1866-31-5 Usage
Description
ALLYL CINNAMATE is a synthetic flavoring agent that is a fairly stable, hazy, colorless to light yellow colored liquid with a cherry odor. It is used for its cherry note in flavors and has applications in various food products.
Uses
Used in Food Industry:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to various food products, such as baked goods, candies, alcoholic beverages, frozen dairy, gelatins, puddings, nonalcoholic beverages, and soft candies.
Used in Baked Goods:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to baked goods, with a usual usage range of 7.68 ppm and a maximum usage of 10.08 ppm.
Used in Candies:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to candies, with a usual usage range of 4.38 ppm and a maximum usage of 7.27 ppm.
Used in Alcoholic Beverages:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to alcoholic beverages, with a usual usage of 0.5 ppm and a maximum usage of 2 ppm.
Used in Frozen Dairy:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to frozen dairy products, with a usual usage of 2.65 ppm and a maximum usage of 4.65 ppm.
Used in Gelatins and Puddings:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to gelatins and puddings, with a usual usage of 2.28 ppm and a maximum usage of 3.83 ppm.
Used in Nonalcoholic Beverages:
ALLYL CINNAMATE is used as a flavoring agent for adding a cherry note to nonalcoholic beverages, with a usual usage of 0.92 ppm and a maximum usage of 1.81 ppm.
Occurrence:
ALLYL CINNAMATE has apparently not been reported to occur in nature.
Identification
▼▲
CAS.No.:?
1866-31-5?
FL.No.:?
9.741
FEMA.No.:?
2022
NAS.No.:?
2022
CoE.No.:?
334
EINECS.No.:?
217-477-8?
JECFA.No.:?
19
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).
Natural occurrence
Not reported found in nature.
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.
Synthesis Reference(s)
Tetrahedron, 48, p. 1219, 1992 DOI: 10.1016/S0040-4020(01)90785-9Tetrahedron 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.
Check Digit Verification of cas no
The CAS Registry Mumber 1866-31-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,6 and 6 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1866-31:
(6*1)+(5*8)+(4*6)+(3*6)+(2*3)+(1*1)=95
95 % 10 = 5
So 1866-31-5 is a valid CAS Registry Number.
InChI:InChI=1/C12H12O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h2-9H,1,10H2/b9-8+
1866-31-5Relevant articles and documents
Allyl Isopropenyl Dicarbonate; A Convenient Reagent for the Preparation of Allyl Esters of Carboxylic Acids
Takeda, Kazuyoshi,Akiyama, Akira,Konda, Yaeko,Takayanagi, Hiroaki,Harigaya, Yoshihiro
, p. 113 - 114 (1995)
Allyl isopropenyl dicarbonate(1) reacts with carboxylic acids in the presence of 4-dimethylaminopyridine(DMAP) catalyst to give allyl esters in high yields under mild conditions such as in a near-neutral medium at room temperature.
Trimethylphosphine-Promoted Alcoholysis of α,β-Unsaturated Imides and α,β-Unsaturated Esters
Sato, Haruka,Hosokawa, Seijiro
, p. 1343 - 1349 (2018/01/27)
α,β-Unsaturated imides and α,β-unsaturated esters were found to undergo alcoholysis in the presence of trimethylphosphine. The reaction is initiated by nucleophilic addition of trimethylphosphine to the double bond of the α,β-unsaturated carbonyl compound. Saturated imides also undergo the alcoholysis in the presence of the corresponding α,β-unsaturated imide.
Synthesis of l -octaarginine through microencapsulated palladium-catalyzed allyl ester deprotection
Pérez-López, Ana M.,González-Calderón, Dávir,Occorso, Antonio,Galindo-ángel, Javier,Domínguez-Seglar, José F.,Tamayo, Juan A.,Díaz-Gavilán, Mónica,Gómez-Vidal, José A.
supporting information, p. 2319 - 2322 (2015/08/06)
Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.
