Synthesis, NMR spectroscopic investigations and absolute quantification of dietary triacylglycerols

  • Fats and oils are important biological compounds. These are composed of fatty acids, phospholipids, cholesterol, sterols and triacylglycerols. Triacylglycerols (TAGs) are energy reservoirs for living organisms. TAGs are important components of lipid bilayer in the cells and cellular vesicles i.e., lipid droplets (LD). The most common fatty acids present in the plasma membrane are palmitic, stearic, linoleic, and linolenic acids. Proteins are attached to lipids in the plasma membrane and diffuse with a specific diffusion coefficient. The diffusion of the molecules across the membrane is described in terms of diffusion coefficients. The protein-lipid interactions play important role in the cell signaling and trafficking. The cell signaling and trafficking property of membrane lipids and proteins are important in the transport of drugs across the membrane. The fluidity of the membrane depends upon viscosity, chain length and degree of unsaturation of the unsaturated fatty acid chains. Several symmetrical and unsymmetrical TAGs have been synthesized in purity as a synthetic standard for the analytical studies. The synthesis of symmetrical triacylglycerols (TAGs) is done using previously reported Hassner esterification method. Following this method tripalmitin [PPP], tristearin [SSS], triolein [OOO], trilinolein [LLL], trioctanein [OcOcOc] and trilaurein [LaLaLa] have been synthesized in purity. The basic scheme of the reaction is the same as reported. However, the change in the reaction time, temperature and catalyst showed different yield of the product. The detailed scheme of reaction and experimental procedures have been explained. The unsymmetrical TAGs have been synthesized in two-step reaction following a reported method. Firstly, four 1-monoacylglycerols have been synthesized enantiomerically. These include 1-palmitoyl glycerol, 1-stereoyl glycerol, 1-oleoyl glycerol and 1-linoleoyl glycerol. In the second step, asymmetrical TAGs are synthesized.

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Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Author:Tahira Musarrat
Referee:Arvid Kappas, Gerd-Volker Roeschenthaler, Adam Le Gresley
Advisor:Nikolai Kuhnert
Persistent Identifier (URN):urn:nbn:de:gbv:579-opus-1011087
Document Type:PhD Thesis
Date of Successful Oral Defense:2021/10/06
Date of First Publication:2022/08/04
Academic Department:Life Sciences & Chemistry
PhD Degree:Chemistry
Focus Area:Health
Other Countries Involved:United Kingdom
Call No:2021/27

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