Benzyl benzoate

Benzyl benzoate

Identifiers
CAS number	120-51-4^Y
PubChem	2345
ChemSpider	13856959^Y
UNII	N863NB338G^Y
DrugBank	DB02775
KEGG	D01138^Y
ChEBI	CHEBI:41237^Y
ChEMBL	CHEMBL1239^Y
ATC code	P03AX01,QP53AX11
Jmol-3D images	Image 1
SMILES O=C(OCc1ccccc1)c2ccccc2
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^Y Key: SESFRYSPDFLNCH-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₄H₁₂O₂
Molar mass	212.24 g mol⁻¹
Appearance	Colorless liquid
Density	1.12 g/cm³
Melting point	18 °C, 291 K, 64 °F
Boiling point	323 °C, 596 K, 613 °F
Hazards
MSDS	Oxford MSDS
EU classification	Harmful (Xn)
Flash point	158 °C (316 °F) (closed cup)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C₆H₅CH₂O₂CC₆H₅. This easily prepared compound has a variety of uses.

1 Synthesis
2 Uses
3 List of plants that contain the chemical
4 Compendial status
5 References

Synthesis

This colorless liquid is formally the condensation product of benzoic acid and benzyl alcohol. It can also be generated from benzaldehyde by the Tishchenko reaction.^[1]

Uses

Benzyl benzoate, as a topical solution, may be used as an antiparasitic insecticide to kill the mites responsible for the skin condition scabies,^[2] for example as a combination drug of benzyl benzoate/disulfiram.^[3]

It has other uses:

a fixative in fragrances to improve the stability and other characteristics of the main ingredients
a food additive in artificial flavors
a plasticizer in cellulose and other polymers
a solvent for various chemical reactions
a treatment for sweet itch in horses^[4]
a treatment for scaly leg mites in chickens

List of plants that contain the chemical

Compendial status

British Pharmacopoeia 2009 ^[7]
Japanese Pharmacopoeia 15

References

^ Kamm, O.; Kamm, W. F. (1941), "Benzyl benzoate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0104 ; Coll. Vol. 1: 104
^ "Benzyl Benzoate". Patient UK. 2005-02-10. http://www.patient.co.uk/showdoc/30002528/.
^ Landegren J, Borglund E, Storgårds K (1979). "Treatment of scabies with disulfiram and benzyl benzoate emulsion: a controlled study". Acta Derm. Venereol. 59 (3): 274–6. PMID 87094.
^ National Sweet Itch Centre
^ Woerdenbag, Herman J. et al.; Windono, Tri; Bos, Rein; Riswan, Sudarsono; Quax, Wim J. (2004). "Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia". Flavour and Fragrance Journal 19 (2): 145–148. doi:10.1002/ffj.1284.
^ ^a ^b Nugroho, Bambang W. et al. (1996). "Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda". Phytochemistry 41 (1): 129–132. doi:10.1016/0031-9422(95)00454-8.
^ British Pharmacopoeia Commission Secretariat (2009). "Index (BP 2009)". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 3 July 2009.

Ectoparasiticides / arthropod (P03A)

Insecticide/pediculicide

Chlorine-containing products	Lindane

Chloride channel	Ivermectin

Organophosphate	Malathion

Acaricide/miticide/scabicide

Pyrethrines	Permethrin^# • Pyrethrum • Phenothrin

Chloride channel	Ivermectin

Sulfur-containing products	Disulfiram

Chlorine-containing products	Lindane

Benzoate	Benzyl benzoate^#

Organophosphate	Malathion

Other/ungrouped	Quassia • toluidine (Crotamiton)

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: IFT

helm,arth (acar)

helm, arth (lice), zoon

helm, arth