Ethyl 2-trans-4-cis-decadienoate

Chemical properties

clear colorless to yellowish liquid

Chemical properties

Ethyl (2E,4Z)-2,4-Decadienoate has been identified in pears and has the typical aroma of Williams pears. Synthesis of ethyl (2E,4Z)-2,4-decadienoate starts from (Z)-1-heptenyl bromide, which is converted into a 1-heptenyllithium cuprate complex with lithium and copper iodide. Reaction with ethyl propiolate yields a mixture of 95% ethyl (2E,4Z)- and 5% ethyl (2E,4E)-2,4-decadienoate. Pure ethyl (2E,4Z)-2,4-decadienoate is obtained by fractional distillation. A biotechnological process for its preparation has been developed.

Chemical properties

Ethyl-trans-2, cis-4-decadienoate has a characteristic pear-like flavor and a light fruity aroma.

Occurrence

Reported found in Bartlett pears, apple, grape, durian (Durio zibethinus), pear brandy, quince and spineless monkey orange (Strychnos madagasc).

The Uses of Ethyl 2-trans-4-cis-decadienoate

Potential applications include the profile enhancement of guava, melon, pear, apple, banana, kiwi, grape, golden delicious apple, fruit cocktail juices, fruit nectar, mamey and other tropical backgrounds.

Definition

ChEBI: Ethyl (2E,4Z)-deca-2,4-dienoate is a fatty acid ethyl ester resulting from the formal condensation of the carboxy group of (2E,4E)-deca-2,4-dienoic acid with the hydroxy group of ethanol. It has a role as a plant metabolite, a flavouring agent, a fragrance and a kairomone. It is functionally related to a (2E,4E)-deca-2,4-dienoic acid.

Aroma threshold values

Detection: 100 ppb. Aroma characteristics at 1.0%: sweet ripe pear, creamy and slightly fatty with fruity, green, waxy apple, fleshy nuances

Taste threshold values

Taste characteristics at 5 ppm: ripe pear, green fruity, waxy apple, tropical notes, fatty golden delicious apple fleshy. Taste characteristics at 20 ppm: green, fruity, apple and pear with waxy tropical nuances.

Synthesis Reference(s)

Tetrahedron, 36, p. 1961, 1980 DOI: 10.1016/0040-4020(80)80209-2

General Description

Natural occurrence: Apple, pear, grape, pear brandy and quince.

Biochem/physiol Actions

Odor at 1.0%

Synthesis

Synthetically via the lithium vinyl cuprates.