EP1991069A2 - Ester de sterols comprenant des acides gras a chaine courte - Google Patents

Ester de sterols comprenant des acides gras a chaine courte

Info

Publication number
EP1991069A2
EP1991069A2 EP07711676A EP07711676A EP1991069A2 EP 1991069 A2 EP1991069 A2 EP 1991069A2 EP 07711676 A EP07711676 A EP 07711676A EP 07711676 A EP07711676 A EP 07711676A EP 1991069 A2 EP1991069 A2 EP 1991069A2
Authority
EP
European Patent Office
Prior art keywords
fatty acid
sterol
fatty acids
acid esters
chain
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Withdrawn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
EP07711676A
Other languages
German (de)
English (en)
Inventor
Peter Horlacher
Dieter Hietsch
Wolfgang Albiez
Franz Timmermann
Katja Beck
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
Publication of EP1991069A2 publication Critical patent/EP1991069A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1315—Non-milk proteins or fats; Seeds, pulses, cereals or soja; Fatty acids, phospholipids, mono- or diglycerides or derivatives therefrom; Egg products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; PREPARATION THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/1528—Fatty acids; Mono- or diglycerides; Petroleum jelly; Paraffine; Phospholipids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR 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 OR 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 OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols

Definitions

  • the invention is in the field of sterols and relates to particular sterol esters, foods, cosmetic and pharmaceutical preparations containing these sterol esters and their use for the preparation of cholesterol lowering agents.
  • emulsifiers must therefore be used which decisively improve the dispersing properties. Even if food emulsifiers are characterized by good compatibility and are already known over a long period of time, attempts are made to reduce the amount of emulsifiers or even to completely avoid them, since emulsifiers are also known influence the bioavailability of other substances present in the food or can negatively alter the stability of the formulations.
  • emulsifiers nevertheless requires further technically inventive formulation developments in order to minimize the disadvantages of poor further processing.
  • sterol-emulsifier complexes allow a direct and easy incorporation of the sterols in food preparations.
  • the reduced sterol content of the formulations has a disadvantageous effect, since the addition of the emulsifiers is increased by increasing the amounts used.
  • sterol and stanol esters are usually derivatives with fatty acids from vegetable oils such as sunflower oil, rapeseed oil, linseed oil, rice germ oil, safflower oil or soybean oil and therefore have predominantly longer chain saturated and unsaturated fatty acids with chain lengths of 16 to 22 carbon atoms.
  • the esterified derivatives can be slightly better incorporated due to their higher solubility.
  • M.F.M. As early as 1907, Jaeger described some short-chain sterol esters with regard to their physico-chemical properties (M.F.M. Jaeger, Recueil des Travaux Chimiques des Pays-Bas et de Ia Lecture, 26 (1907), pp. 311 to 356).
  • esters of longer-chain saturated fatty acids are their poor processability, which is largely due to their high melting point.
  • sterol esters of unsaturated fatty acids are easier to process, the foods added with these steroids have poor stability.
  • the proportion of total sterol in the formulation decreases, so that larger amounts of the esters must be incorporated in order to achieve a high sterol content in the food.
  • low-melting esters with short-chain fatty acids have the disadvantage of poor organoleptic and sensory properties, which have an unpleasant effect on the intake of the foods they contain.
  • the invention relates to sterol fatty acid esters of medium-chain fatty acids having a chain length of 8 and 10 carbon atoms in a fatty acid distribution C 8 to Cio (weight ratio) of 95: 5 to 5:95, fatty acid distributions of Cg to Ci 0 (weight ratio) of 90:10 are preferred 20:80 and in particular distributions of the fatty acids C 8 to Ci 0 (weight ratio) of 64:36 to 50:50 or of 78:22 to 65:35 used. Taking into account impurities and other fatty acids, the weight ratio 64:36 to 50:50 covers the distribution C 8 to Ci 0 of 60:40 and the ratio 78:22 to 65:35 the distribution C 8 to Cio of 70:30.
  • Suitable compounds are unbranched and branched, saturated and unsaturated fatty acids, including preferably those selected from the group formed by n-octanoic acid, n-decanoic acid and ethylhexanoic acid. Particularly preferred are the saturated unbranched fatty acids caprylic acid (n-octanoic acid) and / or capric acid (n-decanoic acid).
  • the sterol fatty acid esters according to the invention contain not more than 10% by weight, preferably not more than 5% by weight and in particular not more than 3% by weight of fatty acids other than C 8 and C 10, based on the weight of the total fatty acids contained in the ester.
  • these sterol derivatives are also suitable for processing in beverages and milk products.
  • the best processing characteristics were fatty acid distributions of C 8 to C 0 0 of 64:36 to 50:50 or of 78:22 to 65:35, since here the lowest melting point depression of the mixtures compared to the pure fatty acids was observed.
  • the fatty acid mixture contains not more than 10% by weight, preferably not more than 5% by weight, more preferably not more than 3% by weight, of fatty acids of other chain lengths.
  • the food to be produced need only be heated to a maximum of 60 to 75 ° C during processing and the molten sterol ester can be very easily distributed by simple stirring. On subsequent cooling, it is present in a very fine and homogeneous distribution in the food product. In addition to the low intrinsic taste of the medium-chain sterol ester, the food produced in this way also has very good organoleptic and sensory properties due to its extremely fine distribution.
  • the high total sterol content which results in the food products enriched therewith by the high sterol content of the ester is particularly advantageous for the choice of medium-chain fatty acids.
  • the sterol derivatives according to the invention have a much higher content of pure sterol and make it possible to reduce the total amount of sterol derivative to be used.
  • the sterol esters according to the invention contain at least 60% by weight, preferably at least 70% by weight and more preferably at least 75% by weight of total sterol content, based on the weight of the sterol compound.
  • fatty acids are used for the esterification, as they are present in the form of medium-chain triglycerides, so-called “medium chain triglycerides” (MCT) - also called miglyol® - esterified with glycerol MCT oils in the field of human nutrition reduce the absorption of fatty substances and increase both the fat burning and the rate of metabolism, even with sterol esters of these fatty acids further nutritionally valuable main and side effects are conceivable
  • MCT medium chain triglycerides
  • the sterol esters of the present invention have a solid consistency which contributes to good processing as it allows for easy dosing, compartmentalizing and packaging.
  • the esters with medium-chain, saturated fatty acids allow good storage, because they are much more stable to oxidation than conventional sterol esters based on sunflower oil, rapeseed oil, linseed oil, rice germ oil, safflower oil or soybean oil, the predominantly long-chain saturated and unsaturated fatty acids with chain lengths of 16 to 22 carbon atoms.
  • the sensory properties are not affected by the usual storage and / or transport conditions.
  • the sterol derivative according to the invention can be stored under standard conditions (RT) and also transported at elevated temperatures, such as occur in Asian countries and / or in summer (30-40 ° C.), without any impairment of the product properties.
  • RT standard conditions
  • This good oxidation stability affects Of course, in terms of improved stability of the enriched food product from.
  • Sterol fatty acid esters of medium-chain fatty acids having a chain length of 8 and / or 10 carbon atoms in a fatty acid distribution C 8 to Ci 0 of 100: 0 to 0: 100 are therefore outstandingly suitable for the preparation of cholesterol-lowering agents.
  • sterols derived from plants and vegetable raw materials so-called phytosterols and phytostanols, which belong to the groups of 4-demethyl-sterols, 4-monomethyl-sterols and 4,4-dimethyl-sterols are used.
  • 4-desmethyl-sterols are, for example, ergosterol, brassicasterol, campesterol, avenasterol, desmosterol, clionasterol, stigmasterol, poriferasterol, chalidinol, sitosterol and mixtures thereof, among which ⁇ -sitosterol, stigmasterol, campesterol and brassicasterol are preferably used.
  • Seed and oils from soybeans, canola, palm kernels, maize, coconut, oilseed rape, sugar cane, sunflower, olive, cotton, soy, peanut or products from tall oil production are among the sources used for the terols.
  • Sterols from tall oil production and rapeseed sterols are preferably used.
  • sterols and stanols are obtained.
  • the majority of the sterols is provided by ⁇ -sitosterol, furthermore the sterol mixtures contain larger amounts of campesterol and stigmasterol, as well as the hydrogenated derivatives systanol and campestanol and small amounts of brassicasterol and less than 3% of other sterols and stanols.
  • the hydrogenated saturated forms of sterols also fall under the compounds used.
  • the stanol fatty acid esters of medium chain fatty acids having a chain length of 8 and 10 carbon atoms in a fatty acid distribution C 8 to Cio (weight ratio) of 95: 5 to 5:95 are preferred fatty acid distributions of C 8 to Cio (weight ratio) of 90:10 to 20:80 and in particular distributions of the fatty acids C 8 to Cio (weight ratio) of 64:36 to 50:50 or of 78:22 to 65:35 advantageously suitable for processing in food products.
  • the preparation can be carried out by the common methods, such. For example: esterification of sterol and / or mixtures of different sterols or stanols with saturated medium-chain fatty acids C8 and ClO.
  • the esterification can also be carried out starting from esters of fatty acids via a transesterification.
  • an esterification with the corresponding acid anhydride or acid halides possible.
  • Corresponding methods can be found in the prior art.
  • the sterol fatty acid ester according to the invention makes it possible to dispense with emulsifiers during incorporation into foods. It can be easily incorporated into foods selected from the group consisting of spreadable fats, margarine, butter, vegetable oils, frying fats, peanut butter, mayonnaise, dressings, cereals, bread and bakery products, cakes, wheat bread, rye bread, toasted bread, crispbread , Ice cream, puddings, dairy products, yoghurt, quark, cream, confectionery, chocolate, chewing gum, cereal bars, milk drinks, soy drinks, fruit juices, vegetable juices, fermented drinks, rice noodles, sauces, cheese, cheese spreads, meat and sausage products.
  • foods selected from the group consisting of spreadable fats, margarine, butter, vegetable oils, frying fats, peanut butter, mayonnaise, dressings, cereals, bread and bakery products, cakes, wheat bread, rye bread, toasted bread, crispbread , Ice cream, puddings, dairy products, yoghurt, quark, cream
  • the molten sterol ester is very well distributed by simple stirring and is very finely and homogeneously distributed on subsequent cooling, particularly water-containing and temperature-sensitive food products such as beverages and milk products, such as milk, Milk drinks, whey and yoghurt drinks, fruit juices, fruit juice mixtures, fruit juice drinks, vegetable juices, carbonated and non-carbonated drinks, soy milk drinks or protein-rich liquid diet replacement drinks, and fermented milk preparations, yogurt, yogurt, or cheese preparations suitable as a basis for the sterol esters according to the invention.
  • beverages and milk products such as milk, Milk drinks, whey and yoghurt drinks, fruit juices, fruit juice mixtures, fruit juice drinks, vegetable juices, carbonated and non-carbonated drinks, soy milk drinks or protein-rich liquid diet replacement drinks, and fermented milk preparations, yogurt, yogurt, or cheese preparations suitable as a basis for the sterol esters according to the invention.
  • Another object of the invention therefore relates to food products containing the sterol fatty acid esters of the invention.
  • the sterol compounds are preferably used in beverages and milk products, which then 0.1 to 50 wt .-%, preferably 0.5 to 20 wt .-%, particularly preferably 0.5 to 3 wt.% Of sterol esters based on the total weight of Contain food, and in fat-based products in which preferably 1 to 25 wt.%, Particularly preferably 5 to 10 wt.% Based on the total weight of the food are incorporated.
  • the mixture was then heated for 3 hours at 210 0 C, the upper phase of the reaction distillate was continuously returned to the batch. Thereafter, the batch was evacuated to 100 mbar and stirred for 4 hours. The fatty acid excess was then distilled off at 15 mbar and the mixture was cooled to 90 0 C and vented with nitrogen. The batch was dried for 30 minutes at 85 ° C. and ⁇ 30 mbar, before venting with nitrogen. The final purification was carried out at 190 ° C and 3 mbar by introducing stripping steam (0.2 g per minute). The residue obtained was 1911 g of an odorless, light, sensory neutral, high melting solid and 16 g of a yellow clear distillate.
  • the prepared sterol ester with medium-chain fatty acids of chain length distribution about 70 wt.% C 8 and about 30 wt.% Qo has improved stability over commercially available fatty acid esters with sunflower or rapeseed oil fatty acids (predominantly linoleic acid, oleic acid and small amounts of palmitic acid and stearic acid) compared to pure sterol improved organoleptic properties and improved processability.
  • the mixture was then heated for 3 hours at 210 ° C, wherein the upper phase of the reaction distillate was recycled continuously in the approach. Thereafter, the batch was evacuated to 100 mbar and stirred for 4 hours. The fatty acid excess was then distilled off at 15 mbar and the mixture was cooled to 90 0 C and vented with nitrogen. The batch was dried for 30 minutes at 85 ° C. and ⁇ 30 mbar, before venting with nitrogen. The final purification was carried out at 190 ° C and 3 mbar by introducing stripping steam (0.2 g per minute). The residue obtained was 1968 g of an odorless, light, sensory neutral, high melting solid (mp: 57.7 ° C.).
  • the produced sterol ester with medium-chain fatty acids of chain length distribution about 60 wt.% C 8 and about 40 wt.% Ci 0 has improved over commercial fatty acid esters with sunflower or rapeseed oil fatty acids (mainly linoleic acid, oleic acid and small amounts of palmitic acid and stearic acid) Stability and compared to pure sterol improved organoleptic properties and improved processability Gas chromatographic analysis of the sterol ester prepared in Example 2:
  • organoleptic test of the products was carried out in the form that the sterol esters and comparison products prepared were dissolved at 4O 0 C in oil (MCT oil, Delios®, Cognis) (50% solution) and were eaten.
  • the organoleptically tested sterol esters were prepared analogously to Example 1, whereby the mixing ratio of 70% by weight of tall oil sterols and 30% by weight of rapeseed sterols was likewise observed for the sterols.
  • Branched FS or fatty acids with functional group such as lactic acid, also did not show the rapid crystallization behavior.
  • the sterol-lactic acid ester is therefore also suitable for use in foods.
  • the preferred sterol ester should contain a higher proportion of fatty acid of chain length C8.
  • the melting point determination of the sterol esters with different ratios of C 8 and C 10 fatty acids was carried out in a conventional manner using melting point tubes.
  • the investigated sterol esters were prepared analogously to Example 1 with pure octane and pure decanoic acid, the sterol content contained the mixing ratio 70 wt.% Tallölsterine and 30 wt.% Raps sterols.
  • the milk (1O 0 C) was placed and heated to 75 0 C. was then treated with an Ultra Turrax the sterol fatty acid ester C 8 Ci 0 60/40 (7O 0 C) sec 30th alternates at 10000 U / min eindisper-.
  • the preparation was pasteurized at 90 ° C and then cooled to 8 ° C.
  • the milk mix (1O 0 C) was introduced and heated to 75 ° C. Subsequently, with an Ultra Turrax of Sterol-C 8 Ci o-fatty acid ester 60/40 (70 0 C) for 30 sec. at 10000 rev / min dispersed.
  • the mixture was pasteurized at 90 ° C and then cooled to 45 ° C.
  • the milk preparation was inoculated.
  • a preliminary solution of 50 g yoghurt cultures YC 180 (Chr. Hansen) and 450 g milk was stirred. From this preliminary solution, 2 ml / liter of process fluid was used.
  • the inoculated preparation for fermentation in a climatic chamber at 45 ° C was made.
  • the yoghurt was cooled (firm yoghurt), or mixed with 7% sugar and stirred (stirred yogurt), or homogenized again with 80-100 bar (drinking yoghurt)

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Biophysics (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Hematology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Fats And Perfumes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Seasonings (AREA)
  • Edible Oils And Fats (AREA)

Abstract

L'invention concerne des esters d'acides gras de stérols d'acides gras à chaîne moyenne, présentant une longueur de chaîne comprise entre 8 et 10 atomes de carbone dans une répartition d'acides gras C8 à C10 (rapport en poids) comprise entre 95:5 et 5:95, de préférence, les répartitions d'acides gras de C8 à C10 (rapport en poids) sont comprises entre 90:10 et 20:80, et en particulier les répartitions des acides gras C8 à C10 (rapport en poids) sont comprises entre 64:36 et 50:50 ou entre 78:22 et 65:35. De préférence, des acides décanoïques et/ou des acides capryliques sont utilisés en tant qu'acides gras. Lesdits composés de stérols peuvent être incorporés facilement dans des aliments, en particulier, dans des boissons et des produits laitiers grâce à leur mouillabilité et leurs propriétés de fusion à faible température sans côuts techniques élevés, et présentent de bonnes propriétés organoleptiques et sensorielles, ainsi qu'une stabilité améliorée par rapport aux esters de stérols commerciaux présentant des acides gras à longue chaîne et non saturés.
EP07711676A 2006-03-08 2007-02-27 Ester de sterols comprenant des acides gras a chaine courte Withdrawn EP1991069A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102006011090 2006-03-08
DE102006041302A DE102006041302A1 (de) 2006-03-08 2006-09-01 Sterolester mit kurzkettigen Fettsäuren
PCT/EP2007/001656 WO2007101580A2 (fr) 2006-03-08 2007-02-27 Ester de sterols comprenant des acides gras a chaine courte

Publications (1)

Publication Number Publication Date
EP1991069A2 true EP1991069A2 (fr) 2008-11-19

Family

ID=38336174

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07711676A Withdrawn EP1991069A2 (fr) 2006-03-08 2007-02-27 Ester de sterols comprenant des acides gras a chaine courte

Country Status (6)

Country Link
US (1) US20090099146A1 (fr)
EP (1) EP1991069A2 (fr)
JP (1) JP2009529073A (fr)
AU (1) AU2007222696B2 (fr)
DE (1) DE102006041302A1 (fr)
WO (1) WO2007101580A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101581A2 (fr) * 2006-03-08 2007-09-13 Cognis Ip Management Gmbh Poudre contenant des sterols
CN110477100B (zh) * 2019-08-22 2023-11-07 内蒙古蒙牛乳业（集团）股份有限公司 一种两吃型酸奶固体饮料及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3751569A (en) * 1972-01-12 1973-08-07 Procter & Gamble Clear cooking and salad oils having hypocholesterolemic properties
HK1001951A1 (en) * 1991-05-03 1998-07-24 Raisio Benecol Ltd. A substance for lowering high cholesterol level in serum and a method for preparing the same
FI107015B (fi) * 1996-08-09 2001-05-31 Raisio Benecol Oy Kasvistanolirasvahappoestereiden seos ja sen käyttö sekä elintarvike
FI107538B (fi) * 1997-02-26 2001-08-31 Raisio Benecol Oy Menetelmä stanoliesterien valmistamiseksi
EP0897971B1 (fr) * 1997-08-22 2004-11-03 Unilever N.V. Composition contenant un ester de stanol
ES2222553T3 (es) * 1997-08-22 2005-02-01 Unilever N.V. Producto alimenticio a base de grasa que comprende esteroles.
EP1298194B1 (fr) * 1997-08-22 2006-10-04 Unilever N.V. Compositions contenant un ester de stanol
US8158184B2 (en) * 2004-03-08 2012-04-17 Bunge Oils, Inc. Structured lipid containing compositions and methods with health and nutrition promoting characteristics
US20070031571A1 (en) * 2005-08-03 2007-02-08 Peter Cremer North America, Lp Phytosterol esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
AU2007222696A1 (en) 2007-09-13
AU2007222696B2 (en) 2012-05-17
US20090099146A1 (en) 2009-04-16
DE102006041302A1 (de) 2007-09-13
JP2009529073A (ja) 2009-08-13
WO2007101580A2 (fr) 2007-09-13
WO2007101580A3 (fr) 2007-10-18

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