WO2002065859A1 - Emulsions and aqueous dispersions of phytosterols - Google Patents
Emulsions and aqueous dispersions of phytosterols Download PDFInfo
- Publication number
- WO2002065859A1 WO2002065859A1 PCT/EP2002/001715 EP0201715W WO02065859A1 WO 2002065859 A1 WO2002065859 A1 WO 2002065859A1 EP 0201715 W EP0201715 W EP 0201715W WO 02065859 A1 WO02065859 A1 WO 02065859A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phytosterol
- emulsifier
- aqueous phase
- fat
- phase
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0053—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0056—Spread compositions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/011—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/013—Spread compositions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/40—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the fats used
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/066—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the fat used
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
- A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
- A23G9/327—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds characterised by the fatty product used, e.g. fat, fatty acid, fatty alcohol, their esters, lecithin, glycerides
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- Emulsions and aqueous dispersions of phytosterols Emulsions and aqueous dispersions of phytosterols
- the present invention relates to edible compositions having an aqueous phase and comprising phytosterol(s) in the aqueous phase, to a method for preparing such compositions, and to the use of these compositions in preventing or treating hypercholesterolemia and other medical conditions.
- cholesterol-lowering effects of dietary plant sterols have been recognized for over 50 years.
- cholesterol is found in solution with other fats in micelles composed of bile salts, phospholipids, tri-, di- and monoglycerides, fatty acids and fat- soluble micronutrients.
- cholesterol in the micelles is transported across the intestinal lining and into the lymph. It is generally accepted that there are two possible mechanisms by which plant sterols can inhibit absorption of cholesterol from the small intestine: co-precipitation of cholesterol and plant sterols, and competition for space in mixed micelles.
- the alternative mechanism is related to the limited capacity in the mixed micelles for carrying cholesterol. Competition for this space by structurally similar plant sterols has the effect of restricting the amount of cholesterol that can be transported into the intestinal cells via the micelles.
- phytosterols renders them insoluble and barely dispersible in aqueous media.
- phytosterols tend to be added to the fat phase of fat- based food products.
- Health-conscious consumers wishing to benefit from the cholesterol- lowering effects of phytosterols are therefore forced to consume fat-rich foods, despite the health risks of a high fat diet.
- phytosterols have high melting points (typically about 136-150°C) it is important to maintain a temperature of 80°C or higher during dissolution of phytosterols in fats or oils, in order to avoid recrystallisation of the phytosterols.
- Crystalline phytosterol imparts an unpleasant grainy, waxy texture to edible and topical products.
- at 80°C and above commonly used fats and oils are vulnerable to oxidation. Rancid oils and fats detract greatly from the organoleptic properties of food products in particular.
- the problems associated with adding phytosterols to the fat phase are compounded in low fat, fat-based products.
- the amount of phytosterol capable of being dispersed in the fat phase of a fat-based emulsified product directly correlates with the amount of lipid in the product.
- the problems posed by the need to disperse phytosterols in fat become more acute the lower the fat content of a fat-based product.
- the fat- solubility of phytosterols can be improved by esterification, this is not a satisfactory solution to the problem, since phytosterol esters are biologically less efficacious than non-esterified phytosterols.
- phytosterol or phytosterol ester when distributed within the small volume lipid phase of a low fat emulsified product the taste of the product is adversely affected, since the high concentration of phytosterol in the fat leads to a waxy sensation in the mouth and on the tongue.
- the present invention concerns a new technique allowing unprecedentedly large amounts of phytosterol to be dispersed in an aqueous medium without causing adverse effects on mouth-feel.
- the resulting dispersions and emulsions made using these dispersions are stable, have low viscosity, and are easy to handle during downstream processing steps.
- This novel dispersion technique has broad applications not only within the food industry, but also to pharmaceutical manufacturing and to cosmetics.
- a method of preparing a product comprising phytosterol dispersed in an aqueous phase which comprises mixing particulate phytosterol with an aqueous medium in the presence of a non-sterol emulsifier having a HLB value higher than that of the phytosterol to create an aqueous phytosterol dispersion, such that the combined HLB value of the non-sterol emulsifier and the phytosterol in the aqueous phase does not exceed 8.
- a method of preparing an emulsified product comprising phytosterol dispersed in an aqueous phase, which comprises mixing particulate phytosterol with an aqueous phase, adding a non-sterol emulsifier having a HLB value of at least 7 to the aqueous phase and/or to a fat phase, and mixing together the aqueous phase and the fat phase to form an emulsion.
- compositions obtainable by the preparative method of the invention.
- a composition having an aqueous phase comprising a stable dispersion of a phytosterol and a phospholipid emulsifier having a HLB value > 7, wherein the weight ratio of phytosterokphospholipid emulsifier in the aqueous phase is greater than 1 :1 , and the combined HLB value of the phospholipid emulsifier and the phytosterol in the aqueous phase does not exceed 8.
- an emulsion having an aqueous phase comprising a phytosterol and a lipid phase comprising a phospholipid emulsifier of HLB > 7.
- a neutralizing emulsifier to reduce the viscosity of an aqueous dispersion of phytosterol or of an emulsion comprising said aqueous dispersion, particularly where said dispersion comprises a thickening agent.
- a neutralizing emulsifier to stabilize an emulsion comprising a fat phase and an aqueous phase comprising phytosterol, wherein the neutralizing emulsifier is in the aqueous phase or in the fat phase or distributed between the aqueous phase and the fat phase.
- composition of the invention as a medicament.
- composition of the invention in the manufacture of a medicament or therapeutic nutritional formulation for the prevention or treatment of any of: elevated blood cholesterol levels, hypertriglyceridemia, coronary heart disease, diabetes, atherosclerosis, inflammation, osteoarthritis, breast cancer, colon cancer, and benign prostatic hyperplasia.
- Figure 1 is a flowchart depicting a preferred method of manufacture of a spread according to the invention. Detailed Description of the Invention
- one or more neutralizing emulsifiers e.g. any oil-in-water emulsifier
- a surprisingly stable aqueous dispersion or emulsion of unexpectedly low viscosity is obtained.
- the neutralizing emulsifier whether in the aqueous phase, or the lipid phase of an emulsion, or distributed over both phases, manages to counteract some of the inherent w/o emulsifying activity of the phytosterol, preventing clumping together of phytosterol microparticles, formation of which is a major factor contributing to the viscosity and solidifying tendencies of phytosterols in aqueous media and in emulsions.
- the viscosity- reducing effect of the non-sterol emulsifier is particularly marked when a stabilizing thickener such as alginate is added to an aqueous dispersion containing phytosterol.
- Use of the neutralizing emulsifier enables high levels of thickener to be used without unduly increasing the viscosity.
- the rheological properties of the dispersion are dramatically improved by use of a neutralizing emulsifier.
- aqueous phytosterol dispersions of the invention can be used in the large- scale manufacture of emulsions containing high levels of phytosterol over a broad range of temperatures and under vigorous mixing conditions, without the drawback of breakdown of the emulsions and high viscosity.
- the mouth feel (bitterness, texture, grainy feel) of phytosterol in an aqueous dispersion or in the aqueous phase of an emulsion is improved through use of the neutralizing emulsifier, particularly when that emulsifier is phospholipid-based.
- the method of the present invention makes it possible to include phytosterols at effective levels in the aqueous phase of a broad range of nutritional, cosmetic and pharmaceutical products, thereby opening up new formulation opportunities, such as low fat and fat free formulations.
- sterol or “phytosterol” is intended to encompass any member of the family of free phytosterols (non-hydrogenated) and phytostanols, and esters or other derivatives thereof, and any mixture or combination thereof.
- the phytosterols used in the invention may be chemically synthesized, or may be derived from natural sources, including plant sources such as avocado, soy, rice bran, tall oil pitch or soap, shea nut, coconut, and plant oils, for example rapeseed, soya, maize, sunflower and sesame oils. Some germ oils are very rich in phytosterols, wheat germ and oats being good examples.
- plant sterols include sitosterol, stigmasterol, campesterol, brassicasterol, desmosterol, chalinosterol, poriferasterol, avenasterol, and clionasterol, and their corresponding stands.
- the phytosterols are provided in particulate powder form for use in preparing the dispersions of the invention. Dispersion is facilitated by using finely divided phytosterols, preferably where 95% of the particles have a size (diameter) of less than 10O ⁇ m, preferably less than 30 ⁇ m and most preferably less than 15 ⁇ m. Usually, the particle size distribution will be such that 90% of the particles are in the range "lOOnm to 35 ⁇ m, more preferably 0.2 to 20 ⁇ m, and most preferably 0.5 to 15 ⁇ m. Particle mixtures with this size range can be prepared by standard milling techniques, such as by use of an air mill, high energy hammermill, disc mill, or air filtration mill.
- the phytosterol is milled in the presence of sugar, and the powdered phytosterol/sugar mix is used in the preparation of sweetened food or nutritional products.
- the amount of phytosterol is preferred to be between about 0.5% and 20% by weight of the product, more preferably 1 % to 15%, and most preferably 2% to 10% by weight, for example 3 to 8% by weight.
- the phytosterol in the aqueous phase may constitute 1 -80 wt%, more preferably from 5-50 wt%, especially 7-25%, by weight of the aqueous phase.
- neutralizing emulsifier neutralizing non-sterol emulsifier
- o/w emulsifier o/w emulsifier
- the neutralizing non-sterol emulsifier has a HLB (Hydrophilicity-Lipophilicity Balance) value which is higher than the HLB of the phytosterol in the aqueous phase, usually in the range 6-20, preferably 7 to 12.
- the HLB system is a scale used for describing the characteristics of a surface-active agent. Detailed information on the HLB system and determination of HLB values can be found in the Kirk-Othmer Encyclopedia of Chemical Technology, (3 rd Ed.) 8: pp 910-918, which is incorporated herein by reference.
- Emulsifiers having HLB values in the range 7 to 18, especially 8 to 18, are often termed oil in water (o/w) emulsifiers.
- W/o emulsifiers have HLB values in the range 1-9, especially 1-6. Since HLB numbers are additive, the overall HLB value of a blend of emulsifiers of known HLB can easily be calculated.
- a single non-sterol emulsifier is used to neutralize the phytosterol.
- Suitable neutralizing emulsifiers for use in the invention include phosphatides of HLB at least 7 (e.g. lysophosphatides), especially phosphoglycerides such as phospholipids and lysophospholipids.
- Lecithin preparations (E322) of suitably high HLB are particularly preferred, and among this group lecithin preparations containing at least 90 wt%, preferably at least 95 wt%, of acetone insoluble compounds (mostly phospholipids) are preferred.
- Preparations of this sort have a low triglyceride content and are obtainable by dissolving away triglycerides from an impure lecithin preparation using acetone.
- EmultopTM (Lucas Meyer) and SternPure ETM (Stern) are suitable lecithin emulsifiers.
- the lecithin preparations used in the invention will comprise at least 3 wt%, and more preferably at least 5 wt%, of lysolecithin.
- Lecithin preparations comprising lysolecithin can be prepared from lecithin (e.g. soya lecithin or yolk lecithin) by enzymatic hydrolysis using snake venom phospholipase A2.
- a preferred lecithin preparation is one having a HLB value of between 8 and 10, preferably 8-8.5.
- neutralizing emulsifiers are [HLB values in brackets]: gelatin [9.8], sorbitan monolaurate [8.6], sodium oleate [18.0], potassium oleate [20.0], methylcellulose [10.5], acacia [12.0], tragacanth [13.2], triethanolamine oleate [12.0], polyoxyethylene monooleate [11.4], polyoxyethylene monostearate [11.6], polyoxyethylene monolaurate [13.1], polysorbates/Tweens [8 to 18] (specific examples being polyoxyethylene sorbitan monostearate (Tween 60/Tween 61) [14.9/9.6], polyoxyethylene sorbitan monooleate (Tween 80/Tween 81) [15/10], polyoxyethylene sorbitan monolaurate (Tween 20/Tween 21) [16.7/13.3], polyoxyethylene sorbitan monopalmitate (Tween 40) [15.6], polyoxyethylene sorbitan trio
- the HLB of the combination of all emulsifying components (including phytosterol and neutralizing emulsifier) in the aqueous dispersion exceeds that of the phytosterol component(s), and is ⁇ 8, preferably lying in the range of about 1 to 8, more preferably between 3 and 6.
- the amount of the non-sterol emulsifier in the aqueous dispersion is generally between 0.01 and 1% by weight, and most preferably about 0.5%, such as between 0.25 and 0.45%.
- Phytosterol is preferably in weight excess relative to the non-sterol emulsifier(s) in the aqueous dispersion.
- the relative weight proportions of phytosterol and non-sterol neutralizing emulsifiers present in the aqueous dispersion of the invention are optionally between 4:1 and 500:1, preferably between 7:1 and 50:1, and generally between 10:1 and 30:1.
- the phytosterol is dispersed in an aqueous medium, and the neutralizing emulsifier is incorporated into a lipid medium, and an emulsion is prepared by mixing both media together.
- the neutralizing emulsifier counteracts the low HLB of the phytosterol and stabilizes the emulsion formed when the aqueous phase and fat phases are mixed together.
- the phytosterol is preferably in weight excess relative to the non-sterol neutralizing emulsifier in the emulsified product, for instance in a dry weight ratio of 4:1 to 500:1 , preferably 7:1 to 50:1, and generally 10:1 to 30:1.
- the neutralizing emulsifier is distributed over both phases of the emulsion, preferably in the range 1 :9 to 9:1 parts by weight (fat phase conten aqueous phase content).
- the aqueous phytosterol-containing dispersion is mixed directly with a lipid composition to create a very stable emulsion having a fat phase and a water phase, the phytosterols being primarily localized to the water phase.
- the emulsified fat based products created in accordance with the invention may be oil-in-water (o/w, or water continuous) or water-in-oil (w/o, or oil continuous) emulsions according to which emulsifiers are selected for use in preparing the emulsion. W/o emulsions are preferred.
- enteral pharmaceutical and nutritional products such as edible spreads, margarines, and icings/frostings it is usual to generate a w/o emulsion.
- Salad dressings and infant formulas are generally o/w type emulsions.
- Preparations for external application may be either o/w or w/o emulsions.
- multiple emulsions of the w/o/w or o/w/o type can also be prepared.
- the weight proportion of the aqueous phase:fat phase can vary according to the intended application of the emulsion.
- this ratio usually varies between 1 :8 and 8:1.
- Regular yellow fat spreads and margarines contain up to 85% by weight of fat.
- Low fat spreads may contain 45-65% fat.
- Very low fat spreads comprise 30% fat or lower.
- the level of fat is generally from 10-60%, more preferably from 15-40% by weight of the product.
- Low fat salad dressings can contain as little as 0-10% by weight of lipids.
- the fat phase preferably comprises one or more vegetable oils, such as sunflower oil, soybean oil, rapeseed oil, canola oil, corn oil, peanut/groundnut oil and the like. Dairy and other animal fat may also be used. Other lipid substances in the fat phase can include petroleum-derived waxes and oils. If desired the fat may be hydrogenated, fractionated and/or interesterif ied.
- the fat in the fat phase it is preferred for the fat in the fat phase to comprise polyunsaturated fatty acids, PUFAs preferably contributing at least 30%, or more preferably at least 45%, of the fat phase by weight. Natural oils rich in PUFAs are the preferred source, some examples being sunflower, rapeseed, linseed, linola and/or soybean oils.
- An advantage of the present invention is that it circumvents the need to add a w/o emulsifier to the fat phase of an oil continuous product, which is standard practice in commercial manufacturing of such products.
- the partially-neutralized inherent w/o emulsifying activity of the phytosterol aqueous phase suffices to create a stable w/o emulsion. Therefore, in one embodiment of the invention w/o emulsifiers are omitted from the lipid phase in the formation of an oil continuous fat-based product.
- emulsifiers may be employed in the fat phase, optionally in addition to the neutralizing phospholipid emulsifier, for example where an o/w emulsion is prepared.
- Additional emulsifiers can include: anionic surfactants such as alcohol ether sulfates, alkyl sulfates, soaps and sulfosuccinates, sodium dodecyl sulfate (SDS), mono and diacylglycerides and derivatives thereof, e.g.
- cationic surfactants such as quaternary ammonium compounds
- zwitterionic surfactants such as alkyl betaine derivatives
- amphoteric surfactants such as fatty amine sulfates, difatty alkyl triethanolamine derivatives, phospholipids, lecithins, lysolecithins
- non-ionic surfactants such as the polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated fatty acids and alkylphenols, water-soluble polyethyleneoxy adducts onto polypropylene glycol and alkyl polypropylene glycol, nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxy- polyethoxyethanol, polyethylene glycol, octylphenoxy-polyethoxyethanol, lanolin alcohols, polye
- the emulsifier added to the fat phase is phytosterol.
- the emulsifier added to the fat phase is phytosterol.
- the amount of emulsifier required to be added to the fat phase varies according to the identity of the emulsifier, the type of emulsion, the material to be emulsified and the presence of stabilizing ingredients, but generally lies in the range 1-20% by weight of the lipid.
- the emulsion may comprise 0.05 to 1 %, preferably 0.05 to 0.5% by weight of mono and diglycerides. Exact amounts for particular applications can easily be determined by the skilled person. These will usually not need to be as high as levels used in conventional margarine manufacture, for instance, since their presence is only required where the emulsifying power of the partially neutralized phytosterols is insufficient to stabilize the emulsion.
- lyophilic colloids such as polysaccharides including acacia gum, agar, alginic acid, carrageenan, guar gum, gellan gum, carob gum, konjac gum, karaya gum, tragacanth, locust bean gum, xanthan gum, cellulose gums, gel- forming starches (e.g.
- modified food starches polydextrose, maltodextrin, cyclodextrins, pectin, cellulose and its methylated derivatives, microcrystalline cellulose (MCC), inulin, oatrim, curdlan; amphoterics (e.g. gelatin); fibers; proteins or peptides (e.g. Microparticulated Protein Product MPP or whey protein-based thickeners); and synthetic or semi-synthetic polymers (e.g.
- carbomer resins cellulose ethers, carboxymethyl cellulose (CMC), carboxymethyl chitin, polyethylene glycol-n (ethylene oxide polymer H(OCH 2 CH 2 ) n OH); finely divided solids including clays (e.g. attapulgite, bentonite, hectorite, kaolin, magnesium aluminium silicate and montmorillonite), microcrystalline cellulose oxides and hydroxides (e.g. aluminium hydroxide, magnesium hydroxide and silica); and cybotactic promoters/gellants including amino acids, lecithin and other phospholipids and poloxamers.
- clays e.g. attapulgite, bentonite, hectorite, kaolin, magnesium aluminium silicate and montmorillonite
- microcrystalline cellulose oxides and hydroxides e.g. aluminium hydroxide, magnesium hydroxide and silica
- cybotactic promoters/gellants including amino acids,
- Maltodextrin and/or alginate are the preferred stabilizers for addition to the aqueous phytosterol dispersion.
- the amount of emulsion stabilizer/thickener to be included in the compositions of the invention depends on the consistency desired in the end product. Usual amounts lie in the range 0 to 30%, preferably 0.1 to 25% based on the weight of the aqueous phase of the product. ln a preferred procedure for preparing an aqueous dispersion in accordance with the invention, the phytosterol is provided in particulate, powder form and pre-mixed with other powdered ingredients (excluding the non-sterol emulsifier and any thickener), before addition of the pre-mix to hot water (60°C to 85°C) or other aqueous medium.
- the powdered non sterol (o/w) emulsifier is then added to the aqueous medium containing the phytosterol.
- the powdered phytosterol and powdered non-sterol (o/w) emulsifier are added together (e.g. as a pre-mix, or simultaneously) to the heated aqueous medium. Once all the emulsifying ingredients are well dispersed it is possible to add thickening agents to the mix.
- the phytosterol-emulsifier complex in the aqueous medium is prepared by vigorous mixing, such as high shear mixing, e.g. by stirring, by turbine agitation, by propeller agitation, by microfluidization, by use of a centrifugal pump in standard Ventouri equipment, by use of a colloid mill or ball mill, by homogenization, by vortexing, by sonicating or by passing through a small orifice (e.g. in a French press).
- the aqueous medium comprising phytosterol and non-sterol (o/w) emulsifier is maintained at a temperature of between 60 and 100°C, generally about 80°C, and stirred until the phytosterol is evenly dispersed. At this point a milky suspension is obtained.
- the dispersion is kept under continuous agitation and, optionally, further water-soluble or water- dispersible ingredients are added to the suspension at this point: for example milk powder or protein, vegetable protein, colorings, flavorings, acidulants, preservatives, vitamins, salts, and so on.
- the aqueous phytosterol dispersion/suspension is phase-stable. This generally means, for example, that no phase separation is visible after at least 5 minutes, preferably after at least 30 minutes, and more preferably after at least 2 hours.
- the aqueous dispersion may be used as such in preparing any liquid food, beverage, topical formulation or medicament.
- the aqueous dispersion may be dried, for example by lyophilization or spray-drying, and then used in powdered form in a variety of applications.
- aqueous dispersion is employed (usually without an intermediate drying step) in the manufacture of an emulsified product comprising a fat phase and a water phase.
- W/o or o/w emulsions of this type can be prepared by any technique known in the art.
- non-sterol neutralizing emulsifier When the non-sterol neutralizing emulsifier is to be added to the fat phase of an emulsion it is melted into the fat blend that contains all the other fat ingredients, which is subsequently mixed with a phytosterol-containing aqueous phase (optionally prepared as described above).
- an aqueous dispersion of phytosterol (with or without the neutralizing non sterol emulsifier) is mixed with pre-heated lipid (oil or fat). Preheating is carried out at 50-60°C (preferably about 55°C).
- the pre-heated lipid comprises the non- sterol neutralizing emulsifier of the invention if none is already present in the aqueous dispersion or in addition to that added to the aqueous dispersion, and sometimes other emulsifiers which are lipid-soluble, such as lecithin, monoglycerides and diglycerides.
- An emulsion is created by mixing together the aqueous blend with the fat blend. Further processing of the emulsion depends on the intended use of the emulsion. In the preparation of margarines, spreads and the like, the emulsifying step is followed by pasteurization, crystallisation and filling, which are standard procedures in the art.
- the lipid used to make the emulsions may comprise additional fat-soluble components which are customary additives in the art, for example stabilizers, coloring agents, flavoring agents, pH regulators, vitamins (e.g. vitamins A & D), salts, anti-bacterial agents, antioxidants and preservatives.
- additional fat-soluble components which are customary additives in the art, for example stabilizers, coloring agents, flavoring agents, pH regulators, vitamins (e.g. vitamins A & D), salts, anti-bacterial agents, antioxidants and preservatives.
- vitamins e.g. vitamins A & D
- salts e.g., anti-bacterial agents, antioxidants and preservatives.
- antioxidants are tocopherols.
- Emulsified w/o products made by the preparative method of the invention are particularly phase stable and can be stored and transported under demanding conditions without exhibiting a tendency to separate.
- the nutritional product formats which are envisaged to incorporate the aqueous dispersion of the invention include: emulsified fat spreads or margarine, shortenings, cheese, mayonnaise, ice-cream, salad dressing, yoghurt, smoothies, chocolate, puddings, dairy desserts, coffee whitener, custards, dairy beverages, milk-shakes, icings, baked products, cake mixes, noodles, pasta, granola bars, soups, in ant ormulas, and the like.
- Medical nutrition products comprising the dispersion of the invention include enteral and parenteral complete formula diets, in liquid form or lyophilized for later reconstitution, and medical feeding supplements.
- Products formulated for enteral feeding may be intended for tube feeding or for oral administration, either in hospitals or in the home.
- the medical nutrition products may be formulated having regard to the needs of particular patient types, such as diabetics, heart disease patients, stroke patients, arthritis sufferers, cancer patients, and anyone at risk of developing these diseases.
- the nutritional products according to the invention may be non-fat products, low fat products or very low fat products.
- low fat is generally meant a product, such as a yellow fat spread, comprising less than 45% (e.g. 35-40%), preferably less than 35%, by weight fat.
- a "very low fat” product has less than 30% by weight fat.
- This invention makes possible the provision of phytosterols in oral pharmaceutical dosage forms, particularly solid forms, including tablets, capsules, dragees, granules, pellets, chews, solutions, syrups, lozenges, and powders.
- Parenteral emulsions can also be prepared for administration to severely-debilitated patients. Customary pharmaceutical excipients, diluents and stabilizers may be employed.
- Topical cosmetic and pharmaceutical formulations incorporating the emulsions of the invention include salves, creams, foams, lotions, gels, soaps, shampoos, and the like.
- the pharmaceutical, food or drink products may be supplemented with other health- promoting ingredients, particularly ingredients known to have benefits for the cardiovascular system.
- Non-limiting examples are PUFAs, polyphenols, lipid-soluble antioxidants (e.g. tocopherol, tocotrienols, lycopene), water-soluble antioxidants (e.g. ascorbate), amino acids, dietary fibers, vitamins, minerals and the like.
- a method for preventing or treating high blood cholesterol levels comprising administering, to a person in need of such treatment, a composition having an aqueous phase comprising a stable dispersion of a phytosterol and a phospholipid emulsifier having a HLB value ⁇ 7, wherein the weight ratio of phytosterol:phospholipid emulsifier in the aqueous phase is >1 , and the combined HLB value of the phospholipid emulsifier and the phytosterol in the aqueous phase does not exceed 8.
- high blood cholesterol is meant: over 200mg/dl, especially over 240mg cholesterol/dl blood; and/or a ratio total cholesterol/HDL of 5:1 or greater; and/or an LDL blood concentration of greater than 130mg/dl, especially over 160mg/dl.
- the pharmaceutical and nutritional products of the invention play a role in reducing blood cholesterol levels and thereby preventing cardiovascular disease and heart disease.
- the invention also provides a method of preventing or treating elevated blood cholesterol levels, hypertriglyceridemia, coronary heart disease, diabetes, atherosclerosis, Alzheimer's disease, inflammation, osteoarthritis, breast cancer, colon cancer, or benign prostatic hyperplasia comprising administering, to a person in need of such treatment, any composition of the invention as defined hereinbefore.
- Example 1 Properties of aqueous phytosterol dispersions made with different emulsifiers
- Aqueous dispersions were prepared having the compositions set out in Table
- Emultop (Lucas Meyer)
- Bolec C lecithin emulsifier of HLB approx. 3 and Tween 60 (polysorbate) emulsifier of HLB approx. 15.
- Table 2 shows that when attempts are made to dissolve phytosterols in water with the addition of a thickener the resulting dispersion is highly viscous and has an unpleasant taste. The absence of a thickener results in phase separation.
- Bolec C is a lecithin w/o emulsifier of low HLB. It can be seen from Table 2 that use of such an emusifier results in an aqueous dispersion of very high viscosity and thick texture, which also has a slightly sandy feel.
- Tween 60 a high HLB emulsifier improves the viscosity of a phytosterol-containing water dispersion, but it fails to mask the unpleasant bitter taste of the phytosterols, and moreover contributes an unpleasant taste of its own.
- Emultop which is a non-sterol lecithin emulsifier used in accordance with the invention, succeeded in moderating the viscosity of the aqueous phytosterol dispersion and simultaneously reducing the bitter taste of the phytosterol.
- These properties are optimal for preparing edible formulations containing phytosterol which are easily manageable during processing, have a long shelf life, and appeal to the consumer for taste reasons as well as for health benefits.
- Example 2 Viscous properties of emulsions made according to the invention
- An emulsion was prepared consisting of 35% fat phase (containing a mix of vegetable oils) and 65% water phase containing phytosterols (ReducolTM; Novartis Consumer Health), alginate thickener and EmultopTM lecithin emulsifier (Lucas Meyer) of HLB ⁇ 8, such that the concentrations of components in the emulsion were:
- the viscosity of the emulsion was measured using a Brookfield viscometer DV-1.spindle size c, at 50°C following the usual method known for viscosity measurement of shear thinning fluids after 30 minutes mixing time (mixing velocity 800 rpm), at a temperature of 50°C.
- the results are illustrated in Table 3.
- Example 3 Process for making a low-fat spread comprising phytosterol and Emultop in the aoueous phase
- a low-fat spread was prepared by the procedure outlined in the flow chart in Figure 1.
- the water phase is prepared by heating water up to 85°C and then all the powder ingredients are mixed in using a normal propeller.
- the oil phase is prepared by premixing the components at 65°C. Then both phases are mixed together in a premix tank and cycles of crystallization are carried out. Filling can be carried out manually or by automation.
- the mouthfeel of the resulting spread is comparable with that of conventional low fat spreads.
- the spread was found to be stable for more than 2 months at 4°C, and up to 9 hours at 25°C (no oil exudation).
- the emulsion generated in the premix tank was not excessively viscous and therefore did not clog the equipment in a manufacturing plant.
- An analogous emulsion made without neutralizing emulsifier was found to obstruct the pipes, leading to difficulties in pump- assisted phase transfer between tanks, and in emptying the tanks for cleaning.
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02719865A EP1363508A1 (en) | 2001-02-19 | 2002-02-18 | Emulsions and aqueous dispersions of phytosterols |
BR0207374-9A BR0207374A (en) | 2001-02-19 | 2002-02-18 | Phytosterol aqueous emulsions and dispersions |
CA002438519A CA2438519A1 (en) | 2001-02-19 | 2002-02-18 | Emulsions and aqueous dispersions of phytosterols |
JP2002565434A JP2004519232A (en) | 2001-02-19 | 2002-02-18 | Emulsions and aqueous dispersions of plant sterols |
MXPA03007419A MXPA03007419A (en) | 2001-02-19 | 2002-02-18 | Emulsions and aqueous dispersions of phytosterols. |
HU0400749A HUP0400749A2 (en) | 2001-02-19 | 2002-02-18 | Compositions containing emulsions and aqueous dispersions of phytosterols, process for their preparation and their use |
PL02363289A PL363289A1 (en) | 2001-02-19 | 2002-02-18 | Emulsions and aqueous dispersions of phytosterols |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0104074.0 | 2001-02-19 | ||
GBGB0104074.0A GB0104074D0 (en) | 2001-02-19 | 2001-02-19 | New composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002065859A1 true WO2002065859A1 (en) | 2002-08-29 |
Family
ID=9909052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/001715 WO2002065859A1 (en) | 2001-02-19 | 2002-02-18 | Emulsions and aqueous dispersions of phytosterols |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1363508A1 (en) |
JP (1) | JP2004519232A (en) |
BR (1) | BR0207374A (en) |
CA (1) | CA2438519A1 (en) |
GB (1) | GB0104074D0 (en) |
HU (1) | HUP0400749A2 (en) |
MX (1) | MXPA03007419A (en) |
PL (1) | PL363289A1 (en) |
WO (1) | WO2002065859A1 (en) |
ZA (1) | ZA200306161B (en) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1320301A1 (en) * | 2000-09-30 | 2003-06-25 | Eugene Science Inc. | Method for dispersing plant sterol for beverage and a plant sterol-dispersed beverage, of which particle size is nanometer-scale in dispersed beverage |
WO2003086108A1 (en) * | 2002-04-10 | 2003-10-23 | Archer-Daniels-Midland Company | Hydrothermically processed compositions containing phytosterols |
WO2005053414A1 (en) * | 2003-12-04 | 2005-06-16 | Unilever N.V. | Shelf stable homogeneous suspension |
EP1632137A1 (en) * | 2004-08-10 | 2006-03-08 | Kraft Foods Holdings, Inc. | Compositions and processes for water-dispersible phytosterols and phytostanols |
JP2006517222A (en) * | 2003-02-10 | 2006-07-20 | エンジィモテック リミテッド | Oils enriched with diacylglycerol and phytosterol esters for use in reducing cholesterol and triglycerides |
EP1859682A1 (en) * | 2005-02-24 | 2007-11-28 | San-Ei Gen F.F.I., Inc. | Vegetable sterol-containing milk drink and method of producing the same |
KR100816052B1 (en) | 2006-04-28 | 2008-03-21 | 주식회사 삼양제넥스 | Composition containing water-dispersed phytosterol ester |
EP2067410A1 (en) | 2007-12-07 | 2009-06-10 | Cognis IP Management GmbH | Water-dispersable sterol containing dispersion |
US7919135B2 (en) | 2006-03-13 | 2011-04-05 | The Hershey Company | Steeped cocoa beverages |
US8057837B2 (en) * | 2004-10-07 | 2011-11-15 | General Mills, Inc. | Microwave popcorn with viscous liquid fat and method of preparation |
US20120046254A1 (en) * | 2009-02-23 | 2012-02-23 | Thomas Francis Harting Glade | Dispersion of phytosterols |
US20120135956A1 (en) * | 2010-11-29 | 2012-05-31 | Raisio Nutrition Ltd | Compositions for preventing and treating an immune system disorder |
US20120135970A1 (en) * | 2010-11-29 | 2012-05-31 | Raisio Nutrition Ltd. | Compositions for preventing and treating an immune system disorder |
CN102740710A (en) * | 2010-02-06 | 2012-10-17 | 考格尼斯知识产权管理有限责任公司 | Drink |
US8945596B2 (en) | 2008-10-20 | 2015-02-03 | Conopco, Inc. | Antimicrobial composition |
WO2015131995A1 (en) * | 2014-03-03 | 2015-09-11 | Raisio Nutrition Ltd | Serum cholesterol lowering edible product |
US9132103B2 (en) | 2009-09-24 | 2015-09-15 | Conopco, Inc. | Disinfecting agent comprising eugenol, terpineol and thymol |
US9241500B2 (en) | 2006-03-13 | 2016-01-26 | The Hershey Company | Steeped cocoa compositions and functional cocoa beverages made from them |
US9408870B2 (en) | 2010-12-07 | 2016-08-09 | Conopco, Inc. | Oral care composition |
US9693941B2 (en) | 2011-11-03 | 2017-07-04 | Conopco, Inc. | Liquid personal wash composition |
US10695313B2 (en) | 2013-07-05 | 2020-06-30 | Raisio Nutrition Ltd | Edible composition suitable for lowering serum cholesterol |
CN115918906A (en) * | 2023-01-10 | 2023-04-07 | 丰益油脂科技有限公司 | Method for efficiently preparing water-dispersible phytosterol particles |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060233863A1 (en) | 2003-02-10 | 2006-10-19 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
WO2006016363A2 (en) | 2004-08-10 | 2006-02-16 | Enzymotec Ltd. | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
EP1839501A4 (en) * | 2004-11-17 | 2009-12-09 | San Ei Gen Ffi Inc | Sitosterol compound-containing composition and process for producing the same |
CA2673010A1 (en) * | 2005-12-20 | 2007-06-28 | Forbes Medi-Tech Inc. | Compositions comprising one or more phytosterols and/or phytostanols, or derivatives thereof, and high hlb emulsifiers |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3221579A1 (en) * | 1982-06-08 | 1983-12-22 | Eckert, Theodor, Prof. Dr., 4400 Münster | Solubilisation of active substances, which are sparingly soluble in water, in aqueous solution using a mixture of cholinephosphoric acid glycerol diester (choline-lecithin) and sodium deoxycholate as solubiliser, and the therapeutic use of the aqueous solutions obtained thereby |
DE4038385A1 (en) * | 1990-12-01 | 1992-06-04 | Roecar Holdings Nv | Sitosterol and its glycoside(s) with improved bio-availability - are in the form of microemulsions using lecithin as the carrier, isopropyl-myristate as the emulsifier and isopropanol as co-emulsifier |
EP0897671A1 (en) * | 1997-08-22 | 1999-02-24 | Unilever N.V. | Aqueous dispersions or suspensions |
EP0947197A1 (en) * | 1998-02-19 | 1999-10-06 | McNEIL-PPC, INC. | Method for producing water dispersible sterol formulations |
WO1999063841A1 (en) * | 1998-06-05 | 1999-12-16 | Forbes Medi-Tech Inc. | Compositions comprising phytosterol and/or phytostanol having enhanced solubility and dispersability |
EP0990391A1 (en) * | 1998-03-24 | 2000-04-05 | Kao Corporation | Phytosterol-containing fat composition |
WO2001037681A1 (en) * | 1999-11-24 | 2001-05-31 | Archer-Daniels-Midland Company | Phytosterol and phytostanol compositions |
-
2001
- 2001-02-19 GB GBGB0104074.0A patent/GB0104074D0/en not_active Ceased
-
2002
- 2002-02-18 JP JP2002565434A patent/JP2004519232A/en active Pending
- 2002-02-18 HU HU0400749A patent/HUP0400749A2/en unknown
- 2002-02-18 EP EP02719865A patent/EP1363508A1/en not_active Withdrawn
- 2002-02-18 WO PCT/EP2002/001715 patent/WO2002065859A1/en active Application Filing
- 2002-02-18 BR BR0207374-9A patent/BR0207374A/en not_active IP Right Cessation
- 2002-02-18 MX MXPA03007419A patent/MXPA03007419A/en unknown
- 2002-02-18 CA CA002438519A patent/CA2438519A1/en not_active Abandoned
- 2002-02-18 PL PL02363289A patent/PL363289A1/en not_active Application Discontinuation
-
2003
- 2003-08-08 ZA ZA200306161A patent/ZA200306161B/en unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3221579A1 (en) * | 1982-06-08 | 1983-12-22 | Eckert, Theodor, Prof. Dr., 4400 Münster | Solubilisation of active substances, which are sparingly soluble in water, in aqueous solution using a mixture of cholinephosphoric acid glycerol diester (choline-lecithin) and sodium deoxycholate as solubiliser, and the therapeutic use of the aqueous solutions obtained thereby |
DE4038385A1 (en) * | 1990-12-01 | 1992-06-04 | Roecar Holdings Nv | Sitosterol and its glycoside(s) with improved bio-availability - are in the form of microemulsions using lecithin as the carrier, isopropyl-myristate as the emulsifier and isopropanol as co-emulsifier |
EP0897671A1 (en) * | 1997-08-22 | 1999-02-24 | Unilever N.V. | Aqueous dispersions or suspensions |
EP0947197A1 (en) * | 1998-02-19 | 1999-10-06 | McNEIL-PPC, INC. | Method for producing water dispersible sterol formulations |
EP0990391A1 (en) * | 1998-03-24 | 2000-04-05 | Kao Corporation | Phytosterol-containing fat composition |
WO1999063841A1 (en) * | 1998-06-05 | 1999-12-16 | Forbes Medi-Tech Inc. | Compositions comprising phytosterol and/or phytostanol having enhanced solubility and dispersability |
WO2001037681A1 (en) * | 1999-11-24 | 2001-05-31 | Archer-Daniels-Midland Company | Phytosterol and phytostanol compositions |
Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1320301A4 (en) * | 2000-09-30 | 2004-06-30 | Eugene Science Inc | Method for dispersing plant sterol for beverage and a plant sterol-dispersed beverage, of which particle size is nanometer-scale in dispersed beverage |
US7994157B2 (en) | 2000-09-30 | 2011-08-09 | Kip Biotech Llc | Method for dispersing plant sterol for beverage and a plant sterol-dispersed beverage, of which particle size is nanometer-scale in dispersed beverage |
EP1320301A1 (en) * | 2000-09-30 | 2003-06-25 | Eugene Science Inc. | Method for dispersing plant sterol for beverage and a plant sterol-dispersed beverage, of which particle size is nanometer-scale in dispersed beverage |
WO2003086108A1 (en) * | 2002-04-10 | 2003-10-23 | Archer-Daniels-Midland Company | Hydrothermically processed compositions containing phytosterols |
JP2006517222A (en) * | 2003-02-10 | 2006-07-20 | エンジィモテック リミテッド | Oils enriched with diacylglycerol and phytosterol esters for use in reducing cholesterol and triglycerides |
EP1946644A2 (en) | 2003-12-04 | 2008-07-23 | Unilever N.V. | Shelf stable homogeneous suspension |
AU2004294698B2 (en) * | 2003-12-04 | 2007-11-29 | Upfield Europe B.V. | Shelf stable homogeneous suspension |
WO2005053414A1 (en) * | 2003-12-04 | 2005-06-16 | Unilever N.V. | Shelf stable homogeneous suspension |
US8383185B2 (en) | 2003-12-04 | 2013-02-26 | Conopco, Inc. | Shelf stable homogeneous suspension |
EP1946644A3 (en) * | 2003-12-04 | 2009-11-18 | Unilever N.V. | Shelf stable homogeneous suspension |
EP1632137A1 (en) * | 2004-08-10 | 2006-03-08 | Kraft Foods Holdings, Inc. | Compositions and processes for water-dispersible phytosterols and phytostanols |
US8057837B2 (en) * | 2004-10-07 | 2011-11-15 | General Mills, Inc. | Microwave popcorn with viscous liquid fat and method of preparation |
EP1859682A1 (en) * | 2005-02-24 | 2007-11-28 | San-Ei Gen F.F.I., Inc. | Vegetable sterol-containing milk drink and method of producing the same |
EP1859682A4 (en) * | 2005-02-24 | 2010-07-07 | San Ei Gen Ffi Inc | Vegetable sterol-containing milk drink and method of producing the same |
US9241500B2 (en) | 2006-03-13 | 2016-01-26 | The Hershey Company | Steeped cocoa compositions and functional cocoa beverages made from them |
US7919135B2 (en) | 2006-03-13 | 2011-04-05 | The Hershey Company | Steeped cocoa beverages |
KR100816052B1 (en) | 2006-04-28 | 2008-03-21 | 주식회사 삼양제넥스 | Composition containing water-dispersed phytosterol ester |
WO2009071246A1 (en) * | 2007-12-07 | 2009-06-11 | Cognis Ip Management Gmbh | Water-dispersable sterol containing dispersions |
EP2067410A1 (en) | 2007-12-07 | 2009-06-10 | Cognis IP Management GmbH | Water-dispersable sterol containing dispersion |
US8399042B2 (en) | 2007-12-07 | 2013-03-19 | Cognis Ip Management Gmbh | Water-dispersable sterol containing dispersions |
US8945596B2 (en) | 2008-10-20 | 2015-02-03 | Conopco, Inc. | Antimicrobial composition |
US20120046254A1 (en) * | 2009-02-23 | 2012-02-23 | Thomas Francis Harting Glade | Dispersion of phytosterols |
US9629378B2 (en) * | 2009-02-23 | 2017-04-25 | Thomas Francis Harting Glade | Dispersion of phytosterols |
US9132103B2 (en) | 2009-09-24 | 2015-09-15 | Conopco, Inc. | Disinfecting agent comprising eugenol, terpineol and thymol |
CN102740710A (en) * | 2010-02-06 | 2012-10-17 | 考格尼斯知识产权管理有限责任公司 | Drink |
AU2011212736B2 (en) * | 2010-02-06 | 2014-06-26 | Cognis Ip Management Gmbh | Drink |
US20120135970A1 (en) * | 2010-11-29 | 2012-05-31 | Raisio Nutrition Ltd. | Compositions for preventing and treating an immune system disorder |
US9603858B2 (en) * | 2010-11-29 | 2017-03-28 | Raisio Nutrition Ltd. | Compositions for preventing and treating an immune system disorder |
US20120135956A1 (en) * | 2010-11-29 | 2012-05-31 | Raisio Nutrition Ltd | Compositions for preventing and treating an immune system disorder |
US9408870B2 (en) | 2010-12-07 | 2016-08-09 | Conopco, Inc. | Oral care composition |
US9693941B2 (en) | 2011-11-03 | 2017-07-04 | Conopco, Inc. | Liquid personal wash composition |
US10695313B2 (en) | 2013-07-05 | 2020-06-30 | Raisio Nutrition Ltd | Edible composition suitable for lowering serum cholesterol |
US11771674B2 (en) | 2013-07-05 | 2023-10-03 | Raisio Nutrition Ltd | Edible composition suitable for lowering serum cholesterol |
WO2015131995A1 (en) * | 2014-03-03 | 2015-09-11 | Raisio Nutrition Ltd | Serum cholesterol lowering edible product |
US10532060B2 (en) | 2014-03-03 | 2020-01-14 | Raisio Nutrition Ltd. | Serum cholesterol lowering edible product |
CN115918906A (en) * | 2023-01-10 | 2023-04-07 | 丰益油脂科技有限公司 | Method for efficiently preparing water-dispersible phytosterol particles |
Also Published As
Publication number | Publication date |
---|---|
JP2004519232A (en) | 2004-07-02 |
EP1363508A1 (en) | 2003-11-26 |
CA2438519A1 (en) | 2002-08-29 |
HUP0400749A2 (en) | 2004-08-30 |
GB0104074D0 (en) | 2001-04-04 |
ZA200306161B (en) | 2004-08-02 |
PL363289A1 (en) | 2004-11-15 |
MXPA03007419A (en) | 2003-11-18 |
BR0207374A (en) | 2004-06-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1363508A1 (en) | Emulsions and aqueous dispersions of phytosterols | |
EP1315482B1 (en) | Water-dispersible encapsulated sterols | |
EP1197153B2 (en) | Aqueous dispersions or suspensions | |
AU2006201678B2 (en) | Stabilized dispersion of phytosterol in oil | |
US20030165572A1 (en) | Water-dispersible encapsulated sterols | |
JP5630770B2 (en) | Phytosterol dispersion | |
JP2008143843A (en) | Pulverized phytosterol ester preparation, method for producing the same and food and drink containing the same | |
WO2007071036A1 (en) | Emulsions comprising non-esterified phytosterols in the aqueous phase | |
AU2005234649B2 (en) | Water-dispersible encapsulated sterols | |
EP1501367B1 (en) | Food product comprising a phytosterol | |
AU2002250969A1 (en) | Emulsions and aqueous dispersions of phytosterols | |
AU2006202608A1 (en) | Emulsions and aqueous dispersions of phytosterols | |
US20110223312A1 (en) | Triglyceride-encapsulated phytosterol microparticles dispersed in beverages | |
AU2002317786A1 (en) | Stabilized dispersion of phytosterol in oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LT LU LV MA MD MK MN MX NO NZ OM PH PL PT RO RU SE SG SI SK TJ TM TN TR TT UA US UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2002250969 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002719865 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2003/06161 Country of ref document: ZA Ref document number: 200306161 Country of ref document: ZA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002565434 Country of ref document: JP Ref document number: 2438519 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2003/007419 Country of ref document: MX |
|
WWP | Wipo information: published in national office |
Ref document number: 2002719865 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |