Ethyl Cinnamate

Product Name:

Ethyl cinnamate

CAS:

103-36-6

MF:

C11H12O2

MW:

176.21

EINECS:

203-104-6

Mol File:

103-36-6.mol

Melting point 

6-8 °C(lit.)

Boiling point 

271 °C(lit.)

density 

1.049 g/mL at 20 °C(lit.)

FEMA 

2430 | ETHYL CINNAMATE

refractive index 

n20/D 1.558(lit.)

Fp 

>230 °F

storage temp. 

Refrigerator (+4°C)

form 

Liquid

color 

Clear colorless to pale yellow

Water Solubility 

insoluble

Merck 

14,2299

JECFA Number

659

BRN 

1238804

Stability:

Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Combustible.

CAS DataBase Reference

103-36-6(CAS DataBase Reference)

NIST Chemistry Reference

trans-Ethyl cinnamate(103-36-6)

EPA Substance Registry System

Ethyl cinnamate (103-36-6)

Risk Statements 

20-22

Safety Statements 

23-24/25

WGK Germany 

1

RTECS 

GD9010000

TSCA 

Yes

HS Code 

29163990

Chemical properties

It appears as nearly colorless, transparent oily liquid with light, long lasting cinnamon and strawberry aroma and sweet honey aroma. It has no optical activity with the melting point of 12 ° C, the boiling point of 272 ° C and the flash point of 93.5 ° C. It is miscible in ethanol, ether and most non-volatile oils. It is almost insoluble in glycerol and water. It is slightly soluble in propylene glycol.
Its natural product exists in the Soviet Union balsam, galangal oil and so on.

Production method

It can be obtained through the esterification between cinnamic acid and ethanol in the presence of sulfuric acid with a yield of about 60%. It can also be derived through the reaction bewteen benzaldehyde and ethyl acetate.
It can be obtained through the reaction between benzaldehyde and ethyl acetate in the presence of sodium metal.
It is derived from the heating of cinnamic acid, ethanol and sulfuric acid to 100 °C in the presence of aluminum sulfate.

Description

Ethyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon. Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note".
The p-methoxy derivative is reported to be a mono amine oxidase inhibitor.

Chemical Properties

Ethyl cinnamate has a sweet balsami honey-note odor.

Chemical Properties

colourless liquid

Uses

Perfumery, flavoring extracts.

Production Methods

Ethyl 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 .

Preparation

By heating to 100°C cinnamic acid, alcohol and sulfuric acid in the presence of aluminum sulfate; also by Claisen con[1]densation of benzaldehyde and ethyl acetate

Aroma threshold values

Detection: 17 to 40 ppb

Taste threshold values

Taste characteristics at 20 ppm: balsamic, powdery, fruity, berry, punch, spice, sweet and green.

Raw materials

Sodium-->Aluminium sulfate-->trans-Cinnamic acid-->Hydrochloric acid alcohol

Preparation Products

Ozagrel-->3-Phenyl-1-propanol-->Ethyl 3-phenylpropionate