The Discovery of 2-Hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: a Semiochemical in Orchid Pollination

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Bohman, Bjorn
Jeffares, Lynne
Flematti, Gavin
Phillips, Ryan
Dixon, Kingsley
Peakall, Rodney
Barrow, Russell

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American Chemical Society

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.

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Organic Letters

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2037-12-31