NO322767B1 - Fremgangsmate for fremstilling av sterol- og stanolestrer - Google Patents
Fremgangsmate for fremstilling av sterol- og stanolestrer Download PDFInfo
- Publication number
- NO322767B1 NO322767B1 NO20002635A NO20002635A NO322767B1 NO 322767 B1 NO322767 B1 NO 322767B1 NO 20002635 A NO20002635 A NO 20002635A NO 20002635 A NO20002635 A NO 20002635A NO 322767 B1 NO322767 B1 NO 322767B1
- Authority
- NO
- Norway
- Prior art keywords
- stanol
- sterol
- fatty acid
- acid
- reaction
- Prior art date
Links
- 229930182558 Sterol Natural products 0.000 title claims description 50
- 235000003702 sterols Nutrition 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 45
- 150000003432 sterols Chemical class 0.000 title claims description 34
- 150000002148 esters Chemical class 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 39
- 239000000194 fatty acid Substances 0.000 claims description 39
- 229930195729 fatty acid Natural products 0.000 claims description 39
- 150000004665 fatty acids Chemical class 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 238000011010 flushing procedure Methods 0.000 claims description 4
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-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)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims description 3
- 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 3
- MQYXUWHLBZFQQO-CWFQSGEHSA-N Lupenol Natural products C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@H](C(=C)C)[C@H]5[C@H]4CC[C@@H]3[C@]21C MQYXUWHLBZFQQO-CWFQSGEHSA-N 0.000 claims description 3
- FSLPMRQHCOLESF-SFMCKYFRSA-N alpha-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C FSLPMRQHCOLESF-SFMCKYFRSA-N 0.000 claims description 3
- SJMCNAVDHDBMLL-UHFFFAOYSA-N alpha-amyrin Natural products CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(O)CC5CCC34C)C2C1C SJMCNAVDHDBMLL-UHFFFAOYSA-N 0.000 claims description 3
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- MQYXUWHLBZFQQO-QGTGJCAVSA-N lupeol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C MQYXUWHLBZFQQO-QGTGJCAVSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 27
- -1 fatty acid ester Chemical class 0.000 description 21
- 239000000203 mixture Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 235000013305 food Nutrition 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000032050 esterification Effects 0.000 description 7
- 230000008018 melting Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000008157 edible vegetable oil Substances 0.000 description 4
- 238000009884 interesterification Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- JBYXPOFIGCOSSB-XBLVEGMJSA-N 9E,11E-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C\CCCCCCCC(O)=O JBYXPOFIGCOSSB-XBLVEGMJSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- LGJMUZUPVCAVPU-JFBKYFIKSA-N Sitostanol Natural products O[C@@H]1C[C@H]2[C@@](C)([C@@H]3[C@@H]([C@H]4[C@@](C)([C@@H]([C@@H](CC[C@H](C(C)C)CC)C)CC4)CC3)CC2)CC1 LGJMUZUPVCAVPU-JFBKYFIKSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 2
- 235000019519 canola oil Nutrition 0.000 description 2
- 239000000828 canola oil Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 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 2
- 235000005911 diet Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 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 2
- 239000007858 starting material Substances 0.000 description 2
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GKJZMAHZJGSBKD-UHFFFAOYSA-N (10E,12E)-Octadeca-9,11-dienoic acid Natural products CCCCCC=CC=CCCCCCCCCC(O)=O GKJZMAHZJGSBKD-UHFFFAOYSA-N 0.000 description 1
- GKJZMAHZJGSBKD-BLHCBFLLSA-N (10e,12e)-octadeca-10,12-dienoic acid Chemical compound CCCCC\C=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-BLHCBFLLSA-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
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- GKJZMAHZJGSBKD-ANYPYVPJSA-N 10-trans-12-cis-linoleic acid Natural products CCCCCC=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-ANYPYVPJSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 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 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 229940108924 conjugated linoleic acid Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000033227 intestinal cholesterol absorption Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/317,712 US6410758B2 (en) | 1999-05-24 | 1999-05-24 | Preparation of sterol and stanol-esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20002635D0 NO20002635D0 (no) | 2000-05-23 |
| NO20002635L NO20002635L (no) | 2000-11-27 |
| NO322767B1 true NO322767B1 (no) | 2006-12-04 |
Family
ID=23234940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20002635A NO322767B1 (no) | 1999-05-24 | 2000-05-23 | Fremgangsmate for fremstilling av sterol- og stanolestrer |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6410758B2 (fr) |
| EP (1) | EP1067135B1 (fr) |
| JP (1) | JP2001002697A (fr) |
| AR (1) | AR029636A1 (fr) |
| AT (1) | ATE334138T1 (fr) |
| AU (1) | AU779024B2 (fr) |
| BR (1) | BR0001899A (fr) |
| CA (1) | CA2309224C (fr) |
| CY (1) | CY1105242T1 (fr) |
| DE (1) | DE60029518T2 (fr) |
| DK (1) | DK1067135T3 (fr) |
| ES (1) | ES2267462T3 (fr) |
| MX (1) | MXPA00005063A (fr) |
| NO (1) | NO322767B1 (fr) |
| NZ (1) | NZ504693A (fr) |
| PT (1) | PT1067135E (fr) |
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| US6410758B2 (en) * | 1999-05-24 | 2002-06-25 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
| US6413571B1 (en) * | 1999-10-21 | 2002-07-02 | The Board Of Regents For Oklahoma State University | Sterol esters of conjugated linoleic acids and process for their production |
| KR20020026053A (ko) | 2000-09-30 | 2002-04-06 | 노승권 | 음료용 식물성 스테롤의 분산방법 및 이를 함유하는 음료 |
| WO2003077680A1 (fr) * | 2002-03-20 | 2003-09-25 | Eugene Science Inc. | Melange poudreux de sterol vegetal et d'emulsifiant, et procede de preparation associe |
| AU2002241368B2 (en) * | 2002-03-20 | 2009-07-09 | Eugene Science Inc. | Plant sterol-containing food, and method for preparing the same |
| AU2003291446A1 (en) * | 2002-11-12 | 2004-06-03 | Wiley Organics, Inc. | Method for purifying and separating soy isoflavones |
| US20070031571A1 (en) * | 2005-08-03 | 2007-02-08 | Peter Cremer North America, Lp | Phytosterol esters |
| US8524303B2 (en) | 2005-11-23 | 2013-09-03 | The Coca-Cola Company | High-potency sweetener composition with phytosterol and compositions sweetened therewith |
| US20070148311A1 (en) * | 2005-12-22 | 2007-06-28 | Bunge Oils, Inc. | Phytosterol esterification product and method of make same |
| US20080015374A1 (en) * | 2006-07-11 | 2008-01-17 | Wiley Organics, Inc. | Method for the synthesis and isolation of phytosterol esters |
| CN101544677B (zh) * | 2009-04-24 | 2011-12-14 | 武汉科技大学 | 一种植物甾醇脂肪酸酯及其制备方法 |
| ES2971273T3 (es) | 2011-12-19 | 2024-06-04 | Coca Cola Co | Bebida que comprende rebaudiósido X |
| EP2934181B1 (fr) | 2012-12-19 | 2019-09-25 | The Coca-Cola Company | Compositions et procédés permettant d'améliorer la solubilité d'un rébaudioside x |
| CN103113445B (zh) * | 2013-02-27 | 2015-06-24 | 哈尔滨工业大学 | 一种无催化剂和溶剂条件下大豆甾醇酯的高效合成法 |
| US20140272068A1 (en) | 2013-03-14 | 2014-09-18 | Indra Prakash | Beverages containing rare sugars |
| CN108329365B (zh) | 2013-03-15 | 2022-04-05 | 可口可乐公司 | 甜菊醇糖苷、其组合物以及其纯化 |
| US20160029677A1 (en) | 2013-03-15 | 2016-02-04 | The Coca-Cola Company | Novel glucosyl steviol glycosides, their compositions and their purification |
| US10905146B2 (en) | 2013-07-12 | 2021-02-02 | The Coca-Cola Company | Compositions for improving rebaudioside M solubility |
| CN104177467B (zh) * | 2014-08-07 | 2016-09-07 | 杭州余杭博士达油脂有限公司 | 一种植物甾醇酯的高效合成及分离方法 |
| CN114052237A (zh) | 2014-08-19 | 2022-02-18 | 谱赛科有限责任公司 | 制备莱鲍迪苷i的方法以及用途 |
| CN114794349A (zh) | 2014-09-02 | 2022-07-29 | 谱赛科有限责任公司 | 甜菊提取物 |
| US11584769B2 (en) | 2014-11-29 | 2023-02-21 | The Coca-Cola Company | Diterpene glycosides, compositions and purification methods |
| CN105884849A (zh) * | 2014-12-01 | 2016-08-24 | 天津工业大学 | 一种植物甾醇酯制备与纯化方法 |
| WO2016187559A1 (fr) | 2015-05-20 | 2016-11-24 | Cargill, Incorporated | Compositions de glycoside |
| RU2727426C2 (ru) | 2015-08-27 | 2020-07-21 | Пьюрсёркл Сдн Бхд | Экстракты стевии |
| WO2017059414A1 (fr) | 2015-10-02 | 2017-04-06 | The Coca-Cola Company | Édulcorants au glycoside de stéviol avec profils de saveur améliorés |
| US20190116835A1 (en) | 2016-03-28 | 2019-04-25 | The Coca-Cola Company | Sweetness and Taste Improvement of Steviol Glycoside or Mogroside Sweeteners with Flavonids |
| WO2017176873A1 (fr) | 2016-04-06 | 2017-10-12 | The Coca-Cola Company | Amélioration de la douceur et du goût d'édulcorants à base de glycoside de stéviol ou de mogroside |
| US11447516B2 (en) | 2016-10-04 | 2022-09-20 | The Coca-Cola Company | Diterpene glycosides containing an ent-atisene core, compositions and methods |
| EP3528640A4 (fr) | 2016-10-20 | 2020-09-16 | The Coca-Cola Company | Glycosides diterpéniques isolés à partir de stevia, compositions et procédés |
| US11653606B2 (en) | 2016-12-01 | 2023-05-23 | Purecircle Usa Inc. | Stevia plant and uses thereof |
| CA3061045A1 (fr) | 2017-04-25 | 2018-11-01 | The Coca-Cola Company | Amelioration de la sucrosite et du gout d'edulcorants a base de glycoside de steviol et de mogroside avec des dihydrochalcones |
| BR112020006822B1 (pt) | 2017-10-06 | 2023-03-07 | Cargill, Incorporated | Método para fazer uma composição de extrato de erva mate |
| CN107955054A (zh) * | 2017-11-30 | 2018-04-24 | 陕西海斯夫生物工程有限公司 | 一种薄膜反应与分离耦合制备植物甾醇酯的方法 |
| WO2019213042A1 (fr) | 2018-04-30 | 2019-11-07 | The Coca-Cola Company | Procédés d'amélioration de la solubilité de mélanges de glycosides de stéviol et utilisations |
| EP4223146A1 (fr) | 2018-05-08 | 2023-08-09 | EPC Natural Products Co., Ltd. | Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation |
| WO2020123067A2 (fr) | 2018-10-12 | 2020-06-18 | Epc Natural Products Co., Ltd. | Compositions d'édulcorant et d'arôme, leurs procédés de fabrication et leurs procédés d'utilisation |
| JP2022527518A (ja) | 2019-04-06 | 2022-06-02 | カーギル インコーポレイテッド | 感覚改質剤 |
| US20220295833A1 (en) | 2019-09-27 | 2022-09-22 | The Coca-Cola Company | Sweetener blends with improved taste |
| EP4395568A1 (fr) | 2021-09-01 | 2024-07-10 | The Coca-Cola Company | Procédés et compositions comprenant de la caféine et/ou un dérivé de celle-ci et un polyphénol |
| WO2024081959A2 (fr) | 2022-10-14 | 2024-04-18 | The Coca-Cola Company | Procédés et compositions servant à améliorer des fonctions cognitives et d'humeur |
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| US2693484A (en) * | 1951-04-07 | 1954-11-02 | Pittsburgh Plate Glass Co | Noncatalytic ester exchange reaction of beta-keto carboxylic acid esters |
| JPS5111113B1 (fr) * | 1968-12-04 | 1976-04-08 | ||
| CA928140A (en) | 1969-07-17 | 1973-06-12 | A. Erickson Billy | Clear cooking and salad oils having hypocholesterolemic properties |
| JPS5923320B2 (ja) * | 1979-10-31 | 1984-06-01 | 花王株式会社 | 分岐脂肪酸コレステリルエステル |
| JPS60199809A (ja) * | 1984-03-23 | 1985-10-09 | Yoshikawa Seiyu Kk | 化粧料用基材 |
| US4822875A (en) * | 1986-12-17 | 1989-04-18 | The Procter & Gamble Company | Sucrose polyesters which behave like cocoa butters |
| US5061503A (en) * | 1989-06-14 | 1991-10-29 | The Procter & Gamble Company | Simulated cheese products with reduced animal fat and calories |
| AU664827B2 (en) | 1991-05-03 | 1995-12-07 | Raisio Benecol Ltd. | A substance for lowering high cholesterol level in serum and a method for preparing the same |
| US5247083A (en) * | 1992-07-10 | 1993-09-21 | Syntex (U.S.A.) Inc. | Direct esterification of mycophenolic acid |
| AU7250694A (en) | 1993-06-25 | 1995-01-17 | Biosphere Technologies Inc. | Dietary supplement incorporating beta-sitosterol and pectin |
| GB2283435B (en) * | 1993-11-04 | 1997-03-26 | Ebortec Limited | A deodoriser |
| US5512691A (en) * | 1994-11-07 | 1996-04-30 | Eastman Chemical Company | Process for the production of tocopherol concentrates |
| DE19716686A1 (de) * | 1997-04-21 | 1998-10-22 | Basf Ag | Verfahren zur Herstellung von Estern mit geringem Restsäuregehalt aus alpha,beta-ethylenisch ungesättigten Carbonsäuren und Hydroxylgruppen-haltigen Polymerisaten |
| DE69818942T2 (de) | 1997-08-22 | 2004-09-09 | Unilever N.V. | Stanolester enthaltende Zusammensetzungen |
| EP0897970B1 (fr) | 1997-08-22 | 2004-09-29 | Unilever N.V. | Procédé de production d'esters de stanol |
| US6394230B1 (en) | 1997-12-16 | 2002-05-28 | Cognis Corporation | Sterol esters as food additives |
| AU2660099A (en) | 1998-02-06 | 1999-08-23 | Medical Isotopes Inc. | Readily absorbable phytosterols to treat hypercholesterrolemia |
| FI109327B (fi) | 1998-02-27 | 2002-07-15 | Spice Sciences Oy | Menetelmä seerumin kokonais- ja LDL-kolestrolipitoisuutta alentavan beta-sitosterolin rasvamaisen seoksen valmistamiseksi |
| US6025348A (en) | 1998-04-30 | 2000-02-15 | Kao Corporation | Oil and fat composition containing phytosterol |
| IN186960B (fr) * | 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 |
| US6410758B2 (en) * | 1999-05-24 | 2002-06-25 | Mcneil-Ppc, Inc. | Preparation of sterol and stanol-esters |
-
1999
- 1999-05-24 US US09/317,712 patent/US6410758B2/en not_active Expired - Lifetime
-
2000
- 2000-05-22 AU AU36347/00A patent/AU779024B2/en not_active Ceased
- 2000-05-22 NZ NZ504693A patent/NZ504693A/en unknown
- 2000-05-23 AT AT00304364T patent/ATE334138T1/de active
- 2000-05-23 JP JP2000151859A patent/JP2001002697A/ja active Pending
- 2000-05-23 ES ES00304364T patent/ES2267462T3/es not_active Expired - Lifetime
- 2000-05-23 DK DK00304364T patent/DK1067135T3/da active
- 2000-05-23 MX MXPA00005063A patent/MXPA00005063A/es active IP Right Grant
- 2000-05-23 PT PT00304364T patent/PT1067135E/pt unknown
- 2000-05-23 EP EP00304364A patent/EP1067135B1/fr not_active Expired - Lifetime
- 2000-05-23 DE DE60029518T patent/DE60029518T2/de not_active Expired - Lifetime
- 2000-05-23 NO NO20002635A patent/NO322767B1/no unknown
- 2000-05-23 AR ARP000102509A patent/AR029636A1/es not_active Application Discontinuation
- 2000-05-23 CA CA002309224A patent/CA2309224C/fr not_active Expired - Fee Related
- 2000-05-24 BR BR0001899-6A patent/BR0001899A/pt not_active IP Right Cessation
-
2002
- 2002-05-06 US US10/139,760 patent/US6635774B2/en not_active Expired - Lifetime
-
2006
- 2006-09-26 CY CY20061101384T patent/CY1105242T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE334138T1 (de) | 2006-08-15 |
| NO20002635D0 (no) | 2000-05-23 |
| EP1067135A3 (fr) | 2002-11-27 |
| ES2267462T3 (es) | 2007-03-16 |
| AR029636A1 (es) | 2003-07-10 |
| PT1067135E (pt) | 2006-10-31 |
| EP1067135B1 (fr) | 2006-07-26 |
| CA2309224C (fr) | 2006-06-27 |
| CA2309224A1 (fr) | 2000-11-24 |
| NO20002635L (no) | 2000-11-27 |
| EP1067135A2 (fr) | 2001-01-10 |
| DE60029518T2 (de) | 2007-07-26 |
| US6410758B2 (en) | 2002-06-25 |
| CY1105242T1 (el) | 2010-03-03 |
| US20020010349A1 (en) | 2002-01-24 |
| DE60029518D1 (de) | 2006-09-07 |
| NZ504693A (en) | 2001-09-28 |
| AU3634700A (en) | 2000-11-30 |
| AU779024B2 (en) | 2005-01-06 |
| MXPA00005063A (es) | 2002-03-08 |
| JP2001002697A (ja) | 2001-01-09 |
| BR0001899A (pt) | 2001-01-02 |
| US6635774B2 (en) | 2003-10-21 |
| US20020132804A1 (en) | 2002-09-19 |
| DK1067135T3 (da) | 2006-11-06 |
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