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Stanol Ester Composition Stanolester Enthaltende Zusammensetzung Composition Contenant Un Ester De Stanol

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Stanol Ester Composition Stanolester Enthaltende Zusammensetzung Composition Contenant Un Ester De Stanol Europäisches Patentamt *EP000897971B1* (19) European Patent Office Office européen des brevets (11) EP 0 897 971 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C11C 3/12, A23D 9/013, of the grant of the patent: A23D 7/00, C07J 9/00 03.11.2004 Bulletin 2004/45 (21) Application number: 98202586.8 (22) Date of filing: 31.07.1998 (54) Stanol ester composition Stanolester enthaltende Zusammensetzung Composition contenant un ester de stanol (84) Designated Contracting States: • Lievense, Lourus Cornelis BE DE DK ES FI FR GB IE IT NL SE 13270 - 000 Valinhos/SP (BR) (30) Priority: 22.08.1997 EP 97202596 (74) Representative: Van Velzen, Maaike Mathilde et al Unilever N.V., (43) Date of publication of application: Patent Department, 24.02.1999 Bulletin 1999/08 Olivier van Noortlaan 120 3133 AT Vlaardingen (NL) (73) Proprietors: • UNILEVER N.V. (56) References cited: 3000 DK Rotterdam (NL) WO-A-98/01126 WO-A-98/06405 Designated Contracting States: WO-A-98/19556 GB-A- 1 405 346 BE DE DK ES FI FR NL SE US-A- 5 502 045 • UNILEVER PLC London EC4P 4BQ (GB) • PATENT ABSTRACTS OF JAPAN vol. 011, no. Designated Contracting States: 251 (C-440), 14 August 1987 & JP 62 055040 A GB IE (NISSHIN OIL MILLS LTD:THE), 10 March 1987 (72) Inventors: • van Amerongen, Marnix P. 3133 AT Vlaardingen (NL) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 897 971 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 0 897 971 B1 2 Description eral plant materials. Sources are described in, for ex- ample, PCT/EP96/02344. For this invention, a prefer- [0001] The present invention concerns a stanol fatty ence exists for sterols from vegetable oil. acid ester composition, and the use thereof in food prod- [0007] For obtaining the sterolesters before harden- ucts, in particular in fat based food products in amounts 5 ing is carried out, the sterols are esterified with one or sufficient to obtain a blood cholesterol lowering effect if more C2-24 fatty acids. For the purpose of the invention the food product is used according to the common the term C2-24 fatty acid refers to any molecule compris- needs of the consumer. ing a C2-24 main chain and at least one acid group. Al- [0002] Fatty acid esters of phytosterols and/or phyto- though not preferred within the present context the C2-24 stanols are hydrolyzed in the gut and the subsequent 10 main chain may be partially substituted or side chains free phytosterols and/or phytostanols will inhibit the ab- may be present. Preferably, however the C2-24 fatty ac- sorption of cholesterol thereby lowering the blood cho- ids are linear molecules comprising one or two acid lesterol. Free phytosterols and/or phytostanols them- group(s) as endgroup(s). Most preferred are linear C8-22 selves are hardly absorbed. Indications in literature are fatty acids as occur in natural oils. Suitable esterification that phytostanols are absorbed even in a lesser extend 15 conditions are for example described in WO 92/19640. than phytosterols. The use of phytostanols in fat based [0008] Suitable examples of any such fatty acids are food products to lower blood cholesterol could therefore acetic acid, propionic acid, butyric acid, caproic acid, be preferred over the use of phytosterols. caprylic acid, capric acid. Other suitable acids are for [0003] In US-Patent 5,502,045 (Raision Tehtaat Oy example citric acid, lactic acid, oxalic acid and maleic AB) a substance of beta-sitostanol fatty acid ester is de- 20 acid. Preferred are lauric acid, palmitic acid, stearic acid, scribed produced by 1. solvent hardening of beta-sito- arachidic acid, behenic acid, oleic acid, cetoleic acid, sterol followed by 2. esterification of the formed beta- erucic acid, elaidic acid, linoleic acid and linolenic acid. sitostanol with fatty acids. The so formed mixture of be- [0009] Most preferred are the C18 polyunsaturated, ta-sitostanol fatty acid esters can be used as such or monounsaturated or saturated fatty acids like stearic ac- added to a food. 25 id, oleic acid, elaidic, linoleic acid, alpha-linolenic acid [0004] There are several disadvantages to this pro- and gamma-linolenic acid, since after fully hardening of duction method, of which the most severe is that the be- sterolesters comprising these fatty acids, the fatty acid ta-sitosterol should first be solubilized in a solvent (e.g. part will be the saturated stearic acid, which has a neu- ethylacetate, butanol, ethanol) before the hardening of tral effect on blood cholesterol. the sterol can be performed. Because the solubility of 30 [0010] When desired a mixture of fatty acids may be beta-sitosterol, or phytosterols in general, in solvents is used. For example it is possible to use a natural occur- rather limited, the hardening step is relative expensive ring fat or oil as a source of the fatty acid and to carry operation because of high solvent costs and high costs out the esterification via an interesterification reaction. of hardening equipment of relative large volume. More- Most preferred are fatty acid mixtures containing high over, the solvents needs to be recovered after the hard- 35 amounts (>70%) of C18 polyunsaturated, monounsatu- ening process is completed, and suitable locations for rated or saturated fatty acids such as fatty acid mixtures above hardening process will be limited because of en- of sunflower, safflower, rapeseed, linseed, linola and/or vironmental regulations. Furthermore, in a process aim- soybean. ing at the production of a food ingredient, removal of all [0011] The fatty acid ester stanols so obtained are solvents is essential, this making the process even more 40 subject of this invention. These stanol esters, of which expensive. >85%, preferably > 90%, and most preferably >95% are [0005] It has now been found that phytostanol fatty saturated stanol esters which are formed by the hard- acid esters can be suitably prepared by the esterification ening of esterified sterols, will be of a very different na- of phytosterols, followed by hardening of the so formed ture when compared to the stanol esters prepared by phytosterol fatty acid esters. This method has the ad- 45 hardening and subsequent esterification. vantage that no solvents in the hardening step are need- These saturated fatty acid stanol esters were found to ed since the phytosterol-esters are in a liquid form by have stronger structuring properties than stanolesters themselves. Moreover, besides this method is solvent mixtures comprising mainly mono- or poly- unsaturated free and environmental friendly, and thus not requiring fatty acids, due to their higher melting points. By using specific legal admissions, it is also more cost effective 50 the so produced stanolesters with saturated fatty acids, due to the fact that less raw materials, equipment and the amount of hardstock required to make a spreadable labour is required. In another method, the stanol fatty product out of above mentioned liquid oils can be more acid esters are prepared by hardening phytosterol fatty reduced than with stanolesters mixtures comprising acid esters or a mixture thereof. mainly mono- or polyunsaturated fatty acids, thereby [0006] Where in this application sterols are men- 55 potentially optimizing the amount of PUFA rich glycer- tioned, phytosterols (4-desmethylsterols, 4-monometh- ides in the product further, and thereby compensating ylsterols and 4,4'-dimethylsterols, and/or mixtures the saturated fatty acid part of the stanol ester mixture thereof) are meant. These sterols can be found in sev- applied in the product. 2 3 EP 0 897 971 B1 4 [0012] The stanol (saturated) fatty acid ester (mixture) preferred of at least 5 wt.%, with a further preference for of this invention may still comprise some unhardened at least 7 wt.%. and/or unesterified sterols and/or sterol esters. It is pre- [0018] The preparation of the fat based food products ferred, however, that the stanol ester mixture of the in- comprising the saturated stanol fatty acid esters of the vention comprises at least 85% of the stanol (saturated) 5 invention can be carried out in any suitable manner com- fatty acid esters, and preferably at least 90%, with a monly known. Suitably, the stanol esters, which will of- most preferred embodiment being found in 95 to about ten be a mixture of different stanol esters, can be added 100% being stanol (saturated) fatty acid esters. The in- and dissolved to the fat prior to combining with the aque- vention concerns stanol fatty acid ester compositions ous phase of the product to be prepared. comprising at least 85% of stanol fatty acid esters in 10 [0019] In a preferred embodiment, the food product is which at least 85% of the fatty acid groups are saturated. a yellow fat spread comprising 0 to 80% fat and at least [0013] Also subject of the invention are food products, 1 wt.%, preferably at least 2 wt.% and more preferably in particular fat based food products, comprising the sta- at least 5 wt% stanol equivalents (present as stanol es- nol (saturated) fatty acid ester (mixtures) in all embodi- ters prepared according to the invention). In its most pre- ments set forth above. It is preferred that the food prod- 15 ferred embodiment, the amount of stanol equivalents is uct comprises at least 1%, and preferably at least 2% at least 5%, with optimal results found when the amount and more preferably at least 5% stanol equivalents of stanol is in the range of 7-15%.
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