JP7219251B2 - 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 - Google Patents
多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 Download PDFInfo
- Publication number
- JP7219251B2 JP7219251B2 JP2020164589A JP2020164589A JP7219251B2 JP 7219251 B2 JP7219251 B2 JP 7219251B2 JP 2020164589 A JP2020164589 A JP 2020164589A JP 2020164589 A JP2020164589 A JP 2020164589A JP 7219251 B2 JP7219251 B2 JP 7219251B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mct
- mcts
- composition
- oil
- 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.)
- Active
Links
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 title claims description 49
- 239000000203 mixture Substances 0.000 title claims description 34
- 239000005639 Lauric acid Substances 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title description 15
- -1 medium-chain fatty acid triglycerides Chemical class 0.000 title description 11
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 14
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 12
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 7
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 6
- 229960002446 octanoic acid Drugs 0.000 claims description 6
- 150000004667 medium chain fatty acids Chemical class 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 56
- 150000004702 methyl esters Chemical class 0.000 description 29
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- 101710137760 Malonyl-CoA-acyl carrier protein transacylase, mitochondrial Proteins 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 235000011187 glycerol Nutrition 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 235000013305 food Nutrition 0.000 description 15
- 230000008569 process Effects 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 229930195729 fatty acid Natural products 0.000 description 14
- 150000004665 fatty acids Chemical class 0.000 description 13
- 239000002537 cosmetic Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 230000032050 esterification Effects 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000005194 fractionation Methods 0.000 description 8
- 235000019864 coconut oil Nutrition 0.000 description 7
- 239000003240 coconut oil Substances 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 235000019865 palm kernel oil Nutrition 0.000 description 6
- 239000003346 palm kernel oil Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000015872 dietary supplement Nutrition 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates 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
- 235000013365 dairy product Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000021360 Myristic acid Nutrition 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000008162 cooking oil Substances 0.000 description 2
- 239000008406 cosmetic ingredient Substances 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000003084 food emulsifier Nutrition 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 235000021472 generally recognized as safe Nutrition 0.000 description 2
- 230000007407 health benefit Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910001410 inorganic ion Inorganic materials 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 235000021559 Fruit Juice Concentrate Nutrition 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 206010021034 Hypometabolism Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 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
- 239000007961 artificial flavoring substance Substances 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000003931 cognitive performance Effects 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 235000015897 energy drink Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 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
- 235000019645 odor Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 235000021085 polyunsaturated fats Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 238000013515 script Methods 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000010692 trans-unsaturated fatty acids Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/04—Refining fats or fatty oils by chemical reaction with acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/005—Splitting up mixtures of fatty acids into their constituents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Description
2. EP2636307. Lobee HWJ, Kruidenberg MB. Antimicrobial composition containing free fatty acids and method for its production. Sep 11 2013
3. GB879211. Crawford RV, Southern CW. Improvements in or relating to glyceride esters. Oct 4 1961
4. JP2009142185. Onishi K, Shono Y, Suzuki K, Toda T, Haruna H. Oil And fat composition for cream, and cream containing the same. Jul 2 2009
5. US2006817558. Beetham P; Beetham pPR; Gocal G; Gocal GFV; Gocal GFW; Knuth M; Knuth ME; Walker K; Walker KA. Fatty acid mixtures and use thereof. May 27 2013
6. US20100119684A1. Santana RD et al. Food compositions incorporating medium chain triglycerides. May 13 2010
7. US20130017278A1. Keller A. Composition and method for improving brain function. Jan 17 2013
8. US2238442. DREW ERNEST F.Mixed capric-caprylic esters and method of making same. Apr 15 1941
9. US6835750B1. Henderson ST. Use of medium chain triglycerides for the treatment and prevention of alzheimer's disease and other diseases resulting from reduced neuronal metabolism II. Dec 28 2004
10. US7470445B2. Takeuchi H. Oil or fat composition. Dec 30 2008
11. US8586060B2. Brinkmann B. Cosmetic or pharmaceutical preparation. Nov 19 2013
2. Lindqvist B, Sjogren I, Nordin R. Preparative fractionation of triglyceride mixtures according to acyl carbon number, using hydroxyalkoxypropyl Sephadex. J Lipid Res. 1974 Jan; 15(1):65-73.
3. Marten B, Pfeuffer M, Schrezenmeir J. Medium-chain triglycerides. International Dairy Journal 16 (2006) 1374-1382.
4. Traul KA, Driedger A, Ingle DL, Nakhasi D. Review of the toxicologic properties of medium-chain triglycerides. Food Chem Toxicol. 2000 Jan;38(1):79-98.
5. US FDA. http://www.accessdata.fda.gov/scripts/fdcc/?set=GRASNotices&id=449. July 7, 2014
トリグリセリド形態に加えて、本明細書に提示されるMCT油は更に、好ましくは、高純度ベントナイト粘土、ヒュームドシリカ、及びケイ酸アルミニウムマグネシウムを混合物全体の3.5%w/w以下で組み込むことによって、皮膚化粧品用途向けの軟質ゲルにするために化粧品グレードの増粘剤/ゲル化剤と混合することにより調製可能である。
Claims (3)
- 45%のC8(カプリル酸)、35%のC10(カプリン酸)、及び20%のC12(ラウリン酸)を含む、中鎖脂肪酸トリグリセリド組成物。
- 45%のC8(カプリル酸)、31%のC10(カプリン酸)、及び20%のC12(ラウリン酸)を含む、中鎖脂肪酸トリグリセリド組成物。
- 35%のC8(カプリル酸)、35%のC10(カプリン酸)、及び30%のC12(ラウリン酸)を含む、中鎖脂肪酸トリグリセリド組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PH12014000195A PH12014000195A1 (en) | 2014-07-10 | 2014-07-10 | Preparation and composition of medium chain triglycerides containing substantial amount of lauric acid |
PH1-2014-000195 | 2014-07-10 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018238583A Division JP2019056125A (ja) | 2014-07-10 | 2018-12-20 | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの新規組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021011576A JP2021011576A (ja) | 2021-02-04 |
JP7219251B2 true JP7219251B2 (ja) | 2023-02-07 |
Family
ID=55064550
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016572237A Pending JP2017523261A (ja) | 2014-07-10 | 2014-07-25 | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 |
JP2018238583A Pending JP2019056125A (ja) | 2014-07-10 | 2018-12-20 | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの新規組成物 |
JP2020164589A Active JP7219251B2 (ja) | 2014-07-10 | 2020-09-30 | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016572237A Pending JP2017523261A (ja) | 2014-07-10 | 2014-07-25 | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 |
JP2018238583A Pending JP2019056125A (ja) | 2014-07-10 | 2018-12-20 | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの新規組成物 |
Country Status (10)
Country | Link |
---|---|
US (1) | US10327452B2 (ja) |
JP (3) | JP2017523261A (ja) |
KR (2) | KR102229104B1 (ja) |
CN (1) | CN106659176A (ja) |
AU (3) | AU2014400680A1 (ja) |
DE (1) | DE112014006800T5 (ja) |
GB (2) | GB2583050B (ja) |
MY (1) | MY181997A (ja) |
PH (1) | PH12014000195A1 (ja) |
WO (1) | WO2016007026A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6343407B1 (ja) * | 2016-07-27 | 2018-06-13 | 日清オイリオグループ株式会社 | 油脂組成物 |
GB201619789D0 (en) * | 2016-11-23 | 2017-01-04 | Pepsis Ltd | Enzyme-rich malt extract formulations |
KR102446371B1 (ko) * | 2019-06-11 | 2022-09-22 | 대봉엘에스 주식회사 | 유지 조성물 및 이의 용도 |
IL268457B (en) * | 2019-08-04 | 2022-05-01 | Omega 3 Galilee Ltd | Oil suspension of edible solids and methods of preparation |
US20230134377A1 (en) * | 2021-10-31 | 2023-05-04 | One-Derings LLC | Insect-repellent personal-care composition |
US11946011B1 (en) * | 2022-10-28 | 2024-04-02 | Perlman Consulting, Llc | Stabilized medium chain triglyceride-based household lubricant and protective coating |
CN115925540A (zh) * | 2022-11-09 | 2023-04-07 | 广东聚石科技研究有限公司 | 一种三羟甲基丙烷中碳链酯及其制备方法和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004008165A (ja) | 2002-06-11 | 2004-01-15 | Nof Corp | 中鎖脂肪含有ゲル状食品 |
US20090311367A1 (en) | 2008-06-17 | 2009-12-17 | Perry Stephen C | Dietary Supplement |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2238442A (en) * | 1939-05-25 | 1941-04-15 | Ernest F Drew | Mixed capric-caprylic esters and method of making same |
GB879211A (en) | 1958-06-20 | 1961-10-04 | Bibby & Sons Ltd J | Improvements in or relating to glyceride esters |
US5000975A (en) * | 1988-12-29 | 1991-03-19 | American Home Products Corporation | Randomized palm oil fat composition for infant formulas |
NO301574B1 (no) | 1996-06-27 | 1997-11-17 | Jan Oxholm Gordeladze | Energidrikk |
US6835408B2 (en) | 1998-11-13 | 2004-12-28 | The Nisshin Oillio Group, Ltd. | Oil or fat composition |
US6835750B1 (en) | 2000-05-01 | 2004-12-28 | Accera, Inc. | Use of medium chain triglycerides for the treatment and prevention of alzheimer's disease and other diseases resulting from reduced neuronal metabolism II |
GB0301577D0 (en) * | 2003-01-23 | 2003-02-26 | Edko Pazarlama Tanitim Ltd Sti | Topical pharmaceutical and/or cosmetic dispense systems |
US8029579B2 (en) | 2006-06-28 | 2011-10-04 | COH Inc. | Fatty acid blends and uses therefor |
JP5930582B2 (ja) | 2007-04-02 | 2016-06-08 | ネステク ソシエテ アノニム | 中鎖トリグリセリドを包含する食品組成物 |
DE102007031697A1 (de) | 2007-07-06 | 2009-01-08 | Walter Rau Neusser Öl und Fett AG | Kosmetische oder pharmazeutische Zubereitung |
JP4925458B2 (ja) | 2007-12-13 | 2012-04-25 | 日清オイリオグループ株式会社 | クリーム用油脂組成物及び該油脂組成物を含有するクリーム |
US20120315369A1 (en) * | 2011-06-10 | 2012-12-13 | Jeffrey John Kester | Cookware Release Compositions |
US20130017278A1 (en) | 2011-07-13 | 2013-01-17 | Arlene Keller | Composition and method for improving brain function |
TWI572352B (zh) | 2012-03-01 | 2017-03-01 | 波麥堤克藥學Smt有限公司 | 用於製備具中鏈長度之脂肪酸的三酸甘油酯之方法 |
DK2636307T3 (en) | 2012-03-07 | 2015-02-09 | Cargill Inc | The process for preparing the anti-microbial composition comprising free fatty acids |
-
2014
- 2014-07-10 PH PH12014000195A patent/PH12014000195A1/en unknown
- 2014-07-25 JP JP2016572237A patent/JP2017523261A/ja active Pending
- 2014-07-25 CN CN201480080505.1A patent/CN106659176A/zh active Pending
- 2014-07-25 KR KR1020197033409A patent/KR102229104B1/ko active IP Right Grant
- 2014-07-25 GB GB2011795.8A patent/GB2583050B/en active Active
- 2014-07-25 US US15/324,298 patent/US10327452B2/en active Active
- 2014-07-25 KR KR1020177003873A patent/KR20170031738A/ko active Application Filing
- 2014-07-25 DE DE112014006800.4T patent/DE112014006800T5/de not_active Withdrawn
- 2014-07-25 MY MYPI2017700048A patent/MY181997A/en unknown
- 2014-07-25 WO PCT/PH2014/000015 patent/WO2016007026A1/en active Application Filing
- 2014-07-25 GB GB1620404.2A patent/GB2544204A/en not_active Withdrawn
- 2014-07-25 AU AU2014400680A patent/AU2014400680A1/en not_active Abandoned
-
2018
- 2018-12-20 JP JP2018238583A patent/JP2019056125A/ja active Pending
-
2019
- 2019-11-08 AU AU2019261791A patent/AU2019261791A1/en not_active Abandoned
-
2020
- 2020-09-30 JP JP2020164589A patent/JP7219251B2/ja active Active
-
2021
- 2021-05-20 AU AU2021203256A patent/AU2021203256A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004008165A (ja) | 2002-06-11 | 2004-01-15 | Nof Corp | 中鎖脂肪含有ゲル状食品 |
US20090311367A1 (en) | 2008-06-17 | 2009-12-17 | Perry Stephen C | Dietary Supplement |
Non-Patent Citations (1)
Title |
---|
ココナード(COCONARD) カタログ,花王の中鎖脂肪酸トリグリセライド(MCT),日本,花王株式会社 ケミカル事業ユニット,2000年07月01日,p.1-6 |
Also Published As
Publication number | Publication date |
---|---|
AU2021203256A1 (en) | 2021-06-17 |
MY181997A (en) | 2021-01-18 |
AU2014400680A1 (en) | 2017-01-05 |
US20170172170A1 (en) | 2017-06-22 |
JP2021011576A (ja) | 2021-02-04 |
KR20170031738A (ko) | 2017-03-21 |
AU2019261791A1 (en) | 2019-11-28 |
KR102229104B1 (ko) | 2021-03-18 |
JP2019056125A (ja) | 2019-04-11 |
KR20190129143A (ko) | 2019-11-19 |
GB2583050B (en) | 2021-03-24 |
JP2017523261A (ja) | 2017-08-17 |
CN106659176A (zh) | 2017-05-10 |
WO2016007026A1 (en) | 2016-01-14 |
GB202011795D0 (en) | 2020-09-09 |
DE112014006800T5 (de) | 2017-04-06 |
GB2583050A (en) | 2020-10-14 |
GB201620404D0 (en) | 2017-01-18 |
GB2544204A (en) | 2017-05-10 |
PH12014000195A1 (en) | 2017-01-23 |
US10327452B2 (en) | 2019-06-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7219251B2 (ja) | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 | |
KR100740564B1 (ko) | 공액화 리놀레산의 디글리세리드가 풍부한 유지조성물 | |
ES2770068T3 (es) | Proceso para refinar aceite vegetal con supresión de impurezas no deseadas | |
JP5088347B2 (ja) | 食感改良油脂組成物 | |
JP3375726B2 (ja) | 食用油脂および油脂混合物 | |
US5151291A (en) | Glycerides of eicosapentaenoic acid, processes for preparing the same and oil and fat products containing the same | |
KR19990082065A (ko) | 아라키돈산 및 도코사헥사엔산을 함유하는 장용 조제 또는 영양보충제 | |
KR101586502B1 (ko) | 마린 오일의 탈취 및 안정화 | |
TW201827599A (zh) | 脂肪酸乙酯之製備方法 | |
EP1783200B1 (de) | Strukturierte Lipidgemische mit CLA, omega-3 und/oder 6 Fettsäuren, und mittelkettigen Fettsäuren | |
US3748348A (en) | Directed-interesterified glyceridic oils having a high linoleic acid content and process for their production | |
JPH05507107A (ja) | 中及び長鎖脂肪酸トリグリセリド含有複合混合物を分別する向流液体/液体抽出 | |
WO2005079591A1 (fr) | Compositions de graisses et d'huiles contenant des diglycerides, et margarines, huiles de friture et aliments contenant ces compositions | |
JP5118284B2 (ja) | 水中油型乳化組成物 | |
JPS58167543A (ja) | 合成液状蝋エステル | |
JP2009240220A (ja) | 可塑性油脂組成物 | |
JP4381362B2 (ja) | 油中水型乳化組成物 | |
JP2016202001A (ja) | 油脂組成物 | |
JPH02158695A (ja) | 食餌用油脂及びこれを含有する食品 | |
JP4191420B2 (ja) | 甘草疎水性抽出物を含有してなる食用油脂組成物 | |
Gustafson et al. | Pycnanthus angolensis: Bioactive compounds and medicinal applications | |
JP3082280B2 (ja) | 食品のカロリー低減方法 | |
JP3537840B2 (ja) | 食用エステル交換油脂ならびにそれを用いた栄養組成物 | |
JP7283176B2 (ja) | 調製粉乳用油脂、調製粉乳用油脂組成物、および調製粉乳 | |
JP3135370B2 (ja) | 低カロリー油脂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20201028 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20201028 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20211105 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220204 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20220516 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220916 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20220916 |
|
C11 | Written invitation by the commissioner to file amendments |
Free format text: JAPANESE INTERMEDIATE CODE: C11 Effective date: 20220928 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20221114 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20221115 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20221129 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20221227 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230126 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7219251 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |