Studies on terpenes

Klouwen, M. H.; Heide, R. ter

doi:10.1016/s0021-9673(01)86421-9

Cited by 64 publications

(13 citation statements)

References 18 publications

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“…It is observed that the bicyclic monoterpene sabinene, having a double bond outside the ring, shows a higher retention than the bicyclic monoterpene α-pinene. These facts are in good agreement with those of other authors [9,12].Among terpenoids, the elution of the acyclic ones (citral, linalool, and linalyl acetate) follows the order of their molecular weight. The monocyclic terpenoid menthol is more strongly retained than the bicyclic 1,8-cineole and borneol, and the elution follows the order of their boiling point.…”

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confidence: 93%

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Gas chromatographic behavior of the diagnostic components of some essential oils

Boneva

2007

Chem Nat Compd

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The natural essential oils are highly complex matrices. Their isolated constituents are extensively utilized for their flavor fragrance, anti-microbial, pharmacological, and medicinal properties.According to the bibliography, gas chromatography (GC) or gas chromatography-mass spectrometry (GC-MS) is the most common method for the qualitative and quantitative analysis of the volatile organic compounds in different essential oils from various parts of the world, e.g., [1][2][3][4][5][6][7].Our literature survey revealed that comparatively minimal study of the chromatographic behavior of essential oils components has been published [8,9]. Jalavi-Heravi et al. [8] investigated the retention behavior of 53 noncyclic and monocyclic terpenes on the polar stationary phase Carbowax 20M. A detailed discussion of the retention behavior of six pine terpenes on six different liquid phases with a wide range of polarity was reported by Diaz et al. [9].Thus, on the basis of the literature survey and taking into account that most of the essential oils are primarily composed of terpenes and their oxygenated derivatives, we decided to study the GC behavior of the diagnostic components of some Bulgarian essential oils: linalool and linalyl acetate (lavender), α-pinene and sabinene (juniper), thymol and carvacrol (thyme), limonene and citral (lemon), borneol and 1,8-cineole (rosemary), menthol (spearmint), and germacrone (geranium).This paper is limited to the determination of the retention indices of some monoterpenes, terpenoids, and nonterpenoid compounds on three liquid phases of increasing polarity and different molecular compact packing in order to interpret their chromatographic behavior. The stationary phases were selected to include different functional groups and potential interactions.The gas chromatographic analyses were carried out on a Perkin-Elmer Model Sigma 2000 gas chromatograph (Norwalk, CT, USA), equipped with a flame-ionization detector and the Chromatographics 2 Data System. The chromatograph was fitted with Permaphase DMS, Permaphase CPMS-1701, and Carbowax 20M fused-silica capillary columns.For the investigated compounds more than five injections were made at two temperatures, and the mean retention times were used for further calculations. The gas holdup time was determined according to the method of Peterson and Hirsch [10]. Retention indices were calculated from the adjusted retention times according to the generally known expression used today [11]. Homologous series of n C 7 -n C 20 alkanes were used. Table 1 lists the retention indices of the compounds studied on the three capillary columns (McReynolds polarity: DMS = 229; CPMS-1701 = 789; Carbowax-20M = 2262), measured at two temperatures. The table also gives the retention index increments (dI/dT) per 10°C.On the nonpolar DMS column, the elution of the monoterpene hydrocarbons follows the order of their boiling points. The monocyclic monoterpene (limonene) is more strongly retained than the bicyclic terpenes (α-pinene and sabinene). This may be attribu...

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confidence: 94%

supporting

confidence: 93%

Gas chromatographic behavior of the diagnostic components of some essential oils

Boneva

2007

Chem Nat Compd

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“…analysis myrcene overlaps with camphene, sabinene, or /3-pinene on non-polar columns, and with 3-carene or a-phellandrene on polar colun~ns (3,5,7,8 The oxygenated aliphatic monoterpenes citronellol, geraniol, nerol, linalool, citr-onellal, citronellic acid, and linalyl acetate all reacted a t a satisfactory rate with the aqueous reagent (see Table 11). The rate of reaction of the dienoid compounds was very rapid and precautions against too rapid reduction of permanganate (procedure B-2) was advisable.…”

Section: Results a N D Discussionmentioning

confidence: 99%

Permanganate–periodate Oxidation: Part Vii. The Oxidation of Some Acyclic Monoterpenes

Rudloff¹

1965

Can. J. Chem.

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The reaction of permanganate-periodate with 1-decene and 1-octadecene in aqueous suspension or media containing tert-butanol has been studied. CIO-compounds are oxidized almost quailtitatively with the aqueous reagent. Myrcene, cis-ocimene, citronellol, citronellal, citronellic acid, geraniol, nerol, linalool, and linalyl acetate are all oxidized in high yield to the predicted products. These can serve conveiliently for chemical identification of the aliphatic terpenes when isolated from mixtures by gas-liquid chromatography. The reaction may also be useful in locating the ',LC-label in tracer studies.

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“…Italian sweet orange oil was listed by Guenther (4) as containing 8% aterpinene. Teranishi detected -terpinene in aromagrams of orange juice (75), and Bernhard (7) reported -terpenine in orange oil. Schweisheimer (72) reported that the volatiles of orange skins w'ere 90% (/-limonene.…”

Section: Resultsmentioning

confidence: 99%