Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1994-02-25
1996-06-04
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554 5, 554 80, 252397, 252399, 2524002, 25240021, C07C 5150
Patent
active
055234291
DESCRIPTION:
BRIEF SUMMARY
This application is a 3.71 of PCT/EP92/02882 filed Dec. 12, 1992.
BACKGROUND OF THE INVENTION
The present invention relates to the use of N-Acylphosphatidylethanolamine as anti-oxidant for unsaturated fatty acids.
Unsaturated fatty acids are broadly used compounds. They can be found in free form or chemically bound, as in triglycerides, phospholipids and sphingolipids. They are found broadly in nature and are important constituents of the food. Bound to glycerol, as triglycerides, they are present in plant seeds as energy store and are isolated from them as important basic compound for human and animal nutrition. In the phospholipids the unsaturated fatty acids are connected with all cellular membranes. In free form they are the initial products for the biological synthesis of important active products in living species, like e.g. prostaglandins. In all types of incidence the chemically unchanged form is the prerequisite for the accomplishment of the function assigned to the unsaturated fatty acids.
The most serious change is the oxygenation of the double bond in the fatty acid, with as a consequence peroxide formation and a radical chain reaction, which leads to a cleavage of the fatty acids. These reactions nay be in full control, but can also be uncontrolled. Examples of controlled oxidation are the metabolism of nutrition as energy source, the immunological resistance against bacteria and parasites and the synthesis of mediators like prostaglandins.
The radicals which are formed at the uncontrolled radical chain reaction can not only react with fatty acids but also with proteins and nucleic acids. The reaction products lead to pathological changes in the organism.
The uncontrolled oxidation is inhibited by anti-oxidants, which are taken up with the food, or are synthesised in the organism. Deficient nutrition, pathological changes and the process of ageing can lead to a deficiency in anti-oxidants.
The oxidation of consumption fats is always unwanted and leads to products, which are toxicologically unsat and which make the nutrient unpalatable by changes in the taste. These changes can be inhibited by anti-oxidants and as much as possible by the exclusion of oxygen.
Due to the large presence in different biological systems and the great importance of unsaturated fatty acids, the properties of anti-oxidants for the protection of unsaturated fatty acids are subject to various conditions. Up to now none of the known anti-oxidants fulfils the majority of these conditions.
The most used natural anti-oxidants are .alpha.-tocopherol and .beta.-carotene are on the one hand perfectly efficacious but unstable in the presence of oxygen and light. Also the heat stability which is important in the use of some foodstuffs like oils, is limited.
Furthermore there is a complicated isolation process or a synthesis which makes the product expensive.
Ascorbic acid has the disadvantage, that it is not soluble in oils and for that matter only effective in aqueous surroundings, so that it can inhibit the oxidation of fatty acids which are present in the fat phase only to a limited extent. A further disadvantage is the fact, that ascorbic acid can be an oxidative agent in combination with iron salts.
Furthermore synthetic phosphatides as well as phosphatides isolated from plant and animal fats and oils were investigated on their anti-oxidant properties against the autoxidation of fats and oils alone and in combination with additives.
The results obtained are however strongly contradictory.
For instance is the investigation of crude lecithin and its ethanol-soluble and ethanol-insoluble fractions described by A. Nasner in Fette, Seife, Anstrichmittel 12 (1985) pp. 477-481 to determine their anti-oxidative efficacy in storage tests with sunflower oil and lard. He found, that the anti-oxidative effects depend on the type of lecithin fraction used. The ethanol-soluble fraction of the soybean lecithin with the largest portion of phosphatidylethanolamine showed the best effects. The inhibition of the oxidation of lard with a con
REFERENCES:
"Role of Seed Phosphatides as Antioxidants for Ghee (Butter Fat)" by Iqbal S. Bhatia, Narinder Kaur & Pritam S. Sukhija, J.Sci.Fd Agric. 1978, 29, 747-752.
"Phospholipids plus Tocopherols Increase Soybean Oil Stability" by D. H. Hildebrand, JAOCS, vol. 61, No. 3 (Mar., 1984).
"Die antioxidativen Eigenschaften von Lecithin" by Von Alice Nasner, Fette Seifen Anstrichmittel, 87 Jahrgang, No. 12 (1985).
"Antioxygen & Peroxide Decomposition Properties of Antarctic Krill Lipids" by Jong-Ho Lee, K. Fujimoto & T. Kaneda, Bulletin of the Japanese Society of Scientific Fisheries, pp. 881-888 (1981).
"Peroxide-decomposing Activities of Antarctic Krill Lipids & Certain other Oils" by J. Lee, K. Fujimoto & T. Kaneda, Biol. Chem, pp. 2001-2007, (1983).
"The Antioxidant Effects of Phospholipids on Perilla Oil", by M. Kashima, JAOCS, vol. 68, No. 2, (Feb. 1991) pp. 119-121.
"Phase Behavior of Synthetic N-acylethanolamine Phospholipids", by J. L. Newman, D. I. Stiers, W. H. Anderson & H. H. O. Schmid, Chemistry and Physics of Lipids, 42 (1986) 249-260, Elsevier Scientific Publishers Ireland Ltd.
Masui, "Compositions containing unsaturated fatty acids and their stabilization", Chemical Abstracts, abstract of DE-3,419,796, 102:80747, vol. 102, #10, pp. 103, 1985.
Carr Deborah D.
Dees Jos,e G.
Rhone-Poulenc Rorer-GmbH
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