)-Cl-gall-CH
3 complex and increase in their absorption by F
- were determined by measuring the absorption of their solution at 660 nm to calculate the amount of F
- in the range of 0-6.5 and 0.6-6.5 μg, respectively.
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JUTARO OKADA, YOSHIHISA MATSUDA, YOSHINOBU FUKUMORI
1972 Volume 92 Issue 3 Pages
270-274
Published: March 25, 1972
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Micro-mixing of potato starch and sodium hydrogencarbonate under a very high dilution ratio (2500-100000) has been studied using the radioactive tracer technique. In the present work, potato starch as a model of potent drug was combined with radioactive iodine
125I (Elementary in ethanol, γe=35 keV, T1/2=60.0 d, 3.0mCi). Under such a dilution ratio, the theoretical sample variance of fully random mixing obtained from Stange's equation (1) can be derived to equation (2') and this suggests that the state of fully random mixing does not depend on the particle size characteristics of diluent. The result of mixing using two size ranges (-150+250, -250 mesh) of diluent followed the tendency expected from eqaution (2') and these were supported by the statistical test. The uniformity of variance of 6 batches of mixing in each dilution ratio was tested and the stability of the state of mixing at the given operation condition was confirmed.
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SEIJU KUBOTA, OSAMU KIRINO, YOSHIYUKI KOIDA, KEISHIRO MIYAKE
1972 Volume 92 Issue 3 Pages
275-277
Published: March 25, 1972
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Reaction of 2-cyanopyridine with hydrazine was examined using picolinic acid amidrazone (IV) which is an intermediate of this reaction. When the ethanol solution of IV was heated under reflux in nitrogen atmosphere, 3, 6-di (2-pyridyl)-1, 2-dihydro-1, 2, 4, 5-tetrazine (I) and 1, 2-bis (pyridine-2-formimidoyl) hydrazine (III) were obtained. The quantitative study of the reaction suggested that I was not formed via III but they were produced simultaneously. Application of oxygen during refluxing of ethanol solution of IV gave I, III, 3, 6-di (2-pyridyl)-1, 2, 4, 5-tetrazine (V) and 2-pyridinecarboxaldehyde pyridine-2-forminidoylhydrazone (VI).
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SHIGEO UKAI, KAZUO HIROSE, TAKUYA HATTORI, MASATOSHI KAYANO, CHIYOKO Y ...
1972 Volume 92 Issue 3 Pages
278-283
Published: March 25, 1972
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The reaction of chalcone oxide (I) with arylthiol in the presence of triethylamine, or with alkylthiol in the presence of sodium ethoxide, progressed easily to afford aryl or alkyl phenacyl sulfide and benzaldehyde. Similarly 4'-substituted (OCH
3, CH
3, Cl, NO
2) chalcone oxides (II, III, IV, V) reacted with thiophenol in the presence of triethylamine to give the corresponding phenyl 4-substituted phenacyl sulfide and benzaldehyde. 4-Substituted (OCH
3, CH
3, Cl, NO
2) chalcone oxide (VI, VII, VIII, IX) reacted with thiophenol under the same condition to afford phenyl phenacyl sulfide and the corresponding aromatic aldehyde, while, in the case of VIII or IX, additional to give 1-aryl-1-hydroxy 2-phenylthio-3-phenyl-3-propanone (X or XII) as an adduct. The adduct (X or XII) underwent gradual breakdown to phenyl phenacyl sulfide and aromatic aldehyde (p-Cl, p-NO
2) in the presence of thiophenol and triethylamine. This fact indicates that an intermediate like X or XII is first formed by the addition of thiols to chalcone oxides and then the intermediate breaks down to the above two components.
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SUEO HISADA, KOICHI SHIRAISHI, ISAO INAGAKI
1972 Volume 92 Issue 3 Pages
284-287
Published: March 25, 1972
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Four phloroglucinol derivatives were isolated from Dryopteris polylepis (FR. et SAV.) C. CHR. (Aspidiaceae). One of them was identified as flavaspidic acid AB, which was found to be a major compound. This is the first time that it was isolated as crystals from a natural source. The other phloroglucinol derivatives were identified as albaspidin BB, filixic acid BBB, and dryocrassin.
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MIYOSHI HIRATA, SUMIRO ISODA, MUNEFUMI KANAO, HIROYA SHIMIZU
1972 Volume 92 Issue 3 Pages
288-298
Published: March 25, 1972
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A series of 5-halogenopyrimidinylsulfanilamides (I), possessing methyl, alkoxy, and/or alkylthio groups in the pyrimidine ring, were prepared from the corresponding N
4-acetyl derivatives (II) by alkaline hydrolysis. Most of II were prepared from N
4-acetyl-pyrimidinylsulfanilamide derivatives by halogenation with NBS or NCS, and the effect of substituents in the pyrimidine ring upon the halogenation reaction was clarified.
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MICHIO NAKANISHI, YASUYUKI KATO, NORIYUKI ARIMA
1972 Volume 92 Issue 3 Pages
299-304
Published: March 25, 1972
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The urinary metabolites of 1-tert-butylamino-3-[o-(tetrahydrofurfuryloxy) phenoxy]-2-propanol hydrochloride (Y-6124) in rats were investigated by a radiochemical method, thin-layer chromatography (TLC), mass spectrometry, and column chromatography using Amberlite XAD-2 resin. When
3H-labeled Y-6124 was orally administered, 84% of
3H counts in the 24 hr urine was adsorbed by Amberlite XAD-2 resin, which was follwed by quantitative eluation with methanol. Two metabolites (I, II) were detected in the methanol eluate by TLC. These (I and II) were hydrolyzed with β-glucuronidase to the corresponding aglycones III and IV, respectively. Further, treatment of compound IV with acid afforded compound V, which was easily reverted to IV under an alkaline condition. Compound III, which was the aglycone of metabolite I, was discovered to be a monohydroxylated derivative of Y-6124 by mass spectrometry and color reactions. On the other hand, compound V, which was derived from the aglycone (IV) of metabolite II, was found to be a monohydroxylated derivative of 1-tert-butylamino-3-[o-(5-oxotetrahydrofurfuryloxy)-phenoxy]-2-propanol by the above mentioned methods. Therefore, compound IV, the aglycone of metabolite II, was considered to be a monohydroxylated derivative of 3-hydroxy-4-[o-3 (tert-butylamino-2-hydroxypropoxy) phenoxy] pentanoic acid.
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YOSHIO IIZUKA, KEIICHI MATSUDA, KIICHIRO TANAKA
1972 Volume 92 Issue 3 Pages
305-310
Published: March 25, 1972
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Some pharmacokinetic studies were made on bimetopyrol [2-methyl-4, 5-bis (p-methoxyphenyl) pyrrole], a new anti-inflammatory compound, with special reference to the possible quantitative relationship between serum or tissue concentration of this compound and the anti-inflammatory response in rats. Inhibitory effect of bimetopyrol on carrageenininduced rat paw edema was much more efficient by subcutaneous administration into the inflamed paw than by oral medication. On the other hand, the oral activity of bimetopyrol was not affected by adrenalectomy of the animals used. These findings suggest the possibility that bimetopyrol itself and not the metabolites might act directly upon the target at the site of inflamed tissue, even when it was administered orally. In order to prove this hypothesis, rats were at first pretreated with
14C-labeled bimetopyrol orally followed by carrageenin injection in the paw, then both anti-edema activity and content of bimetopyrol in the inflamed paw were estimated. The results summarized below seem to support the hypothesis. (1) Bimetopyrol content (by fluorometry) in the paw was agreed fairly well with that of radioactivity. (2) Either with any dose or with any pretreatment time, the change in bimetopyrol content in the inflamed paw was always parallel to that in percentage inhibition of paw edema.
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YOSHIO IIZUKA, KAZU KOBAYASHI, KIICHIRO TANAKA
1972 Volume 92 Issue 3 Pages
311-315
Published: March 25, 1972
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Bimetopyrol [2-methyl-4, 5-bis (p-methoxyphenyl) pyrrole], a new non-steroidal antiinflammatory drug, was demonstrated to have a stabilizing effect on lysosomes from rat liver. The drug at the concentration between 1×10
-5 and 3×10
-4M suppressed release of acid phosphatase from the heavy lysosome-rich fraction in neutral buffer-sucrose medium at 37°. In acid medium, however, the drug increased the enzyme release similarly as other non-steroidal anti-inflammatory drugs. The acid phosphatase activity was not affected by bimetopyrol itself under the experimental conditions employed. Some experimental conditions required for the demonstration of drug activity on lysosomal membrane were discussed.
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HIKARU OZAWA, TAKESHI ONODERA, IKUKO NAKAMURA
1972 Volume 92 Issue 3 Pages
316-321
Published: March 25, 1972
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In order to examine the interaction of sex hormones in cholesterol metabolism, testosterone, progesterone, or Furazabol was injected subcutaneously in mice and rats before three consecutive treatments with estrone and one of these steroids with estrone was injected intramuscularly for 10 days in chicks. Chloesterol and other lipids in serum and liver were determined. In mice, hypocholesteremic response to estrone was moderately inhibited by testosterone and progesterone but not significantly influenced by Furazabol. In rats, hypocholesteremia induced by estrone was inhibited by testosterone only when the animals were castrated or fed on cholesterol. Their response to estrone was not affected by progesterone but seemed to be potentiated by Furazabol. In chicks, their hypercholesteremic response to estrone was more or less weakened by testosterone and progesterone but hardly affected by Furazabol. Phospholipid and triglyceride were significantly increased in the liver of chicks treated with estrone. Phospholipid was augmented by the three hormones to the same extent but triglyceride was inhibited only by testosterone. It was concluded from these results that testosterone and progesterone tend to inhibit the cholesterol-shifting response to estrone while Furazabol has a comparatively weak effect.
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YUZO MIZUKAMI, TSUKINAKA YAMANA
1972 Volume 92 Issue 3 Pages
322-327
Published: March 25, 1972
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Difference in the intermediates formed in the degradation of chlorothiazide (I), which was hydrolyzed ultimately to 5-chloro-2, 4-disulfamoylaniline (IV) via N-(2-amino-4-chloro-5-sulfamoylphenylsulfonyl) formamide (II) in an alkaline medium and via 5-chloro-2, 4-disulfamoylformanilide (III) in an acidic medium, was investigated using a molecular orbital method, in order to understand the hydrolysis mechanism of I. The hydrolysis pathway of I can be explained by the electronegativity of the atoms involved in the postulated activated-complex, 3-hydroxyhydrochlorothiazide (V). However, the stabilities of II and III in acidic and basic media are a possible reason for the above phenomenon, because there is little difference in electronegativities between the positions 2 and 3 in V and the same positions in the anion type of V, namely V
-.
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KIYOKAZU TAKAISHI, MITSUGU UEHARA, YOSHIKO WATANABE
1972 Volume 92 Issue 3 Pages
328-332
Published: March 25, 1972
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An improvement in the apparatus, which is able to determinate 10
-6 mole of essential oil in a few milligrams of a sample, has been established. The apparatus is suitable for the analysis of essential oils, especially of the essential oils solid at room temperature and heavy density essential oils, using a small portion (0.1-1 g) of crude drugs and plant tissues. The method is applied for the analysis of drugs containing essential oils, perfume, flavour, and cosmetics, and essential oils in the decoction of Chinese medicines.
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TAKEO UEDA, ATSUSHI TAKADA, KUNISHIGE KOSUGI
1972 Volume 92 Issue 3 Pages
332-334
Published: March 25, 1972
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Coloration reaction of potassium 1, 2-naphthoquinone-2-semicarbazone-4-sulfonate (I) with various metal ions was examined, and Bi
3+ was found to show specific coloration in 0.05N nitric acid. The limit of detection of Bi
3+ was found to be 4.5μg/ml of Bi
3+ in 0.05N nitric acid. Determination of Bi
3+ by I within 133μg and 16.5μg was found to be possible by the measurement of the absorbance at 515nm.
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SADAO BESSHO, SUIICHI TOMIOKA, SHIRO ITO
1972 Volume 92 Issue 3 Pages
335-342
Published: March 25, 1972
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In order to clarify the distribution of stress and density inside the compressed powderlike material layer during compression, which has not hitherto been discussed, theoretical discussions were made on one-sided compression without torsion by the most simple circular disc-type flat punch, when only the direction of compression was taken up as the primary problem, pointing out that the Euler's and Lagrange's views should be discriminated, and when compression surface of the moving upper punch was taken as standard. It was also pointed out that many of the empirical compression formula presented to date are the apparent compression state equation and not the compression state equation in the true sense. Some example comparatively close to that equation in the true sense was discussed. A theoretical example was presented for analyzing data on one-dimensional pressure distribution and pressure transfer rate.
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SADAO BESSHO, SUIICHI TOMIOKA, SHIRO ITO
1972 Volume 92 Issue 3 Pages
343-348
Published: March 25, 1972
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Theories concerning the three-dimensional stress distribution and density distribution within the compressed powder-like material layer are generally very difficult to solve but, in the case of one-sided compression without twisting by the disc-type flat punch, approximate elucidation can be obtained by the introduction of experimental data and some hypotheses. As an example, a solution for calculating the stress distribution and density distribution is given for each of the compressed state equations for powder-like material Considering the experimental fact that, in one-sided compression without twisting by the disc-type flat punch, powder-like material inside the compressed layer do not move in the direction of radius and circumference, or their movement can be neglected, their movement can be approximated as deformation in the direction of compression, and assumption of linear approximation in γ-direction and exponential approximation in % direction, gives approximate solution by taking initial and boundary conditions into consideration. The assumptions introduced were examined for their appropriateness based on experimental results obtained in past studies.
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SADAO BESSHO, SUIICHI TOMIOKA, SHIRO ITO
1972 Volume 92 Issue 3 Pages
349-355
Published: March 25, 1972
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In the absence of theoretical and experimental reports on the energy of compression of powder-like materials, considerations were made on powder-like materials as macroscopic continuous body, and an energy equation (1) was discussed by the powder kinetic technique, applying the law of conservation of energy. Detailed examinations were made on the energy equation, introducing concepts like equations (4), (13), and (17). The energy equation (16) obtained finally was reduced to the dimensionless term to obtain equation (22), and analytically shown that the dimensionless term with respect to energy in the compression of powder-like materials is the pressure number equation (27). Physical significance of the pressure number was considered and its content was indicated as equations (33) and (35). Further, considerations were made on the compression of two kinds of powder-like materials, which had gemetrically similar border surface, and apparent similarity equation (31) with respect to energy in the compression of powder-like materials was analytically obtained. As an example of the apparent similarity law with respect to energy in the compression of powder-like materials, a method for calculating the power required was shown.
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CHIYUKI YAMATO, TAKESHI FUJITA, NAOHISA KAWASAKI
1972 Volume 92 Issue 3 Pages
356-358
Published: March 25, 1972
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After oral administration of 300 mg of 1-phenyl-1-hydroxy-n-pentane (PHP), which increases pancreatic and biliary secretion, to each of three human subjects, its urinary excretion and metabolites were examined by gas chromatography. Excretion of PHP and PHP-glucuronide in the first 4 hr urine was below 1% and 35-37%, respectively, of the dose administered. The amount of both the compounds in urine was very small during 8-48 hr after oral administration.
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SHIGETAKA YOSHINA, KATSUMI YAMAMOTO
1972 Volume 92 Issue 3 Pages
359-365
Published: March 25, 1972
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Comparative examinations were made on the structure of asymmetric benzoins using mass, infrared, ultraviolet, and nuclear magnetic resonance (NMR) spectra. It was thereby found that ultraviolet and NMR spectra were useful means in the structural determination of asymmetric benzoins.
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