Benzyl cinnamate

Last updated
Benzyl cinnamate
Benzyl cinnamate.svg
Benzyl cinnamate 3D spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceWhite to pale yellow solid [1]
Melting point 34–37 °C (93–99 °F; 307–310 K) [2]
Boiling point 195–200 °C (383–392 °F; 468–473 K) 5 mmHg [2]
Insoluble [1]
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.

Contents

Natural occurrence

Balsam is the major producer of benzyl cinnamate. [3] It is used as an ingredient in the medicated cream product Sudocrem. [4]

Uses

It is used as a flavoring agent. [3]

It is used pharmaceutically as an antibacterial and antifungal. [5]

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. ↑ 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.
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