• Title/Summary/Keyword: Oxalyl Chloride

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Elimination of Saturated Fatty Acids, Toxic Cyclic nonapeptide and Cyanogen Glycoside Components from Flax Seed Oil

  • Choi, Eun-Mi;Kim, Jeung-Won;Pyo, Mi-Kyung;Jo, Sung-Jun;Han, Byung-Hoon
    • Biomolecules & Therapeutics
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    • v.15 no.1
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    • pp.65-72
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    • 2007
  • Flax seed(Linseed, Linum usitatissimum L.) and its oil, a richest source of alpha-linolenic acid(ALA)(${\omega}-3$), contain saturated fatty acids, neurotoxic cyanogen glycosides and immuno-suppressive cyclic-nonapeptides. Present paper describes the development of two chemical processes, Process-A and -B, to remove saturated fatty acids and to destroy cyclic nonapeptides and cyanogen glycosides from flax seed oil. Process-A consists of three major steps, i.e., extraction of fatty acid mixture by alkaline saponification, removal of saturated fatty acid by urea-complexation, and triglyceride reconstruction of unsaturated fatty acid via fatty acyl-chloride activation using oxalyl chloride. Process-B consists of preparation of fatty acid ethyl ester by transesterification, elimination of saturated fatty acid ester by urea-complexation, and reconstruction of triglyceride by interesterification with glycerol-triacetate (triacetin). The destruction of lipophilic cyclic nonapeptide during saponification or transesterification processes could be demonstrated indirectly by the disappearance of antibacterial activity of bacitracin, an analogous cyclic-decapeptide. The cyanogen glycosides were found only in the dregs after hexane extraction, but not in the flax seed oil. The reconstructed triglyceride of flax seed oil, obtained by these two different pathways after elimination of saturated fatty acid and toxic components, showed agreeable properties as edible oil in terms of taste, acid value, iodine and peroxide value, glycerine content, and antioxidant activity.

Synthesis and Characterization of High Molecular Weight Biodegradable Polyoxalate (고분자량 생분해성 폴리옥살레이트의 합성과 특성분석)

  • Kim, Se-Ho;Yoo, Han-Na;Khang, Gil-Son;Lee, Dong-Won
    • Polymer(Korea)
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    • v.34 no.6
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    • pp.547-552
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    • 2010
  • Biodegradable polymers have gained enormous attentions in the pharmaceutical and biomedical applications, especially in drug delivery. In this work, we report the synthesis and characteristics of high molecular weight polyoxalate with ~75000 Da. Hydrolytic degradation kinetics and degradation products were characterized by nuclear magnetic resonance and gel permeation chromatography. Polyoxalate is a semicrystalline and thermally stable polymer with a glass transition temperature of ${\sim}35^{\circ}C$, which is suitable for drug delivery applications. The hydrophobic nature of polyoxalate allows it to be formulated into nanoparticles and encapsulate drugs using a conventional oil-in-water emulsion/solvent displacement method. Polyoxalate nanoparticles also exhibited excellent cytotoxicity profiles. It can be suggested that polyoxalate has great potential for numerous biomedical and pharmaceutical applications.