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Benzyl benzoate


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

File: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]

It has other uses:

  • a fixative in fragrances to improve the stability and other characteristics of the main ingredients
  • a plasticizer in cellulose and other polymers
  • a solvent for various chemical reactions

List of plants that contain the chemical


Compendial status

  • British Pharmacopoeia 2009 [5]

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. {{cite journal
    | last = Woerdenbag
    | first = Herman J. et al.
    | authorlink =
    | coauthors =
    | title = Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia
    | journal = Flavour and Fragrance Journal
    | volume = 19
    | issue = 2
    | pages = 145–148
    | publisher =
    | location =
    | date = 2004
    | url =
    | issn =
    | doi = 10.1002/ffj.1284
    | id =
    | accessdate = 3 July 2009
    | last2 = Windono
    | first2 = Tri
    | last3 = Bos
    | first3 = Rein
    | last4 = Riswan
    | first4 = Sudarsono
    | last5 = Quax
    | first5 = Wim J.}}
  4. 4.0 4.1 {{cite journal
    | last = Nugroho
    | first = Bambang W. et al.
    | authorlink =
    | coauthors =
    | title = Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda
    | journal = Phytochemistry
    | volume = 41
    | issue = 1
    | pages = 129–132
    | publisher =
    | location =
    | date = 1996
    | url =
    | issn =
    | doi = 10.1016/0031-9422(95)00454-8
    | id =
    | accessdate = 3 July 2009}}
  5. {{cite web
    | last = British Pharmacopoeia Commission Secretariat
    | first =
    | authorlink =
    | coauthors =
    | title = Index (BP 2009)
    | work =
    | publisher =
    | date = 2009
    | url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
    | format =
    | doi =
    | accessdate = 3 July 2009
    }}


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