The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: A semiochemical in orchid pollination

Bohman, B. and Jeffares, L. and Flematti, G. and Phillips, R. and Dixon, K. and Peakall, R. and Barrow, R. 2012. The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: A semiochemical in orchid pollination. Organic Letters. 14 (10): pp. 2576-2578.

Source Title

Organic Letters

DOI

10.1021/ol300864u

ISSN

1523-7060

School

Department of Environment and Agriculture

URI

http://hdl.handle.net/20.500.11937/19642

Collection

Curtin Research Publications

Abstract

Drakaea livida (Orchidaceae) is pollinated by sexual deception of the wasp Zaspilothynnus nigripes (Thynnidae). It is shown that the orchid emits the same compound, 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine, that females emit when calling for mates. This novel pyrazine was isolated and identified by GC-EAD and GC-MS and confirmed by synthesis. This compound may represent the first known case of pyrazines as sex pheromones in Hymenoptera.