Cinnamic acid benzyl ester

Structural formula
Simplified structural formula with indefinite geometry at the C = C double bond
General
Surname	Cinnamic acid benzyl ester
other names	Benzyl cinnamate 3-Phenyl-2-propenoic acid benzyl ester BENZYL CINNAMATE ( INCI )
Molecular formula	C 16 H 14 O 2
Brief description	white solid with a sweet odor
External identifiers / databases
CAS number 103-41-3 (not specified) 78277-23-3 [( E ) -form] 28541-02-8 [( Z ) -form] EC number 203-109-3 ECHA InfoCard 100,002,827 PubChem 5273469 ChemSpider 4437893 Wikidata Q9197460
properties
Molar mass	238.28 g mol −1
Physical state	firmly
density	1.109 g cm −3
Melting point	39-39.5 ° C [( E ) -form]
boiling point	350 ° C
Vapor pressure	<0.1 hPa (20 ° C)
solubility	practically insoluble in water (<10 mg l −1 at 20 ° C), glycerol and propylene glycol soluble in ethanol, diethyl ether and various oils
safety instructions
GHS labeling of hazardous substances H and P phrases H: 411 P: 273
Toxicological data	5530 mg kg −1 ( LD 50 ,  rat ,  oral ) > 3000 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cinnamic acid benzyl ester (other name: benzyl cinnamate ) is a chemical compound from the group of carboxylic acid esters . It is the ester of cinnamic acid with benzyl alcohol .

Occurrence

Cinnamic acid benzyl ester is a natural product and occurs in Peruvian and tolu balsam , in Sumatran and Penang benzoin and as the main component of copaiva balsam .

Isomerism

At the C = C double bond, benzyl cinnamate can have a different geometry and accordingly forms two cis - trans isomers which have different properties. In most cases, an unspecified quality is used, which can consist of the ( E ) or ( Z ) form or a mixture thereof.

Isomers of benzyl cinnamate
trans -benzyl cinnamate
cis -cinnamic acid benzyl ester

Extraction and presentation

Cinnamic acid benzyl ester can be obtained synthetically by esterifying cinnamic acid with benzyl alcohol or by reacting benzyl chloride with the sodium salt of cinnamic acid in water or diethylamine .

properties

Benzyl cinnamon ester is a flammable, difficult to ignite, crystalline, white solid with a sweetish odor, which is practically insoluble in water.

use

Benzyl cinnamate is widely used as an odorant in perfume . It is also used as a standard in determining compounds that are commonly added to personal care products, such as UV filters and antimicrobials in environmental samples.

Individual evidence

1. ↑ Entry on BENZYL CINNAMATE in the CosIng database of the EU Commission, accessed on December 28, 2019.
2. ↑ ^{a b c d e f g h i} Entry on benzyl cinnamate in the GESTIS substance database of the IFA , accessed on November 10, 2018(JavaScript required) .
3. ↑ Robert E. Miller, FF Nord: Studies on the Scope of the Reformatsky Reaction , J. Org. Chem. 1951, 16 (5), pp. 728-740; doi: 10.1021 / jo01145a012 .
4. ↑ ^{a b} Benzyl cinnamate data sheet (PDF) from Merck , accessed on November 10, 2018.
5. ↑ ^{a b c} Data sheet Benzyl cinnamate, 99% from Sigma-Aldrich , accessed on November 10, 2018 ( PDF ).
6. ↑ Fred Winter: Handbook of the entire perfumery and cosmetics A scientific-practical presentation of the modern perfumery including the production of the toilet soaps as well as an outline of the applied cosmetics . Springer-Verlag, 2013, ISBN 978-3-662-38143-4 , p. 78 ( limited preview in Google Book search).
7. ↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients . CRC Press, 2004, ISBN 978-1-4200-3787-6 , pp. 1981 ( limited preview in Google Book Search).
8. ↑ Entry on cinnamic acid benzyl ester in the Hazardous Substances Data Bank , accessed on November 10, 2018.