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  • 1
    Electronic Resource
    Electronic Resource
    Determination of chirality of alcohol or latent alcohol semiochemicals in individual insects (1985)
    Springer
    Journal of chemical ecology 11 (1985), S. 1659-1667 
    Details
    ISSN: 1573-1561
    Keywords: Chiral semiochemicals ; pheromones ; enantiomeric composition ; Ips pini ; Coleoptera ; Scolytidae ; Apis mellifera ; Hymenoptera ; apidae ; Cryptolestes Ferrugineus ; Cucujidae ; acetyl lactate diastereoisomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A method is described for determining the enantiomeric composition of chiral alcohols, lactones, and hydroxy acids in quantities ranging from 25 ng to 10 μg. Derivatization of the substance with chirally pure acetyl lactate, followed by splitless capillary gas chromatography, enables enantiomeric determinations to be made within 1–3% of the actual value. This technique was applied in the determination of semiochemical inIps pini (Say),Apis mellifera (L.), andCryptolestes ferrugineus (Stephens). The results indicate that considerable variability exists within populations of some insects in the composition of their chiral semiochemicals, whereas others produce substances of constant composition.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012119
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  • 2
    Electronic Resource
    Electronic Resource
    Chirality of macrolide pheromones of grain beetles in the generaOryzaephilusandCryptolestes and its implications for species specificity (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1543-1554 
    Details
    ISSN: 1573-1561
    Keywords: Chiral semiochemicals ; pheromones ; enantiomeric composition ; enantiomeric synergism ; Cryptolestes ferrugineux ; Cryptolestes pusillus ; Cryptolestes turcicus ; Oryzaephilus mercator ; Oryzaephilus surinamensis ; Coleoptera ; Cucujidae ; (Z)-3-dodecen-11-olide ; (Z,Z)-3,6-dodecadien 11-olide ; (Z)-5-tetradecen-13-olide ; (Z,Z)-5,8-tetradecadien-13-olide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The chiralities of macrolide lactone aggregation pheromones of five species of economically important grain beetles have been determined by capillary gas chromatographic separation of the diastereomeric (S)-O-acetyllactate derivatives of the hydroxy methyl esters derived from boron trifluoride-catalyzed cleavage of the macrolides in methanol. Chirally pure (Z)-3-dodecen-11-olide (I) is produced in theS configuration byCryptolestes ferrugineus (Stephens) and in theR configuration byOryzaephilus mercator (Fauvel). (Z,Z)-3,6-Dodecadien-11-olide (II) is produced in theR configuration by bothO. mercator andO. surinamensis (L.). (Z,Z)-5,8-Tetradecadien-13-olide (IV) is produced in theR configuration byO. surinamensis and as a 85∶15 mixture ofR andS isomers byC. turcicus. (Z)-5-Tetradecen-13-olide (V) is produced in the S configuration byC. pusillus (Schönherr) and as a 33∶67 mixture of theR andS isomers byC. turcicus (Grouvelle). The results indicate that in these cucujids, species specificity in pheromone response is maintained at least in part by pheromone chirality.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01012296
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