Ethyl Hexanoate

Chemical properties

CLEAR COLOURLESS LIQUID

Chemical properties

Ethyl Hexanoate is a colorless liquid with a strong fruity odor, reminiscent of pineapples. It occurs in many fruits and is used in small amounts for floral, fruity notes in perfume compositions and in larger quantities in fruit flavors.

Chemical properties

Ethyl hexanoate has a powerful, fruity odor with a pineapple–banana note. It has been also reported to have a winy odor.

Occurrence

Reported found in strawberry, rum, bourbon, cocoa, kiwi fruit, black currant, apple, orange and grapefruit juice, guava, Vitis vinifera, pineapple, strawberry jam, clove bud, cheeses, cognac, whiskies, grape wines, passion fruit juice, mango, fruit brandies, figs, corn oil, mountain papaya, pawpaw and mastic gum leaf oil.

The Uses of Ethyl Hexanoate

Ethyl hexanoate may be used as an analytical reference standard for the determination of the analyte in wine and beer samples by chromatography based techniques.

The Uses of Ethyl Hexanoate

manufacture of artificial fruit flavors.

The Uses of Ethyl Hexanoate

Ethyl Caproate is used in the synthesis of novel EP2/EP4 dual agonist of γ-lactam prostaglandin E1 analogs. Also used as a chemical reagent in the synthesis of PPARα antagonists in the treatment of metabolic diseases.

Definition

ChEBI: A fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol.

Preparation

By esterification of caproic acid with ethyl alcohol in the presence of concentrated H2SO4 or HCl

Aroma threshold values

Detection: 0.3 to 5 ppb

Taste threshold values

Taste characteristics at 10 ppm: fruity and waxy with a tropical nuance.

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 818, 1968 DOI: 10.1021/ja01005a064
Synthetic Communications, 14, p. 77, 1984 DOI: 10.1080/00397918408060867
Synthesis, p. 929, 1978 DOI: 10.1055/s-1978-24945

General Description

Ethyl hexanoate is one of the odorants contributing to the typical guava aroma. It also contributes to the fresh strawberry aroma.

Safety Profile

A skin irritant. Flammable liquid when exposed to heat or flame; can react with oxidzing materials. When heated to decomposition it emits acrid smoke and irritating fumes. To fight fire, use CO2, foam, dry chemical. See also ESTERS.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

Metabolism

Aliphatic esters, including ethyl caproate, are thought to be readily hydrolysed to the corresponding alcohol and acid, which are then further metabolized (Fassett, 1963). Ethyl caproate administered orally to rats produced a uniform ketonuria and it was considered probable that caproic acid was broken down chiefly by ?-oxidation (Deuel, Hallman, Butts & Murray, 1936). When 2 g ethyl caproate dissolved in aqueous ethanol was fed directly into the rumen of a cow, 0.003°/ was transferred to the milk, reaching a maximum level of 60 /fg/litre after 2-4 hr (Honkanen, Karvonen & Virtanen, 1964). The energy from ethyl caproate was 52% available when the ester was fed to four chicks at a level of 5% in the diet (Yoshida et al. 1970).

Solubility in organics

Soluble in oils and alcohol. Poorly soluble in Ropylene glycol, insoluble in Glycerin.