Ethyl benzoate

Description

Ethyl benzoate is an ester produced via the condensation of benzoic acid and ethanol. This compound is a colorless liquid, characterized by its near-insolubility in water and miscibility with most organic solvents. As a volatile ester, it possesses a characteristic aromatic profile, often likened to wintergreen mint. It is consequently employed as a component in certain artificial fruit flavorings.

Chemical properties

Ethyl benzoate is a colourless liquid that has a somewhat fruity odor similar to ylang-ylang, but milder than methyl benzoate. Soluble in ethanol, ethyl ether, petroleum ether, propylene glycol, mineral oil and most non-volatile oils, insoluble in water and glycerin.

Occurrence

Reported found in volatiles from hard, mature peaches, pineapple and currant. Also reported found in apple juice, banana, guava, cranberry, raspberry, sweet cherry, Parmesan cheese, butter, milk, white wine, red wine, cider, whiskies, cocoa, black tea, fresh plum, apple brandy, cherry brandy, Bourbon vanilla, naranjilla fruit, ceriman or pinanona, pimento berry, olive and passion fruit.

The Uses of Ethyl benzoate

Ethyl benzoate, due to the presence of volatile ester groups in its structure, is a fragrance and flavoring agent. In the perfume industry, it is known as "Niober fragrance" and is used to produce artificial fruit flavorings. Its applications include use as a perfume flavoring and food flavoring agent, where it is the active ingredient in artificial fruit flavorings. Furthermore, it is added to cosmetics and personal care products as a fragrance ingredient and preservative.

Preparation

By esterification of ethyl alcohol and benzoic acid in the presence of anhydrous aluminum sulfate and a trace of sulfuric acid; by transesterification of methyl benzoate with ethanol in the presence of potassium ethylate

Definition

ChEBI: Ethyl benzoate is a benzoate ester obtained by condensation of benzoic acid and ethanol. It is a volatile oil component found in ripe kiwifruit, cranberry juice, and palm kernel oil. It has a role as a flavouring agent, a fragrance and a volatile oil component. It is a benzoate ester and an ethyl ester.

Aroma threshold values

Detection: 100 ppb; recognition: 150 ppb

Taste threshold values

Taste characteristics at 30 ppm: sweet, medicinal, green, minty, fruity, birch beer and wintergreen-like.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1703, 1960 DOI: 10.1021/jo01080a004
Synthetic Communications, 20, p. 2267, 1990 DOI: 10.1080/00397919008053167
Tetrahedron Letters, 22, p. 1509, 1981 DOI: 10.1016/S0040-4039(01)90363-6

General Description

Natural occurrence: Feijoa, guava, plum, raspberry, rum, strawberry, Virginia tobacco.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

Taste at 10 ppm

Safety Profile

Moderately toxic by ingestion. Mildly toxic by skin contact. A skin and eye irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS