Benzyl cinnamate

Benzyl cinnamate
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 ;
3D model (JSmol)	Interactive image;
ChemSpider	4437893;
ECHA InfoCard	100.002.827
PubChem CID	5273469;
UNII	V67O3RO97U ;
CompTox Dashboard (EPA)	DTXSID00880905 DTXSID3041663, DTXSID00880905 ;
	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;
	SMILES 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
Melting point	34–37 °C (93–99 °F; 307–310 K)
Boiling point	195–200 °C (383–392 °F; 468–473 K) 5 mmHg
Solubility in water	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). Infobox references

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

Natural occurrence[edit]

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[edit]

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[edit]

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[edit]

^ ^a ^b "Specifications for Flavourings". Food and Agriculture Organization. Archived from the original on 2015-09-24. Retrieved 2014-02-20.
^ ^a ^b "Benzyl cinnamate". Sigma-Aldrich.
^ ^a ^b ^c George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, pp. 147–148
^ "Sudocrem Antiseptic Healing Cream - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 11 June 2021.
^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59
^ 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[edit]

Benzyl cinnamate at National Library of Medicine's Toxicology Data Network

[FAO-1] "Specifications for Flavourings". Food and Agriculture Organization. Archived from the original on 2015-09-24. Retrieved 2014-02-20.

[Aldrich-2] "Benzyl cinnamate". Sigma-Aldrich.

[fen-3] 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.

[ull-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.

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