TY - JOUR
T1 - Thiyl radical-catalyzed isomerization of oils
T2 - An entry to the trans lipid library
AU - Samadi, Abdelouahid
AU - Andreu, Inmaculada
AU - Ferreri, Carla
AU - Dellonte, Sergio
AU - Chatgilialoglu, Chryssostomos
N1 - Funding Information:
This work was supported in part by the European Community’s Human Potential Program under contract HPRN-CT-2002-00184 [SULFRAD] and HPMF-CT-2001-01313 (Marie Curie individual fellowship to A.S.).
PY - 2004/8
Y1 - 2004/8
N2 - The unsaturated fatty acyl moieties of TAG present in natural oils of borage, olive, and rice were converted to their corresponding geometrical trans isomers by thiyl radical-catalyzed isomerization. Thiyl radicals were generated from 2-mercaptoethanol under photolytic or thermal conditions. A relevant feature of this method is the absence of double-bond shifts, so that no positional trans isomers or conjugated polyenes are formed. Oils obtained after the isomerization were winterized to further increase their trans fatty acid content. Methanolysis and hydrolysis of the trans oil mixtures using an enzymatic method (lipase B from Candida antarctica) gave good conversions to the corresponding trans FAME and fatty acids, respectively. These results are relevant for the studies of lipid isomerism and trans fatty acid recognition, which is a growing concern in biochemistry and nutrition, and open new perspectives for the synthesis of glycerides and studies of their structure-activity relationships.
AB - The unsaturated fatty acyl moieties of TAG present in natural oils of borage, olive, and rice were converted to their corresponding geometrical trans isomers by thiyl radical-catalyzed isomerization. Thiyl radicals were generated from 2-mercaptoethanol under photolytic or thermal conditions. A relevant feature of this method is the absence of double-bond shifts, so that no positional trans isomers or conjugated polyenes are formed. Oils obtained after the isomerization were winterized to further increase their trans fatty acid content. Methanolysis and hydrolysis of the trans oil mixtures using an enzymatic method (lipase B from Candida antarctica) gave good conversions to the corresponding trans FAME and fatty acids, respectively. These results are relevant for the studies of lipid isomerism and trans fatty acid recognition, which is a growing concern in biochemistry and nutrition, and open new perspectives for the synthesis of glycerides and studies of their structure-activity relationships.
KW - Geometrical isomerization
KW - Lipase
KW - Thiyl radicals
KW - Trans fatty acids
KW - Trans oils
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U2 - 10.1007/s11746-004-0974-8
DO - 10.1007/s11746-004-0974-8
M3 - Article
AN - SCOPUS:5444251197
SN - 0003-021X
VL - 81
SP - 753
EP - 758
JO - JAOCS, Journal of the American Oil Chemists' Society
JF - JAOCS, Journal of the American Oil Chemists' Society
IS - 8
ER -