| ALLYL CINNAMATE Basic information |
| Identification Description Regulatory Status Usage Natural occurrence |
| Product Name: | ALLYL CINNAMATE |
| Synonyms: | allyl3-phenylacrylate;Allylester kyseliny skoricove;allylesterkyselinyskoricove;Propenyl cinnamate;propenylcinnamate;Vinyl carbinyl cinnamate;vinylcarbinylcinnamate;ALLYL CINNAMATE, 99+% |
| CAS: | 1866-31-5 |
| MF: | C12H12O2 |
| MW: | 188.22 |
| EINECS: | 217-477-8 |
| Product Categories: | |
| Mol File: | 1866-31-5.mol |
| ALLYL CINNAMATE Chemical Properties |
| Boiling point | 150-152 °C15 mm Hg(lit.) |
| density | 1.053 g/mL at 25 °C(lit.) |
| refractive index | n |
| FEMA | 2022 | ALLYL CINNAMATE |
| Fp | >230 °F |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| color | A colourless or pale straw-coloured liquid. |
| JECFA Number | 19 |
| 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 Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| ALLYL CINNAMATE Usage And Synthesis |
| 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
|
| 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)
▼ ▲ Food Category
Usual
Max.
Alcoholic beverages
0.5
2
Baked goods
7.68
10.08
Frozen dairy
2.65
4.65
Gelatins, puddings
2.28
3.83
Nonalcoholic beverages
0.92
1.81
Soft candy
4.38
7.27
|
| 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. |
| 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. |
| ALLYL CINNAMATE Preparation Products And Raw materials |
| Raw materials | Allyl alcohol-->trans-Cinnamic acid |
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