Benzyl cinnamate

Benzyl cinnamate
Skeletal formula of benzyl cinnamate
Space-filling model of the benzyl cinnamate molecule
Names
Preferred IUPAC name
Benzyl (2E)-3-phenylprop-2-enoate
Other names
Benzyl cinnamate
Cinnamein
Benzyl cinnamoate
Benzyl 3-phenylpropenoate
3-Phenyl-2-propenoic acid phenylmethyl ester
Cinnamic acid benzyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.827 Edit this at Wikidata
UNII
  • InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+
    Key: NGHOLYJTSCBCGC-VAWYXSNFSA-N
  • C1=CC=C(C=C1)COC(=O)C=CC2=CC=CC=C2
Properties
C16H14O2
Molar mass 238.286 g·mol−1
Appearance White to pale yellow solid
Melting point 34–37 °C (93–99 °F; 307–310 K)
Boiling point 195–200 °C (383–392 °F; 468–473 K) 5 mmHg
Insoluble
Solubility in ethanol 125 g/L
Solubility in glycerin Insoluble
Solubility in propylene glycol Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Natural occurrence

Balsam is the major producer of benzyl cinnamate. It is used as an ingredient in the medicated cream product Sudocrem.

Uses

It is used as a flavoring agent. It has a low odour smelling faintly sweet, balsamic, floral, fruity, cherry, spicy, and powdery.

It is used pharmaceutically as an antibacterial and antifungal.

References

  1. 1 2 "Specifications for Flavourings". Food and Agriculture Organization. Archived from the original on 2015-09-24. Retrieved 2014-02-20.
  2. 1 2 "Benzyl cinnamate". Sigma-Aldrich.
  3. 1 2 George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, pp. 147–148
  4. ↑ "Sudocrem Antiseptic Healing Cream - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 11 June 2021.
  5. ↑ "benzyl cinnamate". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  6. ↑ Korošec, B.; Sova, M.; Turk, S.; Kraševec, N.; Novak, M.; Lah, L.; Stojan, J.; Podobnik, B.; Berne, S.; Zupanec, N.; Bunc, M.; Gobec, S.; Komel, R. (2014). "Antifungal activity of cinnamic acid derivatives involves inhibition of benzoate 4-hydroxylase (CYP53)". Journal of Applied Microbiology. 116 (4): 955–966. doi:10.1111/jam.12417. ISSN 1365-2672. PMID 24314266.