CA2245482A1 - Process for the preparation of stanol esters, and use thereof - Google Patents
Process for the preparation of stanol esters, and use thereofInfo
- Publication number
- CA2245482A1 CA2245482A1 CA002245482A CA2245482A CA2245482A1 CA 2245482 A1 CA2245482 A1 CA 2245482A1 CA 002245482 A CA002245482 A CA 002245482A CA 2245482 A CA2245482 A CA 2245482A CA 2245482 A1 CA2245482 A1 CA 2245482A1
- Authority
- CA
- Canada
- Prior art keywords
- fatty acid
- acid esters
- stanol
- preparation
- groups
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 title 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 8
- 229930195729 fatty acid Natural products 0.000 abstract 8
- 239000000194 fatty acid Substances 0.000 abstract 8
- -1 fatty acid esters Chemical class 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 3
- 229930182558 Sterol Natural products 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 abstract 2
- 235000003702 sterols Nutrition 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000005313 fatty acid group Chemical group 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 238000009884 interesterification Methods 0.000 abstract 1
- 229940068065 phytosterols Drugs 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- 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
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
-
- 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
- A23D7/015—Reducing calorie content; Reducing fat content, e.g. "halvarines"
-
- 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
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, 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 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
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/60—Salad dressings; Mayonnaise; Ketchup
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
-
- 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
-
- 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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Abstract
The invention concerns a process for the preparation of stanol fatty acid esters mixtures by interesterification of stanol fatty acid esters starting material, of which at least 500 of the fatty acid groups are saturated, with fatty acid mixtures containing at least 350, and preferably at least 45%, of poly unsaturated fatty acid (PUFA) groups, and wherein preferably the hardening of sterol fatty acid esters. The sterol fatty acid esters are preferably prepared by the esterification of phytosterols with a fatty acid ester mixture comprising at least 700 of C18 fatty acids, all steps can be carried out in the absence of a solvent.
Also claimed are food products comprising the stanol fatty acid esters obtained by the process.
Also claimed are food products comprising the stanol fatty acid esters obtained by the process.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB97202597.7 | 1997-08-22 | ||
EP97202597 | 1997-08-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2245482A1 true CA2245482A1 (en) | 1999-02-22 |
CA2245482C CA2245482C (en) | 2004-11-23 |
Family
ID=8228668
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002245482A Expired - Fee Related CA2245482C (en) | 1997-08-22 | 1998-08-21 | Process for the preparation of stanol esters, and use thereof |
Country Status (7)
Country | Link |
---|---|
US (1) | US6106886A (en) |
EP (1) | EP0897970B1 (en) |
CA (1) | CA2245482C (en) |
DE (1) | DE69826592T2 (en) |
DK (1) | DK0897970T3 (en) |
ES (1) | ES2229443T3 (en) |
ZA (1) | ZA987540B (en) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA69378C2 (en) | 1996-11-04 | 2004-09-15 | Райзіо Бенекол Лтд. | Texturizing compositions to be used in fat mixtures in food products |
US6929816B2 (en) | 1998-01-21 | 2005-08-16 | Raisio Benecol Ltd. | Fat compositions for use in food |
FI111513B (en) | 1998-05-06 | 2003-08-15 | Raisio Benecol Oy | Novel compositions of phytosterol and phytostanol fatty acid esters, products containing them and processes for their preparation |
US5892068A (en) * | 1998-08-25 | 1999-04-06 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
NZ333817A (en) | 1998-08-25 | 2000-09-29 | Mcneil Ppc Inc | Process for preparing stanol/sterol fatty acid esters such as beta sitosterol fatty acid esters, useful in reducing cholesterol levels |
US6123978A (en) | 1998-08-31 | 2000-09-26 | Mcneil-Ppc, Inc. | Stable salad dressings |
US6277431B1 (en) * | 1998-10-14 | 2001-08-21 | Redeem, Inc. | Anticholesterolemic edible oil |
US6274574B1 (en) | 1999-02-26 | 2001-08-14 | Kraft Foods, Inc. | Use of mesophase-stabilized compositions for delivery of cholesterol-reducing sterols and stanols in food products |
US6410758B2 (en) | 1999-05-24 | 2002-06-25 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
EP1211955A1 (en) * | 1999-08-30 | 2002-06-12 | Ocean Nutrition Canada Ltd. | A nutritional supplement for lowering serum triglyceride and cholesterol levels |
US6998501B1 (en) | 1999-08-30 | 2006-02-14 | Ocean Nutrition Canada Limited | Nutritional supplement for lowering serum triglyceride and cholesterol levels |
US6413571B1 (en) * | 1999-10-21 | 2002-07-02 | The Board Of Regents For Oklahoma State University | Sterol esters of conjugated linoleic acids and process for their production |
BR0015133B1 (en) | 1999-11-05 | 2012-11-27 | edible oil mixtures. | |
IL133969A0 (en) * | 2000-01-10 | 2001-04-30 | Thixo Ltd | Thixotropic compositions containing unsaturated oils and food products containing the same |
IL133968A0 (en) * | 2000-01-10 | 2001-04-30 | Thixo Ltd | Therapeutic oils and edible pastes containing the same |
US20020016317A1 (en) * | 2000-03-27 | 2002-02-07 | Schul David Allen | Sterol ester compositions |
CN1436047A (en) | 2000-04-14 | 2003-08-13 | 马尔斯公司 | Compositions and methods for improving vascular health |
US6495188B2 (en) * | 2000-12-13 | 2002-12-17 | Arco Chemical Technology L.P. | Plastic and semisolid edible shortening products with reduced trans-fatty acid content |
SE523094C2 (en) * | 2001-01-11 | 2004-03-30 | Karlshamns Ab | Process for the preparation of a fat composition containing sterol esters, free sterols and glycerides, fat composition prepared by the process and use of the fat composition |
US6787151B2 (en) * | 2001-08-10 | 2004-09-07 | Lipton, Division Of Conopco, Inc. | Composition for lowering blood cholesterol |
US7144595B2 (en) | 2001-11-16 | 2006-12-05 | Brandeis University | Prepared foods containing triglyceride-recrystallized non-esterified phytosterols |
EP1453386B9 (en) * | 2001-11-16 | 2010-06-23 | Brandeis University | Prepared foods containing triglyceride-recrystallized non-esterified phytosterols |
US20030129253A1 (en) * | 2002-01-03 | 2003-07-10 | Milley Christopher J. | Stable aqueous suspension |
IL147942A0 (en) * | 2002-01-31 | 2002-08-14 | Enzymotec Ltd | Method of fractionation of phytosterol esters in oil and products obtained thereby |
US6974592B2 (en) | 2002-04-11 | 2005-12-13 | Ocean Nutrition Canada Limited | Encapsulated agglomeration of microcapsules and method for the preparation thereof |
KR101175774B1 (en) | 2002-11-04 | 2012-08-21 | 오션 뉴트리션 캐나다 리미티드 | Microcapsules having multiple shells and method for the preparation thereof |
IL155136A0 (en) * | 2003-02-10 | 2003-10-31 | Enzymotec Ltd | A composition for reducing blood cholesterol and triglycerides |
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 |
ZA200600076B (en) | 2003-07-17 | 2007-03-28 | Unilever Plc | Process for the preparation of an edible dispersion comprising oil and structuring agent |
US8158184B2 (en) * | 2004-03-08 | 2012-04-17 | Bunge Oils, Inc. | Structured lipid containing compositions and methods with health and nutrition promoting characteristics |
US20090232916A1 (en) * | 2004-08-09 | 2009-09-17 | Avidor Shulman | Food products for diabetics |
AU2005270831B2 (en) | 2004-08-10 | 2011-08-25 | Enzymotec Ltd. | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
US8034450B2 (en) | 2005-01-21 | 2011-10-11 | Ocean Nutrition Canada Limited | Microcapsules and emulsions containing low bloom gelatin and methods of making and using thereof |
WO2006087093A1 (en) | 2005-02-17 | 2006-08-24 | Unilever N.V. | Process for the preparation of a spreadable dispersion comprising sterol |
US9968120B2 (en) | 2006-05-17 | 2018-05-15 | Dsm Nutritional Products Ag | Homogenized formulations containing microcapsules and methods of making and using thereof |
US7575768B2 (en) * | 2005-09-07 | 2009-08-18 | Brandeis University | Dietary supplements and prepared foods containing triglyceride-recrystallized non-esterified phytosterols |
US20070087085A1 (en) * | 2005-10-17 | 2007-04-19 | Bunge Oils, Inc. | Protein-containing food product and coating for a food product and method of making same |
US20080113067A1 (en) * | 2005-10-17 | 2008-05-15 | Monoj Sarma | Protein-Containing Food Product and Coating for a Food Product and Method of Making Same |
US7678399B2 (en) | 2005-12-05 | 2010-03-16 | Bunge Oils, Inc. | Phytosterol containing deep-fried foods and methods with health promoting characteristics |
US20070148311A1 (en) * | 2005-12-22 | 2007-06-28 | Bunge Oils, Inc. | Phytosterol esterification product and method of make same |
NZ596403A (en) | 2006-06-05 | 2013-02-22 | Ocean Nutrition Canada Ltd | Microcapsules with improved shells with wax in the outer shell |
CA2675123C (en) | 2007-01-10 | 2017-04-11 | Ocean Nutrition Canada Limited | Vegetarian microcapsules |
US7790495B2 (en) * | 2007-10-26 | 2010-09-07 | International Business Machines Corporation | Optoelectronic device with germanium photodetector |
EP2367434B8 (en) | 2008-12-19 | 2017-07-26 | Unilever N.V. | Edible fat powders |
US20100166921A1 (en) * | 2008-12-29 | 2010-07-01 | Conopco, Inc., D/B/A Unilever | Coating |
US20110223312A1 (en) * | 2009-11-30 | 2011-09-15 | Daniel Perlman | Triglyceride-encapsulated phytosterol microparticles dispersed in beverages |
US8512794B2 (en) * | 2010-05-20 | 2013-08-20 | Perlman Consulting, Llc | Oleate ester phytosterol compositions |
WO2011160921A1 (en) | 2010-06-22 | 2011-12-29 | Unilever Nv | Edible fat powders |
CA2820354C (en) | 2010-12-17 | 2019-06-11 | Unilever Plc | Process of compacting a microporous fat powder and compacted fat powder so obtained |
EP2651229B1 (en) | 2010-12-17 | 2015-04-08 | Unilever N.V. | Edible water in oil emulsion |
CA2822523C (en) * | 2010-12-22 | 2019-03-12 | Unilever Plc | Edible fat continuous emulsion comprising plant sterol esters |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2248921C3 (en) * | 1972-10-05 | 1981-11-12 | Harburger Oelwerke Brinckman & Mergell, 2100 Hamburg | Process for the production of a mixture of vegetable and animal oils or fats and fatty acid ester esters |
JPS6255040A (en) * | 1985-09-05 | 1987-03-10 | Nisshin Oil Mills Ltd:The | Production of margarine or shortening |
PL166991B1 (en) * | 1991-05-03 | 1995-07-31 | Raision Margariini Oy | Substance for lowering cholesterol level in blood serum and method of obtaining same |
AU3442497A (en) * | 1996-07-05 | 1998-02-02 | Unilever Plc | Method of manufacturing an ester mixture |
FI107015B (en) * | 1996-08-09 | 2001-05-31 | Raisio Benecol Oy | Mixture of vegetable stanol fatty acid esters and their use in food |
UA69378C2 (en) * | 1996-11-04 | 2004-09-15 | Райзіо Бенекол Лтд. | Texturizing compositions to be used in fat mixtures in food products |
US5929062A (en) * | 1997-06-19 | 1999-07-27 | University Of Western Ontario | Oxysterol inhibition of dietary cholesterol uptake |
DE69827330T2 (en) * | 1997-08-22 | 2006-02-02 | Unilever N.V. | Stanol ester-containing composition |
US6025348A (en) * | 1998-04-30 | 2000-02-15 | Kao Corporation | Oil and fat composition containing phytosterol |
US5932562A (en) * | 1998-05-26 | 1999-08-03 | Washington University | Sitostanol formulation to reduce cholesterol absorption and method for preparing and use of same |
US5892068A (en) * | 1998-08-25 | 1999-04-06 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
-
1998
- 1998-07-31 DK DK98202588T patent/DK0897970T3/en active
- 1998-07-31 EP EP98202588A patent/EP0897970B1/en not_active Expired - Lifetime
- 1998-07-31 DE DE69826592T patent/DE69826592T2/en not_active Expired - Fee Related
- 1998-07-31 ES ES98202588T patent/ES2229443T3/en not_active Expired - Lifetime
- 1998-08-18 US US09/135,722 patent/US6106886A/en not_active Expired - Fee Related
- 1998-08-20 ZA ZA9807540A patent/ZA987540B/en unknown
- 1998-08-21 CA CA002245482A patent/CA2245482C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0897970B1 (en) | 2004-09-29 |
US6106886A (en) | 2000-08-22 |
DE69826592D1 (en) | 2004-11-04 |
EP0897970A1 (en) | 1999-02-24 |
CA2245482C (en) | 2004-11-23 |
ZA987540B (en) | 2000-02-21 |
DK0897970T3 (en) | 2004-11-08 |
ES2229443T3 (en) | 2005-04-16 |
DE69826592T2 (en) | 2006-02-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |