ALLYL CINNAMATE Chemical Properties

Boiling point:

150-152 °C15 mm Hg(lit.)

Density 

1.053 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.566(lit.)

FEMA 

2022 | ALLYL CINNAMATE

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Insoluble in water, soluble in alcohol and oils, almost insoluble in Propylene glycol.

color 

A colourless or pale straw-coloured liquid.

Odor

at 100.00 %. fruity balsamic pineapple spicy cinnamyl plum apricot peach

Odor Type

fruity

JECFA Number

19

LogP

2.93

CAS DataBase Reference

1866-31-5(CAS DataBase Reference)

EPA Substance Registry System

2-Propenoic acid, 3-phenyl-, 2-propenyl ester (1866-31-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

GD8050000

HS Code 

29163100

Toxicity

The acute oral LD₅₀ value in rats was reported as 1.52 g/kg and the acute dermal LD₅₀ value in rabbits as less than 5 g/kg(Levenstein, 1975).

MSDS

• Language:English Provider:SigmaAldrich

ALLYL CINNAMATE Usage And Synthesis

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.

Preparation

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

Production Methods

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

Definition

ChEBI: Allyl cinnamate is a cinnamate ester.

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.

ALLYL CINNAMATE(1866-31-5)Related Product Information

• trans-Cinnamic acid
• Cinnamic acid
• Cinnamamide
• Methyl cinnamate
• Cinnamonitrile
• Cinnamyl alcohol
• Benzyl cinnamate
• Ethyl cinnamate
• Cinnamyl chloride
• Cinnamaldehyde
• Isobutyl cinnamate
• Potassium cinnamate
• ISOPROPYL CINNAMATE, 98
• Phenethyl cinnamate
• N-BUTYL CINNAMATE
• Cinnamyl chloride
• Cinnamyl bromide
• Propyl cinnamate