EP1991070A2 - Poudre contenant des sterols - Google Patents

Poudre contenant des sterols

Info

Publication number
EP1991070A2
EP1991070A2 EP07711677A EP07711677A EP1991070A2 EP 1991070 A2 EP1991070 A2 EP 1991070A2 EP 07711677 A EP07711677 A EP 07711677A EP 07711677 A EP07711677 A EP 07711677A EP 1991070 A2 EP1991070 A2 EP 1991070A2
Authority
EP
European Patent Office
Prior art keywords
sterol
esters
containing powder
powder formulations
ester
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Withdrawn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
EP07711677A
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 EP1991070A2 publication Critical patent/EP1991070A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A23D7/005—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 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
    • 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
    • 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
    • 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

Definitions

  • the invention is in the field of foodstuffs and relates to formulations for incorporation into foods, cosmetic and pharmaceutical preparations containing mixtures of sterols, esters with their esters in the form of a supercooled melt, a process for the preparation thereof and preparations, in particular foods, which these formulations include.
  • the literature offers numerous formulation options for incorporating the poorly soluble phytosterols and stanols known as cholesterol-lowering into food preparations, cosmetic or pharmaceutical products.
  • the unfavorable solubility behavior of the substances results not only in poor dispersibility but also in reduced bioavailability and unsatisfactory stability of the food preparations.
  • EP 1 005 859 B1 US Pat. No. 6,267,963 B1 and International Patent Application WO 03/077680 A1 propose sterol formulations which are prepared by co-melting of sterols and emulsifiers. These co-crystallized sterol-emulsifier complexes allow direct and easy incorporation of the steroids into food preparations.
  • the reduced sterol content of the formulations however, has a disadvantageous effect, since the increase in the amounts used also increases the entry of the emulsifiers.
  • sterol esters show a sterol-like cholesterol-lowering effect.
  • the esterified derivatives can be incorporated slightly better, because they are due to their lower melting point by the melting in the heated food to be distributed homogeneously.
  • Commercially available sterol 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. They are prepared by transesterification or esterification of free sterols as in the process disclosed in European Patent EP 0 914 329 B1.
  • the selection of the fatty acids decisively influences the properties of the different sterol derivatives in terms of their melting point, their stability and their solubility as already described in US Pat. No. 3,751,569 and in European Patent EP 1 075 191 B1.
  • Sterol fatty acid esters are difficult to process into powders since, depending on the fatty acid used, they have a sticky pasty or viscous consistency.
  • the invention relates to sterol-containing powder formulations in the form of a supercooled melt of sterols and sterol esters with the proviso that the sterol content is at least 30 wt.% Based on the content of the powder.
  • the formulations of the invention are obtainable by co-melting free unesterified sterols and sterol esters, solidifying the molten mixture by rapid cooling and milling the solidified melt.
  • sterol esters due to their production, contain a greater or lesser amount of free sterols, which is due to the fact that the present sterols are not completely esterified.
  • European Patent EP 0 911 385 B1 describes sterol esters with a degree of esterification of 40 to 85%.
  • DSC differential scanning calorimetry
  • the sterol formulations according to the invention have improved organoleptic properties compared to pure sterol formulations and sterol esters. In contrast to pure sterol esters, they can be processed into readily flowable powders, which then have a significantly higher total sterol content.
  • the powders according to the invention contain at least 65% by weight, preferably at least 75% by weight and more preferably more than 80% by weight, of total sterol, based on the weight of the powder.
  • sterols derived from plants and vegetable raw materials so-called phytosterols and phytostanols
  • ergosterol ergosterol
  • brassicasterol campesterol
  • avenasterol desmosterol
  • clionasterol stigmasterol
  • poriferasterol chalinosterol
  • sitosterol sitosterol and mixtures thereof, among which ⁇ -sitosterol and campesterol are preferably used.
  • the hydrogenated saturated forms of the sterols, the so-called stanols fall under the compounds used, also here ß-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.
  • the particle size of the sterol powder to be processed can then be above the micronization range.
  • the amount of unesterified sterol used in the melt is also limited by the melting point of the supercooled melt. In order to ensure good processability by simply melting the formulation in the food, the amount of sterol esters used should not fall below 30% by weight.
  • Fatty esters with fatty acids of chain lengths of 2 to 26 carbon atoms are usually used as sterol esters.
  • Possible fatty acids are short-chain fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid, dicarboxylic acids such as oxalic acid and maleic acid, hydroxy acids such as citric acid, lactic acid, and long-chain saturated and unsaturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidonic acid , Behenic acid, oleic acid, erucic acid, elaidic acid, linoleic acid, conjugated linoleic acid, linolenic acid, docosahexaenoic acid or eicosapentaenoic acid.
  • Preference is given to sterol esters of saturated and unsaturated fatty acids having chain lengths of 16 and 18 carbon
  • MCT medium chain triglycerides
  • Miglyol® sterol esters with fatty acids of this chain length have good organoleptic properties and are much more resistant to oxidation than commercial sterol esters with long-chain and unsaturated fatty acids.
  • MCT oils in the field of human nutrition reduce the absorption of fatty substances and increase both the fat burning and the metabolization rate, sterol esters of these fatty acids are also of major nutritional value - and side effects conceivable.
  • the chain lengths of 8 and 10 carbon atoms are preferably used, in a fatty acid distribution (weight ratio) C8 to ClO of 100: 0 to 0: 100, preferably 60: 40 to 50: 50 and particularly preferably 75: 25 to 65:35.
  • the fatty acid mixture contains not more than 7% by weight, preferably not more than 5% by weight, more preferably not more than 3% by weight, of fatty acids of other chain lengths.
  • a sterol ester with medium-chain fatty acids of chain length distribution 69 to 75 wt.% C8 and 23 to 27 wt.% ClO has improved stability over commercial fatty acid esters with sunflower or rapeseed oil fatty acids (predominantly linoleic acid, oleic acid and small amounts of palmitic acid and stearic acid) and compared to pure sterol improved organoleptic properties and improved processability.
  • the mixtures of medium-chain sterol esters and sterols in contrast to the common sterol esters based on unsaturated fatty acids such as sunflower fatty acid or rapeseed fatty acid, have a high oxidative stability.
  • the sensory properties are not affected by the usual storage and / or transport conditions.
  • the product 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 causing any damage to the product properties.
  • the sterol powder according to the invention makes it possible to provide powders having a high total sterol content which enable easy further processing of the lipophilic active ingredients in foods, in particular beverages.
  • 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 preparation can be carried out by the common methods, such. B .: esterification of sterol and / or mixtures of different sterols or stanols with fatty acids, more preferably with saturated medium-chain fatty acids C8 and ClO.
  • the esterification can also be carried out starting from esters of fatty acids. Corresponding methods can be found in the prior art.
  • the selected sterol esters are melted together with the free sterols at 120 to 190 ° C and rapidly cooled to a temperature of 10 to 25 ° C.
  • the thus solidified melt is comminuted with simple striking tools and mills, preferably at low temperatures.
  • Cold spray processes known to the person skilled in the art likewise enable comminution up to the desired particle size distribution. Depending on the method used and intended further processing can be set very different particle size distributions.
  • the powder according to the invention makes it possible to dispense emulsifiers with high surface activity, especially of the lecithin type, monoglycerides, diglycerides, polysorbates, sodium stearyl lactylate, glycerol monostearate, lactic acid esters and polyglycerol esters, propylene glycol esters, polyoxyethylene esters, diacetylsuccinic acid esters.
  • the sterol-containing formulations produced by this process can be easily incorporated into foods, in particular milk, milk drinks, whey and yoghurt drinks, margarine, fruit juices, fruit juice mixtures, fruit juice drinks, vegetable juices, carbonated and non-carbonated beverages, soy milk drinks or high-protein liquid diet replacement drinks, and fermented milk preparations.
  • Yogurt, drinking yoghurt, or cheese preparations, cereals and Nutritionbars but also be incorporated into cosmetic or pharmaceutical preparations.
  • Another object of the invention therefore relates to food preparations containing the sterol 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 pulverfbrmigen preparations based on the total weight of the food.
  • 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 resulting ground powder in the form of the supercooled melt had a total sterol content in relation to the free sterol of 81.7% by weight to 20.4% by weight.
  • the milled powder had a total sterol content relative to the free sterol of 89.8 wt% to 59.2 wt%.
  • this powder can only be further processed by very fine grinding in aqueous formulations.
  • Advantageous for incorporation into beverages is a melting range below 100 0 C, since such formulations can be introduced after melting in the heated food and allow easy and simple further processing and a good distribution in the consumer product.
  • the resulting powder was dispersed in milk and water as compared to ground sterols of comparable particle size distribution.
  • about 250 ml of the liquid to be examined were 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.
  • All of the powders of the invention were in cold (15 ° C) and warm (6O 0 C) water, and disperse well in milk (18 ° C), while the untreated free ground sterol was poorly dispersed and located on the liquid surface due to the hydrophobic surface remained , Sensory differences were very great.
  • the powders according to the invention tasted neutral in water and milk and did not occupy the palate and the oral mucous membrane, whereas the untreated powder at the mouth Mucosa adhered and left behind a typical negative stinging taste an unpleasant sensory feeling.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Botany (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicinal Preparation (AREA)
  • Steroid Compounds (AREA)
  • Dairy Products (AREA)
  • Cosmetics (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Fats And Perfumes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une formulation pulvérulente contenant des stérols se présentant sous la forme de matière fondue sous-refroidie de stérols et d'esters de stérols, à condition que la teneur en ester de stérols corresponde à au moins 30% en poids du contenu total de la poudre. L'ester de stérols introduit est un ester d'acide gras comprenant une longueur de chaîne comprise entre 2 et 24, de préférence entre 8 et 12 atomes de carbone. Les préparations à base de stérols peuvent être incorporées facilement, sans coûts techniques importants, dans des aliments, du fait de leur mouillabilité et de leur faible fusion et elles présentent, en particulier dans les boissons, de bonnes propriétés organoleptiques et sensorielles.
EP07711677A 2006-03-08 2007-02-27 Poudre contenant des sterols Withdrawn EP1991070A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006011090 2006-03-08
PCT/EP2007/001657 WO2007101581A2 (fr) 2006-03-08 2007-02-27 Poudre contenant des sterols

Publications (1)

Publication Number Publication Date
EP1991070A2 true EP1991070A2 (fr) 2008-11-19

Family

ID=38468874

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07711677A Withdrawn EP1991070A2 (fr) 2006-03-08 2007-02-27 Poudre contenant des sterols

Country Status (5)

Country Link
US (1) US20100055190A1 (fr)
EP (1) EP1991070A2 (fr)
JP (2) JP5294881B2 (fr)
AU (1) AU2007222697B2 (fr)
WO (1) WO2007101581A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1991070A2 (fr) * 2006-03-08 2008-11-19 Cognis IP Management GmbH Poudre contenant des sterols

Family Cites Families (16)

* 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
JPH03145420A (ja) * 1989-10-30 1991-06-20 Roecar Holdings Nederland Antilles Nv 水溶性が改良された植物および動物ステロールならびにそれらの誘導体
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
JPH06329588A (ja) * 1993-05-19 1994-11-29 Riken Vitamin Co Ltd 水分散性モノグリセリド
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.
DK1298194T3 (da) * 1997-08-22 2006-11-27 Unilever Nv Staniolholdige sammensætninger
US6242001B1 (en) * 1998-11-30 2001-06-05 Mcneil-Ppc, Inc. Method for producing dispersible sterol and stanol compounds
US6267963B1 (en) * 1999-06-02 2001-07-31 Kraft Foods, Inc. Plant sterol-emulsifier complexes
US20050118203A1 (en) * 2002-03-20 2005-06-02 Won-Tae Yoon Mixing powder of plant sterol and emulsifier, and method for preparing the same
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
DE102006041302A1 (de) * 2006-03-08 2007-09-13 Cognis Ip Management Gmbh Sterolester mit kurzkettigen Fettsäuren
EP1991070A2 (fr) * 2006-03-08 2008-11-19 Cognis IP Management GmbH Poudre contenant des sterols

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007101581A2 *

Also Published As

Publication number Publication date
JP5294881B2 (ja) 2013-09-18
AU2007222697A1 (en) 2007-09-13
WO2007101581A3 (fr) 2007-11-08
JP2009529017A (ja) 2009-08-13
JP2013129671A (ja) 2013-07-04
AU2007222697B2 (en) 2012-07-05
WO2007101581A2 (fr) 2007-09-13
US20100055190A1 (en) 2010-03-04

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