Enzymatic synthesis of short chain citronellyl esters by a new lipase from Rhizopus sp

Abstract

Short chain citronellyl esters were synthesized by a new microbial lipase from Rhizopus sp strain isolated and lipase produced at UNICAMP, Brazil. Direct esterification and transesterification reactions have been performed to produce citronellyl acetate and butyrate in a free-solvent system and with n-hexane in reaction medium. Reaction mixture for direct esterification and transesterification was carried out at 45ºC in equimolar concentration of substrates: acid or ester and alcohol. Only citronellyl butyrate was synthesized by direct esterification with yields from 95 to 100% after 24 hrs. of reaction time, with or without n-hexane. Citronellyl acetate was synthesized by transesterification with ethyl acetate and cytronellol, with yield of 58% after 48 hrs. and 48% of conversion for reaction butyl acetate and cytronellol. The results suggest that the size of the aliphatic chain from acyl donor was importance to conversion rate. Acids with more than two carbons showed to be better substrate for Rhizopus sp lipase. Transesterification reaction showed different behaviour, ester substrate with four carbons was better than six carbon for citronellyl acetate synthesis.

Lipase and their different industrial applications: A review

“…Lipases are the most pliant biocatalyst and convey broad series of biotransformation reactions, i.e., hydrolysis, esterification, interesterification, aminolysis, alcoholysis and acidolysis (Kumar and Gupta, 2008).…”

“…micro organism the main producers of lipase are Pencillium sp. (Gupta et al, 2003), Rhizopus sp. (Marlot et al, 1985), Aspergillus sp.…”

“…Candida rugosa is one of the most rapidly used industrially important enzymes due to its high activity in both hydrolysis as well as synthesis phase (Ramos-Sanchez et al, 2015) . In 1985, Candida rugosa is used by Japan for the production of fatty acids from castor bean (Macedo et al, 2003). Earlier it has been reported for use of microbial lipase in the flavoring of milk and creams production (Padilha et al, 2012).…”

“…In enzymological remediation, the lipase strains play important role in soil pollution (Lasoń and Ogonowski, 2010). Lipase shows unique properties in field of cold adaption like active compounds synthesis cold condition, bioremediation in fat contaminated and wastewater treatment in cold condition (Bhargav et al, 2008).…”

Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation

“…Although numerous hydrolases are produced by SSF, only a few reports have discussed their application in biotransformation. Macedo et al [18] described the production of lipases by SSF and preparation of lyophilized powder of extracted enzymes used for synthesis of short chain citronellyl esters. Only one study, conducted by Nagy et al [19], has examined lipases produced by SSF as catalysts for kinetic resolution of racemic secondary alcohols.…”