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Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae) (1990)

Schulz, Stefan ; Francke, Wittko ; König, Wilfried A. ; [et al.]

Springer

Journal of chemical ecology 16 (1990), S. 3511-3521

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ISSN: 1573-1561

Keywords: Hepialus ; Lepidoptera ; Hepialidae ; swift moth ; pheromone ; dihydropyrone ; 2,9-dioxabicyclo[3.3.1] nonane ; behavior ; electrophysiology

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract (R)-6-Ethyl-2-methyl-2,3-dihydro-4H-pyran-4-one, (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3. 1]non-7-ene, and (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one represent the main components in the male pheromone of the swift moth,Hepialus hecta. The amounts of the three components were 40, 5, and 5 μg per male, respectively. Structure elucidation of the compounds was based on spectroscopic data as compared to synthetic reference samples. The absolute configurations were determined by gas chromatography on chiral stationary phases; optically active samples served as reference compounds. Electrophysiological and behavioral experiments with natural material and synthetic samples clearly showed the three heterocyclic compounds to act as pheromones. (E, E)-α-Farnesene represents the main component of the scent secretion of maleHepialus humuli.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00982114

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Determination of the absolute configuration of secondary alcohols with Horeau's method including enantioselective gas chromatography (1994)

König, Wilfried A. ; Gehrcke, Bärbel ; Weseloh, Gerald

New York, NY [u.a.] : Wiley-Blackwell

Chirality 6 (1994), S. 141-147

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ISSN: 0899-0042

Keywords: Horeau's method ; configuration of secondary alcohols ; enantioselective gas chromatography ; 2-phenylbutyric acid ; cyclodextrin derivative ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The reaction of optically active secondary alcohols with excess of racemic 2-phenylbutyric acid anhydride in pyridine proceeds at different rates to the diastereoisomeric esters (kinetic partial resolution). According to Horeau the (unknown) absolute configuration of the alcohol can be derived from the optical rotation of the remaining excess of 2-phenylbutyric acid in the reaction mixture. Measuring the optical rotation may be very difficult in cases of small absolute rotation values and may be inaccurate due to the necessity to completely remove all chiral impurities. The application of Horeau's method is greatly facilitated by gas chromatographic determination of the enantiomeric ratio of the remaining 2-phenylbutyric acid after methylation using a short capillary column with heptakis(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin as a chiral stationary phase. Baseline resolution of the enantiomers is achieved after approximately 10 min of retention time. Due to the high selectivity of capillary gas chromatography the probability of impurities in the mixture to interfere with the measurement of the enantiomeric ratio is extremely low. © 1994 Wiley-Liss, Inc.

Additional Material: 3 Ill.