WO2010149759A1 - Microparticles comprising a fat soluble fraction comprising dha and their production - Google Patents
Microparticles comprising a fat soluble fraction comprising dha and their production Download PDFInfo
- Publication number
- WO2010149759A1 WO2010149759A1 PCT/EP2010/059038 EP2010059038W WO2010149759A1 WO 2010149759 A1 WO2010149759 A1 WO 2010149759A1 EP 2010059038 W EP2010059038 W EP 2010059038W WO 2010149759 A1 WO2010149759 A1 WO 2010149759A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- microparticle
- soluble fraction
- total amount
- moieties
- fat soluble
- Prior art date
Links
- 239000011859 microparticle Substances 0.000 title claims abstract description 164
- 238000004519 manufacturing process Methods 0.000 title abstract description 16
- 235000019197 fats Nutrition 0.000 claims abstract description 144
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical group 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 abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000005471 saturated fatty acid group Chemical group 0.000 claims abstract 3
- 239000003921 oil Substances 0.000 claims description 105
- 235000019198 oils Nutrition 0.000 claims description 105
- 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 49
- 239000012141 concentrate Substances 0.000 claims description 46
- 235000008504 concentrate Nutrition 0.000 claims description 46
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 36
- 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 35
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 33
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 32
- 239000011159 matrix material Substances 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 27
- 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 25
- 239000000203 mixture Substances 0.000 claims description 24
- 239000000839 emulsion Substances 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 150000004665 fatty acids Chemical group 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 229940071162 caseinate Drugs 0.000 claims description 19
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 14
- 229960004488 linolenic acid Drugs 0.000 claims description 14
- 239000000416 hydrocolloid Substances 0.000 claims description 13
- 229930006000 Sucrose Natural products 0.000 claims description 12
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 12
- 235000021342 arachidonic acid Nutrition 0.000 claims description 12
- 229940114079 arachidonic acid Drugs 0.000 claims description 12
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 12
- 229960004793 sucrose Drugs 0.000 claims description 12
- 150000003626 triacylglycerols Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 11
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 11
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims description 11
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims description 11
- 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 11
- 229960002733 gamolenic acid Drugs 0.000 claims description 11
- DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical group CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 claims description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 11
- 235000021323 fish oil Nutrition 0.000 claims description 10
- 239000004014 plasticizer Substances 0.000 claims description 10
- 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 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 235000006708 antioxidants Nutrition 0.000 claims description 8
- 238000007257 deesterification reaction Methods 0.000 claims description 8
- 235000013681 dietary sucrose Nutrition 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000001694 spray drying Methods 0.000 claims description 8
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical group CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 7
- 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 claims description 7
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims description 7
- 235000016709 nutrition Nutrition 0.000 claims description 7
- 239000007764 o/w emulsion Substances 0.000 claims description 7
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 7
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 7
- 229960005055 sodium ascorbate Drugs 0.000 claims description 7
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 7
- 229930003799 tocopherol Natural products 0.000 claims description 7
- 239000011732 tocopherol Substances 0.000 claims description 7
- 244000215068 Acacia senegal Species 0.000 claims description 6
- 229920000084 Gum arabic Polymers 0.000 claims description 6
- 229920002472 Starch Polymers 0.000 claims description 6
- 235000010489 acacia gum Nutrition 0.000 claims description 6
- 239000001506 calcium phosphate Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 150000004676 glycans Chemical class 0.000 claims description 6
- 229920001282 polysaccharide Polymers 0.000 claims description 6
- 239000005017 polysaccharide Substances 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 235000019698 starch Nutrition 0.000 claims description 6
- 239000008107 starch Substances 0.000 claims description 6
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 6
- 235000019731 tricalcium phosphate Nutrition 0.000 claims description 6
- 229940078499 tricalcium phosphate Drugs 0.000 claims description 6
- 229910000391 tricalcium phosphate Inorganic materials 0.000 claims description 6
- 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 claims description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 5
- 239000004368 Modified starch Substances 0.000 claims description 5
- 229920000881 Modified starch Polymers 0.000 claims description 5
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 239000008101 lactose Substances 0.000 claims description 5
- 239000000787 lecithin Substances 0.000 claims description 5
- 235000010445 lecithin Nutrition 0.000 claims description 5
- 229940067606 lecithin Drugs 0.000 claims description 5
- 235000019426 modified starch Nutrition 0.000 claims description 5
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 5
- 235000010935 mono and diglycerides of fatty acids Nutrition 0.000 claims description 5
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 5
- 235000010384 tocopherol Nutrition 0.000 claims description 5
- 229960001295 tocopherol Drugs 0.000 claims description 5
- 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 claims description 5
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 4
- 235000006491 Acacia senegal Nutrition 0.000 claims description 4
- 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 4
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 4
- 229920001353 Dextrin Polymers 0.000 claims description 4
- 239000004375 Dextrin Substances 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 239000005913 Maltodextrin Substances 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004373 Pullulan Substances 0.000 claims description 4
- 229920001218 Pullulan Polymers 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 4
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 4
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 4
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 4
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 4
- 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 claims description 4
- 235000019425 dextrin Nutrition 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 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 4
- -1 invert sugar Substances 0.000 claims description 4
- 229940035034 maltodextrin Drugs 0.000 claims description 4
- 230000035764 nutrition Effects 0.000 claims description 4
- 235000010987 pectin Nutrition 0.000 claims description 4
- 239000001814 pectin Substances 0.000 claims description 4
- 229920001277 pectin Polymers 0.000 claims description 4
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 claims description 4
- 235000019423 pullulan Nutrition 0.000 claims description 4
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 claims description 4
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 claims description 3
- 239000005715 Fructose Substances 0.000 claims description 3
- 229920002774 Maltodextrin Polymers 0.000 claims description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000006188 syrup Substances 0.000 claims description 3
- 235000020357 syrup Nutrition 0.000 claims description 3
- DMASLKHVQRHNES-UPOGUZCLSA-N (3R)-beta,beta-caroten-3-ol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C DMASLKHVQRHNES-UPOGUZCLSA-N 0.000 claims description 2
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 claims description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 2
- YBVRFTBNIZWMSK-UHFFFAOYSA-N 2,2-dimethyl-1-phenylpropan-1-ol Chemical compound CC(C)(C)C(O)C1=CC=CC=C1 YBVRFTBNIZWMSK-UHFFFAOYSA-N 0.000 claims description 2
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 2
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 claims description 2
- 239000004217 Citranaxanthin Substances 0.000 claims description 2
- SLQHGWZKKZPZEK-JKEZLOPUSA-N Citranaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)C)C=CC=C(/C)C=CC1=C(C)CCCC1(C)C SLQHGWZKKZPZEK-JKEZLOPUSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 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 2
- 239000001692 EU approved anti-caking agent Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 239000001828 Gelatine Substances 0.000 claims description 2
- 235000013628 Lantana involucrata Nutrition 0.000 claims description 2
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 claims description 2
- JEVVKJMRZMXFBT-XWDZUXABSA-N Lycophyll Natural products OC/C(=C/CC/C(=C\C=C\C(=C/C=C/C(=C\C=C\C=C(/C=C/C=C(\C=C\C=C(/CC/C=C(/CO)\C)\C)/C)\C)/C)\C)/C)/C JEVVKJMRZMXFBT-XWDZUXABSA-N 0.000 claims description 2
- ABSPRNADVQNDOU-UHFFFAOYSA-N Menaquinone 1 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(C)C(=O)C2=C1 ABSPRNADVQNDOU-UHFFFAOYSA-N 0.000 claims description 2
- 102000014171 Milk Proteins Human genes 0.000 claims description 2
- 108010011756 Milk Proteins Proteins 0.000 claims description 2
- 235000006677 Monarda citriodora ssp. austromontana Nutrition 0.000 claims description 2
- 240000007673 Origanum vulgare Species 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 244000178231 Rosmarinus officinalis Species 0.000 claims description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 2
- 229930003316 Vitamin D Natural products 0.000 claims description 2
- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 229930003448 Vitamin K Natural products 0.000 claims description 2
- 108010046377 Whey Proteins Proteins 0.000 claims description 2
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 claims description 2
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 claims description 2
- 239000000205 acacia gum Substances 0.000 claims description 2
- 229940072056 alginate Drugs 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 claims description 2
- NBZANZVJRKXVBH-ITUXNECMSA-N all-trans-alpha-cryptoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CCCC2(C)C)C NBZANZVJRKXVBH-ITUXNECMSA-N 0.000 claims description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 2
- 229940115440 aluminum sodium silicate Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 235000013793 astaxanthin Nutrition 0.000 claims description 2
- 239000001168 astaxanthin Substances 0.000 claims description 2
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 claims description 2
- 229940022405 astaxanthin Drugs 0.000 claims description 2
- 150000004054 benzoquinones Chemical class 0.000 claims description 2
- 235000013734 beta-carotene Nutrition 0.000 claims description 2
- 235000002360 beta-cryptoxanthin Nutrition 0.000 claims description 2
- 239000011774 beta-cryptoxanthin Substances 0.000 claims description 2
- DMASLKHVQRHNES-ITUXNECMSA-N beta-cryptoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CCCC2(C)C DMASLKHVQRHNES-ITUXNECMSA-N 0.000 claims description 2
- 235000013361 beverage Nutrition 0.000 claims description 2
- 235000012682 canthaxanthin Nutrition 0.000 claims description 2
- FDSDTBUPSURDBL-DKLMTRRASA-N canthaxanthin Chemical compound CC=1C(=O)CCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C FDSDTBUPSURDBL-DKLMTRRASA-N 0.000 claims description 2
- 235000021466 carotenoid Nutrition 0.000 claims description 2
- 150000001747 carotenoids Chemical class 0.000 claims description 2
- 235000010418 carrageenan Nutrition 0.000 claims description 2
- 239000000679 carrageenan Substances 0.000 claims description 2
- 229920001525 carrageenan Polymers 0.000 claims description 2
- 229940113118 carrageenan Drugs 0.000 claims description 2
- 235000019247 citranaxanthin Nutrition 0.000 claims description 2
- PRDJTOVRIHGKNU-ZWERVMMHSA-N citranaxanthin Chemical compound CC(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C PRDJTOVRIHGKNU-ZWERVMMHSA-N 0.000 claims description 2
- PRDJTOVRIHGKNU-UHFFFAOYSA-N citranaxanthine Natural products CC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C PRDJTOVRIHGKNU-UHFFFAOYSA-N 0.000 claims description 2
- 229960004106 citric acid Drugs 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 229940110767 coenzyme Q10 Drugs 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- 235000012754 curcumin Nutrition 0.000 claims description 2
- 239000004148 curcumin Substances 0.000 claims description 2
- 229940109262 curcumin Drugs 0.000 claims description 2
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 claims description 2
- 235000015872 dietary supplement Nutrition 0.000 claims description 2
- 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 claims description 2
- 229960002061 ergocalciferol Drugs 0.000 claims description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000006052 feed supplement Substances 0.000 claims description 2
- 235000010382 gamma-tocopherol Nutrition 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 229960004903 invert sugar Drugs 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 235000012680 lutein Nutrition 0.000 claims description 2
- 239000001656 lutein Substances 0.000 claims description 2
- 229960005375 lutein Drugs 0.000 claims description 2
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 claims description 2
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 claims description 2
- 235000012661 lycopene Nutrition 0.000 claims description 2
- 239000001751 lycopene Substances 0.000 claims description 2
- 229960004999 lycopene Drugs 0.000 claims description 2
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 claims description 2
- 235000021239 milk protein Nutrition 0.000 claims description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 claims description 2
- 235000019175 phylloquinone Nutrition 0.000 claims description 2
- 239000011772 phylloquinone Substances 0.000 claims description 2
- MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 claims description 2
- 229960001898 phytomenadione Drugs 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 235000010388 propyl gallate Nutrition 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- 239000000429 sodium aluminium silicate Substances 0.000 claims description 2
- 235000012217 sodium aluminium silicate Nutrition 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 2
- 229960001790 sodium citrate Drugs 0.000 claims description 2
- 235000011083 sodium citrates Nutrition 0.000 claims description 2
- XDLYMKFUPYZCMA-UHFFFAOYSA-M sodium;4-oct-1-enoxy-4-oxobutanoate Chemical compound [Na+].CCCCCCC=COC(=O)CCC([O-])=O XDLYMKFUPYZCMA-UHFFFAOYSA-M 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000001959 sucrose esters of fatty acids Substances 0.000 claims description 2
- 235000010965 sucrose esters of fatty acids Nutrition 0.000 claims description 2
- 229940042585 tocopherol acetate Drugs 0.000 claims description 2
- 235000019149 tocopherols Nutrition 0.000 claims description 2
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 claims description 2
- 229960004747 ubidecarenone Drugs 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 235000019155 vitamin A Nutrition 0.000 claims description 2
- 239000011719 vitamin A Substances 0.000 claims description 2
- 235000019166 vitamin D Nutrition 0.000 claims description 2
- 239000011710 vitamin D Substances 0.000 claims description 2
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 2
- 235000001892 vitamin D2 Nutrition 0.000 claims description 2
- 239000011653 vitamin D2 Substances 0.000 claims description 2
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 claims description 2
- 235000005282 vitamin D3 Nutrition 0.000 claims description 2
- 239000011647 vitamin D3 Substances 0.000 claims description 2
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 235000019168 vitamin K Nutrition 0.000 claims description 2
- 239000011712 vitamin K Substances 0.000 claims description 2
- 150000003721 vitamin K derivatives Chemical class 0.000 claims description 2
- 229940045997 vitamin a Drugs 0.000 claims description 2
- 229940046008 vitamin d Drugs 0.000 claims description 2
- 229940021056 vitamin d3 Drugs 0.000 claims description 2
- 229940046010 vitamin k Drugs 0.000 claims description 2
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 claims description 2
- 235000010930 zeaxanthin Nutrition 0.000 claims description 2
- 239000001775 zeaxanthin Substances 0.000 claims description 2
- 229940043269 zeaxanthin Drugs 0.000 claims description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 claims description 2
- 239000002478 γ-tocopherol Substances 0.000 claims description 2
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 2
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 claims description 2
- 240000003183 Manihot esculenta Species 0.000 claims 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 108010009736 Protein Hydrolysates Proteins 0.000 claims 1
- 244000061456 Solanum tuberosum Species 0.000 claims 1
- 235000002595 Solanum tuberosum Nutrition 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 102000007544 Whey Proteins Human genes 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 235000009973 maize Nutrition 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 235000021119 whey protein Nutrition 0.000 claims 1
- 239000003925 fat Substances 0.000 description 125
- 150000004671 saturated fatty acids Chemical group 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 235000003441 saturated fatty acids Nutrition 0.000 description 7
- 125000005313 fatty acid group Chemical group 0.000 description 6
- AOHAPDDBNAPPIN-UHFFFAOYSA-N myristicinic acid Natural products COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 6
- 229940012843 omega-3 fatty acid Drugs 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 235000021588 free fatty acids Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 229940013317 fish oils Drugs 0.000 description 4
- 235000013350 formula milk Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- 239000006014 omega-3 oil Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 238000000265 homogenisation Methods 0.000 description 3
- 235000021125 infant nutrition Nutrition 0.000 description 3
- 229960001375 lactose Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 2
- 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 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960001031 glucose Drugs 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 229960002160 maltose Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LGHXTTIAZFVCCU-SSVNFBSYSA-N (2E,4E,6E,8E)-octadeca-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O LGHXTTIAZFVCCU-SSVNFBSYSA-N 0.000 description 1
- ZUUFLXSNVWQOJW-MBIXAETLSA-N (2e,4e,6e)-octadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C(O)=O ZUUFLXSNVWQOJW-MBIXAETLSA-N 0.000 description 1
- 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 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 102000011632 Caseins Human genes 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 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 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 1
- HQPCSDADVLFHHO-LTKCOYKYSA-N all-cis-8,11,14,17-icosatetraenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HQPCSDADVLFHHO-LTKCOYKYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009704 beneficial physiological effect Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 1
- 229940033080 omega-6 fatty acid Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
- A23D9/05—Forming free-flowing pieces
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to microparticles comprising a docosahexaenoic acid moiety having a low content of saturated fatty acid moieties and a low content of free surface fat.
- the invention further relates to uses of such microparticles, methods of their manufacture and products comprising the microparticles.
- compositions comprising significant amounts of highly unsaturated fatty acids have frequently been shown to possess valuable properties for nutrition and general health.
- PUFA polyunsaturated fatty acids
- cardiovascular risks including a lower risk of thrombosis, reduced arteriosclerosis, antiarrhythmic effects, inhibition of cytokine release, reduction of blood viscosity
- omega-3 polyunsaturated fatty acids have received special attention. They are long chain polyunsaturated fatty acids having multiple non-conjugated carbon-carbon double bonds with the first of their double bonds at the third carbon atom from their methyl terminus. Among these, docosahexaenoic acid (DHA, C22:6 n-3, cervonic acid) and (all-Z)-5,8,11 ,14,17- eicosapen-
- DHA docosahexaenoic acid
- C22:6 n-3, cervonic acid docosahexaenoic acid
- all-Z -5,8,11 ,14,17- eicosapen-
- taenoic acid EPA, C20:5 n-3, timnodonic acid
- Other common omega-3 fatty acids include, but are not limited to, octadecatrienoic acid (C18:3 n-3, alpha-linolenic acid), octadecatetraenoic acid (C18:4 n-3; stearidonic acid), eicosatetraenoic acid (C20:4 n-3) and docosapentaenoic acid (C22:5 n-3).
- DHA is one of the predominant fatty acids in the structural phospholipids of the human brain and retina and accumulates rapidly in foetal and infant neural tissue during the last months of gestation and the first months of postnatal life. It is thus particularly recommended that pregnant, neonate and infant persons shall receive a required dose of omega-3 fatty acids and particularly of DHA.
- Omega-3 fatty acids and particularly DHA and EPA are mainly contained in marine oils and particularly fish oils like tuna oil.
- Other sources of DHA and EPA include oils gener- ated from algae and fungi.
- fish oils and biotechnologically produced algal or fungal oils are generally not consumed voluntarily in their recommended amount. This is particularly true for fish oils, which frequently exhibit a repulsive odour due to the production of low molecular amines and oxidation products during storage of such oils.
- WO 94/01001 discloses a microencapsulated oil or fat product, wherein at least one oil or fat is dispersed in a matrix material as particles or drops having an average diameter of less than or equal to 2 ⁇ m, the oil or fat containing at least 10 wt.-% of highly unsaturated fatty acids, preferably omega-3 and omega-6 fatty acids, the level of free fatty acids being below 5 wt.-% and preferably below 0.5 wt.-% and the matrix material consisting of caseinate and optionally at least one carbohydrate.
- microencapsulated product can be used in foods, such as infant formulas, health functional foods, dietetic foods and pharmaceuticals, wherein a high content or fat or oil containing at least one highly unsaturated fatty acid or a derivative thereof is desired.
- the microencapsulated product particularly addresses require- ments of a European Community Commission directive of 14 May 1991 regarding ingredients of infant formulas.
- Further nutritional compositions are described in EP 0 764 405 A2, WO 03/024237 A1 and EP 0 425 213 A2. The present invention intends to further these advantages.
- a generally preferred source of DHA in a natural oil is tuna oil.
- a typical refined tuna oil for human consumption contains approximately 23-25 wt.-% of DHA moieties and approximately 28 wt.-% of saturated fatty acid moieties.
- Saturated fatty acids have been implicated in unwanted decreases of low density lipoprotein (LDL) levels, high cholesterol levels and unwanted high triglyceride levels in blood, which are all believed to increase the risk of coronary illnesses. It is thus desired to reduce the content of saturated fatty acids in DHA containing compositions while maintaining high DHA levels.
- LDL low density lipoprotein
- Another requirement and thus object of the invention is to provide a particulate product having storage and transportation stability as well as mechanical strength and performance during further processing into tablets, extrudates and reconstituted emulsions or other edible end products.
- Storage and transport stability requires that a particulate product must not smell of old fish after 2 weeks storage in the dark at 25 0 C, 50 % humid- ity, and also the anisidine value must not exceed 15 as determined according to European Pharmacopoeia 6.6 section 2.5.36 "Anisidine value".
- the oil to be used in the manufacture of the particulate product should have a minimum content of 3 wt.-% of saturated fatty acids. Oils having a lower content of saturated fatty acids are presently intolerably expensive; the costs for producing a particulate product using an oil having less than 3 wt.-% of saturated fatty acids would be too high for incorporating the product into infant nutrition products.
- the invention thus generally discloses a microparticle including a collection of such microparticles and a nutritional or pharmaceutical product comprising such microparticles.
- the microparticles comprise a fat soluble fraction and a matrix for forming the microparti- cle and embedding the fat soluble fraction.
- the fat soluble fraction comprises a docosa- hexaenoic acid moiety.
- the total amount of the fat soluble fraction is 31 - 44 wt.-% of the microparticle, the total amount of docosahexaenoic acid moieties is at least 1 1 wt.-% of the microparticle, the total amount of saturated fatty acid moieties is at most 12.5 wt.-% of the microparticle and at least 3 wt.-% of the fat soluble fraction, and the total amount of free surface fat is at the most 0.7 wt.-% of the microparticle.
- the invention further provides a method of producing a microparticle.
- the method comprises the steps of
- the steps and ingredients are chosen such that the total amount of the fat soluble fraction is 31 - 44 wt.-% of the microparticle, the total amount of docosahexaenoic acid moieties is at least 11 wt.-% of the microparticle, the total amount of saturated fatty acid moieties is at most 12.5 wt.-% of the microparticle, and the total amount of free surface fat is at the most 0.7 wt.-% of the microparticle.
- microparticle denotes a particle comprising a matrix material and a fat soluble fraction.
- Microparticles according to the invention preferably have a mean diameter of 5 mm or smaller, particularly preferably 2 mm - 0.01 mm, more prefer- ably 1.5 mm - 0.2 mm and further preferably 0.6 - 0.1 mm measured by sieving in accordance with European Pharmacopoeia 6.6, section 2.9.38, using a Retch AS200 to agitate the sieves for 15 minutes.
- emulsion denotes both an emulsion and a suspension.
- An emulsion as used herein denotes a liquid matrix comprising droplets of at least one further liquid phase.
- suspension is used herein denotes a liquid phase comprising solid particles dispersed therein.
- free surface fat denotes such fatty substances as being readily extractable by an organic solvent and specifically petroleum ether under the conditions specified later herein.
- the free surface fat typically is located on the microparticle surface or in cavities within the microparticle but having contact to the particle surface through capillaries or cracks in the microparticle matrix.
- fat solube means hydrophobic organic compounds soluble in lipids.
- fatty acid moieties shall be understood to refer to both the fatty acid as such and to any substance having the respective fatty acid connected to the remainder of the substance via the fatty acid's carboxy terminus.
- monoglycerides, diglyce- rides and triglycerides of fatty acids constitute the main ingredients of lipids, oils and fats.
- docosahexaenoic acid moiety refers to docosahexaenoic acid as such, and also to that part of a substance, e.g. of a mono-, di- or triglyceride, which would be docosahexaenoic acid after hypothetical cleavage of the covalent bond at its carboxy terminus.
- natural oil refers to an oil derived from a living entity and containing at least one ester of an omega-3 fatty acid.
- a "fish oil” within the meaning of the present description thus is a natural oil derived from a fish or other marine organism, and is preferably refined for human consumption. Refining preferably includes de- acidification (remove free fatty acids), bleaching (reduce colour and heavy metal and pollutants (organic substances)), distillation and deodorization (steam injection during vacuum) and in some cases winterization (cooling down to precipitation of high melting fats/triglycerides). Fish oils tend to have a triglyceride content of at least 90 wt.-% of the oil. When referring to “natural oil” or "fish oil”, tuna oils are generally particularly preferred due to their naturally high content of docosahexaenoic acid moieties.
- a typical refined tuna oil composition is:
- Triglycerides 95 - 99 wt.-%, Diglycerides: 2 - 5 wt.-%, Monoglycerides: 0 - 1 wt.-%, Free fatty acids: 0 - 1 wt.-%,
- the content of saturated fatty acid moieties typically is at least 28 wt.-% of the tuna oil.
- the most prominent saturated fatty acid moieties are palmitic acid (19.5 wt.-%), stearic acid (5 wt.-%) and myristic acid (3.8 wt.- %), again referring to the total tuna oil.
- concentrate refers to a mixture obtainable or obtained from a natural oil and preferably a fish oil, by at least one step of concentrating desired fatty acids and reesterification of the concentrated fatty acids to yield a fat or an oil, or by deesterification of undesired fatty acids, preferably by enzymatic cleavage, and removal of such undesired fatty acids.
- a typical concentrate according to the present invention will have a composition of:
- Triglycerides 50 - 65 wt.-%, Diglycerides: 30 - 50 wt.-%, Monoglycerides: 0 - 5 wt.-%, Free fatty acids: 0 - 1 wt.-%,
- the content of saturated fatty acid moieties preferably is at most 5 wt.-% of the concentrate.
- Concentrates preferably have a content of less than 1 wt.-% of myristic acid moieties, less than 2 wt.-% of palmitic acid moieties, and less than 3 wt.-% of stearic acid moieties, again referring to the total concentrate.
- the term "embedding" denotes a thorough mixture of matrix material and fat soluble fraction in a substantially dry form, i.e. at a water content of the microparticles of less than 5 wt.-%.
- the fat soluble fraction forms droplets of up to 1 ⁇ m average diameter, and said droplets preferably have an average diameter in water of up to 0.5 ⁇ m.
- the average diameter is measured with a Mastersizer 2000 (Malvern) laser diffractometer.
- the microparticles of the present invention comprise a fat soluble fraction.
- Main ingredients of such fat soluble fraction preferably are natural oils, particularly tuna oil, and concentrates, as will become apparent hereinafter.
- the fat soluble fraction can further comprise other substances besides natural oils and concentrates as will be detailed later.
- the total amount of the fat soluble fraction is 31 - 44 wt.-% of the microparticle, preferably 35 - 43 wt.-% of the microparticle. It has suprisingly been found that at this concentration, the desired minimum concentration of 11 wt.-% of docosahexaenoic acid moieties can be achieved, and still the particle maintains a low content of free surface fat.
- the total amount of free surface fat is thus at most 0.7 wt.-% of the microparticle, preferably 0.4 - 0.01 wt.-% and most preferably 0.13 - 0.02 wt.-%.
- the low amount of total free surface fat is decisive for providing a free flowing powder of microparticles of the present invention, as the microparticles do not significantly adhere to each other, and is also beneficial to ensure a good oxidation stability.
- the process of the invention it has also surprisingly become possible to increase the amount of docosahexaenoic acid moieties and the amount of fat soluble fraction without increasing the amount of matrix material, particularly of hydrocolloids.
- Conventional attempts to include a higher amount of fat soluble fraction where hampered by a need to achieve or maintain a high content of hydrocolloid and particularly of hydrocolloids to prevent formation of a high amount of free surface fat.
- the process for preparing the microparticles of the invention is cost-efficient.
- the fraction of docosahexaenoic acid moieties and other ingredients of the fat so- luble fraction directly exposed to air and thus to oxidation stress conditions can be kept low. Therefore, the microparticles are mechanically and chemically stable during storage, transport and further processing, e.g. into tablets, extrudates or food mixes.
- the present invention allows to reduce this amount compared to a hitherto used tuna oil by 10 %.
- health concerns can be effectively addressed by the microparticles of the present invention and their respective method of manufacture.
- a typical reduction in total saturated fatty acid moieties of 10 % relative to the total fat soluble fraction of a typical tuna oil can be achieved.
- the total amount of saturated fatty acids is at most 22.7 wt.-%, even more preferably at most 20 wt.-% and most preferably at most 17 wt.-% of the fat soluble fraction, corresponding to a decrease of approximately 20%, 30% and 40% compared to a typical refined tuna oil.
- a minimum amount of saturated fatty acid moieties is 3 wt.-% of the fat soluble fraction.
- the microparticles preferably contain a total amount of myristic acid moieties of at most 3.5 wt.-%, preferably at most 3 wt.-%, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-%, relative to the total fat soluble fraction.
- the microparticles of the present invention also preferably contain a total amount of palmitic acid moieties of at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction. And also preferably the microparticles of the present invention comprise a total amount of stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-%, relative to the total fat soluble fraction.
- the total amount of triglycerides preferably is at most 85.5 wt.-%, more preferably at most 76 wt.-%, even more preferably at most 66.5 wt.-% and most preferably at most 57 wt.-% of the fat soluble fraction.
- this corresponds to a reduction compared to a conventional tuna oil of 10 %, more preferably of 20 %, even more preferably of 30 % and most preferably of 40 %.
- the fat soluble fraction of the microparticles of the present invention comprise
- eicosapentaenoic acid C20:5 omega-3, EPA
- eicosapentaenoic acid C20:5 omega-3, EPA
- moieties preferably at least 5 wt.-% and most preferably 7 - 12 wt.-% of eicosapentaenoic acid moieties
- alpha-linolenic acid C18:3 omega-3, alpha-LNA
- gamma-linolenic acid C18:3 omega-6, gamma-LNA
- all weight percentages relative to the total fat soluble fraction all weight percentages relative to the total fat soluble fraction.
- the microparticles of the present invention comprise DHA and EPA moieties in a ratio of total weights of at least 4 (DHA):1(EPA) and further preferably up to 5.5:1 , thereby mimicking the ratio found in human milk.
- the fat soluble fraction of the microparticle of the present invention comprises
- a natural oil comprising docosahexaenoic acid moieties, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, and
- the total amount of docosahexaenoic acid moieties in the natural oil is less than the amount required to achieve a total amount of docosahexaenoic acid moieties of at least 11 wt.-% in the microparticle, and
- the total amount of docosahexaenoic acid moieties in the concentrate is suffi- cient to complement the amount of docosahexaenoic acid moieties in the natural oil to achieve a total amount of docosahexaenoic acid moieties of at least 1 1 wt.-% of the microparticle.
- the amount of saturated fatty acid moieties and the amount of triglycerides in a microparticle of the invention can be decreased without lowering the total content of docosahexaenoic acid moieties or increasing the amount of surface fat.
- the concentrate preferably is a natural oil concentrate - preferably a tuna oil concentrate -, obtainable or obtained by a process comprising the steps:
- the total amount of docosahexaenoic acid moieties is at least 20 wt.-%, particularly preferably 21 - 30 wt.-% and even more preferably 23 - 25 wt.-% of the natural oil. Also preferably, the total amount of docosahexaenoic acid moieties is at least 42 wt.- %, particularly preferably 43 -80 wt.-% and more preferably 44 - 75 wt.-% of the concentrate.
- compositions of natural oil and/or concentrate are particularly adapted to achieve the desired high DHA content of the microparticle while simultaneously achieving the desired low content of saturated fatty acid moieties and free surface fat. It is thus particu- larly preferred to combine them in a ratio of (natural oil:concentrate) 86:14 to 50:50 parts by weight.
- the skilled person can select a ratio suitable for achieving a minimum content of DHA moieties of 11 wt.-% of the microparticle while maintaining the total amount of fat soluble fraction, free surface fat and content of saturated fatty acid moieties.
- Another preferred concentrate is obtainable or obtained by
- a) deesterification of a natural oil preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, preferably by enzymatic cleavage, of fatty acid moieties other than DHA and/or EPA, and
- the total amount of DHA moieties is at least 21 wt.%, preferably 22-39 wt.% and particularly preferably 24-29 wt.% of the total concentrate.
- the total amount of EPA moieties in the concentrate is preferably 5-15 wt.% and more preferably 5-12 wt.%.
- a concentrate of natural oils wherein undesired fatty acid moieties have been deesterified and removed as described in steps a) and b) above is preferably used instead of natural oil when preparing the microparticles of the present invention and is thus preferably not mixed with a natural oil to produce the fat soluble fraction of the microparticles.
- the microparticle of the present invention comprises a matrix for forming the micropar- ticle and embedding the fat soluble fraction therein.
- the matrix preferably comprises a hydrocolloid material and preferably also a plasticizer.
- the hydrocol- loid material is selected from the group consisting of milk protein or milk protein hydroly- sates, whey protein, caseinates, gelatine, polysaccharides and mixtures of the aforementioned substances.
- Preferred polysaccharides are alginate, carrageenan, gum arabic, gum acacia, modified gum acacia, pectins, modified pectins and modified starch, prefera- bly sodium octenyl succinate modified starch.
- Particularly preferred matrix materials comprise caseinate, particularly sodium and/or potassium caseinate. It has been found that sodium or potassium caseinates and particularly potassium caseinate are particularly suitable for embedding the fat soluble fraction to maintain a desired low surface fat content.
- caseinate may be used as the only matrix material, it is preferred to use a combination of caseinate and a plasticizer, preferably a carbohydrate and/or carbohydrate alcohol, as matrix material.
- a plasticizer preferably a carbohydrate and/or carbohydrate alcohol
- Preferred plasticizers are lactose, maltose, saccharose, glucose, glucose syrup, fructose, lactose, invert sugar, sorbitol, manitol, trehalose, targatose, pullulan, raftilose (oligofruc- tose), dextrin, maltodextrin, glycerin and mixtures thereof, such as saccharose, trehalose, pullulan, dextrin and raftilose and mixtures thereof.
- Particularly preferred plasticizers are glucose syrup, maltodextrin, saccharose, maltose and lactose, most preferably maltodex- trin and/or saccharose.
- a weight ratio of plasticizer : caseinate (particularly potassium caseinate) of 8.5:1 to 4.5:1 provides an increased mechanical stability of the microparticles for the presently selected total amount the fat soluble fraction and its composition according to the present invention when compared to a matrix consisting of caseinate or saccharose as such. Further, said weight ratio minimizes the proportion of free surface fat of the microparticles.
- the weight ratio between the fat soluble fraction and the hydrocolloid, preferably casei- nate and most preferably K-caseinate, is preferably at least 4.5:1 , particularly preferably at least 6:1 and more preferably at least 7:1. These weight ratios are particularly adapted to achieve a sufficiently stable microparticle under mechanical and oxidation (exposure to ambient air) stress as well as a good storage stability combined with a low content of free surface fat.
- the microparticle of the present invention preferably is a spray dried microparticle.
- a spray dried microparticle preferably an oil-in-water-emulsion of the fat soluble fraction
- the matrix material and water is homogenised and atomised into a spray drying tower to evaporate water of the emulsion.
- the gas phase in the spray drying tower contains a starch or modified starch and/or further anticaking agent to finely cover the drying microparticles.
- a preferred microparticle of the present invention will thus comprise 20-30 wt.-% starch, relative to the total microparticle, 4-10 wt.-% further substances, preferably including or consisting of sodium ascorbate, relative to the amount of fat soluble fraction, 17-36 wt.-% sucrose, relative to the total microparticle, 10-50 wt.-% of hydrocolloid, relative to the amount of fat soluble fraction, a total of 31-44 wt.-% of fat soluble fraction, relative to the total microparticle, and up to 5 wt.-% of water, relative to the total microparticle.
- further substances preferably including or consisting of sodium ascorbate, relative to the amount of fat soluble fraction, 17-36 wt.-% sucrose, relative to the total microparticle, 10-50 wt.-% of hydrocolloid, relative to the amount of fat soluble fraction, a total of 31-44 wt.-% of fat soluble fraction, relative to the total microparticle, and
- the free surface fat content of the microparticle of the present invention at most 0.7 %, particularly preferably at most 0.4 %, even more preferably at most 0.15 % and most preferably at most 0.13 %. It has further been found that a minimum amount of free surface fat of 0.01 % yields an acceptable, free flowing powder of microparticles of the present invention.
- the fat soluble fraction of the microparticles of the present invention can comprise further substances and moieties besides substances having a docosahexaenoic acid moiety, i.e. docosahexaenoic acid as such and/or preferably mono-, di- and/or triglycerides comprising at least one docosahexaenoic acid moiety.
- Preferred further contents of the fat so- luble fraction are provitamins and vitamins, particularly vitamin A and esters thereof, vitamin E and esters thereof, preferably vitamin E-acetate, vitamin D, preferably vitamin D2 and/or vitamin D3, vitamin K, preferably vitamin K1 , further monounsatu rated fatty acids and polyunsaturated fatty acids besides docosahexaenoic acid, preferably conjugated linolenic acid (CLA), carotenoids, preferably beta-caroten, lutein, lycopene, beta- cryptoxanthin, astaxanthin, cantaxanthin, citranaxanthin and zeaxanthin, curcumin and benzoquinones, preferably coenzyme Q10 (ubidecarenone).
- CLA conjugated linolenic acid
- carotenoids preferably beta-caroten, lutein, lycopene, beta- cryptoxanthin, astaxanthin, cantaxanthin, citranaxant
- the microparticles of the present invention comprise a fat soluble fraction preferably consisting of or preferably essentially consisting of the aforementioned fatty acid moieties, particularly DHA and preferably also EPA, and one or more of the substances mentioned before in this paragraph.
- microparticles of the present invention may contain further substances which are not necessarily part of the fat soluble fraction. Particularly preferred, the microparticles may contain
- antioxidants preferably T-butyl hydroxyl toluene (BHT), T-butyl hydroxyl anisole (BHA), ascorbic acid, sodium ascorbate, citric acid, sodium citrate EDTA and its salts, tocopherols, preferably natural tocopherol and particularly preferably gamma- tocopherol, tert.-butylhydroquinone (TBHQ), ethoxyquine, propyl gallate, herb extracts, preferably rosemary and/or oregano extract;
- BHT T-butyl hydroxyl toluene
- BHA T-butyl hydroxyl anisole
- ascorbic acid sodium ascorbate
- citric acid sodium citrate EDTA and its salts
- tocopherols preferably natural tocopherol and particularly preferably gamma- tocopherol, tert.-butylhydroquinone (TBHQ), ethoxyquine, propyl gallate, herb extracts,
- tricalciumphosphate and silicate particularly preferably silicon dioxide and sodium aluminium silicate, tricalciumphosphate being most preferred
- emulsifiers and surfactants particularly preferably ascorbyl palmitate, sucrose esters, mono- and diglycerides of fatty acids and derivatives thereof, and lecithin.
- the matrix of the microparticles of the present invention preferably consists of or preferably consists essentially of the matrix material as described above, preferably including one or more hydrocolloids and further preferably including one or more plasti- cizers, and preferably one or more emulsifiers and/or surfactants.
- the present invention further relates to end products comprising the microparticles of the present invention.
- a preferred end product is a food, a food supplement, a beverage, a pharmaceutical or veterinary product, a feed or feed supplement and a personal care product.
- Particularly preferred end products are nutritional, nutrition supplementary and pharmaceutical end products.
- infant nutrition compositions including neonate nutrition products are particularly preferred.
- the microparticles of the present invention are not included in such end product in an amount insufficient for achieving a physiological effect. Instead, the skilled person will work with synthetical propensity, i.e. building up rather than tearing down, to achieve the benefits available via the microparticles of the present invention.
- microparticles of the present invention may be dissolved in the end product and no longer be present in microparticulate form.
- microparticles of the present invention are typically not produced or sold one single particle a time. Thus, whenever the present description refers to a "microparticle" of the present invention, it is to be understood that also a multiplicity of microparticles is meant.
- a preferred quantity of microparticles of the present invention is at least 5 kg of microparticles, more preferably at least 20 kg of microparticles and most preferably at least 25 kg of microparticles.
- a preferred production batch quantity is thus preferably at least 5, 20 or 25 kg, but more preferably is at least 100 kg, more preferably at least 500 kg and most preferably at least 1000 kg.
- the invention further relates to a method of producing a microparticle according to the present invention.
- a natural oil and a concentrate is added to a water phase to form the fat soluble fraction of an oil-in-water-emulsion.
- Preferable compositions and amounts of natural oil, concentrate and further ingredients of the fat soluble fraction have been indicated above.
- Homogenization is preferably performed using a high shear system, further preferably a rotor-stator system, and most preferably a high pressure homogenizer.
- the method of the present invention allows to produce the microparticles of the present invention reproducibly and in the form of a free flowing powder at an economically sensible large scale.
- Example 1 Test method for determination of free surface fat
- microparticles are dispersed in petroleum ether, whereby the amount of fat which is not embedded dissolves and is determined by means of weight analysis. Free surface fat content is expressed as the extracted amount of fat in relation to the weighed amount of product, as described below.
- caseinate preferably potassium caseinate
- saccharose dissolved in water, preferably at a temperature of 50-70 0 C.
- the solution is then degassed by reduction of air pressure, and followingly preferably kept under an atmosphere of nitrogen.
- Sodium ascorbate is added to the solution before or after degassing.
- Fish oil preferably tuna oil, concentrate, tocopherol, a fat soluble antioxidant mixture comprising ascorbyl palmitate, lecithin and further mono- and diglycerides of fatty acids are mixed and are added to the degassed solution under vigorous agitation at 50-70 0 C to form a pre-emulsion.
- the pre-emulsion is then homogenised by high pressure homogeni- sation to yield an emulsion, but can also be emulsified in a high shear mixer, e.g. a rotor stator mixer.
- the emulsion is spray dried in hot air comprising starch and tricalcium phosphate.
- the powder thus obtained (including the powders of examples 3a and 3b) is particularly suitable for preparing an infant or neonate formula to achieve the beneficial physiological effects referred to at the beginning of this description.
- Microparticles of the present invention are obtained.
- Example 3a DHA oil: caseinate ratio 8:1
- 288 potassium caseinate, 1346 g sucrose and 138 g sodium ascorbate were dissolved in 1500 ml water at 65 0 C under agitation.
- 2300 g DHA oil (1978 g natural tuna oil and 322 g concentrate) was mixed with mixed tocopherol to 3000 ppm and 13.04 g fat soluble antioxidant (comprising ascorbyl palmitate, lecithin and further mono- and diglycerides of fatty acids), heated to 65 0 C and added to the aqueous solution under agitation.
- the DHA oil was made of a mixture of tuna oil and concentrate and had a content of docosahexae- noic acid moieties of 282 mg/g of oil and a content of eicosapentaenoic acid moieties of 66 mg/g of oil.
- a pre-emulsion was thus obtained.
- the pre-emulsion was homogenised in a rotor/stator system and diluted followed by one pass at 550 bar through a high pressure homogeniser. After homogenisation, a sprayable emulsion (oil-in-water-emulsion) is obtained.
- the sprayable emulsion was atomized in a spray drying tower with added maize starch and tricalcium phosphate as powdering agents.
- Total amount of fat soluble fraction 42.4 wt.-% of microparticles.
- Total content of triglycerides 90.8 wt.-% of the fat soluble fraction.
- the DHA oil was obtained by mixing tuna oil and concentrate in a ratio of 86 (tuna oil): 14 (concentrate).
- the microparticles were obtained as a free flowing powder.
- Example 3b Alternative DHA: Caseinate ratio of 8:1 238 g potassium caseinate, 1816 g sucrose and 114 g sodium ascorbate were dissolved in 1300 ml water at 65 0 C under agitation. 1908 g of DHA oil (1240 g natural tuna oil and 668 g concentrate) was mixed with mixed tocopherol to 3000 ppm and 10.8 g fat soluble antioxidant (comprising ascorbyl palmitate, lecithin and further mono- and diglycerides of fatty acids), containing 350 mg/g docosahexaenoic acid moieties and 65 mg/g eicosapen- taenoic acid moieties, heated to 65 0 C and added to the aqueous solution under vigorous agitation. A pre-emulsion was obtained.
- the pre-emulsion was diluted, homogenized (two passes at 500 bar) and dried as described for example 3a. A free flowing powder of microparticles was obtained. This dried powder had the following characteristics:
- Free surface fat 0.03 %.
- Total triglyceride content 84.5 % of the fat soluble fraction.
- the DHA oil was obtained by mixing tuna oil and concentrate in a ratio of 65 (tuna oil):35 (concentrate).
- a preferred infant nutrition dry formula comprising the microparticles of the invention (Examples 3 and 5) and further adding arachidonic acid has the composition:
- Example 5 Manufacturing method using enzymatically treated tuna oil
- Example 3a was reproduced. However, the "DHA oil” was replaced by the identical quantitiy of a concentrate, said concentrate being an enzymatically treated tuna oil.
- Embodiment 1 Microparticle comprising a fat soluble fraction and a matrix for forming the microparticle and embedding the fat soluble fraction, wherein the fat soluble fraction comprises a docosahexaenoic acid (C22:6 omega-3,
- DHA DHA moiety
- the total amount of the fat soluble fraction is 35-43 wt-% of the microparticle, and the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle, - the total amount of saturated fatty acid moieties is at most 12.5 wt% of the micro- particle, and at least 3 wt.-% of the fat soluble fraction, and the total amount of free surface fat is at most 0.7 % of the microparticle, preferably 0.01-0.4 wt. % an most preferably 0.02-0.13 wt.%.
- Embodiment 2 A microparticle as described in Embodiment 1 , wherein the total amount of saturated fatty acids in the fat soluble fraction of the microparticle is at most 22.7 wt.- %, preferably at most 20 wt.-% and most preferably 3-17 wt.-% of the fat soluble fraction.
- Embodiment 3 A microparticle as described in Embodiment 2, having
- alpha-linolenic acid C18:3 omega-3, alpha-LNA
- gamma-linolenic acid C18:3 omega-6, gamma-LNA
- a total amount of palmitic acid moieties of at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction, and further having a total amount of - 0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or
- eicosapentaenoic acid C20:5 omega-3, EPA
- eicosapentaenoic acid C20:5 omega-3, EPA
- moieties preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction; and/or c) a total amount of stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt
- Embodiment 4 A microparticle having
- the fat soluble fraction comprises a docosahexaenoic acid (C22:6 omega-3, DHA) moiety, characterized in that the total amount of the fat soluble fraction is 31-44 wt.-% of the microparticle, and the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle, preferably 11-44 wt.-% and even more preferably 12-44 wt.-% of the microparticle, - the total amount of saturated fatty acid moieties is 3 to 9.99 wt.-% of the microparticle, and the total amount of free surface fat is at most 0.7 % of the microparticle, preferably 0.01-0.4 wt. % an most preferably 0.02-0.13 wt.%.
- C22:6 omega-3, DHA docosahexaenoic acid
- Embodiment 5 A microparticle of Embodiment 4, wherein the total amount of saturated fatty acid moieties is at most 8.8 wt.-%, preferably at most 7.48 wt.-% and more prefara- bly 0.93-7.31 wt.-%, all weight percentages relative to the total microparticle.
- Embodiment 6 A microparticle of Embodiment 4, wherein
- the total amount of myristic acid moieties is at most 3.5 wt.-%, preferably at most 3 wt.- %, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-% of the total fat soluble fraction, and further having a total amount of
- the total amount of palmitic acid moieties is at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction, and further having a total amount of
- the total amount of stearic acid moieties is at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-% of the total fat soluble fraction, and further having a total amount of
- arachidonic acid C20:4 omega-6, AA
- EPA eicosapentaenoic acid
- alpha-linolenic acid C18:3 omega
- Embodiment 7 A microparticle according to Embodiment 1 , 2, 3, 4, 5 or 6, having a mean particle diameter of 2 mm - 0.01 mm, more preferably 1.5 mm - 0.2 mm and further preferably 0.6 - 0.1 mm.
- Embodiment 8 A microparticle according to any of Embodiments 1 , 2, 3, 4, 5, 6 or 7, which, when dissolved in still water at 25 0 C and 1013 hPa, forms oil phase droplets having an average diameter of at most 1 ⁇ m, preferably at most 0.5 ⁇ m.
- Embodiment 9 A microparticle comprising or consisting of 20-30 wt.-% starch, relative to the total microparticle, preferably 22-28 wt.-%, 4-10 wt.-%, preferably 4.5-9 wt.-%, of further substances, preferably including or consisting of sodium ascorbate, relative to the amount of fat soluble fraction,
- the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle, and the total amount of saturated fatty acid moieties is at most 12.5 wt% of the microparticle and at least 3 wt.-% of the fat soluble fraction, and the total amount of free surface fat is at most 0.7 wt.-% of the microparticle.
- Embodiment 9 A microparticle as described in Embodiment 8, having
- stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-% of the total fat soluble fraction, and further having a total amount of
- alpha-linolenic acid C18:3 omega-3, alpha-LNA
- gamma-linolenic acid C18:3 omega-6, gamma-LNA
- Preferred manufacturing process 1 A process for manufacturing any of Embodiments 1 , 2, 3, 4, 5, 6, 7, 8 or 9, comprising the steps of
- a natural oil preferably a marine oil and most preferably a tuna oil, having a total amount of DHA moieties of at least 20 wt.-%, preferably 23-25 wt.-%, the weight percentages being relative to the total oil,
- step b2 before, during or after step b1 ) obtaining a concentrate having a total amount of DHA moieties of at least 42 wt.-%, preferably 43-80 wt.-% and more preferably 44-75 wt.-%, the weight percentages beng relative to the total concentrate,
- Preferred manufacturing process 2 A process for manufacturing any of Embodiments 1 , 2, 3, 4, 5, 6, 7, 8 or 9, comprising the steps of
- a natural oil preferably a marine oil and most preferably a tuna oil, having a total amount of DHA moieties of at least 20 wt.-%, preferably 23-25 wt.-%, the weight percentages being relative to the total oil,
Abstract
The present invention relates to microparticles comprising a docosahexaenoic acid moiety having a low content of saturated fatty acid moieties and a low content of free surface fat. The invention further relates to uses of such microparticles, methods of their manufacture and products comprising the microparticles.
Description
MICROPARTICLES COMPRISING A FAT SOLUBLE FRACTION COMPRISING DHA AND THEIR
PRODUCTION
The present invention relates to microparticles comprising a docosahexaenoic acid moiety having a low content of saturated fatty acid moieties and a low content of free surface fat. The invention further relates to uses of such microparticles, methods of their manufacture and products comprising the microparticles.
5 Compositions comprising significant amounts of highly unsaturated fatty acids have frequently been shown to possess valuable properties for nutrition and general health. Particularly, polyunsaturated fatty acids (PUFA) have been implicated in treatment or prevention of cardiovascular risks including a lower risk of thrombosis, reduced arteriosclerosis, antiarrhythmic effects, inhibition of cytokine release, reduction of blood viscosity
10 and reduction of arterial hypertension. In view of these effects, omega-3 polyunsaturated fatty acids have received special attention. They are long chain polyunsaturated fatty acids having multiple non-conjugated carbon-carbon double bonds with the first of their double bonds at the third carbon atom from their methyl terminus. Among these, docosahexaenoic acid (DHA, C22:6 n-3, cervonic acid) and (all-Z)-5,8,11 ,14,17- eicosapen-
15 taenoic acid (EPA, C20:5 n-3, timnodonic acid) are considered particularly important. Other common omega-3 fatty acids include, but are not limited to, octadecatrienoic acid
(C18:3 n-3, alpha-linolenic acid), octadecatetraenoic acid (C18:4 n-3; stearidonic acid), eicosatetraenoic acid (C20:4 n-3) and docosapentaenoic acid (C22:5 n-3).
DHA is one of the predominant fatty acids in the structural phospholipids of the human brain and retina and accumulates rapidly in foetal and infant neural tissue during the last months of gestation and the first months of postnatal life. It is thus particularly recommended that pregnant, neonate and infant persons shall receive a required dose of omega-3 fatty acids and particularly of DHA.
Omega-3 fatty acids and particularly DHA and EPA are mainly contained in marine oils and particularly fish oils like tuna oil. Other sources of DHA and EPA include oils gener- ated from algae and fungi. However, fish oils and biotechnologically produced algal or fungal oils are generally not consumed voluntarily in their recommended amount. This is particularly true for fish oils, which frequently exhibit a repulsive odour due to the production of low molecular amines and oxidation products during storage of such oils.
It has thus frequently been tried to produce formulations comprising omega-3 fatty acids in a stabilized form. For example, WO 94/01001 discloses a microencapsulated oil or fat product, wherein at least one oil or fat is dispersed in a matrix material as particles or drops having an average diameter of less than or equal to 2 μm, the oil or fat containing at least 10 wt.-% of highly unsaturated fatty acids, preferably omega-3 and omega-6 fatty acids, the level of free fatty acids being below 5 wt.-% and preferably below 0.5 wt.-% and the matrix material consisting of caseinate and optionally at least one carbohydrate. According to this document, such microencapsulated product can be used in foods, such as infant formulas, health functional foods, dietetic foods and pharmaceuticals, wherein a high content or fat or oil containing at least one highly unsaturated fatty acid or a derivative thereof is desired. The microencapsulated product particularly addresses require- ments of a European Community Commission directive of 14 May 1991 regarding ingredients of infant formulas. Further nutritional compositions are described in EP 0 764 405 A2, WO 03/024237 A1 and EP 0 425 213 A2. The present invention intends to further these advantages.
It is thus generally desired to produce products containing a high amount of DHA, while the product is still in a stabilized form with low inclination of developing unpleasant odours during storage. However, there are constraints making the development of such products difficult:
According to an approach as described in WO 94/01001 polyunsaturated fatty acids are combined with a carrier, i. e. a caseinate, to produce a powder. For such encapsulation products, the content of free surface fat is an important parameter. A content of free surface fat of more than 1 wt.-% is considered an impaired quality, as such product is prone to fast deterioration. Furthermore, such products develop stickiness and cannot readily be handled as a free flowing powder. Instead, special provisions for handling of such products have to be taken.
Another constraint is that such products require a high amount of carrier to prevent fatty acids from becoming free surface fat. An increase in carrier content, however, necessarily entails a decrease of total fat content, thus limiting the maximum total fat content. It is thus desired to avoid an increase in carrier content when trying to achieve a high total content of fat-soluble substances. Also, the relationship between total fat content, amount of carrier material and type of carrier material and total fat is not understood; it was thus not possible to optimize the selection and ratio of fat and carrier materials by routine experimentation. Due to lack of guidance by any established principles, the teachings of any of the above prior art documents could not be extended or combined with a reasonable expectation of success.
A generally preferred source of DHA in a natural oil is tuna oil. A typical refined tuna oil for human consumption, however, contains approximately 23-25 wt.-% of DHA moieties and approximately 28 wt.-% of saturated fatty acid moieties. Saturated fatty acids have been implicated in unwanted decreases of low density lipoprotein (LDL) levels, high cholesterol levels and unwanted high triglyceride levels in blood, which are all believed to increase the risk of coronary illnesses. It is thus desired to reduce the content of saturated fatty acids in DHA containing compositions while maintaining high DHA levels.
Another requirement and thus object of the invention is to provide a particulate product having storage and transportation stability as well as mechanical strength and performance during further processing into tablets, extrudates and reconstituted emulsions or other edible end products. Storage and transport stability requires that a particulate product must not smell of old fish after 2 weeks storage in the dark at 250C, 50 % humid- ity, and also the anisidine value must not exceed 15 as determined according to European Pharmacopoeia 6.6 section 2.5.36 "Anisidine value".
- A -
Another requirement is that the oil to be used in the manufacture of the particulate product should have a minimum content of 3 wt.-% of saturated fatty acids. Oils having a lower content of saturated fatty acids are presently intolerably expensive; the costs for producing a particulate product using an oil having less than 3 wt.-% of saturated fatty acids would be too high for incorporating the product into infant nutrition products.
SUMMARY OF THE INVENTION
The invention thus generally discloses a microparticle including a collection of such microparticles and a nutritional or pharmaceutical product comprising such microparticles. The microparticles comprise a fat soluble fraction and a matrix for forming the microparti- cle and embedding the fat soluble fraction. The fat soluble fraction comprises a docosa- hexaenoic acid moiety. The total amount of the fat soluble fraction is 31 - 44 wt.-% of the microparticle, the total amount of docosahexaenoic acid moieties is at least 1 1 wt.-% of the microparticle, the total amount of saturated fatty acid moieties is at most 12.5 wt.-% of the microparticle and at least 3 wt.-% of the fat soluble fraction, and the total amount of free surface fat is at the most 0.7 wt.-% of the microparticle.
The invention further provides a method of producing a microparticle. The method comprises the steps of
(a) providing a water phase comprising a matrix former, preferably a hydrocolloid matrix former and preferably also comprising a plasticizer,
(b) adding a concentrate and optionally a natural oil to the water phase to form the fat soluble fraction of an oil-in-water-emulsion,
(c) homogenising the emulsion, and
(d) spray drying the emulsion to achieve microparticles.
In this method, the steps and ingredients are chosen such that the total amount of the fat soluble fraction is 31 - 44 wt.-% of the microparticle, the total amount of docosahexaenoic acid moieties is at least 11 wt.-% of the microparticle, the total amount of saturated fatty acid moieties is at most 12.5 wt.-% of the microparticle, and the total amount of free surface fat is at the most 0.7 wt.-% of the microparticle.
DETAILED DESCRIPTION OF THE INVENTION:
As used herein, the term ,,microparticle" denotes a particle comprising a matrix material and a fat soluble fraction. Microparticles according to the invention preferably have a mean diameter of 5 mm or smaller, particularly preferably 2 mm - 0.01 mm, more prefer- ably 1.5 mm - 0.2 mm and further preferably 0.6 - 0.1 mm measured by sieving in accordance with European Pharmacopoeia 6.6, section 2.9.38, using a Retch AS200 to agitate the sieves for 15 minutes.
The term "dispersion" as used herein denotes both an emulsion and a suspension. An emulsion as used herein denotes a liquid matrix comprising droplets of at least one further liquid phase. The term "suspension" is used herein denotes a liquid phase comprising solid particles dispersed therein.
The term "free surface fat" as used herein denotes such fatty substances as being readily extractable by an organic solvent and specifically petroleum ether under the conditions specified later herein. The free surface fat typically is located on the microparticle surface or in cavities within the microparticle but having contact to the particle surface through capillaries or cracks in the microparticle matrix.
In the context of the present invention, the term "fat solube" means hydrophobic organic compounds soluble in lipids.
All references to fatty acid moieties shall be understood to refer to both the fatty acid as such and to any substance having the respective fatty acid connected to the remainder of the substance via the fatty acid's carboxy terminus. Particularly, monoglycerides, diglyce- rides and triglycerides of fatty acids constitute the main ingredients of lipids, oils and fats.
Thus, for example the term "docosahexaenoic acid moiety" refers to docosahexaenoic acid as such, and also to that part of a substance, e.g. of a mono-, di- or triglyceride, which would be docosahexaenoic acid after hypothetical cleavage of the covalent bond at its carboxy terminus.
As used herein, the term "natural oil" refers to an oil derived from a living entity and containing at least one ester of an omega-3 fatty acid. A "fish oil" within the meaning of the present description thus is a natural oil derived from a fish or other marine organism, and is preferably refined for human consumption. Refining preferably includes de-
acidification (remove free fatty acids), bleaching (reduce colour and heavy metal and pollutants (organic substances)), distillation and deodorization (steam injection during vacuum) and in some cases winterization (cooling down to precipitation of high melting fats/triglycerides). Fish oils tend to have a triglyceride content of at least 90 wt.-% of the oil. When referring to "natural oil" or "fish oil", tuna oils are generally particularly preferred due to their naturally high content of docosahexaenoic acid moieties. A typical refined tuna oil composition is:
Triglycerides: 95 - 99 wt.-%, Diglycerides: 2 - 5 wt.-%, Monoglycerides: 0 - 1 wt.-%, Free fatty acids: 0 - 1 wt.-%,
all weight percentages referring to the total oil. The content of saturated fatty acid moieties typically is at least 28 wt.-% of the tuna oil. The most prominent saturated fatty acid moieties are palmitic acid (19.5 wt.-%), stearic acid (5 wt.-%) and myristic acid (3.8 wt.- %), again referring to the total tuna oil.
As used herein, the term "concentrate" refers to a mixture obtainable or obtained from a natural oil and preferably a fish oil, by at least one step of concentrating desired fatty acids and reesterification of the concentrated fatty acids to yield a fat or an oil, or by deesterification of undesired fatty acids, preferably by enzymatic cleavage, and removal of such undesired fatty acids.
A typical concentrate according to the present invention will have a composition of:
Triglycerides: 50 - 65 wt.-%, Diglycerides: 30 - 50 wt.-%, Monoglycerides: 0 - 5 wt.-%, Free fatty acids: 0 - 1 wt.-%,
each time referring to the total concentrate. The content of saturated fatty acid moieties preferably is at most 5 wt.-% of the concentrate. Concentrates preferably have a content of less than 1 wt.-% of myristic acid moieties, less than 2 wt.-% of palmitic acid moieties, and less than 3 wt.-% of stearic acid moieties, again referring to the total concentrate.
For the present invention, the term "embedding" denotes a thorough mixture of matrix material and fat soluble fraction in a substantially dry form, i.e. at a water content of the microparticles of less than 5 wt.-%. In an emulsion or after dissolving of the microparticles in water, the fat soluble fraction forms droplets of up to 1 μm average diameter, and said droplets preferably have an average diameter in water of up to 0.5 μm. The average diameter is measured with a Mastersizer 2000 (Malvern) laser diffractometer.
The microparticles of the present invention comprise a fat soluble fraction. Main ingredients of such fat soluble fraction preferably are natural oils, particularly tuna oil, and concentrates, as will become apparent hereinafter. The fat soluble fraction can further comprise other substances besides natural oils and concentrates as will be detailed later.
The total amount of the fat soluble fraction is 31 - 44 wt.-% of the microparticle, preferably 35 - 43 wt.-% of the microparticle. It has suprisingly been found that at this concentration, the desired minimum concentration of 11 wt.-% of docosahexaenoic acid moieties can be achieved, and still the particle maintains a low content of free surface fat.
The total amount of free surface fat is thus at most 0.7 wt.-% of the microparticle, preferably 0.4 - 0.01 wt.-% and most preferably 0.13 - 0.02 wt.-%. Without wanting to be bound by any particular theory, it is contemplated that the low amount of total free surface fat is decisive for providing a free flowing powder of microparticles of the present invention, as the microparticles do not significantly adhere to each other, and is also beneficial to ensure a good oxidation stability.
By the process of the invention it has also surprisingly become possible to increase the amount of docosahexaenoic acid moieties and the amount of fat soluble fraction without increasing the amount of matrix material, particularly of hydrocolloids. Conventional attempts to include a higher amount of fat soluble fraction where hampered by a need to achieve or maintain a high content of hydrocolloid and particularly of hydrocolloids to prevent formation of a high amount of free surface fat. Thus, the process for preparing the microparticles of the invention is cost-efficient.
Further, as the amount of free surface fat can be kept low according to the present invention, the fraction of docosahexaenoic acid moieties and other ingredients of the fat so- luble fraction directly exposed to air and thus to oxidation stress conditions can be kept
low. Therefore, the microparticles are mechanically and chemically stable during storage, transport and further processing, e.g. into tablets, extrudates or food mixes.
In view of the total amount of saturated fatty acid moieties, the present invention allows to reduce this amount compared to a hitherto used tuna oil by 10 %. Thus, health concerns can be effectively addressed by the microparticles of the present invention and their respective method of manufacture. Considering the compositions of tuna oil and concentrate as given above, a typical reduction in total saturated fatty acid moieties of 10 % relative to the total fat soluble fraction of a typical tuna oil can be achieved.
Preferably, the total amount of saturated fatty acids is at most 22.7 wt.-%, even more preferably at most 20 wt.-% and most preferably at most 17 wt.-% of the fat soluble fraction, corresponding to a decrease of approximately 20%, 30% and 40% compared to a typical refined tuna oil. A minimum amount of saturated fatty acid moieties is 3 wt.-% of the fat soluble fraction.
Among the saturated fatty acid moieties, a reduction is particularly desired for myristic acid moieties, and/or palmitic acid moieties, and/or stearic acid moieties. Thus, according to the invention the microparticles preferably contain a total amount of myristic acid moieties of at most 3.5 wt.-%, preferably at most 3 wt.-%, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-%, relative to the total fat soluble fraction. The microparticles of the present invention also preferably contain a total amount of palmitic acid moieties of at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction. And also preferably the microparticles of the present invention comprise a total amount of stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-%, relative to the total fat soluble fraction. Thus, compared to a conventional refined tuna oil a reduction in myristic, palmitic and/or stearic acid moieties of 10 %, more preferably of 20 %, even more preferably of 30 % and most preferably of 40 % can be achieved.
Likewise, the total amount of triglycerides preferably is at most 85.5 wt.-%, more preferably at most 76 wt.-%, even more preferably at most 66.5 wt.-% and most preferably at most 57 wt.-% of the fat soluble fraction. Again, this corresponds to a reduction compared to a conventional tuna oil of 10 %, more preferably of 20 %, even more preferably of 30 % and most preferably of 40 %.
Preferably, the fat soluble fraction of the microparticles of the present invention comprise
- 0 - 5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties,
- 0 - 16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7 - 12 wt.-% of eicosapentaenoic acid moieties,
- 0 - 5 wt. -% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and
- 0 - 5 wt. -% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction.
For physiological reasons, it is further preferred that the microparticles of the present invention comprise DHA and EPA moieties in a ratio of total weights of at least 4 (DHA):1(EPA) and further preferably up to 5.5:1 , thereby mimicking the ratio found in human milk.
Preferably, the fat soluble fraction of the microparticle of the present invention comprises
- a natural oil comprising docosahexaenoic acid moieties, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, and
- a concentrate comprising docosahexaenoic acid moieties,
wherein the total amount of docosahexaenoic acid moieties in the natural oil is less than the amount required to achieve a total amount of docosahexaenoic acid moieties of at least 11 wt.-% in the microparticle, and
wherein the total amount of docosahexaenoic acid moieties in the concentrate is suffi- cient to complement the amount of docosahexaenoic acid moieties in the natural oil to achieve a total amount of docosahexaenoic acid moieties of at least 1 1 wt.-% of the microparticle.
It has now been found that by reducing the amount of natural oil in a microparticle, the beneficial properties of such microparticles can actually be promoted. Thus, instead of
raising the amount of natural oil in a microparticle to achieve a total content of docosa- hexaenoic acid moieties in the microparticle of at least 11 wt.-%, it has now been found that at least part of the natural oil should be replaced by a concentrate containing doco- sahexaenoic acid moieties. This way, the amount of saturated fatty acid moieties and the amount of triglycerides in a microparticle of the invention can be decreased without lowering the total content of docosahexaenoic acid moieties or increasing the amount of surface fat.
The concentrate preferably is a natural oil concentrate - preferably a tuna oil concentrate -, obtainable or obtained by a process comprising the steps:
(a) deesterification of fatty acid di- and/or triglycerides of a natural oil, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, wherein deesterification is by enzymatic cleavage or another process,
(b) isolation of selected fatty acids and removal of non-selected fatty acids, preferably by distillation,
(c) reesterification of the isolated fatty acids into monoglycerides, diglycerides and triglycerides.
Preferably, the total amount of docosahexaenoic acid moieties is at least 20 wt.-%, particularly preferably 21 - 30 wt.-% and even more preferably 23 - 25 wt.-% of the natural oil. Also preferably, the total amount of docosahexaenoic acid moieties is at least 42 wt.- %, particularly preferably 43 -80 wt.-% and more preferably 44 - 75 wt.-% of the concentrate.
Such compositions of natural oil and/or concentrate are particularly adapted to achieve the desired high DHA content of the microparticle while simultaneously achieving the desired low content of saturated fatty acid moieties and free surface fat. It is thus particu- larly preferred to combine them in a ratio of (natural oil:concentrate) 86:14 to 50:50 parts by weight. In view of the present description, the skilled person can select a ratio suitable for achieving a minimum content of DHA moieties of 11 wt.-% of the microparticle while maintaining the total amount of fat soluble fraction, free surface fat and content of saturated fatty acid moieties.
Another preferred concentrate is obtainable or obtained by
a) deesterification of a natural oil, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, preferably by enzymatic cleavage, of fatty acid moieties other than DHA and/or EPA, and
b) removal of deesterified fatty acids.
In this case, the total amount of DHA moieties is at least 21 wt.%, preferably 22-39 wt.% and particularly preferably 24-29 wt.% of the total concentrate. Also, the total amount of EPA moieties in the concentrate is preferably 5-15 wt.% and more preferably 5-12 wt.%. A concentrate of natural oils wherein undesired fatty acid moieties have been deesterified and removed as described in steps a) and b) above is preferably used instead of natural oil when preparing the microparticles of the present invention and is thus preferably not mixed with a natural oil to produce the fat soluble fraction of the microparticles.
The microparticle of the present invention comprises a matrix for forming the micropar- ticle and embedding the fat soluble fraction therein. The matrix preferably comprises a hydrocolloid material and preferably also a plasticizer. Particularly preferred the hydrocol- loid material is selected from the group consisting of milk protein or milk protein hydroly- sates, whey protein, caseinates, gelatine, polysaccharides and mixtures of the aforementioned substances. Preferred polysaccharides are alginate, carrageenan, gum arabic, gum acacia, modified gum acacia, pectins, modified pectins and modified starch, prefera- bly sodium octenyl succinate modified starch. Particularly preferred matrix materials comprise caseinate, particularly sodium and/or potassium caseinate. It has been found that sodium or potassium caseinates and particularly potassium caseinate are particularly suitable for embedding the fat soluble fraction to maintain a desired low surface fat content.
Although caseinate may be used as the only matrix material, it is preferred to use a combination of caseinate and a plasticizer, preferably a carbohydrate and/or carbohydrate alcohol, as matrix material.
Preferred plasticizers are lactose, maltose, saccharose, glucose, glucose syrup, fructose, lactose, invert sugar, sorbitol, manitol, trehalose, targatose, pullulan, raftilose (oligofruc- tose), dextrin, maltodextrin, glycerin and mixtures thereof, such as saccharose, trehalose,
pullulan, dextrin and raftilose and mixtures thereof. Particularly preferred plasticizers are glucose syrup, maltodextrin, saccharose, maltose and lactose, most preferably maltodex- trin and/or saccharose. It has been found that a weight ratio of plasticizer : caseinate (particularly potassium caseinate) of 8.5:1 to 4.5:1 provides an increased mechanical stability of the microparticles for the presently selected total amount the fat soluble fraction and its composition according to the present invention when compared to a matrix consisting of caseinate or saccharose as such. Further, said weight ratio minimizes the proportion of free surface fat of the microparticles.
The weight ratio between the fat soluble fraction and the hydrocolloid, preferably casei- nate and most preferably K-caseinate, is preferably at least 4.5:1 , particularly preferably at least 6:1 and more preferably at least 7:1. These weight ratios are particularly adapted to achieve a sufficiently stable microparticle under mechanical and oxidation (exposure to ambient air) stress as well as a good storage stability combined with a low content of free surface fat.
The microparticle of the present invention preferably is a spray dried microparticle. For spray drying, preferably an oil-in-water-emulsion of the fat soluble fraction, the matrix material and water is homogenised and atomised into a spray drying tower to evaporate water of the emulsion. Most preferably, the gas phase in the spray drying tower contains a starch or modified starch and/or further anticaking agent to finely cover the drying microparticles.
A preferred microparticle of the present invention will thus comprise 20-30 wt.-% starch, relative to the total microparticle, 4-10 wt.-% further substances, preferably including or consisting of sodium ascorbate, relative to the amount of fat soluble fraction, 17-36 wt.-% sucrose, relative to the total microparticle, 10-50 wt.-% of hydrocolloid, relative to the amount of fat soluble fraction, a total of 31-44 wt.-% of fat soluble fraction, relative to the total microparticle, and up to 5 wt.-% of water, relative to the total microparticle.
The free surface fat content of the microparticle of the present invention at most 0.7 %, particularly preferably at most 0.4 %, even more preferably at most 0.15 % and most preferably at most 0.13 %. It has further been found that a minimum amount of free surface fat of 0.01 % yields an acceptable, free flowing powder of microparticles of the present invention.
The fat soluble fraction of the microparticles of the present invention can comprise further substances and moieties besides substances having a docosahexaenoic acid moiety, i.e. docosahexaenoic acid as such and/or preferably mono-, di- and/or triglycerides comprising at least one docosahexaenoic acid moiety. Preferred further contents of the fat so- luble fraction are provitamins and vitamins, particularly vitamin A and esters thereof, vitamin E and esters thereof, preferably vitamin E-acetate, vitamin D, preferably vitamin D2 and/or vitamin D3, vitamin K, preferably vitamin K1 , further monounsatu rated fatty acids and polyunsaturated fatty acids besides docosahexaenoic acid, preferably conjugated linolenic acid (CLA), carotenoids, preferably beta-caroten, lutein, lycopene, beta- cryptoxanthin, astaxanthin, cantaxanthin, citranaxanthin and zeaxanthin, curcumin and benzoquinones, preferably coenzyme Q10 (ubidecarenone). Further preferred are fat soluble antioxidants, particularly ascorbyl palmitate. Thus, the microparticles of the present invention comprise a fat soluble fraction preferably consisting of or preferably essentially consisting of the aforementioned fatty acid moieties, particularly DHA and preferably also EPA, and one or more of the substances mentioned before in this paragraph.
The microparticles of the present invention may contain further substances which are not necessarily part of the fat soluble fraction. Particularly preferred, the microparticles may contain
- antioxidants, preferably T-butyl hydroxyl toluene (BHT), T-butyl hydroxyl anisole (BHA), ascorbic acid, sodium ascorbate, citric acid, sodium citrate EDTA and its salts, tocopherols, preferably natural tocopherol and particularly preferably gamma- tocopherol, tert.-butylhydroquinone (TBHQ), ethoxyquine, propyl gallate, herb extracts, preferably rosemary and/or oregano extract;
- anticaking agents, preferably tricalciumphosphate and silicate, particularly preferably silicon dioxide and sodium aluminium silicate, tricalciumphosphate being most preferred;
- emulsifiers and surfactants, particularly preferably ascorbyl palmitate, sucrose esters, mono- and diglycerides of fatty acids and derivatives thereof, and lecithin.
Thus, the matrix of the microparticles of the present invention preferably consists of or preferably consists essentially of the matrix material as described above, preferably
including one or more hydrocolloids and further preferably including one or more plasti- cizers, and preferably one or more emulsifiers and/or surfactants.
The present invention further relates to end products comprising the microparticles of the present invention. A preferred end product is a food, a food supplement, a beverage, a pharmaceutical or veterinary product, a feed or feed supplement and a personal care product. Particularly preferred end products are nutritional, nutrition supplementary and pharmaceutical end products. Among these, infant nutrition compositions including neonate nutrition products are particularly preferred. The skilled person understands that the microparticles of the present invention are not included in such end product in an amount insufficient for achieving a physiological effect. Instead, the skilled person will work with synthetical propensity, i.e. building up rather than tearing down, to achieve the benefits available via the microparticles of the present invention. For example, he will include enough microparticles to achieve a physiologically sensible intake of DHA moieties by a consumer, particularly preferred an infant or neonate, while maintaining a low intake of saturated fatty acid moieties. The microparticles of the present invention may be dissolved in the end product and no longer be present in microparticulate form. By including microparticles of the present invention in an end product of the above type, the beneficial effects particularly for infants and neonates referred to above can be achieved.
The microparticles of the present invention are typically not produced or sold one single particle a time. Thus, whenever the present description refers to a "microparticle" of the present invention, it is to be understood that also a multiplicity of microparticles is meant. A preferred quantity of microparticles of the present invention is at least 5 kg of microparticles, more preferably at least 20 kg of microparticles and most preferably at least 25 kg of microparticles. A preferred production batch quantity is thus preferably at least 5, 20 or 25 kg, but more preferably is at least 100 kg, more preferably at least 500 kg and most preferably at least 1000 kg.
The invention further relates to a method of producing a microparticle according to the present invention. In the method as given above a natural oil and a concentrate is added to a water phase to form the fat soluble fraction of an oil-in-water-emulsion. Preferable compositions and amounts of natural oil, concentrate and further ingredients of the fat soluble fraction have been indicated above. Homogenization is preferably performed using a high shear system, further preferably a rotor-stator system, and most preferably a high pressure homogenizer. The method of the present invention allows to produce the
microparticles of the present invention reproducibly and in the form of a free flowing powder at an economically sensible large scale.
The invention will hereinafter be further described by reference to preferred examples. The examples shall be understood as not to limit the scope of the claims or the scope of disclosure of the present description.
Example 1 : Test method for determination of free surface fat
Principle: The microparticles are dispersed in petroleum ether, whereby the amount of fat which is not embedded dissolves and is determined by means of weight analysis. Free surface fat content is expressed as the extracted amount of fat in relation to the weighed amount of product, as described below.
Method: Weigh 10.00 g product into a 250 ml Erlenmeyer flask.
Add 50.0 ml petroleum ether to the flask and shake for a few seconds.
Decant the petroleum ether into a counterbalanced 100 ml Erlenmeyer flask through a Whatman No. 4 paper filter, which has been moistened with petroleum ether.
Repeat the procedure with another 50 ml petroleum ether and again with 2 x 10 ml petroleum ether.
Evaporate the entire amount of petroleum ether under nitrogen at max. 4O0C and place the flask in an incubator at 1050C for one hour and allow to cool in a desiccator.
Weigh the flask in grams (4 decimals).
Calculate the content of free surface fat content (%) in the samples by the following equation:
i- J- Is ample
ITi1 = Weight of flask (g)
ITi2 = Weight of flask with free fat (g)
msampie = Weighed sample (g)
Example 2: General manufacturing method
In a first step caseinate (preferably potassium caseinate) and saccharose are dissolved in water, preferably at a temperature of 50-700C. The solution is then degassed by reduction of air pressure, and followingly preferably kept under an atmosphere of nitrogen. Sodium ascorbate is added to the solution before or after degassing.
Fish oil, preferably tuna oil, concentrate, tocopherol, a fat soluble antioxidant mixture comprising ascorbyl palmitate, lecithin and further mono- and diglycerides of fatty acids are mixed and are added to the degassed solution under vigorous agitation at 50-700C to form a pre-emulsion. The pre-emulsion is then homogenised by high pressure homogeni- sation to yield an emulsion, but can also be emulsified in a high shear mixer, e.g. a rotor stator mixer. The emulsion is spray dried in hot air comprising starch and tricalcium phosphate.
The powder thus obtained (including the powders of examples 3a and 3b) is particularly suitable for preparing an infant or neonate formula to achieve the beneficial physiological effects referred to at the beginning of this description.
Microparticles of the present invention are obtained.
Example 3: Preferred methods of manufacture
In a general method according to example 2, the following contents were used:
Example 3a:
DHA oil: caseinate ratio 8:1
288 potassium caseinate, 1346 g sucrose and 138 g sodium ascorbate were dissolved in 1500 ml water at 650C under agitation. 2300 g DHA oil (1978 g natural tuna oil and 322 g concentrate) was mixed with mixed tocopherol to 3000 ppm and 13.04 g fat soluble antioxidant (comprising ascorbyl palmitate, lecithin and further mono- and diglycerides of fatty acids), heated to 650C and added to the aqueous solution under agitation. The DHA oil was made of a mixture of tuna oil and concentrate and had a content of docosahexae- noic acid moieties of 282 mg/g of oil and a content of eicosapentaenoic acid moieties of 66 mg/g of oil. A pre-emulsion was thus obtained. The pre-emulsion was homogenised in a rotor/stator system and diluted followed by one pass at 550 bar through a high pressure homogeniser. After homogenisation, a sprayable emulsion (oil-in-water-emulsion) is obtained.
The sprayable emulsion was atomized in a spray drying tower with added maize starch and tricalcium phosphate as powdering agents.
The resulting dry powder of microparticles had the following characteristics:
Total amount of fat soluble fraction: 42.4 wt.-% of microparticles.
Total amount of docosahexaenoic acid moieties: 11.9 wt.-% of the microparticles.
Total content of eisocapentaenoic acid moieties: 2.8 wt.-% of microparticles.
Total amount of free surface fat: 0.13 %.
Total amount of myristic, palmitic and stearic acid moieties: 10.6 wt.-% of the microparticles.
Total content of triglycerides: 90.8 wt.-% of the fat soluble fraction.
The DHA oil was obtained by mixing tuna oil and concentrate in a ratio of 86 (tuna oil): 14 (concentrate). The microparticles were obtained as a free flowing powder.
Example 3b: Alternative DHA: Caseinate ratio of 8:1
238 g potassium caseinate, 1816 g sucrose and 114 g sodium ascorbate were dissolved in 1300 ml water at 650C under agitation. 1908 g of DHA oil (1240 g natural tuna oil and 668 g concentrate) was mixed with mixed tocopherol to 3000 ppm and 10.8 g fat soluble antioxidant (comprising ascorbyl palmitate, lecithin and further mono- and diglycerides of fatty acids), containing 350 mg/g docosahexaenoic acid moieties and 65 mg/g eicosapen- taenoic acid moieties, heated to 650C and added to the aqueous solution under vigorous agitation. A pre-emulsion was obtained.
The pre-emulsion was diluted, homogenized (two passes at 500 bar) and dried as described for example 3a. A free flowing powder of microparticles was obtained. This dried powder had the following characteristics:
Total amount of fat soluble fraction: 35.3 wt.-% of the microparticles.
Total content of docosahexaenoic acid moieties: 12.2 wt.-% of the microparticles.
Total content of eisocapentaenoic acid moieties: 2.3 wt.-% of microparticles.
Free surface fat: 0.03 %.
Total content of myristic, palmitic and stearic acid moieties: 7.0 % of the fat soluble fraction.
Total triglyceride content: 84.5 % of the fat soluble fraction.
The DHA oil was obtained by mixing tuna oil and concentrate in a ratio of 65 (tuna oil):35 (concentrate).
Example 4: End product
A preferred infant nutrition dry formula comprising the microparticles of the invention (Examples 3 and 5) and further adding arachidonic acid has the composition:
Example 5: Manufacturing method using enzymatically treated tuna oil
Example 3a was reproduced. However, the "DHA oil" was replaced by the identical quantitiy of a concentrate, said concentrate being an enzymatically treated tuna oil.
The invention is hereinafter further explained by way of some preferred embodiments, which achieve the advatages described above.
Embodiment 1 : Microparticle comprising a fat soluble fraction and a matrix for forming the microparticle and embedding the fat soluble fraction, wherein the fat soluble fraction comprises a docosahexaenoic acid (C22:6 omega-3,
DHA) moiety,
characterized in that the total amount of the fat soluble fraction is 35-43 wt-% of the microparticle, and the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle, - the total amount of saturated fatty acid moieties is at most 12.5 wt% of the micro- particle, and at least 3 wt.-% of the fat soluble fraction, and the total amount of free surface fat is at most 0.7 % of the microparticle, preferably 0.01-0.4 wt. % an most preferably 0.02-0.13 wt.%.
Embodiment 2: A microparticle as described in Embodiment 1 , wherein the total amount of saturated fatty acids in the fat soluble fraction of the microparticle is at most 22.7 wt.- %, preferably at most 20 wt.-% and most preferably 3-17 wt.-% of the fat soluble fraction.
Embodiment 3: A microparticle as described in Embodiment 2, having
a) a total amount of myristic acid moieties of at most 3.5 wt.-%, preferably at most 3 wt.- %, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or
0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or - 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction; and/or
b) a total amount of palmitic acid moieties of at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction, and further having a total amount of - 0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or
0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction; and/or
c) a total amount of stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or - 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction.
Embodiment 4: A microparticle having
a fat soluble fraction and a matrix for forming the microparticle and embedding the fat soluble fraction, wherein the fat soluble fraction comprises a docosahexaenoic acid (C22:6 omega-3, DHA) moiety, characterized in that the total amount of the fat soluble fraction is 31-44 wt.-% of the microparticle, and the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle, preferably 11-44 wt.-% and even more preferably 12-44 wt.-% of the microparticle, - the total amount of saturated fatty acid moieties is 3 to 9.99 wt.-% of the microparticle, and the total amount of free surface fat is at most 0.7 % of the microparticle, preferably 0.01-0.4 wt. % an most preferably 0.02-0.13 wt.%.
Embodiment 5: A microparticle of Embodiment 4, wherein the total amount of saturated fatty acid moieties is at most 8.8 wt.-%, preferably at most 7.48 wt.-% and more prefara- bly 0.93-7.31 wt.-%, all weight percentages relative to the total microparticle.
Embodiment 6: A microparticle of Embodiment 4, wherein
a) the total amount of myristic acid moieties is at most 3.5 wt.-%, preferably at most 3 wt.- %, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or
0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction;
b) the total amount of palmitic acid moieties is at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or - 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction; and/or
c) the total amount of stearic acid moieties is at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction.
Embodiment 7: A microparticle according to Embodiment 1 , 2, 3, 4, 5 or 6, having a mean particle diameter of 2 mm - 0.01 mm, more preferably 1.5 mm - 0.2 mm and further preferably 0.6 - 0.1 mm.
Embodiment 8: A microparticle according to any of Embodiments 1 , 2, 3, 4, 5, 6 or 7, which, when dissolved in still water at 250C and 1013 hPa, forms oil phase droplets having an average diameter of at most 1 μm, preferably at most 0.5 μm.
Embodiment 9: A microparticle comprising or consisting of
20-30 wt.-% starch, relative to the total microparticle, preferably 22-28 wt.-%, 4-10 wt.-%, preferably 4.5-9 wt.-%, of further substances, preferably including or consisting of sodium ascorbate, relative to the amount of fat soluble fraction,
17-36 wt.-%, preferably 21-31 wt.-%, of sucrose, relative to the total microparticle, - 10-50 wt.-%, preferably 12-25 wt.-%, of hydrocolloid, preferably including or consisting of sodium caseinate, relative to the amount of fat soluble fraction, a total of 31-44 wt.-%, of fat soluble fraction, relative to the total microparticle, and up to 5 wt.-% of water, relative to the total microparticle,
wherein
- the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle, and the total amount of saturated fatty acid moieties is at most 12.5 wt% of the microparticle and at least 3 wt.-% of the fat soluble fraction, and the total amount of free surface fat is at most 0.7 wt.-% of the microparticle.
Embodiment 9: A microparticle as described in Embodiment 8, having
a) a total amount of myristic acid moieties of at most 3.5 wt.-%, preferably at most 3 wt.-
%, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or - 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction; and/or
b) a total amount of palmitic acid moieties of at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction, and further having a total amount of 0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or 0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or
0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction; and/or
c) a total amount of stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-% of the total fat soluble fraction, and further having a total amount of
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties, and/or 0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties, and/or
0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and/or - 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties, all weight percentages relative to the total fat soluble fraction.
Preferred manufacturing process 1 : A process for manufacturing any of Embodiments 1 , 2, 3, 4, 5, 6, 7, 8 or 9, comprising the steps of
a) providing a water phase comprising a matrix former,
b1 ) obtaining a natural oil, preferably a marine oil and most preferably a tuna oil, having a total amount of DHA moieties of at least 20 wt.-%, preferably 23-25 wt.-%, the weight percentages being relative to the total oil,
b2) before, during or after step b1 ) obtaining a concentrate having a total amount of DHA moieties of at least 42 wt.-%, preferably 43-80 wt.-% and more preferably 44-75 wt.-%, the weight percentages beng relative to the total concentrate,
b3) mixing the oils of steps b1 ) and b2) in a ratio of (a:b) 86:14 to 50:50,
b4) adding the mixture to the water phase to form the fat soluble fraction of a resulting oil- in-water emulsion,
c) homogenizing the emulsion, and
d) spray drying the emulsion to obtain the microparticles.
Preferred manufacturing process 2: A process for manufacturing any of Embodiments 1 , 2, 3, 4, 5, 6, 7, 8 or 9, comprising the steps of
a) providing a water phase comprising a matrix former,
b1 ) obtaining a natural oil, preferably a marine oil and most preferably a tuna oil, having a total amount of DHA moieties of at least 20 wt.-%, preferably 23-25 wt.-%, the weight percentages being relative to the total oil,
b2) deesterification of fatty acid moieties other than DHA and optionally EPA from the oil of step b1 ),
b3) removal of free fatty acids from the deesterified oil of step b2) to obtain a concentrate
b4) adding the concentrate to the water phase to form the fat soluble fraction of a resulting oil- in-water emulsion,
c) homogenizing the emulsion, and
d) spray drying the emulsion to obtain the microparticles.
Claims
1. Microparticle comprising
a fat soluble fraction and
a matrix for forming the microparticle and embedding the fat soluble fraction,
wherein the fat soluble fraction comprises a docosahexaenoic acid (C22:6 omega-3, DHA) moiety,
characterized in that
the total amount of the fat soluble fraction is 31-44 wt% of the microparticle, and
the total amount of docosahexaenoic acid moieties is at least 11 wt% of the micro- particle,
the total amount of saturated fatty acid moieties is at most 12.5 wt% of the microparticle, and at least 3 wt.-% of the fat soluble fraction, and
the total amount of free surface fat is at most 0.7 % of the microparticle.
2. Microparticle according to claim 1 , wherein
a) the total amount of myristic acid moieties of at most 3.5 wt.-%, preferably at most 3 wt.- %, even more preferably at most 2.7 wt.-% and most preferably at most 2.3 wt.-% of the total fat soluble fraction, and/or
b) the total amount of palmitic acid moieties of at most 17.5 wt.-%, more preferably at most 15.6 wt.-%, even more preferably at most 13.7 wt.-% and most preferably at most 11.7 wt.-% of the total fat soluble fraction, and/or c) the total amount of stearic acid moieties of at most 4.5 wt.-%, more preferably at most 4 wt.-%, even more preferably at most 3.5 wt.-% and most preferably at 3.1 wt.-% of the total fat soluble fraction.
3. Microparticle according to any of the previous claims, wherein the fat soluble fraction further comprises
0-5 wt.-% of arachidonic acid (C20:4 omega-6, AA) moieties,
0-16 wt.-% of eicosapentaenoic acid (C20:5 omega-3, EPA) moieties, preferably at least 5 wt.-% and most preferably 7-12 wt.-% of eicosapentaenoic acid moieties,
0-5 wt.-% of alpha-linolenic acid (C18:3 omega-3, alpha-LNA) moieties, and
- 0-5 wt.-% of gamma-linolenic acid (C18:3 omega-6, gamma-LNA) moieties,
all weight percentages relative to the total fat soluble fraction.
4. Microparticle according to any of the previous claims, wherein the fat soluble fraction comprises
a natural oil comprising docosahexaenoic acid moieties, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, and
a concentrate comprising docosahexaenoic acid moieties,
wherein the total amount of docosahexaenoic acid moieties in the natural oil is less than the amount required to achieve a total amount of docosahexaenoic acid moieties of at least 11 wt% of the microparticle, and
wherein the total amount of docosahexaenoic acid moieties in the concentrate is sufficient to complement the amount of docosahexaenoic acid moieties in the natural oil to achieve a total amount of docosahexaenoic acid moieties of at least 11 wt% of the microparticle.
5. Microparticle according to claim 4, wherein
a) the total amount of docosahexaenoic acid moieties is at least 20 wt.-%, preferably 21-30 wt%, and even more preferably 23-25 wt% of the natural oil; and/or
b) the total amount of docosahexaenoic acid moieties is at least 42 wt%, preferably 43-80 wt% and more preferaby 44-75 wt% of the concentrate.
6. Microparticle according to any of the previous claims, wherein
the matrix consists of, consists substantially of or comprises
a hydrocolloid material preferably selected from the group consisting of milk protein or hydrolysates, whey protein, caseinate, gelatine, polysaccharides and mixtures of the aforementioned substances, wherein the polysaccharide or polysaccharides is/are selected from alginate, carrageenan, gum arabic, gum acacia, modified gum acacia, pectins, modified pectins and modified starch, preferably sodium octenyl succinate modified starch, and mixtures of such polysaccharides,
- and preferably also a plasticizer, the plasticizer preferably being selected of lactose, maltose, saccharose, glucose, glucose syrup, fructose, lactose, invert sugar, sorbitol, manitol, trehalose, targatose, pullulan, raftilose (oligo- fructose), dextrin, maltodextrin, glycerin and mixtures thereof, such as saccharose, trehalose, pullulan, dextrin and raftilose and mixtures thereof,
- and the ratio between said fat soluble fraction and the hydrocolloid is at least 4.5:1 , preferably at least 6:1 , more preferably at least 7:1.
7. Microparticle according to any of the previous claims, wherein the micro-particle is a spray dried microparticle.
8. Microparticle according to any of the previous claims, wherein the free surface fat content of at most 0.7%, preferably at most 0.4% and more preferably 0.01-0.13 %.
9. Microparticle according to any of the previous claims, wherein the fat soluble fraction further comprises one or more of:
provitamins and vitamins, particularly vitamin A and esters thereof, vitamin E and esters thereof, preferably vitamin E-acetate, vitamin D, preferably vitamin D2 and/or vitamin D3, vitamin K, preferably vitamin K1 ,
further monounsatu rated fatty acids and polyunsaturated fatty acids besides doco- sahexaenoic acid, preferably conjugated linolenic acid (CLA),
carotenoids, preferably beta-caroten, lutein, lycopene, beta-cryptoxanthin, astaxan- thin, cantaxanthin, citranaxanthin and zeaxanthin, curcumin and benzoquinones, prefera- bly coenzyme Q10 (ubidecarenone), and/or
fat soluble antioxidants, particularly ascorbyl palmitate.
10. Microparticle according to any of the previous claims, further comprising one or more of:
- antioxidants, preferably T-butyl hydroxyl toluene (BHT), T-butyl hydroxyl anisole (BHA), ascorbic acid, sodium ascorbate, citric acid, sodium citrate EDTA and its salts, tocopherols, preferably natural tocopherol and particularly preferably gamma- tocopherol, tert.-butylhydroquinone (TBHQ), ethoxyquine, propyl gallate, herb extracts, preferably rosemary and/or oregano extract,
- anticaking agents, preferably tricalciumphosphate and silicate, particularly preferably silicon dioxide and sodium aluminium silicate, tricalciumphosphate being most preferred;
- emulsifiers and surfactants, particularly preferably ascorbyl palmitate, sucrose esters, mono- and diglycerides of fatty acids and derivatives thereof, and lecithin.
11. A microparticle according to any of claims 1 to 10, further comprising
- 20-30 wt.-% starch, relative to the total microparticle, the starch being preferably of potato, wheat, maize, tapioca and/or rice.
12. End product comprising microparticles of any of claims 1 to 11 , wherein the end product is selected from the group consisting of food, food supplement, beverage, pharmaceutical or veterinary product, feed or feed supplement and personal care product, and preferably is an infant and/or neonate nutrition product .
13. Method of producing a microparticle according to any of claims 1 to 11 , comprising the steps of
(a) providing a water phase comprising a matrix former, preferably a hydrocolloid matrix former,
(b) adding concentrate and optionally a natural oil to the water phase to form the fat soluble fraction of an oil-in-water emulsion,
(c) homogenizing the emulsion, and
(d) spray drying the emulsion to achieve microparticles,
wherein
the total amount of the fat soluble fraction is 31-44 wt% of the microparticle, and
- the total amount of docosahexaenoic acid moieties is at least 11 wt% of the microparticle,
the total amount of saturated fatty acid moieties is at most 12.5 wt% of the microparticle, and
the total amount of free surface fat is at most 0.7 % of the microparticle.
14. Method according to claim 13, wherein step (a) further comprises adding a plasti- cizer and/or a water-soluble antioxidant.
15. Method according to any of claims 13 to 14, wherein the concentrate concentrate is obtainable or obtained by a process comprising the steps: a) deesterification of a natural oil, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, preferably by enzymatic cleavage, of fatty acid moieties other than DHA and/or EPA, and
b) removal of deesterified fatty acids, and/or
wherein the concentrate is obtainable or obtained by a process comprising the steps:
(a) deesterification of fatty acid di- and/or triglycerides of a natural oil, preferably a marine oil, more preferably a fish oil and most preferably a tuna oil, wherein deesterification is by enzymatic cleavage or another process,
(b) isolation of selected fatty acids and removal of non-selected fatty acids, prefera- bly by distillation,
(c) reesterification of the isolated fatty acids into monoglycerides, diglycerides and triglycerides.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09163689.4 | 2009-06-24 | ||
EP09163689 | 2009-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010149759A1 true WO2010149759A1 (en) | 2010-12-29 |
Family
ID=42711128
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2010/059038 WO2010149759A1 (en) | 2009-06-24 | 2010-06-24 | Microparticles comprising a fat soluble fraction comprising dha and their production |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2010149759A1 (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102198116A (en) * | 2011-05-30 | 2011-09-28 | 何德海 | Preparation method of vitamin A microcapsules |
WO2014078912A1 (en) * | 2012-11-26 | 2014-05-30 | Progel Pty Ltd | Coating composition |
WO2014083124A1 (en) * | 2012-11-28 | 2014-06-05 | Dsm Ip Assets B. V. | Powderous formulation |
WO2014154788A1 (en) * | 2013-03-28 | 2014-10-02 | Dsm Ip Assets B. V. | Lutein composition suitable for infant food formulations |
CN104186976A (en) * | 2014-08-11 | 2014-12-10 | 嘉兴天和诚生物科技有限公司 | Vitamin A acetate beadlet and production method thereof |
WO2015087329A1 (en) * | 2013-12-12 | 2015-06-18 | Technion Research & Development Foundation Limited | Pectin based nanoparticles |
CN105582001A (en) * | 2015-12-25 | 2016-05-18 | 南京泛成生物化工有限公司 | Astaxanthin composition, preparation and preparation method of composition |
EP3000328A4 (en) * | 2013-05-20 | 2016-12-07 | Kao Corp | Fat composition |
US10188609B2 (en) | 2012-11-29 | 2019-01-29 | Progel Pty Ltd | Microparticles comprising a probiotic, cross-linkable reagent, a denatured protein, polyol plasticiser and trehalose |
WO2019025879A1 (en) * | 2017-08-04 | 2019-02-07 | Alsec Alimentos Secos S.A.S., | Nanoparticles comprising plant oil and proteins that are micro-encapsulated in powder |
CN109601641A (en) * | 2018-11-30 | 2019-04-12 | 南昌大学 | Phase cream and preparation method thereof in a kind of algae oil starch for preventing DHA from aoxidizing is high |
CN110408671A (en) * | 2019-07-24 | 2019-11-05 | 嘉必优生物技术(武汉)股份有限公司 | The method for being mixed schizochytrium and haematococcus pluvialis production DHA and astaxanthin |
EP3328214B1 (en) | 2015-07-29 | 2020-04-01 | Abbott Laboratories | Nutritional products having improved lipophilic solubility and bioavailability in an easily mixable form |
US10874116B2 (en) | 2015-04-30 | 2020-12-29 | Basf Se | Fortified jelly confectionery |
EP3677121A4 (en) * | 2017-09-01 | 2021-06-09 | Fuji Oil Holdings Inc. | Fat or oil composition containing unsaturated fatty acid |
WO2022074424A1 (en) | 2020-10-05 | 2022-04-14 | Prodia S.A.S. | Conditioner for doughs of baked and other bakery products, which replaces their fat content and process of production thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0385081A2 (en) * | 1989-02-09 | 1990-09-05 | Societe Des Produits Nestle S.A. | Dried fat emulsion product and method of producing the same |
EP0425213A2 (en) | 1989-10-23 | 1991-05-02 | Bocm Pauls Limited | Dry solid compositions containing lipid |
WO1994001001A1 (en) | 1992-07-06 | 1994-01-20 | Danochemo A/S | A microencapsulated oil or fat product |
EP0764405A2 (en) | 1995-09-20 | 1997-03-26 | Clintec Nutrition Company, An Illinois Partnership | Nutritional composition |
WO2003024237A1 (en) | 2001-09-13 | 2003-03-27 | Kao Corporation | Oil composition |
-
2010
- 2010-06-24 WO PCT/EP2010/059038 patent/WO2010149759A1/en active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0385081A2 (en) * | 1989-02-09 | 1990-09-05 | Societe Des Produits Nestle S.A. | Dried fat emulsion product and method of producing the same |
EP0425213A2 (en) | 1989-10-23 | 1991-05-02 | Bocm Pauls Limited | Dry solid compositions containing lipid |
WO1994001001A1 (en) | 1992-07-06 | 1994-01-20 | Danochemo A/S | A microencapsulated oil or fat product |
EP0764405A2 (en) | 1995-09-20 | 1997-03-26 | Clintec Nutrition Company, An Illinois Partnership | Nutritional composition |
WO2003024237A1 (en) | 2001-09-13 | 2003-03-27 | Kao Corporation | Oil composition |
Non-Patent Citations (1)
Title |
---|
HOGAN S A ET AL: "Microencapsulating properties of sodium caseinate", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US LNKD- DOI:10.1021/JF000276Q, vol. 49, no. 4, 1 January 2001 (2001-01-01), pages 1934 - 1938, XP002517843, ISSN: 0021-8561, [retrieved on 20010309] * |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102198116A (en) * | 2011-05-30 | 2011-09-28 | 何德海 | Preparation method of vitamin A microcapsules |
EP2922926A4 (en) * | 2012-11-26 | 2016-07-20 | Progel Pty Ltd | Coating composition |
WO2014078912A1 (en) * | 2012-11-26 | 2014-05-30 | Progel Pty Ltd | Coating composition |
WO2014083124A1 (en) * | 2012-11-28 | 2014-06-05 | Dsm Ip Assets B. V. | Powderous formulation |
US9918952B2 (en) | 2012-11-28 | 2018-03-20 | Dsm Ip Assets B.V. | Powderous formulation |
CN104812250A (en) * | 2012-11-28 | 2015-07-29 | 帝斯曼知识产权资产管理有限公司 | Powderous formulation |
US10188609B2 (en) | 2012-11-29 | 2019-01-29 | Progel Pty Ltd | Microparticles comprising a probiotic, cross-linkable reagent, a denatured protein, polyol plasticiser and trehalose |
EA029253B1 (en) * | 2013-03-28 | 2018-02-28 | ДСМ АйПи АССЕТС Б.В. | Lutein composition suitable for infant food formulations |
WO2014154788A1 (en) * | 2013-03-28 | 2014-10-02 | Dsm Ip Assets B. V. | Lutein composition suitable for infant food formulations |
CN105072926A (en) * | 2013-03-28 | 2015-11-18 | 帝斯曼知识产权资产管理有限公司 | Lutein composition suitable for infant food formulations |
AU2014243047B2 (en) * | 2013-03-28 | 2017-11-09 | Dsm Ip Assets B. V. | Lutein composition suitable for infant food formulations |
US11730704B2 (en) | 2013-03-28 | 2023-08-22 | Dsm Ip Assets B.V. | Lutein composition suitable for infant food formulations |
EP3000328A4 (en) * | 2013-05-20 | 2016-12-07 | Kao Corp | Fat composition |
WO2015087329A1 (en) * | 2013-12-12 | 2015-06-18 | Technion Research & Development Foundation Limited | Pectin based nanoparticles |
US9950003B2 (en) | 2013-12-12 | 2018-04-24 | Technion Research & Development Foundation Ltd. | Pectin based nanoparticles |
US10064888B2 (en) | 2013-12-12 | 2018-09-04 | Technion Research & Development Foundation Ltd. | Pectin based nanoparticles |
CN104186976A (en) * | 2014-08-11 | 2014-12-10 | 嘉兴天和诚生物科技有限公司 | Vitamin A acetate beadlet and production method thereof |
US10874116B2 (en) | 2015-04-30 | 2020-12-29 | Basf Se | Fortified jelly confectionery |
EP3328214B1 (en) | 2015-07-29 | 2020-04-01 | Abbott Laboratories | Nutritional products having improved lipophilic solubility and bioavailability in an easily mixable form |
CN105582001A (en) * | 2015-12-25 | 2016-05-18 | 南京泛成生物化工有限公司 | Astaxanthin composition, preparation and preparation method of composition |
WO2019025879A1 (en) * | 2017-08-04 | 2019-02-07 | Alsec Alimentos Secos S.A.S., | Nanoparticles comprising plant oil and proteins that are micro-encapsulated in powder |
EP3677121A4 (en) * | 2017-09-01 | 2021-06-09 | Fuji Oil Holdings Inc. | Fat or oil composition containing unsaturated fatty acid |
CN109601641A (en) * | 2018-11-30 | 2019-04-12 | 南昌大学 | Phase cream and preparation method thereof in a kind of algae oil starch for preventing DHA from aoxidizing is high |
CN110408671A (en) * | 2019-07-24 | 2019-11-05 | 嘉必优生物技术(武汉)股份有限公司 | The method for being mixed schizochytrium and haematococcus pluvialis production DHA and astaxanthin |
CN110408671B (en) * | 2019-07-24 | 2021-07-09 | 嘉必优生物技术(武汉)股份有限公司 | Method for producing DHA and astaxanthin by mixed culture of schizochytrium limacinum and haematococcus pluvialis |
WO2022074424A1 (en) | 2020-10-05 | 2022-04-14 | Prodia S.A.S. | Conditioner for doughs of baked and other bakery products, which replaces their fat content and process of production thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2010149759A1 (en) | Microparticles comprising a fat soluble fraction comprising dha and their production | |
Geranpour et al. | Recent advances in the spray drying encapsulation of essential fatty acids and functional oils | |
CN103037708B (en) | Nanoemulsion including sucrose fatty acid ester | |
McClements et al. | Structural design principles for delivery of bioactive components in nutraceuticals and functional foods | |
CN102131407B (en) | Compositions containing nono-polar compounds | |
Gallardo et al. | Microencapsulation of linseed oil by spray drying for functional food application | |
CN103190631B (en) | Non-aqueous pre-emulsion composition and preparation comprise the method for the beverage of phytosterol | |
US8173160B2 (en) | Compositions comprising edible oils and vitamins and/or minerals and methods for making the compositions | |
EP1843668B1 (en) | Powder compositions | |
CN102036572A (en) | Emulsions including a PEG-derivative of tocopherol | |
JP2009525755A (en) | Dietary supplement composition for blood lipid health | |
CA2961699C (en) | Fatty acid composition and method for fortifying nutritional products with fatty acids | |
JP2004538014A (en) | Methods of making oil-starch compositions and products thereof | |
WANASUNDARA et al. | Storage stability of microencapsulated seal blubber oil | |
WO2005089569A1 (en) | Extrusion-stable poly-unsaturated fatty-acid compositions for food products | |
US5853761A (en) | Stabilizing agent for oleaginous, physiologically active substances | |
JP3720375B2 (en) | Polyunsaturated fatty acid coated solid carrier particles for food | |
US20070031538A1 (en) | Liquid nutritional compositions containing n-3 polyunsaturated fatty acids | |
EP1280420B9 (en) | Natural vegetable oil concentrated in unsaponifiable matters as food ingredient | |
AU2016221293C1 (en) | Oil blends, processes for the preparation thereof and their use in formulas | |
Oyalo et al. | Health potential of Chia (Salvia hispanica L.) seeds-derived α-linoleic acid and α-linolenic acids: a review | |
Homroy et al. | Role of encapsulation on the bioavailability of omega‐3 fatty acids | |
Hermida et al. | Food applications of microencapsulated omega-3 oils | |
TWI242411B (en) | Method of preparing an unsaturated fatty acid dry concentrate | |
CN114158732A (en) | Polyunsaturated fatty acid triglyceride microcapsule powder and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10726105 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 10726105 Country of ref document: EP Kind code of ref document: A1 |