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EP2099319A1 - Procédé de préparation de formulations de stérol - Google Patents

Procédé de préparation de formulations de stérol

Info

Publication number
EP2099319A1
EP2099319A1 EP07856258A EP07856258A EP2099319A1 EP 2099319 A1 EP2099319 A1 EP 2099319A1 EP 07856258 A EP07856258 A EP 07856258A EP 07856258 A EP07856258 A EP 07856258A EP 2099319 A1 EP2099319 A1 EP 2099319A1
Authority
EP
European Patent Office
Prior art keywords
sterol
stanol
wet grinding
particle size
sterolformulierun
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07856258A
Other languages
German (de)
English (en)
Inventor
Peter Horlacher
Dieter Hietsch
Jörg SCHWARZER
Bernd Jenzer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP07856258A priority Critical patent/EP2099319A1/fr
Publication of EP2099319A1 publication Critical patent/EP2099319A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/20—Natural extracts
    • A23V2250/21—Plant extracts
    • A23V2250/2136—Phytosterols, phytostanols

Definitions

  • the invention is in the field of foodstuffs and relates to a process for the preparation of readily wettable phytosterol-containing formulations, the preparations prepared by this process and products, in particular foods, which contain these formulations.
  • the international application WO 2005/074717 AX also uses a type of protective colloid by embedding sterols in a matrix containing proteins and carbohydrates.
  • the total content of sterols in the formulation is low due to the high proportion of excipients.
  • a further process for producing a sterol dispersion, in which the particle size distribution of the sterols is from 0.1 to 30 ⁇ m, is taken from International Applications WO 03/105611 and WO 2005/049037.
  • micronization is common sterol particles alone are not sufficient to achieve good incorporability.
  • bioavailability of the finely dispersed particles can be improved by increasing the surface area, it is precisely the micronized particles that are poorly wettable, which aggregate easily and mostly float on aqueous surfaces.
  • the ground sterol can only be dispersed in a beverage using special methods, which requires intensive mixing. However, these devices are usually not available to the end user of food manufacturers.
  • a possible method for the preparation of sterol-containing microparticles can be found in the European patent EP 1148793 Bl. It is based on a high-energy homo- genisation. However, a powder produced on the basis of aqueous suspension agents has insufficient homogeneity and is difficult to redisperse.
  • the disadvantage of many sterol-containing powder formulations is the agglomeration behavior of the free sterols during storage. During storage, especially when stored under pressure, strong caking or clumping is observed, the solid, uncontrolled agglomerates must be crushed again in order to be processed.
  • the invention relates to a wet grinding process for the preparation of well-wettable Sterolformulleiteren comprising: a) an additive selected from the group consisting of proteins, proteinaceous excipients, carbohydrates, cellulose derivatives, sugar alcohols, fruit concentrates and vegetable concentrates in water or an aqueous Dissolves or disperses suspension medium b) adds to this solution / dispersion sterol and / or stanol particles with an average particle size of at least 1 mm, c) homogenizes the resulting dispersion in a mill operating according to the rotor-stator principle and comminuted, and d) optionally subsequently drying, with the proviso that the sterol and / or stanol particles are present in the final formulation in a particle size distribution with a D9 ö % of at most 50 microns.
  • the inventive method makes it possible to produce powder with free unesterified sterols and stanols, which allow easy further processing of the lipophilic drugs without much equipment and at room temperature in food, especially drinks.
  • the powder has a low tendency to agglomerate and thus good flow properties. It is characterized by a good homogeneity and can be further processed due to its improved wettability without great technical effort, with a homogeneous distribution in the final formulation is achieved quickly.
  • the coating of the steroid surface with the hydrophilic additives decisively improves the organoleptic properties and the sensor technology.
  • the coated powder does not stick to teeth and oral mucosa, so that the unpleasant Stering taste, which leads to significant loss of taste in the active ingredient-containing foods is completely suppressed.
  • hydrophilic additives such as proteins, protein-containing auxiliaries, carbohydrates, sugar alcohols, fruit concentrates and vegetable concentrates not only improves solubilization properties and dispersing properties, but surprisingly, these powders also exhibit an increased storage stability compared to pure ground sterols, which have a high agglomeration tendency.
  • the process makes it possible to dispense with the processing of unesterified sterols and stanols to organic solvents or heating of the formulation and despite the aqueous medium no emulsifiers with high surface activity specifically of the type of lecithins, monoglycerides, diglycerides, polysorbates, sodium stearyl lactylate, glycerol monostearate, Use lactic acid esters and polyglycerol esters.
  • the low emulsifier properties of the hydrophilizing auxiliaries, in particular the caseinates, the milk powder or the gum arabic, are sufficient to ensure the homogeneity of the powder produced and easy redispersibility and processability.
  • the elimination of further emulsifiers simplifies the further processing by reducing possible incompatibilities with other food ingredients and reduces the occurrence of incompatibilities with the consumer.
  • a particular advantage of the method is the implementation of milling and coating in one operation.
  • the application of the wet grinding method for comminuting the sterol particles avoids the high risk of powder explosions.
  • the particle size of the sterols and / or stanols used initially is relatively large, on the one hand to avoid powder explosions and on the other hand to ensure good handling. So can finished prills, the one have very high storage stability can be used.
  • the average particle sizes are over 1 mm. In this size, the particle size determination is carried out by a conventional sieve analysis.
  • the sterol and / or stanol particles in the final formulation are present after wet grinding in a particle size distribution with a Dgo% of at most 50 .mu.m, preferably at most 40 .mu.m and more preferably at most 30 .mu.m.
  • the particle size distribution was determined using a device from Beckman Coulter, type LS 230 and calculated as the volume distribution. The measurement was carried out in aqueous suspension.
  • the time required for grinding which leads to this degree of comminution, should be a maximum of 2 hours, preferably a maximum of 1 hour.
  • the process usually runs at ⁇ 2-3 bar ( ⁇ 43.5 psi). And it can also pasteuse to puncture-proof masses are processed.
  • the mill to be used is based on a rotor-stator principle. Tooth colloid mills, but also Ultra-Turrax, corundum disc mills, perforated disc mills or annular gap ball mills, in which the balls are in the gap between the rotor and the housing, are suitable for the erf ⁇ ndungswashe method. Dental colloid mills have proved to be particularly advantageous. Based on the observation that the energy input during grinding must have a degree that on the one hand sufficient crushing without extreme heating of the ground material allows and on the other hand to lead to a low charge of the particles, these mills have proven particularly useful.
  • the expenditure on equipment of the manufacturing apparatus according to the invention is thus very low. On a cooling of the ground material during milling can be dispensed with, the thermal load of the material is low. In addition, the risk of dust explosions is extremely reduced by the use of wet grinding.
  • the aqueous dispersions have concentrations of sterols and stanols of at least 20% by weight, preferably at least 30% by weight and more preferably at least 40% by weight and especially at least 50% by weight, based on the total weight of the dispersion.
  • these dispersions are dried.
  • the conventional drying methods such as vacuum drying or spray drying offer. Since the additives are used only for hydrophilization and the surface of the sterols are coated with it, the total content of sterols in the powders is very high.
  • the powder resulting after drying even contains at least 75% by weight, more preferably at least 85% by weight and in particular at least 90% by weight, of sterols and / or stanols, based on the weight of the dried powders.
  • Powders with sterol / stanol contents of at least 90% which can be produced by this method, are therefore comparable to ground or micronised sterols / stanols, even from the sterol content.
  • the powders according to the invention are distinguished by the following advantages: they are more free-flowing and can easily be dispersed in water without the use of high shear forces. Processing companies such as dairies can thus use their standard stirrer for incorporation into food.
  • the good water dispersibility is surprising inasmuch as the amount of carrier (maximum 10%) with a particle size of at most 50 ⁇ m is insufficient to cover all particles (for example: is required for a 50 ⁇ m particle (surface of 0.0079 mmVparticle 63% support in order to obtain a 10 ⁇ m thick cladding, with 30 ⁇ m particles already being around 78% of support material.
  • the powder can be stored without clumping and caking.
  • Ground sterols are very prone to caking. This leads to the fact that after prolonged storage a block is obtained, which one must crush by strong expenditure of force, before it can be used. Furthermore, the storage becomes safer due to the increased minimum ignition energy. This has a very low value of 1 mJ> MZE ⁇ 3 mJ for the ground sterols and stanols.
  • the preparations according to the invention are significantly safer here: 3 mJ> MZE ⁇ 10 mJ.
  • the sterol content of the final formulation depends on the amount of hydrophilic additive used.
  • the powders have the advantage that on the one hand, the content of active substance is much greater, the storage stability is significantly improved and - especially in aqueous media - the microbiological stability is significantly increased. Due to the low proportion of carriers, only minor changes and influences on the final formulation are to be expected. This is in contrast to a dispersion where the medi- um / matrix (oil, milk, fat cream) takes a non-negligible influence due to the high amounts of matrix.
  • the sterol-containing formulations prepared by these methods can be easily incorporated into foods, in particular milk, milk drinks, whey and yoghurt drinks, margarines, fruit juices, fruit juice mixtures, fruit juice drinks, vegetable juices, carbonated and non-carbonated beverages, soy milk beverages or high-protein liquid diet replacement drinks, and fermented milk preparations.
  • Yogurt, drinking yoghurt, or cheese preparations but also be incorporated into pharmaceutical preparations.
  • fruit or vegetable concentrate can be previously dispersed in the suspension medium and thus diluted (step a)).
  • fruit or vegetable concentrate can be used directly as a suspending agent for the sterols and / or stanols, so that only the sterols and / or stanols are added to the concentrates and the resulting dispersion is comminuted and homogenized in the rotor-stator mill. Further additives listed in step a) are then not required.
  • the resulting formulations have a high content of sterols and / or stanols. As a rule, they have a yield point, ie they are solid, but they can be re-liquefied by shearing so that they can be further processed directly into final foodstuff formulations by simple means.
  • a further subject of the invention is therefore fruit and vegetable concentrates containing at least 1% by weight, preferably at least 5% by weight and more preferably at least 15% by weight of sterols and / or stanols, based on the concentrates.
  • These concentrates have a water content of at most 85% by weight, preferably at most 75% by weight and particularly preferably at most 65%, in order to have the consistency which is advantageous for further processing.
  • the sterol and / or stanol particles contained therein have a particle size distribution with a Dgo% of at most 50 ⁇ m, preferably not more than 40 ⁇ m and particularly preferably not more than 30 ⁇ m.
  • Another object of the invention relates to food preparations containing the sterol / stanol formulations of said composition. They are preferably used in beverages and milk products, which then contain 0.1 to 50 wt .-%, preferably 1 to 20 wt .-% of the pulverulent coated preparations based on the total weight of the food. Sterol and / or stanol
  • sterols derived from plants and vegetable raw materials so-called phytosterols and phytostanols are used.
  • Known examples are ergosterol, brassicasterol, campesterol, avenasterol, desmosterol, clionasterol, stigmasterol, poriferasterol, chalinosterol, sitosterol and mixtures thereof, among which ⁇ -sitosterol and campesterol are preferably used.
  • the hydrogenated saturated forms of the sterols, the so-called stanols are among the compounds used; here too, ⁇ -sitostanol and campestanol are preferred.
  • Soya beans, canola, palm kernels, corn, coconut, oilseed rape, cane, sunflower, olive, cotton, soy, peanut and tall oil products are among the sources of vegetable sources.
  • Milk powder and / or whey powder and / or casein and / or caseinates are preferably used as protein-containing auxiliaries and proteins.
  • Milk powder such as commercial whole milk and skimmed milk powder, which have been obtained from the respective milk qualities by drying, are particularly suitable. They can be used in mixtures with other proteins or as the sole carrier. If further proteins are added or proteins are used as a carrier instead of the milk powder, these are understood as meaning isolated proteins which are obtained from natural animal and vegetable sources and are added during the preparation of the pulverulent preparations.
  • Possible sources of proteins are plants such as wheat, soy, lupine, corn or sources of animal origin such as eggs or milk.
  • Skim milk powder is particularly preferred for the purposes of the present invention, since it has sufficient hydrophilizing properties without at the same time to show the disadvantages of such Anlagenemulgatoren described above, which are otherwise usually used especially for the production of beverages and dairy products, especially fermentation products such as yogurt.
  • skim milk powder best covers the typical unpleasant sterol taste, and formulations with this additive have improved sensory properties over other excipients.
  • the compounds used as carbohydrates include all food-grade polyols and monosaccharides, such as, for example, glucose, sucrose, fructose, trehalose, Maltose, maltodextrin, cyclodextrin, invert sugar, palatinose, lactose, guar gum, xanthan, pectins, starch, starch derivatives and modified starch, alginates, carrageenans, wheat gluten and gum arabic.
  • Gum arabic, galactomannans such as guar gum, xanthan, starch and starch derivatives and modified starches (OSA starch) are preferably used as the carbohydrate, with gum arabic being particularly preferred.
  • the preparations according to the invention may contain antioxidants, preservatives and flow improvers.
  • antioxidants or preservatives are tocopherols, lecithins, ascorbic acid, parabens, butylhydroxytoluene or anisole, sorbic acid or benzoic acid and salts thereof.
  • Tocopherols are preferably used as antioxidants.
  • silica may be used as a flow regulator and improver.
  • emulsifiers selected from the group consisting of lecithins, monoglycerides, diglycerides, polysorbates, sodium stearyl lactylate, glycerol monostearate, lactic acid esters and polyglycerol esters.
  • a portion of the dispersion thus obtained was dried in vacuo at 60 ° / 1 mbar. This was followed by a measurement of the particle size distribution of the vacuum-dried powder by laser diffractometry (Beckman Coulter, type LS 320). This gave a Dgoo / ,, of 25 microns.
  • the powders thus obtained were dispersed in milk and water as compared to ground sterols of comparable particle size distribution.
  • about 250 ml of the zu placed in a beaker and stirred about 100 rpm.
  • To the stirred liquid was added 2.5 g of the respective powder and the dispersing behavior was evaluated.
  • the coated sterol settled (C 18 °) disperse very well in cold (15 0 C) and warm (60 ° C) water as well as in milk, while the untreated sterol was poorly dispersed and lay due to the hydrophobic surface on the liquid surface.
  • the resulting powders are characterized by improved flowability, better stirrability in water and higher bulk density in comparison to customary finely ground sterols.
  • the dried products have a sterol content of over 90%. In Example 1, the sterol content of the dried powder is 93%.
  • the powders can be introduced into aqueous systems such as water, juices, milk etc. simply by stirring them
  • the dispersions have a flow limit, are easy to stir and can easily be added to aqueous systems such as cold water, juices, milk, etc.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Botany (AREA)
  • Molecular Biology (AREA)
  • Mycology (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicinal Preparation (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Grain Derivatives (AREA)

Abstract

La présente invention concerne un procédé de broyage humide destiné à la préparation de formulations de stérol facilement mouillables, qui consiste à : a) dissoudre ou disperser dans de l'eau ou un milieu de suspension aqueux, un additif choisi dans le groupe formé par des protéines, des substances secondaires contenant des protéines, des hydrates de carbone, des dérivés de cellulose, des alcools de sucre, des concentrés de fruit et des concentrés de légumes; b) ajouter à cette solution / dispersion des particules de stérol et/ou de stanol ayant une granulométrie moyenne d'au moins 1 mm; c) homogénéiser et fragmenter la dispersion ainsi formée dans un moulin qui fonctionne selon le principe rotor-stator; et d) éventuellement l'assécher, à la condition que les particules de stérol et/ou de stanol soient présentes dans la formulation finale en une distribution de granulométrie avec un D90% au maximum de 50 μm. Les formulations contenant du stérol obtenues au moyen de ce procédé peuvent, grâce à leur bonne mouillabilité, facilement être intégrées à des aliments, sans entraîner de frais importants liés à la technique, et ont de bonnes propriétés organoleptiques et sensorielles en particulier dans des boissons et des produits laitiers.
EP07856258A 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol Withdrawn EP2099319A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07856258A EP2099319A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06025003A EP1929884A1 (fr) 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles
EP07856258A EP2099319A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol
PCT/EP2007/010229 WO2008067923A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol

Publications (1)

Publication Number Publication Date
EP2099319A1 true EP2099319A1 (fr) 2009-09-16

Family

ID=38109672

Family Applications (2)

Application Number Title Priority Date Filing Date
EP06025003A Withdrawn EP1929884A1 (fr) 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles
EP07856258A Withdrawn EP2099319A1 (fr) 2006-12-04 2007-11-24 Procédé de préparation de formulations de stérol

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP06025003A Withdrawn EP1929884A1 (fr) 2006-12-04 2006-12-04 Procédé de préparation des compositions de steroles

Country Status (5)

Country Link
US (2) US8414945B2 (fr)
EP (2) EP1929884A1 (fr)
JP (2) JP5611595B2 (fr)
AU (1) AU2007327973B2 (fr)
WO (1) WO2008067923A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018132419A1 (fr) * 2017-01-11 2018-07-19 Empire Technology Development Llc Produits à base de résidus de déchets de noix de coco imprégnés de tréhalose
US11191289B2 (en) 2018-04-30 2021-12-07 Kraft Foods Group Brands Llc Spoonable smoothie and methods of production thereof
JP2020058287A (ja) * 2018-10-10 2020-04-16 ヤンマー株式会社 米ゲル製造システム及び米ゲル製造方法
CN115969036B (zh) * 2023-01-10 2024-05-07 丰益油脂科技有限公司 植物甾醇颗粒物及其制备方法

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3881005A (en) * 1973-08-13 1975-04-29 Lilly Co Eli Pharmaceutical dispersible powder of sitosterols and a method for the preparation thereof
FI105887B (fi) * 1996-09-27 2000-10-31 Suomen Sokeri Oy Elintarvike- ja terapeuttisiin sovelluksiin käyttökelpoiset, kasvisterolia sisältävät tuotteet, menetelmä niiden valmistamiseksi ja niiden käyttö
FI108110B (fi) * 1997-06-13 2001-11-30 Danisco Finland Oy Elintarvike- ja eläinravitsemusalalla käyttökelpoinen esiseos, menetelmä sen valmistamiseksi ja sen käyttö
US6423363B1 (en) 1997-08-22 2002-07-23 Lipton, Division Of Conopco, Inc. Aqueous dispersion
AU771960B2 (en) 1998-06-05 2004-04-08 Forbes Medi-Tech Inc. Compositions comprising phytosterol and/or phytostanol having enhanced solubility and dispersability
US6113972A (en) * 1998-12-03 2000-09-05 Monsanto Co. Phytosterol protein complex
WO2000045648A1 (fr) * 1999-02-03 2000-08-10 Forbes Medi-Tech Inc. Procede de preparation de microparticules constituees de phytosterols ou de phytostanols
US6391370B1 (en) * 1999-11-12 2002-05-21 Kraft Foods, Inc. Micromilling plant sterols and emulsifiers
US6677327B1 (en) 1999-11-24 2004-01-13 Archer-Daniels-Midland Company Phytosterol and phytostanol compositions
US20030165572A1 (en) * 2000-09-01 2003-09-04 Nicolas Auriou Water-dispersible encapsulated sterols
US20040047965A1 (en) * 2001-03-05 2004-03-11 Rudolf Haindl Milk product and process for its prouduction
CA2481384A1 (fr) 2002-04-10 2003-10-23 Cargill, Incorporated Compositions d'esters de steryle aqueuses dispersibles
US7306819B2 (en) * 2002-06-12 2007-12-11 The Coca-Cola Company Beverages containing plant sterols
PT1549159E (pt) 2002-06-12 2008-12-23 Coca Cola Co Bebidas contendo esteróis vegetais
JP2004075541A (ja) * 2002-08-09 2004-03-11 Nof Corp ステロール類含有粉末組成物、圧縮成形物、製造方法及び用途
DE10253111A1 (de) 2002-11-13 2004-05-27 Basf Ag Pulverförmige Phytosterol-Formulierungen
AU2003304550B2 (en) * 2003-10-24 2011-02-10 The Coca-Cola Company Process for preparing phytosterol dispersions for application in beverages
WO2005074717A1 (fr) 2004-01-30 2005-08-18 Unilever N.V. Matiere particulaire comportant des phytosterols et des compositions alimentaires comprenant une telle matiere cremeuse
US20050175672A1 (en) * 2004-02-10 2005-08-11 Kluetz Michael D. Particulate plant sterol compositions
US8968768B2 (en) * 2004-03-29 2015-03-03 Wyeth Llc Phytosterol nutritional supplements
US20060034934A1 (en) * 2004-08-13 2006-02-16 Deguise Matthew L Agglomeration of sterol particles
TW200635518A (en) * 2004-11-17 2006-10-16 San Ei Gen Ffi Inc Sitosterol compound-containing composition and process for producing the same
US20060121174A1 (en) * 2004-12-08 2006-06-08 Franke William C Compositions and methods to deliver consumable water dispersible phytosterols
US8309156B2 (en) * 2005-12-20 2012-11-13 Pharmachem Laboratories, Inc. Compositions comprising one or more phytosterols and/or phytostanols, or derivatives thereof, and high HLB emulsifiers
CA2673010A1 (fr) * 2005-12-20 2007-06-28 Forbes Medi-Tech Inc. Compositions comprenant un ou plusieurs phytosterols et/ou phytostanols, ou des derives de de ceux-ci, et des emulsifiants a rapport hlb eleve
US20110223312A1 (en) * 2009-11-30 2011-09-15 Daniel Perlman Triglyceride-encapsulated phytosterol microparticles dispersed in beverages

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2008067923A1 *

Also Published As

Publication number Publication date
JP5611595B2 (ja) 2014-10-22
EP1929884A1 (fr) 2008-06-11
US20100068367A1 (en) 2010-03-18
JP2014076054A (ja) 2014-05-01
WO2008067923A1 (fr) 2008-06-12
AU2007327973B2 (en) 2013-05-23
JP2010511391A (ja) 2010-04-15
US8414945B2 (en) 2013-04-09
AU2007327973A1 (en) 2008-06-12
US20130216678A1 (en) 2013-08-22

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