GAS–LIQUID CHROMATOGRAPHY OF TERPENES: XV. THE VOLATILE OIL OF MENTHA ARVENSIS VAR. GLABRATA RAY

1966 ◽  
Vol 44 (17) ◽  
pp. 2015-2022 ◽  
Author(s):  
E. von Rudloff ◽  
F. W. Hefendehl

The volatile oil of the North American wild mint (Menthaarvensis L. var. glabrata) was found to consist mainly of d-pulegone (80–90%) and smaller amounts of α-pinene, β-pinene, sabinene, limonene, 1,8-cineole, 1-octen-3-ol, menthone, isomenthone, piperitone, cis- and trans-pulegone oxide, and piperitenone. Trace amounts of γ-terpinene, menthofuran, β-caryophyllene, and ε-, δ-, and γ-cadinene were also isolated, and camphene, p-cymene, terpinolene, sabinene hydrate, isopulegone or its stereoisomer, β-elemene, and α-terpineol were tentatively identified. A labile autoxidation product of pulegone was also detected.A study of the seasonal variations in the oil composition showed that significant changes in the quantitative composition occurred only in very young plants. The maximum yield of oil was obtained at the start of flowering. Practically no variation in the composition of the oil was recorded for plants from different localities.


Author(s):  
N. S. Kuzmina ◽  
S. V. Portnova ◽  
E. L. Krasnykh

Objectives. The study aims to identify the optimal choice of an effective catalyst for the esterification of malic acid to produce esters of high purity. Methods. To determine the qualitative and quantitative composition of reaction masses, the following analysis methods were used: mass-spectroscopy (using FinniganTrace DSQ device with NIST 2002, Xcalibur 1.31 Sp 5 database) and gas–liquid chromatography (using the Kristall 2000M software and hardware complex). Results. Esters of malic acid and butyl alcohol of normal structure were synthesized using the following catalysts: sulfuric, orthophosphoric, p-toluenesulfonic acid, Amberlyst 36 Dry, Amberlyst 36 Wet, KU-2-FPP, and KIF-T. The obtained products were analyzed by gas–liquid chromatography. The structure of the products was confirmed by mass spectrometry. Schemes for the formation of byproducts are proposed. The yields and purity of the malic acid butyl esters obtained using different catalysts were evaluated. The results show that the heterogeneous catalyst Amberlyst 36 Dry is optimal for obtaining a pure malic acid ester with a maximum yield. Conclusions. The results show that during the esterification of malic acid with butyl alcohol of normal structure, byproducts, such as esters of fumaric and maleic acids, are formed using different catalysts. An accumulation of byproducts occurs as a result of reactions of dehydration of malic acid or its ester. The results also show that the number of byproducts is almost independent of the catalyst, with the exception of sulfuric acid. The Amberlyst 36 Dry catalyst provides an optimal ratio between conversion and selectivity for malic acid dibutyl ester production. 



1967 ◽  
Vol 45 (9) ◽  
pp. 1703-1714 ◽  
Author(s):  
E. Von Rudloff

The leaf oils from white and black spruce obtained from different locations in Western and Eastern Canada, Michigan, and Minnesota, have been analyzed by gas liquid chromatography. Both species were found to have a remarkably consistent and distinctive distribution pattern of the leaf oil terpenes. The quantitative variations encountered in samples of the same species from different populations are relatively small and ecological differences are not found to affect the leaf oil composition. Hence, analysis of spruce leaf oils appears to be highly suitable for a study of introgression and hybridization.



1995 ◽  
Vol 58 (10) ◽  
pp. 1147-1149 ◽  
Author(s):  
RASHA K. DAOUK ◽  
SHAWKY M. DAGHER ◽  
ELSA J. SATTOUT

The volatile oil of the Lebanese Za'atar (Origanum syriacum L.) was characterized for its thymol and carvacrol content using gas-liquid chromatography. These two compounds constituted the major components of the oil and were present in equal proportions of 30% in the volatile oil extracted from the leaves and shoot tips of the Origanum plant during the preflowering stage. The percentage of carvacrol in the essential oil increased to 62% after flowering and maturation, while the concentration of thymol decreased to 14%. Origanum oil extracted from plants collected during midseason was evaluated for its antifungal activity against Aspergillus niger, Fusarium oxysporum, and Penicillium species. The oil exhibited strong inhibitory action against the three fungi tested. The minimum inhibitory concentration (MIC) of the oil was found to be 0.1 μl/ml of yeast extract sucrose broth for the fungi tested.



1961 ◽  
Vol 39 (6) ◽  
pp. 1200-1206 ◽  
Author(s):  
E. von Rudloff

The complete analysis of the neutral volatile oil of the leaves of Eastern white cedar (Thujaoccidentalis L.) by means of gas–liquid chromatography was attempted. The mixture of terpenes was resolved into 28 monoterpenoid components and the major ones were isolated in 5- to 20-mg amounts. Comparison of infrared spectra and retention times with those of authentic specimens led to the positive identification of d-α-pinene, camphene, sabinene, d-limonene, p-cymene, γ-terpinene, l-fenchone, l-α-thujone, d-isothujone, camphor, and bornyl acetate. α-Thujene, β-pinene, myrcene, 1,8-cineole, terpinolene, and terpinen-4-ol were tentatively identified. The percentage composition of a commercial sample of the oil and of one obtained from a tree grown in Saskatoon was determined. The latter oil contained 7.0 to 7.5% of sesquiterpenoid components, which were resolved into four peaks on polyester columns at 180 °C.



1968 ◽  
Vol 46 (5) ◽  
pp. 679-683 ◽  
Author(s):  
E. Von Rudloff

The major components of the leaf oil of the Ashe juniper were found to be d-camphor (42.1 %), d-bornyl acetate (22.5%), d-limonene (8.4%), tricyclene (4.8%), d-camphene (4.4%), d-borneol (2.9%), p-cymene (2.8%), d-α-myrcene (1.8%), d-α-pinene (1.7%), and d-camphene hydrate (1.5%). This appears to be the first time that the latter alcohol has been isolated from a natural source. Smaller amounts of linalool, carvone, elemol, and traces of trans-2-methyl-6-methylene-3,7-octadien-2-ol were also identified. Several alcohols having terminal methylene groups were isolated in trace amounts.The monoterpenes found in this oil are not typical for the genus Juniperus and this result offers a unique chemical approach to the study of introgression of the Ashe juniper with other juniper species.





1979 ◽  
Vol 62 (6) ◽  
pp. 1333-1337
Author(s):  
Kalyan G Raghuveer ◽  
Venkatesa S Govindarajan

Abstract Simple and definitive thin layer chromatographic methods are described for the detection of admixtures of Curcuma longa with Curcuma aromatica at the 5% levels. The tests are performed on hexane extracts, thus avoiding distillation of the volatile oil, and are based on the separation of high boiling sesquiterpene compounds by hexane or benzene. Chromatograms are sprayed with vanillin-sulfuric acid or Gibbs reagent to give distinct spots for C. aromatica which are absent from C. longa. Gas chromatography of the extracts also distinguishes the admixtures through a late-eluting peak for C. aromatica.





1969 ◽  
Vol 47 (11) ◽  
pp. 2081-2086 ◽  
Author(s):  
E. von Rudloff ◽  
V. K. Sood

The volatile leaf oil of the local common juniper was found to consist mainly of α-pinene (73 to 83%) and smaller amounts (0.5 to 5%) of β-pinene, 3-carene, myrcene, limonene, methyl citronellate, bornyl acetate, myrtenal, myrtenol, myrtenyl acetate, α-terpineol, citronellol, citronellyl acetate, nerolidol, farnesol, and an unusual hydroxy ketone. Of the many trace constituents, β-phellandrene, citronellal, "iso-" citronellal, linalool, geraniol, isopulegol, 4-terpinenol, and ε-cadinene were isolated, whereas camphene, sabinene, α-phellandrene, γ-terpinene, terpinolene, p-cymene, fenchone, thujone, isothujone and δ-cadinene could only be tentatively identified.There was little variation in the quantitative composition of the leaf oil from one plant to another. Since the composition of this oil differs significantly from that of other juniper leaf oils, chemotaxonomic studies by means of leaf oil analysis are feasible.



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