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  • 1
    Electronic Resource
    Electronic Resource
    Important chiral monoterpenoid ethers in flavours and essential oils – enantioselective analysis and biogenesis (1999)
    Springer
    European food research and technology 209 (1999), S. 3-11 
    Details
    ISSN: 1438-2385
    Keywords: Key words Chiral cyclic monoterpenoid ethers ; Flavor ; Fragrance ; Enantioselective analysis ; Biogenesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Notes: Abstract  The enantioselective analysis and the biogenesis of rose oxide, rose oxide ketone, nerol oxide, furanoid linalooloxide, pyranoid linalooloxide, dill ether, linden ether, menthofuran, and 3,6-dimethylcoumaran is reviewed. All these compounds are important chiral cyclic monoterpenoid ethers and can be analyzed enantioselectively using modified cyclodextrins as chiral stationary phases in capillary gas chromatography (cGC). The evaluation of the enantiomeric ratios of these compounds can be used in the authenticity control of flavors and fragrances. Moreover, the enantioselective cGC is also an efficient tool in elucidating the biogenesis of these compounds. Biomimetic studies as well as in vivo feeding experiments using stable isotope labelling have shown that polyhydroxylated or epoxidated monoterpenes are direct precursors of these cyclic ethers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002170050447
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Enantiomer distribution of ethyl lactate — a new criterion for quality assurance of wine (1996)
    Springer
    European food research and technology 203 (1996), S. 499-500 
    Details
    ISSN: 1438-2385
    Keywords: Ethyl lactate ; Enantiomer distribution ; Wine ; Quality assurance ; Enantioselective analysis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Notes: Abstract Enantioselective gas chromatography using heptakis (6-0-tert.-butyldimethylsilyl-2,3-di-0-methyl)-β-cyclodextrin as the chiral stationary phase was used in chirality evaluation of ethyl lactate in wines, which is helpful in the quality assurance of wine. (S)-methyl lactate is recommended as an internal standard.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01193152
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Mechanistic aspects of the biogenesis of rose oxide in Pelargonium graveolens L'Héritier (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 229-237 
    Details
    ISSN: 0899-0042
    Keywords: deuterium labelling ; menthocitronellol ; citronellol ; enantioselective multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS) ; dynamic headspace analysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanistic aspects of the biogenesis of the chiral monoterpenoid rose oxide in Pelargonium graveolens L'Héritier are investigated using deuterium-labelled precursors. After administration of the precursors using the cut-stem method, the dynamic headspace extracts of the plants are analysed using multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS). It is unequivocally shown that this plant is able to convert citronellol and menthocitronellol into cis-/trans-rose oxide. Menthocitronellol is converted into rose oxide with a clearly detectable enantiodiscrimination. These facts may be explained with the presence of an oxidase, which is able to oxidize citronellol and menthocitronellol in allylic position. A photooxygenation mechanism including singlet oxygen as the oxidizing agent is rather unlikely. Chirality 10:229-237, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 4
    Electronic Resource
    Electronic Resource
    Stereoisomeric flavor compounds LXXVII: 3-Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers (1997)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 20 (1997), S. 251-256 
    Details
    ISSN: 0935-6304
    Keywords: Enuntioselective GC ; Structure elucidation ; 3-Butylhexahydrophthalide stercoisomers ; Odor thresholds ; Celery oil ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Using heptakis-(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cy-clodextrin as the chirul stationary phase in enantioselective gas chromatography, the simultaneous enantioselective analysis of all eight 3-butylhexahydrophthalide Stereoisomers was achieved. Fur-thermore, the odor characteristics and odor thresholds were investigated by enantioselective gas chromatography/olfactometry. Racemic standards were synthesized via hydrogenation and subsequent base catalyzed epimerization. Starting from racemic 3-butylphthalide. After separation by high performance liquid chromatography. Relative configurations of the pure diastereoisom-ers were determined by means of NOE-difference spectroscopy. The absolute configuration at C-3 was determined starting from (3S)-butylphthalide as an educt for hydrogenation and epimerization. Absolute configurations of all eight 3-butylhexahydrophtbalide stereoisomers are unambiguously concluded from the NOE-experi-ments in connection with the determination of the absolute configuration at C-3.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240200502
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    Paper (German National Licenses)
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  • 5
    Electronic Resource
    Electronic Resource
    Stereoisomeric Flavor Compounds LXXXI: Dill Ether and Its cis-Stereoisomers: Synthesis and Enantioselective Analysis (1998)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 21 (1998), S. 185-188 
    Details
    ISSN: 0935-6304
    Keywords: Dill ether ; stereoselective synthesis ; dill ether stereoisomers ; enantioselective GC ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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