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  • Enantioselective gas chromatography  (9)
  • Cyclodextrin derivatives  (5)
  • Cyclodextrins  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Stereochemical analysis of constituents of essential oils and flavor compounds by enantioselective capillary gas chromatography (1990)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 13 (1990), S. 328-332 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; Cyclodextrin derivatives ; Terpenoid hydrocarbons ; Chiral carbonyl compounds ; Flavor alcohols ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Modified cyclodextrins interact enantioselectively with a great variety of volatile chiral constituents of essential oils by forming diastereomeric inclusion complexes. Capillary gas chromatography is used for resolving the enantiomers of terpenoid hydrocarbons (camphene, α-pinene, limonene, α-phellandrene), carbonyl compounds (carvone, fenchone, menthone, isomenthone, piperitone, camphor, myrtenal), and alcohols (trifluoroacetylated β-citronellol, myrtenol, trans-pinocarveol, 1-octen-3-ol, and underivatized linalool). The enantiomeric composition of some of these compounds in a variety of essential oils is investigated.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240130507
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  • 2
    Electronic Resource
    Electronic Resource
    Gas chromatographic enantiomer separation of agrochemicals and polychlorinated biphenyls (PCBs) using modified cyclodextrins (1994)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 17 (1994), S. 859-864 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; Cyclodextrin derivatives ; Polychlorinated pesticides ; Polychlorinated biphenyls (PCBs) ; Pyrethroid insecticides/Allethrin ; Organophosphorus pesticides/Acephate, Malaoxon ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomers of the polychlorinated polycyclic xenobiotics heptachlor, cis- and trans-chlordane, cis- and trans-heptachlorepoxide, oxychlordane, and bromocyclen have been resolved by gas chromatography with selectively substituted cyclodextrins. The order of elution of these compounds and of α-hexachlorocyclohexane (α-HCH) was determined by comparison with enantiomerically enriched reference compounds obtained by preparative enantioselective gas chromatography.A separation of the eight stereoisomers of the pyrethroid insecticide allethrin into seven peaks was achieved. Both trans-diastereomers were separated into their enantiomers and the order of elution could be determined by comparison with commercially available (S)-bioallethrin and trans-bioallethrin. Also one cis-diastereomer was separated, wheras the other cis-isomer could not be resolved. In addition 15 out of 19 stable atropisomeric polychlorinated biphenyls with 5, 6 and 7 chlorine substituents, some chiral organophosphorus pesticides, including acephate and malaoxon and the herbicide bromoacil were separated.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240171209
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  • 3
    Electronic Resource
    Electronic Resource
    Unusual retention behavior of methyl lactate and methyl 2-hydroxybutyrate enantiomers on a modified cyclodextrin (1991)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 14 (1991), S. 694-695 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; Reversal of elution order ; Isoenantioselective temperature ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240141013
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  • 4
    Electronic Resource
    Electronic Resource
    Gas chromatographic enantiomer separation with modified cyclodextrins: Carboxylic acid esters and epoxides (1993)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 16 (1993), S. 175-181 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; 2,6-di-O-methyl-3-O-pentyl-β- and y-cyclodextrins ; α and β hydroxy acids ; Branched carboxylic acids ; Non-steroidal anti-inflammatory drugs ; Abscisic Acid ; Epoxides ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The wide range of application of 2,6-di-O-methyl-3-O-pentyl-β-and y-cyclodextrins is demonstrated by the resolution of the enantiomers of the methyl esters of chiral carboxylic acids: α and β hydroxy acids with up to 18 carbon atoms, hydroxy di- and tricarboxylic acids, and alkyl/aryl-substituted carboxylic acid methyl esters, including the plant hormone abscisic acid, insect juvenile hormones, and some non-steroidal anti-inflammatory drugs can be resolved with generally large separation factors. The new cyclodextrin derivatives also exhibit high selectivity for epoxides.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240160309
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  • 5
    Electronic Resource
    Electronic Resource
    Enantiomer separation by capillary SFC and GC on immobilized octakis(2,6-di-O-methyl-3-O-pentyl)-γ-cyclodextrin (1994)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 17 (1994), S. 779-783 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; Enantioselective supercritical fluid chromatography ; Immobilized chiral stationary phases ; Modified cyclodextrin ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Heptakis(2,6-di-O-methyl-3-O-pentyl) (2-O-methyl-6-O-oct-1-enyl-3-O-pentyl)-γ-cyclodextrin was immobilized to narrow-bore fused silica capillaries after selective modification. One tert-butyldimethylsilyl group was introduced into octakis-(2-O-methyl-3-O-pentyl)-γ-cyclodextrin in order to get a pure monofunctionalized cyclodextrin derivative. During synthesis the tert-butyldimethylsilyl group was replaced by an anchoring group to bind the cyclodextrin to a polysiloxane. After thermal immobilization of the modified polysiloxane this new chiral stationary phase was applied in GC and SFC. High efficiency separations were obtained in GC. In SFC very polar compounds could be chromatographed at low temperatures resulting in higher separation factors as compared to GC.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240171110
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  • 6
    Electronic Resource
    Electronic Resource
    Enantiomeric composition of the chiral constituents of essential oils - part 3: Diterpene hydrocarbons (1997)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 20 (1997), S. 257-260 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective GC ; Diterpene Hydrocarbons ; Cyclodextrin derivatives ; Essential oils ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomeric diterpene hydrocarbons were isolated from different plants and identified by mass spectrometric and NMR investigations. All enantiomeric pairs could be resolved by capillary gas chromatography using either heptakis(2,6-di-O-methyl-3-O-pen-tyl)-β-cyclodextrin or heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin as chiral stationary phases.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240200503
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  • 7
    Electronic Resource
    Electronic Resource
    Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part VII: Cyclodextrins with an inverse substitution pattern - synthesis and enantioselectivityPart VI, see reference [6]. (1990)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 13 (1990), S. 702-707 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective capillary gas chromatography ; Cyclodextrins ; Inverse substitution pattern ; Mechanism of chiral recognition ; Applications ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Transferring the site of specific substitution of dipentylated cyclodextrins with methyl or acyl residues from the secondary 3-hydroxyl group to the primary 6-hydroxyl group was expected to provide new information on the mechanism of chiral recognition. The 3-position points towards and the 6-position points away from the cyclodextrin cavity which via inclusion complex formation is supposed to play a major role in chiral separation. The “inverse” 6-O-acyl-2,3-di-O-pentyl-cyclodextrins displayed almost no enantioselectivity but the corresponding 6-O-methyl derivatives are a versatile supplement to the chiral capillary GC phases nowadays available. Among the compounds that could be enantiomerically resolved are alcohols, amino acids, alkyl halides, bicyclic ethers, acetals, olefins, other hydrocarbons and chiral pharmaceuticals.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240131010
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  • 8
    Electronic Resource
    Electronic Resource
    Enantiomeric composition of the chiral constituents in essential oils. Part 1: Monoterpene hydrocarbons (1992)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 15 (1992), S. 184-189 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; Cyclodextrin derivatives ; Monoterpene hydrocarbons ; Essential oils ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Using a dual column gas chromatograph equipped with two capillary columns coated with heptakis(6-O-methyl-2,3-di-O-pentyl)-β-cyclodextrin (6-me-2,3-pe-β-CD) and octakis(6-O-methyl-2,3-di-O-pentyl)-γ-cyclodextrin (6-me-2,3-pe-γ-CD), respectively, all important olefinic monoterpene hydrocarbons occurring in essential oils, including α-thujene, α- and β-pinene, camphene, sabinene, α- and β-phellandrene, Δ-3-carene and limonene can be resolved into enantiomers. With the chromatographic system described the characteristic enantiomeric composition of these monoterpene hydrocarbons in essential oils can be determined.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240150310
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  • 9
    Electronic Resource
    Electronic Resource
    New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils (1992)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 15 (1992), S. 367-372 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective gas chromatography ; Two-dimensional GC ; Essential oils ; Lavandulol ; α-Bisabolol ; Nerolidol ; Methyl jasmonate ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New β- and γ-cyclodextrin derivatives, selectively substituted with n-pentyl and methyl groups, e.g. heptakis(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin, octakis(2-O-methyl-3,6-di-O-pentyl)-γ-cyclodextrin, and octakis(2,6-di-O-methyl-3-O-pentyl)-γ-cyclodextrin, have been prepared from specifically protected intermediates. The new cyclodextrin derivatives exhibit unique enantioselectivity towards important chiral constituents of essential oils. The enantiomers of lavandulol, α-bisabolol, nerolidol, and other terpenoid alcohols could be resolved and their presence in different essential oils could be proved. Methyl jasmonate and epi-methyl jasmonate could, in addition, be detected in jasmine concrete by two-dimensional gas chromatography. The enantiomers of the macrocyclic ketone muscone have been separated for the first time.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240150603
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  • 10
    Electronic Resource
    Electronic Resource
    Enantiomeric composition of the chiral constituents of essential oils. Part 2: Sesquiterpene hydrocarbons (1994)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 17 (1994), S. 315-320 
    Details
    ISSN: 0935-6304
    Keywords: Enantioselective GC ; Sesquiterpene hydrocarbons ; Cyclodextrin derivatives ; Essential oils ; Liverworts ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A number of sesquiterpene hydrocarbons commonly occurring in essential oils has been prepared as racemic mixtures by chemical synthesis. Preparative gas chromatography with selectively per-O-alkylated cyclodextrins has been employed for the isolation of enantiomeric mixtures or pure enantiomers from the essential oils of higher plants and liverworts (Hepaticae). The enantiomers of α-curcumene, α- and β-bisabolene, β-elemene, δ-elemene, α-copaene, δ-cadinene, cis- and trans-calamenene, and bicyclogermacrene could be resolved by enantioselective gas chromatography on capillary columns coated with cyclodextrin derivatives. The enantiomeric composition of these sesquiterpene hydrocarbons in various essential oils was determined.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240170507
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