gamma-Nonanolactone

Description

γ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste. May be synthesized by reacting methylacry- late and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid; by lactonizα- tion of nonenoic acid.

Chemical properties

gamma-Nonanolactone occurs in many foods and is a pale yellow liquidwith a coconut-like aroma. It has numerous applications, similarly to those of ??-octalactone, in aroma compositions and perfumery.

Chemical properties

γ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste.

Occurrence

Reported found in peaches, apricots, roasted barely, rum, tomato, currants, guava, raisin, papaya, peach, pineapple, blackberry, strawberry jam, asparagus, wheat and crispbread, Camembert cheese, butter, milk, chicken, beef, lamb and pork fat, cooked beef and pork, beer, cognac, whiskies, sherry, grape wines, cocoa, green tea, pecan, oats, soybean, avocado, passion fruit, plum, plumcot, beans, mushroom, starfruit, fenugreek, mango, tamarind, rice, prickly pear, buckwheat, licorice, malt, wort, cherimoya, Bourbon vanilla, shrimp, nectarine, maté and sweet grass oil.

The Uses of gamma-Nonanolactone

(γ-Nonalactone is one of the prominent, odour active compounds present in freshly cooked rice, and also has a coconut-like scent. γ-Nonalactone is also present in aging beers and other fermenting products.

The Uses of gamma-Nonanolactone

In flavor applications, this compound contributes to caramel notes. In fragrance applications, this compound contributes is used in amber, balsam, floral, juniper berry, nutmeg, pine, coconut, maple and oriental notes.

The Uses of gamma-Nonanolactone

(Gamma)-Nonalactone is a synthetic flavoring agent that is a colorless to yellow liquid of strong, coconut-like odor. It is soluble in most fixed oils, mineral oil, and propylene glycol. It is stable in acids and unstable in alkali and should be stored in glass, tin, or aluminum containers. It is used in coconut flavors and has application in gelatins, puddings, baked goods, candy, and ice cream at 11–55 ppm. It is also termed aldehyde c-18.

Preparation

By reacting methylacrylate and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid by lactonization of nonenoic acid

Aroma threshold values

Detection: 7 ppb

Taste threshold values

Taste characteristics at 10 ppm: coconut, creamy, waxy with fatty milky notes

General Description

γ-Nonanoic lactone is an oak lactone commonly found in wines aged in oak barrels. It is the main flavor component of coconut. γ-Nonanoic lactone is also a potential multi-species attractant lure for grain beetle pests.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.