EP1742545A1 - Water continuous product comprising sterol or stanolester and a tocopherol - Google Patents
Water continuous product comprising sterol or stanolester and a tocopherolInfo
- Publication number
- EP1742545A1 EP1742545A1 EP05716179A EP05716179A EP1742545A1 EP 1742545 A1 EP1742545 A1 EP 1742545A1 EP 05716179 A EP05716179 A EP 05716179A EP 05716179 A EP05716179 A EP 05716179A EP 1742545 A1 EP1742545 A1 EP 1742545A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- tocopherol
- fatty acid
- sterol
- water continuous
- acid ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229930003799 tocopherol Natural products 0.000 title claims abstract description 40
- 239000011732 tocopherol Substances 0.000 title claims abstract description 40
- 229930182558 Sterol Natural products 0.000 title claims abstract description 37
- 235000003702 sterols Nutrition 0.000 title claims abstract description 37
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 title claims abstract description 37
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 235000010384 tocopherol Nutrition 0.000 title claims abstract description 34
- 229960001295 tocopherol Drugs 0.000 title claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 150000003432 sterols Chemical class 0.000 title claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 34
- 229930195729 fatty acid Natural products 0.000 claims abstract description 34
- 239000000194 fatty acid Substances 0.000 claims abstract description 34
- -1 sterol fatty acid ester Chemical class 0.000 claims abstract description 27
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 claims description 35
- 235000019197 fats Nutrition 0.000 claims description 19
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 claims description 18
- 235000010389 delta-tocopherol Nutrition 0.000 claims description 18
- 239000002446 δ-tocopherol Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 150000004665 fatty acids Chemical group 0.000 claims description 14
- 235000010382 gamma-tocopherol Nutrition 0.000 claims description 8
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000002478 γ-tocopherol Substances 0.000 claims description 8
- 235000019486 Sunflower oil Nutrition 0.000 claims description 7
- 235000000346 sugar Nutrition 0.000 claims description 7
- 239000002600 sunflower oil Substances 0.000 claims description 7
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 claims description 7
- 235000013365 dairy product Nutrition 0.000 claims description 6
- 102000014171 Milk Proteins Human genes 0.000 claims description 4
- 108010011756 Milk Proteins Proteins 0.000 claims description 4
- 235000021239 milk protein Nutrition 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- 235000019485 Safflower oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 235000005713 safflower oil Nutrition 0.000 claims description 3
- 239000003813 safflower oil Substances 0.000 claims description 3
- 235000019871 vegetable fat Nutrition 0.000 claims description 3
- 229940087168 alpha tocopherol Drugs 0.000 claims description 2
- 229960000984 tocofersolan Drugs 0.000 claims description 2
- 235000004835 α-tocopherol Nutrition 0.000 claims description 2
- 239000002076 α-tocopherol Substances 0.000 claims description 2
- 229940066595 beta tocopherol Drugs 0.000 claims 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N beta-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 claims 1
- 239000011590 β-tocopherol Substances 0.000 claims 1
- 235000007680 β-tocopherol Nutrition 0.000 claims 1
- 235000019640 taste Nutrition 0.000 abstract description 8
- 239000000047 product Substances 0.000 description 55
- 239000003925 fat Substances 0.000 description 15
- 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 10
- 239000004615 ingredient Substances 0.000 description 8
- 235000013618 yogurt Nutrition 0.000 description 7
- 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 6
- 235000019149 tocopherols Nutrition 0.000 description 6
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 235000018102 proteins Nutrition 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 239000006071 cream Substances 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229940076810 beta sitosterol Drugs 0.000 description 3
- 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 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 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 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 3
- 229950005143 sitosterol Drugs 0.000 description 3
- 229930003802 tocotrienol Natural products 0.000 description 3
- 239000011731 tocotrienol Substances 0.000 description 3
- 235000019148 tocotrienols Nutrition 0.000 description 3
- 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 2
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-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
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 235000000431 campesterol Nutrition 0.000 description 2
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000013310 margarine Nutrition 0.000 description 2
- 239000003264 margarine Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229940068065 phytosterols Drugs 0.000 description 2
- 239000006041 probiotic Substances 0.000 description 2
- 235000018291 probiotics Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000020183 skimmed milk Nutrition 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
- 235000016831 stigmasterol Nutrition 0.000 description 2
- 229940032091 stigmasterol Drugs 0.000 description 2
- 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 2
- 229940068778 tocotrienols Drugs 0.000 description 2
- VGSSUFQMXBFFTM-UHFFFAOYSA-N (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol Natural products C1C(O)C2(O)CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 VGSSUFQMXBFFTM-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 1
- GPAYKKAWEFDIFJ-UHFFFAOYSA-N 2-methyl-3,4-dihydro-2h-chromen-6-ol Chemical class OC1=CC=C2OC(C)CCC2=C1 GPAYKKAWEFDIFJ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- BBTIMXAYZRWPNG-UHFFFAOYSA-N 3beta,Delta4-stigmasten-3-ol Natural products C1CC2=CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BBTIMXAYZRWPNG-UHFFFAOYSA-N 0.000 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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 241000186000 Bifidobacterium Species 0.000 description 1
- OILXMJHPFNGGTO-NRHJOKMGSA-N Brassicasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 OILXMJHPFNGGTO-NRHJOKMGSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 244000199885 Lactobacillus bulgaricus Species 0.000 description 1
- 235000013960 Lactobacillus bulgaricus Nutrition 0.000 description 1
- 244000199866 Lactobacillus casei Species 0.000 description 1
- 235000013958 Lactobacillus casei Nutrition 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- OILXMJHPFNGGTO-ZRUUVFCLSA-N UNPD197407 Natural products 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](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZRUUVFCLSA-N 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
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 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
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- QADVIPISOOQJMJ-WLKYTNTRSA-N beta-stigmasterol Natural products CCC(CC)C=C[C@@H](C)[C@H]1CC[C@@H]2[C@@H]1CC[C@H]3[C@H]2CC=C4C[C@@H](O)CC[C@]34C QADVIPISOOQJMJ-WLKYTNTRSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000004420 brassicasterol Nutrition 0.000 description 1
- OILXMJHPFNGGTO-ZAUYPBDWSA-N brassicasterol 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](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940071162 caseinate Drugs 0.000 description 1
- KJDZDTDNIULJBE-QXMHVHEDSA-N cetoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCCCC(O)=O KJDZDTDNIULJBE-QXMHVHEDSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009884 interesterification Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 229940004208 lactobacillus bulgaricus Drugs 0.000 description 1
- 229940017800 lactobacillus casei Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 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
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 235000004213 low-fat Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 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
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000005195 poor health Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 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 1
- 229940001941 soy protein Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 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
- HCXVJBMSMIARIN-UHFFFAOYSA-N stigmasterol Chemical compound C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 HCXVJBMSMIARIN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000008924 yoghurt drink Nutrition 0.000 description 1
- 235000019145 α-tocotrienol Nutrition 0.000 description 1
- 150000003773 α-tocotrienols Chemical class 0.000 description 1
- 235000019151 β-tocotrienol Nutrition 0.000 description 1
- 150000003782 β-tocotrienols Chemical class 0.000 description 1
- 125000003810 γ-tocopherol group Chemical group 0.000 description 1
- 235000019150 γ-tocotrienol Nutrition 0.000 description 1
- 150000003786 γ-tocotrienols Chemical class 0.000 description 1
- 235000019144 δ-tocotrienol Nutrition 0.000 description 1
- 150000003790 δ-tocotrienols Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/385—Concentrates of non-alcoholic beverages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
Definitions
- Water continuous product comprising sterol or stanolester and a tocopherol
- the invention relates to water continuous products such as milk and yoghurt comprising a sterol or stanol fatty acid ester and an antioxidant comprising tocopherol.
- Food products for lowering cholesterol levels in blood are known for several years.
- Commercial products that contain ingredients that influence blood cholesterol lowering when daily consumed are for example Becel pro.activTM and BenecolTM.
- ingredients on which the cholesterol lowering effect is based are sterol fatty acid ester and stanol fatty acid ester. These were initially included in products rich in fat such as margarine. One of the reasons for this was that their incorporation in low fat products was considered difficult .
- WO-A- 99/44442 relates to stable, homogeneous, emulsifier free suspensions of sterol compounds.
- EP-A-1212945 discloses dairy-based beverages fortified with stanolester for cholesterol lowering. The amount of stanolester is from 0.2 to about 2 wt%.
- tocopherol wherein the amount of y- or ⁇ - tocopherol is at least 60 wt% of the total weight of tocopherol, leads to surprisingly good products which do not suffer so much from the development of off taste.
- WO-A-02/07235 discloses anti-inflammatory compositions comprising sterols and tocotrienols or polyphenols.
- the preferred tocotrienols are alpha, beta, gamma and delta tocotrienols .
- WO-A-02/060272 discloses edible oils comprising at least one of free sterol or steryl ester and preferably a compound that reduces cholesterol synthesis in a human patient, such as at least one tocotrienol .
- WO-A-99/25361 discloses hypocholesteroaemic preparations comprising stenolester and preferably a tocopherol .
- the most preferred tocopherol is alpha-tocopherol .
- the invention relates to a water continuous product comprising up to 10 wt% fat, a sterol and/or stanol fatty acid ester, and a tocopherol comprising gamma and/or delta tocopherol , wherein the amount of ⁇ , ⁇ - tocopherol is at least 60wt% of the total amount of tocopherol .
- the invention relates to water continuous products.
- the products comprise a continuous aqueous phase in which other ingredients may be present.
- these other ingredients are dissolved, dispersed or emulsified in the aqueous phase.
- the continuous phase is formed by the fat phase such as in butter or margarine.
- the dispersed phase is water in the form of droplets emulsified in the fat phase.
- the products according to the invention comprise a sterol and/or stanol fatty acid ester.
- Sterols or phytosterols also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4 , 4 ' -dimethylsterols .
- oils they mainly exist as free sterols and sterol esters of fatty acids although sterol glucosides and acylated sterol glucosides are also present.
- esterified sterol or stanol is selected from the group comprising fatty acid ester of ⁇ -sitosterol, ⁇ - sitostanol, campesterol, campestanol, stigmasterol , brassicasterol, brassicastanol or a mixture thereof.
- the sterols or stanols are esterified with a fatty acid.
- the sterols or stanols are esterified with one or more C2-22 fatty acids.
- C 2 - 22 fatty acid refers to any molecule comprising a C 2 - 22 main chain and at least one acid group.
- the C2- 22 main chain may be partially substituted or side chains may be present.
- the C2-2 2 fatty acids are linear molecules comprising one or two acid group (s) as end group (s). Most preferred are linear C 8 . 22 fatty acids as these occur in natural oils.
- Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid.
- Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid.
- Most preferred are myristic acid, lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
- a mixture of fatty acids may be used for esterification of the sterols or stanols.
- a mixture of fatty acids may be used for esterification of the sterols or stanols.
- the fatty acid in the esterified sterol or stanol is derived from sunflower oil, rapeseed oil, safflower oil, coconut oil, or a mixture thereof.
- the fatty acid in the esterified sterol or stanol is derived from sunflower oil .
- the products comprise a combination of a sterol fatty acid ester and a stanol fatty acid ester.
- the products comprise unesterified "free” , sterol or stanol in addition to the esterified sterol or stanol.
- the total amount of sterol and stanol fatty acid ester is preferably from 0.1 to 10 wt%. More preferred, the amount is from 0.5 to 5 wt%, most preferred from 2 to 5 wt% on total product weight.
- the products comprise a tocopherol .
- the tocopherol is selected from the group comprising ⁇ -, ⁇ -, ⁇ - # ⁇ - tocopherol .
- Tocopherols are derivatives of 2-methyl-6-chromanol with an attachment of a saturated 16-carbon isoprenoid chain at C-2.
- the structures of ⁇ - , ⁇ - , ⁇ , and ⁇ - tocopherol are presented in figure 1.
- the level of tocopherol in a product may be obtained by routine measures including extraction of tocopherols from the samples, followed by quantification using HPLC.
- Tocopherols are naturally present in oil seeds, grains, leaves, and other green parts of higher plants. Suitable sources of tocopherol are e.g. soy bean and corn oil.
- At least 60 wt%, preferably at least 70 wt%, more preferred at least 80 wt%, even more preferred at least 94 wt% is in the form of ⁇ - , ⁇ - tocopherol .
- the total amount of y-, ⁇ - tocopherol is at least 60 wt% on the total weight of tocopherol . It was found that products comprising sterol or stanol ester, especially those of sunflower oil, showed highly improved taste stability and less development of off flavour when using this specific tocopherol composition.
- the tocopherol comprises at least 60wt% ⁇ tocopherol , even more preferred from 60 to 95 wt% ⁇ -tocopherol .
- the total amount of tocopherol to achieve the desired level of off taste reduction is preferably from 10 to 50.000 ppm, more preferred from 10 to 5000 ppm, more preferred from 10 to 1000 ppm, even more preferred from 10 to 500 ppm, most preferred from 50 to 500 ppm on total product.
- the products according to the invention comprise up to 10% fat. This implies that the products may also be fat free.
- Preferred products are selected from the group comprising drinks such as milk or yoghurt drinks, yoghurts, creams, liquid products based on fruit and protein, such as fusion drinks.
- the fat may be of any origin. Suitable fats therefore include vegetable fat such as sunflower oil, rapeseed oil, olive oil, coconut oil, safflower oil and dairy fat.
- Preferred products comprise dairy fat, preferably in an amount from 20 to 80 wt% on total fat. Most preferred products comprise a combination of dairy fat and vegetable fat.
- the dairy fat may be added as such or may be part of any of the ingredients that are included in the product such as milk proteins or cream.
- the products comprise further ingredients such as thickeners, emulsifier, sugar, protein, taste and flavour modifiers, fruit or fruit concentrate, acidifier, cultures.
- further ingredients such as thickeners, emulsifier, sugar, protein, taste and flavour modifiers, fruit or fruit concentrate, acidifier, cultures.
- the products comprise protein, preferably in an amount of from 0.5 to 10 wt%.
- the most preferred protein is milk protein such as derived from fresh milk, yoghurt, quark, skimmed milk powder, whey powder, caseinate, cream.
- An alternative protein source is vegetable protein, preferably soy protein.
- Preferred products comprise a living culture.
- a living culture is a culture which has not been inactivated by a heating step and which continues fermentation in pack. Such cultures are also referred to as yoghurt cultures and probiotics. Suitable cultures include Lactobacillus Bulgaricus, Lactobacillus rhawnosus, Streptococcus thermopilus, Bifidobacterium, Lactobacillus casei . It was found that such cultures may also positively contribute to off taste reduction.
- the products are concentrated drinks comprising up to 5 wt% fat, from 1.5 to 4 wt% sterol and/or stanol fatty acid ester, milk protein, water and sugar or a sugar replacer (sugar being preferred) and preferably emulsifier.
- Even more preferred those products are acidified, preferably fermented products, with a pH in the range from 3.8 to 6, preferably from 4 to 5.
- the products may be prepared by any suitable process.
- a preferred process comprises the steps of preparing a premix of the tocopherol and the sterol and/or stanol fatty acid ester. This premix is added to the aqueous phase. The other ingredients may be added at any stage of the process.
- the invention is illustrated by the following non-limiting examples .
- ⁇ -tocopherol was derived from a tocopherol mixture comprising 60% ⁇ -tocopherol and 24% ⁇ -tocopherol .
- the ⁇ -tocopherol was derived from a tocopherol mixture comprising 86% ⁇ -tocopherol.
- a premix was prepared comprising milk, cream and water at a temperature of about 60 °C. Tocopherols and sterolester was weighed and mixed with a spoon. The aqueous mixture was subjected to vigorous stirring in a TurraxTM. While the Turrax TM was run at low speed of about 3500 rpm, the powder mix of sugar and skim milk powder was mixed in, followed by the sterolester composition. Mixing was continued at higher speed for some more minutes. The mixture was then heated to 75 °C and pasteurised. Next the mix was homogenised at 200 bar and cooled to fermentation temperature of about 43 °C. A separately prepared yoghurt culture was used to inoculate the product. Fermentation was continued until a pH of about 4.3 was reached. The fermented product was sturred and homogenised at about 50 bar before it was filled into sterile containers. The product was cooled and stored at 5 °C.
- a trained panel of experts evaluated the products directly after preparation and after storage for 3 weeks at 5 °C.
- the panel was trained on tasting off flavor and compared the products to a commercially available drink yoghurt of the brand ActimelTM, which is free of sterol or stanol ester.
- the products were scored as good, acceptable or bad.
- Comparative example "C” was evaluated as bad by all participants for the sample directly after preparation and after 3 weeks of storage .
- Product according to example 1 was evaluated as good by 25% of the test panel and acceptable by 50% of the test panel directly after preparation. It was found good by about 33% of the test panel and acceptable by about 35% of the test panel after 3 weeks.
- Product of example 2 was evaluated as good by 38% of the panel and acceptable by 40% of the panel directly after preparation. After 3 weeks 50% of the panel found it good and 50% acceptable.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Botany (AREA)
- Mycology (AREA)
- Dairy Products (AREA)
Abstract
Water continuous products comprising a specific tocopherol in combination with sterol fatty acid ester and/or stanol fatty acid ester are taste stable on storage.
Description
Water continuous product comprising sterol or stanolester and a tocopherol
Field of the invention
The invention relates to water continuous products such as milk and yoghurt comprising a sterol or stanol fatty acid ester and an antioxidant comprising tocopherol.
Background to the invention
Food products for lowering cholesterol levels in blood are known for several years. Commercial products that contain ingredients that influence blood cholesterol lowering when daily consumed are for example Becel pro.activ™ and Benecol™. Examples of the ingredients on which the cholesterol lowering effect is based are sterol fatty acid ester and stanol fatty acid ester. These were initially included in products rich in fat such as margarine. One of the reasons for this was that their incorporation in low fat products was considered difficult .
WO-A- 99/44442 relates to stable, homogeneous, emulsifier free suspensions of sterol compounds. EP-A-1212945 discloses dairy-based beverages fortified with stanolester for cholesterol lowering. The amount of stanolester is from 0.2 to about 2 wt%.
Although the products according to EP-A-1212945 may provide suitable short term stability we have found that such water continuous products comprising sterol or stanol fatty acid esters may suffer from off taste development on storage over times of several weeks.
In view of the product segment being products with a health claim the route to solving this problem should be one which is acceptable from a health perspective and is not leading to objections with respect to addition of chemicals with poor health image.
We have surprisingly found that the use of tocopherol wherein the amount of y- or δ- tocopherol is at least 60 wt% of the total weight of tocopherol, leads to surprisingly good products which do not suffer so much from the development of off taste.
Products comprising tocopherol and sterol or stanol are already known in the art .
WO-A-02/07235 discloses anti-inflammatory compositions comprising sterols and tocotrienols or polyphenols. The preferred tocotrienols are alpha, beta, gamma and delta tocotrienols .
WO-A-02/060272 discloses edible oils comprising at least one of free sterol or steryl ester and preferably a compound that reduces cholesterol synthesis in a human patient, such as at least one tocotrienol .
WO-A-99/25361 discloses hypocholesteroaemic preparations comprising stenolester and preferably a tocopherol . The most preferred tocopherol is alpha-tocopherol .
Summary of the invention
The invention relates to a water continuous product comprising up to 10 wt% fat, a sterol and/or stanol fatty acid ester, and
a tocopherol comprising gamma and/or delta tocopherol , wherein the amount of γ~ , δ- tocopherol is at least 60wt% of the total amount of tocopherol .
Detailed description of the invention
In the context of this specification and claims all percentage is a weight percentage on total product weight.
The invention relates to water continuous products. This means that the products comprise a continuous aqueous phase in which other ingredients may be present. For example these other ingredients are dissolved, dispersed or emulsified in the aqueous phase. This is contrary to fat continuous products wherein the continuous phase is formed by the fat phase such as in butter or margarine. In these products the dispersed phase is water in the form of droplets emulsified in the fat phase.
The products according to the invention comprise a sterol and/or stanol fatty acid ester.
Sterols or phytosterols, also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4 , 4 ' -dimethylsterols . In oils they mainly exist as free sterols and sterol esters of fatty acids although sterol glucosides and acylated sterol glucosides are also present. There are three major phytosterols namely beta-sitosterol , stigmasterol and campesterol . Schematic drawings of the components meant are as given in "Influence of Processing on Sterols of Edible
Vegetable Oils", S.P. Kochhar; Prog. Lipid Res . 22: pp. 161- 188.
The respective 5 alpha- saturated derivatives such as sitostanol, campestanol and ergostanol and their derivatives are in this specification referred to as stands.
Preferably the esterified sterol or stanol is selected from the group comprising fatty acid ester of β-sitosterol, β- sitostanol, campesterol, campestanol, stigmasterol , brassicasterol, brassicastanol or a mixture thereof.
The sterols or stanols are esterified with a fatty acid. Preferably the sterols or stanols are esterified with one or more C2-22 fatty acids. For the purpose of the invention the term C2-22 fatty acid refers to any molecule comprising a C2-22 main chain and at least one acid group. Although not preferred within the present context the C2-22 main chain may be partially substituted or side chains may be present. Preferably, however the C2-22 fatty acids are linear molecules comprising one or two acid group (s) as end group (s). Most preferred are linear C8.22 fatty acids as these occur in natural oils.
Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid. Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid. Most preferred are myristic acid, lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
When desired a mixture of fatty acids may be used for esterification of the sterols or stanols. For example, it is possible to use a naturally occurring fat or oil as a source of
the fatty acid and to carry out the esterification via an interesterification reaction.
In a preferred embodiment, the fatty acid in the esterified sterol or stanol is derived from sunflower oil, rapeseed oil, safflower oil, coconut oil, or a mixture thereof.
Most preferred the fatty acid in the esterified sterol or stanol is derived from sunflower oil .
Optionally the products comprise a combination of a sterol fatty acid ester and a stanol fatty acid ester.
Optionally the products comprise unesterified "free" , sterol or stanol in addition to the esterified sterol or stanol.
The total amount of sterol and stanol fatty acid ester is preferably from 0.1 to 10 wt%. More preferred, the amount is from 0.5 to 5 wt%, most preferred from 2 to 5 wt% on total product weight.
The products comprise a tocopherol . Preferably the tocopherol is selected from the group comprising α-, β-, γ-# δ- tocopherol .
Tocopherols are derivatives of 2-methyl-6-chromanol with an attachment of a saturated 16-carbon isoprenoid chain at C-2. The structures of α- , β- , γ~ , and δ- tocopherol are presented in figure 1. The level of tocopherol in a product may be obtained by routine measures including extraction of tocopherols from the samples, followed by quantification using HPLC.
Tocopherols are naturally present in oil seeds, grains, leaves, and other green parts of higher plants. Suitable sources of tocopherol are e.g. soy bean and corn oil.
Of all tocopherol present in the product, at least 60 wt%, preferably at least 70 wt%, more preferred at least 80 wt%, even more preferred at least 94 wt% is in the form of γ- , δ- tocopherol . This means that the total amount of y-, δ- tocopherol is at least 60 wt% on the total weight of tocopherol . It was found that products comprising sterol or stanol ester, especially those of sunflower oil, showed highly improved taste stability and less development of off flavour when using this specific tocopherol composition.
More preferred from 60 to 99wt%, more preferred from 60 to 95 wt%, even more preferred 70 to 95 wt% of the tocopherol present in the product is γ-tocopherol and δ- tocopherol.
More preferred, the tocopherol comprises at least 60wt% γ~ tocopherol , even more preferred from 60 to 95 wt% γ-tocopherol .
The total amount of tocopherol to achieve the desired level of off taste reduction is preferably from 10 to 50.000 ppm, more preferred from 10 to 5000 ppm, more preferred from 10 to 1000 ppm, even more preferred from 10 to 500 ppm, most preferred from 50 to 500 ppm on total product.
The products according to the invention comprise up to 10% fat. This implies that the products may also be fat free. Preferred products are selected from the group comprising drinks such as milk or yoghurt drinks, yoghurts, creams, liquid products based on fruit and protein, such as fusion drinks.
The fat may be of any origin. Suitable fats therefore include vegetable fat such as sunflower oil, rapeseed oil, olive oil, coconut oil, safflower oil and dairy fat. Preferred products comprise dairy fat, preferably in an amount from 20 to 80 wt% on total fat. Most preferred products comprise a combination of dairy fat and vegetable fat. The dairy fat may be added as such or may be part of any of the ingredients that are included in the product such as milk proteins or cream.
Optionally the products comprise further ingredients such as thickeners, emulsifier, sugar, protein, taste and flavour modifiers, fruit or fruit concentrate, acidifier, cultures.
Preferably the products comprise protein, preferably in an amount of from 0.5 to 10 wt%. The most preferred protein is milk protein such as derived from fresh milk, yoghurt, quark, skimmed milk powder, whey powder, caseinate, cream. An alternative protein source is vegetable protein, preferably soy protein.
Preferred products comprise a living culture. In this context a living culture is a culture which has not been inactivated by a heating step and which continues fermentation in pack. Such cultures are also referred to as yoghurt cultures and probiotics. Suitable cultures include Lactobacillus Bulgaricus, Lactobacillus rhawnosus, Streptococcus thermopilus, Bifidobacterium, Lactobacillus casei . It was found that such cultures may also positively contribute to off taste reduction.
Most preferred the products are concentrated drinks comprising up to 5 wt% fat, from 1.5 to 4 wt% sterol and/or stanol fatty
acid ester, milk protein, water and sugar or a sugar replacer (sugar being preferred) and preferably emulsifier.
Even more preferred those products are acidified, preferably fermented products, with a pH in the range from 3.8 to 6, preferably from 4 to 5.
The products may be prepared by any suitable process. A preferred process comprises the steps of preparing a premix of the tocopherol and the sterol and/or stanol fatty acid ester. This premix is added to the aqueous phase. The other ingredients may be added at any stage of the process.
In the process it is preferred that all ingredients are mixed, subjected to pasteurizing, homogenizing and cooling. For acidified products it is preferred to include a fermentation step which is followed by homogenizing and cold filling to preserve probiotics activity.
The invention is illustrated by the following non-limiting examples .
Example 1, 2
A yoghurt was prepared with the product composition in wt% on total product as presented in table 1.
Table 1: product composition
Specification of tocopherols: γ-tocopherol was derived from a tocopherol mixture comprising 60% γ-tocopherol and 24% δ-tocopherol .
The δ-tocopherol was derived from a tocopherol mixture comprising 86% δ-tocopherol.
Process
A premix was prepared comprising milk, cream and water at a temperature of about 60 °C. Tocopherols and sterolester was weighed and mixed with a spoon. The aqueous mixture was subjected to vigorous stirring in a Turrax™. While the Turrax ™ was run at low speed of about 3500 rpm, the powder mix of sugar and skim milk powder was mixed in, followed by the sterolester composition. Mixing was continued at higher speed for some more minutes. The mixture was then heated to 75 °C and pasteurised. Next the mix was homogenised at 200 bar and cooled to fermentation temperature of about 43 °C.
A separately prepared yoghurt culture was used to inoculate the product. Fermentation was continued until a pH of about 4.3 was reached. The fermented product was sturred and homogenised at about 50 bar before it was filled into sterile containers. The product was cooled and stored at 5 °C.
Tasting of the products and identification of off flavour:
A trained panel of experts evaluated the products directly after preparation and after storage for 3 weeks at 5 °C. The panel was trained on tasting off flavor and compared the products to a commercially available drink yoghurt of the brand Actimel™, which is free of sterol or stanol ester. The products were scored as good, acceptable or bad.
As a comparison example products were made with the composition of example 1 and 2 except that the tocopherols were not included. This example is referred to as "C" .
Comparative example "C" was evaluated as bad by all participants for the sample directly after preparation and after 3 weeks of storage .
Product according to example 1 was evaluated as good by 25% of the test panel and acceptable by 50% of the test panel directly after preparation. It was found good by about 33% of the test panel and acceptable by about 35% of the test panel after 3 weeks. Product of example 2 was evaluated as good by 38% of the panel and acceptable by 40% of the panel directly after preparation. After 3 weeks 50% of the panel found it good and 50% acceptable.
These results show that the addition of δ-tocopherol or γ~ tocopherol results in reduced off taste in water continuous products comprising a fatty acid ester of sunflower oil and beta sitosterol.
Claims
1. Water continuous product comprising up to 10 wt% fat, a sterol fatty acid ester and/or stanol fatty acid ester, and a tocopherol comprising γ- , and/or δ- tocopherol, characterized in that the amount of γ- , δ- tocopherol is at least 60wt% of the total amount of tocopherol.
2. Water continuous product according to claim 1 wherein the product comprises tocopherol, which is characterized in that the tocopherol comprises at least 70wt% γ-tocopherol and δ- tocopherol .
3. Water continuous product according to claim 2 wherein the tocopherol comprises at least 60wt% γ-tocopherol .
4. Water continuous product according to any of claims 1-3 wherein the fatty acid part of the sterol or stanol fatty acid esters is selected from the group of fatty acids comprising those derived from sunflower oil, rapeseed oil, safflower oil, coconut oil, or a mixture thereof.
5. Water continuous product according to claim 4 wherein the fatty acid part is derived from sunflower oil.
6. Water continuous products according to any of claims 1-5 comprising a living culture.
7. Water continuous product according to any of claims 1-6 wherein the fat comprises a combination of vegetable fat and dairy fat .
8. Water continuous product according to any of claims 1-7 wherein the total amount of sterol fatty acid ester and stanol fatty acid ester is from 1 to 10 wt% on total product weight .
9. Water continuous product according to any of claims 1-8 wherein the amount of tocopherol is in total from 10 to 5000 ppm.
10. Concentrated drink comprising up to 5 wt% fat, from 1.5 to 4 wt% sterol fatty acid ester and/or stanol fatty acid ester, milk protein, water and sugar or a sugar replacer and further comprising a tocopherol comprising γ- , and/or δ- tocopherol, characterized in that the amount of γ-( δ- tocopherol is at least 60wt% of the total amount of tocopherol .
1/1
Trivial name R1 R1 R3 α-tocopherol CH3 CH3 CH3 β-tocopherol CH3 H CH3 γ-tocopherol H CH3 CH3 δ-tocopherol H H CH3
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05716179A EP1742545A1 (en) | 2004-04-16 | 2005-03-16 | Water continuous product comprising sterol or stanolester and a tocopherol |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04076167 | 2004-04-16 | ||
EP05716179A EP1742545A1 (en) | 2004-04-16 | 2005-03-16 | Water continuous product comprising sterol or stanolester and a tocopherol |
PCT/EP2005/002878 WO2005099484A1 (en) | 2004-04-16 | 2005-03-16 | Water continuous product comprising sterol or stanolester and a tocopherol |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1742545A1 true EP1742545A1 (en) | 2007-01-17 |
Family
ID=34928163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05716179A Withdrawn EP1742545A1 (en) | 2004-04-16 | 2005-03-16 | Water continuous product comprising sterol or stanolester and a tocopherol |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1742545A1 (en) |
AU (1) | AU2005232369A1 (en) |
WO (1) | WO2005099484A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2070429A1 (en) | 2007-12-13 | 2009-06-17 | Cognis IP Management GmbH | Oxidative stabilisation of sterols and sterol esters |
JP6124664B2 (en) * | 2013-04-19 | 2017-05-10 | 株式会社Adeka | Plastic oil composition |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5998396A (en) * | 1996-11-05 | 1999-12-07 | Riken Vitamin Co., Ltd. | Oil solubilized solutions and foods containing phytosterols and process for their production |
EP1082026A1 (en) * | 1998-06-05 | 2001-03-14 | Forbes Medi-Tech Inc. | Compositions comprising phytosterol and/or phytostanol having enhenced solubility and dispersa |
AU5612199A (en) * | 1998-09-10 | 2000-04-03 | Forbes Medi-Tech Inc. | Compositions comprising one or more phytosterols, phytostanols or mixtures of both and one or more alpha, beta, delta, or gamma tocotrienols or derivatives thereof and use of the compositions in treating or preventing cardiovascular disease, its underlying conditions and other |
WO2000041491A2 (en) * | 1999-01-15 | 2000-07-20 | Nutrahealth Ltd (Uk) | Modified food products and beverages, and additives for food and beverages |
US20020012710A1 (en) * | 1999-11-29 | 2002-01-31 | Rimonest Ltd. | Pomegranate products useful in improving health and methods of use thereof |
NZ519268A (en) * | 1999-12-15 | 2004-12-24 | Mcneil Ppc Inc | Cholesterol lowering comestibles comprising policosanol (predominately octasanol) and sterol |
GB0026018D0 (en) * | 2000-10-24 | 2000-12-13 | Novartis Nutrition Ag | New composition |
CA2430878A1 (en) * | 2001-01-29 | 2002-08-08 | Christopher J. Berry | Anticholesterolemic edible oil |
AU2002252387A1 (en) * | 2001-03-14 | 2002-09-24 | Lipogenics, Inc. | Novel anti-inflammatory compositions and methods of use |
FI20012553A0 (en) * | 2001-12-21 | 2001-12-21 | Raisio Benecol Oy | Edible compositions |
-
2005
- 2005-03-16 EP EP05716179A patent/EP1742545A1/en not_active Withdrawn
- 2005-03-16 AU AU2005232369A patent/AU2005232369A1/en not_active Abandoned
- 2005-03-16 WO PCT/EP2005/002878 patent/WO2005099484A1/en not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO2005099484A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU2005232369A1 (en) | 2005-10-27 |
WO2005099484A1 (en) | 2005-10-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2006212485B2 (en) | Food products comprising hydrolysed milk solids with improved taste | |
AU2002325486B2 (en) | Composition for lowering blood cholesterol | |
US6423363B1 (en) | Aqueous dispersion | |
US9144545B2 (en) | Sterol ester powder | |
JP2012191944A (en) | Food product with masked bitterness, acidity and/or astringency | |
EP1653814A1 (en) | Plant sterol-containing food, and method for preparing the same | |
US20050281932A1 (en) | Frozen confection | |
AU2003249894B2 (en) | Phytosterols or phytostanols and their use in food products | |
JP2013518565A (en) | Beverage | |
US11806352B2 (en) | Theobromine for increasing HDL-cholesterol | |
US20070141123A1 (en) | Emulsions comprising non-esterified phytosterols in the aqueous phase | |
US20060188635A1 (en) | Food product comprising phytosterols | |
WO2005099484A1 (en) | Water continuous product comprising sterol or stanolester and a tocopherol | |
MXPA05004461A (en) | Water in oil emulsion comprising sterolesters. | |
AU2007222696B2 (en) | Sterol esters having short-chained fatty acids | |
AU2007211935A1 (en) | Phytosterols or phytostanols and their use in food products |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20060905 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: MELLEMA, MICHEL Inventor name: HEETVELDE, INGEBORG SONJA VIKTOR |
|
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20071001 |