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
CAS Number
  • 103-41-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4437893
ECHA InfoCard 100.002.827 Edit this at Wikidata
PubChem CID
  • 5273469
UNII
  • V67O3RO97U checkY
CompTox Dashboard (EPA)
  • DTXSID00880905 DTXSID3041663, DTXSID00880905 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C16H14O2
Molar mass 238.286 g·mol−1
Appearance White 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]
Solubility in water
 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).
Infobox references
Chemical compound

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

Natural occurrence

Benzyl cinnamate occurs in Balsam of Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam.[3] It is used as an ingredient in the medicated cream product Sudocrem.[4]

Synthesis

Benzyl cinnamate can be prepared by heating benzyl chloride and excess sodium cinnamate in water to 100–115 °C or 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.[5] It is used as a flavoring agent.[3]

It is used pharmaceutically as an antibacterial and antifungal.[6]

References

  1. ^ a b "Specifications for Flavourings". Food and Agriculture Organization. Archived from the original on 2015-09-24. Retrieved 2014-02-20.
  2. ^ a b "Benzyl cinnamate". Sigma-Aldrich.
  3. ^ a b c 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. ^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59
  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.

External links