Benzyl cinnamate

Benzyl cinnamate
Skeletal formula of benzyl cinnamate
Space-filling model of the benzyl cinnamate molecule
Names
IUPAC name
Benzyl 3-phenylprop-2-enoate
Other names
Benzylcinnamate; Cinnamein; Benzylcinnamoate; Benzyl 3-phenylpropenoate; 3-phenyl-2-propenoic acid phenylmethyl ester; Cinnamic acid benzyl ester
Identifiers
103-41-3
ChemSpider 4437893
Jmol-3D images Image
PubChem 5273469
Properties
Molecular formula
C16H14O2
Molar mass 238.28 g·mol−1
Appearance White to pale yellow solid[1]
Melting point 34 °C (93 °F; 307 K)[2]
Boiling point 195 °C (383 °F; 468 K) 5 mmHg[2]
Insoluble[1]
Solubility in ethanol 125 g/L
Solubility in glycerin insoluble
Solubility in propylene glycol insoluble
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Benzyl cinnamate is the chemical compound which is the ester derived from cinnamic acid and benzyl alcohol.

Natural occurrence

Occurs in Balsam of Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam.[3]

Synthesis

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.[3]

Uses

Benzyl cinnamate is used in heavy, oriental perfumes and as a fixative.[4] It is used as a flavoring agent.[3]

References

  1. 1.0 1.1 "Specifications for Flavourings". Food and Agricultural Organization.
  2. 2.0 2.1 "Benzyl cinnamate". Sigma-Aldrich.
  3. 3.0 3.1 3.2 George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, pp. 147–148
  4. Karl-Georg Fahlbusch et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59

External links