Benzyl benzoate

Benzyl benzoate
Names
Other names
Ascabin, Ascabiol, Ascarbin, Benzylate, Scabanca, Tenutex, Vanzoate, Venzoate, Benzoic acid phenylmethyl ester, Benzy alcohol benzoic ester
Identifiers
ATC code P03AX01
QP53AX11
120-51-4 Yes
ChEBI CHEBI:41237 Yes
ChEMBL ChEMBL1239 Yes
ChemSpider 13856959 Yes
DrugBank DB02775 Yes
Jmol-3D images Image
KEGG D01138 Yes
PubChem 2345
UNII N863NB338G Yes
Properties
Molecular formula
 C14H12O2
Molar mass 212.24 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)
insoluble
Solubility miscible in alcohol, chloroform, ether, oils
soluble in acetone, benzene
insoluble in glycerol
1.5681 (21 °C)
Hazards
EU classification 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
1
1
0
Flash point 158 °C (316 °F) (closed cup)
481 °C (898 °F; 754 K)
1700 mg/kg (rat, oral)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 Yes verify (what is: Yes/?)
Infobox references

Benzyl benzoate is the 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]

Uses

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]

Other uses of benzyl benzoate are dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.[1]

Side effects

Benzyl benzoate has low acute toxicity in laboratory animals. It is rapidly hydrolyzed to benzoic acid and benzyl alcohol, which are subsequently metabilized 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, incoordination, ataxia, convulsions, and respiratory paralysis.[4]

Benzyl benzoate is irritant to the skin.[5]

Production

Benzyl benzoate is produced industrially by the reaction of sodium benzoate with benzyl alcohol in the presence of a base. Alternatively, it is produced by transesterification of methylbenzoate and benzyl alcohol.[6] It is also a byproduct of benzoic acid synthesis by toluene oxidation.[1] It can also be generated by the Tishchenko reaction of benzaldehyde, using sodium benzylate and aluminium benzylate as catalysts:[7]

2 PhCHO → PhCH2O2CPh

References

  1. ↑ 1.0 1.1 1.2 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. ↑ 4.0 4.1 Jamaluddin Shaikh (2005), "Benzyl Benzoate", in Philip Wexler, Encyclopedia of Toxicology 1 (2nd ed.), Elsevier, pp. 264–265
  5. ↑ 5.0 5.1 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. ↑ 6.0 6.1 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