A Simple and Cost Effective Synthesis of 3,11-Dimethylnonacosan-2-one, A Female Sex Pheromone of the German Cockroach

The cuticular surface of sexually mature females of the German cockroach contains a sex pheromone that, upon contact with the male's antennae, elicits a characteristic species-specific courtship behavior. This female-specific pheromone is a blend of several long-chain methyl ketones, alcohols and aldehydes, all derived from prominent cuticular hydrocarbons found in all life stages of this cockroach. We found that contact with the antennae of 5 out of 20 assayed cockroach species elicited courtship behavior in German cockroach males. The heterospecific courtship-eliciting compounds were isolated by behaviorally guided fractionation of the active crude extracts and compared to the native sex pheromone components. We identified two active compounds from the cuticular extract of the Oriental cockroach, Blatta orientalis -- 11-methylheptacosan-2-one and 27-oxo-11-methylheptacosan-2-one; the former compound was confirmed by synthesis and proved to independently stimulate courtship in German cockroach males. These compounds share common features with, but are distinct from, any of the known contact sex pheromone components. This suggests that sex pheromone reception in the male German cockroach is unusually promiscuous, accepting a wide range of compounds that share certain features with its native pheromone, thus resulting in a broad spectrum of behavioral response to other species. We propose that several characteristics of their mating system -- chiefly, absence of closely related species in the anthropogenic environment, resulting in relaxation of selection on sexual communication, and a highly male-biased operational sex ratio -- have driven males to respond with extremely low thresholds to a wide spectrum of related compounds.

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Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica

Eliyahu

Nojima

Capracotta

et al. 2008

Naturwissenschaften

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Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations

Shingate

Hazra

2017

Tetrahedron

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Synthesis of Pheromones: Highlights from 2005-2007

Bergmann

Villar²,

Flores³

et al. 2009

COC

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A Simple and Cost Effective Synthesis of 3,11-Dimethylnonacosan-2-one, A Female Sex Pheromone of the German Cockroach

Cited by 3 publications

References 11 publications

Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica

Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica

Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations

Synthesis of Pheromones: Highlights from 2005-2007

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