Gas–liquid chromatography of terpenes. Part XVIII. The volatile oil of the leaves of Juniperus communis L.

1969 ◽  
Vol 47 (11) ◽  
pp. 2081-2086 ◽  
Author(s):  
E. von Rudloff ◽  
V. K. Sood
Keyword(s):  
Volatile Oil ◽  
Bornyl Acetate ◽  
Quantitative Composition ◽  
Hydroxy Ketone ◽  
Gas Liquid Chromatography ◽  
Citronellyl Acetate ◽  
Leaf Oil ◽  
The Many ◽  
Trace Constituents ◽  
Common Juniper

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.

Gas-liquid chromatography of terpenes. Part XVI. The volatile oil of the leaves of Juniperus ashei Buchholz

1968 ◽  
Vol 46 (5) ◽  
pp. 679-683 ◽  
Author(s):  
E. Von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Volatile Oil ◽  
Bornyl Acetate ◽  
Gas Liquid Chromatography ◽  
Juniperus Ashei ◽  
Methylene Groups ◽  
Leaf Oil ◽  
Ashe Juniper ◽  
First Time ◽  
Unique Chemical

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.

GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART IV. THE ANALYSIS OF THE VOLATILE OIL OF THE LEAVES OF EASTERN WHITE CEDAR

1961 ◽  
Vol 39 (6) ◽  
pp. 1200-1206 ◽  
Author(s):  
E. von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Volatile Oil ◽  
Complete Analysis ◽  
Bornyl Acetate ◽  
Gas Liquid Chromatography ◽  
Commercial Sample ◽  
Percentage Composition ◽  
White Cedar ◽  
Positive Identification ◽  
Eastern White Cedar

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.

GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART X. THE VOLATILE OILS OF THE LEAVES OF SITKA AND ENGELMANN SPRUCE

1964 ◽  
Vol 42 (5) ◽  
pp. 1057-1062 ◽  
Author(s):  
E. VON RUDLOFF
Keyword(s):  
Liquid Chromatography ◽  
Sitka Spruce ◽  
Bornyl Acetate ◽  
Gas Liquid Chromatography ◽  
Volatile Oils ◽  
Percentage Composition ◽  
Average Percentage ◽  
Engelmann Spruce ◽  
Leaf Oil ◽  
Aliphatic Esters

The leaf oils from Sitka and Engelmann spruce were obtained in 0.36 and 0.094% yield respectively. The average percentage composition was determined by gas–liquid chromatography. Sitka spruce leaf oil was found to contain mainly d-myrcene (23.5%), l-piperitone (23.2%), and d-camphor (17.2%). Smaller amounts of 1,8-cineole, l-β-phellandrene, p-cymene, two aliphatic esters, d-bornyl acetate, d-borneol, and d-terpinen-4-ol were also isolated and several other esters appeared to be present in small amounts. Engelmann spruce leaf oil was found to contain mainly cis-hex-3-en-1-ol (18.5%), d-camphor (16.0%), d-bornyl acetate (8.6%), d-linalool (5.8%), and two unidentified compounds. Smaller amounts of myrcene, β-phellandrene, p-cymene, piperitone, and several sesquiterpenoids were also recorded. Tricyclene, α-pinene, camphene, β-pinene, 3-carene, limonene, γ-terpinene, and terpinolene were found in small amounts in both oils.Phylogenetic relationships between the different spruces and other conifers are discussed.

Chemosystematic studies in the genus Pinus: the leaf oil of Pinus contorta var. latifolia

1971 ◽  
Vol 49 (7) ◽  
pp. 1201-1210 ◽  
Author(s):  
G. Pauly ◽  
E. von Rudloff
Keyword(s):  
Rocky Mountains ◽  
Chromatographic Analysis ◽  
Pinus Contorta ◽  
Volatile Oil ◽  
Jack Pine ◽  
High Yield ◽  
Bornyl Acetate ◽  
Mean Values ◽  
Leaf Oil ◽  
Cis And Trans

Gas chromatographic analysis of the volatile oil of the leaf oil of lodgepole pine from the Rocky Mountains showed 1-β-phellandrene (34%) and 1-β-pinene (30.5%) as major components. Lesser amounts of α-pinene (6.5%), myrcene (3%), cis-ocimene (2.5%), 3-carene (1.5%), terpinolene (1%), γ-terpinene (0.3%), α-terpineol (4%), terpinen-4-ol (0.5%), estragole (0.5%), bornyl acetate (0.5%), linalool (0.3%), a mixture of cadinene isomers (5%), cadinol and muurolol isomers (1.5%), nerolidol (0.6%), and tentatively identified camphene, α-phellandrene, limonene, isopulegol, camphene hydrate, citronellol, bisabolol, and cis- and trans-farnesol were recorded. In addition, hex-2-en-1-al (1.5%) and cis-hex-3-en-1-ol (1%) were isolated, but these may be artefacts because the leaves had to be cut to obtain a high yield of oil. The variation in the relative amounts of terpenes in leaves at different heights on a tree was small. Quantitative analysis of 10 samples per population showed a relatively high tree-to-tree variation, but similar mean values for populations in the Bragg Creek – Kananaskis – Eisenhower Junction area of Alberta. Small, but possibly significant differences were recorded for the samples from the Cypress Hills. Populations north of Lake Louise Station to Jasper, Hinton, and Edson were found to contain a few individuals with terpenes characteristic of jack pine. This indicates that the effects of introgression of lodgepole and jack pine can be detected further southwest than previously reported.

Chemosystematic studies in the genus Pinus. IV. Leaf oil composition and geographic variation in jack pine of eastern North America

1982 ◽  
Vol 60 (12) ◽  
pp. 2762-2769 ◽  
Author(s):  
Martin S. Lapp ◽  
E. von Rudloff
Keyword(s):  
North America ◽  
Jack Pine ◽  
Bornyl Acetate ◽  
Eastern North America ◽  
Gas Liquid Chromatography ◽  
Oil Composition ◽  
Leaf Oil ◽  
Euclidean Distances ◽  
The Mean ◽  
Individual Trees

Leaf terpenes of 420 jack pines from 43 sites (Petawawa provenances) in eastern North America were analyzed by gas–liquid chromatography (GLC). In most trees the major components were α-pinene, β-pinene, myrcene, car-3-ene, limonene, β-phellandrene, and bornyl acetate. Eighteen other monoterpenes were identified and 13 sesquiterpenes were characterized by their spectral properties and GLC retention times. These data were analyzed by centroid cluster analysis of the mean-squared Euclidean distances, which showed that jack pine is a diverse species of two major terpene types with eight minor types and a few outlying individual trees. With the exception that the minor clusters and outliers tend to occur at the fringes of the jack pine range, there is no obvious geographic pattern to these clusters.

Chemosystematic studies in the genus Abies. III. Leaf and twig oil analysis of amabilis fir

1977 ◽  
Vol 55 (24) ◽  
pp. 3087-3092 ◽  
Author(s):  
E. von Rudloff ◽  
R. S. Hunt
Keyword(s):  
Gas Chromatography ◽  
Volatile Oil ◽  
Quantitative Variation ◽  
Bornyl Acetate ◽  
Oil Analysis ◽  
Acetate Methyl ◽  
Leaf Oil ◽  
Cis And Trans

The volatile oil of the leaves, and also the twigs, of amabilis fir consists mainly of (−)-β-phellandrene, (+)-car-3-ene, (−)-β-pinene, (−)-α-pinene, myrcene, (−)-limonene, terpinolene, β-sesquiphellandrene, and β-bisabolene. Smaller relative amounts of santene, tricyclene, camphene, sabinene, α-phellandrene, cis- and trans-ocimene, γ-terpinene, linalool, terpinen-4-ol, α-terpineol, bornyl acetate, methyl thymol, thymol, α-cubebene, α-copaene, caryophyllene, humulene, and cadinene–muurolene isomers and their corresponding alcohols were also identified. The presence of three minor diterpene hydrocarbons and manool was indicated by gas chromatography – mass spectrometry.The quantitative variation within trees, between trees, and among northern, central, and southern populations was determined. The high tree-to-tree variability obscures any significant (P = 0.05) geographic trend that may exist. Several qualitative and many significant quantitative differences exist between the leaf oil compositions of amabilis, grand, alpine, and balsam firs andpossibly also noble, white, and California red firs, and these can serve well in chemosystematic studies.

sGAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART XI. THE VOLATILE OIL OF THE LEAVES OF JUNIPERUS SCOPULORUM SARG

1964 ◽  
Vol 42 (8) ◽  
pp. 1890-1895 ◽  
Author(s):  
E. von Rudloff ◽  
F. M. Couchman
Keyword(s):  
Liquid Chromatography ◽  
Ornamental Plants ◽  
Rocky Mountain ◽  
Volatile Oil ◽  
Major Constituent ◽  
Gas Liquid Chromatography ◽  
Leaf Oil ◽  
Juniperus Scopulorum

The neutral leaf oil of Rocky Mountain juniper was analyzed by gas–liquid chromatography. d-Sabinene was found to be the major constituent (45.7%) and smaller amounts of d-limonene (11.4%), d-α-pinene (4.2%), γ-terpinene (1.15%), p-cymene (1.4%), l-linalool (1.2%), d-terpinen-4-ol (2.9%), citronellol (0.2%),l-β-elemene (0.2–0.3%), three isomeric cadinenes (2.7%), l-elemol (6.0%), and safrole (1.85%) were isolated. α-Thujene, camphene, car-3-ene, myrcene, α-terpinene, terpinolene, thujone, isothujone, methyl citronellate, sabinyl acetate, sabinol, geraniol, α- and δ-cadinol, and trans-isoeugenol were tentatively identified. An unidentified acetate (II) (4.7%) was isolated from the oxygenated sesquiterpene fraction and another appears to be present in trace amounts.The composition of the oils from the leaves of four local ornamental plants was found to differ significantly from that of the wild juniper.

Gas–liquid chromatography of terpenes. Part XVII. The volatile oil of the leaves of Juniperus virginiana L.

1968 ◽  
Vol 46 (23) ◽  
pp. 3743-3750 ◽  
Author(s):  
A.R. Vinutha ◽  
E. Von Rudloff
Keyword(s):  
Absolute Error ◽  
Volatile Oil ◽  
Methyl Eugenol ◽  
Juniperus Virginiana ◽  
Gas Liquid Chromatography ◽  
Internal Standards ◽  
Methyl Vinyl ◽  
Leaf Oil ◽  
The Individual ◽  
Aromatic Ether

The leaf oil of the red juniper was found to contain mainly sabinene, as well as limonene, α-pinene, γ-terpinene, terpinolene, 3-carene, myrcene, 4-terpinenol, citronellol, elemol, γ-, α-, and β-eudesmol, the aromatic ethers estragole, safrole, methyl eugenol, and elemicin. Another aromatic ether, methyl vinyl anisole, was isolated which has not been found previously in essential oils. The acetates 1 and 2 obtained previously in two related juniper leaf oils were present and the first has been identified as elemol acetate. Small amounts of α-thujene, p-cymene, linalool, and δ-cadinene were also identified.Quantitative aspects were studied with a view of future chemosystematic investigations. The error in duplicate runs was 0.1% for well-resolved peaks, but the absolute error, as determined by use of internal standards, was larger. Leaf oils of different trees from Texas and Ontario were found to give wide quantitative variations of the individual components.

GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART XIII. THE VOLATILE OIL OF THE LEAVES OF JUNIPERUS HORIZONTALS MOENCH

1965 ◽  
Vol 43 (5) ◽  
pp. 1017-1021 ◽  
Author(s):  
F. M. Couchman ◽  
E. Von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Rocky Mountain ◽  
Volatile Oil ◽  
Major Constituent ◽  
Gas Liquid Chromatography ◽  
Leaf Oil

The neutral leaf oil of the creeping juniper from the Prairies was analyzed by gas–liquid chromatography. d-Sabinene (36.5%) was found to be the major constituent, and smaller amounts of d-limonene (17.5%), p-cymene (3.0%), d-α-pinene (1.6%), γ-terpinene (0.4%), d-terpinen-4-ol (4.6%), linalool (0.8%), citronellol (0.8%), γ-cadinene (1.3%), l-elemol (3.8%), α-cadinol or γ-eudesmol (1.6%), and impure α-cyperone (3.9%) were isolated. α-Thujene (3.0%), camphene (0.2%), β-pinene (0.3%), myrcene (3.0%),β-phellandrene (0.2%,), terpinolene (0.1%), 2,4-(8)-p-menthadiene (0.1%), methyl citronellate (0.4%), and geraniol (0.2%) were tentatively identified. The composition of this oil closely resembles that of Rocky Mountain juniper leaves. A small amount of the oil from a hybrid of these two species was analyzed and the possibility of detecting hybridization by analysis of the leaf oil is discussed.

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
Keyword(s):  
Liquid Chromatography ◽  
Maximum Yield ◽  
Volatile Oil ◽  
Quantitative Composition ◽  
Gas Liquid Chromatography ◽  
Oil Composition ◽  
Mentha Arvensis ◽  
Autoxidation Product ◽  
The North ◽  
Cis And Trans

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.

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