The oxime of artemisia ketone is smoothly converted to the pyrazole derivative by sodium nitrite and acetic acid in CHCl3. The structure of the pyrazole was found by x-ray structural analysis. The PMR and13C NMR spectra were interpreted using two-dimensional1H−13C NMR (COSY, COLOC).
The results are given of the GLC analysis on a capillary column of the essential oils of two species of wormwood close in morphological characteristics growing in Kazakhstan: Artemisia radicans A. Kuprijanov and A. frigida Willd., fam. Asteraceae.
The essential oil of an endemic (Kazakhstan) species of Artemisia filatovae, A. kurpijanov sp. nov. (Filatov wormwood), is analyzed by gas chromatography on a capillary column with preliminary separation into fractions using adsorption chromatography on aluminum oxide. The components of A. filatovae essential oil differ from those of A. glabella Kar. et Kir. and A. obtusiloba Ldb.
The results are given of the gas-chromatographic analysis in a nonpolar capillary column, after preliminary separation by means of adsorption chromatography on alumina, of samples of the essential oils of three populations of the endemic speciesArtemisia glabella Kar. et Kir. (Asteraceae) of Kazakhstan. The complex component composition of the samples of essential oils was practically independent of the conditions of the growth site. The results obtained witness a chemosystematic difference betweenA. glabella andA. obtusiloba.
It has been established that, in spite of different ecological conditions of the growth of the endemic speciesZiziphora vychodceviana, Z. pedicellata, andZ. persica, they are characterized by identical biosyntheses of terpenoids and differ by the ratio of the main components of their essential oils.
It has been established that, in spite of different ecological conditions of the growth of the endemic speciesZiziphora vychodceviana, Z. pedicellata, andZ. persica, they are characterized by identical biosyntheses of terpenoids and differ by the ratio of the main components of their essential oils.
A new terpene ketone which has been called dehydroelsholtsia ketone has been isolated from the essential oil ofElsholtzia ciliata (Thumb.) Hyl. The structure of dehydroelsholtzia ketone as 3-methyl-2-(3-methylbut-2-enoyl)furan has been proposed on the basis of a study of its IR, PMR, mass and13C spectra and has been confirmed by its conversion into elsholtzia ketone.
Paeonia anoma/a L. --Ural peony --is a perennial herbaceous plant of the Paeoniaceae family.The whole plant contains essential oils.The essential oil from the roots of the Ural peony gathered in Western Siberia has shown a high antimicrobial activity [1], which has served as a basis for the investigation of its chemical composition.The essential oil was obtained from the comminuted roots by steam distillation, by distillation with superheated steam, and by distillation with steam from the previously ground roots.Since the essential oil dissolves in water, it was collected in a receiver containing diethyl ether.After drying with anhydrous sodium sulfate and evaporation of the ether, the essential oil consisted of a yellowish transparent liquid with a sharp odor and a burning taste.The yield was 0.55-1.70%(depending on the method of isolation).Constants: d2o 20 1.6240; nD20 1.5355-1.5394.Gas-liquid chromatographic analysis of the essential oil showed that, regardless of the method used for its isolation, it consisted essentially of two components and contained no substances of terpene structure.Of the five components present in minor amounts and not in total exceeding one per cent, we isolated substance (I) with n~ 1.5450, having a smell of almonds.IR spectrum (cm-I: 703, 2603, 3026, 3061, 3090 (monosubstituted benzene ring), 1665, 2740 (-C.I4o).These characteristics correspond to benzaldehyde.Substance (II) was identified as methyl benzoate: nD 2° 1.5167.IR spectrum: 1243, 1671 (-O-C~--~O), 712, 741, 1603, 3024, 3073, 3087 (C6H5-).The main component of the essential oil was methyl salicylate (III) nD20 1.5360; (t202° 1.1610.IR spectrum, cm -I, 1615 (C6H4-), 1250, 1678 (-O-C~---O), 3190 (-OH).The identification was confirmed by its PMR spectrum and by the formation of salicylic acid (mp 158-159°C).Substance (IV) was p-hydroxybenzaldehyde: nD 2° 1.5628.IR spectrum, cm-l: 1580 (C6H4-), 1668, 2755 (H-C~O), 3150 (-OH, broad band).Thus the esential oil of the roots of the Ural peony contained methyl salicylate (88 %), p-hydroxybenzaldehyde (11%), benzaldehdye (0.2 %), and methyl benzoate (0.1%), and also 13-phenylethyl alcohol (0.i %) and thymol (0.1%), which were identified with the aid of GLC by the addition of the authentic substances to the essential oil.The results that we obtained differ to some degree from those in the literature.GLC was performed on a Chrom-4 instrument with a 3 mm × 0.35 m column, containing 15% of PEGA on Celite 545, 0.20-0.25 mm; argon, 25 ml/min; programming from 70 to 195°C at 2°C/rain.The substances were isolated on a UKh-2 instrument with a 7 mm × 0.27 m column, INZ-600 refractory brick modified with polyvinylpyridine, 0.25-0.31mm; PEG --20.25%.Temperature 190°C.IR spectra were taken on a UR-20 spectrometer, and PMR spectra on Tesla 487.80 MHz spectrometer.
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A new terpene ketone which has been called dehydroelsholtsia ketone has been isolated from the essential oil of (Thumb.) Hyl. The structure of dehydroelsholtzia ketone as 3-methyl-2-(3-methylbut-2-enoyl)furan has been proposed on the basis of a study of its IR, PMR, mass andC spectra and has been confirmed by its conversion into elsholtzia ketone.
It has been established that the essential oils ofTanacetum boreale andAjania fastigiata contain as their main components 3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran and its acylated and oxidized derivatives.