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Synthesis and Biological Activity of the Four Stereoisomers of 4-methyl-3-heptanol: Main Component of the Aggregation Pheromone of Scolytus Amygdali

Synthesis and Biological Activity of the Four Stereoisomers of 4-methyl-3-heptanol: Main Component of the Aggregation Pheromone of Scolytus Amygdali

A Zada, S Ben-Yehuda, E Dunkelblum, M Harel, F Assael, Z Mendel

J Chem Ecol. 2004 Mar;30(3):631-41.

PMID: 15139313

Abstract:

Stereoisomers of 4-methyl-3-heptanol are major components of aggregation pheromones of bark beetles and trail pheromones of ants. Recently, (3S,4S)-4-methyl-3-heptanol (I) has been tentatively identified as the main component of the aggregation pheromone of the almond bark beetle, Scolytus amygdali (Coleoptera: Scolytidae). The four stereoisomers of 4-methyl-3-heptanol were prepared and bioassayed. Key steps included preparation of chiral 4-methyl-3-heptanones using SAMP and RAMP reagents, reduction to the corresponding alcohols, and stereospecific transesterification with vinyl acetate with lipase AK catalysis. In field tests, only (3S,4S)-4-methyl-3-heptanol attracted beetles in combination with the synergist (3S,4S)-4-methyl-3-hexanol, whereas (3R,4S)- and (3R,4R)-4-methyl-3-heptanols were inhibitory.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP589822	3-Heptanol		589-82-2	Price

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