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Antibacterial and Antifungal Properties of Organic Mercurials containing Theophylline Derivatives
Kazumi Toyoshi, Katsuhiko Katô, Katsuyo Yamada, Kazue Komoda, Uz ...
1964 Volume 84 Issue 12 Pages
1149-1152
Published: December 25, 1964
Released on J-STAGE: February 19, 2010
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A growth inhibitory test of the organo-mercuric compounds, containing theophylline derivatives against eight sorts of strains, such as
Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Alcalescens Dispar type I,
Psuedomonas aeruginosa, Salmonella paratyphi B,
Proteus OX 19 and
Trichophyton mentagrophytes was studied by the paper disk method with thimerosal and phenylmercuric acetate as controls, and any derivatives was found to be inferior to thimerosal in its antibacterial activity. However, it was found that 7-(phenylmercuri) theophylline (1), 7-(
p-tolylmercuri) theophylline (2),
o-(chloromercuri) phenol (12) and (
o-bromomercuriphenyl) methanol (17) showed similar antibacterial properties to phenylmercuric acetate. Among the eight sorts of bacterial strains, gram negative bacteria had an tendency to be less sensible than gram positive bacteria against organo-mercuric compounds.
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Noboru Kasugai
1964 Volume 84 Issue 12 Pages
1152-1157
Published: December 25, 1964
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Either sodium or potassium salt of Mg-, Co-, Mn-, V-, Ag-, Zn-, Au-chlorophyllin and Co-chlorophyllin coordinated with either methionine, adenine, folic acid or ammine ion, which is chelated by phytochlorin derived from chlorophyll, were prepared in order to examine chemical protectors against radiation injury. Animal experiments of each of chlorophyllin metal chelate compounds for LD
50 showed very low toxicity. The protective effect of the compound against radiation injury was determined by comparative study on survivals between the treated and untreated mice following to the lethal general irradiation. Consequently, a survival rate of the treated groups were found to be superior to the untreated groups, and the hexacoordinated chlorophyllin metal (Co, Mg, Mn and V) chelate compounds were found to be effective.
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Structural Viscosity of Aluminum Stearates in Vegetable Oils
Misao Nishino
1964 Volume 84 Issue 12 Pages
1158-1162
Published: December 25, 1964
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The structural viscosity of aluminum stearate was measured in either sesame or peanut oil solution in the similar way observed in benzene solution, but the concentration, at which the structural viscosity appeared, was found to be higher than that of benzene solution. Concentration dependency of η
N (=η
r(1/Q→0)) in oil solution was weaker than that in benzene solution. Intrinsic viscosity [η
N] was much lower than that in benzene solution and there was not found such a sharp peak in the relation between [η
N] and St/Al ratio as observed in benzene solution. As to the result, it was considered that polymer chains of aluminum stearate were less extended in these oils than in benzene, or that polymer chains of aluminum stearate, especially of disoap, were broken either by a required heating for a preparation of oil solution, or by coordination of a certain component in the oil.
It was also found that structural viscosity, concentration dependency of η
N and intrinsic viscosity [η
N] were varied with the soap composition in oil solution, and these properties are observed most remarkably in disoap solution as compared with the other soap solutions.
In addition, no essential difference between sesame oil and peanut oil was observed.
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Effect of Additives on the Viscosity of Benzene Solution of Aluminum Distearate
Masayuki Nakagaki, Misao Nishino
1964 Volume 84 Issue 12 Pages
1162-1166
Published: December 25, 1964
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Intrinsic viscosity of a mixture of aluminum-distearate and either aluminum-monostearate or stearic acid was measured in benzene. By the addition of a small quantity of either monosoap or stearic acid to disoap, [η
N] decreased suddenly similar to that of the synthesized soaps, which were reported in a previous paper, but the values of [η
N] were found higher than that of synthesized one. The actions of monosoap and stearic acid to the disoap were compared with those of ethyl alcohol, octadecyl alcohol,
p-toluidine and acetic acid. Each of additives was heated with aluminum-distearate in benzene, and the viscosity of this solution was measured at various concentrations of the additives in different heating period. Monosoap and alcohol made the viscosity lower monotonously, as the concentration of the additives was increased and heating period of time was lengthened. With stearic acid, the viscosity was increased at a low concentration in a short period of heating time, but it decreased with an increase of the concentration and the heating period of time. Monosoap and stearic acid, similar to the other additives, were found to depolymerize disoap polymer by the coordination. An increase of viscosity by the addition of stearic acid was considered to explaine by the formation of disoap from monosoap and stearic acid and by the coordinate bond between two oxygen atoms of stearic acid and two aluminum atoms and hence the chain was made longer.
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Ken-nosuke Sakurai, Eiichi Yoshii, Kiichi Kubo
1964 Volume 84 Issue 12 Pages
1166-1171
Published: December 25, 1964
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Five kinds of bufadienolide shown in Chart 1 were analyzed by gas chromatography of trimethyl silyl ethers on a packed column of SE-30 (1.5%) at 235°. Their retention time and chromatogram are shown in Table I and Fig. 1. After simple pretreatment by column chromatography on alumina, cinobufagin content of Ch'an Su (Chinese drug, Tô-Senso) was estimated by gas chromatography as 7.2±0.2%.
γ-Sitosterol previously isolated from hexane-soluble part of Ch'an Su extract was shown to be a mixed crystal comprising of cholesterol, campesterol, and β-sitosterol, from the result of gas chromatograph and infrared spectral measurement.
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Color Reaction of Phenols with Sodium 1, 2-Naphthoquinone-4-sulfonate and its Application to Colorimetric Determination of Resorcinol
Masuo Umeda
1964 Volume 84 Issue 12 Pages
1171-1175
Published: December 25, 1964
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A color reaction of phenol derivatives by sodium 1, 2-naphthoquinone-4-sulfonate was investigated. Among about 40 kinds of phenols, those substituted by a positive group at a
o-position gave much better coloration, while no color or at least only faint color was observed in case of
m- or
p-substituted one by the same group. Phenols substituted by a negative group gave negative results without exception. As to polyphenols resorcinol alone gave good color and others generally showed brown coloration perhaps due to air oxidation. Similar results were obtained, even when sodium 1, 2-naphthoquinone-4-sulfonate was replaced by 1, 2-naphthoquinone. Then this color reaction was applied for the colorimetric dertermination of resorcinol successfully. Limit of measurement, 20-180μg./ml., and σ=0.846 (
n=6). One ml. sample solution (water solution containing 20-180μg./ml., of resorcinol) was taken exactly in 10ml. measurring flask, 1ml. of 0.2% sodium 1, 2-naphthoquinone-4-sulfonate solution and 2.5ml. of pyridine were added and shaken well. After kept standing for 5min. at 15° 1ml. of 0.45
N sodium hydroxide solution was added, shaken well and kept standing at the same temperature for 15min. Then water was added to make 10ml. exactly and the absorbance at 680mμ was measured. As a reference solution for the measurement 1ml. of water was treated in the same manner.
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A New Basic Amino Acid “Laminine” and the Other Basic Constituents isolated from Laminaria angustata
Tsunematsu Takemoto, Koji Daigo, Nobuya Takagi
1964 Volume 84 Issue 12 Pages
1176-1179
Published: December 25, 1964
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New basic amino acid, named laminine after Laminaria, was discovered from aqueous extracts of
Laminaria angustata and its oxalate, m.p. 122-124°, [α]
D18+10.8° (H
2O), C
13H
24O
10N
2⋅1/2H
2O, was isolated as colorless needles. From the various findings, the chemical structure of laminine oxalate was regarded to be trimethyl-(5-amino-5-carboxypentyl)-ammonium dioxalate. Besides laminine, L-lysine, L-arginine, ethanolamine and choline isolated have been proved as basic components from
L. angustata.
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Synthesis of Laminine and Related Compounds
Tsunematsu Takemoto, Koji Daigo, Nobuya Takagi
1964 Volume 84 Issue 12 Pages
1180-1182
Published: December 25, 1964
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Both natural laminine and the synthesized substances, according to the A method: methylation of copper complex of L-lysine by dimethylsulfate, and to the B method: methylation of N
2-acetyl-L-lysine, followed by hydrolysis, were in good agreement in every respect. The reaction between 6-chloro-2-aminohexanoic acid and trimethylamine gave DL-laminine (oxalate, m.p. 129-130°, C
13H
24O
10N
2⋅1/2H
2O, colorless needles). Besides, trimethyl-(5-amino-1-carboxypentyl)-ammonium oxalate, m.p. 200°, [α]
D +8.4° (H
2O), C
20H
42O
8N
2⋅4H
2O, colorless needles, L-lysine betaine dipicrate, m.p. 217° (decomp.), C
24H
32O
16N
8, yellow platelets, trimethyl-(4-amino-4-carboxybutyl)-ammonium dioxalate, m.p. 111-113°, [α]
D+11.0° (H
2O), C
12H
22O
10N
2⋅H
2O and trimethyl-(3-amino-3-carboxypropyl)-ammonium oxalate, m.p. 181° (decomp.), [α]
D+10.4° (H
2O), C
9H
18O
6N
2 were synthesized.
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Isolation of the Flycidal Constituent from Tricholoma muscarium
Tsunematsu Takemoto, Tadashi Nakajima
1964 Volume 84 Issue 12 Pages
1183-1186
Published: December 25, 1964
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A colorless pillar crystalline component, m.p. 207° (decomp.), [α]
D+80.0°(H
2O), C
5H
8O
4N
2 of good flavor without smell, and of having insecticidal property was isolated from
Tricholoma muscarium KAWAMURA (Jap. name: Haetorishimeji) in the process illustrated in Fig. 1. The compound was considered to be acidic amino acid, still unknown substance, which named tricholomic acid.
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Isolation of the Flycidal Constituent from Amanita strobiliformis
Tsunematsu Takemoto, Tetsuro Yokobe, Tadashi Nakajima
1964 Volume 84 Issue 12 Pages
1186-1188
Published: December 25, 1964
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From
Amanita strobiliformis (PAUL.) QUER. (Jap. name: Ibotengutake), colorless and odorless pillar crystalline component with good flavor, providing remarkable fly-killing properties, m. p. 151-152° (decomp.), C
5H
8O
5N
2 was isolated. The compound is considered to be an unknown acidic amino acid and is called ibotenic acid, naming after the ibotengutake.
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Pharmacological Studies on Repeated Administration of Analgesics
Keigo Nishino, Noriko Ichinoseki, Tsutomu Irikura
1964 Volume 84 Issue 12 Pages
1189-1194
Published: December 25, 1964
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An appearance of tolerance and physical dependence was examined with 1, 4-bis-[(2-methoxy-4-propylphenoxy) acetyl] piperazine (AP-2) by analgesic administration to guinea pig and rat, comparing with that of morphine as a control. In the case when morphine was treated subcutaneously to guinea pig successively, it showed tolerance, however, AP-2 (200mg./kg.) did not display tolerance even when it was treated either peritoneally or per os consecutively (Figs. 3, 4).
A decrease of body weight, caused by physical dependence, was observed if the administration was discontinued or otherwise either levallorphan or AP-2 was administered instead of morphine, after the consecutive administration of morphine (100mg./kg.) to rat twice a day. However, no decrease of body weight was observed with the rat treated in advance by successive administration of AP-2 (200mg./kg.) twice a day, if the administration was discontinued or levallorphan was administered instead of AP-2.
To the tolerated guinea pig or rat with morphine, either suspension of water insoluble AP-2 or precipitated calcium carbonate was administered peritoneally, and a severe stretching symptom was displayed. It suggests that these tolerated animals with morphine were considered to be very sensitive to the stretcing reaction.
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The Isolation of Bases
Shoji Ozeki
1964 Volume 84 Issue 12 Pages
1194-1197
Published: December 25, 1964
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Four known alkaloids, lycorine (I), tazettin (II), nerinine (III), haemanthidine (IV) and a new alkaloid C
16H
19O
4N, m.p. 201-202° (decomp.), were isolated from
Zephyranthes candida HERB., Amaryllidaceae (Japanese name “Tamasudare”) which has been cultured in Japan as decorative plants.
Physical constants of the new alkaloid which is designated zephyranthine are as follows: [α]
D24 -43.17° (
c=0.47, CHCl
3); IR ν
maxKBrcm
-1: 3470 (-OH), 1040, 945 (methylenedioxy group); pKa′ 9.20 in water; UV λ
maxEtOH 291mμ (log ε 3.71). The alkaloid contains one methylenedioxyphenyl group, two hydroxyl groups and one tertiary nitrogen, but no N-methyl, O-methyl or olefinic unsaturated functional groups. It gives diacetate, C
20H
23O
6N, m.p. 68-70° and acetate hydrochloride, C
20H
23O
6N⋅HCI, m.p. 294-295° (decomp.).
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Adsorption of Amino Acid
Akinobu Otsuka, Teruko Otani
1964 Volume 84 Issue 12 Pages
1198-1201
Published: December 25, 1964
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Adsorption of amino acids from aqueous solution by synthetic aluminum silicate gel was examined and following results were obtained.
1) Basic amino acids are adsorbed in larger quantities than neutral amino acids. This is due to the fact that basic amino acids are dissociated in the experimental pH range and are present in cationic form.
2) The adsorption isotherm shows the Langmuir type when pH is constant.
3) Adsorption of amino acids is the highest when alumina content of the gel is around 10%.
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Reactions of Diketene with Amino-heterocycles
Tetsuzo Kato, Hiroshi Yamanaka, Hirotaka Moriya
1964 Volume 84 Issue 12 Pages
1201-1205
Published: December 25, 1964
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Reactions of diketene with amino-heterocycles, such as aminoquinoline, thiazole and pyrimidine derivatives, were examined.
2-Aminoquinoline (VI) was converted to 2-acetoacetamidoquinoline (VII) in 82% yield, and 4-amino-isomer (VIII) was transformed to 1-(4-quinolyl)-3-acetyl-6-methyl-2, 4(1
H, 3
H)-pyridinedione (IX) in 60% yield. 2-Aminothiazole (X) reacted with diketene to give 2-acetoacetamidothiazole (XI) (70%) and 7-methyl-5
H-thiazole [3, 2-
a] pyrimidine-5-one (XII) (26%).
2-Aminopyrimidine (XIII), 2-amino-4-methoxy-6-methylpyrimidine (XVII), 2-amino-4-methylpyrimidine (XIX), 4-amino-6-chloropyrimidine (XXIII) and 4-amino-6-alkoxy-pyrimidine (CH
3O (XXIV), C
2H
5O (XXV), (CH
3)
2⋅CHO (XXXI)) were converted to their acetoacetyl derivatives comparatively in good yields.
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Seiichi Okui, Yasuo Suzuki, Hideki Koyama, Osamu Umezawa
1964 Volume 84 Issue 12 Pages
1206-1209
Published: December 25, 1964
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The hydrolysis of phosphatidylcholine by hydroxides of alkaline earth metals was studied in methanolic solution under mild conditions. A hydrolysis was not taken place by magnesium hydroxide, but calcium hydroxide, barium hydroxide, and strontium hydroxide participated in the hydrolysis to a various degree similarly in sodium hydroxide-metanolic solution. Under the condition of 5×10
-3N of barium hydroxide in methanolic solution for 30 minutes at 37°, L-α-glycerylphosphorylcholine was obtained in a good yield. This method was considered to be simple and available for a larger-scale preparation of this compound.
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Effect of Sucrose Esters on the Absorption of Drugs from the Alimentary Tract
Kiichiro Kakemi, Takaichi Arita, Hitoshi Sezaki, Isao Sugimoto
1964 Volume 84 Issue 12 Pages
1210-1214
Published: December 25, 1964
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Effect of various types of surface active agents on the absorption of drugs was investigated using perfusion technique by rat small intestine.
Tetracycline (TC), sulfanilamide (SF), isoniazid, and salicylic acid (SA) were used as test drugs, and sodium laurylsulfate (SLS), benzethonium chloride, polysorbate 80 (PS-80), sucrose monostearate, and sucrose distearate were used as surface active agents.
It was found that: (1) ionic nature of the surfactants substantially influenced the absorption, (2) a rate of absorption of TC was accelerated by the presence of SLS, benzethonium chloride or sucrose esters, (3) PS-80 showed a marked reduction in the absorption of SA and TC, (4) benzethonium chloride reduced the absorption of SA, and (5) sucrose esters within the concentrations tested did not decrease the absorption of all the drugs tested. They were explained by the low thermodynamic activity of the drugs in the vehicles due to complexing or other forms of interactions and/or by the correlation with organic solvent/isotonic buffer solution partition ratios.
Amount of the drug excreted into urine was measured, following to oral administration of the solution of the drug-surfactant combination to adult human subjects. The results supported the foregoing conclusions that sucrose esters greatly enhanced, while PS-80 markedly reduced the absorption of TC, and that the absorption of SF was not affected significantly by the presence of sucrose esters.
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Synthesis of Methyl O-(2-Acetamido-2-deoxy-tri-O-acetyl-β-D-glucopyranosyl)-(1→1)-tri-O-acetyl-α-D-glucopyranuronate and O-(Methyl Tri-O-acetyl-β-D-glucopyranosyluronate)
Hisao Tsukamoto, Mitsuharu Takeda, Nobuyuki Hirano
1964 Volume 84 Issue 12 Pages
1215-1217
Published: December 25, 1964
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Methyl O-(2-acetamido-2-deoxy-tri-O-acetyl-β-D-glucopyranosyl)-(1→1)-tri-O-acetyl-α-D-glucopyranuronate (II) was synthesized by the condensation of methyl 2, 3, 4, -tri-O-acetyl-α-D-glucopyranuronate (IV) with acetochloroglucosamine (V) in the presence of mercuric cyanide in nitromethane and similarly O-(methyl tri-O-acetyl-β-D-glucopyranosyluronate)-(1→6)-2-acetamido-2-deoxy-tri-O-acetyl-β-D-glucopyranose (III) was prepared by the condensation of 2-acetamido-2-deoxy-1, 3, 4-tri-O-acetyl-α-D-glucopyranose (VI) with methyl 1-bromo-tri-O-acetyl-α-D-glucopyranuronate (I) in the presence of silver oxide in chloroform.
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Alkaloids of Corydalis incisa. (7). Syntheses of 2-Methyl-6, 7-methylenedioxynaphthalene
Chiaki Tani, Narao Takao, Kiyoshi Tagahara
1964 Volume 84 Issue 12 Pages
1217-1219
Published: December 25, 1964
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A selenium dehydration of the des-N compound, derived from corynoline, a new alkaloid, isolated from
Corydalis incisa afforded crystal of m.p. 127°, which was found to be identical with 2-methyl-6, 7-methylenedioxynaphthalene as reported. It was synthesized for the purpose of identification and both compounds, the isolated and synthesized, were certified to be quite identical and the position of quaternary C-methyl was also determined.
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4-Methyl-3, 4, 5, 6-tetrahydrobenzo[f]quinolin-1(2H)-one. A Minor Product of Cyclization of Ethyl 3-[(3, 4-Dihydro-2-naphthyl)-methylamino] propionate
Zen-ichi Horii, Chuzo Iwata, Masayoshi Ito, Yasumitsu Tamura
1964 Volume 84 Issue 12 Pages
1220-1222
Published: December 25, 1964
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It was reported that the enamine-ester (III), prepared by the condensation of 2-tetralone and ethyl 3-(methylamino) propionate, undergoes rearrangement on heating in ethylene glycol, to give 4-methyl-1, 2, 5, 6-tetrahydrobenzo [
f] quinolin-3(4
H)-one (I) as a sole product. Reinvestigation of this reaction revealed that it produced also a small amount of 4-methyl-3, 4, 5, 6-tetrahydrobenzo [
f] quinolin-1(2
H)-one (II) as a minor by product. The structure of II was proved by conversion to its dihydro derivative (IV) synthesized.
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Kiyoshi Takiura, Susumu Honda
1964 Volume 84 Issue 12 Pages
1223-1224
Published: December 25, 1964
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Two kinds of sugar were isolated from the aqueous digest of the root of
Polygala tenuifolia WILLDENOW by column chromatography using carbon and Dowex-1X 8. These sugars were identified as 5-anhydro-D-sorbitol and N-acetyl-D-glucosamine.
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Amino Acids
Tsunematsu Takemoto, Tatsuei Sai
1964 Volume 84 Issue 12 Pages
1224-1227
Published: December 25, 1964
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By means of the two-dimensional paper (partition) chromatography, amino acid components of
Ceratodictyon spongiosum ZANARDINI (Gracilariaceae) have been examined and eighteen spots have been recognized to be colored by Ninhydrin. This fact suggested a presence of aspartic acid, glutamic acid, serine, glycine, alanine, tyrosine, valine, leucine, isoleucine, proline and histidine tentatively. Besides that, betaine, L-tyrosine, glycine, L-glutamic acid, L-aspartic acid and taurine have been identified by the isolation of pure crystals.
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Isolation of Chelidonic Acid
Michiya Kimura, Masahiko Toma, Itsuo Yoshizawa, Shun-ichi Endo
1964 Volume 84 Issue 12 Pages
1227-1229
Published: December 25, 1964
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Chelidonic acid, m. p. 256-257°(decomp.), was isolated and identified from the dried flowers of lily of the valley,
Convallaria keisukei MIQ., growing in Hokkaido.
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Tsunematsu Takemoto, Tadashi Nakajima, Tetsuro Yokobe, Reiko Sakuma, K ...
1964 Volume 84 Issue 12 Pages
1230-1236
Published: December 25, 1964
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1964 Volume 84 Issue 12 Pages
e2a
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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1964 Volume 84 Issue 12 Pages
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