Benzyl cinnamate Property

Melting point:

34-37 °C (lit.)

Boiling point:

195-200 °C/5 mmHg (lit.)

Density 

1.11

vapor pressure 

<0.1 hPa (20 °C)

FEMA 

2142 | BENZYL CINNAMATE

refractive index 

1.4025-1.4045

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

alcohol: soluble(lit.)

form 

Crystalline Mass or Liquid After Melting

color 

Clear colorless to yellow

Odor

aromatic odor

Odor Type

balsamic

Water Solubility 

PRACTICALLY INSOLUBLE

Merck 

14,1130

JECFA Number

670

BRN 

2051339

LogP

4.18 at 23.7℃

CAS DataBase Reference

103-41-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzyl cinnamate(103-41-3)

EPA Substance Registry System

Benzyl cinnamate (103-41-3)

Safety

Risk Statements 

36/37/38

Safety Statements 

22-24/25

RIDADR 

3077

WGK Germany 

2

RTECS 

GD8400000

TSCA 

Yes

HS Code 

29163900

Hazardous Substances Data

103-41-3(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 5530 mg/kg (Jenner)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

Benzyl cinnamate Chemical Properties,Usage,Production

Chemical Properties

Clear colorless to yellowish crystalline mass or liquid after meltin

Chemical Properties

Benzyl Cinnamate occurs in balsams and balsam oils. It forms white, sweet-balsamic-smelling crystals (mp 35-36°C). Benzyl cinnamate is used as a fixative in perfumes and as a component of heavy, oriental perfumes.

Chemical Properties

Benzyl cinnamate has a sweet, balsamic odor and a honey-like taste.

Occurrence

Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam.

Uses

Benzyl cinnamate has been employed as internal standard during the determination of compounds commonly added to personal care products such as UV filters and antimicrobial agents in environmental samples.

Uses

Mild. sweet-balsamic and somewhat floral odor of great tenacity. Used quite frequently in perfumery, mainly as a fixative, and particularly in perfumes for Talcum (powders). It blends well with floral bases, spicy fragrances and Ambre types.
Used in flavor compositions for imitation Apricot, Cherry, Chocolate, Honey, Peach, Pineapple, Liquor, Raspberry, Rum, Prune, etc.
Concentration may be little more than traces, usually about 6 ppm, except in chewing gum: up to 125 ppm.

Definition

ChEBI: Benzyl cinnamate is the cinnamate ester derived from cinnamic acid and benzyl alcohol. Occuring in Balsam of Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam, it is used in heavy oriental perfumes, as a fixative and as a flavouring agent. It has a role as a flavouring agent, a fragrance, a fixative, an antigen and an epitope.

Preparation

By heating benzyl chloride and excess sodium cinnamate in water to 100 to 115°C; by heating sodium cinnamate with an excess of benzyl chloride in the presence of diethylamine.

Production Methods

Benzyl cinnamate is produced by the direct esterification of benzyl alcohol with cinnamic acid.

Taste threshold values

Taste characteristics at 50 ppm: spicy, floral, fruity, balsamic.

General Description

Benzyl cinnamate is widely used as a fragrance ingredient.

Hazard

Moderately toxic.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion. Amild allergen and skin irritant. Combustible liquid. When heated to decomposition it emits acridsmoke and irritating fumes.

target

Immunology & Inflammation related

Metabolism

See monograph on Benzyl alcohol (p. 1011).

Purification Methods

Recrystallise the ester to a constant melting point from 95% EtOH. It has the odour of balsam. Alternatively dissolve it in Et2O, wash it with 10% aqueous Na2CO3, H2O, dry (Na2SO4), evaporate and fractionate it under reduced pressure using a short Vigreux column (p 11). It decomposes when boiled at atmospheric pressure. [Eliel & Anderson J Am Chem Soc 74 547 1952, Bender & Zerner J Am Chem Soc 84 2550 1962, Beilstein 9 IV 2012.]