ALLYL CINNAMATE

Identification

Description

A colorless liquid with peachor apricot-like aroma. It is used as a flavoring agent or adjuvant.

Regulatory Status

CoE: n/a
FDA: 21 CFR 172.515
FDA (other): n/a
JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1996).

Usage

Reported uses (ppm): (FEMA, 1994)

Natural occurrence

Not reported found in nature.

Chemical Properties

A colorless liquid with peach- or apricot-like aroma. It is used as a flavoring agent or adjuvant.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Allyl Cinnamate is a synthetic flavoring agent that is a fairly stable, hazy, colorless to light yellow colored liquid of cherry odor. it is used for its cherry note in flavors and has application in baked goods and candies at 1–2 ppm.

Definition

ChEBI: Allyl cinnamate is a cinnamate ester.

Production Methods

Allyl cinnamate is produced by the direct esterification of allyl alcohol with cinnamic acid.

Preparation

By esterification of cinnamic acid with allyl alcohol in the presence of concentrated H2SO4.

Synthesis Reference(s)

Tetrahedron, 48, p. 1219, 1992 DOI: 10.1016/S0040-4020(01)90785-9
Tetrahedron Letters, 36, p. 113, 1995 DOI: 10.1016/0040-4039(94)02179-F

Safety Profile

Moderately toxic by ingestion. Human skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS and ESTERS

Metabolism

Many esters, including benzyl cinnamate, are rapidly hydrolysed in vivo. Cinnamic acid is known to conjugate with glycine in the animal body, or it may be converted to benzoic acid(Williams, 1959). In the rabbit, cinnamic acid is almost entirely excreted as hippuric acid, without formation of cinnamoyl glycine(El Masry, Smith & Williams, 1956) . In the dog, Quick(1928) observed a large excretion of glucuronide, probably benzoylglucuronide. Dakin (1909) named B-phenyl-B-oxopropionic acid, cinnamoyl glycine and acetophenone as minor metabolites in the dog.

Solubility in organics

Allyl Cinnamate is soluble in alcohol and oils, almost insoluble in Propylene glycol.