132072-50-5Relevant articles and documents
Epoxidation of polyunsaturated fatty acid double bonds by dioxirane reagent: Regioselectivity and lipid supramolecular organization
Grabovskiy, Stanislav A.,Kabal'nova, Natalia N.,Chatgilialoglu, Chryssostomos,Ferreri, Carla
, p. 2243 - 2253 (2007/10/03)
The use of dimethyldioxirane (DMD) as the epoxidizing agent for polyunsaturated fatty acids was investigated. With fatty acid methyl esters, this is a convenient method for avoiding acidic conditions, using different solvents, and simplifying the isolation procedures, with less contamination due to by-products. The reagent was also tested with free fatty acids in water. In this case, the supramolecular organization of fatty acids influenced the reaction outcome, and the epoxidation showed interesting regioselective features. The C=C bonds closest to the aqueous-micelle interface is the most favored for the interaction with dimethyldioxirane. The preferential epoxidation of linoleic acid (=(9Z,12Z)-octadeca-9,12-dienoic acid) to the 9,10-monoepoxy derivative was achieved, with a high yield and 65% regioselectivity. In case of arachidonic acid (=(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acid) micelles, the regioselective outcome with formation of the four possible monoepoxy isomers was studied under different conditions. It resulted to be a convenient synthesis of 'cis-5,6-epoxyeicosatrienoic acid' (=3-[(2Z,5Z,8Z)-tetradeca-2,5,8- trienyl]oxiran-2-butanoic acid), whereas in reverse micelles, epoxidation mostly gave 'cis-14,15-epoxyeicosatrienoic acid (= (5Z,8Z,11Z)-13-(3-pentyloxiran-2- yl)trideca-5,8,11-trienoic acid).
Use of cis-Epoxyeicosantrienoic acids and inhibitors of soluble epoxide hydrolase to reduce pulmonary infiltration by neutrophils
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Page/Page column 12, (2008/06/13)
It has now been discovered that inhibitors of soluble epoxide hydrolase (“sEH”) are useful in reducing the severity of or inhibiting the progression of obstructive pulmonary diseases, restrictive airway diseases, and asthma. Administering a cis-epoxyeicosantrienoic acid (“EET”) in addition to the inhibitor is at least additive, and may be synergistic, in reducing or inhibiting these conditions and diseases, as measured by reduced numbers of neutrophils present in the lung. The inhibitor of sEH may be a nucleic acid, such as a small interfering RNA.
ARACHIDONATE EPOXXGENASE: TOTAL SYNTHESIS OF BOTH ENANTIOMERS OF 8,9- AND 11,12-EPOXYEICOSATRIENOIC ACID
Mosset, Paul,Yadagiri, Pendri,Lumin, Sun,Capdevila, Jorge,Falck, J. R.
, p. 6035 - 6038 (2007/10/02)
Both enantiomers of the epoxygenase metabolites 8,9- and 11,12-epoxyeicosatrienoic acid (EET) were synthesized by a convergent strategy utilizing dimethyl D- or L-malate and erythrospecific epoxidation.
Differentiation of Monoepoxide Isomers of Polyunsaturated Fatty Acids and Fatty Acid Esters by Low-Energy Charge Exchange Mass Spectrometry
Keough, Thomas,Mihelich, Edward D.,Eickhoff, David J.
, p. 1849 - 1852 (2007/10/02)
Low-energy charge exchange mass spectrometry is a convenient technique for the unambiguous differentiation of monoepoxide isomers of polyunsaturated fatty acids, fatty acid methyl esters, and fatty acetates.This technique eliminates multistep derivatization procedures which are typically utilized prior to characterization of these isomers with conventional electron ionization mass spectrometry.
