Mechanism of linoleic acid hydroperoxide reaction with alkali

Lipids

Volumn 31, Issue 10, 1996, Pages 1023-1028

  Gardner, Harold W ^a   Simpson, Thomas D ^a   Hamberg, Mats ^b  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI; HYDROPEROXIDE; HYDROXYACID; LINOLEIC ACID;

ARTICLE; EPOXIDATION; FATTY ACID OXIDATION; MOLECULAR INTERACTION;

EID: 0029843898     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02522458     Document Type: Article

References (11)

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2. Simpson, T.D., and Gardner, H.W. (1993) Conversion of 13(S)-Hydroperoxy-9(Z),11(E)-octadecadienoic Acid to the Corresponding Hydroxy Fatty Acid by KOH: A Kinetic Study, Lipids 28, 325-330.
3. Gardner, H.W., Simpson, T.D., and Hamberg, M. (1993) Transformation of Fatty Acid Hydroperoxides by Alkali and Characterization of Products, Lipids 28, 487-495.
4. O'Brien, P.J. (1969) Intracellular Mechanisms for the Decomposition of a Lipid Peroxide. I. Decomposition of a Lipid Peroxide by Metal Ions, Heme Compounds, and Nucleophiles, Can. J. Biochem. 47, 485-492.
5. Hamberg, M. (1988) Fatty Acid Allene Oxides II. Formation of Two Macrolactones from 12,13(S)-Epoxy-9(Z),11-octadecadienoic Acid, Chem. Phys. Lipids 46, 235-243.
6. Hamberg, M., and Gotthammar, B. (1973) New Reaction of Unsaturated Fatty Acid Hydroperoxides: Formation of 11-Hydroxy-12,13-epoxy-9-octadecenoic Acid from 13-Hydroperoxy-9,11-octadecadienoic Acid, Lipids 8, 737-744.
7. Bascetta, E., and Gunstone, F.D. (1984) Attempted Synthesis of (9Z)-Methyl 12-Hydroperoxyoctadec-9-enoate, J. Chem. Soc. Perkin I, 2217-2220.
8. Ratcliffe, R., and Rodehorst, R. (1970) Improved Procedure for Oxidations with the Chromium Trioxide-pyridine Complex, J. Org. Chem. 35, 4000-4002.
9. Anonymous (1971) Official Methods and Recommended Practices of the American Oil Chemists' Society (Link, W.E., ed.) 3rd edn., Method Cd 8-53, American Oil Chemists' Society, Champaign.
10. Behar, D., Czapski, G., Rabani, J., Dorfman, L.M., and Schwarz, H.A. (1970) J. Phys. Chem. 74, 3209-3213.
11. Nakano, M., Takayama, K., Shimizu, Y., Tsuji, Y., Inaba, H., and Migita, T. (1976) Spectroscopic Evidence for the Generation of Singlet Oxygen in Self-reaction of sec-Peroxy Radicals, J. Am. Chem. Soc. 98, 1974-1975.