Benzyl benzoate

Benzyl benzoate
Benzyl benzoate
Identifiers
CAS number 120-51-4 YesY
PubChem 2345
ChemSpider 13856959 YesY
UNII N863NB338G YesY
DrugBank DB02775
KEGG D01138 YesY
ChEBI CHEBI:41237 YesY
ChEMBL CHEMBL1239 YesY
ATC code P03AX01,QP53AX11
Jmol-3D images Image 1
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)
 YesY benzoate (verify) (what is: YesY/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.

Contents

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]

Tishchenko reaction.gif

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:

List of plants that contain the chemical

  • Kaempferia rotunda [5][6]
  • Zingiber cassumunar [6]

Compendial status

References

  1. ^ Kamm, O.; Kamm, W. F. (1941), "Benzyl benzoate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0104 ; Coll. Vol. 1: 104 
  2. ^ "Benzyl Benzoate". Patient UK. 2005-02-10. http://www.patient.co.uk/showdoc/30002528/. 
  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. (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)". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 3 July 2009. 

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Look at other dictionaries:

  • benzyl benzoate — n a colorless oily ester C14H12O2 used in medicine formerly as an antispasmodic and now in the form of a lotion as a scabicide and in perfumery as a fixative and solvent * * * an oily aromatic liquid that is applied to the body in the form of a… …   Medical dictionary

  • benzyl benzoate — noun : a colorless oily ester C6H5COOCH2C6H5 occurring especially in balsams (as balsam of Peru), made synthetically, and used chiefly in medicine as an antispasmodic and in the form of a lotion as a scabicide and in perfumery as a fixative and… …   Useful english dictionary

  • benzyl benzoate lotion — [USP] a preparation of benzyl benzoate, triethanolamine, oleic acid, and purified water; used as a topical scabicide …   Medical dictionary

  • benzyl benzoate — Chem., Pharm. a colorless, faintly aromatic liquid, C14H12O2, used chiefly as a fixative and solvent in the manufacture of flavorings and perfume and in medicine in the treatment of certain skin conditions. [1915 20] * * * …   Universalium

  • benzyl benzoate — an oily aromatic liquid that is applied to the body – in the form of an emulsion – for the treatment of scabies. It causes skin irritation and should not be used to treat children. Trade names: Ascabiol …   The new mediacal dictionary

  • Benzoate de denatonium — Benzoate de dénatonium Benzoate de dénatonium Général Nom IUPAC phenylmethyl [2 [(2,6 dimethylphenyl)amino] 2 oxoethyl] diethylammonium benzoate …   Wikipédia en Français

  • Benzoate de dénatonium — Général Nom IUPAC phenylmethyl [2 [(2,6 dimethylphenyl)amino] 2 oxoethyl] diethylammonium benzoate …   Wikipédia en Français

  • benzyl — The hydrocarbon radical, C6H5CH2 . b. alcohol C6H5CH2OH; possesses local anesthetic and bacteriostatic properties. SYN: phenmethylol, phenylcarbinol. b. benzoate an agent that reduces th …   Medical dictionary

  • Sodium benzoate — Sodium benzoate …   Wikipedia

  • Potassium benzoate — Chembox new ImageFile=Potassium benzoate.png ImageSize=200px IUPACName=Potassium benzoate OtherNames=Benzoic acid, potassium salt Section1= Chembox Identifiers CASNo=582 25 2 PubChem=11399 EINECS = 209 481 3 SMILES=C1=CC=C(C=C1)C(=O) [O ] . [K+]… …   Wikipedia

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