ALLYL CINNAMATE

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 Structure
ALLYL CINNAMATE Chemical Properties
Boiling point 150-152 °C15 mm Hg(lit.)
density 1.053 g/mL at 25 °C(lit.)
FEMA 2022 | ALLYL CINNAMATE
refractive index n20/D 1.566(lit.)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
color A colourless or pale straw-coloured liquid.
Odorat 100.00 %. fruity balsamic pineapple spicy cinnamyl plum apricot peach
Odor Typefruity
JECFA Number19
LogP2.93
CAS DataBase Reference1866-31-5(CAS DataBase Reference)
EPA Substance Registry System2-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
toxicityThe 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
ProviderLanguage
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
 
 
DescriptionA colorless liquid with peachor apricot-like aroma. It is used as a flavoring agent or adjuvant.
Regulatory StatusCoE: 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).


UsageReported 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 occurrenceNot reported found in nature.
Chemical PropertiesA colorless liquid with peach- or apricot-like aroma. It is used as a flavoring agent or adjuvant.
OccurrenceHas apparently not been reported to occur in nature.
UsesAllyl 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.
PreparationBy esterification of cinnamic acid with allyl alcohol in the presence of concentrated H2SO4.
Production MethodsAllyl cinnamate is produced by the direct esterification of allyl alcohol with cinnamic acid.
DefinitionChEBI: 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 ProfileModerately toxic by ingestion. Human skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS and ESTERS
MetabolismMany 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 materialsAllyl alcohol-->trans-Cinnamic acid
6-CHLORO-2H-CHROMENE-3-CARBOXYLIC ACID ALLYL ESTER (6R,7S)-7α-[[(R)-5-Amino-5-carboxy-1-oxopentyl]amino]-3-[[[(E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid SALOR-INT L160784-1EA (6R,7S)-7α-[(4-Carboxy-1-oxobutyl)amino]-7-methoxy-8-oxo-3-[[[(E)-1-oxo-3-[4-(sulfooxy)phenyl]-2-propenyl]oxy]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1,1-dimethylallyl caffeic acid ester LINALYL CINNAMATE KAFFEESA URE-1,1-DIMETHYLALLYLESTER >95% (HPLC) MELILOTICANHYDRIDE Cinnamyl cinnamate (6R,7S)-7α-[[(R)-5-Amino-5-carboxy-1-oxopentyl]amino]-7-methoxy-8-oxo-3-[[[(E)-1-oxo-3-[4-(sulfooxy)phenyl]-2-propenyl]oxy]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7S)-7-[(4-Carboxy-1-oxobutyl)amino]-7-methoxy-3-[[[(E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]methyl]cepham-3-ene-4-carboxylic acid CDC 3,4,5-TRIMETHOXYCINNAMIC ACID ANHYDRIDE 3,5-DINITROCINNAMIC ACID ALLYL ESTER (E)-3-(3,4-BIS-ALLYLOXY-PHENYL)-ACRYLIC ACID ALLYL ESTER ALLYL CINNAMATE TAXININE GERANYL CINNAMATE

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