Methyl trans-2-nonenoate

Description

Methyl 2-nonenoate has a characteristic violet-like odor. May be obtained in quantitative yields by treating methyl P-chlorocaproate with sodium acetate, or by dehydrogenating the corresponding saturated ester.

Physical properties

Methyl trans-2-nonenoate is colorless to slightly yellow liquid;strong violet-leaf odor. Stable; soluble in alco-hol. Combustible.

Chemical properties

Methyl 2-Nonenoate is a colorless to pale yellow liquid with a green, floral note. It imparts freshness to floral fragrance compositions and is recommended as a substitute for methyl 2-octynoate.The synthesis consists of a condensation of heptanal withmalonic acid, decarboxylation, and subsequent esterification with methanol.

Occurrence

Methyl trans-2-nonenoate has apparently not been reported to occur in nature.

The Uses of Methyl trans-2-nonenoate

Perfumes.

Preparation

Obtained in quantitative yields by treating methyl β-chlorocaproate with sodium acetate, or by dehydrogenating the corresponding saturated ester.

Definition

ChEBI: Methyl 2-nonenoate is a fatty acid ester.

Taste threshold values

Taste characteristics at 5 ppm: green, waxy, oily, fruity, watermelon rind, pear- and apple-like.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1831, 1989 DOI: 10.1021/jo00269a017
Synthetic Communications, 24, p. 2069, 1994 DOI: 10.1080/00397919408010217
Tetrahedron Letters, 30, p. 6555, 1989 DOI: 10.1016/S0040-4039(01)89020-1

Flammability and Explosibility

Not classified

Trade name

Neofolione (Givaudan).

Metabolism

2-Nonenoic acid produced by the hydrolysis of methyl nonylenate will presumably pass through the normal pathways of fatty acid metabolism (Lehninger, 1970)