Chemical Properties
δ-Decalactone has an oily, peach odor and taste.
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.
Occurrence
Reported found in rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses,
butter, milk, milk powder, mutton fat, mango and nectarine.
Uses
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.
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.
Definition
ChEBI: A delta-lactone that is 5-valerolactone substituted by a pentyl group at position 6.
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-2
H-pyran-2-one) has been reported.
Flammability and Explosibility
Not classified
Synthesis
From hexylethylene oxide and sodium malonic ester; also from decanoic acid.
