Benzyl benzoate
| Benzyl benzoate | |
|---|---|
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| Other names Ascabin, Ascabiol, Ascarbin, Benzylate, Scabanca, Tenutex, Vanzoate, Venzoate, Benzoic acid phenylmethyl ester, Benzy alcohol benzoic ester | |
| Identifiers | |
| CAS number | 120-51-4  |
| PubChem | 2345 |
| ChemSpider | 13856959 |
| UNII | N863NB338G |
| DrugBank | DB02775 |
| KEGG | D01138 |
| ChEBI | CHEBI:41237 |
| ChEMBL | CHEMBL1239 |
| ATC code | P03,QP53AX11 |
| Jmol-3D images | Image 1 |
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| 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 | |
| MSDS | Oxford MSDS |
| EU classification | Harmful (Xn) |
| NFPA 704 |
 1
1
0
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| Flash point | 158 °C (316 °F) (closed cup) |
| Autoignition temperature | 481 °C; 898 °F; 754 K |
| LD50 | 1700 mg/kg (rat, oral) |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Benzyl benzoate 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 Peru balsam and Tolu balsam.[1][2]
Uses
Benzyl benzoate is used as an acaricide, scabicide, and pediculicide in veterinary hospitals. It is also a repellent for chiggers, ticks, and mosquitoes.[3] It is an effective and inexpensive topical treatment for human scabies.[4] It has vasodilating and spasmolytic effects and is present in many asthma and whooping cough drugs.[5]
Other uses of benzyl benzoate are dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.[1]
Production
Benzyl benzoate is produced by esterifying dry sodium benzoate with benzyl chloride or by the dimerization of benzaldehyde. It is also a byproduct of benzoic acid synthesis by toluene oxidation.[1] It can also be generated by the Tishchenko reaction of benzaldehyde, with sodium benzylate and aluminum benzylate as catalysts:[6]
Toxicity
Benzyl benzoate has low acute toxicity in laboratory animals. It is rapidly hydrolyzed to benzoic acid and benzyl alcohol, which is subsequently hydrolyzed 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.[3]
Benzyl benzoate is irritant to the skin.[4]
References
- ↑ 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
- ↑ Karl-Georg Fahlbusch et al. (2007), "Flavors and Fragrances", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59
- ↑ 3.0 3.1 Jamaluddin Shaikh (2005), "Benzyl Benzoate", in Philip Wexler, Encyclopedia of Toxicology 1 (2nd ed.), Elsevier, pp. 264–265
- ↑ 4.0 4.1 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
- ↑ Friedrich Brühne, Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 7
- ↑ Friedrich Brühne, Elaine Wright (2007), "Benzaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 3
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