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Deuterated analogues of 4,8‐dimethyldecanal, the aggregation pheromone of Tribolium castaneum : synthesis and pheromonal activity
Author(s) -
Kim Junheon,
Matsuyama Shigeru,
Suzuki Takahisa
Publication year - 2004
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.881
Subject(s) - pheromone , chemistry , olfactometer , red flour beetle , stereochemistry , attraction , botany , larva , linguistics , philosophy , biology
Abstract To elucidate the deuterium isotope effect (DIE) in pheromonal activity and to investigate the biosynthetic pathway of 4,8‐dimethyldecanal (4,8‐DMD; 1 ), the aggregation pheromone of the red flour beetle ( Tribolium castaneum ), deuterated analogues of 4,8‐DMDs ( 2 , 3 , 4 , and 5 ), were synthesized and their pheromonal activities were tested using a two‐hole pitfall olfactometer. Although no apparent DIE was observed in their pheromonal activities, 4,8‐DMD‐ 1‐d 1 ( 2 ) was less attractive than other analogues, which suggested that the bond distance between the formyl group of 1 and its receptor was critical in pheromone recognition by T. castaneum . Copyright © 2004 John Wiley & Sons, Ltd.