| Title: | "Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus" |
| Author(s): | Leal WS; Shi X; Nakamuta K; Ono M; Meinwald J; |
| Address: | "Department of Chemistry, Cornell University, Ithaca, NY 14853" |
| ISSN/ISBN: | 0027-8424 (Print) 1091-6490 (Electronic) 0027-8424 (Linking) |
| 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 |
| Keywords: | "Animals Chromatography, Gas/methods Coleoptera/*chemistry Electrochemistry Female Flame Ionization Hexanones/*chemistry Hot Temperature Isomerism Ketones/*chemistry Male Molecular Structure Sex Attractants/*chemistry Stereoisomerism;" |
| Notes: | "MedlineLeal, W S Shi, X Nakamuta, K Ono, M Meinwald, J eng AI 12020/AI/NIAID NIH HHS/ Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. 1995/02/14 Proc Natl Acad Sci U S A. 1995 Feb 14; 92(4):1038-42. doi: 10.1073/pnas.92.4.1038" |
