NO314357B1 - Fytosterol og/eller fytosterolderivater - Google Patents
Fytosterol og/eller fytosterolderivater Download PDFInfo
- Publication number
- NO314357B1 NO314357B1 NO19995784A NO995784A NO314357B1 NO 314357 B1 NO314357 B1 NO 314357B1 NO 19995784 A NO19995784 A NO 19995784A NO 995784 A NO995784 A NO 995784A NO 314357 B1 NO314357 B1 NO 314357B1
- Authority
- NO
- Norway
- Prior art keywords
- esters
- mixture
- phytosterol
- phytosterols
- beta
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 62
- 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 claims description 43
- 150000002148 esters Chemical class 0.000 claims description 42
- 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 claims description 39
- 229940068065 phytosterols Drugs 0.000 claims description 34
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 29
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 22
- 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 claims description 21
- 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 claims description 19
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 19
- 235000005911 diet Nutrition 0.000 claims description 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 17
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 17
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 17
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 17
- 229930195729 fatty acid Natural products 0.000 claims description 17
- 239000000194 fatty acid Substances 0.000 claims description 17
- 230000037213 diet Effects 0.000 claims description 16
- 235000016831 stigmasterol Nutrition 0.000 claims description 16
- 229940032091 stigmasterol Drugs 0.000 claims description 16
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims description 16
- -1 sodium alkoxide Chemical class 0.000 claims description 14
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 13
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims description 12
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 12
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol 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)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 12
- 229950005143 sitosterol Drugs 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 11
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 10
- 235000013305 food Nutrition 0.000 claims description 9
- 229940076810 beta sitosterol Drugs 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003626 triacylglycerols Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims description 6
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol 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)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 6
- 235000000431 campesterol Nutrition 0.000 claims description 6
- 238000009884 interesterification Methods 0.000 claims description 6
- 210000002966 serum Anatomy 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002194 fatty esters Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- ARYTXMNEANMLMU-UHFFFAOYSA-N 24alpha-methylcholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(C)C(C)C)C1(C)CC2 ARYTXMNEANMLMU-UHFFFAOYSA-N 0.000 claims description 4
- BBTIMXAYZRWPNG-UHFFFAOYSA-N 3beta,Delta4-stigmasten-3-ol Natural products C1CC2=CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BBTIMXAYZRWPNG-UHFFFAOYSA-N 0.000 claims description 4
- 241000282412 Homo Species 0.000 claims description 4
- QADVIPISOOQJMJ-WLKYTNTRSA-N beta-stigmasterol Natural products CCC(CC)C=C[C@@H](C)[C@H]1CC[C@@H]2[C@@H]1CC[C@H]3[C@H]2CC=C4C[C@@H](O)CC[C@]34C QADVIPISOOQJMJ-WLKYTNTRSA-N 0.000 claims description 4
- ARYTXMNEANMLMU-ATEDBJNTSA-N campestanol 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](C)C(C)C)[C@@]2(C)CC1 ARYTXMNEANMLMU-ATEDBJNTSA-N 0.000 claims description 4
- 125000005456 glyceride group Chemical group 0.000 claims description 4
- HCXVJBMSMIARIN-UHFFFAOYSA-N stigmasterol Chemical compound C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 HCXVJBMSMIARIN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 3
- 235000015872 dietary supplement Nutrition 0.000 claims description 3
- 235000006486 human diet Nutrition 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229930182558 Sterol Natural products 0.000 description 16
- 235000003702 sterols Nutrition 0.000 description 16
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 12
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 12
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 12
- 235000012000 cholesterol Nutrition 0.000 description 12
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol 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)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 12
- 150000003432 sterols Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 5
- 229940075999 phytosterol ester Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=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)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 4
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 4
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 4
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 4
- 102000015779 HDL Lipoproteins Human genes 0.000 description 4
- 108010010234 HDL Lipoproteins Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 235000015500 sitosterol Nutrition 0.000 description 4
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000008214 LDL Cholesterol Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000008162 cooking oil Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229940000640 docosahexaenoate Drugs 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
- 235000012631 food intake Nutrition 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 235000013310 margarine Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 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 2
- 229920000064 Ethyl eicosapentaenoic acid Polymers 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 229940045348 brown mixture Drugs 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 230000001278 effect on cholesterol Effects 0.000 description 2
- 229940066279 eicosapentaenoate Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000009200 high fat diet Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-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
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 208000031288 Combined hyperlipidaemia Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 108010069201 VLDL Cholesterol Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 235000020940 control diet Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ITNKVODZACVXDS-YATCGRJWSA-N ethyl (4e,7e,10e,13e,16e,19e)-docosa-4,7,10,13,16,19-hexaenoate Chemical compound CCOC(=O)CC\C=C\C\C=C\C\C=C\C\C=C\C\C=C\C\C=C\CC ITNKVODZACVXDS-YATCGRJWSA-N 0.000 description 1
- SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 229960002600 icosapent ethyl Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 229940012843 omega-3 fatty acid Drugs 0.000 description 1
- 239000006014 omega-3 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].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-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000019195 vitamin supplement Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
-
- 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
- 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Botany (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Wood Science & Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Edible Oils And Fats (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98122412 | 1998-11-26 | ||
EP99119337 | 1999-09-29 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO995784D0 NO995784D0 (no) | 1999-11-25 |
NO995784L NO995784L (no) | 2000-05-29 |
NO314357B1 true NO314357B1 (no) | 2003-03-10 |
Family
ID=26149828
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19995784A NO314357B1 (no) | 1998-11-26 | 1999-11-25 | Fytosterol og/eller fytosterolderivater |
Country Status (17)
Country | Link |
---|---|
US (4) | US20020160990A1 (de) |
EP (1) | EP1004594B1 (de) |
JP (1) | JP2000159792A (de) |
KR (1) | KR100678831B1 (de) |
CN (2) | CN1272011C (de) |
AR (1) | AR025141A1 (de) |
AT (1) | ATE246704T1 (de) |
AU (1) | AU762539B2 (de) |
BR (1) | BR9905398A (de) |
CA (1) | CA2290331C (de) |
DE (1) | DE69910152T2 (de) |
DK (1) | DK1004594T3 (de) |
ES (1) | ES2204052T3 (de) |
ID (1) | ID24148A (de) |
MX (1) | MX215122B (de) |
NO (1) | NO314357B1 (de) |
NZ (1) | NZ501169A (de) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6388069B1 (en) * | 1999-02-10 | 2002-05-14 | Eastman Chemical Company | Corn fiber for the production of advanced chemicals and materials:arabinoxylan and arabinoxylan derivatives made therefrom |
US6998501B1 (en) * | 1999-08-30 | 2006-02-14 | Ocean Nutrition Canada Limited | Nutritional supplement for lowering serum triglyceride and cholesterol levels |
WO2001015552A1 (en) * | 1999-08-30 | 2001-03-08 | Ocean Nutrition Canada Ltd. | A nutritional supplement for lowering serum triglyceride and cholesterol levels |
US6838098B2 (en) | 2000-09-07 | 2005-01-04 | Cadbury Adams Usa, Llc | Continuous formation of center filled gum |
SE523094C2 (sv) * | 2001-01-11 | 2004-03-30 | Karlshamns Ab | Förfarande för framställning av en fettkomposition som innehåller sterolestrar, fria steroler och glycerider, fettkomposition framställd genom förfarandet samt fettkompositionens användning |
US6623266B2 (en) | 2001-01-19 | 2003-09-23 | Cadbury Adams Usa Llc | Apparatus for making a center-filled gum lollipop with hard candy shell |
KR100440613B1 (ko) * | 2001-04-20 | 2004-08-16 | 주식회사 유엘바이오텍 | 식물성스테롤과 생 플라보노이드의 결합체를 이용한 혈중콜레스테롤 저하제의 제조방법과 이에 의해 제조한 혈중콜레스테롤 저하제 |
KR20020081834A (ko) * | 2001-04-20 | 2002-10-30 | 주식회사 유엘바이오텍 | 식물성 스테롤의 유도체를 이용한 혈중 콜레스테롤저하제의 제조방법 및 이에 의해 제조된 혈중 콜레스테롤저하제 |
EP1275309A1 (de) * | 2001-07-13 | 2003-01-15 | Ikeda Food Research Co. Ltd. | Sterol Fettsäure Ester Zusammensetzung und diese enthaltende Lebensmittel |
WO2003009854A1 (en) * | 2001-07-20 | 2003-02-06 | Lonza Ag | Lipid lowering composition comprising carnitine and phytosterol |
FI20012553A0 (fi) * | 2001-12-21 | 2001-12-21 | Raisio Benecol Oy | Syötävät koostumukset |
JP2005529109A (ja) * | 2002-04-10 | 2005-09-29 | カーギル,インコーポレイティド | 水性分散性ステリル・エステル組成物 |
US8821915B2 (en) | 2002-08-09 | 2014-09-02 | Veroscience, Llc | Therapeutic process for the treatment of the metabolic syndrome and associated metabolic disorders |
US20040081678A1 (en) * | 2002-08-09 | 2004-04-29 | Anthony Cincotta | Therapeutic process for the treatment of obesity and associated metabolic disorders |
WO2004091603A1 (fr) * | 2003-04-07 | 2004-10-28 | Clinigenetics | Utilisation d’un ester de dha pour le traitement des malades cardiovasculaires |
EP1466597A1 (de) * | 2003-04-07 | 2004-10-13 | Clinigenetics | Verwendung von dha-Esteren in der Behandlung kardiovasculärer Krankheiten |
KR101054913B1 (ko) * | 2003-12-31 | 2011-08-05 | 주식회사 삼양제넥스 | 식물스테롤, 헤스페리딘 및 루틴을 포함하는 고지혈증,동맥경화증 및 간질환 예방 및 치료용 조성물 |
US8158184B2 (en) * | 2004-03-08 | 2012-04-17 | Bunge Oils, Inc. | Structured lipid containing compositions and methods with health and nutrition promoting characteristics |
US7727565B2 (en) | 2004-08-25 | 2010-06-01 | Cadbury Adams Usa Llc | Liquid-filled chewing gum composition |
US7678399B2 (en) | 2005-12-05 | 2010-03-16 | Bunge Oils, Inc. | Phytosterol containing deep-fried foods and methods with health promoting characteristics |
MX2008012522A (es) | 2006-04-05 | 2008-10-10 | Cadbury Adams Usa Llc | Complejo de fosfato de calcio en confiterias que contienen acido. |
JP5529529B2 (ja) | 2006-04-05 | 2014-06-25 | インターコンチネンタル グレート ブランズ エルエルシー | 口腔輸送システムに用いるリン酸カルシウム錯体及び塩 |
US20070298079A1 (en) * | 2006-06-26 | 2007-12-27 | Tropicana Products, Inc. | Food fortified with omega-3 fatty acids |
CN101478885A (zh) | 2006-06-29 | 2009-07-08 | 吉百利亚当斯美国有限责任公司 | 改进的用于连续成型中心填充胶基糖块的链式切割机 |
GB0905367D0 (en) * | 2009-03-27 | 2009-05-13 | Danisco | Method |
US9352025B2 (en) | 2009-06-05 | 2016-05-31 | Veroscience Llc | Combination of dopamine agonists plus first phase insulin secretagogues for the treatment of metabolic disorders |
CN101919537B (zh) * | 2010-09-09 | 2012-08-08 | 浙江大学 | 植物甾烷醇酯和共轭亚油酸酯在功能性肉制品中的应用 |
FI123374B (fi) * | 2011-03-25 | 2013-03-15 | Ravintoraisio Oy | Uusi syötävä koostumus |
CN102318686B (zh) * | 2011-06-01 | 2012-12-19 | 黑龙江省大豆技术开发研究中心 | 一种制备含有植物甾醇酯的功能性保健油脂的方法 |
CN102603846A (zh) * | 2012-02-03 | 2012-07-25 | 江南大学 | 一种离子液体中植物甾醇酯的制备方法 |
CN103242407A (zh) * | 2013-05-15 | 2013-08-14 | 张雅茹 | 含多不饱和脂肪酰基的磷脂酰甾醇和/或磷脂酰甾烷醇及制备方法和应用 |
IL237290A0 (en) * | 2015-02-17 | 2015-06-30 | Enzymotec Ltd | Oil mixtures for use in formulas |
CN107530358B (zh) * | 2015-04-23 | 2021-08-06 | 巴斯夫欧洲公司 | 含有甾醇和增溶剂的凝胶胶囊 |
CN109200061A (zh) * | 2017-06-29 | 2019-01-15 | 四川国为制药有限公司 | 一种高纯度鱼油与植物甾醇酯的降血脂组合物 |
WO2020259493A1 (en) * | 2019-06-24 | 2020-12-30 | Basf Se | Compositions and methods for the prevention or treatment, or dietary management of nafld |
CN113197310A (zh) * | 2021-05-21 | 2021-08-03 | 江苏越红生物科技有限公司 | 一种富含油酸的植物甾醇酯的制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE30910E (en) * | 1971-03-19 | 1982-04-20 | Intellectual Property Development Corporation | Reducing cholesterol levels |
US4588717A (en) * | 1984-06-13 | 1986-05-13 | David C. Mitchell Medical Research Institute | Compounds and vitamin supplements and methods for making same |
CA2102112C (en) * | 1991-05-03 | 2010-04-13 | Tatu Miettinen | A substance for lowering high cholesterol level in serum and a method for preparing the same |
US5593691A (en) * | 1993-06-03 | 1997-01-14 | Marigen S.A. | Biotenside solvents for pharmaceuticals and cosmetics |
FI107015B (fi) * | 1996-08-09 | 2001-05-31 | Raisio Benecol Oy | Kasvistanolirasvahappoestereiden seos ja sen käyttö sekä elintarvike |
WO2000004887A2 (en) * | 1998-07-20 | 2000-02-03 | Forbes Medi-Tech Inc. | Compositions comprising phytosterol, phytostanol or mixtures of both and omega-3 fatty acids or derivatives thereof and use of the composition in treating or preventing cardiovascular disease and other disorders |
US5892068A (en) * | 1998-08-25 | 1999-04-06 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
-
1999
- 1999-11-18 ID IDP991068A patent/ID24148A/id unknown
- 1999-11-18 NZ NZ501169A patent/NZ501169A/en not_active IP Right Cessation
- 1999-11-19 CA CA002290331A patent/CA2290331C/en not_active Expired - Fee Related
- 1999-11-19 DK DK99122978T patent/DK1004594T3/da active
- 1999-11-19 MX MX9910678A patent/MX215122B/es not_active IP Right Cessation
- 1999-11-19 AT AT99122978T patent/ATE246704T1/de not_active IP Right Cessation
- 1999-11-19 EP EP99122978A patent/EP1004594B1/de not_active Revoked
- 1999-11-19 ES ES99122978T patent/ES2204052T3/es not_active Expired - Lifetime
- 1999-11-19 DE DE69910152T patent/DE69910152T2/de not_active Revoked
- 1999-11-22 JP JP11330770A patent/JP2000159792A/ja not_active Withdrawn
- 1999-11-23 KR KR1019990052052A patent/KR100678831B1/ko not_active IP Right Cessation
- 1999-11-23 US US09/448,356 patent/US20020160990A1/en not_active Abandoned
- 1999-11-24 AR ARP990105983A patent/AR025141A1/es unknown
- 1999-11-25 AU AU60655/99A patent/AU762539B2/en not_active Ceased
- 1999-11-25 NO NO19995784A patent/NO314357B1/no not_active IP Right Cessation
- 1999-11-25 BR BR9905398-5A patent/BR9905398A/pt not_active Application Discontinuation
- 1999-11-26 CN CNB2003101154954A patent/CN1272011C/zh not_active Expired - Fee Related
- 1999-11-26 CN CNB99124382XA patent/CN1135234C/zh not_active Expired - Fee Related
-
2001
- 2001-11-20 US US09/989,554 patent/US20020055493A1/en not_active Abandoned
-
2005
- 2005-07-25 US US11/189,667 patent/US20050261259A1/en not_active Abandoned
-
2006
- 2006-12-04 US US11/634,032 patent/US20070078115A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CA2290331A1 (en) | 2000-05-26 |
BR9905398A (pt) | 2000-08-08 |
ID24148A (id) | 2000-07-13 |
AU6065599A (en) | 2000-06-01 |
CN1256277A (zh) | 2000-06-14 |
AR025141A1 (es) | 2002-11-13 |
CA2290331C (en) | 2008-01-15 |
DE69910152D1 (de) | 2003-09-11 |
US20050261259A1 (en) | 2005-11-24 |
EP1004594A1 (de) | 2000-05-31 |
NZ501169A (en) | 2001-05-25 |
CN1494909A (zh) | 2004-05-12 |
KR20000035619A (ko) | 2000-06-26 |
US20020160990A1 (en) | 2002-10-31 |
CN1272011C (zh) | 2006-08-30 |
US20070078115A1 (en) | 2007-04-05 |
MX215122B (en) | 2003-07-08 |
MX9910678A (en) | 2000-04-30 |
JP2000159792A (ja) | 2000-06-13 |
NO995784D0 (no) | 1999-11-25 |
EP1004594B1 (de) | 2003-08-06 |
CN1135234C (zh) | 2004-01-21 |
DK1004594T3 (da) | 2003-11-17 |
NO995784L (no) | 2000-05-29 |
AU762539B2 (en) | 2003-06-26 |
DE69910152T2 (de) | 2004-06-09 |
KR100678831B1 (ko) | 2007-02-05 |
ES2204052T3 (es) | 2004-04-16 |
US20020055493A1 (en) | 2002-05-09 |
ATE246704T1 (de) | 2003-08-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO314357B1 (no) | Fytosterol og/eller fytosterolderivater | |
MXPA99010678A (en) | Phytosterol and / or phytostate derivatives | |
AU758747B2 (en) | Phytosterol compositions | |
LV12307B (en) | STANOL COMPOSITION AND USE | |
US20070218183A1 (en) | Oil composition of conjugated linoleic acid | |
AU782264B2 (en) | Edible fat blends | |
JP2005518421A (ja) | 油中のフィトステロールエステルの分別 | |
Jones et al. | Comparable efficacy of hydrogenated versus nonhydrogenated plant sterol esters on circulating cholesterol levels in humans | |
EP1370148A1 (de) | Cholesterinspiegelsenkendes speiseöl | |
US20020107232A1 (en) | Methods for producing sterol ester-rich compositions | |
JP2002322052A (ja) | 小腸上皮中の脂質代謝改善剤 | |
US20100179113A1 (en) | Stanol composition and the use thereof | |
JP2001335795A (ja) | 液状油脂組成物 | |
JP4018863B2 (ja) | 油脂組成物 | |
RU2172629C2 (ru) | Станоловая композиция и ее применение | |
MXPA00010876A (en) | Phytosterol compositions | |
IES20000995A2 (en) | A process for the manufacture of sterol esters | |
AU2001236584A1 (en) | Anticholesterolemic edible oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |