16491-36-4Relevant articles and documents
Synthesis of (Z)-3-hexen-1-yl butyrate in hexane and solvent-free medium using Mucor miehei and Candida antarctica lipases
Bourg-Garros,Razafindramboa,Pavia
, p. 1471 - 1475 (1997)
(Z)-3-Hexen-1 -yl butyrate is an important flavor and fragrance compound as it represents the model of a natural herbaceous (green) note. Two immobilized lipases from Mucor miehei (Lipozym IM) and from Candida antarctica (Novozym 435) were investigated for their use in the synthesis of (Z)-3-hexen-1-yl butyrate by direct esterification in n-hexane. To determine optimal conditions for esterification, we examined the following parameters: temperature, amount of lipase, acid/alcohol ratio, and absence of solvent. In n-hexane, bioconversion yields reached 95 (after 4 h) and 92% (after 6 h) for, respectively, Lipozym IM [17 (w/w reactants)] and Novozym 435 [2% (w/w reactants)]. In the absence of solvent, at 60 °C, Novozym 435-catalyzed esterification afforded the title compound in 80% yield. Up to 250 g (in hexane) and 160 g (without solvent) of ester were easily prepared, in a single operation, at a laboratory scale, in few hours, using 2% (w/w reactants) lipase.
Rapeseed lipase catalyzed synthesis of butyl butyrate for flavour and nutraceutical applications in organic media
Liaquat, Muhammad
experimental part, p. 6 - 13 (2012/06/18)
Butyl butyrate, a short chain ester with fine fruity pineapple odour, is a significant flavour compound. Recent investigations show that butyrate esters also have anticancer activity. Factors influencing the synthesis of butyl butyrate by organic phase biocatalysis were investigated. Maximum ester yield of 89% was obtained when 0.25 M butanol and butyric acid were reacted at 25 °C for 48 h in the presence of 250 mg rape seed lipase acetone powder in hexane. Addition of water did not affect synthesis, while a water activity of 0.45 was found optimum. Of 15 different alcohols evaluated, isoamyl and (Z)-3- hexen-1-ol were esterified most effectively with molar conversion yields of 92.2 and 80.2%. Short chain primary alcohols such as methanol and medium-long chain alcohols, such as heptanol and octanol were esterified more slowly. The results show that rape seed lipase is versatile catalyst for ester synthesis with temperature stability range 5-50 °C.
