3511-93-1Relevant academic research and scientific papers
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.
Microbial Oxidation of Isoprenoid Alkanes, Phytane, Norpristane and Farnesane
Nakajima, Kenji,Sato, Akio,Takahara, Yoshimasa,Iida, Takeo
, p. 1993 - 2002 (2007/10/02)
Rhodococcus sp.BPM 1613, a pristane oxidizing microorganism, grows on isoprenoid hydrocarbons such as phytane (2,6,10,14-tetramethylhexadecane), norpristane (2,6,10-trimethyl-pentadecane) and farnesane (2,6,10-trimethyldodecane) as the sole carbon source, resulting in accumulation of oxidation products in the culture broth.The oxidation products of phytane, norpristane and farnesane in the respective culture broth were isolated and purified by the use of silica gel column chromatography.Their chemical structures were determined by instrumental analyses such as IR, NMR and mass spectrometry.The oxidation products of phytane were identified as 2,6,10,14-tetramethyl-1-hexadecanol and 2,6,10,14-tetramethylhexadecanoic acid, the product of norpristane as 2,6,10-trimethyl-1-pentadecanol, and that of farnesane as 2,6,10-trimethyl-1-dodecanol.All these oxidation products were either monoalcohols or monocarboxylic acids derived through oxidation of the isopropyl terminus of each alkane.In addition, the relationship between the terminal structure of isoprenoid hydrocarbons and microbial oxidation was explored on the basis of these results.
