24529-89-3

Usage

Uses

Used in Medical Applications:
(S)-2,3-Bis(linoleoyloxy)-1-propanol is used as a biomarker for the early detection of preeclampsia in pregnant women. Its upregulation in certain pregnancies serves as an indicator of the potential development of this hypertensive disorder later in the pregnancy, allowing for timely medical intervention and management.
Used in Pharmaceutical Research:
As a component of biological membranes, (S)-2,3-Bis(linoleoyloxy)-1-propanol may be utilized in the study of membrane structure, function, and interactions with other molecules. This knowledge can contribute to the development of new drugs and therapies targeting membrane-related diseases or conditions.
Used in Lipid Biochemistry:
(S)-2,3-Bis(linoleoyloxy)-1-propanol can be employed as a research tool in the field of lipid biochemistry to investigate the properties and roles of diacylglycerols and their derivatives in cellular processes, such as signal transduction and energy metabolism.
Used in Nutritional Science:
Understanding the presence and function of (S)-2,3-Bis(linoleoyloxy)-1-propanol in biological membranes can provide insights into the role of linoleic acid and other polyunsaturated fatty acids in human health and nutrition, potentially leading to the development of dietary recommendations or supplements.

Upstream product

• 537-40-6 1,2,3-tri(cis,cis-9,12-octadecadienoyloxy)propane 
• 60-33-3 linoleic acid 
• 56-81-5 glycerol 
• 189450-64-4 (9Z,12Z)-Octadeca-9,12-dienoic acid 1-((9Z,12Z)-octadeca-9,12-dienoyloxymethyl)-2-(9-phenyl-9H-xanthen-9-yloxy)-ethyl ester 
• 125291-01-2 (9Z,12Z)-Octadeca-9,12-dienoic acid (R)-1-(2-methoxy-ethoxymethoxymethyl)-2-((9Z,12Z)-octadeca-9,12-dienoyloxy)-ethyl ester 
• 6542-05-8 1,2-Dilinoleoyl-sn-glycerol-3-phosphorylcholine 

Downstream Products

• 6542-05-8 1,2-Dilinoleoyl-sn-glycerol-3-phosphorylcholine 
• 998-06-1 (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate 
• 816-94-4 {2-[(2,3-bis-stearoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium betaine 

Relevant academic research and scientific papers

Distinct roles of adipose triglyceride lipase and hormone-sensitive lipase in the catabolism of triacylglycerol estolides

Branched esters of palmitic acid and hydroxy stearic acid are antiinflammatory and antidiabetic lipokines that belong to a family of fatty acid (FA) esters of hydroxy fatty acids (HFAs) called FAHFAs. FAHFAs themselves belong to oligomeric FA esters, known as estolides. Glycerol-bound FAHFAs in triacylglycerols (TAGs), named TAG estolides, serve as metabolite reservoir of FAHFAs mobilized by lipases upon demand. Here, we characterized the involvement of two major metabolic lipases, adipose triglyceride lipase (ATGL) and hormone-sensitive lipase (HSL), in TAG estolide and FAHFA degradation. We synthesized a library of 20 TAG estolide isomers with FAHFAs varying in branching position, chain length, saturation grade, and position on the glycerol backbone and developed an in silico mass spectra library of all predicted catabolic intermediates. We found that ATGL alone or coactivated by comparative gene identification-58 efficiently liberated FAHFAs from TAG estolides with a preference for more compact substrates where the estolide branching point is located near the glycerol ester bond. ATGL was further involved in transesterification and remodeling reactions leading to the formation of TAG estolides with alternative acyl compositions. HSL represented a much more potent estolide bond hydrolase for both TAG estolides and free FAHFAs. FAHFA and TAG estolide accumulation in white adipose tissue of mice lacking HSL argued for a functional role of HSL in estolide catabolism in vivo. Our data show that ATGL and HSL participate in the metabolism of estolides and TAG estolides in distinct manners and are likely to affect the lipokine function of FAHFAs.

IONIZABLE LIPIDS FOR NUCLEIC ACID DELIVERY

The present document describes compounds, or pharmaceutically acceptable salt thereof, of a core formula (I) where R1 features an amine group, particularly useful in the formulation of lipid particles including nucleic acid therapeutic agents, or proteins, or both, and for delivery of nucleic acid and protein therapeutics to cells in vivo or ex vivo, including anticancer and vaccine applications.

MODIFIED AMINE LIPIDS

The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.

Highly efficient solvent-free synthesis of 1,3-diacylglycerols by lipase immobilised on nano-sized magnetite particles

Recently, 1,3-DAGs (1,3-diacylglycerols) have attracted considerable attention as healthy components of food, oil and pharmaceutical intermediates. Generally, 1,3-DAG is prepared by lipase-mediated catalysis in a solvent free system. However, the system's high reaction temperature (required to reach the reactants' melting point), high substrate concentration and high viscosity severely reduce the lipase's activity, selectivity and recycling efficiency. In this report, MjL (Mucor javanicus lipase) was found to have the best performance in the solvent-free synthesis of 1,3-DAGs of several common commercial lipases. By covalent binding to amino-group-activated NSM (nano-sized magnetite) particles and cross-linking to form an enzyme aggregate coat, MjL's specific activity increased 10-fold, and was able to be reused for 10 cycles with 90% residual activity at 55 °C. 1,3-DAGs of lauric, myristic, palmitic, stearic, oleic and linoleic acid were prepared using the resulting immobilised enzyme, all with yields greater than 90%, and the reaction time was also greatly reduced.

Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system

1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.

Preparation of 2-O-arachidonoyl-1-O-stearoyl-sn-glycerol and other di-O-acyl glycerol derivatives

R(-)-2,3- and S(+)-1,2-O-Isopropylidene-sn-glycerols (4 and 9) are converted into 2-O-arachidonoyl-1-O-stearoyl and 2-O-arachidonoyl-3-O-stearoyl-sn-glycerols (2 and 3, respectively); glycerol is also converted into its racemic 1,2- and its symmetrical 13-di-O-linoleoyl derivatives (14 and 17, respectively).

Synthesis of Triacylglyceride Hydroperoxides Derived from Linoleic Acid

Four triacylglyceride hydroperoxides were synthesized by DCC-mediated esterification of a dimethylperketal of 13-hydroperoxyoctadecadienoic acid with glycerides, in which on e or two linoleoyl groups were linked, and by final removal of the protective group with a mixture of THF, acetic acid and water.

SYNTHESIS OF OPTICALLY ACTIVE POLYUNSATURATED DIACYLGLYCEROLS

1,2-Isopropylidene-3-methoxyethoxymethyl-sn-glycerol (2) is used to access complex polyunsaturated diacylglycerols of high optical purity such as 1,2-dilinoleoyl-sn-glycerol (5).Using a similar methodology its enantiomer, 2,3-dilinoleoyl-sn-glycerol, can be obtained from 1-methoxyethoxymethyl-2,3-isopropylidene-sn-glycerol.

Phospholipid Oxidation Catalyzed by Ferrous Ion and Ascorbic Acid

Phosphatidylethanolamine (PE) is generally more oxidizable than phosphatidylcholine (PC).To determine the difference in reactivities to oxidation between PE and PC, it is necesary for their fatty acid moieties to be uniform.Experimental results of the ferrous ion-catalyzed oxidation of dilinoleoylphosphatidylcholine, dilinoleoylphosphatidylethanolamine, and dilinoleoyldiglyceride revealed that the rate of oxidation depends on the type of base.Ferrous ion possessed a high catalytic activity in hydroperoxide formation at pH 5.8.Iron ions might initiate the oxidation of phospholipids by forming free radicals.Phosphoethanolamine was capabale of trapping ferrous ion and preventing it form being autoxidized to ferric ion.Trapping of ferrous ion might be responsible for the significant oxidizability of PE at pH 5.8-7.0.In the ferrous ion-ascorbic acid (AsA) catalyzed oxidation sytem, PC oxidation was remarkably enchanced at pH 7.0.In this case, no reduction of ferric ion occured, but AsA had a prooxidant effect of accelerating the formation of free radicals.