FI120148B - Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi - Google Patents

Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi Download PDF

Info

Publication number: FI120148B
Authority: FI; Finland
Prior art keywords: cholesterol; fatty acid; sitostanol; acid ester; mixture
Prior art date: 1991-05-03

Application number

FI20060782A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI20060782A (fi

Inventor

Ingmar Wester

Tatu Miettinen

Hannu Vanhanen

Original Assignee

Raisio Benecol Oy

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.)

1991-05-03

Filing date

1991-05-03

Publication date

2009-07-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8556507&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI120148(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1991-05-03 Application filed by Raisio Benecol Oy filed Critical Raisio Benecol Oy

1991-05-03 Priority to FI20060782A priority Critical patent/FI120148B/fi

2006-08-30 Publication of FI20060782A publication Critical patent/FI20060782A/fi

2009-07-15 Application granted granted Critical

2009-07-15 Publication of FI120148B publication Critical patent/FI120148B/fi

Links

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 title claims description 70
239000000203 mixture Substances 0.000 title claims description 62
-1 beta-sitostanol fatty acid ester Chemical class 0.000 title claims description 58
235000014113 dietary fatty acids Nutrition 0.000 title claims description 56
229930195729 fatty acid Natural products 0.000 title claims description 56
239000000194 fatty acid Substances 0.000 title claims description 56
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 title claims description 51
238000004519 manufacturing process Methods 0.000 title claims description 7
150000002148 esters Chemical class 0.000 title description 10
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 31
238000000034 method Methods 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 11
150000004665 fatty acids Chemical class 0.000 claims description 10
238000005886 esterification reaction Methods 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
230000032050 esterification Effects 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 5
238000005809 transesterification reaction Methods 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000002904 solvent Substances 0.000 claims 1
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 description 76
235000002378 plant sterols Nutrition 0.000 description 34
235000019484 Rapeseed oil Nutrition 0.000 description 26
235000012000 cholesterol Nutrition 0.000 description 24
239000003925 fat Substances 0.000 description 21
235000019197 fats Nutrition 0.000 description 21
NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 18
229950005143 sitosterol Drugs 0.000 description 18
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 description 17
229930182558 Sterol Natural products 0.000 description 16
238000010521 absorption reaction Methods 0.000 description 16
230000008859 change Effects 0.000 description 16
210000002966 serum Anatomy 0.000 description 16
235000003702 sterols Nutrition 0.000 description 16
150000003432 sterols Chemical class 0.000 description 14
230000001906 cholesterol absorption Effects 0.000 description 13
235000005911 diet Nutrition 0.000 description 13
235000013305 food Nutrition 0.000 description 12
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 10
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 10
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 10
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 10
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 10
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 10
230000000694 effects Effects 0.000 description 10
235000015500 sitosterol Nutrition 0.000 description 10
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 10
230000037213 diet Effects 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
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 8
238000008214 LDL Cholesterol Methods 0.000 description 8
229940076810 beta sitosterol Drugs 0.000 description 8
239000003921 oil Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
235000019198 oils Nutrition 0.000 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 description 5
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 description 5
SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical group 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 description 5
235000000431 campesterol Nutrition 0.000 description 5
235000010746 mayonnaise Nutrition 0.000 description 5
239000008268 mayonnaise Substances 0.000 description 5
239000003613 bile acid Substances 0.000 description 4
238000001723 curing Methods 0.000 description 4
230000000378 dietary effect Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
210000001035 gastrointestinal tract Anatomy 0.000 description 4
235000015112 vegetable and seed oil Nutrition 0.000 description 4
108010083590 Apoproteins Proteins 0.000 description 3
102000006410 Apoproteins Human genes 0.000 description 3
241000282414 Homo sapiens Species 0.000 description 3
210000000941 bile Anatomy 0.000 description 3
238000007664 blowing Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
208000029078 coronary artery disease Diseases 0.000 description 3
210000003608 fece Anatomy 0.000 description 3
230000001965 increasing effect Effects 0.000 description 3
235000013310 margarine Nutrition 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
229940049964 oleate Drugs 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
LGJMUZUPVCAVPU-OCTCCMJISA-N (3s,5s,8r,9s,10s,13r,14s,17r)-17-[(2r)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol 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)CCC(CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-OCTCCMJISA-N 0.000 description 2
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 description 2
108700028369 Alleles Proteins 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
208000035150 Hypercholesterolemia Diseases 0.000 description 2
108090001030 Lipoproteins Proteins 0.000 description 2
102000004895 Lipoproteins Human genes 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
235000019577 caloric intake Nutrition 0.000 description 2
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 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000013401 experimental design Methods 0.000 description 2
230000031891 intestinal absorption Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000003264 margarine Substances 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
235000014593 oils and fats Nutrition 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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 1
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
LGJMUZUPVCAVPU-ANOYILKDSA-N (3s,8r,9s,10s,13r,14s,17r)-17-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical compound C1CC2C[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 LGJMUZUPVCAVPU-ANOYILKDSA-N 0.000 description 1
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 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
KZJWDPNRJALLNS-OAIXMFQVSA-N B-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)CCC(CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-OAIXMFQVSA-N 0.000 description 1
241000219198 Brassica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
108010082495 Dietary Plant Proteins Proteins 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
241000282412 Homo Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000004165 Methyl ester of fatty acids Substances 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
206010063985 Phytosterolaemia Diseases 0.000 description 1
229920002732 Polyanhydride Polymers 0.000 description 1
208000035977 Rare disease Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000002227 Sitosterolemia Diseases 0.000 description 1
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 1
206010048215 Xanthomatosis Diseases 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003529 anticholesteremic agent Substances 0.000 description 1
229940127226 anticholesterol agent Drugs 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
235000013367 dietary fats Nutrition 0.000 description 1
235000013325 dietary fiber Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000003778 fat substitute Substances 0.000 description 1
235000013341 fat substitute Nutrition 0.000 description 1
235000019387 fatty acid methyl ester Nutrition 0.000 description 1
235000021149 fatty food Nutrition 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002778 food additive Substances 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
208000019423 liver disease Diseases 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000004213 low-fat Nutrition 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000011020 pilot scale process Methods 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
238000002271 resection Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
235000000891 standard diet Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
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 1
235000016831 stigmasterol Nutrition 0.000 description 1
229940032091 stigmasterol Drugs 0.000 description 1
BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
230000009469 supplementation Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
230000032258 transport Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
150000003722 vitamin derivatives Chemical class 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0056—Spread compositions
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
- 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
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/804—Low calorie, low sodium or hypoallergic

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Obesity (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Hematology (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Edible Oils And Fats (AREA)
Steroid Compounds (AREA)
Seasonings (AREA)

FI20060782A 1991-05-03 1991-05-03 Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi FI120148B (fi)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
FI20060782A FI120148B (fi)	1991-05-03	1991-05-03	Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
PCT/FI1991/000139 WO1992019640A1 (en)	1991-05-03	1991-05-03	A substance for lowering high cholesterol level in serum and a method for preparing the same
FI9100139		1991-05-03
FI20060782A FI120148B (fi)	1991-05-03	1991-05-03	Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi
FI20060782		2006-08-30

Publications (2)

Publication Number	Publication Date
FI20060782A FI20060782A (fi)	2006-08-30
FI120148B true FI120148B (fi)	2009-07-15

Family

ID=8556507

Family Applications (5)

Application Number	Title	Priority Date	Filing Date
FI20060782A FI120148B (fi)	1991-05-03	1991-05-03	Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi
FI934869A FI98730C (fi)	1991-05-03	1993-11-03	Menetelmä seerumin korkean kolesterolitason alentamiseen käytettävän aineen valmistamiseksi
FI964951A FI964951A (fi)	1991-05-03	1996-12-11	Seerumin korkean kolesterolitason alentamiseen käytettävä aine ja sen käyttö
FI20011891A FI117614B (fi)	1991-05-03	2001-09-26	Menetelmä beta-sitostanolirasvahappoesteriä sisältävän elintarvikkeen valmistamiseksi ja tämän esterin käyttö
FI20090166A FI121377B (fi)	1991-05-03	2009-04-27	Menetelmä seerumin beta-sitosteroli ja/tai kampesterolipitoisuutta alentavan beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi

Family Applications After (4)

Application Number	Title	Priority Date	Filing Date
FI934869A FI98730C (fi)	1991-05-03	1993-11-03	Menetelmä seerumin korkean kolesterolitason alentamiseen käytettävän aineen valmistamiseksi
FI964951A FI964951A (fi)	1991-05-03	1996-12-11	Seerumin korkean kolesterolitason alentamiseen käytettävä aine ja sen käyttö
FI20011891A FI117614B (fi)	1991-05-03	2001-09-26	Menetelmä beta-sitostanolirasvahappoesteriä sisältävän elintarvikkeen valmistamiseksi ja tämän esterin käyttö
FI20090166A FI121377B (fi)	1991-05-03	2009-04-27	Menetelmä seerumin beta-sitosteroli ja/tai kampesterolipitoisuutta alentavan beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi

Country Status (14)

Country	Link
US (6)	US5502045A (no)
EP (1)	EP0594612B2 (no)
JP (1)	JP2708633B2 (no)
AU (1)	AU664827B2 (no)
CA (1)	CA2102112C (no)
DE (1)	DE69127207T2 (no)
DK (1)	DK0594612T4 (no)
FI (5)	FI120148B (no)
HK (1)	HK1001951A1 (no)
HU (1)	HU217625B (no)
NO (1)	NO304581B1 (no)
PL (1)	PL166991B1 (no)
RU (1)	RU2095367C1 (no)
WO (1)	WO1992019640A1 (no)

Families Citing this family (217)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6544973B1 (en) *	1995-07-28	2003-04-08	Raisio Benecol Ltd.	Substance for lowering high cholesterol level in serum and methods for preparing and using the same
RU2095367C1 (ru)	1991-05-03	1997-11-10	Райсион Техтаат ой АБ	Вещество, понижающее уровень холестерина в сыворотке крови, и способ его получения
US6268392B1 (en)	1994-09-13	2001-07-31	G. D. Searle & Co.	Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors
US6642268B2 (en)	1994-09-13	2003-11-04	G.D. Searle & Co.	Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors
US6262277B1 (en)	1994-09-13	2001-07-17	G.D. Searle And Company	Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
ATE216395T1 (de) *	1994-09-29	2002-05-15	Univ British Columbia	Sterin zusammensetzungen aus holzaufschlussseife
AU2007200897B2 (en) *	1994-09-29	2010-12-23	Pharmachem Laboratories, Inc.	Sterol compositions from pulping soap
CA2222771C (en) *	1995-06-01	2002-02-26	Unilever Plc	Fat based food products
FI105274B (fi) *	1996-03-15	2000-07-14	Upm Kymmene Oy	Menetelmä ei-hormonivaikutteisten, tyydyttymättömien kasvisteroidien hydraamiseksi ja käytetyn katalyytin regenerointi
US6057339A (en) *	1996-05-09	2000-05-02	Bristol-Myers Squibb Company	Method of inhibiting or treating phytosterolemia with an MTP inhibitor
EP0918465B1 (en)	1996-05-10	2005-01-12	Unilever N.V.	Liquid fatty component containing composition
US5965449A (en) *	1996-07-03	1999-10-12	Forbes Medi-Tech, Inc.	Method of assessing risk for cardiovascular disease and other disorders and phytosterol-based compositions useful in preventing and treating cardiovascular disease and other disorders
BR9710137A (pt) *	1996-07-05	1999-08-10	Unilever Nv	Processo para a fabricação de uma mistura de éster mistura de ésteres de ácido graxo de esteróis e produto alimenticio à base de gordura
US20030104035A1 (en) *	1996-08-09	2003-06-05	Raisio Benecol Ltd.	Stanol composition and the use thereof
FI107015B (fi) *	1996-08-09	2001-05-31	Raisio Benecol Oy	Kasvistanolirasvahappoestereiden seos ja sen käyttö sekä elintarvike
FI105887B (fi) *	1996-09-27	2000-10-31	Suomen Sokeri Oy	Elintarvike- ja terapeuttisiin sovelluksiin käyttökelpoiset, kasvisterolia sisältävät tuotteet, menetelmä niiden valmistamiseksi ja niiden käyttö
US6929816B2 (en)	1998-01-21	2005-08-16	Raisio Benecol Ltd.	Fat compositions for use in food
UA69378C2 (uk)	1996-11-04	2004-09-15	Райзіо Бенекол Лтд.	Текстуруюча композиція, текстуруючий агент, харчовий продукт, жирові суміші та способи їх одержання
CZ326896A3 (cs)	1996-11-07	1998-05-13	Milo Olomouc, A. S.	Tuk se specifickými protisklerotickými účinky
NZ335974A (en)	1996-11-28	2000-06-23	Henkel Kgaa	Hypocholesteremic agents containing tocopherols and phytostanol (phytosterols)
AU714993B2 (en)	1996-11-28	2000-01-13	Cognis Deutschland Gmbh & Co. Kg	Use of mixtures of active substances, containing phytostenols and/or phytostenol esters and potentiators, for the production of hypocholesteremic preparations
FI120290B (fi) *	1996-12-30	2009-09-15	Mirador Res Oy Ltd	Menetelmä, jonka avulla voidaan valmistaa sellaisia mausteseos-, ruoan ainesosa- ja elintarvikekoostumuksia, jotka alentavat seerumin kolesterolia
AU6023298A (en) *	1997-01-17	1998-08-07	Bristol-Myers Squibb Company	A method of inhibiting or treating phytosterolemia with an mtp inhibitor
FI107538B (fi)	1997-02-26	2001-08-31	Raisio Benecol Oy	Menetelmä stanoliesterien valmistamiseksi
US5929062A (en) *	1997-06-19	1999-07-27	University Of Western Ontario	Oxysterol inhibition of dietary cholesterol uptake
ES2209056T3 (es) *	1997-08-22	2004-06-16	Unilever N.V.	Composiciones que comprenden estanol.
EP0897971B1 (en) *	1997-08-22	2004-11-03	Unilever N.V.	Stanol ester composition
EP1440619B1 (en) *	1997-08-22	2006-11-02	Unilever N.V.	Fat based food products comprising sterols
DK0897970T3 (da) *	1997-08-22	2004-11-08	Unilever Nv	Fremgangsmåde til fremstilling af stanolestere
ES2231940T3 (es) *	1997-08-22	2005-05-16	Unilever N.V.	Composicion de esteres de estanol.
DE69824501T2 (de) *	1997-08-22	2004-11-04	Unilever N.V.	Fettenthaltende Nahrungsmittelprodukte mit Sterolen
US6423363B1 (en) †	1997-08-22	2002-07-23	Lipton, Division Of Conopco, Inc.	Aqueous dispersion
FI974648A (fi) *	1997-09-09	1999-05-06	Raisio Benecol Oy	Hydroksihappo-, maitohappo- ja hydroksialkanoaattiesterit ja niiden käyttö
DE19750422C1 (de) *	1997-11-14	1998-11-26	Henkel Kgaa	Verwendung von ausgewählten Phytostenolestern zur Herstellung von hypocholesterinämischen Mitteln
US6394230B1 (en) *	1997-12-16	2002-05-28	Cognis Corporation	Sterol esters as food additives
US5952393A (en) *	1998-02-12	1999-09-14	Sorkin, Jr.; Harlan Lee	Composition for reducing serum cholesterol levels
IN185730B (no) *	1998-02-19	2001-04-14	Mcneil Ppc Inc
US6110502A (en) *	1998-02-19	2000-08-29	Mcneil-Ppc, Inc.	Method for producing water dispersible sterol formulations
FI109327B (fi)	1998-02-27	2002-07-15	Spice Sciences Oy	Menetelmä seerumin kokonais- ja LDL-kolestrolipitoisuutta alentavan beta-sitosterolin rasvamaisen seoksen valmistamiseksi
FR2775620B1 (fr) *	1998-03-05	2002-04-19	Gervais Danone Sa	Suspension homogene stable depourvue d'emulsifiant, son procede de preparation et son utilisation dans des compositions alimentaires
US6025348A (en) *	1998-04-30	2000-02-15	Kao Corporation	Oil and fat composition containing phytosterol
US6139897A (en) *	1998-03-24	2000-10-31	Kao Corporation	Oil or fat composition containing phytosterol
FI111513B (fi)	1998-05-06	2003-08-15	Raisio Benecol Oy	Uudet fytosteroli- ja fytostanolirasvahappoesterikoostumukset, niitä sisältävät tuotteet sekä menetelmät niiden valmistamiseksi
US6087353A (en) *	1998-05-15	2000-07-11	Forbes Medi-Tech Inc.	Phytosterol compositions and use thereof in foods, beverages, pharmaceuticals, nutraceuticals and the like
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
IN186960B (no) *	1998-08-25	2001-12-22	Mcneil Ppc Inc
US5892068A (en) *	1998-08-25	1999-04-06	Mcneil-Ppc, Inc.	Preparation of sterol and stanol-esters
US6123978A (en) *	1998-08-31	2000-09-26	Mcneil-Ppc, Inc.	Stable salad dressings
US6376481B2 (en)	1998-09-02	2002-04-23	Mcneil-Ppc, Inc.	Sterol esters in tableted solid dosage forms
US6277431B1 (en) *	1998-10-14	2001-08-21	Redeem, Inc.	Anticholesterolemic edible oil
NZ501169A (en) *	1998-11-26	2001-05-25	F	Fatty acid esters of phytosterol and phytostanol
US6242001B1 (en)	1998-11-30	2001-06-05	Mcneil-Ppc, Inc.	Method for producing dispersible sterol and stanol compounds
US6113972A (en) *	1998-12-03	2000-09-05	Monsanto Co.	Phytosterol protein complex
ATE242009T1 (de) *	1998-12-23	2003-06-15	Searle Llc	Kombinationen von cholesteryl ester transfer protein inhibitoren und fibronsäure derivaten für kardiovaskuläre indikationen
IL143943A0 (en)	1998-12-23	2002-04-21	Searle Llc	Combinations of ileal bile acid transport inhibitors and bile acid sequestering agents for cardiovascular indications
DK1140187T3 (da) *	1998-12-23	2003-12-22	Searle Llc	Kombinationer af en IBAT-inhibitor og en MTP-inhibitor til cardiovaskulære indikationer
HUP0104793A2 (en)	1998-12-23	2002-06-29	Searle Llc	Combinations of ileal bile acid transport inhibitors and fibric acid derivatives for cardiovascular indications
EA005815B1 (ru)	1998-12-23	2005-06-30	Джи.Ди.Сирл Ллс	Комбинация ингибиторов транспорта желчных кислот в подвздошной кишке и ингибиторов белка, переносящего эфиры холестерина, для сердечно-сосудистых показаний
US6462091B1 (en)	1998-12-23	2002-10-08	G.D. Searle & Co.	Combinations of cholesteryl ester transfer protein inhibitors and HMG coA reductase inhibitors for cardiovascular indications
PT1140185E (pt)	1998-12-23	2003-10-31	Searle Llc	Combinacoes de inibidores de proteina de transferencia de ester de colesterilo com agentes sequestrantes de acido biliar para indicacoes cardiovasculares
ATE242007T1 (de)	1998-12-23	2003-06-15	Searle Llc	Kombinationen von cholesteryl ester transfer protein inhibitoren und nicotinsäure derivaten für kardiovaskuläre indikationen
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
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
EP1169462B1 (en)	1999-04-12	2009-10-21	Monsanto Technology LLC	Oil comprising brassicastanol
KR100278194B1 (ko) *	1999-04-13	2001-01-15	노승권	콜레스테롤 저하효과를 갖는 지용성 피토스테롤 또는 피토스타놀의 불포화 지방산 에스테르 화합물의 제조방법
US6410758B2 (en)	1999-05-24	2002-06-25	Mcneil-Ppc, Inc.	Preparation of sterol and stanol-esters
US6190720B1 (en)	1999-06-15	2001-02-20	Opta Food Ingredients, Inc.	Dispersible sterol compositions
AU5405200A (en)	1999-06-25	2001-01-31	Cognis Deutschland Gmbh & Co. Kg	Use of nanoscale sterols and sterol esters
US6998501B1 (en) *	1999-08-30	2006-02-14	Ocean Nutrition Canada Limited	Nutritional supplement for lowering serum triglyceride and cholesterol levels
AU6813700A (en) *	1999-08-30	2001-03-26	Ocean Nutrition Canada Ltd.	A nutritional supplement for lowering serum triglyceride and cholesterol levels
US6197832B1 (en)	1999-09-14	2001-03-06	Harlan Lee Sorkin, Jr.	Composition for reducing serum cholesterol levels
AU2118701A (en)	1999-10-21	2001-04-30	Board Of Regents For Oklahoma State University, The	Sterol esters of conjugated linoleic acids and process for their production
SE517769C2 (sv) *	1999-10-29	2002-07-16	Triple Crown Ab	Kolesterol och blodfettsänkande komposition, innehållande fytosteroler, blandade med monoglycerider
RU2259750C2 (ru)	1999-11-05	2005-09-10	Райсио Бенекол Ой	Продукт на основе оливкового масла, способ приготовления продукта на основе оливкового масла (варианты) и смесь сложных эфиров
US6677327B1 (en)	1999-11-24	2004-01-13	Archer-Daniels-Midland Company	Phytosterol and phytostanol compositions
US7232574B1 (en)	1999-12-15	2007-06-19	Mcneil-Ppc, Inc.	Long chain alcohols provided in edible oils
US6355274B1 (en)	1999-12-15	2002-03-12	Mcneil-Ppc, Inc.	Encapsulated long chain alcohols
WO2001055098A1 (en)	2000-01-28	2001-08-02	The Procter & Gamble Company	Palatable arginine compounds and uses thereof for cardiovascular health
ATE384518T1 (de) *	2000-01-31	2008-02-15	Haerting S A	Zusammensetzungen enthaltend phytosterol- und policosanolester von fettsäuren zur herabsetzung des cholesterol- und triglyceridspiegels
US20020061888A1 (en) *	2000-03-10	2002-05-23	Keller Bradley T.	Combination therapy for the prophylaxis and treatment of hyperlipidemic conditions and disorders
AU2001240115A1 (en)	2000-03-10	2001-09-24	Pharmacia Corporation	Method for the preparation of tetrahydrobenzothiepines
US20020016317A1 (en) *	2000-03-27	2002-02-07	Schul David Allen	Sterol ester compositions
MXPA02009956A (es)	2000-04-14	2003-02-12	Mars Inc	Composiciones y metodos para mejorar la salud vascular.
FR2811984B1 (fr) *	2000-07-19	2004-02-06	Pharmascience Lab	Procede de preparation d'un ester de corps gras et son utilisation dans les domaines pharmaceutique, cosmetique ou alimentaire
US6838098B2 (en) *	2000-09-07	2005-01-04	Cadbury Adams Usa, Llc	Continuous formation of center filled gum
KR20020026053A (ko) *	2000-09-30	2002-04-06	노승권	음료용 식물성 스테롤의 분산방법 및 이를 함유하는 음료
US20020098267A1 (en) *	2000-10-23	2002-07-25	The Procter & Gamble Co.	Filled snacks
US6743458B2 (en)	2000-10-23	2004-06-01	The Procter + Gamble Co.	Reduced fat lipid-based fillings
US6720021B2 (en) *	2000-10-23	2004-04-13	The Procter + Gamble Co.	Process for making a low-fat nut spread composition
US6793956B2 (en)	2000-10-23	2004-09-21	The Procter & Gamble Co.	Low-moisture, reduced fat, lipid-based fillings
US6576285B1 (en) *	2000-11-14	2003-06-10	Sunpure Ltd.	Cholesterol lowering beverage
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 (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
US20020107232A1 (en) *	2001-01-12	2002-08-08	Flickinger Brent D.	Methods for producing sterol ester-rich compositions
US6623266B2 (en) *	2001-01-19	2003-09-23	Cadbury Adams Usa Llc	Apparatus for making a center-filled gum lollipop with hard candy shell
FI20010780A0 (fi) *	2001-04-12	2001-04-12	Raisio Benecol Oy	Parannetut koostumukset
US20030003131A1 (en) *	2001-06-22	2003-01-02	Matthew Dyer	Method for manufacture of free-flowing powder containing water-dispersible sterols
EP1275309A1 (en) *	2001-07-13	2003-01-15	Ikeda Food Research Co. Ltd.	Sterol fatty acid ester composition and foods containing the same
US20040077625A1 (en) *	2001-07-25	2004-04-22	Tremont Samuel J.	Novel 1,4-benzothiazepine and 1,5-benzothiazepine compounds as inhibitors of apical sodium codependent bile acid transport abd taurocholate uptake
US6787151B2 (en) *	2001-08-10	2004-09-07	Lipton, Division Of Conopco, Inc.	Composition for lowering blood cholesterol
WO2003022064A1 (en) *	2001-09-07	2003-03-20	Cargill Incorporated	Steryl ester compositions
WO2003040127A1 (en) *	2001-11-02	2003-05-15	G.D. Searle Llc	Novel mono- and di-fluorinated benzothiepine compounds as inhibitors of apical sodium co-dependent bile acid transport (asbt) and taurocholate uptake
AU2002352747A1 (en) *	2001-11-16	2003-06-10	Brandeis University	Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
US7144595B2 (en) *	2001-11-16	2006-12-05	Brandeis University	Prepared foods containing triglyceride-recrystallized non-esterified phytosterols
EP1454532B1 (en)	2001-12-07	2011-02-09	Ajinomoto Co., Inc.	Oil-in-water type emulsion containing vegetable sterols
US7763663B2 (en) *	2001-12-19	2010-07-27	University Of Massachusetts	Polysaccharide-containing block copolymer particles and uses thereof
US7244455B2 (en) *	2002-01-16	2007-07-17	Warner-Lambert Company	Center-filled chewing gum containing a deliverable form of calcium
WO2003061604A2 (en)	2002-01-17	2003-07-31	Pharmacia Corporation	Novel alkyl/aryl hydroxy or keto thiepines.
US6835558B2 (en) *	2002-02-04	2004-12-28	General Mills, Inc.	Beta-glucan compositions and process therefore
WO2003077679A1 (en) *	2002-03-20	2003-09-25	Eugene Science Inc.	Plant sterol-containing food, and method for preparing the same
US7514107B2 (en)	2002-03-21	2009-04-07	Mars, Incorporated	Treatment of diseases involving defective gap junctional communication
US20040014733A1 (en) *	2002-04-10	2004-01-22	Binder Thomas P.	Hydrothermically processed compositions containing phytosterols
US20030203854A1 (en) *	2002-04-23	2003-10-30	Ivo Pischel	Composition for effecting serum cholesterol levels
US20030232068A1 (en) *	2002-06-14	2003-12-18	Lewandowski Daniel J.	Food product having increased bile acid binding capacity
US7732000B2 (en) *	2002-06-20	2010-06-08	General Mills, Inc.	Food intermediate having sequestered phytosteryl esters in a polysaccharide matrix
US20030045473A1 (en) *	2002-07-19	2003-03-06	Sarama Robert Joseph	Compositions, kits, and methods for cardiovascular health
FI20021822A0 (fi) *	2002-10-14	2002-10-14	Raisio Benecol Oy	Elintarvike
MXPA05004461A (es) *	2002-10-31	2005-07-26	Unilever Nv	Emulsion de agua en aceite que comprende esteres de esterol.
US20040215003A1 (en) *	2002-11-12	2004-10-28	Dobbins Thomas A.	Method for purifying and separating soy isoflavones
US20040116382A1 (en) *	2002-12-13	2004-06-17	Plank David W.	Food products containing cyclodextrins having beneficial hypocholesterolemic effects and method of making and communicating the benefit of such products
EP2290085B1 (en)	2003-01-17	2017-12-13	DuPont Nutrition Biosciences ApS	Method for the in situ production of an emulsifier in a foodstuff
DE10312000A1 (de) *	2003-03-19	2004-09-30	Cognis Deutschland Gmbh & Co. Kg	Ethercarbonsäureester von Sterolen bzw. Stanolen
FI20030540A0 (fi) *	2003-04-10	2003-04-10	Raisio Benecol Oy	Hydrolyysimenetelmä
CA2531312A1 (en) *	2003-07-29	2005-02-17	Unilever Plc	Food product comprising phytosterols
US20050032757A1 (en) *	2003-08-06	2005-02-10	Cho Suk H.	Nutritional supplements
EP1660516A1 (en) *	2003-09-05	2006-05-31	University of Nebraska-Lincoln	Compound and method for enhancing the cholesterol lowering property of plant sterol and stanol esters
GB0326492D0 (en) *	2003-11-14	2003-12-17	Cadbury Schweppes Plc	Liquid-filled confectionery compositions
WO2005051290A2 (en) *	2003-11-20	2005-06-09	Zomanex, Llc	Methods and formulations for the treatment of medical conditions related to elevated dihydrotestosterone
DK2119771T3 (en)	2003-12-24	2018-12-10	Dupont Nutrition Biosci Aps	PROTEINS
US20060182820A1 (en) *	2004-02-10	2006-08-17	Cargill, Incorporated	Homogeneous Dispersions Containing Citrus Pulp and Applications Thereof
US20050175672A1 (en) *	2004-02-10	2005-08-11	Kluetz Michael D.	Particulate plant sterol compositions
US8158184B2 (en) *	2004-03-08	2012-04-17	Bunge Oils, Inc.	Structured lipid containing compositions and methods with health and nutrition promoting characteristics
US20060008564A1 (en) *	2004-07-08	2006-01-12	Pzena Wendy M	Cholesterol-lowering batter-based food composition and method for making same
PL1776455T3 (pl)	2004-07-16	2015-09-30	Dupont Nutrition Biosci Aps	Enzym lipolityczny, jego zastosowania w przemyśle spożywczym
US20060035009A1 (en)	2004-08-10	2006-02-16	Kraft Foods Holdings, Inc.	Compositions and processes for water-dispersible phytosterols and phytostanols
US20060263476A1 (en) *	2004-08-25	2006-11-23	Cadbury Adams Usa, Llc.	Center-filled chewing gum with barrier layer
US20070148286A1 (en) *	2004-08-25	2007-06-28	Cadbury Adams Usa Llc.	Liquid-filled chewing gum composition
CA2578258C (en) *	2004-08-25	2012-11-13	Cadbury Adams Usa Llc	Liquid-filled chewing gum composition
US7727565B2 (en) *	2004-08-25	2010-06-01	Cadbury Adams Usa Llc	Liquid-filled chewing gum composition
US20060286201A1 (en) *	2004-08-25	2006-12-21	Cadbury Adams Usa Llc.	Multi-modality functional ingredients in chewing gum compositions
US20070148284A1 (en) *	2004-08-25	2007-06-28	Cadbury Adams Usa Llc.	Liquid-filled chewing gum
US20080014302A1 (en) *	2004-08-25	2008-01-17	Cadbury Adams Usa Llc	Multi-region chewing gum composition including isomalt gum region
US20060280834A1 (en) *	2004-08-25	2006-12-14	Cadbury Adams Usa, Llc.	Center-filled chewing gum composition
US20060280835A1 (en) *	2004-08-25	2006-12-14	Cadbury Adams Usa Llc.	Multi-modality flavored chewing gum compositions
US20060280837A1 (en) *	2004-08-25	2006-12-14	Cadbury Adams Usa Llc.	Multi-modality sensations in chewing gum compositions
US7641926B2 (en) *	2004-08-25	2010-01-05	Cadbury Adams Usa, Llc	Liquid-filled chewing gum composition
US20060263475A1 (en) *	2004-08-25	2006-11-23	Cadbury Adams Usa, Llc.	Center-filled chewing gum composition
US20060280836A1 (en) *	2004-08-25	2006-12-14	Cadbury Adams Usa Llc.	Multi-modality tastes in chewing gum compositions
EP1642507A1 (en)	2004-10-04	2006-04-05	Unilever N.V.	Fermented meat products containing interesterified vegetable fat and dairy protein
US20060153949A1 (en) *	2005-01-11	2006-07-13	Cadbury Adams Usa Llc.	Edible compositions containing swellable polymers
DE102005008445A1 (de)	2005-02-24	2006-08-31	Cognis Ip Management Gmbh	Zuckerhaltige Sterolfeststoffdispersionen
EP2194140A2 (en) *	2005-03-02	2010-06-09	Metanomics GmbH	Process for the production of fine chemicals
EP2286677A1 (en)	2005-05-25	2011-02-23	Health Concern B.V.	Cholesterol lowering fat based food products
US7781493B2 (en)	2005-06-20	2010-08-24	Dow Global Technologies Inc.	Protective coating for window glass
US7786183B2 (en) *	2005-06-20	2010-08-31	Dow Global Technologies Inc.	Coated glass articles
US20080274195A1 (en) *	2005-07-18	2008-11-06	University Of Massachusetts Lowell	Compositions and Methods for Making and Using Nanoemulsions
US20070026126A1 (en) *	2005-08-01	2007-02-01	Bryan Hitchcock	Sterol fortified beverages
US20070031571A1 (en) *	2005-08-03	2007-02-08	Peter Cremer North America, Lp	Phytosterol esters
DE102005039836A1 (de) *	2005-08-23	2007-03-01	Cognis Ip Management Gmbh	Sterolesterpulver
DE102005039835A1 (de) *	2005-08-23	2007-03-01	Cognis Ip Management Gmbh	Pulverförmige Sterolformulierungen mit Kolloidbildnern
US7575768B2 (en) *	2005-09-07	2009-08-18	Brandeis University	Dietary supplements and prepared foods containing triglyceride-recrystallized non-esterified phytosterols
WO2007039040A1 (en) *	2005-09-30	2007-04-12	Unilever N.V.	Food composition
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
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
JP5191391B2 (ja) *	2005-11-01	2013-05-08	ターゲジェンインコーポレーティッド	キナーゼのビ−アリールメタ−ピリミジン阻害剤
US7601380B2 (en) *	2005-11-17	2009-10-13	Pepsico, Inc.	Beverage clouding system and method
ES2281270B1 (es)	2005-11-30	2008-07-01	La Morella Nuts, S.A.	Alimento funcional con efectos positivos en la prevencion de enfermedades cardiovasculares.
KR20080071615A (ko)	2005-12-01	2008-08-04	유니버시티 오브 메사츄세츠 로웰	보툴리눔 나노에멀젼
US9486408B2 (en)	2005-12-01	2016-11-08	University Of Massachusetts Lowell	Botulinum nanoemulsions
WO2007071036A1 (en) *	2005-12-20	2007-06-28	Forbes Medi-Tech Inc.	Emulsions comprising non-esterified phytosterols in the aqueous phase
US20070148311A1 (en) *	2005-12-22	2007-06-28	Bunge Oils, Inc.	Phytosterol esterification product and method of make same
AU2007222697B2 (en) *	2006-03-08	2012-07-05	Cognis Ip Management Gmbh	Powder containing sterol
DE102006010663A1 (de) *	2006-03-08	2007-09-13	Cognis Ip Management Gmbh	Verfahren zur Herstellung sterolhaltiger Pulver
DE102006041302A1 (de) *	2006-03-08	2007-09-13	Cognis Ip Management Gmbh	Sterolester mit kurzkettigen Fettsäuren
BRPI0710292A2 (pt)	2006-04-05	2011-08-09	Cadbury Adams Usa Llc	complexo de fosfato de cálcio em uma goma de mascar contendo ácido
US8133476B2 (en)	2006-04-05	2012-03-13	Cadbury Adams Usa Llc	Calcium phosphate complex and salts in oral delivery systems
MX2008012520A (es) *	2006-04-05	2008-10-10	Cadbury Adams Usa Llc	Impacto del complejo del fosfato de calcio en la caries dental.
US20070254088A1 (en) *	2006-05-01	2007-11-01	Forbes Medi-Tech Inc.	Composition comprising one or more esterified phytosterols and/or phytostanols into which are solubilized one or more unesterified phytosterols and/or phytostanols, in order to achieve therapeutic and formulation benefits
WO2007124598A2 (en) *	2006-05-01	2007-11-08	Forbes Medi-Tech Inc.	Softgel capsules with phytosterols and/or phytostanols and optionlly omega polyunstaurated fatty acids
EP1859690A1 (en)	2006-05-26	2007-11-28	Health Concern B.V.	Premix for cholesterol lowering food products
AU2007264968B2 (en) *	2006-06-29	2011-05-26	Intercontinental Great Brands Llc	Improved chain cutter for continuously forming center-filled gum pieces
US20080015374A1 (en) *	2006-07-11	2008-01-17	Wiley Organics, Inc.	Method for the synthesis and isolation of phytosterol esters
US20080063748A1 (en) *	2006-09-08	2008-03-13	Cadbury Adams Usa Llc.	Center-fill confectionery and chewing gum compositions containing suspended saccharide particles
CA2671133C (en) *	2006-12-01	2015-11-24	Anterios, Inc.	Peptide nanoparticles and uses therefor
MX2009005727A (es)	2006-12-01	2009-08-27	Anterios Inc	Nanoparticulas de entidad anfifilica.
CN101558456B (zh)	2006-12-19	2013-07-24	陶氏环球技术公司	经改善的用于导电透明基材的复合材料和方法
EP1992235A1 (en)	2007-05-09	2008-11-19	Health Concern B.V.	Premix for cholesterol lowering food products
US10016451B2 (en)	2007-05-31	2018-07-10	Anterios, Inc.	Nucleic acid nanoparticles and uses therefor
WO2009018158A1 (en) *	2007-07-27	2009-02-05	Cadbury Adams Usa Llc	Method and apparatus for processing confectionery products
US7790495B2 (en) *	2007-10-26	2010-09-07	International Business Machines Corporation	Optoelectronic device with germanium photodetector
WO2009079647A1 (en)	2007-12-18	2009-06-25	Dow Global Technologies Inc.	Protective coating for window glass having enhanced adhesion to glass bonding adhesives
CA2726836C (en) *	2008-06-26	2019-06-18	Anterios, Inc.	Use of nanoemulsions in the manufacture of a medicament for treating skin disorders
FI20090023A0 (fi)	2009-01-26	2009-01-26	Ravintoraisio Oy	Uusi elintarvike
BRPI1012562B1 (pt)	2009-03-31	2020-10-27	Dupont Nutrition Biosciences Aps	método para reduzir a cor e/ou sabor desagradável e/ou desenvolvimento de mau cheiro em um farelo de cereal solubilizado
US20110038848A1 (en)	2009-08-12	2011-02-17	Melaleuca, Inc.	Dietary supplement compositions for cardiovascular health
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
US9603858B2 (en)	2010-11-29	2017-03-28	Raisio Nutrition Ltd.	Compositions for preventing and treating an immune system disorder
FI123374B (fi)	2011-03-25	2013-03-15	Ravintoraisio Oy	Uusi syötävä koostumus
GR1007730B (el)	2011-10-04	2012-10-19	ΜΙΝΕΡΒΑ ΑΝΩΝΥΜΟΣ ΕΤΑΙΡΕΙΑ ΕΛΑΙΟΥΡΓΙΚΩΝ ΕΠΙΧΕΙΡΗΣΕΩΝ και δ.τ. "MINERVA SA EDIBLE OILS ENTERPRISES",	Μαλακο λευκο τυρι αλμης χαμηλων λιπαρων εμπλουτισμενο με εναν παραγοντα που συμβαλλει στη μειωση της χοληστερολης και μεθοδος παραγωγης αυτου
WO2013081462A1 (en)	2011-12-02	2013-06-06	Universiteit Maastricht	Phytostanols for the prevention or treatment of hepatic inflammation
CN102584931B (zh) *	2012-01-12	2014-07-02	西安蓝天生物工程有限责任公司	以α-亚麻酸为主的不饱和脂肪酸植物甾醇酯的制备方法
CN102603845B (zh) *	2012-01-21	2014-10-22	西安海斯夫生物科技有限公司	合成与分离植物甾醇饱和脂肪酸酯和不饱和脂肪酸酯的方法
WO2013171100A1 (en)	2012-05-16	2013-11-21	Joachim Hans	Polyhydroxylated pentacyclic triterpene acids as hmg-coa reductase inhibitors
FI126342B (en)	2012-09-24	2016-10-14	Ravintoraisio Oy	Snack with LDL cholesterol lowering effect
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
FI125947B (en)	2013-07-05	2016-04-29	Ravintoraisio Oy	Serum cholesterol-lowering composition
EP3113629A1 (en)	2014-03-03	2017-01-11	Raisio Nutrition Ltd	Serum cholesterol lowering edible product
KR20170070065A (ko)	2014-10-17	2017-06-21	라이시오 뉴트리션 리미티드	콜레스테롤 저하 캡슐
US10137164B2 (en)	2015-01-02	2018-11-27	Melaleuca, Inc.	Dietary supplement compositions
TWI790189B (zh)	2015-01-02	2023-01-21	美商梅拉洛伊卡公司	細菌組成物
TWI788111B (zh)	2015-01-02	2022-12-21	美商梅拉洛伊卡公司	多元補充品組成物
PL3242560T3 (pl)	2015-01-07	2022-09-12	Raisio Nutrition Ltd	Mieszanki tłuszczowe i zawierające je produkty do smarowania
CN105001083B (zh) *	2015-07-31	2017-05-03	宜春大海龟生命科学有限公司	植物甾醇油酸酯的制备方法
WO2017063660A1 (en)	2015-10-16	2017-04-20	Raisio Nutrition Ltd	Capsules for lowering cholesterol
EP3287014B1 (de)	2016-08-22	2020-02-26	Verbio Vereinigte Bioenergie AG	Verfahren zur herstellung einer phytosterol-phytostanolzusammensetzung
EP3541358A1 (en)	2016-11-21	2019-09-25	Eirion Therapeutics, Inc.	Transdermal delivery of large agents

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA567202A (en)		1958-12-09	M. R. Beveridge James	Food compositions having hypocholesterolemic activity
US1413102A (en)	1921-01-04	1922-04-18	Jean B Daudelin	Hand-threading loom shuttle
US2422317A (en) *	1944-10-04	1947-06-17	American Cyanamid Co	Means for impact testing
US3004043A (en) *	1959-10-09	1961-10-10	Eastman Kodak Co	Water-soluble vegetable oil sterol derivatives
US3254978A (en) *	1965-03-10	1966-06-07	Pittsburgh Plate Glass Co	Method and apparatus for forming fibers
JPS444974Y1 (no)	1965-06-28	1969-02-24
JPS444974B1 (no) *	1965-08-01	1969-02-28
US3600188A (en)	1967-07-18	1971-08-17	Swift & Co	Animal feed manufacture
US3600186A (en) *	1968-04-23	1971-08-17	Procter & Gamble	Low calorie fat-containing food compositions
CA928140A (en) *	1969-07-17	1973-06-12	A. Erickson Billy	Clear cooking and salad oils having hypocholesterolemic properties
US3852311A (en)	1970-05-11	1974-12-03	H Nicholas	Ergosteryl esters having liquid crystalline properties
US3751569A (en) *	1972-01-12	1973-08-07	Procter & Gamble	Clear cooking and salad oils having hypocholesterolemic properties
DE2248921C3 (de) *	1972-10-05	1981-11-12	Harburger Oelwerke Brinckman & Mergell, 2100 Hamburg	Verfahren zur Herstellung eines Gemisches aus pflanzlichen und tierischen Ölen bzw. Fetten und Fettsäuresterinestern
ES414508A1 (es) *	1973-05-08	1976-02-01	Ferrer Labor	Procedimiento de fabricacion de un compuesto de accion hi- polipemiante.
US3954976A (en) *	1973-12-14	1976-05-04	The Procter & Gamble Company	Pharmaceutical compositions for inhibiting absorption of cholesterol
US4034063A (en) *	1974-03-22	1977-07-05	Industrial Resources, Inc.	Process for control of SOx emissions from copper smelter operations
US4160850A (en)	1975-08-25	1979-07-10	General Mills, Inc.	Shelf-stable mix for a spreadable butter-substitute
US4034083A (en)	1975-11-03	1977-07-05	The Procter & Gamble Company	Compositions for inhibiting absorption of cholesterol
US4005196A (en) *	1976-02-12	1977-01-25	The Procter & Gamble Company	Vitaminized compositions for treating hypercholesterolemia
US4897224A (en)	1985-03-05	1990-01-30	Morinaga Milk Industry Co., Ltd.	Method for producing ferulyl stanol derivatives
EP0195311B2 (en) *	1985-03-06	1996-01-17	Yoshikawa Oil & Fat Co., Ltd.	Process for preparing fatty acid esters
JPS62186936A (ja) *	1986-02-13	1987-08-15	Asahi Denka Kogyo Kk	ステリン乳化乃至可溶化組成物
WO1991001139A1 (de) *	1989-07-21	1991-02-07	Marigen S.A.	Sterole, deren fettsäureester und glucoside; verfahren zu ihrer herstellung; spontan dispergierbare mittel mit diesen verbindungen, sowie ihre verwendung zur behandlung von tumoren
RU2095367C1 (ru)	1991-05-03	1997-11-10	Райсион Техтаат ой АБ	Вещество, понижающее уровень холестерина в сыворотке крови, и способ его получения
US5244887A (en) *	1992-02-14	1993-09-14	Straub Carl D	Stanols to reduce cholesterol absorption from foods and methods of preparation and use thereof
CA2222771C (en)	1995-06-01	2002-02-26	Unilever Plc	Fat based food products
EP0918465B1 (en)	1996-05-10	2005-01-12	Unilever N.V.	Liquid fatty component containing composition
FI107015B (fi)	1996-08-09	2001-05-31	Raisio Benecol Oy	Kasvistanolirasvahappoestereiden seos ja sen käyttö sekä elintarvike
AU714993B2 (en) *	1996-11-28	2000-01-13	Cognis Deutschland Gmbh & Co. Kg	Use of mixtures of active substances, containing phytostenols and/or phytostenol esters and potentiators, for the production of hypocholesteremic preparations
DE69824501T2 (de)	1997-08-22	2004-11-04	Unilever N.V.	Fettenthaltende Nahrungsmittelprodukte mit Sterolen
ES2209056T3 (es)	1997-08-22	2004-06-16	Unilever N.V.	Composiciones que comprenden estanol.

1991
- 1991-05-03 RU RU9193058424A patent/RU2095367C1/ru active
- 1991-05-03 EP EP91908435A patent/EP0594612B2/en not_active Expired - Lifetime
- 1991-05-03 DK DK91908435.0T patent/DK0594612T4/da active
- 1991-05-03 AU AU77505/91A patent/AU664827B2/en not_active Expired
- 1991-05-03 PL PL91301114A patent/PL166991B1/pl unknown
- 1991-05-03 FI FI20060782A patent/FI120148B/fi active IP Right Grant
- 1991-05-03 US US08/140,085 patent/US5502045A/en not_active Expired - Lifetime
- 1991-05-03 JP JP3506770A patent/JP2708633B2/ja not_active Expired - Lifetime
- 1991-05-03 HU HU9303111A patent/HU217625B/hu unknown
- 1991-05-03 DE DE69127207T patent/DE69127207T2/de not_active Expired - Lifetime
- 1991-05-03 WO PCT/FI1991/000139 patent/WO1992019640A1/en active Application Filing
- 1991-05-03 CA CA2102112A patent/CA2102112C/en not_active Expired - Lifetime
1993
- 1993-11-02 NO NO933966A patent/NO304581B1/no not_active IP Right Cessation
- 1993-11-03 FI FI934869A patent/FI98730C/fi active
1996
- 1996-11-05 US US08/744,009 patent/US5958913A/en not_active Expired - Fee Related
- 1996-12-11 FI FI964951A patent/FI964951A/fi unknown
1998
- 1998-01-06 HK HK98100100A patent/HK1001951A1/xx not_active IP Right Cessation
- 1998-11-12 US US09/190,598 patent/US6174560B1/en not_active Expired - Fee Related
2001
- 2001-09-26 FI FI20011891A patent/FI117614B/fi active IP Right Grant
2002
- 2002-11-07 US US10/289,341 patent/US6770768B2/en not_active Expired - Fee Related
2003
- 2003-10-06 US US10/678,135 patent/US7002030B2/en not_active Expired - Fee Related
2005
- 2005-08-11 US US11/201,313 patent/US7691834B2/en not_active Expired - Fee Related
2009
- 2009-04-27 FI FI20090166A patent/FI121377B/fi active IP Right Grant

Also Published As

Publication number	Publication date
FI121377B (fi)	2010-10-29
FI964951A0 (fi)	1996-12-11
US5502045A (en)	1996-03-26
US5958913A (en)	1999-09-28
FI934869A (fi)	1993-11-03
US6770768B2 (en)	2004-08-03
EP0594612B2 (en)	2010-02-24
AU664827B2 (en)	1995-12-07
HU217625B (hu)	2000-03-28
NO933966D0 (no)	1993-11-02
FI20011891A (fi)	2001-09-26
US20040067921A1 (en)	2004-04-08
DK0594612T3 (da)	1997-09-01
HUT65318A (en)	1994-05-02
RU2095367C1 (ru)	1997-11-10
CA2102112C (en)	2010-04-13
AU7750591A (en)	1992-12-21
FI117614B (fi)	2006-12-29
EP0594612B1 (en)	1997-08-06
US6174560B1 (en)	2001-01-16
CA2102112A1 (en)	1992-11-04
FI98730B (fi)	1997-04-30
US7002030B2 (en)	2006-02-21
DK0594612T4 (da)	2010-06-07
DE69127207D1 (de)	1997-09-11
FI20090166A (fi)	2009-04-27
EP0594612A1 (en)	1994-05-04
JP2708633B2 (ja)	1998-02-04
US20030134833A1 (en)	2003-07-17
HK1001951A1 (en)	1998-07-24
FI964951A (fi)	1996-12-11
WO1992019640A1 (en)	1992-11-12
FI20060782A (fi)	2006-08-30
HU9303111D0 (en)	1994-01-28
FI934869A0 (fi)	1993-11-03
US7691834B2 (en)	2010-04-06
NO933966L (no)	1993-11-02
DE69127207T2 (de)	1998-01-22
PL166991B1 (pl)	1995-07-31
FI98730C (fi)	1997-08-11
JPH06506909A (ja)	1994-08-04
US20050272711A1 (en)	2005-12-08
NO304581B1 (no)	1999-01-18

Publication	Publication Date	Title
FI120148B (fi)	2009-07-15	Menetelmä beta-sitostanolirasvahappoesterin tai esteriseoksen valmistamiseksi
KR100678831B1 (ko)	2007-02-05	피토스테롤 및/또는 피토스타놀 유도체
FI111513B (fi)	2003-08-15	Uudet fytosteroli- ja fytostanolirasvahappoesterikoostumukset, niitä sisältävät tuotteet sekä menetelmät niiden valmistamiseksi
US5998396A (en)	1999-12-07	Oil solubilized solutions and foods containing phytosterols and process for their production
DE69909413T2 (de)	2004-06-09	Zusammensetzung zur senkung des cholesterinspiegels
AU6823096A (en)	1998-03-06	Stanol composition and the use thereof
CZ158699A3 (cs)	1999-09-15	Texturizační kompozice pro použití v tukových směsích v potravinách
JP2005518421A (ja)	2005-06-23	油中のフィトステロールエステルの分別
US6544973B1 (en)	2003-04-08	Substance for lowering high cholesterol level in serum and methods for preparing and using the same
JP4018863B2 (ja)	2007-12-05	油脂組成物
JP2000300191A (ja)	2000-10-31	植物ステロール含有組成物

Legal Events

Date	Code	Title	Description
2009-07-15	FG	Patent granted	Ref document number: 120148 Country of ref document: FI

Date

Code

Title

Description