CA2207325A1 - Anti-oxidant compositions - Google Patents

Anti-oxidant compositions

Info

Publication number: CA2207325A1
Authority: CA; Canada
Prior art keywords: composition; amphiphile; antioxidant; species; hydrophilic
Prior art date: 1994-12-09
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.): Abandoned

Application number

CA002207325A

Other languages

English (en)

French (fr)

Inventor

Christopher John Kirby

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cortecs Ltd

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-12-09

Filing date

1995-12-08

Publication date

1996-06-13

1995-12-08 Application filed by Individual filed Critical Individual

1996-06-13 Publication of CA2207325A1 publication Critical patent/CA2207325A1/en

Status Abandoned legal-status Critical Current

Links

239000003963 antioxidant agent Substances 0.000 title claims abstract description 87
235000006708 antioxidants Nutrition 0.000 title claims abstract description 83
230000003078 antioxidant effect Effects 0.000 title claims abstract description 81
239000000203 mixture Substances 0.000 title claims abstract description 69
239000002904 solvent Substances 0.000 claims abstract description 51
230000002209 hydrophobic effect Effects 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 37
230000008569 process Effects 0.000 claims abstract description 25
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 90
235000010323 ascorbic acid Nutrition 0.000 claims description 43
239000011668 ascorbic acid Substances 0.000 claims description 43
OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 40
229960005070 ascorbic acid Drugs 0.000 claims description 35
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 34
238000002360 preparation method Methods 0.000 claims description 20
230000003647 oxidation Effects 0.000 claims description 19
238000007254 oxidation reaction Methods 0.000 claims description 19
239000006185 dispersion Substances 0.000 claims description 18
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 16
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
150000002632 lipids Chemical class 0.000 claims description 13
150000003904 phospholipids Chemical class 0.000 claims description 12
RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims description 11
-1 ceruplasmin Chemical compound 0.000 claims description 9
108010024636 Glutathione Proteins 0.000 claims description 8
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 8
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 8
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 8
239000003809 bile pigment Substances 0.000 claims description 8
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 8
235000018417 cysteine Nutrition 0.000 claims description 8
229960003180 glutathione Drugs 0.000 claims description 8
235000003969 glutathione Nutrition 0.000 claims description 8
229940116269 uric acid Drugs 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
239000002537 cosmetic Substances 0.000 claims description 7
229930003427 Vitamin E Natural products 0.000 claims description 6
238000009472 formulation Methods 0.000 claims description 6
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 6
239000002691 unilamellar liposome Substances 0.000 claims description 6
235000019165 vitamin E Nutrition 0.000 claims description 6
239000011709 vitamin E Substances 0.000 claims description 6
229940046009 vitamin E Drugs 0.000 claims description 6
229960002433 cysteine Drugs 0.000 claims description 5
239000000693 micelle Substances 0.000 claims description 5
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
239000005642 Oleic acid Substances 0.000 claims description 4
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
238000004108 freeze drying Methods 0.000 claims description 4
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
DIGQNXIGRZPYDK-WKSCXVIASA-N (2R)-6-amino-2-[[2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R,3S)-2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S,3S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[2-[[2-[[2-[(2-amino-1-hydroxyethylidene)amino]-3-carboxy-1-hydroxypropylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxypropylidene]amino]-1,3-dihydroxypropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxybutylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1-hydroxypropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1,5-dihydroxy-5-iminopentylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxybutylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1-hydroxyethylidene]amino]hexanoic acid Chemical compound C[C@@H]([C@@H](C(=N[C@@H](CS)C(=N[C@@H](C)C(=N[C@@H](CO)C(=NCC(=N[C@@H](CCC(=N)O)C(=NC(CS)C(=N[C@H]([C@H](C)O)C(=N[C@H](CS)C(=N[C@H](CO)C(=NCC(=N[C@H](CS)C(=NCC(=N[C@H](CCCCN)C(=O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)N=C([C@H](CS)N=C([C@H](CO)N=C([C@H](CO)N=C([C@H](C)N=C(CN=C([C@H](CO)N=C([C@H](CS)N=C(CN=C(C(CS)N=C(C(CC(=O)O)N=C(CN)O)O)O)O)O)O)O)O)O)O)O)O DIGQNXIGRZPYDK-WKSCXVIASA-N 0.000 claims description 3
102100027211 Albumin Human genes 0.000 claims description 3
108010088751 Albumins Proteins 0.000 claims description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
102000003792 Metallothionein Human genes 0.000 claims description 3
108090000157 Metallothionein Proteins 0.000 claims description 3
102000006386 Myelin Proteins Human genes 0.000 claims description 3
108010083674 Myelin Proteins Proteins 0.000 claims description 3
GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 claims description 3
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 3
235000011180 diphosphates Nutrition 0.000 claims description 3
150000004668 long chain fatty acids Chemical class 0.000 claims description 3
PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 claims description 3
229960003775 miltefosine Drugs 0.000 claims description 3
210000005012 myelin Anatomy 0.000 claims description 3
YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 claims description 3
229950004354 phosphorylcholine Drugs 0.000 claims description 3
229920000642 polymer Polymers 0.000 claims description 3
YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims description 3
125000005457 triglyceride group Chemical group 0.000 claims description 3
WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims description 3
TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims description 3
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 3
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 3
235000012141 vanillin Nutrition 0.000 claims description 3
108050005077 Haptoglobin Proteins 0.000 claims description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 4
239000007787 solid Substances 0.000 claims 3
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims 2
IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims 2
IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims 2
102000004338 Transferrin Human genes 0.000 claims 2
108090000901 Transferrin Proteins 0.000 claims 2
229940068041 phytic acid Drugs 0.000 claims 2
235000002949 phytic acid Nutrition 0.000 claims 2
239000000467 phytic acid Substances 0.000 claims 2
229940048084 pyrophosphate Drugs 0.000 claims 2
239000012581 transferrin Substances 0.000 claims 2
102000014702 Haptoglobin Human genes 0.000 claims 1
239000008247 solid mixture Substances 0.000 claims 1
239000012071 phase Substances 0.000 description 36
241000894007 species Species 0.000 description 30
239000003921 oil Substances 0.000 description 26
235000019198 oils Nutrition 0.000 description 26
239000011732 tocopherol Substances 0.000 description 18
235000020778 linoleic acid Nutrition 0.000 description 16
OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 16
229960001295 tocopherol Drugs 0.000 description 16
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 15
235000010469 Glycine max Nutrition 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 9
HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 description 8
229940072107 ascorbate Drugs 0.000 description 8
HBOQXIRUPVQLKX-UHFFFAOYSA-N linoleic acid triglyceride Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC HBOQXIRUPVQLKX-UHFFFAOYSA-N 0.000 description 8
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235000014113 dietary fatty acids Nutrition 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
239000000194 fatty acid Substances 0.000 description 7
150000004665 fatty acids Chemical class 0.000 description 6
235000021323 fish oil Nutrition 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
230000003993 interaction Effects 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
235000019486 Sunflower oil Nutrition 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000002600 sunflower oil Substances 0.000 description 4
229930003799 tocopherol Natural products 0.000 description 4
239000004322 Butylated hydroxytoluene Substances 0.000 description 3
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229940123457 Free radical scavenger Drugs 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
235000010354 butylated hydroxytoluene 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
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
235000021313 oleic acid Nutrition 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
DANYIYRPLHHOCZ-UHFFFAOYSA-N 5,7-dihydroxy-4'-methoxyflavone Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 DANYIYRPLHHOCZ-UHFFFAOYSA-N 0.000 description 2
BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
239000004255 Butylated hydroxyanisole Substances 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 2
239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 2
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
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235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
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239000012528 membrane Substances 0.000 description 2
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238000005070 sampling Methods 0.000 description 2
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 2
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235000010384 tocopherol Nutrition 0.000 description 2
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235000019149 tocopherols Nutrition 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
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 description 2
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
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 1
GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 1
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
GWZYPXHJIZCRAJ-UHFFFAOYSA-N Biliverdin Natural products CC1=C(C=C)C(=C/C2=NC(=Cc3[nH]c(C=C/4NC(=O)C(=C4C)C=C)c(C)c3CCC(=O)O)C(=C2C)CCC(=O)O)NC1=O GWZYPXHJIZCRAJ-UHFFFAOYSA-N 0.000 description 1
RCNSAJSGRJSBKK-NSQVQWHSSA-N Biliverdin IX Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(\C=C/2C(=C(C)C(=C/C=3C(=C(C=C)C(=O)N=3)C)/N\2)CCC(O)=O)N1 RCNSAJSGRJSBKK-NSQVQWHSSA-N 0.000 description 1
ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000005792 Geraniol Substances 0.000 description 1
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
102100025255 Haptoglobin Human genes 0.000 description 1
LWHRXFOPIDTJSG-XPIVLIJGSA-N Isolipidiol Natural products O=C1[C@@H](C)[C@@H]2[C@@H](O)CC(=C)[C@H]3[C@H]([C@H](C)[C@@H](O)C3)[C@@H]2O1 LWHRXFOPIDTJSG-XPIVLIJGSA-N 0.000 description 1
GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 1
ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
238000005411 Van der Waals force Methods 0.000 description 1
229930003268 Vitamin C Natural products 0.000 description 1
235000009962 acacetin Nutrition 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 1
WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
229940072049 amyl acetate Drugs 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
QBUVFDKTZJNUPP-UHFFFAOYSA-N biliverdin-IXalpha Natural products N1C(=O)C(C)=C(C=C)C1=CC1=C(C)C(CCC(O)=O)=C(C=C2C(=C(C)C(C=C3C(=C(C=C)C(=O)N3)C)=N2)CCC(O)=O)N1 QBUVFDKTZJNUPP-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940115397 bornyl acetate Drugs 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000005354 coacervation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001086 cytosolic effect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000012041 food component Nutrition 0.000 description 1
239000005417 food ingredient Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
239000005337 ground glass Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000002502 liposome Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000004530 micro-emulsion Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
235000010388 propyl gallate Nutrition 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
235000005875 quercetin Nutrition 0.000 description 1
229960001285 quercetin Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000000527 sonication Methods 0.000 description 1
229940032094 squalane Drugs 0.000 description 1
229940031439 squalene Drugs 0.000 description 1
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
229940116411 terpineol Drugs 0.000 description 1
239000004250 tert-Butylhydroquinone Substances 0.000 description 1
235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229930003802 tocotrienol Natural products 0.000 description 1
239000011731 tocotrienol Substances 0.000 description 1
235000019148 tocotrienols Nutrition 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- 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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0028—Carboxylic acids; Their derivates
- 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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
- C11B5/005—Amines or imines
- 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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0071—Preserving by using additives, e.g. anti-oxidants containing halogens, sulfur or phosphorus
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Zoology (AREA)
Materials Engineering (AREA)
Epidemiology (AREA)
Birds (AREA)
Dermatology (AREA)
Emergency Medicine (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)

CA002207325A 1994-12-09 1995-12-08 Anti-oxidant compositions Abandoned CA2207325A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9424908.3A GB9424908D0 (en)	1994-12-09	1994-12-09	Anti-Oxidant Compositions
GB9424908.3		1994-12-09

Publications (1)

Publication Number	Publication Date
CA2207325A1 true CA2207325A1 (en)	1996-06-13

Family

ID=10765697

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002207325A Abandoned CA2207325A1 (en)	1994-12-09	1995-12-08	Anti-oxidant compositions

Country Status (12)

Country	Link
EP (1)	EP0796302A1 (de)
JP (1)	JPH10510563A (de)
CN (1)	CN1168687A (de)
AU (1)	AU700084B2 (de)
CA (1)	CA2207325A1 (de)
FI (1)	FI972421A7 (de)
GB (1)	GB9424908D0 (de)
IL (1)	IL116312A0 (de)
NO (1)	NO972609L (de)
NZ (1)	NZ297052A (de)
WO (1)	WO1996017899A1 (de)
ZA (1)	ZA9510506B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9323588D0 (en)	1993-11-16	1994-01-05	Cortecs Ltd	Hydrophobic preparation
US6278004B1 (en)	1996-11-06	2001-08-21	Aventis Pharma Deutschland Gmbh	Stabilized phospholipidic composition
US6458373B1 (en)	1997-01-07	2002-10-01	Sonus Pharmaceuticals, Inc.	Emulsion vehicle for poorly soluble drugs
US7030155B2 (en)	1998-06-05	2006-04-18	Sonus Pharmaceuticals, Inc.	Emulsion vehicle for poorly soluble drugs
US8034372B2 (en) *	2003-03-05	2011-10-11	Nestec, Ltd.	Dietary supplement for athletic pets
DE102006035040A1 (de) *	2006-07-28	2008-01-31	Beiersdorf Ag	Wirkstoffkombinationen aus Ascorbylverbindung und hydriertem Lecithin
JP2008174512A (ja) *	2007-01-22	2008-07-31	Kracie Seiyaku Kk	起床時疲労感改善用組成物
US20140308733A1 (en) *	2011-09-08	2014-10-16	Calpis Co., Ltd.	Method for inducing germination of spore forming bacterium
CN103876243B (zh) *	2012-12-21	2015-11-11	贵州天刺力食品科技有限责任公司	复配抗氧化剂
CN103518975B (zh) *	2013-10-23	2015-01-21	麦仑(漳州)生物科技有限公司	一种动物饲料用复合抗氧化剂及制备方法
FR3012292B1 (fr) *	2013-10-24	2016-07-15	Polaris	Composition antioxydante destinee a la stabilisation oxydative des huiles marines, animales ou vegetales
PE20251527A1 (es) *	2017-08-25	2025-06-05	Dsm Ip Assets Bv	Nueva formulacion
CN108379094B (zh) *	2018-04-24	2021-09-14	广州暨南大学医药生物技术研究开发中心有限公司	包含生物活性美容多肽脂质立方晶的组合物及其在化妆品中的应用
JP2024522208A (ja) *	2021-06-11	2024-06-11	ブリクストンバイオサイエンシズインコーポレイテッド	リポソームエマルジョンを使用してスラリーを作製する方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH676470A5 (de) *	1988-02-03	1991-01-31	Nestle Sa
KR910004884B1 (ko) *	1989-02-01	1991-07-15	한국식품개발연구원	유지류의 산화억제방법
US5084293A (en) *	1990-06-26	1992-01-28	Kalamazoo Holdings, Inc.	Activated ascorbic acid antioxidant compositions and carotenoids, fats, and foods stabilized therewith
US5077069A (en) *	1991-01-07	1991-12-31	Kabi Pharmacia Ab	Composition of natural antioxidants for the stabilization of polyunsaturated oils
EP0514576A1 (de) *	1991-05-24	1992-11-25	Societe Des Produits Nestle S.A.	Öllösliche Antioxydationsmischung

1994
- 1994-12-09 GB GBGB9424908.3A patent/GB9424908D0/en active Pending
1995
- 1995-12-08 WO PCT/GB1995/002888 patent/WO1996017899A1/en not_active Ceased
- 1995-12-08 CN CN95196630.8A patent/CN1168687A/zh active Pending
- 1995-12-08 EP EP95940348A patent/EP0796302A1/de not_active Ceased
- 1995-12-08 FI FI972421A patent/FI972421A7/fi unknown
- 1995-12-08 AU AU41826/96A patent/AU700084B2/en not_active Ceased
- 1995-12-08 NZ NZ297052A patent/NZ297052A/xx unknown
- 1995-12-08 CA CA002207325A patent/CA2207325A1/en not_active Abandoned
- 1995-12-08 JP JP8517434A patent/JPH10510563A/ja active Pending
- 1995-12-10 IL IL11631295A patent/IL116312A0/xx unknown
- 1995-12-11 ZA ZA9510506A patent/ZA9510506B/xx unknown
1997
- 1997-06-06 NO NO972609A patent/NO972609L/no unknown

Also Published As

Publication number	Publication date
AU700084B2 (en)	1998-12-24
CN1168687A (zh)	1997-12-24
NO972609L (no)	1997-08-08
IL116312A0 (en)	1996-03-31
NZ297052A (en)	1999-05-28
FI972421L (fi)	1997-08-06
MX9704273A (es)	1997-09-30
FI972421A0 (fi)	1997-06-06
NO972609D0 (no)	1997-06-06
AU4182696A (en)	1996-06-26
ZA9510506B (en)	1997-09-11
WO1996017899A1 (en)	1996-06-13
FI972421A7 (fi)	1997-08-06
GB9424908D0 (en)	1995-02-08
JPH10510563A (ja)	1998-10-13
EP0796302A1 (de)	1997-09-24

Legal Events

Date	Code	Title	Description
2000-12-08	FZDE	Discontinued
2022-09-10	FZDE	Discontinued	Effective date: 20001208

Publication	Publication Date	Title
AU700084B2 (en)	1998-12-24	Anti-oxidant compositions
US5968549A (en)	1999-10-19	Solubilisation aids
Taladrid et al.	2017	Effect of chemical composition and sonication procedure on properties of food-grade soy lecithin liposomes with added glycerol
US5688528A (en)	1997-11-18	Oil-in water emulsions
CA2182577C (en)	2002-08-20	Lipophilic carrier preparations
Belhaj et al.	2010	Oxidative kinetics of salmon oil in bulk and in nanoemulsion stabilized by marine lecithin
JP3103430B2 (ja)	2000-10-30	脂溶性抗酸化剤混合物
JP5728152B2 (ja)	2015-06-03	乾燥リポソーム製剤
MXPA98001863A (en)	1999-02-24	Microemuls
AU2003242589A1 (en)	2003-12-19	Oil-soluble pigment compositions
US10080803B2 (en)	2018-09-25	Emulsified krill phospholipid compositions
JPH06279467A (ja)	1994-10-04	リン脂質組成物
KR20000064684A (ko)	2000-11-06	소수성용매중에친수성물질(예,단백질)을용해시키는방법
MXPA97004273A (es)	1998-07-03	Composiciones antioxidantes
CA2207274A1 (en)	1996-06-13	Sequestration agents
JP2514995B2 (ja)	1996-07-10	経皮、経粘膜による物質の吸収を促進する組成物
JPH02203928A (ja)	1990-08-13	界面活性作用の強化されたグリセロ燐脂質組成物
JPH0899821A (ja)	1996-04-16	皮膚外用剤
MXPA97004274A (en)	1998-07-03	Auxiliary solubilization for macromoleculashidrofili
MXPA97004272A (en)	1998-11-09	Seized agents