Ethyl caprylate

Description

Ethyl caprylate (ethyl octanoate) is a kind of fatty acid ester formed from caprylic acid and ethanol. It is a kind of natural fruit flavoring agent. It is usually included in the alcohol beverage. Among the main flavoring components of None-flavor liquor, the absolute content of ethyl caprylate is not high but its flavoring contributions is higher than ethyl acetate, ethyl lactate, and ethyl butyrate, only lower than ethyl caproate. Only small amount of ethyl caprylate could produce obvious fruit aroma in Nong-flavor liquor. However, excessive content of ethyl caprylate would inhibit the performance of other flavoring components.

Chemical properties

CLEAR COLOURLESS LIQUID

Chemical properties

Ethyl Octanoate is a liquid with a fruity, floral odor. It occurs in many fruits and alcoholic beverages and is used in fruit flavors.

Chemical properties

Ethyl octanoate has a pleasant, fruity, floral odor (wine–apricot note)

Occurrence

Reported found in apple, apricot, orange juice, grapefruit juice, guava, pineapple, cheddar cheese, other cheeses, butter, beer, cognac, rum, whiskey, cider, grape wines, cocoa, coconut meat, passion fruit, mango, pawpaw and mastic gum leaf oil.

The Uses of Ethyl caprylate

Ethyl caprylate is a flavoring and fragrance agent.

The Uses of Ethyl caprylate

manufacture of fruit ethers; constituent of enanthic, cocoic, and cognac ethers.

The Uses of Ethyl caprylate

Ethyl octanoate, found in Burgundy wine, was used to study its partition co-efficient in water in model wine using the headspace method.

Definition

ChEBI: A fatty acid ethyl ester resulting from the formal condensation of octanoic acid with ethanol.

Preparation

Usually prepared by esterification of caprylic acid with ethyl alcohol and sulfuric acid as catalyst; also by alcoholysis of coconut oil in the presence of HCl.

Aroma threshold values

Detection: 5 to 92 ppb

Taste threshold values

Taste characteristics at 5 ppm: waxy, fatty, aldehydic, coconut, creamy and dairy-like.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 6804, 1967 DOI: 10.1021/ja01001a097
The Journal of Organic Chemistry, 42, p. 3209, 1977 DOI: 10.1021/jo00439a026

General Description

Ethyl octanoate is a powerful odourant found in mead (a traditional drink that contains alcohol).

Flammability and Explosibility

Not classified

Safety Profile

Mddly toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Carcinogenicity

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

Metabolism

Aliphatic esters including ethyl caprylate are thought to be readily hydrolysed to the corresponding alcohol and acid, which are then further metabolized (Fassett, 1963). Oral adminis tration of ethyl caprylate to rats produced a ketonuria twice as great as that from acetoacetate, indicating the formation of two fragments for the production of ketone bodies, and it was suggested that caprylic acid was probably broken down by a process involving multiple alternate oxidation (Deuel, Hallman, Butts & Murray, 1936).

References

Powers, John J. "HETEROGENEITY AND TEMPERATURE EFFECTS ON FLAVOR SENSING OF ETHYL CAPRYLATE." Journal of Food Science 42.1(2010):275-276.
Zhibin, L. I., and L. I. Jin. "Analysis of the Content of Ethyl Caprylate in Nong-flavor Liquor and Its Flavoring Contributions." Liquor-Making Science & Technology (2013).