EP0607120A1 - Reduction de cholesterol - Google Patents
Reduction de cholesterolInfo
- Publication number
- EP0607120A1 EP0607120A1 EP90915067A EP90915067A EP0607120A1 EP 0607120 A1 EP0607120 A1 EP 0607120A1 EP 90915067 A EP90915067 A EP 90915067A EP 90915067 A EP90915067 A EP 90915067A EP 0607120 A1 EP0607120 A1 EP 0607120A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- cholesterol
- cyclodextrin
- yolk
- emulsion
- milk
- 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- Withdrawn
Links
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title claims abstract description 136
- 235000012000 cholesterol Nutrition 0.000 title claims abstract description 67
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 51
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000000839 emulsion Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000002904 solvent Substances 0.000 claims abstract 2
- 210000002969 egg yolk Anatomy 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 17
- 210000004080 milk Anatomy 0.000 claims description 17
- 235000013336 milk Nutrition 0.000 claims description 16
- 239000008267 milk Substances 0.000 claims description 16
- 102000002322 Egg Proteins Human genes 0.000 claims description 15
- 108010000912 Egg Proteins Proteins 0.000 claims description 15
- 238000010790 dilution Methods 0.000 claims description 12
- 239000012895 dilution Substances 0.000 claims description 12
- 235000013345 egg yolk Nutrition 0.000 claims description 11
- 239000006071 cream Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 238000000265 homogenisation Methods 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims 2
- 238000002203 pretreatment Methods 0.000 claims 2
- 238000004090 dissolution Methods 0.000 claims 1
- 235000013601 eggs Nutrition 0.000 abstract description 16
- 235000013365 dairy product Nutrition 0.000 abstract description 4
- 238000000605 extraction Methods 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 3
- 238000001556 precipitation Methods 0.000 abstract description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 239000001116 FEMA 4028 Substances 0.000 description 12
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 12
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 12
- 229960004853 betadex Drugs 0.000 description 12
- 239000003925 fat Substances 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 235000014103 egg white Nutrition 0.000 description 4
- 210000000969 egg white Anatomy 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000034994 death Effects 0.000 description 3
- 231100000517 death Toxicity 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000020603 homogenised milk Nutrition 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 1
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; MAKING THEREOF
- A23C7/00—Other dairy technology
- A23C7/04—Removing unwanted substances other than lactose or milk proteins from milk
- A23C7/043—Removing unwanted substances other than lactose or milk proteins from milk using chemicals in liquid or solid state, e.g. flocculating, adsorbing or extracting agents
-
- 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
- A23L15/00—Egg products; Preparation or treatment thereof
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
- A23L5/273—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption using adsorption or absorption agents, resins, synthetic polymers, or ion exchangers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Dairy Products (AREA)
Abstract
On enlève le cholestérol présent dans les émulsions aqueuses de produits à base de produits laitiers ou d'oeufs en mettant une cyclodextrine en contact avec les émulsions aqueuses, en formant un complexe cyclodextrine/cholestérol, normalement à une température comprise entre 20 °C et 60 °C, et en provoquant la précipitation du complexe de la solution en la refroidissant à une température au-dessous de 5 °C. Le complexe ainsi précipité est retiré et la cyclodextrine est régénérée par extraction du cholestérol à l'aide d'un solvant choisi parmi des mélanges d'hexane, d'acide acétique ou d'acide acétique/butanol.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPJ830890 | 1990-01-23 | ||
AU8308/90 | 1990-01-23 | ||
AU55112/90A AU630446B2 (en) | 1989-05-19 | 1990-05-17 | Cholesterol removal from eggs, dairy products and other aqueous emulsions |
AU55112/90 | 1990-05-17 | ||
PCT/AU1990/000489 WO1991011114A1 (fr) | 1990-01-23 | 1990-10-12 | Reduction de cholesterol |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0607120A4 EP0607120A4 (fr) | 1992-10-03 |
EP0607120A1 true EP0607120A1 (fr) | 1994-07-27 |
Family
ID=25630776
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90915067A Withdrawn EP0607120A1 (fr) | 1990-01-23 | 1990-10-12 | Reduction de cholesterol |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0607120A1 (fr) |
JP (1) | JPH05505516A (fr) |
CA (1) | CA2071217A1 (fr) |
NZ (1) | NZ235649A (fr) |
WO (1) | WO1991011114A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4313919A1 (de) * | 1993-04-28 | 1994-11-03 | Sueddeutsche Kalkstickstoff | Verfahren zur Entfernung von Cholesterinderivaten aus Eigelb |
IL106581A (en) * | 1993-08-04 | 2000-08-31 | Yissum Res Dev Co | Removal of cholesterol from edibles |
US5484624A (en) * | 1995-03-31 | 1996-01-16 | Board Of Trustees Operating Michigan State University | Method for reduction of cholesterol in egg materials |
US5738898A (en) * | 1995-03-31 | 1998-04-14 | Board Of Trustees Operating Michigan State University | Process for reducing sterols in eggs |
US6110517A (en) * | 1997-08-02 | 2000-08-29 | Se Jong University | Method for removing cholesterol from milk and cream |
WO1999017620A1 (fr) * | 1997-10-06 | 1999-04-15 | Eugene Science Inc. | Procede de reduction de la teneur en cholesterol dans les produits laitiers |
US6129945A (en) * | 1998-12-10 | 2000-10-10 | Michael E. George | Methods to reduce free fatty acids and cholesterol in anhydrous animal fat |
DE102012220689A1 (de) * | 2012-11-13 | 2014-05-15 | Wacker Chemie Ag | Verfahren zur Reduktion des Gehalts an Sterolen in Milch und Rahm |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2601959B1 (fr) * | 1986-07-24 | 1988-12-02 | Monserbio Gie | Procede d'elimination du cholesterol contenu dans une matiere grasse d'origine animale et matiere grasse appauvrie en cholesterol obtenue |
FR2626145B1 (fr) * | 1988-01-22 | 1990-07-06 | Monserbio | Procede d'elimination de composes steroidiques contenus dans une substance d'origine biologique |
-
1990
- 1990-10-12 JP JP90514101A patent/JPH05505516A/ja active Pending
- 1990-10-12 WO PCT/AU1990/000489 patent/WO1991011114A1/fr not_active Application Discontinuation
- 1990-10-12 EP EP90915067A patent/EP0607120A1/fr not_active Withdrawn
- 1990-10-12 NZ NZ235649A patent/NZ235649A/xx unknown
- 1990-10-12 CA CA002071217A patent/CA2071217A1/fr not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO9111114A1 * |
Also Published As
Publication number | Publication date |
---|---|
NZ235649A (en) | 1993-03-26 |
JPH05505516A (ja) | 1993-08-19 |
WO1991011114A1 (fr) | 1991-08-08 |
EP0607120A4 (fr) | 1992-10-03 |
CA2071217A1 (fr) | 1991-07-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 19920709 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE |
|
17Q | First examination report despatched |
Effective date: 19950418 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 19950829 |