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Volume 19, Issue 11
Displaying 1-40 of 40 articles from this issue
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TAIICHIRO WATANABE, NOBUO SOMA1971 Volume 19 Issue 11 Pages 2215-2221
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 2-phenyl-3-(2, 4, 6-cycloheptatrien-1-yl) propionaldehyde ethylene acetal (III) with stannic chloride in benzene followed by dehydrogenation with sulfur afforded 2-phenylazulene (V) and 1-(2-hydroxyethyloxy)-2-phenylazulene (VI). Benz[a]azulene (XV) was obtained along with anthracene (XVI) when 2-(2, 4, 6-cycloheptatrien-1-yl)-benzaldehyde (XII) or its ethylene acetal (XI) was treated with stannic chloride in benzene or with hydrogen bromide in acetic acid.View full abstractDownload PDF (828K) -
AKIRA TAKAMIZAWA, KENTARO HIRAI, TERUYUKI ISHIBA1971 Volume 19 Issue 11 Pages 2222-2228
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of thiamine anhydride (I) with CH3COSH gave acetylthioethyl SB1 (II), which was converted into acetylthioethylthiamine (IV). Mercaptoethylthiamine (V), a Sanalogue of thiamine, was obtained from IV. A munber of reactions of IV and V were carried out to give a variety of S-analogues of thiamine derivatives. Thiol type S-acyl derivatives, disulfides, perhydrothieno [2, 3-d] thiazole derivatives, and hexahydrothienothiachromine derivatives were synthesized.View full abstractDownload PDF (845K) -
AKIRA TAKAMIZAWA, KENTARO HIRAI, TERUYUKI ISHIBA1971 Volume 19 Issue 11 Pages 2229-2234
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA number of new thiamine derivatives in which the OH group of thiamine Th-5-CH2CH2OH is replaced by CH2CH2N■, CH2CH2SR, CH2CH2SOR, or CH2CH2SO2R groups were prepared. Some of these compounds showed marked anticoccidial activity in chickens. Structure-activity relationship was discussed and methylsulfinylethylthiamine showed the highest activity.View full abstractDownload PDF (741K) -
TETSUYA SUGA, KOKI NIKAWA, TAKEO HASHIMOTO, HISAYASU IZAYAMA1971 Volume 19 Issue 11 Pages 2235-2240
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAbsorption, distribution and excretion of tritiated p-biphenylmethyl-(dl-tropyl-α-tropinium) bromide (3H-BTTB) in the rat were investigated. After the intravenous injection of 3H-BTTB, half life of the radioactivity in blood was 7 min at first 30 min. Higher radioactivities were incorporated in kidney, liver, pancreas and spleen. Almost negligible radioactivity was seen in amniotic fluid or fetus. After the intramuscular injection of 3H-BTTB, 6.62% and 60.16% of the radioactivity were excreted in urine and feces, respectively, at 96 hr. The fact may indicate that 3H-BTTB is mainly excreted in bile. It may be suggested that these behaviors in biological disposition are attributed to have a large molecular weight and to be a quaternary ammonium compound.View full abstractDownload PDF (612K) -
MITSUYOSHI KAGEURA, YOSUKE OHKURA, TSUTOMU MOMOSE1971 Volume 19 Issue 11 Pages 2241-2246
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new colorimetric method for the determination of pyruvic acid is presented on the basis of a new color reaction of the acid with p-dimethylaminobenzaldehyde in dimethylsulfoxide solution in the presence of strong alkali. The method is selective for pyruvic acid among ketonic acids, but interfered by acetone, acetaldehyde, bilirubin, glucose, D-glucuronolactone and ascorbic acid.View full abstractDownload PDF (581K) -
SEIGORO HAYASHI, MITSURU FURUKAWA, YOKO FUJINO, KENZO SHIRAISHI1971 Volume 19 Issue 11 Pages 2247-2251
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of sodium ethoxycarbonylmethylthiosulfate and sodium phenacylthiosulfate with amine was examined and found to proceed through the intermediate formation of bisethoxycarbonylmethyldisulfide and phenacyldisulfide at the first step to give the corresponding thiooxamides.View full abstractDownload PDF (574K) -
SEIGORO HAYASHI, MITSURU FURUKAWA, YOKO FUJINO, HIROSHI OKABE1971 Volume 19 Issue 11 Pages 2252-2255
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBenzyl p-toluenethiosulfonate was found to form dibenzyltrisulfide with amine catalyst in the presence of water. On the other hand, α-benzylmercaptobenzyl p-toluenethiosulfonate was formed with amine catalyst in the presence of sulfur in 15% yield, without any dibenzyltrisulfide was obtained. The treatment with sodium hydroxide solution also gave benzylmercaptobenzyl p-toluenethiosulfonate in 49% yield. The mechanism of these reaction was presumed.View full abstractDownload PDF (501K) -
TETSUJI KAMETANI, MASATAKA IHARA1971 Volume 19 Issue 11 Pages 2256-2258
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCondenzation of 1-p-toluenesulfonylaziridine (V) with ethyl acetoacetate, followed by a ketalization of the resulting pyrrolidone (X), gave the ketal (XI), which was cleaved with sodium in liquid ammonia to give 3-acetyl-2-pyrrolidone ethylene ketal (II). Since this compound (II) had already been led to corydalactam (I), an alternative synthesis of corydalactam has been accomplished.View full abstractDownload PDF (395K) -
SADAO NISHIGAKI, KEITARO SENGA, FUMIO YONEDA1971 Volume 19 Issue 11 Pages 2259-2261
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 1, 3-dialkyl-6-amino-uracils with phosphorus oxybromide gave 1, 3-dialkyl-6-bromo-cytosines in good yields. The latter served as starting materials for several nucleophilic reactions.View full abstractDownload PDF (455K) -
HARUO SAIKACHI, HIROSHI MUTO1971 Volume 19 Issue 11 Pages 2262-2270
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive resonance-stabilized bisphosphoranes were prepared for the object of the future work. Preliminary examination was carried out in order to make clear the reactivity of the resonance-stabilized bisphosphoranes with the six aromatic monoaldehydes by the Wittig reaction. An unexpected ester exchange reaction of ethyleneglycol bischloroacetate (1) was discussed in the case of 9, 6-dioxa-2, 7-dioxoheptane-1, 8-bistriphenylphosphonium chloride formation.View full abstractDownload PDF (815K) -
KUNITOSHI YOSHIHIRA, MICHIKO TEZUKA, PANIDA KANCHANAPEE, SHINSAKU NATO ...1971 Volume 19 Issue 11 Pages 2271-2277
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of diospyrol, the anthelmintic principle of fresh fruits of Diospyros mollis GIRFF., was revised to I by the preparation of the derivatives shown in Chart 1 and by their spectral examinations especially by nuclear magnetic resonance (NMR) shown in Table I. The dried fruits, bark, and fresh roots were also examined and the presence of elliptinone (VI), mamegakinone (VII), and 4, 5, 8-trimethoxy-2-naphthaldehyde (XIII) besides triterpenoids, lupeol, lupenone, betulin, and taraxerol, was revealed.View full abstractDownload PDF (790K) -
KEIKI KOUNO, YO UEDA1971 Volume 19 Issue 11 Pages 2278-2283
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA solution of imidazole in dichloromethane developed blue color immediately by an addition of a solution of tetracyanoethylene in the same solvent at the temperature of lower than 0°. The color turned to yellowish brown when the temperature of the mixture was allowed to rise to higher than 0°. A mixing of both solutions at room temperature produced yellowish brown solution, directly. The mixture separated reddish brown crystals when it was stand at room temperature for about 30 min. The absorption maxima at 400 and 418 mμ of the crystals were proved to be attributable to 1, 1, 2, 3, 3-pentacyanopropenide anion, and this absorption spectrum was shown to be almost identical with that of the reaction mixture mixed at room temperature. 4(5)-Methyl-, 4(5)-phenyl- and 4, 5-diphenylimidazole gave similar results. The chemical structures of these crystals were clarified as imidazolium and substituted imidazolium 1, 1, 2, 3, 3-pentacyanopropenide from the results of elemental analyses, infrared spectra, nuclear magnetic spectra, titrations with sodium hydroxide solution, and from the detections of imidazole and imidazole derivatives on thin-layer chromatogram developed by a basic solvent.View full abstractDownload PDF (625K) -
MITSURU FURUKAWA, YOKO FUJINO, SEIGORO HAYASHI1971 Volume 19 Issue 11 Pages 2284-2288
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBiguanide derivatives were allowed to react with acetylacetone and benzoylacetone. Both of alkyl and arylbiguanides reacted with acetylacetone to give the corresponding 4, 6-dimethyl-2-alkyl or arylguanidinopyrimidine. On the other hand, arylbiguanides were found to exhibit chemical behaviors different from alkylbiguanides toward benzoylacetone. Two moles of arylbiguanides reacted with benzoylacetone to give 6-arylamino-4-amino-2-phenyl-2(6'-arylamino-4'-amino-2'-methyl-1', 2', -dihydro-s-triazinyl-2'-methyl)-1, 2-dihydro-s-triazine, though alkylbiguanides gave 6-methyl-4-phenyl-2-alkylguanidinopyrimidine under the similar condition. It was noted that the reaction of 1-methyl-1-phenyl-biguanide with benzoylacetone resulted in the formation of 6-methyl-4-phenyl-2-methyl-phenylguanidinopyrimidine without formation of any expected bisdihydro-s-triazine.View full abstractDownload PDF (532K) -
KAZUO KARIYONE, HISATOYO YAZAWA, MASANOBU KOHSAKA1971 Volume 19 Issue 11 Pages 2289-2293
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTomaymycin (2) and oxotomaymycin (3) are antibiotics isolated from Streptomyces achromogenes var. Tomaymycetics. The structure of tomaymycin (2) was determined by degradation reactions together with spectral analysis and by synthesis of the important derivative (8b) containing the basic skeleton of the antibiotic. The structure of oxotomaymycin (3) was also established by chemical correlation to the derivative (7a) of tomaymycin.View full abstractDownload PDF (592K) -
MITSUYOSHI KAGEURA, YOSUKE OHKURA, TSUTOMU MOMOSE1971 Volume 19 Issue 11 Pages 2294-2300
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour reaction products (I, II, III and IV) were separated in the color reaction of pyruvic acid with p-dimethylaminobenzaldehyde in an aqueous sodium hydroxide-dimethylsulfoxide solution at the reaction temperature of 40°or 60°, and their structures and roles in the colorimetric method of pyruvic acid determination previously presented were investigated. I was obtained from the reaction mixture resulted at the reaction temperature of 40°and determined as the trans form of p-dimethylaminobenzalpyruvic acid. The absorption spectral data showed that I was the sole coloring matter in the method of pyruvic acid determination. II, III and IV were produced in the reaction at 60°, and II and IV were purified as their methyl esters. They were characterized as 5-(p-dimethylaminophenyl)-isophthalic acid derivatives as shown in Chart 1, and proved not to be related to the coloration. The reaction pathways to form those products were also discussed.View full abstractDownload PDF (781K) -
GOH MIYAJIMA, YOSHIO SASAKI, MIYOKO SUZUKI1971 Volume 19 Issue 11 Pages 2301-2307
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNumerous carbon-13 chemical shifts of monosubstituted, meta- and para-disubstituted benzene derivatives as well as symmetrically and unsymmetrically substituted toluene and chlorobenzene homologs were measured to test the reliability of the simple sum rule from monosubstituted benzene derivatives. The chemical shifts of meta- and para-disubstituted benzene derivatives were examined with respect to the substituent constants σi and σπ.View full abstractDownload PDF (544K) -
KUNITOSHI YOSHIHIRA, MICHIKO TEZUKA, SHINSAKU NATORI1971 Volume 19 Issue 11 Pages 2308-2313
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-Methyljuglone (II), mamegakinone (III), isodiospyrin (IV), and bisisodiospyrin (V) were isolated from the roots of Diospyros lotus. (IV) and (V) were also isolated from the roots of D. morrisiana. The structure of (IV) was confirmed by the nuclear Overhauser effects observed in the methyl ether (IV'). Bisisodiospyrin (V) is a naphthoquinone tetramer corresponding to the symmetrical dimer of isodiospyrin (IV) linking at 2'- or 3'-position. The plants contain betulin, betulinic acid, oxyallobetulin, taraxerol, lupeol, and ursolic acid.View full abstractDownload PDF (675K) -
MASANORI KUROYANAGI, KUNITOSHI YOSHIHIRA, SHINSAKU NATORI1971 Volume 19 Issue 11 Pages 2314-2317
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree naphthoquinones, isodiospyrin (I), bisisodiospyrin (II), and 7-methyljuglone (IV), a new tetralone derivative named shinanolone (III) and four triterpenes, taraxerol, lupeol, betulin, and betulinic acid, were isolated from the roots of Diospyros japonica. The structure of shinanolone was elucidated to be 4, 8-dihydroxy-6-methyl-1-tetralone and the application of the dibenzoate chirality rule was attempted for the compound.View full abstractDownload PDF (528K) -
TETSUYA NAKAMURA, SHIZUMASA KIJIMA1971 Volume 19 Issue 11 Pages 2318-2324
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA four-step methylation of β-, γ-, and δ-tocopherol to α-tocopherol is described. All of the intermediates are isolated and characterized. The purities of methylated tocopherols are determined by quantitative gas liquid chromatography. The four steps are Mannich reaction, acetolysis, reductive cleavage, and reduction.View full abstractDownload PDF (819K) -
TATSUZO FUJII, YOSHIKO KOMATSU, MICHIE MUROFUSHI1971 Volume 19 Issue 11 Pages 2325-2330
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMore than 80% of the acetylcholinesterase present in porcine erythrocyte membrane could be released from it by repeated washing with hypotonic buffer, as was true in the case of bovine erythrocyte. Density-gradient centrifugation revealed that the released enzyme particles of either species of mammals have a similar density of about 1.07 which is significantly lower than that of the original stroma. It has phospholipid and cholesterol contents higher than those of the stroma. Introduction of dinitrophenyl residue to the outer surface of the erythrocyte membrane caused about 60% inhibition of the acetylcholinesterase activity in all of human, bovine and porcine erythrocytes. Penicillin bound to the erythrocyte membrane exerted almost complete inhibition of the enzyme activity in all cases. These results suggest that acetylcholinesterase of similar nature is present in a form of lipoprotein on the outer surface of the erythrocyte membrane, with a density lower than that of the main part of the membrane.View full abstractDownload PDF (666K) -
SEIJU KUBOTA, MASAYUKI UDA, MICHIKO OHTSUKA1971 Volume 19 Issue 11 Pages 2331-2336
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethylation of 3-α-pyridyl-1, 2, 4-triazoline-5-thione (II) with methyl iodide in alkaline solution gave 5-methylthio-3-α-pyridyl-1, 2, 4-triazole (III) and its N-methyl derivatives, 1-, 2-, and 4-methyl-5-methylthio-3-α-pyridyl-1, 2, 4-trizaole (IV, V and VI). The structures of these compounds were established by elemental analysis, spectral data and the identification with the compounds prepared by different methods. IV, V and VI were also produced by methylation of III with methyl iodide in alkaline solution. Methylation of III with dimethyl sulfate in alkaline solution or diazomethane in methanol also gave the same products. The ratios of the amount of IV : V : VI in the products were determined by nuclear magnetic resonance spectroscopy and it was found that IV was predominantly formed in every case.View full abstractDownload PDF (703K) -
YUJI NAKAHARA, TETSUKICHI NIWAGUCHI1971 Volume 19 Issue 11 Pages 2337-2341
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSd-N6-Demethyl lysergic acid diethlyamide (V) was synthesized by the following procedures. von Braun reaction of d-lysergic acid diethylamide (LSD) (I) gave d-N6-cyano-N6-demethyl LSD (II), followed by alkaline hydrolysis in dioxane to give mainly urea type compound (IV) together with a trace of V. The conversion of IV to V was achieved by treatment with sodium nitrite and tartaric acid. On the other hand, alkaline hydrolysis of II in MeOH gave isourea type compound (VI) and a small amount of V.View full abstractDownload PDF (563K) -
YASUHIRO YAMANE, MOTOICHI MIYAZAKI, NOBUYUKI YAMAJI, TADASHI OGASHIWA1971 Volume 19 Issue 11 Pages 2342-2348
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDecarboxylation of oxalacetic acid (OAA) by metal chelates was examined, using copper (II) as a metal and seven kinds of ligand, which forms N, N-coordinated five membered ring chelate, used were 6, 6'-dimethyl-α, α'-dipyridyl, 4, 4'-dimethyl-α, α'-dipyridyl, α, α'-dipyridyl, 5-nitro-ο-phenanthroline, ο-phenanthroline, 4, 7-dimethyl-ο-phenanthroline, and ethylenediamine. When the concentration ratio of dipyridyl to copper (II) was varied, 1 : 1 ratio of copper to dipyridyl effected the fastest decarboxylation rate of OAA, and the rate was faster than that by copper (II) ion alone. Effect of each ligand on the reaction rate was examined and the reaction rate fell in the order of α, α'-dipyridyl, ο-phenanthroline, and ethylenediamine ; 5-nitro-ο-phenanthroline, ο-phenanthroline, and 4, 7-dimethyl-ο-phenanthroline ; α, α'-dipyridyl, 6, 6'-dimethyl-α, α'-dipyridyl, and 4, 4'-dimethyl-α, α'-dipyridyl. When the acetate buffer concentration was 0.1M, the reaction rate was faster, the smaller the pKa, and greater the catalytic effect. When the buffer concentration was 1.0M, the above order did not hold. It was also revealed that steric effect of the ligand affected this reaction. The intermediate formed in this decarboxylation reaction was examined by the measurement of ultraviolet and infrared spectra, and by isolation of this intermediate, and formation of a mixed chelate compound of OAA, copper, and ligand was confirmed.View full abstractDownload PDF (728K) -
MASAHIRO NAGAI, OSAMU TANAKA, SHOJI SHIBATA1971 Volume 19 Issue 11 Pages 2349-2353
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(-) Cinenic acid was obtained by stepwise degradation of panaxadiol (I). The Rconfiguration of (-) cinenic acid (II) and its methyl ester (X) was established by the derivation from R-(-) linalool. Consequently, the absolute configuration at C(20) of panaxadiol was proved to be R.View full abstractDownload PDF (604K) -
SHOJIRO YURUGI, MASARU HIEDA, TOMIYOSHI FUSHIMI, MITSUMI TOMIMOTO1971 Volume 19 Issue 11 Pages 2354-2364
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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JUN MITSUI, MINORU KURODA, NOBUTAKA TSUNAKAWA, YASUMITSU TAKEYA1971 Volume 19 Issue 11 Pages 2365-2372
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMepyrizole (DA-398) was found to have the two crystalline forms of anhydride and dihydrate. Aqueous solution which contain more than 5 per cent of mepyrizole separate into two liquid layers at temperatures above 45°. It was found from the results of thermal analysis that crystal of mepyrizole dihydrate is transformed into anhydrous form at about 46°. Phase diagram of mepyrizole/water system was obtained by summarizing the results of solubility studies, hygroscopic equilibriums and thermal analysis. Such abnormalities in the vicinity of 46°can be explained as based on the transition between mepyrizole anhydride and dihydrate and the mutual solubility of mepyrizole anhydride and water. From the results of calorimetric analysis, the endothermic reaction given after the dissolution reaction is deduced to the hydration reaction of mepyrizole anhydride in solution. Consequently, the dissolution phenomena of mepyrizole anhydride can be explained as follows : mepyrizole anhydride [MP]solid first dissolves quickly in water as anhydride [MP]aqueous and then gradually changes into dihydrate [MP.2H2O]aqueous. [MP]solid→[MP]aqueous→[MP.2H2O]aqueousView full abstractDownload PDF (729K) -
KINZO NAGASAWA, TOSHIHARU YAMADA, AKIRA OGAMO1971 Volume 19 Issue 11 Pages 2373-2379
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reductive cleavage of sulfur containing organophosphorus compounds and its application to the analysis of organophosphorus pesticides were examined. Cidial, malathion, and dimethoate having a common structure (CH3O)2P(S)SR were treated by Raney nickel in ethanol. The non-phosphorus products characteristic to each of the original pesticides were formed, and they were identified with ethyl phenylacetate, diethyl succinate, and N-methylacetamide, respectively. Px which is a main phosphorus containing product common to these pesticides was identified with the phosphorus compound obtained by the same treatment of dimethyl dithiophosphate. The structure of Px and the reaction mechanism were discussed. It was also proved that this reaction afforded a new method to characterize this type of organophosphorus pesticides.View full abstractDownload PDF (693K) -
SHUNICHI YAMADA, MITSUYOSHI WAGATSUMA, YOSHIO TAKEUCHI, SHIRO TERASHIM ...1971 Volume 19 Issue 11 Pages 2380-2388
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of glycine ester with Cu (II) ion and other metal ions in a non-aqueous solution at room temperature resulted in the simultaneous formation of di-, tri-, and tetraglycine peptide esters. Each peptide ester was separated by column chromatography after carbobenzoxylation. Diketopiperazine was not formed in this reaction. Various reaction conditions were examined in detail.View full abstractDownload PDF (917K) -
SHIGEKO OZAKI, HIROTERU SAYO, MASAICHIRO MASUI1971 Volume 19 Issue 11 Pages 2389-2393
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Alkylhydroxylamines are shown to be easily oxidized to corresponding nitroso compounds with lead tetraacetate in benzene. The N-alkylhydroxylamines are found to react with equimolar lead tetraacetate and corresponding alkylnitroxides are detected during the oxidation. These results propose a mechanism in which lead tetraacetate acts as a hydrogen abstracting oxidant and the N-alkylhydroxylamines are oxidized to nitroso compounds via corresponding alkylnitroxides.View full abstractDownload PDF (554K) -
HIKARU OKABE, NORIKO KOSHITO, KOZO TANAKA, TOSHIO KAWASAKI1971 Volume 19 Issue 11 Pages 2394-2403
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS"Pharbitic acid" (I), the component glycosidic hydroxyfatty acid of pharbitin, was found to be a mixture of two minor and two major constituents, pharbitic acids A, B, C (II) and D (III). II and III were isolated by silica gel chromatography of their p-phenyl phenacyl esters and subsequent saponification. II, mp 120-129°, [α]D -51.4°, C44H78O26·10H2O, is composed of ipurolic acid, two moles each of D-glucose and L-rhamnose and one mole of D-quinovose, and III, mp 140-145°, [α]D -63.8°, C50H88O30·2H2O, has another mole of L-rhamnose. Oxidation of I with Na2Cr2O7 and treatment with AcONa in boiling Ac2O both followed by acid hydrolysis provided respectively 10-hydroxytridecan-2-one (VI) and 11-hydroxytetradec-2-enoic acid (VII) as the sole ether soluble product indicating that II and III are 11-O-oligosides of ipurolic acid. On oxidation with NaIO4 and subsequent acid hydrolysis, III provided D-quinovose, while II yielded none, and partial hydrolyses of I, II and III yielded equally monoglucoside (XI), [α]D -16.2°, C21H40O9·H2O, diglucoside (XII), mp 114-116°, [α]D -23.6°, C27H50O14·1/2 H2O, and rhamnodiglucoside (XIII), [α]D -25.7°, C33H60O18·H2O. On the basis of the above results together with those of gas chromatographic analyses of aglycones and component monosaccharides of the permethylates of II, III, XII and XIII, II and III are assigned the structures either one of IIa-c and IIIa-c, respectively.View full abstractDownload PDF (1018K) -
SEIGORO HAYASHI, MITSURU FURUKAWA, YOKO FUJINO, HIROSHI OKABE, TORU NA ...1971 Volume 19 Issue 11 Pages 2404-2409
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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AKIRA AKAHORI, FUMIO YASUDA, TAMETO OKANISHI1971 Volume 19 Issue 11 Pages 2409-2411
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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MASASHI TOMODA, MACHIKO TANAKA, NORIKO KONDO1971 Volume 19 Issue 11 Pages 2411-2413
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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HIROSHI TOMISAWA, HIROSHI HONGO, HIDEKI KATO, REIKO FUJITA1971 Volume 19 Issue 11 Pages 2414-2417
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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AKIE IJIMA, KIYOSHI TAKAHASHI1971 Volume 19 Issue 11 Pages 2417-2419
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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ITIRO YOSIOKA, KIMIKO MORIMOTO, KEIKO MURATA, HIROSHI YAMAUCHI, ISAO K ...1971 Volume 19 Issue 11 Pages 2420-2422
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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HIROSHI HIKINO, TAEKO TAKAHASHI, TSUNEMATSU TAKEMOTO1971 Volume 19 Issue 11 Pages 2424-2425
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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TATSUSHI MURAE, AKIHIKO SUGIE, TAKAHIKO TSUYUKI, TAKEYOSHI TAKAHASHI1971 Volume 19 Issue 11 Pages 2426-2428
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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SATOSHI OMURA, AKIRA NAKAGAWA, HARUKI YAMADA, TOJU HATA, AKIO FURUSAKI ...1971 Volume 19 Issue 11 Pages 2428-2430
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
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ITSUO YOSHIZAWA, KANNOSUKE FUJIMORI, MICHIYA KIMURA1971 Volume 19 Issue 11 Pages 2431-2432
Published: November 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (337K)
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