160296-83-3Relevant academic research and scientific papers
Enzyme reactions in apolar solvents. The resolution of branched and unbranched 2-alkanols by porcine pancreatic lipase
Morgani, Brian,Oehlschlager, Allan C.,Stokes, Thomas M.
, p. 1611 - 1620 (1991)
Straight-chain and branched 2-alkanols were subjected to enzyme catalyzed transesterification in organic solvent using porcine pancreatic lipase, high enantioselectivity being generally observed. The method was applied to the synthesis of (R)-(-)-9-hydroxy-(E)-decenoic acid, a component of the queen bee mandibular gland pheromone.
CHIRAL ESTERS: SEX PHEROMONE OF THE BAGWORM, Oiketicus kirbyi (LEPIDOPTERA: PSYCHIDAE)
Rhainds, Marc,Gries, Gerhard,Li, Jianxiong,Gries, Regine,Slessor, Keith N.,et al.
, p. 3083 - 3096 (1994)
Gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract of female bagworms, Oiketicus kirbyi (Guilding), revealed five EAD-active compounds. Retention index calculations, GC-mass spectrometry in both full-scan and selected-ion monitoring modes and GC-EAD analyses of authentic standards identified the compounds as 1-methylbutyl octanoate (MBO), 1-methylbutyl nonanoate (MBN), 1-methylbutyl decanoate (MBD), 1-methylpentyl decanoate (MPD), and 1-methylbutyl dodecanoate (MBDD). Of these five chiral esters, MBD was most abundant in extracts and elicited the strongest antennal response. In field experiments in Costa Rica, (R)-MBD attracted O.kirbyi males, whereas (S)-MBD in combination with (R)-MBD inhibited response. R but not S enantiomers of MBO, MBN, and MBDD strongly synergized attraction to (R)-MBD. (S)-MBO and (S)-MBDD were inactive, whereas (S)-MBN was inhibitory. (R)-, (S)- and racemic MPD were inactive. Blends of (R)-MBD in ternary combination with either (R)-MBO and (R)-MBN or (R)-MBN and (R)-MBDD were as attractive as the five-ester blend. Five- and four-ester blends were equally attractive, suggesting redundancy of pheromone components for attraction of males. The multiple sex pheromone component blend of chiral esters in O. kirbyi may have evolved to maintain species-specific communication in bagworm communication in bagworm communities of tropical Americas. - Keywords: Lepidoptera; Psychidae; Oiketicus kirbyi; bagworm; sex pheromone; pheromone chirality; 1-methylbutyl octanoate; 1-methylbutyl nonanoate; 1-methylbutyl decanoate; 1-methylbutyl dodecanoate
