19670-51-0Relevant articles and documents
Crystallization, polymorphism, and binary phase behavior of model enantiopure and racemic triacylglycerols
Craven, R. John,Lencki, Robert W.
, p. 1723 - 1732 (2011)
Triacylglycerols (TAG) are the main component in fats and oils and a major component in many food and consumer products. These compounds are always asymmetric (about the sn-2 position), while many diacid and all triacid TAG are chiral. To understand what effect this has on their crystallization behavior, model enantiopure (1,2-bisdecanoyl-3-palmitoyl-sn-glycerol) and racemic (bisdecanoyl-1(3)-palmitoyl-rac-glycerol) TAG were prepared and characterized. In addition, a binary phase diagram was prepared to investigate their phase behavior and the racemate's crystalline tendency. For the subject compounds, infrared spectroscopy and X-ray powder diffraction data indicate the enantiopure TAG is β′-stable, whereas the racemic mixture is β-stable. In addition, based on the phase diagram, the high-melting form of the racemic mixture is a racemic compound (with a unit cell containing equal quantities of both enantiomers). Racemic (and nearracemic) mixtures also crystallize in a lower-melting metastable conglomerate β′ form. Thus, there are critical differences between the crystallization behavior of enantiopure and racemic TAG, and future investigations of these compounds should reflect these findings.
A new approach to the synthesis of lysophosphatidylcholines and related derivatives
Bibak, Niloufar,Hajdu, Joseph
, p. 5875 - 5877 (2003)
A new stereospecific synthesis of lysophosphatidylcholines is reported. The sequence relies on orthogonal protection of hydroxyl groups derived from glyceric acid, using fluorenylmethylcarbonate versus tetrahydropyranyl ether functions, that allow regiospecific introduction of substituents to obtain the target phospholipid compound.
Synthesis of enantiopure ABC-type triacylglycerols
Gudmundsson, Haraldur G.,Linderborg, Kaisa M.,Kallio, Heikki,Yang, Baoru,Haraldsson, Gudmundur G.
, (2019/12/26)
The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step chemoenzymatic route involving a highly regioselective immobilised Candida antarctica lipase. The second group was prepared by a similar six-step approach, that required two separate lipase steps. Such enantiopure TAGs are strongly demanded as standards for enantiospecific analysis of intact TAGs in fats and oils.
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.
