106689-24-1Relevant articles and documents
Effects of chain length and sulphur position of thia fatty acids on their incorporation into phospholipids in 7800 C1 hepatoma cells and isolated rat hepatocytes, and their effects on fatty acid composition of phospholipids
Wu, Pengfei,Grav, Hans J.,Horn, Robert,Bremer, Jon
, p. 751 - 758 (1996)
Incorporation of thia fatty acids and their effects on the fatty acid composition in phospholipids has been investigated in 7800 C1 hepatoma cells and cultured hepatocytes. 3-Thia fatty acids of chain lengths from dodecyl-to hexadecyl-thioacetic acid were incorporated into phospholipids during a 3-day incubation. Longer and shorter 3-thia fatty acids were barely detectable. Tetradecylthioacetic acid, 3-thia stearate, and their Δ9-desaturated derivatives were maximally incorporated into whole-cell phospholipids. The amount of tetradecylthioacetic acid incorporated into phospholipids of hepatoma cells remained almost identical in cells cultured for 3 days or adapted over a period of 1 year. Δ9-desaturated metabolites of long chain thia fatty acids (C13-to C16-S-acetic acid) were identified by GC-MS in phospholipids. 3-Thia stearate appeared to be the best substrate for Δ9 desaturase. Incubation of hepatoma cells with thia fatty acids led to alterations in the amount of normal fatty acids in total phospholipids. The amounts of 16:0 and 18:1 decreased and 18:2(n-6) and 20:5 (n-3) increased. Changes in the normal fatty acid composition of phospholipids were seen both with thia acids incorporated into phospholipids and those not incorporated. These effects, therefore, may be only partially dependent on displacement of normal fatty acids by thia fatty acids. Morris 7800 C1 hepatoma cell acyl-CoA synthetase (ACS) and peroxisomal acyl-CoA oxidase (AGO) were induced by thia fatty acids of all chain lengths, and with the sulphur atom(s) in different positions. Control experiments with hepatocytes revealed a similar incorporation of thia fatty acids in these physiologically more normal cells.
1H and 13C N.M.R. Studies on the Positional Isomers of Methyl Thialaurate and Methyl Thiastearate
Jie, Marcel S. F. Lie Ken,Bakare, Oladapo
, p. 2121 - 2126 (2007/10/02)
1H N.m.r. analysis of methyl thialaurate and methyl thiastearate shows that the sulphur atom in the alkyl chain has a significant deshilding effect (α-effect) on the chemical shift of the protons of the adjacent methylene and methyl groups, and also on the methyl protons of the methoxycarbonyl (ester) function.It was possible to identify seven of the positional isomers in each series by examining the chemical shifts and the splitting pattern of the signals in the 1H n.m.r. spectra of these fatty acid ester analogues.The 13C n.m.r. results showed that this S atom has an interesting effect (α-, β-, and γ-effect) on the chemical shift of the carbonyl carbon atom of the methoxycarbonyl (ester) function: the sulphur atom exerts a significant shilding effect in the case of the 2-, 3-, and 4-thia isomers.In the remaining isomers the sulphur atom causes a strong deshilding effect on the methylene or methyl carbon atoms on either side of the sulphide linkage.These results permitted all positional isomers of methyl thialaurate to be identified by this technique, while 10 out of the 16 positional isomers of methyl thiastearate could be characterized.
