Ethyl cinnamate

Ethyl cinnamate Basic information
Product Name:Ethyl cinnamate
Synonyms:(E/Z)-3-Phenyl-acrylicacidethylester;2-Propenoic acid, 3-phenyl-, ethyl ester;2-Propenoicacid,3-phenyl-,ethylester;3-phenyl-2-propenoicaciethylester;cis/trans-ethylcinnamate;Ethyl (2E)-3-phenyl-2-propenoate;Ethyl 3-phenyl-2-propenoate;Ethyl 3-phenylacrylate
CAS:103-36-6
MF:C11H12O2
MW:176.21
EINECS:203-104-6
Product Categories:Aromatic Cinnamic Acids, Esters and Derivatives;Alphabetical Listings;Certified Natural ProductsFlavors and Fragrances;E-F;Flavors and Fragrances;C10 to C11;Carbonyl Compounds;Esters;Cosmetics;103-36-6
Mol File:103-36-6.mol
Ethyl cinnamate Structure
Ethyl cinnamate Chemical Properties
Melting point 6-8 °C (lit.)
Boiling point 271 °C (lit.)
density 1.049 g/mL at 20 °C (lit.)
vapor pressure 6Pa at 20℃
FEMA 2430 | ETHYL CINNAMATE
refractive index n20/D 1.558(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form Liquid
color Clear colorless to pale yellow
Odorat 100.00 %. sweet balsam fruity spicy powdery berry plum
Odor Typebalsamic
Water Solubility insoluble
Merck 14,2299
JECFA Number659
BRN 1238804
Stability:Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible.
LogP3.01 at 23.6℃
CAS DataBase Reference103-36-6(CAS DataBase Reference)
NIST Chemistry Referencetrans-Ethyl cinnamate(103-36-6)
EPA Substance Registry SystemEthyl cinnamate (103-36-6)
Safety Information
Risk Statements 20-22
Safety Statements 23-24/25
WGK Germany 1
RTECS GD9010000
TSCA Yes
HS Code 29163990
toxicityThe acute oral LD50 value in rats was reported as 7.8 g/kg (7.41-8.19 g/kg) (Russell, 1973). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Russell, 1973).
MSDS Information
ProviderLanguage
Ethyl 3-phenyl propenoate English
ACROS English
SigmaAldrich English
ALFA English
Ethyl cinnamate Usage And Synthesis
DescriptionEthyl cinnamate is the ester of cinnamic acid and ethanol, and is typically found in the essential oil of cinnamon. It is noteworthy that pure ethyl cinnamate has an aroma of cinnamon, complicated by balsamic and red fruit nuances,all of which can be characteristic of a fine Nebbiolo wine's aromatics.
Chemical PropertiesEthyl Cinnamate, ethyl 3-phenylacrylate, C6H5CH=CHCOOC2H5.Occurs naturally in storax and the volatile oil of Koempferia galanga.The commercial product is a colourless liquid, invariably prepared artificially. Has a sweet balsami honey-note odor of great persistence. Ethyl cinnamate is useful in Oriental bouquets, and in combination with clary sage and citrus oils will make delightful amber colognes.
OccurrenceNormally occurring in the trans-form; a cis-form also exists. Reported found in Oriental styrax, in the oil of Campheria galanga and in the rhizomes of Hedychium spicatum. Also reported found in cherry, American cranberry, pineapple, guava, strawberry, fresh blackberry, strawberry jam, soybean, yellow passion fruit juice, hybrid passion fruit juice, apple brandy, quince, prickly pear, strawberry wine, Bourbon vanilla, sea buckthorn, cinnamon leaf and root bark, clove, brandy, rum, sherry, grape wines, cocoa, soybean and other natural sources.
UsesEthyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.
PreparationBy heating to 100°C cinnamic acid, alcohol and sulfuric acid in the presence of aluminum sulfate; also by Claisen condensation of benzaldehyde and ethyl acetate
DefinitionChEBI: Ethyl cinnamate is an alkyl cinnamate and an ethyl ester.
Production MethodsEthyl cinnamate is found in storax oil, Kaempferia galanga, and several other oils. It is produced by the direct esterification esterification of ethanol with cinnamic acid under azeotropic conditions or by Claisen-type condensation of ethyl acetate and benzaldeyde in the presence of sodium metal .
Aroma threshold valuesDetection: 17 to 40 ppb
Taste threshold valuesTaste characteristics at 20 ppm: balsamic, powdery, fruity, berry, punch, spice, sweet and green.
Synthesis Reference(s)Journal of the American Chemical Society, 110, p. 2655, 1988 DOI: 10.1021/ja00216a053
Tetrahedron Letters, 30, p. 5153, 1989 DOI: 10.1016/S0040-4039(01)93472-0
General DescriptionEthyl cinnamate can be used as a flavoring and fragrance ingredient. It is one of the key odor components reported in Burgundy Pinot noir wines.
Biochem/physiol ActionsEthyl cinnamate inhibits the growth of Chlorella pyrenoidosa.
Safety ProfileModerately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS
Purification MethodsWash the ester with aqueous 10% Na2CO3, then water, dry (MgSO4), and distil it. The purified ester is saponified with aqueous KOH, and, after acidifying the solution, cinnamic acid is isolated, washed and dried. The ester is reformed by refluxing for 15hours the cinnamic acid (25g) with absolute EtOH (23g), conc H2SO4 (4g) and dry *benzene (100mL), after which it is isolated, washed, dried and distilled under reduced pressure [Jeffery & Vogel J Chem Soc 658 1958]. [Beilstein 9 IV 2006.]
Methyl cinnamate Propyl cinnamate Trinexapac-ethyl Ethanol Ethyl 4-methylcinnamate CINNAMATE Ethyl propionate Ethyl formate Octyl 4-methoxycinnamate Diphenyl ether Ethylparaben Cinnamyl cinnamate P-methoxyl ethyl cinnamate 2-Ethoxyethanol Diethyl ether Ethyl acetate Phenyl salicylate Phenylacetic acid

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.