140670-39-9

Upstream product

• 10417-94-4 all cis-5,8,11,14,17-eicosapentaenoic acid 
• 56-81-5 glycerol 
• 1048012-00-5 (2,2-dimethyl-1,3-dioxolan-4-yl)methyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate 
• 85916-97-8 5,8,11,14,17-eicosapentaenoyl chloride 

Relevant academic research and scientific papers

Synthesis of Triacylglycerol from Polyunsaturated Fatty Acid by Immobilized Lipase

More than 95percent of polyunsaturated acid (PUFA) was converted to triacylglycerol by immobilized lipase from Candida antarctica or Rhizomucor miehei.The esterification was carried out at 50-60 deg C with shaking and dehydration for 24 h.The substrates consisted of glycerol and free fatty acid or ethyl esters of the fatty acid at a 1:3 molar ratio.The docosahexaenoic acid (DHA) or eicosapentaenoic acid (EPA) in the substrate polymerized during the reaction, and they required 5-10percent more than the stoichiometric amount to compensate for the PUFA loss.On the contrary, ethyl esters of DHA and EPA were not polymerized.Pure tridocosahexaenoyl, trieicosapentaenoyl and triarachidonoyl glycerol were isolated after passing the product through a basic aluminum oxide column.Industrial feasibility of this process was discussed for the ethyl ester as substrate. KEY WORDS: Docosahexaenoic acid, docosahexaenoyl ethyl ester, eicosapentaenoic acid, immobilized lipase, lipase, polyunsaturated fatty acid, triacylglycerol, triarachidonoyl glycerol, tridocosahexaenoyl glycerol, trieicosapentaenoyl glycerol.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION

The disclosures herein provide compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These compounds may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral administration, intravenous, spray, parenteral, lozenge, solution, syrup, sachet, transdermal administration, or injection. Such compositions may be used to treatment of inflammation or its associated complications.

Compositions and methods for the treatment of urea cycle disorders and gout

The disclosures herein provide compounds of Formula I, Formula II, Formula III, Formula IV, Formula V, Formula VI and Formula VII or its pharmaceutical acceptable compositions and salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. The pharmaceutical compositions may be formulated for oral administration, delayed release or sustained release, transmucosal, syrup, topical, parenteral administration, injection, subdermal, oral solution, rectal administration, nanoparticle, buccal administration or transdermal administration. Such compositions may be used to treatment of urea cycle disorders and gout or its associated complications.

Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity

Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A2 and cyclooxygenase-2.

POLYUNSATURATED FATTY ACID MONOGLYCERIDES, DERIVATIVES, AND USES THEREOF

The invention emcompasses polyunsaturated fatty acid monoglycerides and derivatives thereof, having the formulae (I), (II), (III) and (IV), pharmaceutically acceptable salts thereof, compositions thereof and processes of preparing said compounds. These compounds can be useful as cancer chemopreventive agents, cancer treating agents, or radioenhencers for radiotherapy of cancer, or for inhibiting tumor growth or cell proliferation, or reducing tumor growth.

COMPOSITIONS COMPRISING POLYUNSATURATED FATTY ACID MONOGLYCERIDES OR DERIVATIVES THEREOF AND USES THEREOF

There are provided various compounds and compositions comprising polyunsaturated fatty acid monoglycerides and derivatives thereof. These compounds and compositions can be useful as cancer chemopreventive agents. They can also be useful for enhancing solubility of various active agents and enhancing their bioavailability.

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.

The Synthesis of Homogeneous Triglycerides of Eicosapentaenoic Acid and Docosahexaenoic Acid by Lipase

A highly efficient synthesis of homogeneous triglycerides of either pure eicosapentaenoic acid, 1, or docosahexaenoic acid, 2, by an immobilized non-regiospecific yeast lipase from Candida antarctica is described.Two methods were used: Interesterification of tributyrin and direct esterification of glycerol with stoichiometric amount of 99percent EPA or DHA as ethyl esters and free fatty acids, respectively.Both processes were performed under vacuum at 65 deg C in the absence of any solvent.The volatile co-products were condensed into a cooled trap, thus shifting the equilibrium toward completion.Complete incorporation was reached in less than 72 h for all cases, but the direct esterification was found to proceed considerably faster than the transesterification as were both processes involving EPA as compared to DHA.High-field 1H NMR spectroscopy analysis offered detailed investigation of the intermediate glycerides during the direct esterification reaction.The purity of the resulting crude products which were afforded in excellent yields was very high.