5-Decanolide

Chemical properties

clear colorless to light yellow oily liquid

Chemical properties

5-Decanolide is a flavor constituent of many types of fruit, cheese, and other dairy products. It is a colorless, viscous liquid with a creamy-coconut, peach-like aroma.

Chemical properties

δ-Decalactone has an oily, peach odor and taste.

Occurrence

Reported found in rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses, butter, milk, milk powder, mutton fat, mango and nectarine.

The Uses of 5-Decanolide

Used in pharmaceutical preparations, feed additive, flavorings agent. Also used by food and flavor industries for its coconut fragrance and taste. It is also used as a reagent in the synthesis of (±)-Massoilactone (M197600); a chemical component with antibacterial activity found in volatile oils.

Definition

ChEBI: A delta-lactone that is 5-valerolactone substituted by a pentyl group at position 6.

Preparation

δ-Decalactone can be prepared by peracid oxidation of 2-pentylcyclopentanone. (R)-δ-decalactone is obtained in high optical purity by starting from (R)-2- pentylcyclopentanone . Hydrogenation or fermentation of massoia lactone is also a practicable method to produce this enantiomer.
A newer development for the preparation ofδ-decalactone describes a carboxylation of 1-nonen-4-ol with carbon monoxide in the presence of a homogenous palladium catalyst in an aqueous system.

Aroma threshold values

Detection: 100 ppb

Taste threshold values

Taste characteristics at 2 ppm: waxy, coconut, lactonic, fatty, creamy, nutty and fruity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 462, 1990 DOI: 10.1021/jo00289a016

General Description

Measurement of optical rotatory dispersion and circular dichroism of (+) 5-decanolide (tetrahydro-6-pentyl-2H-pyran-2-one) has been reported.

Flammability and Explosibility

Not classified

Synthesis

From hexylethylene oxide and sodium malonic ester; also from decanoic acid.