Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Fat or oil is basic ingredient other than butter in emulsion...
Reexamination Certificate
1998-08-18
2001-05-15
Paden, Carolyn (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Fat or oil is basic ingredient other than butter in emulsion...
C426S602000, C426S603000, C552S544000, C552S545000
Reexamination Certificate
active
06231915
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention concerns a method for the production of stanol fatty acid esters, a stanol fatty acid ester composition, and the use thereof in food products, in particular in fat based food products in amounts sufficient to obtain a blood cholesterol lowering effect if the food product is used according to the common needs of the consumer.
Fatty acid esters of phytosterols and/or phytostanols are hydrolysed in the gut and the subsequent free phytosterols and/or phytostanols will inhibit the absorption of cholesterol thereby lowering the blood cholesterol. Free phytosterols and/or phytostanols themselves are hardly absorbed. Indications in literature are that phytostanols are absorbed even in a lesser extend than phytosterols. The use of phytostanols in fat based food products to lower blood cholesterol could therefore be preferred over the use of phytosterols.
In U.S. Pat. No. 5,502,045 (Raision Tehtaat Oy AB) a substance of beta-sitostanol fatty acid ester is described produced by 1. solvent hardening of beta-sitosterol followed by 2. esterification of the formed beta-sitostanol with fatty acids. The so formed mixture of beta-sitostanol fatty acid esters can be used as such or added to a food.
There are several disadvantages to this production method, of which the most severe is that the beta-sitosterol should first be solubilized in a solvent (e.g. ethylacetate, butanol, ethanol) before the hardening of the sterol can be performed. Because the solubility of beta-sitosterol, or phytosterols in general, in solvents is rather limited, the hardening step is a relatively expensive operation because of high solvent costs and high costs of hardening equipment of relatively large volume. Moreover, the solvents need to be recovered after the hardening process is completed, and suitable locations for above hardening process will be limited because of environmental regulations. Furthermore, in a process aiming at the production of a food ingredient, removal of all solvents is essential, this making the process even more expensive.
It has been observed that the stability of fat based food products diminishes by the addition of sterols and stanols thereto, in particular when the sterols/stanols are used at higher levels. As sterols and stanols are not very soluble in fat large crystals thereof are found in the products prepared with these sterols or stanols. For example, very serious crystal formation is observed at 3-4% sterol levels On the other hand, however, the use of these higher levels is often required to obtain the significant cholesterol reduction level that is desired.
It is well known that by esterification of sterols/stanols with fatty acids, the solubility can be increased. However, a disadvantage of esterification is that this decreases the efficacy of the sterol/stanol compounds to lower the blood cholesterol level. Another disadvantage found in the use of sterol/stanol fatty acid esters is that the absorption of lipophilic micronutrients (like beta-carotene) decreases (Gyling HK et al (1996) Circulation 6: I-578).
Another disadvantage found with the esterification of sterols/stanols is found in the production thereof, requiring long processing times and/or high processing costs.
SUMMARY OF THE INVENTION
The disadvantages indicated above were found to be reduced with the present invention, which concerns a process for the production of a stanol and stanol fatty acid ester mixture, by esterification of phytosterols with a source for fatty acid moieties in such a way that the degree of esterification of the sterols is in the range of 40%-85%, and subsequent hardening of the so obtained sterol/sterol fatty acid ester mixture. Preferably, the degree of esterification is in the range of 50-85%, more preferably in the range of 55-80%, and most preferably in the range of 60-70%. This process allows a preparation of mixtures of stanols and stanol fatty acid esters without the presence of a solvent needed in any of the process steps. Sources for fatty acid moieties, are the known compounds, normally applied in esterification reactions. Preferred sources are free fatty acids and triglycerides.
This invention allows that a significant cost reduction can be achieved, as the amount of the relatively expensive sterols used as the starting material can be reduced without a decrease of comparable blood cholesterol lowering efficacy of the end product, whereas a further reduction of costs is obtained in the time and processing reduction of the esterification process of the sterols. By partial esterification of the sterols and subsequent hardening of the sterol/sterol ester mixture so obtained no solvents in the hardening step are needed since the sterolester mixture is in a liquid state. Using such a solvent free production method, which is more environmental friendly, and does not require specific legal admissions, is also more cost effective due to the fact that less raw materials, equipment and labour is required.
Hence, advantages are found in minimization of possible negative side effects and optimization of efficacy, quality (solubility) and production costs.
Where in this application sterols are mentioned, phytosterols (4-desmethylsterols, 4-monomethylsterols and 4,4′-dimethylsterols, and/or mixtures thereof) are meant. When stanols are mentioned the stanol analogous of above molecules and mixtures thereof are meant.
For obtaining the sterolester mixture before hardening is carried out, the sterols are esterified with a source for one or more C2-24 fatty acids moieties to an esterification degree in the range of 40-85%, more preferably in the range of 50-80% and most preferably in the range of 60-70%. For the purpose of the invention the source for fatty acid moieties can be indicated with the term C2-24 fatty acid and this refers to any molecule comprising a C2-24 main chain and at least one acid group. Although not preferred within the present context the C2-24 main chain may be partially substituted or side chains may be present. Preferably, however the C2-24 fatty acids are linear molecules comprising one or two acid group(s) as endgroup(s). Most preferred are linear C8-22 fatty acids as occur in natural oils. Suitable esterification conditions are for example described in WO 92/19640.
Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid. Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid. Preferred are lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
Most preferred are the C18 polyunsaturated, monounsaturated or saturated fatty acids like stearic acid, oleic acid, elaidic, linoleic acid, alpha-linolenic acid and gamma-linolenic acid, since after fully hardening of sterolesters comprising these fatty acids, the fatty acid part will be the saturated stearic acid, which has a neutral effect on blood cholesterol.
When desired a mixture of fatty acids may be used. It is also possible to use a natural occurring fat or oil as a source of the fatty acid moieties and to carry out the esterification via an interesterification reaction herewith. Most preferred are fatty acid mixtures containing high amounts (>70%) of C18 polyunsaturated, monounsaturated or saturated fatty acids such as fatty acid mixtures of sunflower, safflower, rapeseed, linseed, linola and/or soybean.
The invention further concerns the stanol and stanol fatty acid ester mixture so produced. Also claimed are stanol and stanol fatty acid esters mixtures wherein the fatty acid groups of the stanol fatty acid esters are substantially saturated fatty acid groups, and preferably, >85% are saturated, more preferably >90%, and most preferably >95% are saturated.
The invention further describes food products comprising such a mixture. The food products of the invention comprise at least 1% of stanol equivalents (present as free stanols and stanol fat
Lievense Lourus Cornelis
van Amerongen Marnix P.
Lipton division of Conopco, Inc.
McGowan, Jr. Gerard J.
Paden Carolyn
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