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Epoxidation reactions of unsaturated fatty esters with potassium peroxomonosulfate

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Lipids

Abstract

Epoxidation of the double bond in methyl oleate, octadec-11E-en-9-ynoate, ricinoleate (12-hydroxy-octadec-9Z-enoate), iso-ricinoleate (9-hydroxy-octadec-12Z-enoate), and 12-oxo-octadec-9Z-enoate with potassium peroxomonosulfate (oxone, 2 KHSO5.K2SO4) in the presence of trifluoroacetone or methyl pyruvate gave the corresponding monoepoxy derivatives. Reaction of Oxone® with methyl linoleate and octadeca-9Z,11E-dienoate furnished the corresponding diepoxystearate derivative. Methyl 9,12-dioxo-octadec-10Z-enoate was obtained when a C18 furanoid fatty ester (methyl 9,12-epoxy-9,11-octadecadienoate) was treated with Oxone®. The yield of these reactions was very high (85–99%), and the epoxy derivatives were readily isolated by solvent extraction. The products were identified by spectroscopic methods.

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Abbreviations

COSY:

homonuclear correlation spectroscopy

IR:

infrared

m-CPBA:

m-chloroperoxybenzoic acid

MMPP:

magnesium monoperoxyphthalate, hexahydrate

NMR:

nuclear magnetic resonance

TLC:

thin-layer chromatography

TMS:

tetramethylsilane

References

  1. Abbot, G.G., and Gunstone, F.D. (1971) The Formation of Some vic-Substituted Epoxyoctadecanoates and Their Conversion to 1,4-Epoxides and Other Compounds, Chem. Phys. Lipids 7, 290–302.

    Article  CAS  Google Scholar 

  2. Lam, C.K. (1995) Oxidation Reaction of Unsaturated Long-Chain Fatty Esters: A Sonochemical Approach, M. Phil. Thesis, The University of Hong Kong, Hong Kong.

    Google Scholar 

  3. Lie Ken Jie, M.S.F., Pasha, M.K., and Lam C.K. (1997) Ultrasonically Stimulated Oxidation Reactions of 2,5-Disubstituted C18 Furanoid Fatty Ester, Chem. Phys. Lipids 85, 101–106.

    Article  CAS  Google Scholar 

  4. Cooper, M.S., Heaney, H., Newbold. A.J., and Sanderson, W.R. (1990) Oxidation Reactions Using Urea-Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide. SYNLETT, 533–535.

  5. Brougham, P., Cooper, M.S., Cummerson, D.A., Heaney, H., and Thompson, N. (1987) Oxidation Reactions Using Magnesium Monoperphthalate: A Comparison with m-Chloroperoxybenzoic Acid, Synthesis 1015–1017.

  6. Adam, W., Curci, R., and Edwards, J.O. (1989) Dioxiranes: A New Class of Powerful Oxidants, Acc. Chem. Res. 22, 205–211.

    Article  CAS  Google Scholar 

  7. Murray, R.W. (1989) Dioxiranes, Chem. Rev. 89, 1187–1201.

    Article  CAS  Google Scholar 

  8. Lie Ken Jie, M.S.F., Pasha, M.K., and Alam, M.S. (1997) Synthesis and Nuclear Magnetic Resonance Properties of All Geometrical Isomers of Conjugated Linoleic Acids, Lipids 32, 1041–1044.

    Google Scholar 

  9. Lie Ken Jie, M.S.F., Pasha, M.K., and Almad, F. (1996) Ultrasound-Assisted Synthesis of Santalbic Acid and a Study of Triacylglycerol Species of Santalum album (Linn.) Seed Oil, Lipids 31, 1083–1089.

    Article  PubMed  CAS  Google Scholar 

  10. Gunstone, F.D. (1954) The Nature of the Oxygenated Acid Present in Vernonia anthelmintica (Wild.) Seed Oil, J. Chem. Soc., 1611–1616.

  11. Lie Ken Jie, M.S.F., Syed-Rahmatullah, M.S.K., and Wong, K.P. (1992) Efficient Synthesis of Long-Chain Furanoid Fatty Ester Derivative from Methyl Ricinoleate, Nat. Prod. Letters 1, 93–98.

    Google Scholar 

  12. Tulloch, A.P., and Mazurek, M. (1976) 13C Nuclear Magnetic Resonance Spectroscopy of Saturated, Unsaturated, and Oxygenated Fatty Acid Metyl Esters, Lipids 11, 228–234.

    CAS  Google Scholar 

  13. Gunstone, F.D. (1993) The Study of Natural Epoxy Oils and Epoxidized Vegetable Oils by 13C Nuclear Magnetic Resonance Spectroscopy, J. Am. Oil Chem. Soc. 70, 1139–1144.

    CAS  Google Scholar 

  14. Pasha, M.K., and Ahmad, F. (1993) Synthesis of Oxygenated Fatty Acid Esters from Santalbic Acid Ester, Lipids 28, 1027–1031.

    CAS  Google Scholar 

  15. Lie Ken Jie, M.S.F., and Lam, C.K. (1995) Ultrasound-Assisted Epoxidation Reaction of Long-Chain Unsaturated Fatty Esters, Ultrasonic Sonochem. 2, S11–14.

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong

    Marcel S. F. Lie Ken Jie & Mohammed Khysar Pasha

Authors
  1. Marcel S. F. Lie Ken Jie
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  2. Mohammed Khysar Pasha
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Correspondence to Marcel S. F. Lie Ken Jie.

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Lie Ken Jie, M.S.F., Pasha, M.K. Epoxidation reactions of unsaturated fatty esters with potassium peroxomonosulfate. Lipids 33, 633–637 (1998). https://doi.org/10.1007/s11745-998-0250-6

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  • DOI: https://doi.org/10.1007/s11745-998-0250-6

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