65390-75-2Relevant articles and documents
Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils
Kalpio, Marika,Nylund, Matts,Linderborg, Kaisa M.,Yang, Baoru,Kristinsson, Bj?rn,Haraldsson, Gudmundur G.,Kallio, Heikki
, p. 718 - 724 (2015/02/02)
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.
Synthesis of enantiopure structured triacylglycerols
Kristinsson, Bjoern,Linderborg, Kaisa M.,Kallio, Heikki,Haraldsson, Gudmundur G.
, p. 125 - 132 (2014/02/14)
The synthesis of nine enantiopure structured triacylglycerols (TAGs) of the AAB type is described, all possessing the (S)-absolute configuration. Six of them possess one saturated and two identical unsaturated fatty acyl chains, whereas the remaining three possess two identical saturated fatty acids along with one unsaturated fatty acid. The former group was synthesized by a five-step chemoenzymatic route involving a highly regioselective immobilized Candida antarctica lipase, starting from enantiopure (R)-solketal. The second group was prepared by a fully chemical five-step approach based on the same chiral precursor. Such enantiopure TAGs are strongly required as standards for the enantiospecific analysis of intact TAGs in fats and oils.
Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards
Lisa, Miroslav,Velinska, Hana,Holcapek, Michal
experimental part, p. 3903 - 3910 (2010/03/23)
Silver-ion normal-phase high-performance liquid chromatography (HPLC) provides a superior separation selectivity for lipids differing in the number and position of double bonds in fatty acid chains including the resolution of triacylglycerol (TG) regioiso
Atmospheric pressure covalent adduct chemical ionization tandem mass spectrometry for double bond localization in monoene- and diene-containing triacylglycerols
Xu, Yichuan,Brenna, J. Thomas
, p. 2525 - 2536 (2008/01/04)
We report a method to elucidate the structure of triacylglycerols (TAGs) containing monoene or diene fatty acyl groups by atmospheric pressure covalent adduct chemical ionization (APCACI) tandem mass spectrometry using acetonitrile as an adduct formation reagent. TAGs were synthesized with the structures ABB and BAB, where A is palmitate (C16:0) and B is an isomeric C18 monoene unsaturated at position 9, 11, or 13 or an isomeric diene unsaturated at positions 9 and 11, 10 and 12, or 9 and 12. In addition to the species at m/z 54 observed in previous CI studies of fatty acid methyl esters, we also found that ions at m/z 42, 81, and 95 undergo covalent reaction with TAGs containing double bonds to yield ions at m/z 40, 54, 81, and 95 units greater than that of the parent TAG: [M + 40]+, [M + 54]+, [M + 81] +, and [M + 95]+ ions. When collisionally dissociated, these ions fragment to produce two or three diagnostic ions that locate the double bonds in the TAG. In addition, ions [RCH=C=O + 40]+ and [RCH=C=O + 54]+ formed from collisional dissociation are of strong abundance in MS/ MS spectra, and collisional activation of these ions produces two intense confirmatory diagnostic ions in the MS3 spectra. Fragment ions reflecting neutral loss of an sn-1-acyl group from [M + 40]+ and [M + 54]+ are more abundant than those reflecting neutral loss of an sn-2-acyl group, analogous to previous reports for protonated TAGs. The position of each acyl group on the glycerol backbone is thus determined by the relative abundances of these ions. Under the conditions in our instrument, the [M + 40]+ adduct is at the highest signal and also yields all information about the double bond position and TAG stereochemistry. With the exception of geometries about the double bonds, racemic TAG isomers containing two monoenes or dienes and a saturate can be fully characterized by APCACI-MS/MS/MS.
Synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol from palm oil
Chen, Ming-Lung,Vali, Shaik Ramjan,Lin, Jih-Yao,Ju, Yi-Hsu
, p. 525 - 532 (2007/10/03)
Human milk fat contains 20-25% palmitic acid (16:0) and 30-35% oleic acid (18:1). More than 60% of the palmitic acid occurs at the sn-2 position of the glycerol backbone. Palm oil is a rich source of both palmitic and oleic acids. The structured lipid 1,3-dioleoyl-2-palmitoylglycerol (OPO) is an important ingredient in infant formula. OPO was synthesized from palm oil by a three-step method. In the first step, low-temperature fractionation was applied to palm oil FA, yielding a palmitic acid-rich fraction (87.8%) and an oleic acid-rich fraction (96%). The palmitic acid content was further increased to 98.3% by transforming palmitic acid into ethyl palmitate. In the second step, esterificalion of ethyl palmitate and glycerol catalyzed by lipase Novozym 435 under vacuum (40 mm Hg) was employed for the synthesis of tripalmitin. Finally, OPO was obtained by the reaction of tripalmitin with oleic acid catalyzed by Lipase IM 60. In this final step, the TAG content in the product acylglycerol mixture was 97%, and 66.1 % oleic acid was incorporated into TAG. Analysis of the FA composition at the sn-2 position of TAG showed 90.7 mol% of palmitic acid and 9.3 mol% of oleic acid. OPO content in the product TAG was ca. 74 mol%. Thus, an efficient method was developed for the synthesis of OPO from palm oil.
Synthesis of the racemic analog of a honeybee (Apis mellifera) breeding pheromone component
Yakovleva,Shayakhmetova,Gumerov,Ishmuratov
, p. 593 - 594 (2007/10/03)
The synthesis of 1-palmitoyl-2,3-dioleoylglycerine, the racemic analog of a honeybee breeding pheromone component, from 1,2-O-isopropylideneglycerine was proposed. 2004 Springer Science + Business Media, Inc.
Host-recognizing kairomones for parasitic wasp, Anisopteromalus calandrae, from larvae of azuki bean weevil, Callosobruchus chinensis.
Onodera, Junko,Matsuyama, Shigeru,Suzuki, Takahisa,Fujii, Koichi
, p. 1209 - 1220 (2007/10/03)
Host-recognizing kairomones for the stinging behavior of the parasitic wasp, Anisopteromalus calandrae, were identified on host azuki bean weevil larvae, Callosobruchus chinensis (L.). The kairomones were extracted with acetone from Chinese green beans, from which emerged wasps and host weevils had been removed. The kairomones are a mixture of triacylglycerols and fatty acids, each of which is separately active, and with no observable synergistic effect between them. These compounds are known to be constituents of an oviposition-marking pheromone of host azuki bean weevils. However, they differ from the previously reported saturated hydrocarbons and diacylglycerols of the kairomone that another parasitic wasp, Dinarmus basalis, uses for the host recognition of C. chinensis. Thus, A. calandrae and D. basalis selectively utilize different constituents of the oviposition-marking pheromone of C. chinensis as host-recognizing kairomones.
Synthesis and physicochemical characterization of mixed diacid triglycerides that contain elaidic acid
Elisabettini,Lognay,Desmedt,Culot,Istasse,Deffense,Durant
, p. 285 - 291 (2007/10/03)
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.
