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

Skouridou, V; Stamatis, H; Kolisis, FN

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	https://dspace.lib.ntua.gr/xmlui/handle/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