METHYL NONANOATE

Description

Methyl nonanoate has a wine and coconut-like odor. Below 10 ppm, it has a sweet, coconut-like flavor. May be synthesized by heating pelargonic acid with methyl alcohol in the presence of concentrated sulfuric acid and subsequent rectification; or by hydrogenation of 1,5-octadien-carboxylic acid methyl ester using palladium chloride in methanol solution.

Chemical Properties

Methyl nonanoate has a wine and coconut-like odor. Below 10 ppm, it has a sweet, coconut-like flavor

Chemical Properties

Clear colorless liquid

Occurrence

Reported found in orris derivatives, apple, banana, blackberry, baked potato, blue cheeses, beef fat, hop oil, white wine, starfruit, prickly pear, wort, Bourbon vanilla, mountain papaya, spineless monkey orange and rooibus tea (Aspalathus linearis)

Uses

Perfumes, flavors, reference standard for gaschromatography, intermediate in organic synthesis,medical research.

Uses

Methyl nonanoate (Methyl pelargonate) was used in the synthesis of vanillyl nonanoate, a model compound of capsinoids.

Preparation

By heating pelargonic acid with methyl alcohol in the presence of concentrated sulfuric acid and subsequent rectification; or by hydrogenation of 1,5-octadien-carboxylic acid methyl ester using palladium chloride in methanol solution.

Definition

ChEBI: A fatty acid methyl ester obtained from the formal condensation of methanol and nonanoic acid; a colourless liquid with a fruity odour, used in perfumes and flavours, and for medical research.

Taste threshold values

Taste characteristics at 1 to 10 ppm: winey, waxy, green, celery and pear with an unripe fruit nuance.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1213, 1989 DOI: 10.1021/jo00266a046
Tetrahedron Letters, 22, p. 4279, 1981 DOI: 10.1016/S0040-4039(01)82933-6