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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1995 Feb 14;92(4):1038–1042. doi: 10.1073/pnas.92.4.1038

Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.

W S Leal 1, X Shi 1, K Nakamuta 1, M Ono 1, J Meinwald 1
PMCID: PMC42632  PMID: 7862629

Abstract

Male-released sex pheromone constituents of the longhorn beetle Anaglyptus subfasciatus (Coleoptera: Cerambycidae) are identified by GC-MS and GC-Fourier transform infrared as a 7:1 molar mixture of 3-hydroxy-2-hexanone and 3-hydroxy-2-octanone. These two compounds undergo thermal isomerization during GC analyses to give the corresponding 2-hydroxy-3-alkanones. Comparison of GC retention times of the natural products with those of synthesized enantiomerically pure compounds revealed that both semiochemicals have (R)-stereochemistry. These absolute configurations were confirmed by comparisons of the (R)-methoxy(trifluoromethyl)phenylacetic acid esters of insect-derived and synthetic samples.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Matos V., Roberto H., Leal M., Marques A. M., Camacho M., de Moura Z., Fong F. P., Gonsalves A. Implantaço de pacemaker em doente com persistência da veia cava superior esquerda e atrésia da veia cava superior direita. Rev Port Cardiol. 1994 Nov;13(11):853-6, 809. [PubMed] [Google Scholar]

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