Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Reexamination Certificate
2000-01-18
2001-10-02
Jarvis, William R. A. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
C514S558000
Reexamination Certificate
active
06297279
ABSTRACT:
BACKGROUND ART
The invention relates to the field of dietetic lipids, in particular for infant formulas. It relates to a lipid composition which mimics that of human milk.
Human milk fat is composed essentially of triacylglycerols (TAGs) whose fatty acid structure, composition and distribution are specific. It is characterized in particular by the presence of two long-chain polyunsaturated fatty acids (LC-PUFA), arachidonic acid (AA, C20:4, n-6) and docosahexaenoic acid (DHA, C22:6, n-3) predominantly at the 2-position of the triacylglycerol, by the abundance of saturated (SFA) palmitic acid. (P, C16:0) and by the fact that P is predominantly at the 2-position of the triacylglycerol.
Lipid compositions for infant formulas which mimic human milk fat as well as processes for the preparation of such compositions are described in patent EP-B-209327 and in patent applications WO 94/26855 (POT/EP 94/01306) and WO 94/26854 (POT/EP 94/01304). These compositions comprise a mixture of TAGs in which more than 50% of the fatty acids at the 2-position of the triacylglycerol are SFAs, predominantly P, and where the fatty acids at the 1,3-positions of the triacylglycerol comprise medium-chain C
8
-C
14
unsaturated fatty acids (MCFA).
The process for preparing these compositions, which is described in EP-B-209327, consists in an inter-esterification, catalysed by a 1,3-regiospecific lipase of a mixture consisting, on the one hand, of a palm oil fraction comprising 80% of tristearin and 20% of 1,3-dipalmitoyl-2-olein and, on the other hand, of a mixture of free fatty acids containing a substantial quantity of unsaturated fatty acids. Under the action of the 1,3-regiospecific lipase, medium-chain saturated fatty acid residues are introduced at the 1,3-positions of the 2-palmitoyl-glycerides. The free fatty acids of the crude mixture are then removed by steam distillation. The mixture of synthetic TAGs produced is finally mixed with various vegetable oils.
In WO 94/26855, the above mixture of synthetic TAGs, mixed with various vegetable oils in defined portions, is subjected to an interesterification using a 1,3-regiospecific lipase.
In WO 94/26854, where appropriate, after removal of the diglycerides by enzymatic treatment, the trisaturated TAGs are partially removed from the above mixture of synthetic TAGs by interesterification using a 1,3-regiospecific lipase in the presence of an oil which is high in mono- or diunsaturated acids.
The known processes have disadvantages.
Since most of the customary lipases have a low reactivity towards polyunsaturated fatty acids (PUFAs), particularly towards the LC-PUFAs, it is very difficult to incorporate the desired quantities of these fatty acids, in particular of DHA into the TAGs using a 1,3-regiospecific lipase. Thus, to achieve an appreciable degree of incorporation, it is necessary to use a large excess of fatty acid, for example in concentrated form, and a long reaction time. Concentrates of PUFAs are very expensive. The long reaction time can cause significant oxidation of the PUFAs which are particularly sensitive to oxidation when they are in the form of free fatty acids. Such an oxidation reduces the nutritional value of the PUFAs and may produce degradation compounds which are health hazards.
Furthermore, the use of 1,3-regiospecific lipase produces trisaturated TAGS in excess and also diglycerides. Subsequent enzymatic treatments are required, in particular to remove the trisaturated TAGs in excess from the crude product, which makes the process complicated and expensive.
Finally, the lipid mixture obtained must, in spite of everything, be mixed with other fats in order to correspond to the composition of human milk fat.
SUMMARY OF THE INVENTION
The aim of the invention is to provide a synthetic TAG composition whose composition and structure are close to those of human milk, using a synthesized process for incorporating PUFAs which does not cause significant destructive oxidation of the PUFAs.
The invention therefore relates to a synthetic lipid composition in which the content and the distribution of the fatty acids which mimic those of human milk fat, characterized in that:
it contains less than 2% by weight of free fatty acids,
the fatty acids of the triacylglycerols comprise, by weight:
about 35 to 55% of saturated fatty acids, among which 18 to 36% of palmitic acid, 2 to 40% of caprylic and capric acids, at most 10% of lauric acid and at most 10% of myristic acid,
about 30 to 45% of monounsaturated fatty acids,
about 9 to 22% of polyunsaturated fatty acids, among which less than 2% of long-chain n-6 poly-unsaturated fatty acids comprising arachidonic acid and less than 1% of long-chain n-3 poly-unsaturated fatty acids comprising docosahexaenoic acid and the n-6:n-3 fatty acid ratio is 5:1 to 15:1,
palmitic acid is predominantly at the 2-position of the triacylglycerols and arachidonic and docosahexaenoic acids are distributed between the 1-, 2-and 3-positions of the triacylglycerols.
The AA and DHA acids may be predominantly at the 2-position of the triacylglycerols.
Since it is more specifically intended for consumption by premature babies, the lipid composition according to the invention is such that the caprylic and capric acids preferably represent about 2 to 10% by weight of the fatty acids of the triacylglycerols.
The invention also relates to a process for the preparation of a lipid composition above, characterized by the following successive steps:
1) A mixture of lipids containing a palm oil enriched with palmitic acid, a vegetable oil high in the unsaturated linoleic and alpha-linolenic fatty acids, an oil which is the source of arachidonic acid, an oil which is the source of docosahexaenoic acid, in defined proportions, is non-regio-specifically interesterified in order to obtain the required fatty acid composition with a random distribution of the fatty acid residues between the 1-, 2- and 3-positions of the triacylglycerol,
2) The mixture of step 1) is interesterified with a mixture of free fatty acids predominantly comprising the medium-chain fatty acids and oleic acid, using a 1,3-regiospecific lipase, and
3) The free fatty acids are removed from the product of the reaction of step 2).
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The aim of step 1) is to increase the quantity of P at the 2-position of the TAGs and to incorporate the PUFAs, in particular the LC-PUFAs such as DHA and AA at the 1-, 2- and 3-positions of the TAGs. The starting lipid m4mixture is enriched with palmitic acid, for example with palm stearin so as to have about 40% of P at the 2-position of the TAGs. The non-regiospecific interesterification can take place by the enzymatic route, catalysed by a non-regiospecific lipase, or, preferably by the chemical route, catalysed by a chemical catalyst. By this reaction, the non-random distribution of the fatty acids existing in the natural lipids between the different positions of the TAGs is converted to a random distribution, that is to say that the fatty acids become rearranged equally at the 3 positions. In this first step, the content of P at the 2-position passes to about 42%, which practically corresponds to the entire P present in human milk. If the one at the 1- and 3-positions is taken into account, an excess of P therefore exists compared with human milk.
The PUFA fatty acids, and particularly the LC-PUFAs, undergo the rearrangement reaction in the form of TAGs, which are more stable than mixtures of free fatty acids and with a limited reaction time, at a relatively low temperature and under an inert atmosphere, for example under nitrogen. On the other hand, according to the state of the art, the mixtures of fatty acids intended to serve as lipolysis substrate should first be prepared, which can also cause, in part, their degradation by oxidation.
The lipid mixture which results from the reaction has a significantly improved oxidative stability compared with that of a simple physical mixture of lipids of the same PUFA fatty acid composition. This probably results from the PUFA fatty acid dis
Bertholet Raymond
Ducret Pierre
Fleith Mathilde
Wang Junkuan
Jarvis William R. A.
Kim Vickie
Nestac S.A.
Winston & Strawn
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