Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase

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dc.contributor.author Skouridou, V en
dc.contributor.author Stamatis, H en
dc.contributor.author Kolisis, FN en
dc.date.accessioned 2014-03-01T01:19:40Z
dc.date.available 2014-03-01T01:19:40Z
dc.date.issued 2003 en
dc.identifier.issn 1438-7697 en
dc.identifier.uri http://hdl.handle.net/123456789/15655
dc.subject Candida antarctica lipase en
dc.subject Enantioselectivity en
dc.subject Esterification en
dc.subject Monoterpenes en
dc.subject Perillyl alcohol en
dc.subject.classification Food Science & Technology en
dc.subject.classification Nutrition & Dietetics en
dc.subject.other decanoic acid en
dc.subject.other essential oil en
dc.subject.other fatty acid en
dc.subject.other myrcene en
dc.subject.other organic solvent en
dc.subject.other palmitic acid en
dc.subject.other perillyl alcohol en
dc.subject.other pinene en
dc.subject.other propionic acid en
dc.subject.other terpene derivative en
dc.subject.other triacylglycerol lipase en
dc.subject.other article en
dc.subject.other catalysis en
dc.subject.other enantiomer en
dc.subject.other enantioselectivity en
dc.subject.other esterification en
dc.subject.other hydrophobicity en
dc.subject.other Candida antarctica en
dc.title Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase en
heal.type journalArticle en
heal.identifier.primary 10.1002/ejlt.200390026 en
heal.identifier.secondary http://dx.doi.org/10.1002/ejlt.200390026 en
heal.language English en
heal.publicationDate 2003 en
heal.abstract The synthesis of perillyl alcohol esters by direct esterification catalyzed by immobilized lipase from Candida antarctica (Novozyme 435) was studied. For this purpose, fatty acids with a chain length from 3-16 were used. The reactions were carried out in mixtures of alpha-pinene and myrcene as well as in pure organic solvents. It was found that the esterification rates increased from 3.7-6.9 mM/min when using decreasing concentrations of myrcene in a-pinene (100-0%). Higher rates and conversions were obtained with decanoic acid as the acyl donor (6.9 mM/min, 81.5%), while lower conversions were obtained with fatty acids of shorter (propionic acid, 5.6%) or longer (hexadecanoic acid, 62.5%) carbon chain. In addition, it was found that the effect of the water activity depended on the chain length of the acyl donor and the composition of the solvent mixture. Also, esterification rates increased from 1.8-6.9 mM/min with increasing hydrophobicity of the solvent (logP from 0.9-4.8) of the organic solvent used. Finally, it was found that Candida antarctica lipase presented a preference in the esterification of (S)-(-)- and (R)-(+)-perillyl alcohol in favor of the (R)-(+) enantiomer. The enantioselectivity was found increased with increasing logP, whereas the water activity of the reaction mixture did not affect the enantioselectivity significantly. en
heal.publisher WILEY-V C H VERLAG GMBH en
heal.journalName European Journal of Lipid Science and Technology en
dc.identifier.doi 10.1002/ejlt.200390026 en
dc.identifier.isi ISI:000182506700002 en
dc.identifier.volume 105 en
dc.identifier.issue 3-4 en
dc.identifier.spage 115 en
dc.identifier.epage 120 en

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