63357-95-9

Usage

Biochem/physiol Actions

Metabolite produced by plants, as a component of aroma flavours and fragrances and aromas of fruits and vegetablest. Component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum and Trogoderma granarium. gamma-Caprolactone is occasionally found as a volatile component of human urine and has been found in the polar fraction of human blood. Biological fluids such as blood and urine have been shown to contain a large number of components apparently present in all individuals. It is a promotor of the growth of biocontrol bacteria and a metabolite of a new assimilative pathway.

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 158169-14-3 (R)-ethyl 4-hydroxyhexanoate 
• 76695-81-3 ethyl 4-oxo-2-hexynoate 
• 76695-82-4 (R)-ethyl 4-hydroxyhex-2-ynoate 

Relevant academic research and scientific papers

A Facile and General Entry to Optically Active Pheromones and Aromas With γ-Alkyl-γ-lactone Structures. A Study of Some Lactone Derivatives of Pentoses

A new and easy general methodology has been developed to prepare γ-alkyl-α,β-butenolides or γ-alkylbutyrolactones in four and five steps, respectively, from D-ribonolactone as a common chiral starting material.Some of these products have pheromonal activity in insects and are also used as fruit fragrances.A study on several derivatives of D-ribonolactone and 2-deoxy-D-ribonolactone has been carried out in order to explore alternative routes for these syntheses.

THE SYNTHESIS OF NATURALLY OCCURRING 4-ALKYL- AND 4-ALKENYL-γ-LACTONES USING THE ASYMMETRIC REDUCING AGENT B-3-PINANYL-9-BORABICYCLONONANE

4-Hydroxy-2-alkynoates of high enantiomeric purity, available from the reduction of the corresponding ketones with B-3-pinanyl-9-BBN, are converted to 4-substituted-γ-lactones found in beetle and deer pheromones.