78774-68-2Relevant academic research and scientific papers
PRODUCTION METHOD OF 4,8-DIMETHYLDECANAL
-
Paragraph 0009; 0013; 0020, (2016/12/12)
PROBLEM TO BE SOLVED: To provide a method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal effective as pheromones for rust-red flour beetles and confused flour beetles, practically in a high yield through a small number of steps. SOLUTION: A method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal includes a first step of tosylating (S)-citronellol to obtain a tosylate, a second step of reacting the tosylate with a Grignard reagent to obtain an alkene, a third step of epoxidating the alkene to obtain an epoxide, and a fourth step of cleaving the epoxide with a periodic acid to obtain 4,8-dimethyldecanal. COPYRIGHT: (C)2015,JPOandINPIT
Synthesis and biological activity of methyl 2,6,10-trimethyldodecanoate and methyl 2,6,10-trimethyltridecanoate: Male-produced sexual pheromones of stink bugs Euschistus heros and Piezodorus guildinii
Zarbin, Paulo H. G.,Reckziegel, Aurelia,Plass, Ernst,Borges, Miguel,Francke, Wittko
, p. 2737 - 2746 (2007/10/03)
Methyl 2,6,10-trimethyltridecanoate (1) and methyl 2,6,10-trimethyldodecanoate (2) have been identified as male-produced sex pheromones of the Brazilian soybean stink bugs Euschistus heros (F.) and Piezodorus guildinii (Westwood). In order to establish a defined attractive blend for both species, compounds 1 and 2 were synthesized as mixtures of stereoisomers to be employed in behavior bioassays. (±)-Citronellol (3) was utilized as starting material, and the syntheses was carried out in six steps with good overall yield. When tested alone, synthetic compounds 1 and 2 proved to be active in a two-choice olfactometer; however, a 20: 1 mixture of 1 and 2 was much more attractive to E. heros females. A similar blend had been found among the headspace volatiles of males.
Identification of the Aggregation Pheromone of Flour Beetles Tribolium castaneum and T. confusum (Coleoptera: Tenebrionidae)
Suzuki, Takahisa
, p. 1357 - 1364 (2007/10/02)
The aggregation pheromone produced by the male red flour beetle Tribolium castaneum, and confused flour beetles, T. confusum was identified as 4,8-dimethyldecan-1-al by GLC, GC-MS, PMR spectra, and synthesis of the compound.The synthetic pheromone was less attractive compared with the natural pheromone, because the synthetic sample was composed of four optical isomers.
