Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2001-11-21
2003-08-19
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C514S560000, C424S442000, C424S451000, C426S807000
Reexamination Certificate
active
06608222
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to the field of human and animal nutrition, and in particular to nutritional compositions containing bioactive glycerides of conjugated linoleic acid (BG-CLA).
Conjugated linoleic acid (CLA), generally understood as a family of positional and geometric isomers of linoleic acid (cis-9, cis-12-octadecadienoic acid), has been and is the focus of numerous research programs that seek to capitalize on its nutritional, therapeutic, and pharmacological properties. However the biological activity associated with CLA is diverse and complex and past testing has generated claims that are diametrically opposed to each other in terms of the active biologic isomer. The potential beneficial effects of CLA supplementation are apparent. Several criteria have been used for selecting CLA compositions for specific applications. The factors of significance have centered on the inclusion of a specific bioactive isomer or multiple bioactive isomers in a defined isomeric ratio. Other factors that affect the feasibility and performance of CLA isomers' composition include ingredient cost, toxicity, taste, and effect on subject within the diet.
CLA has been incorporated into the diet in liquid, gel or powdered forms, though the preferred method of administration is generally oral. The CLA has also been formulated with suitable carriers such as starch, sucrose or lactose in tablets, capsules, solutions and emulsions. CLA preparations are also provided as supplements in various prepared food products. A wide range of existing applications where CLA is directly incorporated into prepared food products includes diet products (diet drinks, diet bars and prepared frozen meals) and non-diet products (candy, snack products such as chips, prepared meat products, milk, cheese, yogurt and any other fat or oil containing foods).
Currently, most CLA manufactured is by the aikali isomerization process. The reaction product obtained from these processes is a mixture of CLA, linoleic acid and the other fatty acids found in the source oil. Generally, the amount of CLA derived from alkali isomerization of safflower oil is about 60% of the total free fatty acid product. Another method of producing a preparation consisting of primarily cis-9, trans-11 CLA is where linoleic acid is incubated with the microorganism
Butyrivibrio fibrisolvens.
CLA is also naturally obtained in tall oil, a by-product of the kraft paper process. Further refining of tall oil results in a CLA enriched Modified Tall Oil (MTO) as incorporated herein by reference to U.S. Pat. No. 6,020,377 titled “Modified tall oil supplemented diet for growing-finishing pigs”. Because of the huge output of tall oil in the paper industry each year, MTO could be readily available and very inexpensive. MTO however provides the CLA in the free fatty acid form and not the triglyceride form.
As an alternate to alkaline saponification and re-esterification with glycerin, it is possible to catalytically isomerize high linoleic acid triglyceride “LA-TG” (non-conjugated) oils directly into triglyceride oil containing a significantly higher percentage of conjugated linoleic acid triglycerides “CLA-TG”. Again the early work (1950-1960) was directed toward improving drying oils by increasing the conjugated double bond content of normal non-conjugated di- and poly-unsaturated oils (triglyceride forms).
Early work demonstrated that nickel metal deposited on activated carbon (Ni/C) could be an effective isomerization catalyst for converting the non-conjugated double bond system of the linoleic acid groupings of vegetable oil triglycerides (at least partially) into a conjugated double bond system. J. C. Cowan, et al.
Ind. Eng. Chem.
40:997-1002 (1946). Cowan, et al. demonstrated that conjugation could be induced to the extent of about 30% in high LA-TG vegetable oils, mainly soybean and linseed oils. It was interesting to note that the action of Ni/C on dehydrate castor oil “DCO” could increase conjugated diene content from a starting 30% CLA-TG content to a significantly higher 39% value.
Although safflower oil was not included in Cowan's original study, another study did concentrate on safflower oil (JAOCS, July 1948 page 237). Anthraquinone (AQ) was found to be a more effective isomerization catalyst as compared to Ni/C in this study. Whereas the action of Ni/C on safflower oil resulted in about 12-15% conjugation, AQ consistently brought conjugation up to about 25%. Early studies (1946 and 1948) did not spell out the resulting structure of the CLA-TG due to their only interest being the conjugated diene content as a reflection of the drying oil efficiency. The fact that high LA-TG's were the starting materials naturally implies that isomerization would lead to conjugated LA (i.e., CLA-TG) groupings in the final conjugated diene structures.
Alternative prior art methods and processes utilizing or creating conjugated linoleic acid differ from the invention. The U.S. Pat. No. 6,060,514 titled “Isomer enriched conjugated linoleic acid compositions” utilizes a Diels-Alder reaction method to obtain an acrylic adduct. The U.S. Pat. No. 6,042,869 titled “Bulk animal feeds containing conjugated linoleic acid” and U.S. Pat. No. 6,015,833 titled “Conjugated linoleic acid compositions” both utilize an alkaline saponification method to obtain conjugated linoleic acid in the free fatty acid form. The U.S. Pat. No. 5,892,074 titled “Synthesis of conjugated linoleic acid (CLA)” utilizes an expensive tosylate procedure to obtain conjugated linoleic acid. Lastly, the U.S. Pat. No. 5,719,301 titled “Method of conjugating double bonds in drying oils” utilizes a ruthenium compound as an isomerization catalyst to maximize the conjugation of both linoleic and linolenic acids for drying oil applications in the wood bonding industry. The choice of linseed oil as the preferred organic compound is indicative of its intent to maximize conjugation, due to the preferential conjugation of linolenic acid's three double bonds as compared to linoleic acid's two double bonds.
CLA is historically an expensive product with conclusive health and nutritional benefits. One mechanism whereby CLA reduces body fat is by enhancing insulin sensitivity so that fatty acids and glucose can pass through muscle cell membranes and away from fat tissue. CLA may help block fat cells that are in the body from filling up with fat. CLA also may have some effect on skeletal muscle, possibly stimulating muscle growth and fat burning. CLA inhibits the body's mechanism for storing fat and causes the body to utilize fatty reserves for energy. CLA also increases hormone sensitive lipase activity. This is an enzyme that breaks down fats stored in fat cells on the body. The fatty acids are returned to the blood stream to be used by muscle cells as an energy source. CLA has been shown to inhibit lipoprotein lipase. This is an enzyme that breaks down fat globules in the blood so that adipocyte (fat cell) uptake (body fat accumulation) can occur. The inhibition of lipoprotein lipase results in reduced fat deposition. CLA also has powerful antioxidant properties. It has been proposed that adding CLA to foods may prevent mold growth and oxidation. Thus, it is likely that the basis for the effect of CLA is an inhibition of lipid filling or an increase in lipid mobilization.
Another alternative method to achieve comparable benefits in feed efficiency of animals, dietary supplements for optimal weight gain and lean tissue of animals, nutritional benefits in human consumption as dietary supplements is L-carnitine. Work has been performed with Carnitine to achieve certain of these results and varying degrees of success have been achieved. Carnitine is chemically termed 3-hydrosy-4-N-trimethylamine butyric acid, and is similar to choline and a close cousin to amino acids. Unlike amino acids, Carnitine is not used for protein synthesis. Only the L-isomer of Carnitine is biologically active.
Carnitine is essential in the metabolism and movement of fatty acids with
Bonsignore Patrick V.
Gurin Michael H.
Alpha Food Ingredients, Inc.
Carr Deborah D.
Rosenbaum David G.
Rosenbaum & Associates P.C.
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