1) The derivatives of decanoylphenol, among the various decanoylbenzene derivatives, were found to have strong antifungal activity. 2) From the results obtained, it might be concluded that β-ketoaldehyde, pyrazole, and phenol groups are toxic toward some microörganisms.
1) Application of alkylmagnesium bromides respectively to 2-diethylamino-, 2-piperidino-, and 2-morpholino-methylcyclohexanone yielded the corresponding 1-alkyl-2-diethylamino-, -2-piperidino-, and -2-morpholino-methylcyclohexanols. The latter was converted to a series of esters by condensation with aromatic acid chlorides. 2) Application of acetyl or isovaleryl chloride or ethyl chlorocarbonate to 2-alkyl-(or benzyl)-2-dimethylaminomethylcyclohexanols yielded the corresponding esters. 3) Application of ethyl chlorocarbonate respectively to 1-alkyl-1-p-aminobenzoyloxy-2-dimethyl (or diethyl) aminomethylcyclohexanes gave the urethanes. β-Bromopropionyl ester was obtained by the application of β-bromopropionyl chloride to 1-ethyl-2-dimethyl-aminomethylcyclohexanol and condensation of dimethylamine to the ester yielded 1-β-dimethylaminopropionyloxy derivative.
Histamine was detected and quantitatively determined from “Samma-Sakuraboshi” (dried mackerel-pike), which caused food poisoning. The amount of histamine detected did not agree with the result of lethal dose test in animals. Chromatographic fractionation through alumina failed to show the presence of any toxic substance other than histamine (cf. Table III), but the presence was confirmed of a factor that cooperates with histamine.
Synergistic action of putrefaction amines with histamine was examined by the excised uterus (Magnus method) of a guinea pig and cat blood pressure methods. Each amine was added to the threshold of histamine and the action was observed. Synergistic action was observed in trimethylamine N-oxide, trimethylamine, agmatine (inhibitive in higher concentration), and choline by the Magnus method, and in trimethylamine N-oxide and phosphorylcholine by the cat blood pressure method (cf. Figs. 1-4).
Eighteen kinds of glycerol α, γ-diphenyl ethers, including 15 new compounds, were prepared and their pharmacological action was examined, together with comparison of these compounds with the corresponding glycerol α-monophenyl ethers. Of the glycerol α, γ-diethers of nitrogen-containing phenols, 1, 3-bis (o-aminophenoxy)-, 1, 3-bis (p-amino-phenoxy)-, 1, 3-bis (o-dimethylaminophenoxy)-, 1, 3-bis (m-dimethylaminophenoxy)-, and 1, 3-bis (p-dimethylaminophenoxy)-2-propanols possessed stronger muscle relaxing action and anticonvulsant action against electric shock than the corresponding glycerol α-monophenyl ethers. The muscle relaxing action of 1, 3-bis (m-dimethylaminophenoxy)-2-propanol was weaker than that of Myanesin but its anticonvulsant action was stronger than that of the latter. Its safety margin, LD50/ED50, is greater and its solubility in diluted hydrochloric acid is also greater. Of these compounds tested, quaternary ammonium salts were devoid of either action.
Aryl esters of p-aminosalicylic acid were prepared by the dropwise addition of thionyl chloride to a mixture of p-aminosalicylic acid and phenols, in benzene, in the presence of dimethylaniline. The melting points of the esters of p-aminosalicylic acid obtained are as follows: Phenyl ester, 145°; o-tolyl ester, 95°; m-tolyl ester, 136°; p-tolyl ester, 121°; o-methoxyphenyl ester, 139°; p-methoxyphenyl ester, 147°; p-chlorophenyl ester, 164.5°; o-bromophenyl ester, 131°; 4-bromo-2-methylphenyl ester, 168°.
As homologs of allithiamine, thiamine, or homothiamine β-hydroxyethyl disulfide (II or V) and thiamine monobenzoate (XVIII: R=COC6H5, R′=H) were synthesized. Acid or alkaline decomposition and reduction with cysteine of (II) were the same as those of allithiamine but its thermal decomposition differred from that of allithiamine in that thiamine-thiazolone (XIII) and thiochrome (XIV) were formed, and the formation of S-B1 (XV) was quite minute. Thiamine ethyleneoxymethyl disulfide (XVI) and di-and monoacetates and dibenzoate (XVIII) were synthesized but they all came as a syrupy or oily substances and could not be induced to crystallize.
By the catalytic vapor-phase reaction, N-alkylmorpholines were prepared from the corresponding N-alkyldiethanolamines. Examination of the reaction conditions, such as the kind of the catalyst used, temperature, and pressure, indicated that the yield of N-alkylmorpholines is the best when silica-alumina (coprecipitate) is used as the catalyst and the reaction carried out at 375-400° at an ordinary pressure. The respective yield was: Methyl, 33%; ethyl, 40.5%; isopropyl, 41%; butyl, 45%; phenyl, 67%. When diethanolamine is passed over silica-alumina at 400°, triethylenediamine is obtained in about 10% yield and the yield of morpholine becomes extremely small. Passage of a mixed vapor of morpholine and alcohol (methyl, ethyl, isopropyl, or butyl) over silicaalumina catalyst gives N-alkylmorpholine in about 30% yield.
Diosgenin, kryptogenin, and yamogenin are known as the sapogenins obtained from the plants of Dioscoreaceae but only diosgenin alone has been found in Dioscorea tokoro Makino. A small amount of crystals of m.p. 266°, [α]D: -49.6° (EtOH), was isolated from the rhizome of D. tokoro, besides diosgenin, and various reactions were carried out on this substance. As a result, it has been confirmed that this substance is an unknown iso-type trihydroxysteroidal sapogenin and was designated as tokorogenin.
1) In order to observe the effect of acclimatization, comparative examination of growth and development of the plant, yield of crop, and seasonal variation of santonin content was carried out during June 16 to October 1, 1953, on the second year growth of Artemisia kurramensis Qaz., grown from the seed obtained in January, 1952, from the plant cultivated at Kasukabe since 1951, and of the plant grown from the seeds of Pakistan origin (Table I). It was found that the second year growth also showed far better results in the acclimatized plot than in the Pakistan plot, the maximum of the yield of crop per 10 ares on air-dried basis and santonin content of the acclimatized plot being 163.2kg. (harvested July 1) and 1.98% (harvested August 1), respectively, and 77.2kg. (harvested August 1) and 1.47% (harvested July 1), respectively, in the Pakistan plot. 2) It was found that, although the first year growth of Artemisia kurramensis shows weak growth, small yield of crop, and low santonin content, its growth becomes suddenly active during the second year, and both the yield of crop and santonin content increase markedly (cf. Tables I and III). 3) The seasonal variation in santonin content of the third and fourth year growths of this plant showed approximately the same tendencies as that of the second year growth and the santonin content itself was no different from that of the second year growth (Table II). According to four cultivation experiments in the past, the santonin content reaches the maximum during the early part of September in the first year growth, and in July, especialy during the early part, in the second, third, and fourth year growths. They all seem to have no relation to the appearance of flower buds and such season is generally at the height of vegetative growth. 4) It was found that the plant survived longer after harvest when only one-half of the shoots was harvested rather than the whole shoot of one plant. 5) The first year growth, in the case where seedlings were brought up in the open air, gave better yield of crop and santonin content than that in the case where seedlings brought up in the glass house. 6) Detailed observations on the flowering and seed-setting of this plant revealed that it is self-sterile and is a short-day plant (cf. Table IV). 7) The plants cultivated with protection from rain druing October to January under plastic roof or in the glass house showed seed-setting but those left in the open air failed to show seed-setting. Such a fact is assumed to indicate the necessity of a dry atmosphere and a suitable temperature. 8) Suitable temperatures for the germination of pollens seem to lie in the range of 15-20° (cf. Table V). The pollens stored in a desiccator with drying agent retained germination power for about one month but those kept in natural state lost such a power in about six days.
Since glutamylcholine, whose synthesis had previously been reported, was found to have interesting physiological actions, synthesis of the ester of methionine and choline was attempted and the objective methionylcholine was obtained by four different routes. The ester thereby obtained was highly hygroscopic and was obtained as a crystalline hyperchlorate. The by-products obtained during the course of this synthesis were examined by paper chromatography.
1) Bromoacetal was reacted with 2-p-chlorobenzylpyridine, in the presence of sodium amide, and β-(p-chlorophenyl)-β-(2-pyridyl)-propionaldehyde diethylacetal was obtained. With or without the saponification of this acetal to the aldehyde, application of dimethylformamide and formic acid yielded Chlorprophenpyridamine. The yield in each step was better in the case of the acetal. In a similar manner, prophenpyridamine was obtained from 2-benzylpyridine. The use of N-formylpiperidine or N-formylpyrrolidine in place of dimethylformamide yielded 1-phenyl-1-(2-pyridyl)-3-(1-piperidyl)-or-3-(1-pyrrolidyl)-propane and their p-chloro derivatives. 2) Application of β-dimethylaminoethyl chloride to 2-p-chlorobenzylpyridine, in the presence of sodium amide, gave Chlorprophenpyridamine but the yield was extremely poor.
1) Reaction between diphenylarsinic acid and Zr.... was examined and it was clarified that they react at 4:1 ratio. 2) Starting with 4-nitrodiphenylarsinic acid, 4-(p-dimethylaminophenylazo)-diphenylarsinic acid was prepared and 4, 4′-bis (p-dimethylaminophenylazo) diphenylarsinic acid was prepared from p-nitroaniline. 3) The two azo dyes thereby obtained were used for the examination of spot tests for Zr.... and it was pointed out that these compounds could be used as the spot reagent for Zr.....
1) Spot reactions for F′ were examined with zirconium 4-(p-dimethylaminophenylazo)-and 4, 4′-bis (p-dimethylaminophenylazo)-diphenylarsinates. 2) Zirconium 4-(p-dimethylaminophenylazo)-diphenylarsinate was found to be better in selectivity and detection ability as spot reagent for F′ than the known zirconium p-dimethylaminophenylazophenylarsonate.
1) A series of p-nitrophenylazohydroxynaphthalenesulfonic acids were prepared and their use for spot tests of Mg.. was examined. 2) It was pointed out that 3-(p-nitrophenylazo)-4-hydroxynaphthalenesulfonic acid and 1-(p-nitrophenylazo)-2-hydroxynaphthalene-3, 6-disulfonic acid are of interest as the spot test reagent for Mg...
Acylation of the sodium salt of thiol-type thiamine (I) with p-nitrobenzoyl chloride or butyric anhydride yields S-acylthiamine (III) besides O, S-diacylthiamine (II). Heating of (III) with dil. hydrochloric acid results in the conversion of the acyl radical attached to the sulfhydryl group to the hydroxyl group and O-acylthiamine is formed.
By the condensation of p-sulfamylbenzoic acid and dipropylamine or by the catalytic reduction of the condensate of p-sulfamylbenzoic acid and diallylamine, the so-called Benemid, p-(dipropylsulfamyl)-benzoic acid, was obtained. Permanganate oxidation of p-(dipropylsulfamyl)-toluene resulted in oxidative decomposition and only p-toluenesulfonamide or p-sulfamylbenzoic acid was obtained. The same results were also obtained in the oxidation of p-(diallylsulfamyl)-toluene.
The chemistry of pyridazine is still not well known and most of its derivatives have been prepared by nuclear synthesis or by oxidation of phthalazine series. In order to study the substitution reaction in pyridazine series, oxygen-, nitrogen-, or sulfur-containing monosubstituted chloropyridazines and disubstituted derivatives of pyridazine were prepared. Catalytic hydrogenation of 3, 6-dichloropyridazine in aqueous methanolic ammonia solution, at ordinary pressure, gave pyridazine in 67.5% yield. Similarly, monosubstituted pyridazines were obtained by the hydrogenation of monosubstituted chloropyridazines.
From the ether extract of the root of Oenothera Lamarckiana Ser., a kind of sterol, tentatively designated as oenothera-sterol, was isolated as the non-saponifiable matter. Its molecular formula was determined as C29H50O. From the Liebermann-Burchard and Kariyone-Hashimoto reactions, formation of digitonide, and the Oppenauer oxidation the position of 3β-ol and the presence of one double bond at C5-C6 were confirmed. Melting point and optical rotation of the new sterol itself and its derivatives were compared with those of β-sitosterol, having the same molecular formula and similar properties and practically no difference was observed in all the values except the melting point of the acetate. It is therefore assumed that oenothera-sterol is identical with β-sitosterol which is most abundant in the fatty oil of higher plants.
The effects of S-ethyl-, S-propyl-, S-butyl-, and S-isoamylhomocysteines on the growth of Salmonella enteritidis 1891, Escherichia coli No. 1, and their methionine-requiring mutants were tested. None of the S-alkylhomocysteines could replace methionine and showed inhibitory effect on all the strains tested. Ethionine was the most effective, followed by S-isoamylhomocysteine, and all these were antagonized by methionine. However, no unequivocal relation between the length of alkyl chain and the inhibitory effects was obtained. Ethionine inhibited the methionine-utilization of both the parent and mutant strains of Sal. ent. and E. coli, and was competitively antagonized by methionine.
The lactone ring in tetrahydrosantonin and tetrahydrodesoxysantonin was hydrolyzed to hydroxy acids which were oxidized with chromic acid in pyridine and led respectively to the corresponding diketo acid, m.p. 146-149°, and keto acid, m.p. 99-98°. These were compared with those derived from alantolactone.
Reduction of the diazonium salt of 2-R-6-aminobenzothiazoles (R=Cl, N (CH3)2, N (C2H5)2, SCH3, SC2H5, and SC3H5) with SnCl2⋅2H2O and HCl gave their 6-hydrazino derivatives, whose condensation with aromatic aldehydes yielded a series of arylidenehydrazino compounds.
1) By the Condensation of various dipyridylformamidines with each of γ-picoline methiodide, ethiodide, propiodide, and isoamiodide, 21 kinds of quaternary salts of γ-aminovinylpyridine were prepared. 2) Ten kinds of styryl-type dyes were prepared by the respective condensation of aromatic aldehydes with γ-picoline methiodide and propiodide, and γ-ethylpyridine ethiodide.
Determination of tannic acid in Geranium (dried herb of Geranium nepalense) by methylene blue can be divided into three methods by the combination of the tannic acid solution used as the standard and the sample solution. Experimental results indicated that the determination by the combination of the sample solution and standard tannic acid solution was the best method. Using the same sample and taking X as the value determined with hide powder and Y as the value of determination by methylene blue, the relationship between X and Y may be indicated by X=Y+1.5×A/100/1.25×A/100 (where A is the purity of the standard tannic acid solution). Therefore, by the actual measurement of Y, tannic acid content approximating X can be obtained.
In the determination of tannic acid in Geranium (dried whole herb of Geranium nepalense Sweet), values obtained by the use of methylene blue was found to be larger than those obtained from the use of hide powder. In order to clarify the cause, the present experiments were undertaken and following items were clarified. 1) The purity of tannic acid used as the standard in the determination by methylene blue was found to be 88% and, therefore, substitution of 0.88 in place of A/100 in X=Y+1.5×A/100/1.25×A/100, given in the second paper of this series, and determination of Y will make it possible to assume the content of tannic acid from this equation with the value approximation that obtained by determination with the use of hide powder (Y indicates the value of hide determination by the use of methylene blue, X, the value of determination by the use of powder and A, the purity of tannic acid). 2) The determination values of aqueous solution of pure tannic acid by the two methods are equal. 3) The difference between the two determination values is due to non-tannic substance and its amount, calculated as tannic acid, is 2-8% of the determination value of Geranium by methylene blue. 4) Determination of Y, the value by the methylene blue determination, makes it possible to presume the value of X but the difference, Y-X, is comparatively small that the value of Y may be taken as the amount of tannic acid in Geranium.
There is no test rules for the determination of tannic acid in the Pharmacopoeia for Geranium (dried whole herb of Geranium nepalense) although tannic acid is assumed to be one of its effective principles. The experimental results revealed that there is a functional relationship between the Rb value and tannic acid content of Geranium (leaf blade) and that tannic acid content determined with methylene blue could be taken as the actual content of tannic acid. Based on these findings, seasonal variation of tannic acid content in the leaf blade of Geranium was examined in order to offer these data for Pharmacopoeia tests. The content of tannic acid was found to be the smallest during December to February in the same stock of plants growing in the same area, to increase gradually, and become the maximum during June to August, decreasing thereafter. By plotting this on a graph, a curve is obtained and with the measurement of the Rb value it would make it possible to detect the content of tannic acid (quality) of the plant, knowing the time of collection.
1) Procaine hydrochloride, sulfanilic acid, and p-aminobenzoic acid can be determined by the azotometry, by exactly the same method as that for sulfanilamide. 2) o-Nitroaniline and β-naphthylamine can be determined by azotometry by using potassium bromide as the accelerating agent and carrying out diazotization in 2-7 minutes. 3) Azotometric determination of aniline, p-toluidine, and p-aminosalicylic acid did not give a good result.
1) Isopropylamine and other amino compounds of R1R2CH-NH2 type are all posititive to ninhydrin reaction but their coloration is markedly poorer than those of α-amino acids and R-CH2-NH2 type amines. 2) A part of the reasons for the above was assumed to be the lowering of reactivity of NH2 group. Therefore, with the determination of the coloration, reactivity with nitrous acid was determined by azotometry, and the two were comparatively examined.
Application of heterocylic quaternary salts possessing methyl group in 2-position to the symmetric methine-oxonols and benzal compounds resulted in conversion to merocarbocyanine and styryl dyes. Unsymmetric carbocyanines possessing a pyridine ring and quinoline ring and styryl dyes possessing α-picoline methiodide undergo exchange of the parent nuclei by the application of a quinaldine salt, the pyridine ring exchanging with the quinoline ring in each dye. In a similar manner, application of thiobarbituric acid to methine-oxonol composed of barbituric and thiobarbituric acids and the benzal compound containing barbituric acid resulted in the exchange of barbituric acid with thiobarbituric acid. The same exchange of the parent nuclei was also found to occur in merocarbocyanines possessing a pyridine ring or barbituric acid.
Application of mono-, di-, or tri-bromoacetaldehyde or chloral respectively to the methiodide of α-picoline, 2, 6-lutidine, quinaldine, and 8-methylquinaldne, and quinaldine ethiodie, in glacial acetic acid at low temperatures yielded the corresponding 2-(ω-halo-methylvinyl)-type compounds.
Colistin, an antibiotic substance produced by a spore-forming bacillus discovered in Japan, was submitted to paper chromatography and the antibacterial chromatogram appearing on the paper placed on an agar plate of Escherichia coli N. I. H. J. was observed. As a result, it was seen that a large number of samples gave a clearly separated two images, and some gave a third image. The paper chromatography was carried out with Toyo Roshi No. 50, treated with 0.2M glycine buffer of pH 2.5, devloped with butanol, and three images were defined at Rf 0.53 (colistin-A), 0.38 (colistin-B), and 0.25 (colistin-C). Under the same conditions, polymixin-B gives the image at Rf 0.59. Further, separation of colistin-A and-B was effected by column chromatography by passing a mixture of colistin-A and-B through a column filled with silica gel saturated with 0.05M glycine buffer and developed with butanol.
The presence of leucine, threonine, and α, γ-diaminobutyric acid in the HCI-hydrolysate of colistin was confirmed by paper chromatography. These amino acids were further isolated pure by fractional precipitation with ethanol and by the use of ion exchangers, and confirmed by the following specific rotations: Leucine, [α]15D:+10.0°(c=0.3, H2O): threonine, [α]D11:-28.7°(c=1.9, H2O): α, γ-diaminobutyric acid, [α]D11:+8.9°(c=2.2, H2O). A fatty acid, possessing a molecular formula of C9H18O2, was isolated as a p-bromophenacyl ester, m.p. 59°, [α]D15: -24.0 (c=1.0, MeOH) from the oily portion that separated out during hydrolysis of colistin with hydrochloric acid. It was clarified that the properties of this ester were identical with the p-bromophenacyl ester of D-6-methyloctanoic acid.
Alkoxybenzaldehyde thiosemicarbazones were prepared and the antibacterial action against human type tubercle bacilli was tested in a Kirchner medium (OR, R=C4H9(o, p), C6H13(p), C8H17(o, p), C12H25(o, p), C14H29(o, p)). The size of alkyl group affected the antibacterial action which increased with the increased number of carbon in the alkyl and reached the maximum at C6 to C8, decreasing above that number. Antibacterial action of the para-compounds were better than the corresponding ortho-compounds.
o-Aminophenol dodecyl ether showed some antibacterial action in vitro against tubercle bacilli but it was found to be sparingly soluble in water that its water-soluble derivatives were sought. o-Guanylphenol dodecyl ether hydrochloride, sodium o-dodecyloxyanilinomethanesulfonate, and sodium o-dodecyloxyanilinoacetate were prepared for this purpose and these compounds showed some antibacterial action against the human type tubercle bacilli in Kirchner medium, the guanylphenol dodecyl ether having a positive radical showing the best efficacy. Therefore, butyl, octyl, dodecyl, and hexadecyl ethers of this series were prepared and their antibacterial action against human type tubercle bacilli was examined in Kirchner medium. The antibacterial action was found to increase with the increase in the number of carbon atoms in the alkyl chain, attaining the maximum at aroundC12 and decreasing thereafter. Comparison of butyl and dodecyl ethers of sodium o-alkoxyanilinomethanesulfonate also indicated that there is a same tendency in therelationship between the size of the alkyl group and antibacterial power.
Phloroglucinol and its methyl ethers undergo nuclear acylation when heated with acetic or propionic acid, in the presence of polyphosphoric acid, for 5-20 minutes on a boiling water bath, yielding 2, 4, 6-triacylphloroglucinol (I, II) and its monomethyl ethers (IV, V) from phloroglucinol and its monomethyl ether, 2, 4-diacyl-3, 5-dimethoxyphenol (VI, VII) from phloroglucinol dimethyl ether, and phloracylphenone trimethyl ether (IX, X) from phloroglucinol trimethyl ether.
α-Naphthol is nuclear-acylated when heated with 1 mole of carboxylic acid, in the presence of polyphosphoric acid, for 10-15 minutes on a boiling water bath and chiefly forms the 2-acyl compound with a small amount of 4-acyl compund. The yield becomes smaller when acids larger than propionic acid is used and 2-acyl compound practically the only product. Application of 2 moles of glacial acetic acid to α-naphthol or 1 mole to 2- or 4-acetyl-α-naphthol yields 2, 4-diacetyl-α-naphthol. α-Naphthyl esters easily undergo conversion by polyphosphoric acid to form 2- and 4-acyl-α-naphthol and in this case, also, the yield gradually decreases with esters of acids above propionic acid. Moreover, the chief product in this case is 2-acyl-α-naphthol. α-Naphthyl capronate did not undergo conversion.
1) Glucosamine hydrochloride was completely deaminated with silver nitrate and paper chromatography of the deamination product revealed that under the present conditions of deamination, presence of glucose, mannose, mannose, or arabinose could not be detected. 2) From the deamination product, chitose was isolated as its diphenylhydrazone. Periodate oxidation of chitose consumed 1 mole periodic acid but did not form either formic acid or formaldehyde. 3) High pressure, catalytic reduction of the deamination product gave 2, 5-anhydro-1, 6-ditosyl-D-mannitol. 4) From the foregoing experimental results, it was confirmed that the chitose formed by the deamination of glucosamine is 2, 5-anhydro-D-mannose.
Cardiotonic glycoside in the leaves of domestic Nerium odorum Soland (Apocyanaceae) was examined and adynerin, m.p. 220-223°, was isolated. There were some indications for the presence of oleandrin-like substance and a glycoside with a large polarity and possessing gitoxigenin- or oleandrigenin-series substance as the genin.
Many reports have indicated that numerous rules can be established as to the relationship detween the chemical structure and activity of curariform substanes. Pharmacological examination of the 20 kinds of compounds of this series synthesized revealed the following results. 1) It is a fact that the distance between the quaternary nitrogens is about 15°A but it was found that some variation appears by the manner of the binding bridge. 2) It was experimentally recognized that the activity is stronger when the nitrogencontaining ring is saturated than when unsaturated. 3) The rule that the activity is stronger when there is a methoxyl group in the nitrogencontaining ring, than when it is a hydroxyl or when there is no substituent was developed further to show that the activity is stronger in one with a methoxyl group than a methylenedioxy group, and in one with a larger number of the methoxyl groups. 4) No report has appeared to date regarding stereoisomers but the present experiments revealed that there were no marked differences in stereoisomers as to activity or lethal dose.
Taraxerol (tiliadin, alnulin, or skimmiol) was isolated from the leaves of Pieris japonica D. Don. (Ericaceae) and Myrica rubra Sieb. et Zucc. (Myricaceae). This has shown that taraxerol is distributed in six families (Betulaceae, Tiliaceae, Compositae, Rutaceae Fricaceae, and Myricaceae), seven genera, and nine species of plants. It is presumed that taraxerol, belonging to the β-amyrin series, is rather widely distributed in the plant world.
Myanesin was successfully obtained by allowing calcium monoglyceroxide to absorb carbon dioxide in an anhydrous state, in the presence of excess of glycerol and o-cresol, with subsequent heating to a high temperature. This method of preparation is more simple of procedures and more economical than the existing general method starting with glycerol α-monochlorhydrin.
Four kinds of nitroquinolines, possessing the nitro radical in the benzene portion, were reduced by hydrazine-liquid ammonia solution and the correspondiog aminoquinolines were obtained with over 80% yield.
Analyses of anions by paper chromatography was utilized in the systematic analysis of usual ions. Each group precipitated by barium nitrate, zinc acetate, or silver nitrate, was directly spotted on a filter paper and developed with a mixed solvent of AcOEt: acetone: 2N HCl (1:2:1) for barium salts, MeOH: N NH4OH (1:1) for zinc salts, and acetone: 28% NH4OH (3:1) for silver salts. The separability in this case was approximately equal to that obtained through the use of sample solutions. Of the four ion group, SO4--, IO3-, Fe(CN)6----, and S--, and I- failed to move and stayed in the original spot, but there was no inconvenience in its separation and detection.
In preparing sulfanilamide derivatives by the hydrolysis of the carbonyl derivatives of sulfanilamides, the use of an aqueous solution of the hydroxides of alkali earth metals as the hydrolyzing agent was found to give the objectives in a good yield without liberating the basic residue attached to the sulfanilyl radical and preventing occurrence of other side-reactions.
Dibucaine and Pantocaine are often used for lumbar anesthesia in surgical operations but these sometimes cause death. From the point of forensic chemistry, separatory detection of these compounds from their mixture from spinal fluid was carried out by paper chromatography.