Benzyl benzoate

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Benzyl benzoate
Identifiers
CAS number120-51-4 YesY
PubChem2345
ChemSpider13856959 YesY
UNIIN863NB338G YesY
DrugBankDB02775
KEGGD01138 YesY
ChEBICHEBI:41237 YesY
ChEMBLCHEMBL1239 YesY
ATC codeP03AX01,QP53AX11
Jmol-3D imagesImage 1
Properties
Molecular formulaC14H12O2
Molar mass212.24 g mol−1
AppearanceColorless liquid
Odorfaint aromatic
Density1.118 g/cm3
Melting point18 °C; 64 °F; 291 K
Boiling point323 °C; 613 °F; 596 K
Solubility in waterinsoluble
Solubilitymiscible in alcohol, chloroform, ether, oils
soluble in acetone, benzene
insoluble in glycerol
Refractive index (nD)1.5681 (21 °C)
Hazards
MSDSOxford MSDS
EU classificationHarmful (Xn)
NFPA 704
NFPA 704.svg
1
1
0
Flash point158 °C (316 °F) (closed cup)
Autoignition temperature481 °C; 898 °F; 754 K
LD501700 mg/kg (rat, oral)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)
Infobox references
 
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Benzyl benzoate
Identifiers
CAS number120-51-4 YesY
PubChem2345
ChemSpider13856959 YesY
UNIIN863NB338G YesY
DrugBankDB02775
KEGGD01138 YesY
ChEBICHEBI:41237 YesY
ChEMBLCHEMBL1239 YesY
ATC codeP03AX01,QP53AX11
Jmol-3D imagesImage 1
Properties
Molecular formulaC14H12O2
Molar mass212.24 g mol−1
AppearanceColorless liquid
Odorfaint aromatic
Density1.118 g/cm3
Melting point18 °C; 64 °F; 291 K
Boiling point323 °C; 613 °F; 596 K
Solubility in waterinsoluble
Solubilitymiscible in alcohol, chloroform, ether, oils
soluble in acetone, benzene
insoluble in glycerol
Refractive index (nD)1.5681 (21 °C)
Hazards
MSDSOxford MSDS
EU classificationHarmful (Xn)
NFPA 704
NFPA 704.svg
1
1
0
Flash point158 °C (316 °F) (closed cup)
Autoignition temperature481 °C; 898 °F; 754 K
LD501700 mg/kg (rat, oral)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)
Infobox references

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

Synthesis[edit]

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]

Tishchenko reaction.gif

Uses[edit]

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:

List of plants that contain the chemical[edit]

Compendial status[edit]

References[edit]

  1. ^ Kamm, O.; Kamm, W. F. (1941), "Benzyl benzoate", Org. Synth. ; Coll. Vol. 1: 104 
  2. ^ "Benzyl Benzoate". Patient UK. 2005-02-10. 
  3. ^ 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. 
  4. ^ National Sweet Itch Centre
  5. ^ 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. 
  6. ^ a b Nugroho, Bambang W. et al.; Schwarz, Brunhilde; Wray, Victor; Proksch, Peter (1996). "Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda". Phytochemistry 41 (1): 129–132. doi:10.1016/0031-9422(95)00454-8. 
  7. ^ British Pharmacopoeia Commission Secretariat (2009). "Index (BP 2009)". Retrieved 3 July 2009.