Benzyl cinnamate

Benzyl cinnamate
Names
	IUPAC name Benzyl 3-phenylprop-2-enoate
	Other names Benzylcinnamate; Cinnamein; Benzylcinnamoate; 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;
	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	238.29 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

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]

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.^[4] It is used as a flavoring agent.^[3]

References

1 2 "Specifications for Flavourings". Food and Agricultural Organization.
1 2 "Benzyl cinnamate". Sigma-Aldrich.
1 2 3 George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, pp. 147–148
↑ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59

External links

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

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[FAO-1] 1 2 "Specifications for Flavourings". Food and Agricultural Organization.

[Aldrich-2] 1 2 "Benzyl cinnamate". Sigma-Aldrich.

[fen-3] 1 2 3 George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, pp. 147–148

[ull-4] Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59