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
2001-09-20
2003-05-13
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...
C426S601000, C552S544000
Reexamination Certificate
active
06562395
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to olive oil based products, based on especially higher grades of olive oils like virgin olive oils, containing plant stanol esters and/or plant sterol esters and methods for preparing such olive oil based products, as well as certain plant stanol and/or sterol esters usable for the preparation of the olive oil based product.
Plant sterols are a group of compounds structurally very similar to cholesterol. The plant sterols occurring most frequently in nature are sitosterol, campesterol and stigmasterol. Vegetable oils and fats are the main source of plant sterols in our diet. In vegetable oils a major part of the sterols exists as fatty acid esters. Saturated plant sterols such as sitostanol and campestanol are present in our diet in small amounts. Daily intake of total stanols in the Finnish diet has been estimated to 30-80 mg/day. However, tall oil sterols contain 10-20% of plant stanols (mainly sitostanol and campestanol). Plant stanols can also be produced by hydrogenation to remove the double bond in corresponding plant sterols.
In recent years, much interest has been focused on the cholesterol-lowering properties of plant stanols and sterols with already many plant stanol or sterol enriched products such as margarines, salad dressings, bars and yogurts commercially available. Based on recent studies, a daily intake of 2-3 g plant stanols or sterols significantly reduces serum LDL cholesterol levels even when used as part of healthy recommended diets. Plant stanol and sterol enriched foods provide an enhanced dietary approach for lowering elevated serum total and LDL cholesterol levels. Enrichment of staple foods with plant stanols and/or sterols in their fatty acid ester forms is possible without compromising on taste or mouthfeel. Based on the cholesterol lowering efficacy and the fact that plant stanols are virtually unabsorbable, plant stanols are more preferable, but also blends of plant stanols and sterols or plant sterols alone can be used.
The best benefit from using plant stanols and/or sterols for lowering elevated serum total and LDL cholesterol levels is obtained when enriching staple foods. For example, in the northern part of Europe, margarine and spreads are very suitable food products for such enrichment, but for the southern part of Europe other staple food candidates need to be found. In this region, olive oil is a staple food of major importance. In addition, olive oil consumption is increasing also in other parts of the world due to the health reputation and the flavour of higher grades of olive oils. Olive oil contains naturally very low levels of plant sterols (typically <0.2 g/100 g oil). In addition higher grade olive oils, such as virgin olive oils, contain quite high amounts of squalene, a precursor of cholesterol. The content of squalene varies, but extra virgin olive oil typically contains about 300 mg/100 g oil. Dietary squalene has been shown to increase serum cholesterol levels in man. Such an effect on serum total and LDL cholesterol levels may be counteracted by plant stanols and/or sterols. Therefore, there is clearly a need to make commercially available higher grade olive oils enriched with plant stanols and/or sterols, and to ensure that such olive oils have similar properties as normally used olive oils.
Virgin olive oils should remain clear when stored at 20° C. for 24 hours. Typically, higher grades of olive oils, such as virgin olive oils, become cloudy with even clear crystallization occuring when stored for a prolonged time at refrigerator temperatures. An olive oil enriched with plant stanols and/or sterols should avoid cloudiness.
For the large-scale production of plant stanol and/or sterol esters, normally common vegetable oils or commercially available edible oils with modified fatty acid compositions are used. Enrichment of higher grades of olive oils, such as virgin olive oils, with plant stanol and/or sterol esters with fatty acids derived from such commercially available vegetable oils or their blends further enhances the precipitation of higher melting lipids at room temperatures and below. The formed crystals do not normally dissolve, even after prolonged storage at room temperatures. This problem cannot be solved, even by using the esterification of stanol and/or sterol fatty acids derived from currently commercially available vegetable oils with high levels of polyunsaturated fatty acids and low levels of saturated fatty acids, such as low saturated soybean oil (PUFA: 67 weight-%, SAFA: 7,9 weight-%), sunflower oil (PUFA: 64 weight-%, SAFA: 12 weight-%) or linola oil (PUFA: 70 weight-%, SAFA 11 weight-%).
U.S. Pat. No. 5,080,139 describes a method for refining virgin olive oil, in which the virgin olive oil is microfiltrated over a microfilter at temperatures from 15 to 35° C. to obtain a virgin olive oil staying bright when subjected to a cold test at 0° C. for 24 hours.
U.S. Pat. No. 3,751,569 describes clear cooking and salad oils having hypocholesterolemic properties. Into the liquid glyceride base oil is mixed 0.5-10 weight-% (calculated as free sterols) of a sterol fatty acid ester. The fatty acid moiety is defined as a C
1-12
saturated monocarboxylic acid moiety or an unsaturated fatty acid with up to 24 carbon atoms. In one embodiment, the sterol fatty acid ester is prepared by perchloric acid catalyzed esterification of commercially-available free sterols with monocarboxylic acid anhydrides. The sterol fatty acid ester is added in an amount small enough to prevent precipitation at refrigerator temperatures. In the exemplified embodiment, the cooking or salad oil was prepared by dissolving a liquid glyceride base oil and a plant sterol monocarboxylic acid ester in a mutual solvent (such as hexane or diethyl ether) and evaporating the solvent. The solubility of different fatty acid esters of plant sterol in triolein are also presented, showing very low solubility for C
12
(0.6%) and C
16
(0.1%) saturated fatty acid plant sterol esters. The process and product disclosed in the '569 patent suffers from at least two drawbacks. First, the use of fatty acids prepared from individual commercially-available free sterols is neither practical nor economical, as these starting products are quite expensive. Second, the perchloric acid catalyzed esterification process used in the '569 patent is not a food grade process, as residual chloride remains in the product. Thus, the '569 patent is not suitable for commercial applications.
GB Patent 1 405 346 teaches a process by which free sterols naturally contained in edible oils and fats are converted to fatty acid esters via an interesterification process. In addition, in Example 2 a method for producing vegetable oils with elevated sterol ester contents is described. However, the method taught is based on the interesterification of the entire oil blend, which based on physical properties cannot be executed for higher grades of commercial olive oils, such as virgin olive oils.
SUMMARY OF THE INVENTION
Saturation of a plant sterol blend to a corresponding plant stanol blend causes marked differences in the melting properties of the corresponding sterol/stanol esters with the same fatty acid composition. For example, vegetable oil based sterol ester with low erucic acid content, rapeseed oil fatty acids and corresponding stanol fatty acid ester showed the following amounts of solid fat contents (weight-% of total fat) at different temperatures as measured by NMR-technique:
10° C.
20° C.
30° C.
35° C.
40° C.
plant sterol
40.5
11.6
3.5
1.7
1.1
plant stanol
82.3
70.2
34.9
9.4
5.2.
The physical properties of stanol and/or sterol fatty acid esters can be tailor-made by changing the fatty acid composition of the fatty acid ester or by using different ratios of plant stanols and sterols in the ester.
In the present invention the problem with the precipitation/crystallisation of higher melting lipids in higher grade olive oils is overcome by dissolving plant stanol and/or sterol fatty acid esters with
Orte Juha
Wester Ingmar
Arent Fox Kintner & Plotkin & Kahn, PLLC
Paden Carolyn
Raisio Benecol Ltd.
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