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

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

^ ^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

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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