Benzyl benzoate

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Benzyl benzoate
Benzyl benzoate structure.svg
Benzyl benzoate ball-and-stick.png
Identifiers
CAS number 120-51-4 YesY
PubChem 2345
ChemSpider 13856959 YesY
UNII N863NB338G YesY
DrugBank DB02775
KEGG D01138 YesY
ChEBI CHEBI:41237 YesY
ChEMBL CHEMBL1239 YesY
ATC code P03AX01,QP53AX11
Jmol-3D images Image 1
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)
Solubility in water insoluble
Solubility miscible in alcohol, chloroform, ether, oils
soluble in acetone, benzene
insoluble in glycerol
Refractive index (nD) 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
Flash point 158 °C (316 °F) (closed cup)
LD50 1700 mg/kg (rat, oral)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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[edit]

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[edit]

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[edit]

  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". 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