gamma-Octanoic lactone

Description

y-Octalactone has a strong, fruity odor reminiscent of coconut with a very sweet taste. This substance may be prepared synthetically from epoxy-1,2-hexane and sodio-malonic ester; after saponification the oxyacid is extracted with ether and is lactonized.

Chemical properties

CLEAR COLOURLESS LIQUID

Chemical properties

gamma-Octanoic lactone occurs as an aroma constituent in many processed and unprocessed foods. It is a pale yellow liquid with a fruity/coconut-like odor and is used both in aroma compositions and in heavy blossom perfumes.

Chemical properties

γ-Octalactone has a fruity odor reminiscent of coconut and a very sweet taste.

Occurrence

Reported found in apricot, peach, blue cheese, butter, cooked chicken and cooked pork, licorice, milk, raspberry, roasted barley, and roasted filbert.

The Uses of gamma-Octanoic lactone

(Gamma)-Octalactone is a synthetic flavoring agent that is a stable, colorless to slightly yellow liquid of peach odor. It should be stored in glass or tin containers. It is used in flavors for peach with applications in baked goods, candy, and ice cream at 5–17 ppm.

The Uses of gamma-Octanoic lactone

4-Octanolide is one of the fine organic aerosol emitted from meat cooking operations that was examined by high-resolution gas chromatography.

Definition

ChEBI: Gamma-octalactone is a gamma-lactone that is oxolan-2-one substituted by a butyl group at position 5. It is a volatile compound found in peaches, mangoes, beef and ham. It has a role as a fungal metabolite, a mouse metabolite, a mammalian metabolite, an insect attractant, a plant metabolite and a flavouring agent. It is a gamma-lactone, a tetrahydrofuranone and a volatile organic compound.

Aroma threshold values

Detection: 7 ppb; aroma characteristics at 1.0%: sweet, fatty, creamy, coconut, lactonic and coumarinic.

Taste threshold values

Taste characteristics at 1 to 10 ppm: coconut, fatty, creamy, coumarinic, with a strong creamy and waxy mouthfeel.

Synthesis Reference(s)

Chemistry Letters, 23, p. 53, 1994
The Journal of Organic Chemistry, 52, p. 4319, 1987 DOI: 10.1021/jo00228a032
Tetrahedron Letters, 19, p. 419, 1978 DOI: 10.1016/S0040-4039(01)91443-1

General Description

γ--Octalactone is one of the flavor constituents of peaches, oranges and sweet fortified wines.

Flammability and Explosibility

Not classified

Safety Profile

Mildly toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Prepared synthetically from epoxy-1,2-hexane and sodio-malonic ester; after saponification, the oxyacid is extracted with ether and is lactonized.