CA2245482A1 - Process for the preparation of stanol esters, and use thereof - Google Patents

Process for the preparation of stanol esters, and use thereof

Info

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
Application number
CA002245482A
Other languages
French (fr)
Other versions
CA2245482C (en
Inventor
Marnix P. Van Amerongen
Lourus Cornelis Lievense
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.)
Unilever PLC
Original Assignee
Unilever PLC
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 Unilever PLC filed Critical Unilever PLC
Publication of CA2245482A1 publication Critical patent/CA2245482A1/en
Application granted granted Critical
Publication of CA2245482C publication Critical patent/CA2245482C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01Other fatty acid esters, e.g. phosphatides
    • A23D7/013Spread compositions
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/015Reducing calorie content; Reducing fat content, e.g. "halvarines"
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013Other fatty acid esters, e.g. phosphatides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/60Salad dressings; Mayonnaise; Ketchup
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11Plant sterols or derivatives thereof, e.g. phytosterols
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12Fatty acids or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10Ester 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.
CA002245482A 1997-08-22 1998-08-21 Process for the preparation of stanol esters, and use thereof Expired - Fee Related CA2245482C (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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

Similar Documents

Publication Publication Date Title
CA2245482A1 (en) Process for the preparation of stanol esters, and use thereof
CA2245466A1 (en) Stanol ester composition and production thereof
CA2246017A1 (en) Stanol comprising compositions
MY110765A (en) Compositions containing cholesteryl esters of unsaturated fatty acids
NZ508578A (en) Fatty acid esters of phytosterol or phytostanol containing compositions useful in food products
CA2119795A1 (en) Process for the preparation of highly esterified alkoxylated polyol compositions
EP1025842A4 (en) Capsular preparation containing unsaturated fatty acid or derivative thereof and process for producing the same
AU6912994A (en) Catalyst and process for using same for the preparation of unsaturated carboxylic acid esters
PL323176A1 (en) Esters of fatty acids as biologically active compounds
EP0823475A4 (en) Novel microorganisms capable of producing highly unsaturated fatty acids and process for producing highly unsaturated fatty acids by using the microorganisms
FI20090166A (en) Process for preparing a beta-sitostanol fatty acid ester or ester mixture
WO1998001126A3 (en) Method of manufacturing a sterol ester mixture
CA2071220A1 (en) Selective esterification of long chain fatty acid monoglycerides with medium chain fatty acids
EP0334154A3 (en) Method for the continiuous esterification of fatty acids
AU1916388A (en) Process for the preparation of polyol fatty acid esters
DE69015591T2 (en) Process for the preparation of esters of unsaturated carboxylic acids.
CA2096044A1 (en) Reduced calorie cocoa butter substitutes
AU1808295A (en) Hydrogenation of unsaturated fats, fatty acids or fatty acid esters
CA2201931A1 (en) Mixture of phospholipid-containing fats and lcp fatty acids
EP0245076A3 (en) Edible fats
AU1846597A (en) Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds
HK1043605A1 (en) Method for obtaining an oil that is rich in hydroxyoctadecadienoic fatty acids(hode) or the esters thereof from a mixture containing linoleic acid or the esters thereof
IL78973A (en) Emulsifier,method for its preparation and product containing it
CA2146141A1 (en) Triglyceride fractionation
AU4480989A (en) Process for producing alkyl glycoside fatty acid polyester fat substitutes and products produced by the process

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed