CA2537744A1 - Compound and method for enhancing the cholesterol lowering property of plant sterol and stanol esters - Google Patents
Compound and method for enhancing the cholesterol lowering property of plant sterol and stanol esters Download PDFInfo
- Publication number
- CA2537744A1 CA2537744A1 CA002537744A CA2537744A CA2537744A1 CA 2537744 A1 CA2537744 A1 CA 2537744A1 CA 002537744 A CA002537744 A CA 002537744A CA 2537744 A CA2537744 A CA 2537744A CA 2537744 A1 CA2537744 A1 CA 2537744A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- glyceride
- fatty acid
- acid
- plant
- 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.)
- Abandoned
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 226
- 150000001875 compounds Chemical class 0.000 title claims abstract description 133
- 235000002378 plant sterols Nutrition 0.000 title claims abstract description 125
- 235000012000 cholesterol Nutrition 0.000 title claims abstract description 101
- 238000000034 method Methods 0.000 title claims description 40
- 150000002148 esters Chemical class 0.000 title description 39
- 230000002708 enhancing effect Effects 0.000 title description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 127
- 239000000194 fatty acid Substances 0.000 claims abstract description 127
- 229930195729 fatty acid Natural products 0.000 claims abstract description 127
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 127
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 95
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 80
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000008117 stearic acid Substances 0.000 claims abstract description 80
- 230000032050 esterification Effects 0.000 claims abstract description 13
- 238000005886 esterification reaction Methods 0.000 claims abstract description 13
- 241000196324 Embryophyta Species 0.000 claims description 43
- 239000003921 oil Substances 0.000 claims description 34
- 235000019198 oils Nutrition 0.000 claims description 34
- 241001465754 Metazoa Species 0.000 claims description 26
- 239000003638 chemical reducing agent Substances 0.000 claims description 26
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 24
- 235000015278 beef Nutrition 0.000 claims description 20
- -1 di-glyceride Chemical compound 0.000 claims description 20
- 235000019197 fats Nutrition 0.000 claims description 18
- 239000003760 tallow Substances 0.000 claims description 18
- 241000282414 Homo sapiens Species 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 14
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 14
- 230000037406 food intake Effects 0.000 claims description 12
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 12
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 12
- 125000005457 triglyceride group Chemical group 0.000 claims description 12
- 235000014121 butter Nutrition 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000003904 phospholipids Chemical group 0.000 claims description 10
- 235000015872 dietary supplement Nutrition 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 7
- 244000144972 livestock Species 0.000 claims description 7
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 6
- 235000021314 Palmitic acid Nutrition 0.000 claims description 6
- 235000021004 dietary regimen Nutrition 0.000 claims description 6
- 235000020778 linoleic acid Nutrition 0.000 claims description 6
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 6
- 235000004936 Bromus mango Nutrition 0.000 claims description 5
- 235000004863 Fevillea cordifolia Nutrition 0.000 claims description 5
- 244000034902 Fevillea cordifolia Species 0.000 claims description 5
- 241000598860 Garcinia hanburyi Species 0.000 claims description 5
- 235000014826 Mangifera indica Nutrition 0.000 claims description 5
- 235000009184 Spondias indica Nutrition 0.000 claims description 5
- 244000141804 Theobroma grandiflorum Species 0.000 claims description 5
- 229940110456 cocoa butter Drugs 0.000 claims description 5
- 235000019868 cocoa butter Nutrition 0.000 claims description 5
- 229940117709 gamboge Drugs 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 239000002152 aqueous-organic solution Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 241001093152 Mangifera Species 0.000 claims 4
- 239000000126 substance Substances 0.000 abstract description 17
- 210000002249 digestive system Anatomy 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 9
- 229940079593 drug Drugs 0.000 abstract description 9
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 9
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- 230000002195 synergetic effect Effects 0.000 abstract description 6
- 230000002452 interceptive effect Effects 0.000 abstract 1
- 235000013305 food Nutrition 0.000 description 38
- 230000001906 cholesterol absorption Effects 0.000 description 22
- 235000016709 nutrition Nutrition 0.000 description 22
- 230000001965 increasing effect Effects 0.000 description 20
- 239000003925 fat Substances 0.000 description 14
- 235000010469 Glycine max Nutrition 0.000 description 12
- 238000008214 LDL Cholesterol Methods 0.000 description 12
- 244000068988 Glycine max Species 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 10
- 230000035764 nutrition Effects 0.000 description 10
- 241000699800 Cricetinae Species 0.000 description 9
- 239000008158 vegetable oil Substances 0.000 description 9
- 229930182558 Sterol Natural products 0.000 description 8
- 235000005911 diet Nutrition 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 235000003702 sterols Nutrition 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- 201000001320 Atherosclerosis Diseases 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- 230000000378 dietary effect Effects 0.000 description 6
- 208000019622 heart disease Diseases 0.000 description 6
- 150000003432 sterols Chemical class 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 5
- 239000000693 micelle Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 239000003784 tall oil Substances 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 238000002651 drug therapy Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 235000013310 margarine Nutrition 0.000 description 4
- 235000014593 oils and fats Nutrition 0.000 description 4
- 210000000813 small intestine Anatomy 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001131 Pulp (paper) Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000371 Esterases Proteins 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000003529 anticholesteremic agent Substances 0.000 description 2
- 230000003143 atherosclerotic effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 235000015219 food category Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 239000002417 nutraceutical Substances 0.000 description 2
- 235000021436 nutraceutical agent Nutrition 0.000 description 2
- 230000008447 perception Effects 0.000 description 2
- 229940068065 phytosterols Drugs 0.000 description 2
- 239000010773 plant oil Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229950005143 sitosterol Drugs 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- VGSSUFQMXBFFTM-UHFFFAOYSA-N (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol Natural products C1C(O)C2(O)CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 VGSSUFQMXBFFTM-UHFFFAOYSA-N 0.000 description 1
- 102100029470 Apolipoprotein E Human genes 0.000 description 1
- 101710095339 Apolipoprotein E Proteins 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 1
- 241000867607 Chlorocebus sabaeus Species 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- LGJMUZUPVCAVPU-JFBKYFIKSA-N Sitostanol Natural products O[C@@H]1C[C@H]2[C@@](C)([C@@H]3[C@@H]([C@H]4[C@@](C)([C@@H]([C@@H](CC[C@H](C(C)C)CC)C)CC4)CC3)CC2)CC1 LGJMUZUPVCAVPU-JFBKYFIKSA-N 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 235000019007 dietary guidelines Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
- 229960000815 ezetimibe Drugs 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 235000014106 fortified food Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000033227 intestinal cholesterol absorption Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009643 reducing diet Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50078403P | 2003-09-05 | 2003-09-05 | |
| US60/500,784 | 2003-09-05 | ||
| PCT/US2004/029187 WO2005023832A1 (en) | 2003-09-05 | 2004-09-03 | Compound and method for enhancing the cholesterol lowering property of plant sterol and stanol esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2537744A1 true CA2537744A1 (en) | 2005-03-17 |
Family
ID=34272993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002537744A Abandoned CA2537744A1 (en) | 2003-09-05 | 2004-09-03 | Compound and method for enhancing the cholesterol lowering property of plant sterol and stanol esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050085451A1 (enExample) |
| EP (1) | EP1660516A1 (enExample) |
| JP (1) | JP2007504254A (enExample) |
| KR (1) | KR20060083451A (enExample) |
| AU (1) | AU2004270726A1 (enExample) |
| CA (1) | CA2537744A1 (enExample) |
| WO (1) | WO2005023832A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004066938A2 (en) * | 2003-01-28 | 2004-08-12 | University Of Georgia Research Foundation, Inc. | Method and composition for lowering cholesterol |
| ES2748136T3 (es) | 2007-10-15 | 2020-03-13 | United Animal Health Inc | Método para aumentar el rendimiento de las crías |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2025314A1 (en) * | 1989-10-12 | 1991-04-13 | Ronald J. Jandacek | Triglycerides containing saturated fatty acids having 20 to 24 carbon atoms useful in lowering blood cholesterol levels |
| AU664827B2 (en) * | 1991-05-03 | 1995-12-07 | Raisio Benecol Ltd. | A substance for lowering high cholesterol level in serum and a method for preparing the same |
| FI111513B (fi) * | 1998-05-06 | 2003-08-15 | Raisio Benecol Oy | Uudet fytosteroli- ja fytostanolirasvahappoesterikoostumukset, niitä sisältävät tuotteet sekä menetelmät niiden valmistamiseksi |
| US5892068A (en) * | 1998-08-25 | 1999-04-06 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
| EP1180545B2 (en) * | 1999-05-26 | 2018-05-09 | Adeka Corporation | Vegetable sterol-containing fat compositions and process for producing the same |
| DE50011218D1 (de) * | 1999-06-25 | 2005-10-27 | Cognis Ip Man Gmbh | Verwendung von nanoskaligen sterolen und sterolestern |
| AU782264B2 (en) * | 1999-11-05 | 2005-07-14 | Raisio Benecol Oy | Edible fat blends |
| DE60132508T2 (de) * | 2000-01-31 | 2008-04-30 | Härting S.A. | Zusammensetzungen enthaltend Phytosterol- und Policosanolester von Fettsäuren zur Herabsetzung des Cholesterol- und Triglyceridspiegels |
| JP4911815B2 (ja) * | 2000-04-28 | 2012-04-04 | 株式会社Ａｄｅｋａ | 植物ステロール含有油脂組成物 |
| IL147942A0 (en) * | 2002-01-31 | 2002-08-14 | Enzymotec Ltd | Method of fractionation of phytosterol esters in oil and products obtained thereby |
| JP2003246746A (ja) * | 2002-02-25 | 2003-09-02 | Kurabo Ind Ltd | リパーゼ阻害剤およびリパーゼ阻害作用を有する加工食品 |
-
2004
- 2004-09-03 EP EP04783435A patent/EP1660516A1/en not_active Withdrawn
- 2004-09-03 JP JP2006525530A patent/JP2007504254A/ja active Pending
- 2004-09-03 AU AU2004270726A patent/AU2004270726A1/en not_active Abandoned
- 2004-09-03 US US10/934,346 patent/US20050085451A1/en not_active Abandoned
- 2004-09-03 WO PCT/US2004/029187 patent/WO2005023832A1/en not_active Ceased
- 2004-09-03 CA CA002537744A patent/CA2537744A1/en not_active Abandoned
- 2004-09-03 KR KR1020067004617A patent/KR20060083451A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060083451A (ko) | 2006-07-20 |
| WO2005023832A1 (en) | 2005-03-17 |
| US20050085451A1 (en) | 2005-04-21 |
| JP2007504254A (ja) | 2007-03-01 |
| EP1660516A1 (en) | 2006-05-31 |
| AU2004270726A1 (en) | 2005-03-17 |
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