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Rikio SHINOHARA, MASAO YOSHIDA, REIZABURO SAKUMA, ISAO ISHIGURO
1973 Volume 93 Issue 2 Pages
127-133
Published: February 25, 1973
Released on J-STAGE: May 30, 2008
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When formamidase purified from rat liver was applied on formylkynurenine, o-formylaminoacetophenone, or formylanthranilic acid as a substrate, respective product, kynurenine showed a non-antagonistic type of inhibition, and o-aminoacetophenone and anthranilic acid a mixed-type inhibition. In order to clarify the relationship between the chemical structure of these inhibitors and their inhibitive action, examinations were made on the mode of inhibition and inhibition ratio of compounds structurally related to kynurenine, o-aminoacetophenone, and anthranilic acid, and their position isomers. From the inhibition ratio and inhibition type of these compounds, the inhibitive ratio was markedly low in compounds having a carboxyl or carbonyl group in the benzene ring, and such compounds showed antagonistic or approximately antagonistic type of inhibition. In contrast, introduction of an amino group into the position ortho to resulted in a marked increase in inhibition with changes in the type of inhibition.
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RIKIO SHINOHARA, MASAO YOSHIDA, REIZABURO SAKUMA, ISAO ISHIGURO
1973 Volume 93 Issue 2 Pages
134-139
Published: February 25, 1973
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Since o-aminophenol, which activates rat liver formamidase, possesses an amino group and an electron-donating hydroxyl group, examinations were made on the effect of compounds having an aromatic amino group and an electron-donating group such as methyl group by using toluidine, phenylenediamine, and their position isomers on the activity of formamidase, and some considerations were made on the relationship between chemical structure and activation effect. Such activation effect was observed in aniline, o- and m-amidophenol, o- and m-phenylenediamine, and m- and p-toluidine. In contrast, paminophenol showed an inhibitive action, o-toluidine showed activation and inhibition according to substrate concentration, and p-phenylenediamine had no effect on the enzyme activity. Thus, the compounds having an electron-donating group besides an amino group do not necessarily activate the enzyme and the relative position of the amino group and electron-donating group was found to be more important. Acylation of the amino group in aniline, which activates the enzyme, resulted in the disappearance of this activating effect, while aliphatic amino group had entirely no effect on the activation. Naphthylamine had no activating effect or, rather, it showed an inhibitive action. It was concluded from these results that a primary amino group bonded to the benzene ring was a requisite for the appearance of activating effect on formamidase.
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JOJU HAGINIWA, YOSHIHIRO HIGUCHI
1973 Volume 93 Issue 2 Pages
140-143
Published: February 25, 1973
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It was considered that the oxygen atom in amine N-oxides would serve as an oxidation agent, and reactions were carried out on acyclic or cyclic amine N-oxides alone or with addition of pyridine N-oxide and ethyl malonate (I), with platinated palladium-carbon catalyst, by heating at 80-110° for ca. 8 hr. The reaction products obtained were tetraethyl propanetetracarboxylate (II) as a neutral component, and a compound (III), formed by introduction of -CH
2COOEt group into α-position of amine-nitrogen, as a basic component (Tables I and II). In general, II is the main product from acyclic aliphatic amine N-oxides (yield, 7-34%) and III is formed in only a trace, while III is a main product (yield, 6.5-27%) from cyclic aliphatic amines, with less of II (yield, less than 2%).
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JOJU HAGINIWA, YOSHIHIRO HIGUCHI
1973 Volume 93 Issue 2 Pages
144-148
Published: February 25, 1973
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It was found that the oxygen atom in amine N-oxides facilitated dehydrogenation of the corresponding amines. Reaction of amine N-oxides with the corresponding amines, using the platinated palladium-carbon catalyst, under the conditions listed in Table I will give in a good yield the homologs of III, VII, and IV, important as the analytical reagents for heavy metals. Dehydrogenation reactuon of VI with palladium-carbon catalyst gives 2, 2'-diquinolyl in 96% yield and 2, 2'-dilepidyl in 60% yield. In this case, addition of a corresponding amine N-oxide results in progress of the reaction under a more mild condition. The platinated palladium-carbon catalyst used in these reactions was found to give markedly different yield of products according to the amount of platinum added.
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MASANORI YOSHIDA, MASAYOSHI SAMEJIMA
1973 Volume 93 Issue 2 Pages
149-156
Published: February 25, 1973
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Examinations were made on the complex formation and solubilizing action of N-substituted and ring substituted acid amides from quantum chemical approach by using the Huckel method. 1) On the basis of molecular orbital considerations, N-substituted pyridinecarboxylic acid amides, except N, N-dimethylnicotinamide, were expected to have electron accepting tendency. In ring substituted benzamides, nitro-substituted acid amides would have electron accepting tendency, but those substituted with amino, chloro, or hydroxyl would have electron-accepting and donating tendencies. 2) N-Substituted pyridinecarboxylic acid amides and ring substituted benzamides formed stable complexes with solubilizates which have electron-donating tendency in aqueous solution, but those which have electron accepting tendency or little donating tendency formed little or no complexes with solubilizates. 3) Degree of complexation of N-substituted pyridinecarboxylic acid amides and ring substituted benzamides which have a high π-electron density on the oxygen atom in acidamide group was found to be much higher than that of substituted acid amides which have a low electron density. Within a homologous series, formation constant of complexes had a linear relationship with π-electron density on the oxygen atom in acid-amide group. 4) Molecular weight of the solubilizates was correlated with the formation constant of complexes.
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YOSHINORI KIDANI, KAZUO OHIRA, HISASHI KOIKE
1973 Volume 93 Issue 2 Pages
157-163
Published: February 25, 1973
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Polarographic behavior of the N-O groups in 1-oxides, 4-oxides, and 1, 4-dioxides of quinoxaline, 2-methylquinoxaline, 2-phenylquinoxaline, and 2-quinoxalinecarboxylic acid is discussed. The reduction wave of quinoxaline ring showed reversibility, but that of the N-O groups was found to be irreversible. Except in 2-quinoxalinecarboxylic acid 1-oxide and 1, 4-dioxide, variation of pH did not show any effect on the wave height of the N-O reduction. However, the limiting current of the first reduction wave of 2-quinoxalinecarboxylic acid 1-oxide and 1, 4-dioxide decreased in the neutral solutions, but the total limiting current of the first and second waves remained constant. These behaviors of the N-O groups can be interpreted by considering that the rate of proton addition to the N-O groups is very fast. By the introduction of a carboxyl, phenyl, or methyl group into the quinoxaline ring, both reductions of quinoxaline ring and the N-O group took place at more positive potentials in the order of COOH>H>C
6H
5≈CH
3. The phenyl and carboxyl groups produced a stronger effect on the reduction potentials of 1-N→O than those of 4-N→O, while a reverse effect was observed for the methyl groups. This order of facility of the N-O reduction can be correlated to the yield of synthetic N-oxidation in the reverse way. The carboxyl and phenyl derivatives of quinoxaline 1, 4-dioxides showed two reduction waves due to the corresponding N-O groups, which were assigned by comparing the half-wave potential and limiting current of their monoxide derivatives, and the reduction mechanisms for these derivatives were suggested.
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JINSAKU SAKAKIBARA, TOYO KAIYA, MASAITI YASUE
1973 Volume 93 Issue 2 Pages
164-170
Published: February 25, 1973
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Dried flowers of Vaccinium bracteatum THUNB. were extracted with benzene and methanol. From the benzene extract were isolated hydrocarbons, aldehydes, friedelin, alcohols, ursolic acid (containing a small quantity of oleanolic acid), and maslinic acid (containing a small quantity of 2α-hydroxyursolic acid). From the methanol extract were obtained ursolic acid, p-coumaric acid, β-sitosteryl β-D-glucoside, mixture of fructose and glucose, orientin, isoorientin, shikimic acid, monotropein, and a new iridoid glycoside named vaccinoside (I). The structure of I was elucidated as 10-(p-hydroxy-trans-cinnamoyl)monotropein through the scheme shown in Fig. 1.
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YOSHIFUMI MAKI, MIKIO SUZUKI
1973 Volume 93 Issue 2 Pages
171-176
Published: February 25, 1973
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Reaction conditions for the Smiles rearrangement in the 3(2H)-pyridazinone system were investigated. 5-(o-Acetamidophenylthio)-4-chloro-3(2H)-pyridazinones (IVa, b, c) underwent the base-catalyzed Smiles rearrangement with ease and subsequent cyclization to afford 10H-benzo[b]pyridazino[4, 5-e](1, 4)-thiazin-4(3H)-ones (IIIa, b, c). Acid treatment of 5-(o-aminophenylthio)-4-chloro-3(2H)-pyridazinones (Ia, b, c) resulted in the preferential formation of 10H-benzo[b]pyridazino[4, 5-e](1, 4)-thiazin-1(2H)-ones (IIa, b, c) together with a small amount of IIIa, b, c. This result indicates that the acid-catalyzed Smiles rearrangement occurred in part. The thermal Smiles rearrangement of I was also observed. Behavior of I toward sodium ethoxide depends largely on the nature of the substituent at 2-position. While methyl and hydrogen derivatives (Ia, b) are fairly stable, reaction of phenyl derivative (Ic) with sodium ethoxide leads to the formation of IIc, IIIc, 4-(o-aminophenylthio)-5-ethoxy-2-phenyl-3(2H)-pyridazinone (IX) and spiro(2-phenyl-4(3H)-pyrazolone-3, 2'-benzothiazoline)(X). It was elucidated that IIIc was formed via unusual displacement followed by cyclization rather than the Smiles rearrangement.
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MASAYUKI NAKAGAKI, HIROSHI NINOMIYA
1973 Volume 93 Issue 2 Pages
177-185
Published: February 25, 1973
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The sedimentation states of procaine penicilline G (PPG) in the sedimentation bed was examined by the measurement of geometric parameters, prosity (ε) and tortuosity (q), the latter being calculated from the relative conductivity ratio (f). PPG powder crushed by Jet-O-Mizer was used as the sample. Aqueous solutions of various molecular weight (M^
-η) of poly(vinylpyrrolidone)(PVP) and sodium carboxymethylcellulose (CMC-Na) after being saturated with PPG were used as the suspending medium at 25°. It was found that the sedimentation volume of PPG varied with the concentration and M^
-η of PVP. Variations were, however rather little in the case of CMC-Na. The tortuosity (q) showed different values according to whether it was measured in the horizontal (qH) or in the vertical (qv) direction of the bed. It was also found that qH was greater than qv. All the data plotted to see the relation between q and ε fell on the same line, showing that q decreased with the increase of ε. In the case of glass sphere, both ε and q were almost constant and the rafio of qv/qH was equal to 1. There was little effect of particle concentration on ε and q of PPG in the sedimentation bed.
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HIDEKO KAWAKI, SETSUKO UZIHARA, YUKO OKAZAKI
1973 Volume 93 Issue 2 Pages
186-190
Published: February 25, 1973
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Photochemical oxidation of o-aminophenol was carried out in 30% ethanol or 30% dioxan solution and changes during this reaction were followed by polarography and electron absorption spectrum. Irradiation of 30% dioxan solution of o-aminophenol over a long time resulted in the appearance of a wave (E
1/2=-0.85V) for separation of hydrogen peroxide, besides the reduction wave (E
1/2=-0.5V) of 3-aminophenoxazone and that (E<1/2>=-1.2V) of hydrogen peroxide seen at the time of short irradiation. Oxidation products were obtained as two kinds of crystals ; crystal 1 of red needles, mp 250-251°, corresponding to 3-aminophenoxazone, and crystal 2 of deep reddish purple needles, mp 260-261°, which was found to contain 50% of 3-aminophenoxazone from the comparison of polarographic reduction wave height and E<425> nm. Since the electron spin resonance spectrum of crystal 2 was similar to that of quinhydrone, it was concluded that this product is a 1 : 1 complex of 3-aminophenoxazone and 3-hydroxy-3-aminophenoxazine.
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SHUN'ICHI TSUKIYAMA, AKIRA TAKAMURA, YOSHIKO WAKAMATSU, IWAO TAKASHIMA
1973 Volume 93 Issue 2 Pages
191-196
Published: February 25, 1973
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This paper deals with effect of impeller velocity and emulsifying agent concentration on dispersion process. The apparatus consists of a cylindrical vessel (dt=150 mm) made of clear acrylate resin and Rushton-type impeller (di=49 mm). Water and a mixture of n-C
7H
16 and CCl
4 were used as the continuous phase and the dispersed phase. Tween-20 and Tween-81 were employed as the emulsifying agent, and their concentration was 1%, 10
-2%, 10
-3% and 10
-4%. Agitation was continuously done for 60 min, and revolution of the agitator was 330, 400, 530, or 660 rpm. The photographs of droplets were taken by a microscopic method, and the particle size distribution was calculated. The results obtained were as follows. 1) The normalized standard deviation was smaller with increasing concentration of the emulsifying agent, and the droplet size became uniform. 2) Irrespective of the concentration of emulsifying agent, surface energy Es had a constant value. 3) Experimental equation relative to the mean surface-volume diameter, d
32, surface tension γ, revolution number N, and agitation time θ wa as follows : [numerical formula]
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CHIAKI TANI, SACHIKO TAKAO, KIYOSHI TAGAHARA
1973 Volume 93 Issue 2 Pages
197-201
Published: February 25, 1973
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Thermal decomposition (Pyrolysis) of the N-methiodides of tetrahydrocoptisine and tetrahydroprotoberberine results in demethylation in the majority to form a tetrahydroprotoberberine-type substances, but some were found to form a 13-methyltetrahydroprotoberberine-type compounds by rearrangement of the N-methyl group to the 13-position. Identity of these products was proved by comparison with synthetic speciments, and steric structure of these compounds was assumed from infrared and nuclear magnetic resonance spectra to possess a trans-quinolizidine ring, with 13-methyl oriented in axial position.
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KONO KINOSHITA, SETSUKO MURASE
1973 Volume 93 Issue 2 Pages
202-206
Published: February 25, 1973
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A new type coumarim (II), C
15H
16O
5, mp 234°, was isolated from rhizomes of Glaucidium palmatum SIEN. et ZUCC., and named glaupadiol. From the experimental results of nuclear magnetic resonance, optical rotatoly dispersion, infrared, and mass spectra, this compound (II) was found to be a mixture of cis and trans forms, and its structure was revealed as 3-hydroxymethyl-8-hydroxy-2, 3, 9-trimethyl-2, 3-dihydrofuro[3, 2-c]-chromen-4-one. The hydroxymethyl group in this compound (II) was bonded to the furan ring in place of the methyl group of racemic glaupalol (I), which was previously isolated from this rhizome.
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ISOO ITO, TAISEI UEDA
1973 Volume 93 Issue 2 Pages
207-213
Published: February 25, 1973
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The Ullmann reaction of 4-bromo-3-(2-formamidophenyl)thiomethyl-2-methyl-1-phenyl-3-pyrazolin-5-one (IV) in an aprotic dipolor solvent such as dimethylformamide gave a five-membered ring compound 3-(3-formamidobenzothiazol-2-yl)-2-methyl-1-phenyl-3-pyrazolin-5-one (VII). Hydrolysis of VII in 10% HCl-EtOH (1 : 1) save 3-(2-benzothiazolyl)-2-methyl-1-phenyl-3-pyrazolin-5-one (III) . However, the Ullmann reaction of IV in a nonrolar solvent such as xylene afforded a seven-membered ring compound, 4-formyl-1-methyl-2-phenyl-1, 2, 3, 10-tetrahydro-4H-pyrazolo[3, 4-c][1, 5]benzothiazepin-3-one (XI). Hydrolysis of XI in 10% HCl-EtOH (1 : 1)gave 1-methyl-2-phenyl-1, 2, 3, 10-tetrahydro-4H-pyrazolo[3, 4-c][1, 5]benzothiazepin-3- one (I). The Ullmann reaction of 4-substituted-3-(2-acylamido-4-substituted phenyl)-thiomethyl-2-methyl-1-phenyl-3-pyrazolin-5-ones was studied in various solvents. The structure of III was proved by its synthesis by other routes.
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MASAYUKI NAKAGAKI, YOH SANO
1973 Volume 93 Issue 2 Pages
214-222
Published: February 25, 1973
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Since the effect of dextran, as a plasma expander, differs wide1y according to its molecular weight, the dextran solutions of various molecular weight has been studied by light scattering and viscosity methods. According to the Zimm plot method, the weightaverage molecular weight, M
w, radius of gyration, R
g, and second virial coefficient, A
2, were obtained for (1) solutions dissolved at 25°, (2) the solutions heated at 80° for 2 hr and (3) mixed solutions of two polymers dissolved at 25°. The relation of A
2=4.90×10
^<-2>M
-0.426 between A
2 and M
w is obtained in common for (1) to (3). R
g for the case (1), on the other hand, decreased at first with increase of M
w and reached a minimum at M
w=110000 and then increased at M
w=2500000. For the case (2), the value of R
g increased by heating. For the case (3), R
g was larger than the values expected from those of both components. The data for cases (2) and (3) are expressed by the equation R
g=1.67×10
-7M
w0.187. The relation [η]=6.95×10
-4M
w0.493 was also obtained for the intrinsic viscosity [η] of these solutions. It is concluded that the dextran molecules are dissolved in more extended state in aqueous solution when the solutions are heated or when the sample is a mixture of dextrans of different molecular weight.
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MUNEHARU OGAWA, SUEO HISADA, ISAO INAGAKI
1973 Volume 93 Issue 2 Pages
223-225
Published: February 25, 1973
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A new natural phenolic glucoside, koaburaside, was isolated from the stems of Enkianthus nudipes (HONDA) OHWI. This compound was found to be 1, 4-dihydroxy-2, 6-dimethoxybenzene-4-O-β-D-glucoside on the basis of chemical and spectroscopic evidences. This compound was isolated for the first time from a natural source.
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TAKASHI NISHIKAWA, KAZUYUKI MINEURA, HIROSHI TAKAHIRA
1973 Volume 93 Issue 2 Pages
226-231
Published: February 25, 1973
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The fate of flurazepam hydrochloride, 7-chloro-1-(2-diethylaminoethyl)-5-(2-fluorophenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one monohydrochloride, having a sleep-inducing effect, was investigated in rats after oral or intravenous administration of this compound labeled with
14C at the C-5 position. It became evident that orally administered compound was absorbed well and highly distributed in some particular tissues followed by rapid excretion in feces and urine. The radioactivity in blood reached a considerably high level at 30 min, but was much lower than that in some tissues, such as liver, lung, kindney, spleen, and abdominal fat after oral administration. Examination of tissue distribution after intravenous administation also indicated extensive tissue uptake of radioactivity. In both routes of administation, radioactivity in the tissues was rapidly eliminated and most of the radioactivity was excreted during the first day in feces and urine. It was found that bile duct-cannulated rat excreted a large portion of the radioactivity in bile after both routes of administration. This result suggestes that the radioactivity excreted in feces by way of the bile duct. Results of these studies demonstrated rapid and complete absorption of this labeled compound, followd by rapid excretion of radioactivity whtih no apparent accamulation in any tissue.
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TAKASHI NISHIKAWA, KAZUYUKI MINEURA, HIROSHI TAKAHIRA
1973 Volume 93 Issue 2 Pages
232-238
Published: February 25, 1973
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The metabolic fate of Flurazepam hydrochloride, 7-chloro-1-(2-diethylaminoethyl)-5-(2-fluorophenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one monohydrochloride, having a sleep-inducing effect, was examined in a rat after oral administration of this compound labeled with
14C at the C-5 position. Radioactive metabolites in bile and urine were fractionated to be identified. Less than 3% of the bilary
14C could be extracted with ethyl acetate at pH 9.0 and no appreciable amount of intact Flurazepam was detected in this extract. In bilary metabolites, N-dealkylated compounds (>NCH
2CH
2NHC
2H
5, >NCH
2CH
2NH
2), thier conjugates, and the conjugate of N
1-ethanol (>NCH
2CH
2OH) were found. In urinary metabolites, N
1-acetic acid (>NCH
2COOH) was found in addition to the bilary metabolites. One of major metabolites in both bile and urine remained unidentified, but it was evident that this unidentified metabolite was soluble in water, had no acidic group, kept a benzodiazepine ring structure, and had an N
1-aminoethyl group (>NCH
2CH
2N<). From these results, the pathway of Flurazepam in rat was postulated as shown in Chart 4.
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FUMIKO HAMAGUCHI, TATSUO NAGASAKA
1973 Volume 93 Issue 2 Pages
239-241
Published: February 25, 1973
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2-Acylcyclohexanones (IV and V) are obtained from the reaction of amide-POCl
3 complexes (II and III) with enamine (I), while the lactam-condensed products (VIII and XII) or enamine-reduced products (XI and XIV) are obtained from the reaction of lactam-POCl
3 complexes (VI and X) with enamines (I or XIII).
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NARAO TAKAO, YUKI YASUMOTO, KINUKO IWASA
1973 Volume 93 Issue 2 Pages
242-244
Published: February 25, 1973
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It was established that the new alkaloid isolated from Bocconia cordata and tentavely named Base A was dehydrocheilanthifoline (III). This is the first time that dehydrocheilanthifoline was isolated from plants.
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YOSHIRO SATO, YASUCHIKA BAN, HIDEAKI SHIRAI
1973 Volume 93 Issue 2 Pages
244-246
Published: February 25, 1973
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Triethylvinyltin (I) reacted with diethyl malonate or ethyl acetoacetate in presence of DTBP to give only β-addition products : diethyl triethylstannylethylmalonate (IV) 37.6% or 3-ethoxycarbonyl-5-triethylstannyl-2-pentanone (V) 43.6%. Then several 5-triethylstannylethylpyrimidine derivatives (VIIIa, c, IXa, b, c) were synthesized from the reaction of IV or V with urea, thiourea and guanidine respectively except the case of IV with thiourea.
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TSUNEHIKO ASAKO, KENTARO HIRAGA, TAKUICHI MIKI
1973 Volume 93 Issue 2 Pages
246-247
Published: February 25, 1973
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rac-3-(3-oxo-17β-hydroxy-13-ethylgon-4-en-17α-yl)-3-propionic acid γ-lactone (VI) was prepared in 15% yield from rac-17α-ethynyl-13-ethylgona-1, 3, 5(10)-trien-17β-ol (II) through carbynylation, reduction, and hydrolysis.
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KIYOSHI HATA, MITSUGI KOZAWA, KIMIYE BABA, MASAKO MITSUI
1973 Volume 93 Issue 2 Pages
248-251
Published: February 25, 1973
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The chemical investigations of the roots of two Umbelliferous plants, Ligusticum hultenii FERNALD and Angelica shikokiana MAKINO, which was formerly assigned to Ligusticum shikokianum MAKINO, were made. 7-Methoxy-8-senecioylcoumarin (V), besides crocatone (III) and 3-methoxy-4, 5-methylenedioxy-trans-cinnamic acid (TV), was isolated from the former, and two khellactone diester, anomalin (VII) and isopteryxin (VIII), from the later. These results indicate that there is no chemotaxonomic relation between tese two species. Nevertheless they were formerly regarded to belong to the same genus, but the latter is closely related to Angelica anomala LALL. and A. cartilaginomarginata (MAKINO) NAKAI in chemical components.
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TOMOO TANAKA
1973 Volume 93 Issue 2 Pages
252-257
Published: February 25, 1973
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The masking properties of thiopyrine in chelatometric titrations was examined. With the use of this reagent at pH 1.5-4 or pH 5-6, it is possible to determine thorium(IV), bismuth(III), zirconium(IV), iron(III), nickel(II), zinc(II), lead(II), cobalt(II), cadmium (II), and aluminium(III) in the presence of mercury(II), thallium(III), and copper(II). Also at pH 10-12, mercury(II) can be selectively masked in the titration of nickel(II), calcium(II), and magnesium(II). Thiopyrine reacts with the EDTA complexes of mercury(II), thallium(III), and copper(II), and liberates EDTA quantitatively. This reaction was applied to the separatory titration of mercury(II), thallium(III), or copper(II) and various metal ions with a good result.
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YOSHIHARU KANEO, TSUYOSHI GOROMARU, SADAO IGUCHI
1973 Volume 93 Issue 2 Pages
258-260
Published: February 25, 1973
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