Alkaloids of the Australian Rutaceae: Pentaceras australis Hook. F. II. Identification of 5-Methoxycanthinone

1952 ◽  
Vol 5 (3) ◽  
pp. 563
Author(s):  
ER Nelson ◽  
JR Price
Keyword(s):  
Carboxylic Acid ◽  
Potassium Permanganate ◽  
Methoxyl Group ◽  
Hydroxy Compound ◽  
Lactam Ring

The alkaloid C15H10O2N2, present in the bark of Pentaceras australis Hook. f., has been shown to be 5-methoxycanthin-6-one. It is oxidized by potassium permanganate to β-carboline-1-carboxylic acid and its lactam ring may be opened by alkali to give a β-carbolylmethoxyacrylic acid which readily recyclizes to the alkaloid. The position of the methoxyl group is demonstrated by demethylation and condensation of the resulting hydroxy-compound with o-phenylenediamine to give a hydroxyquinoxaline. Attempted hydrogenation of the alkaloid or the derived methoxyacrylic acid led to elimination of methoxyl.

scholarly journals DIRECT OXIDATION OF EUGENOL USING A PERMANGANATE

Molekul ◽  
2009 ◽  
Vol 4 (1) ◽  
pp. 48
Author(s):  
Reinner Ishaq Lerrick
Keyword(s):  
Carboxylic Acid ◽  
Viscous Liquid ◽  
Potassium Permanganate ◽  
Oxidation Reactions ◽  
Direct Oxidation ◽  
Polar System ◽  
Modified Method ◽  
Vicinal Diol ◽  
Important Intermediate

Direct oxidation of eugenol has been done using potassium permanganate. This research attempts to produce benzyl carboxylic acid, an important intermediate reactant for isoflavone synthesis, directly by breaking the p bond of allillic group attached to eugenol. The oxidation procedures were adopted from Wahyuningsih and Kusumaningsih anetol oxidation reactions. There were three modifications done i.e. one polar system of the oxidation environment, variation of time of reflux and temperature. Eugenol was firstly diluted in water by converting to its salt type and then oxidized using KMnO4 at 75 oC for 4 hours. The expected acid was separated by acidifying using sulfuric acid.The result showed that direct oxidation of eugenol using modified method of Wahyuningsih gave only a vicinal diol which undergoes polymerization into product in 80% yield with 83% purity. However, variation of time of reflux of Wahyuningsih method showed the same result with Kusumaningsih method as brown oily viscous liquid. The product was only 38% purity.

Alkaloids of the Australian Rutaceae: Melicope fareana. II. Preliminary Examination of Melicopine, Melicopidine, and Melicopicine

1949 ◽  
Vol 2 (2) ◽  
pp. 255
Author(s):  
WD Crow ◽  
JR Price
Keyword(s):  
Oxidation Products ◽  
Methoxyl Group ◽  
Hydroxy Compound ◽  
Alcoholic Alkali ◽  
Methylenedioxy Group ◽  
Alkoxyl Group ◽  
Preliminary Examination ◽  
Oxygen Atoms

Four of the five oxygen atoms in the alkaloids melicopine, melicopidine, and melicopicine are present as alkoxyl groups, either methoxyl or methylenedioxy. In each alkaloid one of the methoxyl groups is remarkably sensitive to hydrolysis by acids. The resulting hydroxy compound is an alcohol, or more likely, an unreactive phenol. The methylenedioxy group in melicopine and melicopidine is attacked by alcoholic alkali and replaced by an hydroxyl and an alkoxyl group. The resulting phenols still contain the easily hydrolysed methoxyl group, the loss of which gives rise to a series of dihydroxy compounds. A number of acidic oxidation products is described.

Attempts at the synthesis of 11-methoxysubstituted benzo[c]phenantridines

1985 ◽  
Vol 50 (4) ◽  
pp. 861-868 ◽  
Author(s):  
Jan Šmidrkal ◽  
Jiří Holubek ◽  
Jiří Šlanger ◽  
Jan Trojánek
Keyword(s):  
Carboxylic Acid ◽  
Methoxyl Group ◽  
Carboxyl Group ◽  
Nitrobenzoic Acid ◽  
Multistep Synthesis

Experiments aimed at the synthesis of so far unknown 11-methoxybenzo[c]phenanthridines (IIa,b,c) are described. In the first approach 2,3,7,8-tetramethoxybenzo[c]phenanthridine-11-carboxylic acid (IIIb) was synthesized using a procedure for the preparation of 2,3,7,8-bis-methylenedioxybenzo[c]phenanthridine-11-carboxylic acid (IIIa). Attempts to convert the carboxyl group of these acids to the methoxyl group were not successful. In the second approach 3-methoxy-6,7-methylenedioxy-l-methylaminonaphthalene (XX) was prepared from l-(3,4-rnethylenedioxyphenyl)-2-propanone (IX) by a multistep synthesis. On acylation of the product with 2,3-dimethoxy-6-nitrobenzoic acid and subsequent hydrogenation N-(3-rnethoxy-6,7-methylenedioxynaphth-l-yl)-N-methylamide of 6-amino-2,3-dimethoxybenzoic acid (XXII) was obtained. The attempts at its cyclization according to Pschorr were unsuccessful.

Alkaloids of the Australian Rutaceae: Pentaceras australis Hook. F. I. Isolation of the Alkaloids and Identification of Canthin-6-one

1952 ◽  
Vol 5 (2) ◽  
pp. 387 ◽  
Author(s):  
HF Haynes ◽  
ER Nelson ◽  
JR Price
Keyword(s):  
Carboxylic Acid ◽  
Acrylic Acid ◽  
Trans Isomer ◽  
Total Yield ◽  
Forest Tree ◽  
Ring System ◽  
Root Bark ◽  
Mature Trees ◽  
Plant Kingdom ◽  
Lactam Ring

Three alkaloids, with molecular formulae C14H8ON2, C15H10O2N2, and C15H10OSN2,, have been isolated from the ram-forest tree Pentaceras australis Hook. f. All three are present in the bark of mature trees, the total yield of alkaloids varying from c. 0.2 per cent. (branch bark) to c. 1 per cent. (root bark). The wood contains 0.2 per cent. of a mixture of two of the alkaloids, C14H8ON2 and C15H10OSN2, while the leaves contain less than 0.01 per cent. of a mixture in which the alkaloids C14H8ON2 and C15H10O2N2 are present.The alkaloid C14H8ON2 is shown to be representative of a ring system not previously found In the plant kingdom. It is canthm-6-one (II). The principal reactions on which this structure is based are (a) oxidation of the alkaloid to β-carboline-1-carboxylic acid and (b) the reversible opening of a lactam ring with alkali to give cis-2-(1'-β-carbolyl) acrylic acid (III) which may be transformed to the trans-isomer from which the alkaloid is not regenerated. Other reactions of the alkaloid support the canthinone structure. Among the compounds described is a dihydro-derivative (XI) of the parent base canthine

Alkaloids of the Australian Rutaceae: Pentaceras australis Hook. F. III. Identification of 4-Methylthiocanthin-6-one

1952 ◽  
Vol 5 (4) ◽  
pp. 768 ◽  
Author(s):  
ER Nelson ◽  
JR Price
Keyword(s):  
Carboxylic Acid ◽  
Hydrochloric Acid ◽  
Acrylic Acid ◽  
Absorption Spectra ◽  
Acid Chloride ◽  
Ethyl Esters ◽  
Methyl Mercaptan ◽  
Malonic Ester ◽  
Alcoholic Alkali ◽  
Lactam Ring

The alkaloid C15H10OSN2 occurring in the bark of Pentaceras australis Hook. f. is shown to be 4-methylthiocanthin-6-one. The lactam ring is opened by alcoholic alkali giving 2-methylthio-2-(1'-β-carbolyl)acrylic acid, followed by the elimination of methyl mercaptan and recyclization to 4-hydroxycanthin-6-one. Confirmation of the relation- ship of the alkaloid to canthinone is provided by (i) the ultraviolet absorption spectra, (ii) the formation of methyl mercaptan and 4,5-dihydrocanthine by treatment with zinc and hydrochloric acid, and (iii) the formation, by treatment with Raney nickel, of canthinone, 4,5-dihydrocanthinone, or the methyl or ethyl esters of β-carbolylpropionic acid, depending on the conditions employed. The alkaloid has been synthesized from β-carboline-1-carboxylic acid by conversion of the acid chloride with malonic ester, followed by cyclization, to 4-hydroxycanthinone, thence to 4-chlorocanthinone which with potassium methyl mercaptide yields 4-methylthiocanthinone. The low basicity of the alkaloid is discussed, particularly in relation to the basicity of 4-methoxy- canthinone.

A potassium permanganate fixative for membranes in sections

1990 ◽  
Vol 48 (3) ◽  
pp. 722-723
Author(s):  
Jindan Song
Keyword(s):  
Potassium Permanganate ◽  
Cultured Cells ◽  
Calf Serum ◽  
Trisodium Citrate ◽  
Membrane System ◽  
Adenocarcinoma Cell Line ◽  
Mouse Embryo Fibroblast ◽  
African Green Monkey Kidney ◽  
Adenocarcinoma Cell ◽  
Green Monkey

Potassium permanganate has been used as a fixative for the botanical specimen and membrane system in thin section by Glauert (1975). A new potassium permanganate fixative ( Trisodium citrate 60mM, Potassium chloride 25mM, Magnesium chloride 35mM, and Potassium permanganate 125mM ) for localizing membranous system in whole_mount cultured cells with standard trasmission electron microscopy and phase_contrast microscopy has been developed). Here, we report that using this new potassium permanganate fixative for membranous system in sections.Cultured cells, CV_1 (African green monkey kidney epithelial cells), Balb/c 3T3 ( Mouse embryo fibroblast ) and MCF_7 (Human adenocarcinoma cell line) were used for this study. All cells were grown on 35mm plastic dishes in DME medium containing 5% calf serum at 37 c with 100% humidity and 5% CO2. Using the potassium permanganate fixative to fix the cells for about 7 minutes. After fixation, the cells were dehydrated in a graded series of ethanol.

Etching of LLDPE and LLDPE/HDPE blends

1996 ◽  
Vol 54 ◽  
pp. 200-201
Author(s):  
M. S. Bischel ◽  
J. M. Schultz
Keyword(s):  
Potassium Permanganate ◽  
Morphological Features ◽  
Narrow Fraction ◽  
Potassium Permanganate Solution ◽  
Commercial Applications ◽  
Microscopy Techniques

Despite its rapidly growing use in commercial applications, the morphology of LLDPE and its blends has not been thoroughly studied by microscopy techniques. As part of a study to examine the morphology of a LLDPE narrow fraction and its blends with HDPE via SEM, TEM and AFM, an appropriate etchant is required. However, no satisfactory recipes could be found in the literature. Mirabella used n-heptane, a solvent for LLDPE, as an etchant to reveal certain morphological features in the SEM, including faint banding in spherulites. A 1992 paper by Bassett included a TEM micrograph of an axialite of LLDPE, etched in a potassium permanganate solution, but no details were given.Attempts to use n-heptane, at 60°C, as an etchant were unsuccessful: depending upon thickness, samples swelled and increased in diameter by 5-10% or more within 15 minutes. Attempts to use the standard 3.5% potassium permanganate solution for HDPE were also unsuccessful: the LLDPE was severely overetched. Weaker solutions were also too severe.

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