Benzyl benzoate

Benzyl benzoate
Names
	Other names Ascabin, Ascabiol, Ascarbin, Benzylate, Scabanca, Tenutex, Vanzoate, Venzoate, Benzoic acid phenylmethyl ester, Benzy alcohol benzoic ester
Identifiers
CAS Number	120-51-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:41237 ;
ChEMBL	ChEMBL1239 ;
ChemSpider	13856959 ;
DrugBank	DB02775 ;
ECHA InfoCard	100.004.003
KEGG	D01138 ;
PubChem CID	2345;
UNII	N863NB338G ;
CompTox Dashboard (EPA)	DTXSID8029153 ;
	InChI InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2 Key: SESFRYSPDFLNCH-UHFFFAOYSA-N ; InChI=1/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2 Key: SESFRYSPDFLNCH-UHFFFAOYAD;
	SMILES O=C(OCc1ccccc1)c2ccccc2;
Properties
Chemical formula	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)
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
NFPA 704 (fire diamond)	1 1 0
Flash point	158 °C (316 °F) (closed cup)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) 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

^ ^a ^b ^c Takao Maki; et al. (2007), "Benzoic Acid and Derivatives", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6 {{citation}}: Explicit use of et al. in: |author= (help)
^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59 {{citation}}: Explicit use of et al. in: |author= (help)
^ "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 {{citation}}: Explicit use of et al. in: |editor= (help)
^ ^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

[benz-1] Takao Maki; et al. (2007), "Benzoic Acid and Derivatives", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6 {{citation}}: Explicit use of et al. in: |author= (help)

[frag-2] Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59 {{citation}}: Explicit use of et al. in: |author= (help)

[3] "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[tox-4] Jamaluddin Shaikh (2005), "Benzyl Benzoate", in Philip Wexler (ed.), Encyclopedia of Toxicology, vol. 1 (2nd ed.), Elsevier, pp. 264–265

[rook-5] 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 {{citation}}: Explicit use of et al. in: |editor= (help)

[benzalc-6] Friedrich Brühne, Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 7

[benzald-7] Friedrich Brühne, Elaine Wright (2007), "Benzaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 3

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