72279-59-5Relevant academic research and scientific papers
Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
, p. 111 - 121 (2007/10/03)
Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
Synthesis of [1-11C]-2-octynoic acid, [1-11C]-2-decynoic acid and [1-11C]-3-(R,S)-methylocatanoic acid as potential markers for PET studies of fatty acid metabolism
Kawashima, Hidefumi,Yajima, Kazuyoshi,Kuge, Yuji,Hashimoto, Naoto,Miyake, Yoshihiro
, p. 181 - 193 (2007/10/03)
[1-11C]-2-Octynoic acid, [1-11C]-2-decynoic acid and [1-11C]-3-(R,S)-methyloctanoic acid have been synthesized in order to evaluate these compounds as PET (Positron Emission Tomography) tracers for imaging in vivo medium-chain acyl-CoA dehydrogenase and medium-chain fatty acid utilization. The synthesis was performed by the Grignard reaction between alkylmagnesium bromides and [11C]CO2. The radiochemical yields of [1-11C]-2-octynoic acid, [1-11C]-2-decynoic acid, and [1-11C]-3-(R,S)-methyloctanoic acid were 10, 7 and 1% based on the [11C]CO2 used respectively. Radiochemical purity was >99% in all cases.
Sex pheromone of the pine sawfly Diprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity
Bergstroem,Wassgren,Anderbrant,Faegerhag,Edlund,Hedenstroem,Hoegberg,Geri,Auger,Varama,Hansson,Loefqvist
, p. 370 - 380 (2007/10/02)
The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol 8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatograghic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (> 99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 μg of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 μg in France and 50 μg in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.
