JP2010532418A - 多価不飽和脂肪酸のエステルの製造方法および精製方法 - Google Patents
多価不飽和脂肪酸のエステルの製造方法および精製方法 Download PDFInfo
- Publication number
- JP2010532418A JP2010532418A JP2010515186A JP2010515186A JP2010532418A JP 2010532418 A JP2010532418 A JP 2010532418A JP 2010515186 A JP2010515186 A JP 2010515186A JP 2010515186 A JP2010515186 A JP 2010515186A JP 2010532418 A JP2010532418 A JP 2010532418A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- ester
- acid
- fatty acid
- polyunsaturated fatty
- 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.)
- Pending
Links
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 238
- 150000002148 esters Chemical class 0.000 title claims abstract description 208
- 238000000034 method Methods 0.000 title claims abstract description 153
- 230000008569 process Effects 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims abstract description 300
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 110
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 52
- 150000004665 fatty acids Chemical group 0.000 claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 120
- 125000004494 ethyl ester group Chemical group 0.000 claims description 77
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 68
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 claims description 66
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 63
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 60
- 244000005700 microbiome Species 0.000 claims description 54
- 241000196324 Embryophyta Species 0.000 claims description 38
- 150000003626 triacylglycerols Chemical class 0.000 claims description 37
- 239000004202 carbamide Substances 0.000 claims description 36
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims description 34
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 29
- 229930195729 fatty acid Natural products 0.000 claims description 29
- 239000000194 fatty acid Substances 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 28
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 27
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 27
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 24
- 150000002978 peroxides Chemical class 0.000 claims description 22
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 20
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 18
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 18
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 229960004488 linolenic acid Drugs 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- 239000011574 phosphorus Substances 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 16
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 15
- 235000021588 free fatty acids Nutrition 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- 238000007670 refining Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 13
- 235000021342 arachidonic acid Nutrition 0.000 claims description 12
- 229940114079 arachidonic acid Drugs 0.000 claims description 12
- 238000004061 bleaching Methods 0.000 claims description 12
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 12
- 238000005809 transesterification reaction Methods 0.000 claims description 12
- 238000004332 deodorization Methods 0.000 claims description 11
- SOQKXJABGLKWQX-UHFFFAOYSA-N octacosa-4,7,10,13,16,19,22,25-octaenoic acid Chemical compound CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCCC(O)=O SOQKXJABGLKWQX-UHFFFAOYSA-N 0.000 claims description 11
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 11
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 10
- 241000233671 Schizochytrium Species 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 241000199914 Dinophyceae Species 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 238000004807 desolvation Methods 0.000 claims description 8
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 8
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 claims description 8
- 241000235575 Mortierella Species 0.000 claims description 7
- 108010030975 Polyketide Synthases Proteins 0.000 claims description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 7
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims description 7
- 241000195493 Cryptophyta Species 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 6
- 235000010469 Glycine max Nutrition 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 240000008042 Zea mays Species 0.000 claims description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 6
- 235000005822 corn Nutrition 0.000 claims description 6
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 claims description 5
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 5
- 244000105624 Arachis hypogaea Species 0.000 claims description 5
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 5
- 235000018262 Arachis monticola Nutrition 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 5
- 240000004355 Borago officinalis Species 0.000 claims description 5
- 235000007689 Borago officinalis Nutrition 0.000 claims description 5
- 241000219198 Brassica Species 0.000 claims description 5
- 235000003351 Brassica cretica Nutrition 0.000 claims description 5
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 5
- 240000002791 Brassica napus Species 0.000 claims description 5
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 5
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 5
- 235000003343 Brassica rupestris Nutrition 0.000 claims description 5
- 244000188595 Brassica sinapistrum Species 0.000 claims description 5
- 244000020518 Carthamus tinctorius Species 0.000 claims description 5
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 5
- 244000045195 Cicer arietinum Species 0.000 claims description 5
- 235000010523 Cicer arietinum Nutrition 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 5
- 241000219146 Gossypium Species 0.000 claims description 5
- 244000020551 Helianthus annuus Species 0.000 claims description 5
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 5
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 claims description 5
- 244000043158 Lens esculenta Species 0.000 claims description 5
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 5
- 240000006240 Linum usitatissimum Species 0.000 claims description 5
- 244000061176 Nicotiana tabacum Species 0.000 claims description 5
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 5
- 241000219925 Oenothera Species 0.000 claims description 5
- 235000004496 Oenothera biennis Nutrition 0.000 claims description 5
- 240000007817 Olea europaea Species 0.000 claims description 5
- 244000042324 Trifolium repens Species 0.000 claims description 5
- 235000013540 Trifolium repens var repens Nutrition 0.000 claims description 5
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 235000004426 flaxseed Nutrition 0.000 claims description 5
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims description 5
- 229960002733 gamolenic acid Drugs 0.000 claims description 5
- 235000010460 mustard Nutrition 0.000 claims description 5
- 235000020232 peanut Nutrition 0.000 claims description 5
- 241001133760 Acoelorraphe Species 0.000 claims description 4
- 241001467333 Thraustochytriaceae Species 0.000 claims description 4
- 238000012239 gene modification Methods 0.000 claims description 4
- 230000005017 genetic modification Effects 0.000 claims description 4
- 235000013617 genetically modified food Nutrition 0.000 claims description 4
- 241000256111 Aedes <genus> Species 0.000 claims description 3
- 241000238424 Crustacea Species 0.000 claims description 3
- 241000255777 Lepidoptera Species 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 241000199913 Crypthecodinium Species 0.000 claims description 2
- 241000233675 Thraustochytrium Species 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 15
- 238000000746 purification Methods 0.000 abstract description 6
- 239000003921 oil Substances 0.000 description 72
- 235000019198 oils Nutrition 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- 235000013305 food Nutrition 0.000 description 43
- 239000000243 solution Substances 0.000 description 41
- 239000002585 base Substances 0.000 description 37
- 238000004817 gas chromatography Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- -1 saturated fatty acid esters Chemical class 0.000 description 20
- ITNKVODZACVXDS-YNUSHXQLSA-N ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate Chemical compound CCOC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ITNKVODZACVXDS-YNUSHXQLSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000605 extraction Methods 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- 241000894007 species Species 0.000 description 13
- 239000010779 crude oil Substances 0.000 description 12
- 235000013350 formula milk Nutrition 0.000 description 11
- 150000002632 lipids Chemical class 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000008452 baby food Nutrition 0.000 description 8
- 238000004508 fractional distillation Methods 0.000 description 8
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 8
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VCSQUSNNIFZJAP-AAQCHOMXSA-N ethyl (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate Chemical compound CCOC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC VCSQUSNNIFZJAP-AAQCHOMXSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 241000907999 Mortierella alpina Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 235000013361 beverage Nutrition 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 235000016709 nutrition Nutrition 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000011888 snacks Nutrition 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 4
- 235000021056 liquid food Nutrition 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 3
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
- 241001491708 Macrocystis Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 235000013365 dairy product Nutrition 0.000 description 3
- 230000000378 dietary effect Effects 0.000 description 3
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
- 235000020667 long-chain omega-3 fatty acid Nutrition 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 235000014571 nuts Nutrition 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- 241000206761 Bacillariophyta Species 0.000 description 2
- 241000321369 Cephalopholis fulva Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001137251 Corvidae Species 0.000 description 2
- 241000199912 Crypthecodinium cohnii Species 0.000 description 2
- 241000989765 Diplophrys Species 0.000 description 2
- 241000239366 Euphausiacea Species 0.000 description 2
- 102000015303 Fatty Acid Synthases Human genes 0.000 description 2
- 108010039731 Fatty Acid Synthases Proteins 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 2
- 244000194101 Ginkgo biloba Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001467308 Labyrinthuloides Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000288906 Primates Species 0.000 description 2
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 2
- 241000598397 Schizochytrium sp. Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241001466451 Stramenopiles Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 235000013351 cheese Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000014510 cooky Nutrition 0.000 description 2
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 235000020256 human milk Nutrition 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 235000010598 long-chain omega-6 fatty acid Nutrition 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 235000015108 pies Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 229960001685 tacrine Drugs 0.000 description 2
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 2
- 235000008371 tortilla/corn chips Nutrition 0.000 description 2
- 229960005486 vaccine Drugs 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 235000019195 vitamin supplement Nutrition 0.000 description 2
- 235000013618 yogurt Nutrition 0.000 description 2
- OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 description 1
- PWWHPNUWGBQCGO-WDEREUQCSA-N (2s)-n-[2-[[(2r)-4-methyl-2-(methylamino)pentanoyl]amino]acetyl]pyrrolidine-2-carboxamide Chemical compound CC(C)C[C@@H](NC)C(=O)NCC(=O)NC(=O)[C@@H]1CCCN1 PWWHPNUWGBQCGO-WDEREUQCSA-N 0.000 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- DSQFSRAJFCOGKA-GKFVBPDJSA-N (5z,8z,11z,14z)-2-ethylicosa-5,8,11,14-tetraenoic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC(CC)C(O)=O DSQFSRAJFCOGKA-GKFVBPDJSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products 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 1
- WAWDOEHEAULMGC-UHFFFAOYSA-N 3-[(6-butoxypyridin-3-yl)diazenyl]pyridine-2,6-diamine Chemical compound C1=NC(OCCCC)=CC=C1N=NC1=CC=C(N)N=C1N WAWDOEHEAULMGC-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 1
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 1
- 241000003610 Aplanochytrium Species 0.000 description 1
- 241000178280 Aureococcus Species 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 241001655287 Chlamydomyxa Species 0.000 description 1
- 241000195628 Chlorophyta Species 0.000 description 1
- 241000199485 Chromulina Species 0.000 description 1
- 241000534675 Chrysomeridales Species 0.000 description 1
- 241000206751 Chrysophyceae Species 0.000 description 1
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 1
- 241001633026 Coenocystis Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 241001494734 Dictyochales Species 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241001462977 Elina Species 0.000 description 1
- 241000224472 Eustigmatophyceae Species 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 241001466486 Hibberdiales Species 0.000 description 1
- 241001306467 Hydrurales Species 0.000 description 1
- 206010020772 Hypertension 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000003482 Japonochytrium Species 0.000 description 1
- 241001491670 Labyrinthula Species 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 201000002832 Lewy body dementia Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000907923 Mortierella schmuckeri Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 241000472328 Parmales Species 0.000 description 1
- 241001494726 Pedinellales Species 0.000 description 1
- 241001494851 Pelagococcus Species 0.000 description 1
- 241000199919 Phaeophyceae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241001518925 Raphidophyceae Species 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000193082 Sarcinochrysidales Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 241000864178 Sorodiplophrys Species 0.000 description 1
- 241000592344 Spermatophyta Species 0.000 description 1
- 241001491678 Ulkenia Species 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003627 anti-cholesterol Effects 0.000 description 1
- 229940005524 anti-dementia drug Drugs 0.000 description 1
- 229940127003 anti-diabetic drug Drugs 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- SNXPWYFWAZVIAU-UHFFFAOYSA-N arachidonic acid ethyl ester Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)OCC SNXPWYFWAZVIAU-UHFFFAOYSA-N 0.000 description 1
- 229940039856 aricept Drugs 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 229960001770 atorvastatin calcium Drugs 0.000 description 1
- FQCKMBLVYCEXJB-MNSAWQCASA-L atorvastatin calcium Chemical compound [Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 FQCKMBLVYCEXJB-MNSAWQCASA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000015496 breakfast cereal Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000010307 cell transformation Effects 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
- 229960005228 clioquinol Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 235000012495 crackers Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 235000012754 curcumin Nutrition 0.000 description 1
- 229940109262 curcumin Drugs 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 229960003530 donepezil Drugs 0.000 description 1
- 229940059082 douche Drugs 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 229940084238 eldepryl Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 229940108366 exelon Drugs 0.000 description 1
- 235000014089 extruded snacks Nutrition 0.000 description 1
- 210000001508 eye Anatomy 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 229960003980 galantamine Drugs 0.000 description 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960003627 gemfibrozil Drugs 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 235000003869 genetically modified organism Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000014168 granola/muesli bars Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 229940002661 lipitor Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229940063720 lopid Drugs 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 229960004640 memantine Drugs 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- 235000012459 muffins Nutrition 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000012771 pancakes Nutrition 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000003075 phytoestrogen Substances 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229960001109 policosanol Drugs 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
- 235000019684 potato crisps Nutrition 0.000 description 1
- 229940089484 pravachol Drugs 0.000 description 1
- 229960001495 pravastatin sodium Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000012434 pretzels Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000020991 processed meat Nutrition 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229960004136 rivastigmine Drugs 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 235000021491 salty snack Nutrition 0.000 description 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
- IYETZZCWLLUHIJ-UTONKHPSSA-N selegiline hydrochloride Chemical compound [Cl-].C#CC[NH+](C)[C@H](C)CC1=CC=CC=C1 IYETZZCWLLUHIJ-UTONKHPSSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- 235000009561 snack bars Nutrition 0.000 description 1
- 235000012177 snack cakes Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000021147 sweet food Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000006032 tissue transformation Effects 0.000 description 1
- 235000012776 toaster pastry Nutrition 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 229940072168 zocor Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94728407P | 2007-06-29 | 2007-06-29 | |
| PCT/US2008/068613 WO2009006317A1 (en) | 2007-06-29 | 2008-06-27 | Production and purification of esters of polyunsaturated fatty acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010532418A true JP2010532418A (ja) | 2010-10-07 |
| JP2010532418A5 JP2010532418A5 (OSRAM) | 2011-08-18 |
Family
ID=40226489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010515186A Pending JP2010532418A (ja) | 2007-06-29 | 2008-06-27 | 多価不飽和脂肪酸のエステルの製造方法および精製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US20090023808A1 (OSRAM) |
| EP (1) | EP2173699A4 (OSRAM) |
| JP (1) | JP2010532418A (OSRAM) |
| CN (1) | CN101796014A (OSRAM) |
| AU (2) | AU2008269989B2 (OSRAM) |
| CA (1) | CA2692355C (OSRAM) |
| MX (2) | MX374545B (OSRAM) |
| WO (1) | WO2009006317A1 (OSRAM) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013507454A (ja) * | 2009-10-13 | 2013-03-04 | マーテック バイオサイエンシーズ コーポレーション | 外傷性脳損傷の病理学的影響の危険を軽減する方法 |
| JP2014520574A (ja) * | 2011-07-21 | 2014-08-25 | ディーエスエム アイピー アセッツ ビー．ブイ． | 多価不飽和脂肪酸が高濃度化された微生物油 |
| JP2015063653A (ja) * | 2013-08-30 | 2015-04-09 | 備前化成株式会社 | 高純度オメガ３系脂肪酸エチルエステルの生産方法 |
| JPWO2015083806A1 (ja) * | 2013-12-04 | 2017-03-16 | 日本水産株式会社 | 微生物油、微生物油の製造方法、濃縮微生物油及び濃縮微生物油の製造方法 |
| KR101815110B1 (ko) | 2015-10-16 | 2018-01-10 | 에이케이 앤 엠엔 바이오팜 주식회사 | 오메가-7계 불포화 지방산의 정제공정 |
| KR20180048715A (ko) * | 2015-08-25 | 2018-05-10 | 디에스엠 아이피 어셋츠 비.브이. | 정제된 오일 조성물 및 제조 방법 |
| KR20180063217A (ko) * | 2015-10-05 | 2018-06-11 | 디에스엠 아이피 어셋츠 비.브이. | 오일 조성물 및 제조 방법 |
| RU2709620C1 (ru) * | 2019-07-01 | 2019-12-19 | Федеральное государственное автономное образовательное учреждение высшего образования "Новосибирский национальный исследовательский государственный университет" (Новосибирский государственный университет, НГУ) | Водная эмульсия на основе диметоксинитробензиловых эфиров арахидоновой кислоты |
| JP2020529397A (ja) * | 2017-08-07 | 2020-10-08 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | 濃縮多価不飽和脂肪酸オイルの製造プロセス |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070032548A1 (en) * | 2005-07-08 | 2007-02-08 | Ellis Lorie A | Polyunsaturated fatty acids for treatment of dementia and pre-dementia-related conditions |
| MX374545B (es) * | 2007-06-29 | 2025-03-06 | Dsm Ip Assets Bv | Produccion y purificacion de esteres de acidos grasos poliinsaturados. |
| US20090071064A1 (en) * | 2007-07-27 | 2009-03-19 | Machacek Mark T | Continuous algal biodiesel production facility |
| CN104042600A (zh) * | 2009-02-02 | 2014-09-17 | 帝斯曼知识产权资产有限公司 | 改善认知功能和降低心率的方法 |
| US20110177061A1 (en) | 2009-07-10 | 2011-07-21 | Martek Biosciences Corporation | Methods of treating and preventing neurological disorders using docosahexaenoic acid |
| DE102009038354B4 (de) * | 2009-08-21 | 2018-09-20 | Auto-Kabel Management Gmbh | Batteriepolklemme |
| US20110082205A1 (en) * | 2009-10-01 | 2011-04-07 | Panker Cynthia A | Docosahexaenoic Acid Gel Caps |
| US9247547B2 (en) * | 2009-10-15 | 2016-01-26 | Qualcomm Incorporated | Downlink and uplink resource element mapping for carrier extension |
| EP2519332B1 (en) | 2009-12-30 | 2014-03-05 | BASF Pharma (Callanish) Limited | Simulated moving bed chromatographic separation process for the purification of polyunsaturated fatty acids |
| WO2011097273A1 (en) * | 2010-02-02 | 2011-08-11 | Martek Biosciences Corporation | Methods and compositions for treating non-alcoholic fatty liver disease with docosahexaenoic acid and n-acetyl lcystenine |
| US8372465B2 (en) * | 2010-02-17 | 2013-02-12 | Bunge Oils, Inc. | Oil compositions of stearidonic acid |
| US9585837B2 (en) | 2010-04-09 | 2017-03-07 | Dsm Ip Assets B.V. | Thermally stable oil-in-water emulsions containing an oil that contains polyunsaturated fatty acids |
| US9023625B2 (en) | 2010-06-14 | 2015-05-05 | Io-Mega Holding Corporation | Methods for production of algae derived oils |
| DK2611767T3 (en) * | 2010-09-03 | 2017-12-11 | Stepan Specialty Products Llc | ELIMINATION OF ORGANO HALOGENE AND OXIRAN SPECIES IN CARBOXYLIC ACID ESTREAM |
| GB201111594D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New improved process |
| GB201111591D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Further new process |
| GB201111589D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New modified process |
| GB201111595D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Improved process |
| GB201111601D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New process |
| WO2013024174A1 (en) | 2011-08-18 | 2013-02-21 | Dsm Ip Assets B.V. | Dha triglyceride, dha free fatty acid, and dha ethyl ester emulsions, and methods of treating spinal cord injury |
| KR20200003227A (ko) | 2011-11-01 | 2020-01-08 | 디에스엠 아이피 어셋츠 비.브이. | 산화적으로 안정한 다중불포화된 지방산 함유 오일 |
| EP4205546A1 (en) | 2012-05-10 | 2023-07-05 | Solutex NA LLC | Oils with anti-inflammatory activity containing natural specialized proresolving mediators and their precursors |
| FR2991337B1 (fr) * | 2012-05-29 | 2016-09-02 | Roquette Freres | Procede continu d'enrichissement en esters ethyliques de dha d'une huile produite par des microalgues |
| GB201300354D0 (en) | 2013-01-09 | 2013-02-20 | Basf Pharma Callanish Ltd | Multi-step separation process |
| ES2944869T3 (es) * | 2013-03-13 | 2023-06-26 | Dsm Nutritional Products Ag | Recuperación de urea y aceite de un complejo urea/aceite |
| WO2014152283A1 (en) | 2013-03-15 | 2014-09-25 | Heliae Development, Llc | Direct transesterification of algal biomass for synthesis of fatty acid ethyl esters (faee) |
| US9428711B2 (en) | 2013-05-07 | 2016-08-30 | Groupe Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| US8802880B1 (en) | 2013-05-07 | 2014-08-12 | Group Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| EP3118186B1 (fr) | 2013-12-11 | 2022-02-09 | Novasep Process | Installation chromatographique de production d acides gras polyinsatures |
| FR3014436B1 (fr) * | 2013-12-11 | 2016-10-21 | Novasep Process | Procede de purification chromatographique d'un acide gras |
| US10975031B2 (en) | 2014-01-07 | 2021-04-13 | Novasep Process | Method for purifying aromatic amino acids |
| CN105779123B (zh) * | 2014-08-06 | 2020-03-10 | 石家庄搏澳增塑材料科技有限公司 | 氯化胆碱法解包尿素-饱和脂肪酸甲酯包合物的清洁工艺 |
| CN105566103B (zh) * | 2014-10-13 | 2019-02-19 | 浙江医药股份有限公司新昌制药厂 | 一种甘油酯型多不饱和脂肪酸的制备方法 |
| CN107709528A (zh) * | 2015-05-13 | 2018-02-16 | 艾帕克斯挪威联合股份有限公司 | 来自天然油的非常长链多不饱和脂肪酸 |
| WO2017041094A1 (en) | 2015-09-03 | 2017-03-09 | Solutex Na Llc | Compositions comprising omega-3 fatty acids, 17-hdha and 18- hepe and methods of using same |
| KR102405390B1 (ko) | 2016-07-13 | 2022-06-03 | 에보닉 오퍼레이션스 게엠베하 | 용해된 지질을 함유하는 바이오매스로부터 지질을 분리하는 방법 |
| DK3562925T3 (da) | 2016-12-27 | 2021-05-25 | Evonik Operations Gmbh | Fremgangsmåde til isolering af lipider fra en lipidholdig biomasse |
| EP3470502A1 (en) | 2017-10-13 | 2019-04-17 | Evonik Degussa GmbH | Method of separating lipids from a lysed lipids containing biomass |
| EP3527664A1 (en) | 2018-02-15 | 2019-08-21 | Evonik Degussa GmbH | Method of isolating lipids from a lipids containing biomass |
| CN112166176B (zh) | 2018-05-15 | 2024-06-25 | 赢创运营有限公司 | 借助疏水性二氧化硅从含有脂质的生物质中分离脂质的方法 |
| BR112020023222A2 (pt) | 2018-05-15 | 2021-03-23 | Evonik Operations Gmbh | método de isolamento de lipídios a partir de uma biomassa contendo lipídios lisados por inversão por emulsão |
| EP3586643A1 (en) * | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| EP3586641A1 (en) * | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| EP3586642A1 (en) | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Ala enriched polyunsaturated fatty acid compositions |
| EP3586640A1 (en) * | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| CN109061000A (zh) * | 2018-09-13 | 2018-12-21 | 中国科学院海洋研究所 | 一种衍生化处理植物油脂的混合液及其衍生化方法和应用 |
| CN109337939B (zh) * | 2018-09-30 | 2021-07-27 | 河北康睿达脂质有限公司 | 一种多不饱和脂肪酸结构脂质的制备方法 |
| NO20181574A1 (en) * | 2018-12-06 | 2020-06-08 | Epax Norway As | Very long chain fatty acids |
| HUE059207T2 (hu) * | 2018-12-12 | 2022-11-28 | Nippon Suisan Kaisha Ltd | Nagymértékben telítetlen zsírsavat vagy alkil-észterét tartalmazó készítmény és eljárás elõállítására |
| FR3108622B1 (fr) | 2020-03-27 | 2024-08-23 | Polaris | Procédé de fractionnement d’acides gras à deux carbones de différence par distillation moléculaire |
| LU102019B1 (de) * | 2020-08-26 | 2022-02-28 | K D Pharma Bexbach Gmbh | Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis |
| WO2025114579A2 (en) | 2023-12-01 | 2025-06-05 | Tate & Lyle Solutions Usa Llc | Methods of processing an oil composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003500082A (ja) * | 1999-05-31 | 2003-01-07 | ジェイ・エフ・エス インバイロヘルス リミテッド | 蒸留−酵素的エステル交換の組合せによるポリ不飽和脂肪酸エステルの濃縮及び精製 |
| JP2006305569A (ja) * | 2002-06-18 | 2006-11-09 | Martek Biosciences Corp | 水溶液中の油の安定エマルジョンおよびその製造方法 |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3082228A (en) * | 1959-12-18 | 1963-03-19 | Escambia Chem Corp | Method for producing monoesters of polyunsaturated fatty acids |
| NL8300698A (nl) * | 1983-02-24 | 1984-09-17 | Univ Leiden | Werkwijze voor het inbouwen van vreemd dna in het genoom van tweezaadlobbige planten; agrobacterium tumefaciens bacterien en werkwijze voor het produceren daarvan; planten en plantecellen met gewijzigde genetische eigenschappen; werkwijze voor het bereiden van chemische en/of farmaceutische produkten. |
| IT1205043B (it) * | 1987-05-28 | 1989-03-10 | Innova Di Ridolfi Flora & C S | Procedimento per l'estrazione di esteri di acidi grassi poliinsaturi da olii di pesce e composizioni farmaceutiche e dietetiche contenenti detti esteri |
| GB2218984B (en) * | 1988-05-27 | 1992-09-23 | Renafield Limited | Process for preparing high-concentration mixtures of polyunsaturated fatty acids & their esters and their prophylactic or therapeutic uses |
| GB8819110D0 (en) * | 1988-08-11 | 1988-09-14 | Norsk Hydro As | Antihypertensive drug & method for production |
| US5340594A (en) * | 1988-09-07 | 1994-08-23 | Omegatech Inc. | Food product having high concentrations of omega-3 highly unsaturated fatty acids |
| US5130242A (en) * | 1988-09-07 | 1992-07-14 | Phycotech, Inc. | Process for the heterotrophic production of microbial products with high concentrations of omega-3 highly unsaturated fatty acids |
| US5340742A (en) * | 1988-09-07 | 1994-08-23 | Omegatech Inc. | Process for growing thraustochytrium and schizochytrium using non-chloride salts to produce a microfloral biomass having omega-3-highly unsaturated fatty acids |
| US5407957A (en) * | 1990-02-13 | 1995-04-18 | Martek Corporation | Production of docosahexaenoic acid by dinoflagellates |
| US5658767A (en) * | 1991-01-24 | 1997-08-19 | Martek Corporation | Arachidonic acid and methods for the production and use thereof |
| US5436269A (en) * | 1991-11-14 | 1995-07-25 | Sagami Chemical Research Center | Method for treating hepatitis |
| GB9205880D0 (en) * | 1992-03-18 | 1992-04-29 | Hoffmann La Roche | Low energy pufa enrichment |
| ATE181745T1 (de) * | 1994-08-16 | 1999-07-15 | Frische Gmbh | Verfahren zur gewinnung von nicht wasserlöslichen, nativen produkten aus nativen stoffgemengen mit hilfe der zentrifugalkraft |
| EP2213750A1 (en) * | 1996-07-23 | 2010-08-04 | Nagase ChemteX Corporation | Process for preparing docosahexaenoic acid and docosapentaenoic acid |
| CA2283422A1 (en) * | 1997-06-04 | 1998-12-10 | Calgene, Llc | Production of polyunsaturated fatty acids by expression of polyketide-like synthesis genes in plants |
| US6566583B1 (en) * | 1997-06-04 | 2003-05-20 | Daniel Facciotti | Schizochytrium PKS genes |
| CN1204638A (zh) * | 1997-07-02 | 1999-01-13 | 湖南天海林实业股份有限公司 | 二十二碳六烯酸的制备和酯化工艺 |
| US6677145B2 (en) * | 1998-09-02 | 2004-01-13 | Abbott Laboratories | Elongase genes and uses thereof |
| US7271315B2 (en) * | 1999-01-14 | 2007-09-18 | Martek Biosciences Corporation | PUFA polyketide synthase systems and uses thereof |
| US7247461B2 (en) * | 1999-01-14 | 2007-07-24 | Martek Biosciences Corporation | Nucleic acid molecule encoding ORFA of a PUFA polyketide synthase system and uses thereof |
| US7217856B2 (en) * | 1999-01-14 | 2007-05-15 | Martek Biosciences Corporation | PUFA polyketide synthase systems and uses thereof |
| US7211418B2 (en) * | 1999-01-14 | 2007-05-01 | Martek Biosciences Corporation | PUFA polyketide synthase systems and uses thereof |
| EP1196518B1 (en) * | 1999-02-26 | 2004-08-11 | Martek Biosciences Corporation | Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides |
| CA2311974A1 (en) * | 1999-06-28 | 2000-12-28 | Nisshin Flour Milling Co., Ltd. | Processes of selectively separating and purifying eicosapentaenoic and docosahexaenoic acids or their esters |
| US6712867B1 (en) * | 1999-08-18 | 2004-03-30 | Biox Corporation | Process for production of fatty acid methyl esters from fatty acid triglycerides |
| US6395778B1 (en) * | 2000-01-11 | 2002-05-28 | Omegatech, Inc. | Process for making an enriched mixture of polyunsaturated fatty acid esters |
| EP2295595B1 (en) * | 2000-01-19 | 2019-05-01 | DSM IP Assets B.V. | Solventless extraction process |
| CN101519678B (zh) * | 2000-01-28 | 2013-11-13 | Dsmip资产公司 | 通过在发酵罐中高密度培养真核微生物来增加含有多烯脂肪酸的脂质的产生 |
| EP1178103A1 (en) * | 2000-08-02 | 2002-02-06 | Dsm N.V. | Purifying crude pufa oils |
| TWI377253B (en) * | 2001-04-16 | 2012-11-21 | Martek Biosciences Corp | Product and process for transformation of thraustochytriales microorganisms |
| DE10224937A1 (de) * | 2001-06-05 | 2002-12-12 | Celanese Ventures Gmbh | Festphasen-Extraktionsverfahren zur Gewinnung hochreiner ungesättigter Verbindungen bzw. Derivate dieser Verbindungen |
| US20030032826A1 (en) * | 2001-07-20 | 2003-02-13 | The Board Of Regents Of The University Of Nebraska | Transesterification process for production of biodiesel |
| JP2003048831A (ja) * | 2001-08-02 | 2003-02-21 | Suntory Ltd | 脳機能の低下に起因する症状あるいは疾患の予防又は改善作用を有する組成物 |
| DE10151155A1 (de) * | 2001-10-19 | 2003-05-08 | Nutrinova Gmbh | Native PUFA-Triglyceridmischungen mit einem hohen Gehalt an mehrfach ungesättigten Fettsäuren sowie Verfahren zu deren Herstellung und deren Verwendung |
| KR100556337B1 (ko) * | 2002-02-05 | 2006-03-03 | 주식회사 가야에너지 | 단일단계 연속공정을 통한 고순도 지방산 알킬에스테르의제조방법 |
| ES2774656T3 (es) * | 2002-05-03 | 2020-07-22 | Dsm Ip Assets Bv | Métodos para producir lípidos de alta calidad mediante liberación enzimática desde biomasa |
| DK1542670T3 (da) * | 2002-09-24 | 2013-05-27 | Suntory Holdings Ltd | Sammensætning omfattende arachidonsyre alene eller i kombination med docosahexanoensyre til forøgelse af kognitive evner hos voksne |
| EP2283838A3 (en) * | 2002-09-27 | 2011-04-20 | Martek Biosciences Corporation | Docosahexaenoic acid for treating subclinical inflammation |
| US20040172682A1 (en) * | 2003-02-12 | 2004-09-02 | Kinney Anthony J. | Production of very long chain polyunsaturated fatty acids in oilseed plants |
| BRPI0408563A (pt) * | 2003-03-20 | 2006-03-21 | Michael F Pelly | processo e aparelho para refino de biodiesel |
| CN1208308C (zh) * | 2003-05-08 | 2005-06-29 | 南京大学 | 从卤虾粉提取、制备、纯化二十二碳六烯酸乙酯的方法 |
| US7208590B2 (en) * | 2003-07-15 | 2007-04-24 | Abbott Laboratories | Genes involved in polyketide synthase pathways and uses thereof |
| KR20060081714A (ko) * | 2003-10-02 | 2006-07-13 | 미시시피 주립대학 | 폐수 처리 플랜트 슬러지로부터의 바이오-디젤 및 다른귀중한 화학물질의 제조방법 |
| US7169946B1 (en) * | 2004-03-05 | 2007-01-30 | Twin Rivers Technologies, L.P. | Alternatives to distilled oleo chemicals in derivatives and production thereof |
| JP2008516890A (ja) * | 2004-08-06 | 2008-05-22 | トランスフオーム・フアーマシユーチカルズ・インコーポレーテツド | 新規なフェノフィブラート製剤および関連治療方法 |
| US7666234B2 (en) * | 2004-10-20 | 2010-02-23 | Council Of Scientific And Industrial Research | Process for the preparation of fatty acid methyl ester from triglyceride oil by transesterification |
| DE102005003624A1 (de) * | 2005-01-26 | 2006-07-27 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Herstellung und Anwendung eines antioxidativ wirksamen Extraktes aus Crypthecodinium sp. |
| WO2006133437A1 (en) * | 2005-06-09 | 2006-12-14 | Biosphere Environmental Energy Llc | Systems and methods for esterification and transesterification of fats and oils |
| MX374545B (es) * | 2007-06-29 | 2025-03-06 | Dsm Ip Assets Bv | Produccion y purificacion de esteres de acidos grasos poliinsaturados. |
-
2008
- 2008-06-27 MX MX2015006380A patent/MX374545B/es unknown
- 2008-06-27 AU AU2008269989A patent/AU2008269989B2/en not_active Ceased
- 2008-06-27 MX MX2010000263A patent/MX2010000263A/es active IP Right Grant
- 2008-06-27 CN CN200880104965A patent/CN101796014A/zh active Pending
- 2008-06-27 WO PCT/US2008/068613 patent/WO2009006317A1/en not_active Ceased
- 2008-06-27 CA CA2692355A patent/CA2692355C/en active Active
- 2008-06-27 US US12/163,555 patent/US20090023808A1/en not_active Abandoned
- 2008-06-27 JP JP2010515186A patent/JP2010532418A/ja active Pending
- 2008-06-27 EP EP08781103.0A patent/EP2173699A4/en not_active Ceased
-
2009
- 2009-12-29 US US12/649,178 patent/US20110098356A1/en not_active Abandoned
-
2014
- 2014-01-13 US US14/154,140 patent/US9796658B2/en not_active Expired - Fee Related
- 2014-05-27 AU AU2014202880A patent/AU2014202880B2/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003500082A (ja) * | 1999-05-31 | 2003-01-07 | ジェイ・エフ・エス インバイロヘルス リミテッド | 蒸留−酵素的エステル交換の組合せによるポリ不飽和脂肪酸エステルの濃縮及び精製 |
| JP2006305569A (ja) * | 2002-06-18 | 2006-11-09 | Martek Biosciences Corp | 水溶液中の油の安定エマルジョンおよびその製造方法 |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013507454A (ja) * | 2009-10-13 | 2013-03-04 | マーテック バイオサイエンシーズ コーポレーション | 外傷性脳損傷の病理学的影響の危険を軽減する方法 |
| JP2016053065A (ja) * | 2009-10-13 | 2016-04-14 | ディーエスエム アイピー アセッツ ビー．ブイ． | 外傷性脳損傷の病理学的影響の危険を軽減する方法 |
| JP2018021067A (ja) * | 2009-10-13 | 2018-02-08 | ディーエスエム アイピー アセッツ ビー．ブイ． | 外傷性脳損傷の病理学的影響の危険を軽減する方法 |
| JP2014520574A (ja) * | 2011-07-21 | 2014-08-25 | ディーエスエム アイピー アセッツ ビー．ブイ． | 多価不飽和脂肪酸が高濃度化された微生物油 |
| JP2015063653A (ja) * | 2013-08-30 | 2015-04-09 | 備前化成株式会社 | 高純度オメガ３系脂肪酸エチルエステルの生産方法 |
| US10750741B2 (en) | 2013-12-04 | 2020-08-25 | Nippon Suisan Kaisha, Ltd. | Dihomo-γ-linolenic acid-containing microbial oil and dihomo-γ-linolenic acid-containing microbial biomass |
| JPWO2015083806A1 (ja) * | 2013-12-04 | 2017-03-16 | 日本水産株式会社 | 微生物油、微生物油の製造方法、濃縮微生物油及び濃縮微生物油の製造方法 |
| JP2019216745A (ja) * | 2013-12-04 | 2019-12-26 | 日本水産株式会社 | 微生物油、微生物油の製造方法、濃縮微生物油及び濃縮微生物油の製造方法 |
| JP7446386B2 (ja) | 2013-12-04 | 2024-03-08 | 株式会社ニッスイ | 微生物油、微生物油の製造方法、濃縮微生物油及び濃縮微生物油の製造方法 |
| US11330817B2 (en) | 2013-12-04 | 2022-05-17 | Nippon Suisan Kaisha, Ltd. | Microbial oil, production method for microbial oil, concentrated microbial oil, and production method for concentrated microbial oil |
| JP2023001211A (ja) * | 2013-12-04 | 2023-01-04 | 株式会社ニッスイ | 微生物油、微生物油の製造方法、濃縮微生物油及び濃縮微生物油の製造方法 |
| US11856952B2 (en) | 2013-12-04 | 2024-01-02 | Nippon Suisan Kaisha, Ltd. | Microbial oil, production method for microbial oil, concentrated microbial oil, and production method for concentrated microbial oil |
| KR20180048715A (ko) * | 2015-08-25 | 2018-05-10 | 디에스엠 아이피 어셋츠 비.브이. | 정제된 오일 조성물 및 제조 방법 |
| KR102716618B1 (ko) * | 2015-08-25 | 2024-10-14 | 디에스엠 아이피 어셋츠 비.브이. | 정제된 오일 조성물 및 제조 방법 |
| KR20180063217A (ko) * | 2015-10-05 | 2018-06-11 | 디에스엠 아이피 어셋츠 비.브이. | 오일 조성물 및 제조 방법 |
| JP2018532015A (ja) * | 2015-10-05 | 2018-11-01 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | 油組成物および製造方法 |
| KR102728376B1 (ko) * | 2015-10-05 | 2024-11-11 | 디에스엠 아이피 어셋츠 비.브이. | 오일 조성물 및 제조 방법 |
| KR101815110B1 (ko) | 2015-10-16 | 2018-01-10 | 에이케이 앤 엠엔 바이오팜 주식회사 | 오메가-7계 불포화 지방산의 정제공정 |
| JP2020529397A (ja) * | 2017-08-07 | 2020-10-08 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | 濃縮多価不飽和脂肪酸オイルの製造プロセス |
| RU2709620C1 (ru) * | 2019-07-01 | 2019-12-19 | Федеральное государственное автономное образовательное учреждение высшего образования "Новосибирский национальный исследовательский государственный университет" (Новосибирский государственный университет, НГУ) | Водная эмульсия на основе диметоксинитробензиловых эфиров арахидоновой кислоты |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2692355C (en) | 2018-09-11 |
| US20140128465A1 (en) | 2014-05-08 |
| US9796658B2 (en) | 2017-10-24 |
| WO2009006317A1 (en) | 2009-01-08 |
| AU2008269989B2 (en) | 2014-02-27 |
| EP2173699A4 (en) | 2014-04-16 |
| CN101796014A (zh) | 2010-08-04 |
| MX2010000263A (es) | 2010-03-11 |
| MX374545B (es) | 2025-03-06 |
| CA2692355A1 (en) | 2009-01-08 |
| US20110098356A1 (en) | 2011-04-28 |
| AU2008269989A1 (en) | 2009-01-08 |
| AU2014202880A1 (en) | 2014-06-19 |
| AU2014202880B2 (en) | 2017-08-31 |
| US20090023808A1 (en) | 2009-01-22 |
| EP2173699A1 (en) | 2010-04-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2692355C (en) | Production and purification of esters of polyunsaturated fatty acids | |
| ES2857173T3 (es) | Aceites microbianos enriquecidos en ácidos grasos poliinsaturados | |
| EP2630869B1 (en) | Polyunsaturated fatty acid-containing oil product and uses and production thereof | |
| JP4518674B2 (ja) | ドコサペンタエン酸含有物質の利用 | |
| AU2008293423B2 (en) | Polyunsaturated fatty acid-containing solid fat compositions and uses and production thereof | |
| CN113438948A (zh) | 极长链脂肪酸组合物 | |
| WO2011053892A1 (en) | Synthesis and use of omega-3 and omega-6 very long chain polyunsaturated fatty acids (vlc-pufa) | |
| WO2012112902A1 (en) | Methods of preparing free polyunsaturated fatty acids | |
| HK1147086A (en) | Production and purification of esters of polyunsaturated fatty acids | |
| HK1198544B (en) | Microbial oils enriched in polyunsaturated fatty acids | |
| AU2015200426A1 (en) | Polyunsaturated fatty acid-containing solid fat compositions and uses and production thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110623 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110623 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20121225 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130116 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130405 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130412 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20130510 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20130510 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130925 |