Benzyl benzoate

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Benzyl benzoate
Benzyl benzoate structure.svg
Benzyl benzoate ball-and-stick.png
Preferred IUPAC name
Benzyl benzoate
Other names
Benzoic acid phenylmethyl ester
Benzy alcohol benzoic ester
120-51-4 YesY
Abbreviations BnBzO
ChEBI CHEBI:41237 YesY
ChemSpider 13856959 YesY
DrugBank DB02775 YesY
Jmol 3D model Interactive image
KEGG D01138 YesY
PubChem 2345
UNII N863NB338G YesY
Molar mass 212.25 g·mol−1
Appearance Colorless liquid
Odor faint aromatic
Density 1.118 g/cm3
Melting point 18 °C (64 °F; 291 K)
Boiling point 323 °C (613 °F; 596 K)
Solubility miscible in alcohol, chloroform, ether, oils
soluble in acetone, benzene
insoluble in glycerol
1.5681 (21 °C)
P03AX01 (WHO) QP53AX11 (WHO)
Harmful (Xn)
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 158 °C (316 °F) (closed cup)
481 °C (898 °F; 754 K)
Lethal dose or concentration (LD, LC):
1700 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Benzyl benzoate is an organic compound with the formula C6H5CH2O2CC6H5. It is the ester of benzyl alcohol and benzoic acid. It forms either a viscous liquid or solid flakes and has a weak, sweet-balsamic odor. It occurs in a number of blossoms (e. g. tuberose, hyacinth) and is a component of Balsam of Peru and Tolu balsam.[1][2]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[3]


Benzyl benzoate is used as an acaricide, scabicide, and pediculicide in veterinary hospitals. It is also a repellent for chiggers, ticks, and mosquitoes.[4] It is an effective and inexpensive topical treatment for human scabies.[5] It has vasodilating and spasmolytic effects and is present in many asthma and whooping cough drugs.[6]

Benzyl benzoate is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.[1]

Side effects[edit]

Benzyl benzoate has low acute toxicity in laboratory animals. It is rapidly hydrolyzed to benzoic acid and benzyl alcohol. Benzyl alcohol is subsequently metabolized to benzoic acid. The conjugates of benzoic acid are rapidly eliminated in urine. When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, loss of coordination, ataxia, convulsions, and respiratory paralysis.[4]

Benzyl benzoate is a skin irritant.[5]


Benzyl benzoate is produced industrially by the reaction of sodium benzoate with benzyl alcohol in the presence of a base, or by transesterification of methyl benzoate and benzyl alcohol.[6] It is a byproduct of benzoic acid synthesis by toluene oxidation.[1] It can also be synthesized by the Tishchenko reaction, using benzaldehyde with sodium benzylate (generated from sodium and benzyl alcohol) as catalyst:[7][8]

The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is generated in situ from sodium and benzyl alcohol


  1. ^ a b c Takao Maki; et al. (2007), "Benzoic Acid and Derivatives", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6 
  2. ^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59 
  3. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  4. ^ a b Jamaluddin Shaikh (2005), "Benzyl Benzoate", in Philip Wexler, Encyclopedia of Toxicology, 1 (2nd ed.), Elsevier, pp. 264–265 
  5. ^ a b D.A. Burns (2010), "Diseases Caused by Arthropods and Other Noxious Animals", in Tony Burns; et al., Rook's Textbook of Dermatology, 2 (8th ed.), Wiley-Blackwell, p. 38.41 
  6. ^ a b Friedrich Brühne, Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 7 
  7. ^ Friedrich Brühne, Elaine Wright (2007), "Benzaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 3 
  8. ^ Kamm, O.; Kamm, W. F. (1941). "Benzyl benzoate". Org. Synth.  ; Coll. Vol., 1, p. 104