4-Dodecanolide

Chemical properties

γ-Dodecalactone has a fatty, peachy, somewhat musky odor and buttery, peach-like flavor

Occurrence

Reported found in apricot, cooked pork, milk products, peach, bilberry, guava fruit, papaya, pineapple, fresh blackberry, strawberry, celery leaves and stalks, celery root, blue cheeses, cheddar cheese, Swiss cheese, meats, beer, rum, mushrooms, plum brandy, quince, chervil, naranjilla fruit and other natural sources

The Uses of 4-Dodecanolide

4-Dodecanolide was one of the organic compounds from meat charbroiling operations studied.

Preparation

From 1-dodecen-12-oic acid with H2SO4 at 90°C; from 4-hydroxydodecanoic acid by lactonization; also from methylacrylate and octanol

Definition

ChEBI: Xi-Dihydro-5-octyl-2(3H)-furanone is a gamma-lactone.

Aroma threshold values

Detection: 7 ppb; aroma characteristics at 1.0%; sweet, creamy, fruity peach and apricot, lactonic, with dairy waxy and fatty nuances.

Taste threshold values

Taste characteristics at 1 to 10 ppm: sweet, fruity peach, milky fatty and waxy with a pulpy fruity mouthfeel.

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 3745, 1986 DOI: 10.1021/ja00273a032
Organic Syntheses, Coll. Vol. 7, p. 400, 1990

Safety Profile

A skin irritant. When heated todecomposition it emits acrid smoke and irritating vapors