JP3597478B2 - Tocopherol preparation with suppressed flavor deterioration and food and beverage containing the same - Google Patents
Tocopherol preparation with suppressed flavor deterioration and food and beverage containing the same Download PDFInfo
- Publication number
- JP3597478B2 JP3597478B2 JP2001042298A JP2001042298A JP3597478B2 JP 3597478 B2 JP3597478 B2 JP 3597478B2 JP 2001042298 A JP2001042298 A JP 2001042298A JP 2001042298 A JP2001042298 A JP 2001042298A JP 3597478 B2 JP3597478 B2 JP 3597478B2
- Authority
- JP
- Japan
- Prior art keywords
- tocopherol
- oil
- food
- mass
- preparation
- 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.)
- Expired - Lifetime
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- 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 description 121
- 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 description 111
- 229930003799 tocopherol Natural products 0.000 title claims description 104
- 239000011732 tocopherol Substances 0.000 title claims description 104
- 235000010384 tocopherol Nutrition 0.000 title claims description 104
- 229960001295 tocopherol Drugs 0.000 title claims description 104
- 238000002360 preparation method Methods 0.000 title claims description 67
- 239000000796 flavoring agent Substances 0.000 title claims description 34
- 235000019634 flavors Nutrition 0.000 title claims description 34
- 235000013305 food Nutrition 0.000 title claims description 32
- 230000006866 deterioration Effects 0.000 title claims description 23
- 235000013361 beverage Nutrition 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 claims description 34
- 239000000839 emulsion Substances 0.000 claims description 24
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 22
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 21
- 235000010445 lecithin Nutrition 0.000 claims description 19
- 239000000787 lecithin Substances 0.000 claims description 19
- 229930182558 Sterol Natural products 0.000 claims description 14
- 235000003702 sterols Nutrition 0.000 claims description 14
- 150000003432 sterols Chemical class 0.000 claims description 14
- -1 glycerin fatty acid ester Chemical class 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229960000984 tocofersolan Drugs 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 229940087168 alpha tocopherol Drugs 0.000 claims description 8
- 235000004835 α-tocopherol Nutrition 0.000 claims description 8
- 239000002076 α-tocopherol Substances 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 235000011187 glycerol Nutrition 0.000 claims description 6
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 235000009508 confectionery Nutrition 0.000 claims description 3
- 235000021185 dessert Nutrition 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 description 31
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- 238000011156 evaluation Methods 0.000 description 21
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 17
- 229940067606 lecithin Drugs 0.000 description 17
- 238000003860 storage Methods 0.000 description 17
- 244000068988 Glycine max Species 0.000 description 15
- 235000010469 Glycine max Nutrition 0.000 description 15
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 235000002378 plant sterols Nutrition 0.000 description 9
- 239000003925 fat Substances 0.000 description 8
- 235000019197 fats Nutrition 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 235000012424 soybean oil Nutrition 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 235000015110 jellies Nutrition 0.000 description 6
- 235000013310 margarine Nutrition 0.000 description 6
- 239000003264 margarine Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 235000020124 milk-based beverage Nutrition 0.000 description 6
- 229960002446 octanoic acid Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 5
- 239000008274 jelly Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 230000001953 sensory effect Effects 0.000 description 5
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229930003427 Vitamin E Natural products 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 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 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229940046009 vitamin E Drugs 0.000 description 3
- 235000019165 vitamin E Nutrition 0.000 description 3
- 239000011709 vitamin E Substances 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002411 adverse Effects 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
- 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
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229940057917 medium chain triglycerides Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000011496 sports drink Nutrition 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-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
- 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
- 241000195940 Bryophyta Species 0.000 description 1
- 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 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 1
- 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 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000299461 Theobroma cacao 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
- 239000003513 alkali Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940076810 beta sitosterol Drugs 0.000 description 1
- 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 1
- 230000017531 blood circulation 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
- 235000000431 campesterol Nutrition 0.000 description 1
- 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 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000019261 food antioxidant Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 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 1
- 229950005143 sitosterol Drugs 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
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 239000000243 solution 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
- 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
- 239000003760 tallow Substances 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
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Landscapes
- Confectionery (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Jellies, Jams, And Syrups (AREA)
- Medicinal Preparation (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Edible Oils And Fats (AREA)
- Non-Alcoholic Beverages (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【0001】
【発明の属する技術分野】
本発明は、トコフェロール製剤、詳しくは特定量の中鎖脂肪酸トリグリセライドを含有することにより経時安定性に優れ、風味劣化が抑制されたトコフェロール製剤に関し、更には、該トコフェロール製剤を配合してなる飲食物に関する。
【0002】
【従来の技術】
トコフェロールは、酸化防止作用、血管拡張作用、血行促進作用等の多くの優れた生理作用を有することから、多くの分野で幅広く使用されており、食品分野においても広範囲にわたり使用されている。例えば、中鎖脂肪酸トリグリセライドとビタミンEを含有した栄養食品組成物(特開昭57−47446号公報)、ビタミンEを配合したスポーツ用ドリンク組成物(特開昭59−210870号公報)、pHが3.0以下で乳化安定性、水分散性の良好なビタミンE含有食品用酸化防止剤(特公平4−3190号公報)等が知られている。
【0003】
【発明が解決しようとする課題】
しかしながら、トコフェロールは、保存中に臭い、味が劣化しやすい。かかる劣化トコフェロールを原料として用いた飲食物は、その含有量が微量であっても風味の劣化がさけられない。
【0004】
したがって、本発明は、経時安定性に優れ、臭いや味等の風味の劣化が抑制されたトコフェロール製剤を提供することを目的とする。
本発明はまた、かかるトコフェロール製剤含有する飲食物を提供することを目的とする。
【0005】
【課題を解決するための手段】
本発明者らは、上記課題を解決すべく鋭意研究した結果、特定量の中鎖脂肪酸トリグリセライドをトコフェロールとともに配合した製剤であれば、従来のトコフェロール製剤に比べて経時安定性に優れ、臭いや味等の風味の劣化が抑制されることを見出し、本発明を完成した。
【0006】
すなわち、本発明は、トコフェロールを52質量%以上、中鎖脂肪酸トリグリセライドを0.2質量%以上含有することを特徴とする風味劣化が抑制されたトコフェロール製剤を提供するものである。かかる製剤中のトコフェロールは、酸化劣化が抑制されるため、経時安定性に優れ、味や風味の劣化が極めて少ない。このため、これを原料として用いれば、中性食品、酸性食品、乳化食品等いずれをも問わず、長期間保存しても風味劣化が極めて少ない飲食物が得られる。本発明はまた、かかる風味劣化が抑制されたトコフェロール製剤を配合してなる飲食物を提供するものである。
【0007】
【発明の実施の形態】
本発明で使用するトコフェロールの製造方法に特に制限はないが、例えば以下の方法により製造することができる。すなわち、大豆油、菜種油、綿実油、サフラワー油、ヒマワリ油、ヤシ油、パーム油、パーム核油等植物性油脂の脱臭工程で副生する脱臭スカム、脱臭スラッジ、ホットウェル油滓等を原料とし、これから陰イオン交換樹脂あるいは分子蒸留又はこれらを組み合わせて製造することができる。トコフェロールの種類としては、例えばα体、β体、γ体、δ体若しくはそれらの混合体、dl−α−トコフェロール、又は濃縮トコフェロール等が挙げられる。このうち、α−トコフェロールを含むことにより、生体内酸化防止機能が高くなるため好ましい。かかる効果は、トコフェロール中のαトコフェロール含有量が10質量%以上、特に20質量%以上である場合に顕著である。
また、ビタミンA、D、K等のトコフェロール以外の脂溶性ビタミンは、風味等に悪影響を及ぼさないため、添加しても差し支えない。
【0008】
本発明で使用する中鎖脂肪酸トリグリセリドは、一般にMCT(Medium Chain Triglycerides)と称されるもので、ヤシ油分解脂肪酸等の炭素数が6〜12、好ましくは8〜10の飽和脂肪酸から構成される単酸基または混酸基トリグリセリドである。このうち、例えばカプリル酸(C8)/カプリン酸(C10)=60〜75/40〜25(重量比)のトリグリセリドが特に好ましい。かかる中鎖脂肪酸トリグリセライドは、前記中鎖脂肪酸とグリセリンとを常法によりエステル化反応せしめて製造できるが、市販品の利用が至便である。
【0009】
一般に、中鎖脂肪酸トリグリセライドは、これを20重量%以上含む油脂として調製されることが好ましい。中鎖脂肪酸トリグリセライド以外の油脂としては、例えば大豆油、菜種油、綿実油、コーン油、サフラワー油、ヒマワリ油、ごま油、オリーブ油、パーム油、パーム核油、カカオ油、やし油、ラード、牛脂、魚油、シソ油、アマニ油、桐油、ひまし油等の液状油および固形脂、これらの配合油、水素添加油、分別油、エステル交換油等の加工油脂が使用できる。このうち、液状油が望ましい。かかる油脂中の中鎖脂肪酸トリグリセライド含量は35重量%以上が望ましく、中鎖脂肪酸トリグリセライド含量が増えるにしたがい、経時安定性、風味が良好となる。
【0010】
本発明のトコフェロール製剤には、さらにステロール又はレシチンの1種又は2種以上を添加することが好ましい。かかるトコフェロール製剤又はこれを含有する飲食物を摂食することにより、血中コレステロール等の血中脂質の調節、低減が強化される。
本発明で使用するステロールとしては、フィトステロールが好ましい。フィトステロールとは、生物界に広く分布するステロール中の植物ステロールをさす。植物ステロールは、β−シトステロール、スチグマステロール、カンペステロール、ブラシカステロール等の混合物であるが、エステルの状態で存在しているものもある。該植物ステロールは、例えば植物油の脱臭工程で得られる留出物を原料として抽出、精製することにより得ることができる。すなわち、留出物をアルカリを用いてけん化分解した後、遠心分離して得た沈殿を、硫酸メタノール等でメチルエステル化した後、再結晶化することにより、得ることができる。なお、留出物をメタノール、エタノール等の溶剤に濃厚に溶かし、冷却して析出する結晶を濾取した後、再結晶化したものは、フィトステロールとそのエステルの混合物として得られるが、本発明においては、ステロールとして、かかるフィトステロールのエステル化物を用いてもよい。
【0011】
本発明で使用し得るレシチンは、公知のペースト状レシチン、又は該ペースト状レシチンを原料として得られる粉末状、顆粒状もしくは塊状の高純度レシチン等が挙げられる。かかるペースト状レシチンは、通常、大豆、菜種、ひまわり、サフラワー、亜麻仁等の油糧種子から油脂を製造する際の脱ガム工程で得られる油滓を濾過、乾燥したものであり、一般的に30〜40重量%程度の脂質を含む。一方、高純度レシチンは、通常、前記ペースト状レシチンを原料とし、アルコール、アセトン、プロパノール、シクロヘキサン、ベンゼン、クロロホルム等の溶剤を使用して分別、濃縮、乾燥等の処理によりレシチン分を精製したものである。また、ホスホリパーゼを使用し酵素分解されたレシチンを使用することもできる。
【0012】
本発明の製剤は、前述のような諸原料を用いてなるものであり、トコフェロールを50質量%以上、好ましくは70質量%以上、より好ましくは80質量%以上含有する。50質量%未満では、本発明の酸化防止効果が発揮できず、該効果を得ようとするとすれば、トコフェロール製剤を多量に使用せざるを得なくなり、飲食物の必須成分含量低下などの悪影響を与える。特に、トコフェロール中のαトコフェロール含量が10重量%以下の場合、生体内での酸化防止機能が期待し難い。また、トコフェロール製剤中の中鎖脂肪酸トリグリセライド含有量は、0.2質量%以上であることが必要であり、0.5質量%以上であることが好ましく、1.0質量%以上であることがより好ましい。0.2質量%未満では、トコフェロールの風味劣化を十分に防止することができず、かかるトコフェロール製剤を用いた飲食物は、臭いや味等の風味が悪い。さらに、トコフェロール製剤中の、トコフェロールと中鎖脂肪酸トリグリセライドの比率(質量比)は、99.8:0.2〜75:25であることが好ましく、99:1〜75:25であることが特に好ましい。99.8:0.2〜75:25であれば、保存中のトコフェロールの風味劣化を有効に防止することができ、かかるトコフェロール製剤を用いた飲食品は、風味劣化がほとんどない。
【0013】
トコフェロール製剤中のステロール含有量は、0.1〜15質量%が好ましく、1〜15質量%がより好ましく、5〜15質量%が特に好ましい。また、トコフェロール製剤中のレシチン含有量は、0.1〜30質量%が好ましく、1〜25質量%がより好ましく、5〜25質量%が特に好ましい。
【0014】
本発明の風味劣化が抑制されたトコフェロール製剤は、例えば以下に述べる方法で製造できるが、これに限定されるものではない。すなわち、中鎖脂肪酸トリグリセライドを20重量%以上含む油脂、トコフェロールを同時に攪拌、混合して均一な液状物となす等の方法により本発明の製剤を得ることができる。なお、上記操作はすべて室温〜60℃程度の加温で行うことができ、攪拌処理はプロペラ、ホモミキサー等の通常の攪拌機を用いることができ、例えば回転数:2,000〜4,000rpmで0.5〜1.5時間程度行えばよい。また、ステロール、レシチンを添加する場合は、例えば中鎖脂肪酸トリグリセライドを20重量%以上含む油脂とレシチンを混合、撹拌して均一な液状物とした後、ステロールを加えて撹拌し、均一な液状物とした後、トコフェロールを混合、撹拌することにより得ることができる。上記操作はすべて室温〜60℃程度の加温で行うことができ、攪拌処理はプロペラ、ホモミキサー等の通常の攪拌機を用いることができ、例えば回転数:2,000〜4,000rpmで0.5〜3時間程度行えばよい。
【0015】
かくして得られるトコフェロール製剤は、均一な液状で流動性に富み、結晶析出や白濁を呈することなく安定性の高いものである。
また、該トコフェロール製剤は、乳化状にすることにより水系への添加が可能となり、幅広い分野での使用が可能となる。乳化状にする際に、水相として水、多価アルコール等を用いることができ、さらに乳化剤を用いることができる。本発明で使用する多価アルコールは、グリセリン、プロピレングリコール、糖アルコール等の食品に使用してもさしつかえのないものであれば特に制限はない。乳化組成物中の多価アルコールの含有量は特に規定されるものではないが、保存安定性、水への分散性から1〜90質量%、特に30〜70質量%が好ましい。
【0016】
本発明で使用する乳化剤は、グリセリン脂肪酸エステル、ソルビタン脂肪酸エステル、ショ糖脂肪酸エステルの1種または2種以上である。グリセリン脂肪酸エステルはモノ、ジ、ポリグリセリン脂肪酸エステルの使用できる。これらのHLBは1〜20、特に3〜12が好ましく、目的の乳化の形態によって用いる乳化剤のHLBを決定することができる。乳化組成物は、例えば以下に述べる方法で製造できるが、これに限定されるものではない。水、多価アルコール中に乳化剤を加え、加温溶解し、プロペラ攪拌によって均質化して水相を調整する。均一溶解した水相に該トコフェロール製剤を加えホモミキサーにより均質乳化をする。上記操作は全て40℃ないし75℃程度の加温で行うことができ、攪拌処理はプロペラ、ホモミキサー、ブレンダー等の通常の攪拌機を、乳化はホモミキサー、高圧ホモジナイザー、マイクロフルイダイザー等を用いることができる。油溶性乳化剤を用いる場合は、乳化剤をトコフェロール製剤に加えた後、水相と混合、均質乳化してもよい。
かくして得られる乳化状トコフェロール製剤は、水や調味液等に容易に分散し、トコフェロール製剤に配合されているステロールの結晶の析出も見られない。油分や水分は分離することなく安定で、風味も良好であり、飲食物への配合によっても、経時安定性が良く、風味が良好である。
【0017】
本発明の風味劣化が抑制されたトコフェロール製剤の形態は、常温でペースト状であることが好ましい。また、グリセリン脂肪酸エステル、ソルビタン脂肪酸エステル及びショ糖脂肪酸エステルからなる群より選ばれる1種または2種以上と、水と、多価アルコールとを含有する乳化状であることが好ましい。
【0018】
なおステロール又はレシチンを含まない製剤、ステロール又はレシチンを含む製剤の適用範囲は特に限定されないが、後者は特に血中脂質低下効果を期待する製品に対してより効果的である。
【0019】
本発明の飲食物は、かかるトコフェロール製剤を配合したものである。飲食物としては、かかるトコフェロール製剤を均一に分散させることができるものであれば特に制限はないが、飲料、デザート菓子、加工油脂製品が好ましい。飲料は、酸性飲料、中性飲料のいずれでもよく、酸性飲料はpH3以下、3以上のいずれでもよく、3以上が特に好ましい。飲料としては、例えば加工乳飲料、清涼飲料水、スポーツ飲料等が挙げられる。デザート菓子としては、例えばゼリー、ムース、ババロア、ケーキ等が挙げられる。加工油脂製品としては、例えばマーガリン、ファットスプレッド、クリーム等が挙げられる。かかる飲食物は、飲食物に通常用いられる原料及びトコフェロール製剤を用い、該飲食物を製造する場合の常法に従って製造することができる。なお、これらの商品をショーケース等に陳列したときに、光による風味劣化を抑制するため、トコフェロールが添加される場合がある。このとき、トコフェロールとして本発明のトコフェロール製剤を用いれば、商品の、光による風味劣化のみならず、トコフェロールの劣化による風味劣化も十分に抑制することができる。
【0020】
【実施例】
以下に実施例を挙げて本発明をより具体的に説明するが、本発明はそれらによって限定されるものではない。
【0021】
製造例1
カプリル酸/カプリン酸=75/25(重量比)の中鎖脂肪酸トリグリセライド(商品名:ODO、日清製油(株)製)3質量%、大豆トコフェロール(トコフェロール含量95%、αトコフェロール95%以上、日清製油(株)製)97質量%を混合し、プロペラを用い、3000rpm、40℃の条件で十分に成分が均一化するまで攪拌、冷却し、本発明のトコフェロール製剤を得た。本製剤は、褐色で粘稠性のある均一な液状物であった。
【0022】
製造例2
カプリル酸/カプリン酸=75/25(重量比)の中鎖脂肪酸トリグリセライド(商品名:ODO、日清製油(株)製)1.2質量%、大豆油(商品名:大豆白絞油、日清製油(株)製)1.8質量%、大豆トコフェロール(トコフェロール含量95%、αトコフェロール95%以上、日清製油(株)製)97質量%を混合し、プロペラを用い、3000rpm、40℃の条件で十分に成分が均一化するまで攪拌、冷却し、本発明のトコフェロール製剤を得た。本製剤は、褐色で粘稠性のある均一な液状物であった。
【0023】
製造例3
カプリル酸/カプリン酸=75/25(重量比)の中鎖脂肪酸トリグリセライド(商品名:ODO、日清製油(株)製)4質量%、大豆油(商品名:大豆白絞油、日清製油(株)製)6質量%、大豆トコフェロール(トコフェロール含量95%、αトコフェロール95%以上、日清製油(株)製)50質量%、菜種トコフェロール(商品名:トコフェロール100R、日清製油(株)製)40質量%を混合し、プロペラを用い、3000rpm、室温の条件で十分に成分が均一化するまで攪拌、冷却し、本発明のトコフェロール製剤を得た。本製剤は、褐色で粘稠性のある均一な液状物であった。
【0024】
製造例4
カプリル酸/カプリン酸=75/25(重量比)の中鎖脂肪酸トリグリセライド(商品名:ODO、日清製油(株)製)20質量%、大豆油(商品名:大豆白絞油、日清製油(株)製)10質量%、植物ステロール(商品名:Phytosterol、ADM製)10質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌する。その後、大豆トコフェロール(商品名:トコフェロール98、日清製油(株)製)60質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌、冷却し、本発明のトコフェロール製剤を得た。本製剤は、褐色で粘稠性のある均一な液状物であった。
【0025】
製造例5
カプリル酸/カプリン酸=60/40(重量比)の中鎖脂肪酸トリグリセライド(商品名:ODO、日清製油(株)製)18質量%、植物ステロール(商品名:Phytosterol、ADM製)10質量%、レシチン(商品名:ベイシスLP−20、日清製油(株)製)20質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌する。その後、大豆トコフェロール(商品名:トコフェロール98、日清製油(株)製)52質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌、冷却し、本発明のトコフェロール製剤を得た。本製剤は、褐色で粘稠性のある均一な液状物であった。
【0026】
製造比較例1
大豆油(商品名:大豆白絞油、日清製油(株)製)3質量%、大豆トコフェロール(トコフェロール含量95%、αトコフェロール95%以上、日清製油(株)製)97質量%を混合し、プロペラを用い、3000rpm、40℃の条件で十分に成分が均一化するまで攪拌、冷却し、トコフェロール製剤を得た。該製剤は、褐色で粘稠性のある均一な液状物であった。
【0027】
製造比較例2
大豆油(商品名:大豆白絞油、日清製油(株)製)30質量%、植物ステロール(商品名:Phytosterol、ADM製)10質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌する。その後、大豆トコフェロール(商品名:トコフェロール98、日清製油(株)製)60質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌、冷却し、トコフェロール製剤を得た。冷却後数時間で植物ステロールの結晶が発生した。
【0028】
製造比較例3
大豆油(商品名:大豆白絞油、日清製油(株)製)18質量%、植物ステロール(商品名:Phytosterol、ADM製)10質量%、レシチン(商品名:ベイシスLP−20、日清製油(株)製)20質量%を混合し、ホモミキサーを用い、4000〜5000rpm、60℃の条件で十分に成分が均一化するまで攪拌した。その後、大豆トコフェロール(商品名:トコフェロール98、日清製油(株)製)52質量%を混合し、プロペラを用い、4000rpm、60℃の条件で十分に成分が均一化するまで攪拌、冷却し、トコフェロール製剤を得た。室温保存約1週間後に植物ステロールの結晶が発生した。
【0029】
製造例1〜5及び製造比較例1〜3の処方配合は表1の通りである。製造比較例2、3は製造後もしくは、保存中にステロールの結晶析出が見られたため、以降の評価の実施は行わなかった。なお、表1中のステロールの結晶析出状態において、◎は極めて良好、○は良好だが経時的にわずかずつ濁っていく、△はしばらくすると析出する、×は製造直後に析出する、を示す。
【0030】
【表1】
【0031】
評価1
製造例1〜5、製造比較例1の各トコフェロール製剤を室温で保管し、1週間及び1か月保存後の風味を、水溶液状態にして評価した。トコフェロール製剤は水には完全に溶解しないが、水に呈味成分が移行するため、官能評価が可能と判断し、1%水溶液を調製し、官能評価をパネル10名を用いて、以下の評価基準で評価を行った(以下の官能評価において同じ)。結果を表2に示す。
(評価基準)
◎:良好である。
○:やや良好である。
△:やや悪い。
×:悪い。
【0032】
【表2】
【0033】
製造比較例1のトコフェロール製剤は、保存開始1週間で風味がやや悪くなり、1月で悪化した。これに対し、製造例1〜5のトコフェロール製剤は、1月保存品が製造比較例1のトコフェロール製剤の1週間保存品と同等又はそれ以上であり、本発明の効果が確認された。特に、製造例1のトコフェロール製剤は、1月保存した後も風味が極めて良好であった。
【0034】
評価2
製造例1〜5及び製造比較例1のトコフェロール製剤を使用し、乳化物を調製した。各トコフェロール製剤使用乳化物を室温で保管し、1週間、1か月保存後の風味を、1%水溶液状態にし官能評価をパネル10名で5点評価で行った。乳化物の配合は表3の通りである。また、官能評価結果を表4に示す。
【0035】
【表3】
【0036】
(乳化物調製方法)
水相を均一に混合した後、水相、油相ともに60〜65℃に加温した。加温状態で水相中に油相を滴下し、予備乳化を行った。予備乳化後高圧ホモジナイザーで乳化し、乳化物を得た。
【0037】
【表4】
【0038】
製造比較例1のトコフェロール製剤を用いた乳化物は、保存1週間で臭い、味がやや悪くなり、1月で味、臭い、外観とも悪化した。これに対し、製造例1〜5のトコフェロール製剤を用いた乳化物は、1月保存品が製造比較例1のトコフェロール製剤を用いた乳化物の1週間保存品と同等又はそれ以上であり、本発明の効果が確認された。特に、製造例1のトコフェロール製剤を用いた乳化物は、1月保存した後も風味、外観が極めて良好であった。
【0039】
評価3<飲料>
評価2で得られた乳化物は以降乳化物1〜5、乳化比較例1とする。
評価2で調製した乳化物を用い、表5の配合で常法に従い飲料モデルを調製した。調製した飲料を1週間冷蔵保管した後、官能評価をパネル10名で5点評価で行った。結果を表6に示す。
【0040】
【表5】
【0041】
【表6】
【0042】
乳化物1〜5を用いた飲料は、いずれも乳化比較例1を用いた飲料よりも臭い、味、外観が優れていた。
【0043】
評価4<酸性乳飲料>
評価2で調製した乳化物を用いて、表7の配合で常法に従い酸性乳飲料を調製した。該酸性乳飲料の評価結果を表8に示す。
【0044】
【表7】
【0045】
【表8】
【0046】
乳化物1〜5を用いた酸性乳飲料は、いずれも乳化比較例1を用いた酸性乳飲料よりも臭い、味、外観が優れていた。
【0047】
評価5<ゼリー>
評価2で調製した乳化物を用いて、表9の配合で常法に従いゼリーを調製した。作成したゼリーの評価結果を表10に示す。
【0048】
【表9】
【0049】
【表10】
【0050】
乳化物1〜5を用いたゼリーは、いずれも乳化比較例1を用いたゼリーよりも臭い、味、外観が優れていた。
【0051】
評価6<マーガリン>
製造例1〜5及び製造比較例1のトコフェロール製剤を用いて、表11の配合で常法に従いマーガリンを調製した。調製したマーガリンを冷蔵で1月保存し、保存開始前及び保存終了後の風味を評価した。評価結果を表12に示す。
【0052】
【表11】
【0053】
【表12】
【0054】
製造例1〜5のトコフェロール製剤を用いたマーガリンは、製造比較例1のトコフェロール製剤を用いたマーガリンに比べて、風味が優れていた。
【0055】
【発明の効果】
本発明のトコフェロール製剤は、従来のトコフェロール製剤に比べて保存中の風味劣化が非常に抑制されたものである。したがって、該トコフェロール製剤を配合した飲食物の風味劣化も同様に抑制することができる。
さらに、ステロール、レシチンを配合すると、血中脂質の低減等にも有効である。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a tocopherol preparation, in particular, a tocopherol preparation which is excellent in stability over time by containing a specific amount of a medium-chain fatty acid triglyceride and in which flavor deterioration is suppressed, and furthermore, a food and drink comprising the tocopherol preparation About.
[0002]
[Prior art]
Tocopherol has many excellent physiological actions such as an antioxidant action, a vasodilatory action, and a blood circulation promoting action, and thus is widely used in many fields and widely used in the food field. For example, a nutritional food composition containing medium-chain fatty acid triglyceride and vitamin E (JP-A-57-47446), a sports drink composition containing vitamin E (JP-A-59-210870), Vitamin E-containing food antioxidants having a good emulsification stability and water dispersibility of 3.0 or less (Japanese Patent Publication No. 4-3190) are known.
[0003]
[Problems to be solved by the invention]
However, tocopherol tends to smell and deteriorate in taste during storage. In foods and drinks using such degraded tocopherol as a raw material, even if the content is very small, deterioration in flavor is not avoided.
[0004]
Accordingly, an object of the present invention is to provide a tocopherol preparation which is excellent in stability over time and in which deterioration of flavor such as odor and taste is suppressed.
Another object of the present invention is to provide a food or drink containing such a tocopherol preparation.
[0005]
[Means for Solving the Problems]
The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, a formulation containing a specific amount of medium-chain fatty acid triglyceride together with tocopherol has excellent stability over time as compared with a conventional tocopherol formulation, and has an odor and taste. It has been found that the deterioration of the flavor such as the above is suppressed, and the present invention has been completed.
[0006]
That is, the present invention provides a tocopherol preparation containing at least 52 % by mass of tocopherol and at least 0.2% by mass of medium-chain fatty acid triglyceride and having suppressed flavor deterioration. Since tocopherol in such a preparation is suppressed from oxidative deterioration, it is excellent in stability over time and deterioration of taste and flavor is extremely small. For this reason, if this is used as a raw material, foods and drinks with extremely little deterioration in flavor even after long-term storage can be obtained irrespective of neutral foods, acidic foods, emulsified foods and the like. The present invention also provides a food or drink comprising the tocopherol preparation in which such flavor deterioration is suppressed.
[0007]
BEST MODE FOR CARRYING OUT THE INVENTION
The method for producing tocopherol used in the present invention is not particularly limited. For example, it can be produced by the following method. That is, as a raw material, deodorized scum, deodorized sludge, hot well soap, and the like, which are by-produced in the deodorization step of vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, safflower oil, sunflower oil, coconut oil, palm oil, and palm kernel oil. And an anion exchange resin or molecular distillation or a combination thereof. Examples of the type of tocopherol include α-form, β-form, γ-form, δ-form and mixtures thereof, dl-α-tocopherol, and concentrated tocopherol. Among them, it is preferable to include α-tocopherol because the function of preventing in vivo oxidation is enhanced. Such an effect is remarkable when the α-tocopherol content in tocopherol is 10% by mass or more, particularly 20% by mass or more.
Fat-soluble vitamins other than tocopherol, such as vitamins A, D, and K, do not adversely affect the flavor and the like, and may be added.
[0008]
The medium-chain fatty acid triglyceride used in the present invention is generally called MCT (Medium Chain Triglycerides), and is composed of a saturated fatty acid having 6 to 12, preferably 8 to 10 carbon atoms, such as coconut oil-decomposed fatty acid. It is a monoacid group or mixed acid group triglyceride. Among these, for example, triglyceride of caprylic acid (C8) / capric acid (C10) = 60 to 75/40 to 25 (weight ratio) is particularly preferable. Such a medium chain fatty acid triglyceride can be produced by subjecting the medium chain fatty acid and glycerin to an esterification reaction by a conventional method, but a commercially available product is conveniently used.
[0009]
Generally, the medium-chain fatty acid triglyceride is preferably prepared as an oil or fat containing 20% by weight or more. Examples of fats and oils other than medium-chain fatty acid triglycerides include, for example, soybean oil, rapeseed oil, cottonseed oil, corn oil, safflower oil, sunflower oil, sesame oil, olive oil, palm oil, palm kernel oil, cocoa oil, coconut oil, lard, tallow, Liquid oils and solid fats such as fish oil, perilla oil, linseed oil, tung oil, castor oil, etc., and processed oils such as blended oils, hydrogenated oils, fractionated oils, and transesterified oils can be used. Of these, liquid oil is desirable. The content of the medium-chain fatty acid triglyceride in such fats and oils is desirably 35% by weight or more. As the content of the medium-chain fatty acid triglyceride increases, the stability over time and the flavor become better.
[0010]
It is preferable to add one or more sterols or lecithins to the tocopherol preparation of the present invention. By eating such a tocopherol preparation or a food or drink containing the same, regulation and reduction of blood lipids such as blood cholesterol are enhanced.
Phytosterol is preferred as the sterol used in the present invention. Phytosterols refer to plant sterols among sterols widely distributed in the living world. The plant sterol is a mixture of β-sitosterol, stigmasterol, campesterol, brassicasterol and the like, but some are present in an ester state. The plant sterol can be obtained, for example, by extracting and purifying a distillate obtained in a step of deodorizing vegetable oil as a raw material. That is, the distillate can be obtained by saponifying and decomposing a distillate using an alkali, and then subjecting the precipitate obtained by centrifugation to methyl esterification with methanol such as sulfuric acid and then recrystallization. The distillate was dissolved in a solvent such as methanol or ethanol in a concentrated manner, and after cooling, the precipitated crystals were collected by filtration and then recrystallized to obtain a mixture of phytosterol and its ester. May use such an esterified product of phytosterol as a sterol.
[0011]
Examples of the lecithin that can be used in the present invention include known paste-like lecithin, or powdery, granular or massive high-purity lecithin obtained from the paste-like lecithin as a raw material. Such a paste-like lecithin is usually obtained by filtering and drying a soapstock obtained in a degumming step in producing an oil or fat from oil seeds such as soybeans, rapeseed, sunflower, safflower, and linseed, and is generally used. It contains about 30 to 40% by weight of lipid. On the other hand, high-purity lecithin is usually obtained by using the above-mentioned pasty lecithin as a raw material, and purifying the lecithin component by a treatment such as separation, concentration, and drying using a solvent such as alcohol, acetone, propanol, cyclohexane, benzene, or chloroform. It is. Lecithin that has been enzymatically degraded using phospholipase can also be used.
[0012]
The preparation of the present invention is prepared using the above-mentioned various raw materials, and contains 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more of tocopherol. If the amount is less than 50% by mass, the antioxidant effect of the present invention cannot be exerted. If the effect is to be obtained, a large amount of a tocopherol preparation must be used, and adverse effects such as a decrease in the content of essential components of food and drink cannot be avoided. give. In particular, when the α-tocopherol content in tocopherol is 10% by weight or less, it is difficult to expect an antioxidant function in vivo. Further, the content of the medium-chain fatty acid triglyceride in the tocopherol preparation needs to be 0.2% by mass or more, preferably 0.5% by mass or more, and more preferably 1.0% by mass or more. More preferred. If the amount is less than 0.2% by mass, the deterioration of the flavor of tocopherol cannot be sufficiently prevented, and the food and drink using such a tocopherol preparation have poor flavor such as smell and taste. Furthermore, the ratio (mass ratio) of tocopherol to medium-chain fatty acid triglyceride in the tocopherol preparation is preferably 99.8: 0.2 to 75:25, particularly preferably 99: 1 to 75:25. preferable. When the ratio is 99.8: 0.2 to 75:25, the deterioration of the flavor of tocopherol during storage can be effectively prevented, and the food or drink using the tocopherol preparation hardly deteriorates in flavor.
[0013]
The sterol content in the tocopherol preparation is preferably 0.1 to 15% by mass, more preferably 1 to 15% by mass, and particularly preferably 5 to 15% by mass. Further, the lecithin content in the tocopherol preparation is preferably 0.1 to 30% by mass, more preferably 1 to 25% by mass, and particularly preferably 5 to 25% by mass.
[0014]
The tocopherol preparation of the present invention in which flavor deterioration is suppressed can be produced by, for example, the following method, but is not limited thereto. That is, the preparation of the present invention can be obtained by a method of simultaneously stirring and mixing oils and fats containing 20% by weight or more of medium-chain fatty acid triglyceride and tocopherol to form a uniform liquid. In addition, all the above operations can be performed by heating at room temperature to about 60 ° C., and the stirring process can be performed using a normal stirrer such as a propeller or a homomixer. For example, the rotation speed is 2,000 to 4,000 rpm. It may be performed for about 0.5 to 1.5 hours. When sterol or lecithin is added, for example, a fat and oil containing 20% by weight or more of medium-chain fatty acid triglyceride and lecithin are mixed and stirred to form a uniform liquid, and then sterol is added and stirred to form a uniform liquid. After that, tocopherol can be obtained by mixing and stirring. All of the above operations can be carried out by heating at room temperature to about 60 ° C., and the stirring can be carried out using a conventional stirrer such as a propeller or a homomixer, for example, at a rotational speed of 2,000 to 4,000 rpm. It may be performed for about 5 to 3 hours.
[0015]
The tocopherol preparation thus obtained is a uniform liquid, rich in fluidity, and has high stability without crystal precipitation or cloudiness.
The tocopherol preparation can be added to an aqueous system by emulsifying it, and can be used in a wide range of fields. When emulsified, water, a polyhydric alcohol, or the like can be used as the aqueous phase, and an emulsifier can be used. The polyhydric alcohol used in the present invention is not particularly limited as long as it can be used in foods such as glycerin, propylene glycol and sugar alcohol. The content of the polyhydric alcohol in the emulsion composition is not particularly limited, but is preferably 1 to 90% by mass, particularly preferably 30 to 70% by mass from the viewpoint of storage stability and dispersibility in water.
[0016]
The emulsifier used in the present invention is one or more of glycerin fatty acid ester, sorbitan fatty acid ester and sucrose fatty acid ester. The glycerin fatty acid ester can be a mono-, di-, or polyglycerin fatty acid ester. These HLBs are preferably from 1 to 20, particularly preferably from 3 to 12, and the HLB of the emulsifier to be used can be determined depending on the desired form of emulsification. The emulsion composition can be produced by, for example, the method described below, but is not limited thereto. An emulsifier is added to water and polyhydric alcohol, dissolved by heating, and homogenized by stirring with a propeller to adjust an aqueous phase. The tocopherol preparation is added to the uniformly dissolved aqueous phase, and homogenized with a homomixer. All of the above operations can be performed at a temperature of about 40 ° C. to 75 ° C., and the stirring process is performed using a normal stirrer such as a propeller, a homomixer, and a blender, and the emulsification is performed using a homomixer, a high-pressure homogenizer, a microfluidizer, and the like. Can be. When an oil-soluble emulsifier is used, the emulsifier may be added to the tocopherol preparation, mixed with the aqueous phase, and homogenized.
The emulsified tocopherol preparation thus obtained is easily dispersed in water, a seasoning solution, or the like, and no sterol crystals are precipitated in the tocopherol preparation. The oil and water are stable without separation and have a good flavor. Even when blended in foods and drinks, they have good stability over time and good flavor.
[0017]
The form of the tocopherol preparation of the present invention in which flavor deterioration is suppressed is preferably a paste at room temperature. Further, it is preferably an emulsified form containing one or more selected from the group consisting of glycerin fatty acid ester, sorbitan fatty acid ester and sucrose fatty acid ester, water, and a polyhydric alcohol.
[0018]
The application range of a preparation containing no sterol or lecithin or a preparation containing sterol or lecithin is not particularly limited, but the latter is more effective particularly for a product expected to have a blood lipid lowering effect.
[0019]
The food or drink of the present invention is a mixture of the tocopherol preparation. There is no particular limitation on foods and drinks as long as such a tocopherol preparation can be uniformly dispersed, but drinks, dessert confectionery, and processed fats and oils products are preferred. The beverage may be any of an acidic beverage and a neutral beverage, and the acidic beverage may have a pH of 3 or less, 3 or more, and particularly preferably 3 or more. Examples of the drink include processed milk drink, soft drink, sports drink and the like. Examples of the dessert confectionery include jelly, mousse, bavarois, cake and the like. Examples of the processed oil and fat products include margarine, fat spread, cream and the like. Such foods and drinks can be produced using raw materials and tocopherol preparations usually used for foods and drinks according to the usual method for producing such foods and drinks. Note that when these products are displayed in a showcase or the like, tocopherol may be added in order to suppress flavor deterioration due to light. At this time, if the tocopherol preparation of the present invention is used as the tocopherol, not only the deterioration of the flavor of the product due to light but also the deterioration of the flavor due to the deterioration of the tocopherol can be sufficiently suppressed.
[0020]
【Example】
Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited thereto.
[0021]
Production Example 1
Caprylic acid / capric acid = 75/25 (weight ratio) medium chain fatty acid triglyceride (trade name: ODO, manufactured by Nisshin Oil Co., Ltd.) 3% by mass, soybean tocopherol (tocopherol content 95%, α-tocopherol 95% or more) 97% by mass of Nisshin Oil Co., Ltd.) were mixed, and the mixture was stirred and cooled using a propeller at 3000 rpm and 40 ° C. until the components were sufficiently homogenized to obtain a tocopherol preparation of the present invention. The formulation was a brown, viscous, homogeneous liquid.
[0022]
Production Example 2
Caprylic acid / capric acid = 75/25 (weight ratio) medium chain fatty acid triglyceride (trade name: ODO, manufactured by Nisshin Oil Co., Ltd.) 1.2% by mass, soybean oil (trade name: soybean white drawing oil, Japanese 1.8 mass% of Soybean Oil Co., Ltd.) and 97 mass% of soybean tocopherol (tocopherol content: 95%, α-tocopherol: 95% or more, manufactured by Nisshin Oil Co., Ltd.) are mixed using a propeller at 3000 rpm and 40 ° C. The mixture was stirred and cooled under the conditions described above until the components were sufficiently homogenized to obtain a tocopherol preparation of the present invention. The formulation was a brown, viscous, homogeneous liquid.
[0023]
Production Example 3
Caprylic acid / capric acid = 75/25 (weight ratio) 4% by mass of medium-chain fatty acid triglyceride (trade name: ODO, manufactured by Nisshin Oil Co., Ltd.), soybean oil (trade names: soybean white squeezed oil, Nisshin Oil) 6% by mass, soybean tocopherol (tocopherol content 95%, α-tocopherol 95% or more, manufactured by Nisshin Oil Co., Ltd.) 50% by mass, rapeseed tocopherol (trade name: Tocopherol 100R, Nisshin Oil Co., Ltd.) Was mixed and stirred with a propeller at 3000 rpm and room temperature until the components were sufficiently homogenized to obtain a tocopherol preparation of the present invention. The formulation was a brown, viscous, homogeneous liquid.
[0024]
Production Example 4
Caprylic acid / capric acid = 75/25 (weight ratio), 20% by mass of medium-chain fatty acid triglyceride (trade name: ODO, manufactured by Nisshin Oil Co., Ltd.), soybean oil (trade names: soybean white drawn oil, Nisshin Oil) 10% by mass (manufactured by KK) and 10% by mass of plant sterol (trade name: Physterol, manufactured by ADM) are mixed, and the mixture is stirred using a propeller at 4000 rpm and 60 ° C. until the components are sufficiently homogenized. Thereafter, 60% by mass of soybean tocopherol (trade name: Tocopherol 98, manufactured by Nisshin Oil Co., Ltd.) is mixed, and the mixture is stirred and cooled using a propeller at 4000 rpm and 60 ° C. until the components are sufficiently uniformized. The tocopherol preparation of the present invention was obtained. The formulation was a brown, viscous, homogeneous liquid.
[0025]
Production Example 5
Caprylic acid / capric acid = 60/40 (weight ratio) medium chain fatty acid triglyceride (trade name: ODO, manufactured by Nisshin Oil Co., Ltd.) 18% by mass, plant sterol (trade name: Phytosterol, manufactured by ADM) 10% by mass And 20% by mass of lecithin (trade name: Basis LP-20, manufactured by Nisshin Oil Co., Ltd.), and stirred with a propeller at 4000 rpm and 60 ° C. until the components are sufficiently homogenized. Thereafter, 52% by mass of soybean tocopherol (trade name: Tocopherol 98, manufactured by Nisshin Oil Co., Ltd.) is mixed, and the mixture is stirred and cooled using a propeller at 4000 rpm and 60 ° C. until the components are sufficiently homogenized. The tocopherol preparation of the present invention was obtained. The formulation was a brown, viscous, homogeneous liquid.
[0026]
Production Comparative Example 1
3% by mass of soybean oil (trade name: soybean squeezed oil, manufactured by Nisshin Oil Co., Ltd.) and 97% by mass of soybean tocopherol (tocopherol content: 95%, α-tocopherol: 95% or more, manufactured by Nisshin Oil Co., Ltd.) Then, using a propeller, the mixture was stirred and cooled at 3000 rpm and 40 ° C. until the components were sufficiently homogenized to obtain a tocopherol preparation. The formulation was a brown, viscous, homogeneous liquid.
[0027]
Production Comparative Example 2
30% by mass of soybean oil (trade name: soybean squeezed oil, manufactured by Nisshin Oil Co., Ltd.) and 10% by mass of plant sterol (trade name: Phytosterol, manufactured by ADM) are mixed, and the mixture is mixed with a propeller at 4000 rpm and 60 ° C. Stir until the components are sufficiently homogenized under the conditions. Thereafter, 60% by mass of soybean tocopherol (trade name: Tocopherol 98, manufactured by Nisshin Oil Co., Ltd.) is mixed, and the mixture is stirred and cooled using a propeller at 4000 rpm and 60 ° C. until the components are sufficiently uniformized. A tocopherol preparation was obtained. Several hours after cooling, plant sterol crystals formed.
[0028]
Production Comparative Example 3
18% by mass of soybean oil (trade name: soybean squeezed oil, manufactured by Nisshin Oil Co., Ltd.), 10% by mass of plant sterol (trade name: Phytosterol, manufactured by ADM), lecithin (trade name: Basis LP-20, Nisshin) 20% by mass (manufactured by Oil Refining Co., Ltd.) were mixed and stirred using a homomixer at 4000 to 5000 rpm at 60 ° C. until the components were sufficiently homogenized. Thereafter, 52% by mass of soybean tocopherol (trade name: Tocopherol 98, manufactured by Nisshin Oil Co., Ltd.) is mixed, and the mixture is stirred and cooled using a propeller at 4000 rpm and 60 ° C. until the components are sufficiently homogenized. A tocopherol preparation was obtained. About one week after storage at room temperature, crystals of plant sterols formed.
[0029]
Table 1 shows the formulation of Production Examples 1 to 5 and Production Comparative Examples 1 to 3. In Production Comparative Examples 2 and 3, sterol crystal precipitation was observed after production or during storage, and the subsequent evaluation was not performed. In the sterol crystal precipitation state shown in Table 1, ◎ indicates extremely good, ○ indicates good but slightly turbid over time, △ indicates precipitation after a while, and × indicates precipitation immediately after production.
[0030]
[Table 1]
[0031]
Evaluation 1
Each of the tocopherol preparations of Production Examples 1 to 5 and Production Comparative Example 1 was stored at room temperature, and the flavor after one week and one month storage was evaluated in an aqueous solution state. Although the tocopherol preparation does not completely dissolve in water, since taste components are transferred to water, it is judged that sensory evaluation is possible, and a 1% aqueous solution is prepared. Evaluation was made based on the standard (the same applies to the following sensory evaluation). Table 2 shows the results.
(Evaluation criteria)
A: Good.
:: Somewhat good.
Δ: Somewhat bad.
×: Bad.
[0032]
[Table 2]
[0033]
The flavor of the tocopherol preparation of Production Comparative Example 1 became slightly worse one week after the start of storage, and worsened in January. On the other hand, in the tocopherol preparations of Production Examples 1 to 5, the one-month storage product was equal to or more than the one-week storage product of the tocopherol preparation of Production Comparative Example 1, and the effect of the present invention was confirmed. In particular, the tocopherol preparation of Production Example 1 had an extremely good flavor even after storage for one month.
[0034]
Evaluation 2
Emulsions were prepared using the tocopherol preparations of Production Examples 1 to 5 and Production Comparative Example 1. Each of the emulsions using the tocopherol preparation was stored at room temperature, and after storage for one week and one month, the flavor was changed to a 1% aqueous solution state, and sensory evaluation was performed by five panelists with five points. Table 3 shows the composition of the emulsion. Table 4 shows the results of the sensory evaluation.
[0035]
[Table 3]
[0036]
(Emulsion preparation method)
After uniformly mixing the aqueous phase, both the aqueous phase and the oil phase were heated to 60 to 65 ° C. The oil phase was dropped into the aqueous phase in a heated state to perform preliminary emulsification. After the preliminary emulsification, the mixture was emulsified with a high-pressure homogenizer to obtain an emulsion.
[0037]
[Table 4]
[0038]
The emulsion using the tocopherol preparation of Production Comparative Example 1 had a bad odor and taste after one week of storage, and deteriorated in taste, odor and appearance in January. On the other hand, the emulsions using the tocopherol preparations of Production Examples 1 to 5 are the same as or longer than the one-week preservation products of the emulsion using the tocopherol preparations of Production Comparative Example 1 for one week. The effect of the invention was confirmed. In particular, the emulsion using the tocopherol preparation of Production Example 1 had extremely good flavor and appearance even after storage for one month.
[0039]
Evaluation 3 <Beverage>
The emulsion obtained in Evaluation 2 is hereinafter referred to as Emulsions 1 to 5 and Emulsion Comparative Example 1.
Using the emulsion prepared in Evaluation 2, a beverage model was prepared according to a conventional method with the composition shown in Table 5. After the prepared beverage was refrigerated for one week, the sensory evaluation was performed by five panelists with five points. Table 6 shows the results.
[0040]
[Table 5]
[0041]
[Table 6]
[0042]
The beverages using Emulsions 1 to 5 all had better odor, taste, and appearance than the beverages using Emulsion Comparative Example 1.
[0043]
Evaluation 4 <acid milk drink>
Using the emulsion prepared in Evaluation 2, an acidic milk beverage was prepared according to a conventional method with the composition shown in Table 7. Table 8 shows the evaluation results of the acidic milk beverage.
[0044]
[Table 7]
[0045]
[Table 8]
[0046]
The acidic milk beverages using Emulsions 1 to 5 were all superior in odor, taste, and appearance to the acidic milk beverages using Emulsion Comparative Example 1.
[0047]
Evaluation 5 <Jelly>
Using the emulsion prepared in Evaluation 2, jelly was prepared according to a conventional method with the composition shown in Table 9. Table 10 shows the evaluation results of the prepared jelly.
[0048]
[Table 9]
[0049]
[Table 10]
[0050]
The jellies using Emulsions 1 to 5 all had better odor, taste and appearance than the jelly using Emulsion Comparative Example 1.
[0051]
Evaluation 6 <Margarine>
Using the tocopherol preparations of Production Examples 1 to 5 and Production Comparative Example 1, margarine was prepared according to a conventional method with the composition shown in Table 11. The prepared margarine was stored refrigerated for one month, and the flavors before the start of storage and after the end of storage were evaluated. Table 12 shows the evaluation results.
[0052]
[Table 11]
[0053]
[Table 12]
[0054]
The margarine using the tocopherol preparations of Production Examples 1 to 5 was superior in the flavor as compared with the margarine using the tocopherol preparation of Production Comparative Example 1.
[0055]
【The invention's effect】
The tocopherol preparation of the present invention is one in which deterioration in flavor during storage is significantly suppressed as compared with a conventional tocopherol preparation. Therefore, the deterioration of the flavor of the food and drink containing the tocopherol preparation can be similarly suppressed.
Further, when sterol and lecithin are blended, it is also effective in reducing blood lipids and the like.
Claims (11)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001042298A JP3597478B2 (en) | 2001-02-19 | 2001-02-19 | Tocopherol preparation with suppressed flavor deterioration and food and beverage containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001042298A JP3597478B2 (en) | 2001-02-19 | 2001-02-19 | Tocopherol preparation with suppressed flavor deterioration and food and beverage containing the same |
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| JP2002238500A JP2002238500A (en) | 2002-08-27 |
| JP3597478B2 true JP3597478B2 (en) | 2004-12-08 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1684598A2 (en) * | 2003-11-14 | 2006-08-02 | AQUANOVA German Solubilisate Technologies (AGT) GmbH | Oleaginous composition containing a flowable active ingredient |
| JP4634176B2 (en) | 2004-09-10 | 2011-02-16 | 理研ビタミン株式会社 | Improving the flavor of instant noodles |
| JP5037140B2 (en) * | 2007-01-09 | 2012-09-26 | 理研ビタミン株式会社 | L-ascorbic acid fatty acid ester-containing preparation |
| JP2013055891A (en) * | 2011-09-07 | 2013-03-28 | Riken Vitamin Co Ltd | Flavor deterioration inhibitor for food and drink containing fruit juice |
| JP5905944B2 (en) * | 2013-09-18 | 2016-04-20 | 日清オイリオグループ株式会社 | Oils and fats and foods containing oils and fats |
| JP6821249B2 (en) * | 2016-12-15 | 2021-01-27 | 日清オイリオグループ株式会社 | Cooking oil |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS6178368A (en) * | 1984-09-26 | 1986-04-21 | Riken Vitamin Co Ltd | Food grade antioxidant |
| JPH08120187A (en) * | 1994-10-26 | 1996-05-14 | Lion Corp | Carotenoid-containing aqueous composition and carotenoid-containing beverage |
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