異なるアルコール鎖長をもつドコサヘキサエン酸エステルの自動酸化(原標題は英語) Autoxidation of Docosahexaenoate with Different Chain Length of Alcohol

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Four esters of docosahexaenoic acid, methyl (DHA-ME), ethyl (DHA-EE), propyl (DHA-PE) and isopropyl docosahexaenoate (DHA-IE), were synthesized and autoxidized at 25°C to determine how the ester structure provides stability to highly unsaturated fatty acid (HUFA) against oxidation. Stability was assessed based on oxygen absorption during autoxidation. Monohydroperoxide (MHPO) isomers were examined by high-performance liquid chromatography (HPLC). DHA-ME was found to undergo oxidation most rapidly, whereas DHA-IE was most stable toward this process. Induction period of DHA esters was longer with greater alcohol chain length. HPLC demonstrated the presence of ten MHPO positional isomers (4-,7-,8-,10-,11-,13-,14-,16-,17-and 20-MHPO) during autoxidation of the DHA esters. 20-MHPO was the main constituent of any one of these isomers, constituting 20% of total MHPO regardless of the DHA esters. Peroxide had virtually no effect on MHPO isomer compostion. 4-MHPO was produced in the least amount from autoxidized DHA-ME (8%), though more so from autoxidized DHA-IE (17%). More 4-MHPO was obtained from total MHPO with increase in alcohol chain length. MHPO produced from during autoxidation of DHA-EE, DHA-PE and DHA-IE was stable, during its incubation at 25°C, whereas only 4-MHPO of DHA-ME was unstable. Ester structure is thus shown to provide stability toward oxidation and products obtained from the oxidation of DHA.

収録刊行物

  • Journal of oleo science

    Journal of oleo science 51(6), 433-438, 2002-06-01

    Japan Oil Chemists' Society

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各種コード

  • NII論文ID(NAID)
    10008574317
  • NII書誌ID(NCID)
    AA11503337
  • 本文言語コード
    ENG
  • 資料種別
    NOT
  • ISSN
    13473352
  • NDL 記事登録ID
    6261949
  • NDL 雑誌分類
    ZP25(科学技術--化学・化学工業--油脂類)
  • NDL 請求記号
    Z54-J571
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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