Cinnamic acid methyl ester

Structural formula
General
Surname	Cinnamic acid methyl ester
other names	Methyl cinnamate; Methyl 3-phenylprop-2-enoate ( IUPAC ); METHYL CINNAMATE ( INCI ) ;
Molecular formula	C 10 H 10 O 2
Brief description	white solid
External identifiers / databases
EC number	203-093-8
ECHA InfoCard	100.002.813
PubChem	637520
ChemSpider	21105944
Wikidata	Q204178
properties
Molar mass	162.19 g · mol -1
Physical state	firmly
density	1.32 g cm −3 (20 ° C)
Melting point	33-38 ° C
boiling point	260-262 ° C
solubility	almost insoluble in water; soluble in ethanol , diethyl ether , glycerine ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 317
	P: 280
Toxicological data	5000 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 methyl ester is a white solid and has a smell of balsam and strawberries . Methyl cinnamate is an aromatic compound and is an unsaturated carboxylic acid ester with a trans -substituted carbon-carbon double bond in the side chain. The isomeric methyl cis -cinnamate is of little importance. The information in this article relates only to methyl trans cinnamate.

Occurrence

Eucalyptus ( Eucalyptus olida )

The ester occurs naturally in various plants, e.g. B. in strawberries and different types of basil . The eucalyptus species Eucalyptus olida has the largest amount of cinnamic acid methyl ester.

presentation

Cinnamic acid methyl ester can be prepared by esterification of cinnamic acid with methanol and sulfuric acid as a catalyst are recovered.

Cinnamic acid methyl ester can also be obtained by a Claisen condensation of benzaldehyde and methyl acetate in the presence of sodium.

Another possible synthesis is the Wittig reaction , which forms the ester via a phosphonium salt and an addition reaction with benzaldehyde.

Individual evidence

↑ Entry on METHYL CINNAMATE in the CosIng database of the EU Commission, accessed on March 11, 2020.
↑ ^a ^b ^c ^d data sheet cinnamic acid methyl ester from Sigma-Aldrich , accessed on August 6, 2013 ( PDF ).
↑ ^a ^b ^c Entry on methyl cinnamate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b Data sheet of methyl cinnamate from Acros, accessed on February 19, 2010.
↑ Data sheet cinnamic acid methyl ester from AlfaAesar, accessed on February 9, 2010 ( PDF )(JavaScript required) .
↑ Amparo Viña, Elizabeth Murillo: Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia , in: J. Braz. Chem. Soc. , 2003 , 14 (5); doi: 10.1590 / S0103-50532003000500008 .
↑ DJ Boland, JJ Brophy, APN House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6 .
↑ Test protocol ( Memento from May 3, 2005 in the Internet Archive ) (PDF), Ruhr University Bochum.

[CosIng-1] Entry on METHYL CINNAMATE in the CosIng database of the EU Commission, accessed on March 11, 2020.

[Sigma-2] ta sheet cinnamic acid methyl ester from Sigma-Aldrich , accessed on August 6, 2013 ( PDF ).

[GESTIS-3] Entry on methyl cinnamate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Acros-4] Data sheet of methyl cinnamate from Acros, accessed on February 19, 2010.

[AlfaAesar-5] Data sheet cinnamic acid methyl ester from AlfaAesar, accessed on February 9, 2010 ( PDF )(JavaScript required) .

[Murillo-6] Amparo Viña, Elizabeth Murillo: Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Colombia , in: J. Braz. Chem. Soc. , 2003 , 14 (5); doi: 10.1590 / S0103-50532003000500008 .

[Boland-7] DJ Boland, JJ Brophy, APN House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6 .

[Enterlein-8] Test protocol ( Memento from May 3, 2005 in the Internet Archive ) (PDF), Ruhr University Bochum.