Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
1999-10-29
2001-01-23
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...
C554S173000, C554S126000
Reexamination Certificate
active
06177580
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to synthetic triglycerides containing C
6-24
fatty acid residues, with the proviso that at least one residue is a conjugated linoleic acid residue, and to a process for the production of the triglycerides. The invention also relates to the use of the triglycerides in foods and pharmaceutical products.
Polyunsaturated &ohgr;-3 and &ohgr;-6 fatty acids, such as &agr;-linolenic acid and linoleic acid, are among the fatty acids essential to mammals and human beings. Besides linoleic acid, other isomeric octadecadienoic acids occur in nature. They are distinguished by conjugated double bonds at carbon atoms 9 and 11, 10 and 12 and 11 and 13. These isomeric octadecadienoic acids are collectively referred to in the scientific literature as conjugated linoleic acids (abbreviation: CLAs) and have recently attracted increasing attention (NUTRITION, Vol. 19, No. 6, 1995).
Conjugated linoleic acids are present as constituents in various foods. Their main source are animal foods although significant quantities of CLA are also present in milk and milk products. In addition, CLAs have been found in various oils and fats, the concentration in vegetable oils being significantly lower than the concentration in animal fats (J. Food Compos. Anal. 5, 185-197 (1992)).
Various working groups have reported on the significance of CLAs to the organism. Recently, Shultz et al. reported on the inhibiting effect on the in-vitro growth of human cancer cells (Carcinogenesis 8, 1881-1887 (1987) and Cancer Lett. 63, 125-133 (1992)).
In in vitro tests, CLAs were tested for their effectiveness against the growth of malignant human melanomas, colon and breast cancer cells. In the culture media, there was a significant reduction in the growth of the cancer cells treated with CLAs by comparison with control cultures. The mechanism by which CLAs exert anticarcinogenic activity is unknown. In addition, CLAs have a strong antioxidative effect so that, for example, the peroxidation of lipids can be inhibited (Atherosclerosis 108, 19-25 (1994)).
Investigations have also been conducted, for example, into the addition of conjugated linoleic acid to foods for the purpose of color stabilization (JP 06/276939 A2).
The use of conjugated linoleic acid in animal feeds and, in this connection, also in human nutrition is known, for example, from WO 96/06605. This application is concerned with reducing body fat content in animal nutrition. In the statement of problem, the specification also mentions the possibility of application to human beings. In particular, it mentions the use of a fatty emulsion containing 0.5 to 2% by weight of conjugated linoleic acid for oral or intravenous administration to human beings.
EP 0 579 901 B relates to the use of conjugated linoleic acid for avoiding loss of weight or for reducing increases in weight or anorexia caused by immunostimulation in human beings or animals.
WO 94/16690 is concerned with improving the efficiency of food utilization in animals by administering an effective quantity of conjugated linoleic acid.
In connection with the many positive effects of conjugated linoleic acid, as demonstrated in intensive studies, particularly on animals and tissue cultures, the use of conjugated linoleic acid in foods for human consumption has also been discussed. However, the use of free conjugated linoleic acid in foods and pharmaceutical products is limited by the fact that, on the one hand, unwanted reactions with other food constituents can occur where free conjugated linoleic acid is incorporated in complex foods and, on the other hand, by the unpleasant taste and odor of conjugated linoleic acid which can lead to non-acceptance by the consumer. Another disadvantage is that free fatty acids are covered by food additive legislation so that their use in foods is restricted.
Accordingly, the complex problem addressed by the present invention was to find a substitute for conjugated linoleic acid, above all in human nutrition and also for pharmacological use. On the one hand, this substitute would have better organoleptic properties than conjugated linoleic acid and, on the other hand, would lend itself to incorporation in foods without initiating secondary reactions.
DESCRIPTION OF THE INVENTION
Accordingly, the present invention relates to synthetic triglycerides corresponding to formula (I):
in which R
1
, R
2
and R
3
independently of one another represent C
6-24
fatty acid residues, with the proviso that at least one substituent R
1
, R
2
or R
3
is a conjugated linoleic acid residue.
The present invention also relates to a process for the production of synthetic triglycerides by esterification of glycerol or transesterification of triglycerides with fatty acid mixtures by methods known from the prior art, with the proviso that at least 50% by weight of conjugated linoleic acid is used in the fatty acid mixture, the reaction is carried out in an inert gas atmosphere and heating to the reaction temperature is preferably carried out at a heating rate of 0.2 to 10 K per minute.
The present invention also relates to the use of the triglycerides according to the invention in foods and/or as active substances for the production of pharmaceutical products.
It has surprisingly been found that the triglycerides according to the invention are comparable with pure conjugated linoleic acid in their antioxidative and color-stabilizing effect in foods. In addition, they may readily be incorporated in foods and pharmaceutical products without initiating any secondary reactions. In particular, their lipophilic character enables then to be readily incorporated in fat-containing products. The triglycerides according to the invention are also readily absorbed by the animal or human organism. At the same time, they have an almost neutral taste and odor They are therefore far superior in their organoleptic properties to free conjugated linoleic acid. This means, for example, that the triglycerides can be used in larger quantities in foods. Even food supplements consisting of pure triglyceride of conjugated linoleic acid can be taken by mouth by virtue of their outstanding organoleptic properties. Another advantage is that they do not come under food additive legislation, in other words there are no restrictions on their incorporation in foods.
It has also been found that, surprisingly, the triglycerides according to the invention can also readily be obtained in high yields, more particularly by the direction esterification of glycerol with conjugated linoleic acid, providing the reaction is carried out in an inert gas and providing a low heating rate is maintained.
Triglycerides
In the triglycerides of formula (I) according to the invention, at least one of the substituents R
1
, R
2
or R
3
is a conjugated linoleic acid residue while the other constituents represent C
6-24
fatty acid residues. However, triglycerides which, on a statistical average, contain more than 2 conjugated linoleic acid residues per triglyceride are particularly preferred, triglycerides in which the substituents R
1
, R
2
and R
3
represent a conjugated linoleic acid residue being most particularly preferred. In the context of the present invention, triglycerides are also understood to be the technical mixtures of mono-, di- and triglycerides which are obtained in particular in the direct esterification of glycerol with conjugated linoleic acid. A typical composition which is particularly preferred and which is obtained in the process according to the invention, more particularly in the esterification of glycerol with conjugated linoleic acid, contains 60 to 98% by weight and preferably 80 to 98% by weight of a triglyceride of conjugated linoleic acid, 1 to 40 and preferably 1 to 20% by weight of a diglyceride of conjugated linoleic acid and at most 2% by weight and preferably at most 1% by weight of a monoglyceride of conjugated linoleic acid. At the same time, the glyceride to be used in accordance with the invention has an acid value of at most 5 and preferably of at most 3,
Adams Wolfgang
Gaupp Rolf
Gierke Juergen
Sander Andreas
Timmermann Franz
Carr Deborah D.
Drach John E.
Faulkner Diedra
Henkel Kommanditgesellschaft auf Aktien
Trzaska Steven J.
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