- Enzymatic interesterification of triolein and tristearin: Chemical structure and differential scanning calorimetric analysis of the products
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The structural composition and thermal properties of the products of enzymatic interesterification of triolein and tristearin were investigated. The biocatalyst for the reaction was an immobilized Candida antarctica lipase, SP435. Enzyme load of 10% (w/w reactants) produced 72% of desired total products. Oleoyl-distearoyl triglycerides (SSO, OSS) had higher melting points than dioleoyl-stearoyl triglycerides (OOS, SOO) because the sample contained larger amounts of stearic acid than oleic acid residues. SOS and OSO were hardly produced (0.2 to 1.2%), which indicates that SP435 acted as a nonspecific lipase when catalyzing the interesterification of triolein and tristearin. The maximal yield of OSS and SSO (46.9%) was achieved with a 1:2 mole ratio of triolein to tristearin. As the proportion of tristearin was increased, the production of SOO and OOS decreased, the melting profile of the interesterified triglycerides shifted toward higher melting forms, and the solid fat content increased, indicating formation of hard fats.
- Seriburi, Vimon,Akoh, Casimir C.
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- Stereospecific synthesis of selected triglycerides: comments on acyl migration and analysis of configuration
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Symmetrical and stereospecifically defined triglycerides have been prepared from racemic and (R)- and (S)-glycidol, respectively.The synthetic sequence allows the incorporation of sensitive fatty acids such as linolenic acid.Justification for retention of
- Sonnet, Philip E.,Dudley, Robert L.
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- Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils
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Enantiomers of racemic triacylglycerol (TAG) mixtures were separated using two chiral HPLC columns with a sample recycling system and a UV detector. A closed system without sample derivatisation enabled separation and identification by using enantiopure reference compounds of eleven racemic TAGs with C12-C22 fatty acids with 0-2 double bonds. The prolonged separation time was compensated for byfewer pretreatment steps. Presence of one saturated and one unsaturated fatty acid in the asymmetricTAG favoured the separation. Enantiomeric resolution, at the same time with stronger retention of TAGs,increased with increasing fatty acid chain length in the sn-1(3) position. Triunsaturated TAGs containingoleic, linoleic or palmitoleic acids did not separate. The elution order of enantiomers was determined bychemoenzymatically synthesised enantiopure TAGs with a co-injection method. The method is applicableto many natural fats and oils of low unsaturation level assisting advanced investigation of lipid synthesisand metabolism.
- Kalpio, Marika,Nylund, Matts,Linderborg, Kaisa M.,Yang, Baoru,Kristinsson, Bj?rn,Haraldsson, Gudmundur G.,Kallio, Heikki
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p. 718 - 724
(2015/02/02)
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- Synthesis and physicochemical characterization of mixed diacid triglycerides that contain elaidic acid
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The synthesis of symmetrical and asymmetrical palmito- and stearo-elaidic triglycerides (PEP, SES, EPP, PEE, ESS, and SEE, in which P = palmitic, S = stearic, and E = elaidic acid) was undertaken to investigate their polymorphism. The chemical pathways and the purification steps, including crystallization and adsorption chromatography, are described. The different chromatographic analyses (gas-liquid chromatography: carbon number profile and fatty acid methyl ester profile, and high-performance liquid chromatography) revealed that the purity of the synthesized products was superior to 99% except for SES (>96%). The thermal behavior, as well as the polymorphism of these triglycerides, has been investigated by means of differential scanning calorimetry and powder X-ray diffraction spectroscopy at variable temperatures. The six compounds crystallize according to a double chainlength packing. The most stable polymorphic form of palmito-elaidic triglycerides belongs to the β′ variety, whereas the stearo-elaidic triglycerides are β stable.
- Elisabettini,Lognay,Desmedt,Culot,Istasse,Deffense,Durant
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p. 285 - 291
(2007/10/03)
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