Stegobium paniceum

Attractive Compounds. Only little is known about the systems of chemical communication in anobiid beetles. Investigations have been mainly concerned with two economically important species, the cigarette beetle, Lasioderma serricorne, and the drugstore beetle, Stegobium paniceum. 

Kuwahara, Y., Fukami, H., Ishii, S., Matsumura, F. and Burkholder, W. E. (1975b). Studies on the isolation and bioassay of the sex pheromone of the drugstore beetle, Stegobium paniceum (Coleoptera Anobiidae). Journal of Chemical Ecology 1 413 122. 

Chemical studies on the Anobiidae sex pheromone of the drugstore beetle, Stegobium paniceum (L) (Coleoptera). Tetrahedron 34 1769-1774. 

Figure 6.6 Structures of 2,3-dihydro-2,3,5-trimethyl-6-(1 -methyl-2 -oxobutyl)-4H-pyran-4-one (stegobinone), pheromone of Stegobium paniceum (L.) (Anobiidae) (Kuwahara et al., 1978) and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene, pheromone component of Carpophilus hemipterus (L.) (Nitidulidae) (Bartelt et al., 1991). The carbon skeletons are identical, and likely derived through similar pathways (see text).

P18 Stegobium paniceum, drug store beetle,811,812 Anobium punctatum, anobiid beetle 813... 

Strong protic acids will also cleave benzyl ethers. A highly stereoselective synthesis of the sex pheromone of the drugstore beetle Stegobium paniceum by Matteson and co-workers277 conveniently accomplished the debenzylation of the benzyl ether 151.1 with methanesulfonic add in chloroform [Scheme 4.151]. 

Drugstore beetle (Stegobium paniceum) is a serious pest of a wide variety of commodities and stored products. In 1978 Y. Kuwahara et al. proposed the structure of stegobinone, the major and crystalline component of the female-produced sex pheromone of 5. paniceum, as 114 (Figure 4.69). Nothing was... 

Ephestia cautella, Stegobium paniceum, Tribolium castaneum, Oryzaephilus surinamensis Peanut, cumin, wheat flour, copra Srinath et al. (1976)... 

Spices (whole) Stegobium paniceum, Lasioderma serricorne... 

Stegobium paniceum Stegobinone 2,3-dihydro-2,3,5-trimethyl-6-(l - methyl-2 -oxobutyl-4H-pyran-4-one... 

The pheromone components of C. lugubris and C. hemipterus are undoubtedly related bios3mthetically. Although none of these compounds had been known prior to the nitidulid research, the 13-carbon pheromone component 1 of C. hemipterus has the same carbon skeleton as the pheromone of the drugstore beetle, Stegobium paniceum (14). A polyketide origin of this pheromone was proposed, in which the polyketide arose from the condensation of one acetate and four propionate units (L5). Polyketide biosyntheses have also been proposed for a number of related structures (16, 17). The... 

Steam distillation, 3290, 3667, 3978,4090 Stearidonic acid, 1737 Steatosis, 1385 Stegobium paniceum, 4091 Stemmedine, 584 Stemona, 1175 Stemona alkaloids, 1183 Stephaniae tetrandrae, 1179 Stephania tetrandra S. Moore, 1449 Stephanine, 431 Stephanitis pyri, 4094 Stepholidine, 449 Sterculiaceae, 725 Stereocenters, 947 Stereochemistry, 3241, 3242 Stereoisomerism, 1014 Stereoisomers, 912, 2109, 3647 Stereospecific conversion, 1670 Stereospecificity, 4069 Steroidal, 412 alkaloids, 3237 lactones, 3468, 3473, 3488 Steroid hormone receptors, 3508 Steroids, 2733-2735, 2737-2741, 2746-2749, 2751, 2753, 2755-2757, 2763, 3666, 3670... 

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