Chemical Properties
Benzyl acetoacetate is a yellow, viscous liquid with a sweet, floral, fresh, balsamic, fruity odor similar to that of ethyl acetate.
Occurrence
Reported found in litchi (Litchi sinensis Sonn.).
Uses
Benzyl acetoacetate (AAbenzyl) is chemical intermediate used for the syntheses of different organic chemicals Product Data Sheet
Uses
Benzyl acetoacetate is used as a Pharmaceutical and fine chemical intermediate. Occasionally used in perfumery for special notes. Blends very well with refined Labdanum extracts, iso-Butyl cinnamate, Ionones, etc. and lends a natural, mellow topnote to woodyfloral or herbaceous-floral fragrances. Although relatively high boiling, it appears in a fragrance at the very initial notes with surprising tenacity. Also used in flavor compositions, mainly in Berry and Fruit flavors in concentrations equal to 50 ppm in the functional consumer product.
Definition
ChEBI: Benzyl acetoacetate is a carboxylic ester. It is functionally related to a benzyl alcohol.
Preparation
By heating ethyl acetoacetate and benzyl alcohol to 160°C.
General Description
Benzyl acetoacetate undergoes asymmetric bioreduction to form benzyl (
S)-(+)-3-hydroxybutyrate in the presence of
Candida schatavii strain MY 1831.
Purification Methods
Fractionate the ester and collect fractions with the expected physical properties. Otherwise add ca 10% by weight of benzyl alcohol and heat in an oil bath (160-170o, open vessel) for 30minutes during which time excess of benzyl alcohol will have distilled off, then fractionate. [Baker et al. J Org Chem 17 77 1952, Beilstein 6 IV 2480.]
