Benzyl benzoate
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| Names | |
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| Other names
Ascabin, Ascabiol, Ascarbin, Benzylate, Scabanca, Tenutex, Vanzoate, Venzoate, Benzoic acid phenylmethyl ester, Benzy alcohol benzoic ester
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | BnBzO |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.004.003 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H12O2 | |
| Molar mass | 212.248 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 |
Refractive index (nD)
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1.5681 (21 °C) |
| Pharmacology | |
| P03AX01 (WHO) QP53AX11 (WHO) | |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 158 °C (316 °F) (closed cup) |
| 481 °C (898 °F; 754 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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).
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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]
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]
Benzyl benzoate is also used as a 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 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 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, or by transesterification of methylbenzoate 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 and aluminium benzylate as catalysts:[7]
- 2 PhCHO → PhCH2O2CPh
References
- ^ a b c 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
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ a b Jamaluddin Shaikh (2005), "Benzyl Benzoate", in Philip Wexler (ed.), Encyclopedia of Toxicology, vol. 1 (2nd ed.), Elsevier, pp. 264–265
- ^ a b D.A. Burns (2010), "Diseases Caused by Arthropods and Other Noxious Animals", in Tony Burns; et al. (eds.), Rook's Textbook of Dermatology, vol. 2 (8th ed.), Wiley-Blackwell, p. 38.41
- ^ a b 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