Ethyl cinnamate

Structural formula
General
Surname	Ethyl cinnamate
other names	Ethyl cinnamate; Ethyl 3-phenylprop-2-enoate ( IUPAC ); ETHYL CINNAMATE ( INCI ) ;
Molecular formula	C 11 H 12 O 2
Brief description	colorless liquid
External identifiers / databases
EC number	203-104-6
ECHA InfoCard	100.002.822
PubChem	637758
ChemSpider	553344
Wikidata	Q204182
properties
Molar mass	176.21 g · mol -1
Physical state	liquid
density	1.05 g cm −3 (20 ° C)
Melting point	6-8 ° C
boiling point	271 ° C; 132-134 ° C (13 hPa );
solubility	almost insoluble in water
Refractive index	1.558
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	4000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ethyl cinnamon ester is a colorless liquid, belongs to the aromatic group and is an unsaturated carboxylic acid ester with a trans -substituted carbon-carbon double bond in the side chain. The isomeric ethyl cis -cinnamate is of little importance. The information in this article only relates to ethyl trans- cinnamate.

Occurrence

Cinnamon acid ethyl ester occurs as a flavoring substance in wine.

presentation

Cinnamic acid ethyl ester 2 can be prepared by esterification of cinnamic acid 1 with ethanol are obtained under acid catalysis with sulfuric or hydrochloric acid .

Another way to produce cinnamic acid ethyl ester is the reaction of cinnamic acid with thionyl chloride (this produces cinnamic acid chloride as an intermediate ) and ethanol :

It is also possible to synthesize ethyl cinnamate by a Claisen condensation from benzaldehyde and ethyl acetate .

Reactions

Cinnamic acid ethyl ester reacts with hydrazine hydrate to form cinnamic acid hydrazide . This forms 1-nitroso-5-phenyl-3-pyrazolidone with nitrous acid through a ring-closing reaction.

Individual evidence

↑ Entry on ETHYL CINNAMATE in the CosIng database of the EU Commission, accessed on May 18, 2020.
^ D. Martinetz and R. Hartwig, Taschenbuch der Riechstoffe, 1st edition, Verlag Harri Deutsch, Thun and Frankfurt / Main 1998 ISBN 3-8171-1539-3
↑ ^a ^b ^c ^d ^e data sheet ethyl cinnamate from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
↑ ^a ^b Data sheet of ethyl cinnamate from AlfaAesar, accessed on February 9, 2010 ( PDF )(JavaScript required) .
↑ Entry on ethyl cinnamate at ChemBlink , accessed on February 9, 2010.
↑ ^a ^b C. S. Marvel, WB King: Ethyl Cinnamate In: Organic Syntheses . 9, 1929, p. 38, doi : 10.15227 / orgsyn.009.0038 ; Coll. Vol. 1, 1941, p. 252 ( PDF ).
^ E. Fischer , A. Speier: "Representation of the esters" in reports of the German chemical society , 1895 , 28 , p. 3252ff. ( Full text ).
^ Association of authors: Organikum , 15th edition, VEB Deutscher Verlag der Wissenschaften , Berlin 1976, p. 527.
↑ L. Claisen : "On the representation of room acid and its homologues" in reports of the German chemical society , 1890 , 23 , p. 976ff. ( Full text ).
↑ T. Curtius, PA Bleicher: "About the hydrazide of m-nitrocinnamic acid and its behavior against nitrous acid" in Journal für Praktische Chemie , 1924 , 107 (1-4), pp. 86-98 ( doi : 10.1002 / prac.19241070106 ).

[CosIng-1] Entry on ETHYL CINNAMATE in the CosIng database of the EU Commission, accessed on May 18, 2020.

[2] D. Martinetz and R. Hartwig, Taschenbuch der Riechstoffe, 1st edition, Verlag Harri Deutsch, Thun and Frankfurt / Main 1998 ISBN 3-8171-1539-3

[Sigma-3] ↑ ^a ^b ^c ^d ^e data sheet ethyl cinnamate from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).

[AlfaAesar-4] Data sheet of ethyl cinnamate from AlfaAesar, accessed on February 9, 2010 ( PDF )(JavaScript required) .

[ChemBlink-5] Entry on ethyl cinnamate at ChemBlink , accessed on February 9, 2010.

[Marvel-6] C. S. Marvel, WB King: Ethyl Cinnamate In: Organic Syntheses . 9, 1929, p. 38, doi : 10.15227 / orgsyn.009.0038 ; Coll. Vol. 1, 1941, p. 252 ( PDF ).

[Fischer-7] E. Fischer , A. Speier: "Representation of the esters" in reports of the German chemical society , 1895 , 28 , p. 3252ff. ( Full text ).

[Organikum_15-8] Association of authors: Organikum , 15th edition, VEB Deutscher Verlag der Wissenschaften , Berlin 1976, p. 527.

[Claisen-9] L. Claisen : "On the representation of room acid and its homologues" in reports of the German chemical society , 1890 , 23 , p. 976ff. ( Full text ).

[Curtius-10] T. Curtius, PA Bleicher: "About the hydrazide of m-nitrocinnamic acid and its behavior against nitrous acid" in Journal für Praktische Chemie , 1924 , 107 (1-4), pp. 86-98 ( doi : 10.1002 / prac.19241070106 ).