CN100536691C - Compositions containing coenzyme Q10 - Google Patents
Compositions containing coenzyme Q10 Download PDFInfo
- Publication number
- CN100536691C CN100536691C CNB2004800023313A CN200480002331A CN100536691C CN 100536691 C CN100536691 C CN 100536691C CN B2004800023313 A CNB2004800023313 A CN B2004800023313A CN 200480002331 A CN200480002331 A CN 200480002331A CN 100536691 C CN100536691 C CN 100536691C
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- Prior art keywords
- fatty acid
- composition
- acid ester
- polyol fatty
- present
- Prior art date
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- 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 title claims abstract description 325
- 239000000203 mixture Substances 0.000 title claims abstract description 226
- 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 title claims abstract description 118
- 235000017471 coenzyme Q10 Nutrition 0.000 title claims abstract description 117
- 229940110767 coenzyme Q10 Drugs 0.000 title claims abstract 21
- -1 fatty acid ester Chemical class 0.000 claims abstract description 154
- 239000000194 fatty acid Substances 0.000 claims abstract description 151
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 146
- 229930195729 fatty acid Natural products 0.000 claims abstract description 146
- 235000013305 food Nutrition 0.000 claims abstract description 87
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 8
- 229920005862 polyol Polymers 0.000 claims description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 96
- 238000002360 preparation method Methods 0.000 claims description 92
- 239000002245 particle Substances 0.000 claims description 41
- 238000002156 mixing Methods 0.000 claims description 13
- 229960003656 ricinoleic acid Drugs 0.000 claims description 9
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 7
- 229920000223 polyglycerol Polymers 0.000 claims 2
- 235000004443 Ricinus communis Nutrition 0.000 claims 1
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- 229960004747 ubidecarenone Drugs 0.000 description 93
- 238000003756 stirring Methods 0.000 description 61
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 58
- 230000010148 water-pollination Effects 0.000 description 56
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- 238000004945 emulsification Methods 0.000 description 41
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- 239000000126 substance Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 18
- 239000007788 liquid Substances 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- 239000003995 emulsifying agent Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
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- 239000000463 material Substances 0.000 description 11
- 229940066675 ricinoleate Drugs 0.000 description 11
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 11
- 239000002609 medium Substances 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 238000010241 blood sampling Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000004321 preservation Methods 0.000 description 9
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 9
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- 238000002425 crystallisation Methods 0.000 description 7
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- 235000014347 soups Nutrition 0.000 description 7
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 244000269722 Thea sinensis Species 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 6
- 239000004519 grease Substances 0.000 description 6
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- 239000008267 milk Substances 0.000 description 6
- 210000004080 milk Anatomy 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 235000006468 Thea sinensis Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000020279 black tea Nutrition 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000013353 coffee beverage Nutrition 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical class CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 5
- 238000001694 spray drying Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 240000004371 Panax ginseng Species 0.000 description 4
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 4
- 235000003140 Panax quinquefolius Nutrition 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
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- 239000000284 extract Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 235000008434 ginseng Nutrition 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000013558 reference substance Substances 0.000 description 4
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- 239000000725 suspension Substances 0.000 description 4
- 235000013616 tea Nutrition 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- LRPFVGWWAKSVOY-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)CC(O)(C(O)=O)CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O LRPFVGWWAKSVOY-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- LWMGQNYWJFCJJF-UHFFFAOYSA-N OCC(O)CO.CC(=O)OC(=O)C(O)C(O)C(=O)OC(C)=O.CCCCCCCCCCCCCCCCCC(O)=O Chemical compound OCC(O)CO.CC(=O)OC(=O)C(O)C(O)C(=O)OC(C)=O.CCCCCCCCCCCCCCCCCC(O)=O LWMGQNYWJFCJJF-UHFFFAOYSA-N 0.000 description 3
- 241001249696 Senna alexandrina Species 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 235000010443 alginic acid Nutrition 0.000 description 3
- 229920000615 alginic acid Polymers 0.000 description 3
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- 238000003556 assay Methods 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
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- 238000009826 distribution Methods 0.000 description 3
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- UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
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- 238000002844 melting Methods 0.000 description 3
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- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
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- 150000007949 saponins Chemical class 0.000 description 3
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- 239000004094 surface-active agent Substances 0.000 description 3
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 2
- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 2
- CPTAWIKLJZKYSK-UHFFFAOYSA-N 2-hydroxypropanoic acid;octadecanoic acid;propane-1,2,3-triol Chemical compound CC(O)C(O)=O.OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CPTAWIKLJZKYSK-UHFFFAOYSA-N 0.000 description 2
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- GGDUFVMSYGVEMJ-UHFFFAOYSA-N butanedioic acid;octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)CCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O GGDUFVMSYGVEMJ-UHFFFAOYSA-N 0.000 description 2
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- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 1
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention provides a coenzyme Q10-containing composition comprising a coenzyme Q10 and a hydrophilic fatty acid ester of a polyhydric alcohol; a coenzyme Q10-containing composition comprising a coenzyme Q10, a lipophilic fatty acid ester of a polyhydric alcohol and a hydrophilic fatty acid ester of a polyhydric alcohol; and a food or beverage comprising the coenzyme Q10-containing composition as defined above.
Description
Technical field
The present invention relates to a kind of composition that contains Co-Q10 that is specially adapted in the field of food.
Background technology
Co-Q10 (CoQ10) is also referred to as ubidecarenone, ubiquinone-10 etc., is used as pharmaceuticals uses such as metabolic cardiotonic according to its unique physiological action.In addition, at home, along with the change of the viewpoint that the food medicine is distinguished, it is used to food applications has become possibility, and can expect its application in field of health care food.Particularly the achievement in research to CoQ10 is remarkable in recent years; myocardium protecting action, anti-cancer, the anti-aging effect that causes except the antioxidation of CoQ10, suppress in the blood the LDL oxidation, also report has the oxygen transfer efficiency that suppresses blood pressure and raise, improve ischemic myocardium, the ATP that activates myocardial mitochondria to synthesize, improve cardiac function etc.But CoQ10 is yellow～orange solid at normal temperatures, and is water-soluble hardly, pure, and also is insoluble in oil, therefore in food applications extremely difficulty be widely used, the application that particularly has aspect beverage is subjected to greatly limiting shortcoming.
Preparation method as CoQ10, known have with CoQ10, emulsifying agent, polyalcohol and water mix the back, carry out HIGH PRESSURE TREATMENT make liposoluble substance the water-based liquor the preparation method (for example, open the 2000-212066 communique referring to the spy), use the polyoxyethylene sorbitan monoleate to carry out liquefiable method (for example, showing the 2001-504343 communique) etc. referring to the spy.But the water-based liquor that adopts the former approach preparation is for utilizing 1000kg/cm
2The water-based liquor of the disposable acquisition CoQ10 of ultra high pressure treatment, but poor stability, and through the time separate out the crystallization of white casse or CoQ10.In addition,, use the polyoxyethylene sorbitan monoleate, consider, will generate the high accessory substance of toxicity in the synthetic reaction of this type of ethylene oxide surfactant, therefore be not preferred for food applications from its manufacturing step aspect according to the latter's method.
In addition, preparation as the organism absorptivity that has improved CoQ10, carry out after having proposed to add the CoQ10 after the heat of solution in the edible oil after the heating or in edible oil, having added CoQ10 heating for dissolving, then cool off obtain, CoQ10 that CoQ10 disperses with crystal habit and the mixture (for example, opening the 2003-125734 communique) of edible oil referring to the spy.But this preparation can not directly be added in the aqueous food.
Summary of the invention
Purpose of the present invention is for providing a kind of storage stability good and improved bioabsorbable, the composition that contains CoQ10 that is applicable to food applications of CoQ10.
Promptly, the invention provides
(1) a kind of composition that contains Co-Q10, it contains Co-Q10 and hydrophily polyol fatty acid ester;
(2) above-mentioned (1) described composition that contains Co-Q10, wherein, the hydrophily polyol fatty acid ester is single glycerine fatty acid organic acid esters and/or polyglycereol condensation ricinoleate;
(3) the described composition that contains auxilliary pure Q10 in above-mentioned (1) or (2), wherein, the HLB of hydrophily polyol fatty acid ester is more than 8;
(4) each described composition that contains Co-Q10 of above-mentioned (1)～(3) is characterized by, and compares with the situation of independent use Co-Q10, and said composition is to have improved the bioabsorbable Co-Q10 high-absorbable composition of Co-Q10;
(5) a kind of composition that contains Co-Q10, said composition contains Co-Q10, lipophile polyol fatty acid ester and hydrophily polyol fatty acid ester;
(6) a kind of composition that contains Co-Q10, said composition is made via following step: form the 1st step of Co-Q10 and the compound of lipophile polyol fatty acid ester, with this compound that obtains in the 1st step and the 2nd step of hydrophily polyol fatty acid ester mixing.
(7) above-mentioned (5) or (a 6) described composition that contains Co-Q10, wherein, the emulsified or solvable oil-in-water type that turns to of said composition.
(8) above-mentioned (7) described composition that contains Co-Q10, wherein, the average emulsification particle diameter of emulsified particle is below the 300nm.
(9) each described composition that contains Co-Q10 in above-mentioned asking (5)～(8), wherein, the HLB of lipophile polyol fatty acid ester is below 6, the HLB of hydrophily polyol fatty acid ester is more than 8.
(10) each described Foods or drinks that contains the composition of Co-Q10 of a kind of above-mentioned (1)～(9).
(11) each described hydrophily polyol fatty acid ester that is used to prepare the composition that contains Co-Q10 of a kind of above-mentioned (1)～(4).
(12) be used to prepare the purposes of the hydrophily polyol fatty acid ester of each described composition that contains Co-Q10 of above-mentioned (1)～(4).
Description of drawings
Fig. 1 is illustrated in the bioabsorbable test 1, gives behind the rat curve map of the measurement result of the Co-Q10 concentration in the blood plasma in 1～24 hour with each test specimen.
Fig. 2 is for being illustrated in the bioabsorbable test 2, each test specimen being given among test A and A ' and contrast test B and the B ' behind the rat curve map of the measurement result of the Co-Q10 concentration in the blood plasma in 1～24 hour.
The specific embodiment
The composition of CoQ10 that contains of the present invention is roughly by 2 kinds of forecast scheme configurations.The 1st kind of scheme is the composition that contains CoQ10 and hydrophily polyol fatty acid ester (following, be called the 1st kind of composition of the present invention), and the 2nd kind of scheme is the composition that contains CoQ10, lipophile polyol fatty acid ester and hydrophily polyol fatty acid ester (following, be called the 2nd kind of composition of the present invention).In addition, in this specification, also the 1st kind of composition of the present invention and the 2nd kind of composition of the present invention are collectively referred to as composition of the present invention sometimes.In addition, also the preparation of the composition of the CoQ10 of containing of the present invention is called " ubidecarenone preparation " sometimes.Below, the composition of each scheme is described successively.
(1) the 1st kind of composition of the present invention
One of key character of the 1st kind of composition of the present invention contains CoQ10 and hydrophily polyol fatty acid ester for said composition.
The form of said composition is not particularly limited, from consideration easy to use, and preferred particulates shape, Powdered or aqueous.The problem that graininess or pulverous preparation do not exist existing C oQ10 to separate out, storage stability is good.Even under the situation of liquid state, CoQ10 also can maybe can be dissolved by the emulsification stably of hydrophily polyol fatty acid ester, for example, when said composition is preserved under conditions such as room temperature, the crystallization of CoQ10 also is difficult to separate out, and is same with preparations such as graininess, has good storage stability.And the 1st composition of the present invention can make by maybe dissolving in the medium-term and long-term stable emulsification of water.
When making said composition emulsification maybe can be dissolved in water, the average emulsification particle diameter of the emulsified particle of CoQ10 is not particularly limited, be generally 1nm～10000nm, from improving bioabsorbable consideration, be preferably 1nm～5000nm, more preferably 1nm～1000nm, more preferably 1nm～500nm, most preferably be 1nm～100nm.
Average emulsification particle diameter for example can adopt laser refraction type particle size distribution device (NICOMP MODEL370, Particle Sizing Systems society system) to measure.
But emulsification or solvation by the hydrophily polyol fatty acid ester, the crystallization that can suppress the CoQ10 that contains in the 1st kind of composition of the present invention, therefore, can infer that said composition is the composition that is in the monodisperse status that is suitable for absorbing when being absorbed by organism.Therefore, the bioabsorbable height of the CoQ10 in the 1st kind of composition of the present invention.In addition, infer CoQ10, so CoQ10 is continued to absorb in vivo by the tunicle of hydrophily polyol fatty acid ester parcel.
The 1st kind of composition of the present invention can use usually in field of food widely used raw material to make, therefore applicable to food applications.Even said composition is added in the aqueous medium, CoQ10 does not in fact take place yet to separate out, therefore, can be advantageously used in particularly being difficult at present adopt in the aqueous foods such as beverage of CoQ10.
CoQ10 is meant to have the isoprene chain that is made of 10 isoprene units quinone derivatives as side chain, extensively is distributed in occurring in nature.In animals and plants etc., participate in Intramitochondrial oxidative phosphorylation electron transport system.As the CoQ10 of use of the present invention, so long as can be organism, for example, the material that the people absorbed in the mammal gets final product, and is not particularly limited.As this CoQ10, for example, normally used industrial composite be can enumerate, the thalline extracts such as yeast extract that fermentation method obtains, the extract that from animals and plants such as sardine, pig, ox, chicken, cabbage, eggplant, garlic, Chinese cabbage, extracts etc. utilized, above-mentioned substance can be used alone, can also be 2 or more kinds in combination respectively.The preferred yeast extract that obtains by fermentation method that uses.
In addition, because there is the isoprene chain that constitutes with 1～12 isoprene unit coenzyme (CoQ1～12) as side chain in occurring in nature, therefore, only otherwise influence realizes the desirable effect of the present invention, also can comprise the different analog of the above-mentioned isoprene chain length of part among the CoQ10 of the present invention.
It is more than 8 that " hydrophily " of the hydrophily polyol fatty acid ester that uses among the present invention typically refers to HLB.Mainly consider from the application aspect of aqueous food, HLB is preferably more than 8, more preferably more than 9.5, more preferably more than 11.Herein, " HLB is about 8 " is not to be meant that HLB 8 is meant that being enough at least to bring into play with HLB is the HLB value of the desirable effect of the present invention of 8 polyol fatty acid ester same degree.The computational methods of HLB are not particularly limited in this specification, for example can adopt following existing method etc. to calculate.
In addition, in the composition of the present invention, sometimes use hydrophily polyol fatty acid ester and HLB less than about 8, can regard following lipophile polyol fatty acid ester as with " hydrophily " described in this specification, the HLB of employed ester is as the mean value of total HLB of two esters (promptly, the summation of the HLB of each ester molecule that uses in the composition obtain divided by the ester molecule sum value) when calculating, mean value is more than about 8, be preferably more than 8 especially, more preferably more than 9.5, wherein, most preferably be more than 11.
Generally speaking, HLB is the hydrophily of expression emulsifying agent and the yardstick of lipophile (hydrophobicity) degree, and the strong more value of being somebody's turn to do of hydrophily is big more.The computational methods of HLB are not particularly limited.As hydrophily polyol fatty acid ester of the present invention, for example, can use through showing the material of at least a kind of method affirmation possess hydrophilic property in the HLB computational methods down.In addition, " HLB is more than 8 " is meant that HLB that any method in following method is tried to achieve is the situation more than 8 among the present invention.Equally, the preferable range of HLB is more than 9.5, more preferably more than 11.
As the computational methods of HLB, for example, can adopt GRIFFIN formula existing the whole bag of tricks such as (following formulas).
HLB=20 * (molecular weight of hydrophilic segment)/(total molecular weight of emulsifying agent)
Hydrophilic segment in the above-mentioned formula is meant the part of removing hydrocarbon chain from the whole molecules that constitute emulsifying agent (being polyol fatty acid ester this specification).In addition, when using ester emulsifying agent, can calculate by saponification number and the acid number that constitutes aliphatic acid by following formula.
HLB＝20×(1-S/A)
S: saponification number, A: the acid number that constitutes aliphatic acid
In addition, only containing polyoxyethylene chain can be calculated by following formula as the material of hydrophilic radical.
HLB＝E/5
E: the part by weight of polyoxyethylene group
Except the aforementioned calculation method, can obtain HLB by experiment.That is, emulsifying agent and the unknown emulsifying agent known to HLB make up, grease and water and milkization that HLB is known, and the mixing ratio of selection emulsified state the best is calculated by following formula.
{(Wu×HLBu)+(Wa×HLBa)}/{Wu+Wa}＝HLBo
The emulsifying agent part by weight of Wu:HLB the unknown
The emulsifying agent part by weight that Wa:HLB is known
The HLB of the emulsifying agent of HLBu:HLB the unknown (HLB of the emulsifying agent of obtaining)
The HLB of the emulsifying agent that HLBa:HLB is known
HLBo: the essential HLB of grease
Polyalcohol is meant with the alcohol that has 2 above hydroxyls in a part.Polyalcohol is not particularly limited, for example, and the alcohol that can constitute by monomer for glycerine and so on, the also alcohol that can constitute by polymer for polyglycereol and so on.The aggregate number (degree of polymerization) that constitutes the monomer of polymer is not particularly limited.In addition, when employed hydrophily polyol fatty acid ester was made of the mixture of multiple hydrophily polyol fatty acid ester, the degree of polymerization of the polyalcohol of employed this ester can be used as the mean value of the degree of polymerization of various esters and tries to achieve.
Formation aliphatic acid as polyol fatty acid ester is not particularly limited, and can be the saturated or unrighted acid of straight or branched.In addition, the kind that constitutes aliphatic acid also is not particularly limited, and also can comprise aliphatic acid more than a kind or 2 kinds in a kind of polyol fatty acid ester.
Among the present invention, preferred use can be used for the hydrophily polyol fatty acid ester of food.As its concrete example, can enumerate fatty acid glyceride classes such as single glycerine fatty acid organic acid esters, polyglyceryl fatty acid ester, polyglycereol condensation ricinoleate; The sorbitan fatty acid esters class; The sucrose fatty ester class; The lecithin class; Chinese honey locust glycosides etc., above-mentioned substance may be used alone, can also be 2 or more kinds in combination.Wherein, be recrystallized owing to can suppress CoQ10 effectively, therefore preferred single glycerine fatty acid organic acid esters of use and/or polyglycereol condensation ricinoleate are as the hydrophily polyol fatty acid ester.
As above-mentioned single glycerine fatty acid organic acid esters; for example; preferred single glycerine stearic acid citrate, single glycerine stearic acid succinate, the sad succinate of single glycerine, single glycerine stearic acid lactate, the single glycerine stearic acid diacetyl tartrate etc. of using; wherein, more preferably use single glycerine stearic acid citrate, single glycerine stearic acid diacetyl tartrate.
As above-mentioned polyglyceryl fatty acid ester, the carbon number that for example, the average degree of polymerization that preferably uses polyglycereol is 2～10, constitute aliphatic acid is 6～22 aliphatic acid.As the concrete example of polyglyceryl fatty acid ester, preferably use the triglycerin monolaurate, triglycerin list myristinate, Triglyceryl monooleate, the triglycerin monostearate, SUNSOFT A-141E, five myristins, five glycerin mono-fatty acid esters, SUNSOFT A-173E, Pentaglycerin monostearate, five glycerol tristearates, Pentaglycerin monostearate, six Monooctamoins, six glycerine dicaprylates, six glyceryl monolaurates, six monomyristins, six glycerin mono-fatty acid esters, six glyceryl monostearates, DECAGLYCERYL MONOLAURATE, ten monomyristins, SY-Glyster MO 750, ten glycerine monopalmitates, SY-Glyster MSW 750, ten glycerol distearates etc.
As above-mentioned polyglycereol condensation ricinoleate, for example, the average degree of polymerization that preferably uses polyglycereol is 2～10, the average condensation degree (the average condensation number of ricinoleic acid) of poly-ricinoleic acid is 2～4 material.Particularly, more preferably use four glycerine condensation ricinoleates, five glycerine condensation ricinoleates, six glycerine condensation ricinoleates, two glycerine condensation ricinoleates etc.
As above-mentioned sorbitan fatty acid esters class, for example, preferably use sorbitan monostearate, dehydrated sorbitol mono-fatty acid ester etc.
As above-mentioned sucrose fatty ester class, for example, preferably use sucrose palmitate, sucrose stearate etc.
As above-mentioned lecithin class, for example, preferably use soybean lecithin, egg yolk lecithin, enzymolysis lecithin etc.
As above-mentioned Chinese honey locust glycoside, for example, preferably use Fructus Sophorae glycosides, soapbark saponin, soybean saponin, yucca saponin etc.
The total content of CoQ10 and hydrophily polyol fatty acid ester is not particularly limited in the 1st kind of composition of the present invention, is preferably 1～60 weight %, 3～40 weight % more preferably.In addition, as the weight ratio of CoQ10 and hydrophily polyol fatty acid ester, with respect to 100 weight portion CoQ10, the hydrophily polyol fatty acid ester is preferably 10～5000 weight portions, more preferably 40～3500 weight portions, 40～500 weight portions more preferably.
In order to prepare the 1st kind of composition of the present invention, use above-mentioned hydrophily polyol fatty acid ester.Therefore, as a kind of scheme of the present invention, comprise the 1st kind of preparation of compositions of the present invention with the hydrophily polyol fatty acid ester and the application that is used to prepare the hydrophily polyol fatty acid ester of the 1st kind of composition of the present invention.
In addition, also can contain other compositions in the 1st kind of composition of the present invention.As other compositions, for example, can enumerate water, lipophile polyol fatty acid ester, grease, liposoluble substance, polyol fatty acid ester emulsifying agent in addition etc.
Be not particularly limited for water, for example, can enumerate running water, distilled water, deionized water etc.Water preferably uses the medium that can obtain the liquid present composition.In addition, medium is not limited in water.For example,, be not particularly limited, can use wherein a kind, also can use the mixture more than 2 kinds so long as the medium that ethanol, glycerine, propane diols, liquid sugar etc. can easily add in the aqueous food gets final product.
As the lipophile polyol fatty acid ester, can enumerate the ester that uses in the 2nd kind of composition for example of the present invention.When using the lipophile polyol fatty acid ester, can be dissolved in advance in the lipophile polyol fatty acid ester by for example making CoQ10, thereby use with liquid state.In addition, during long preservation the 1st kind of composition of the present invention, can expect to suppress effectively CoQ10 crystallization takes place.
As above-mentioned grease, liposoluble substance, can enumerate liposoluble substances such as following grease, vitamins from animals and plants etc.In addition, as the emulsifying agent beyond the polyol fatty acid ester, can enumerate polyol fatty acid ester any known emulsifying agent in addition.
With the 1st kind of composition of the present invention, for example be that medium is made when aqueous with water, also can contain the stabilizing agent that is generally used for food, preservative agent, pH conditioning agent etc. as other compositions.By containing described stabilizing agent etc., can improve the emulsion stability of CoQ10, the result can further improve the storage stability of the 1st kind of composition of the present invention.In addition, the 1st kind of composition of the present invention made graininess or when Powdered, for example, also can be contained water soluble excipients such as dextrin, cyclodextrin, alginic acid Na, lactose, galactooligosacchari(es, galactomannans zymolyte, casein, xanthans.Described excipient can make the 1st kind of composition of the present invention stabilisation under drying regime, and said composition can be dissolved in water etc.
The content of other compositions is not particularly limited in the 1st kind of composition of the present invention, also can suitably adjust in not influencing the scope of expressing the desired effect of the present invention.
The 1st kind of composition of the present invention made when aqueous, the hydrophily polyol fatty acid ester is dissolved in the medium (for example, water), under agitation add CoQ10 and make its emulsification, be prepared thus.The dissolving of hydrophily polyol fatty acid ester in medium can mix, heat after maybe being added on this ester in the medium its dissolving is got final product by this ester being added to be heated in this medium more than ester fusing point.Stirring and emulsification can use for example oar formula stirring, PHYSCOTRON, mulser (HOMOMIXER), homogenizer, high-pressure homogenizer, bead mill to wait and carry out.In addition, the interpolation sequential scheduling of CoQ10 and hydrophily polyol fatty acid ester is not particularly limited.In addition, other compositions such as aforementioned stable agent are as long as add in the reasonable time point in the preparation of compositions step.In addition, in the step of emulsification CoQ10, (carbon number: 6～8) greases such as animal raw fat of Synthetic Oil such as fatty acid triglycercide or the common vegetative grease that obtains from soybean, rice, vegetable seed, cocoa bean, coconut, sesame, safflower, palm, cotton, peanut, avocado, common bombax flower, leaf mustard, burdock, wheat, evening primrose, camellia, maize, sunflower etc. and acquisition from ox, breast, pig, sardine, mackerel, shark, saury, cod etc. make CoQ10 suspendible or dissolving also can to utilize medium chain in advance.Then, also can be in the emulsifying step of CoQ10, make CoQ10 with
Carotenoidses such as carrotene, lycopene, astaxanthin, zeaxanthin; Together emulsifications of liposoluble substances such as vitamins such as vitamin A, vitamin E, vitamin K, vitamin D are by also can further improving emulsion stability and the oxidation stability of CoQ10 with above-mentioned substance.
The 1st kind of composition of the present invention made when Powdered, can be with for example (for example as the above-mentioned water soluble excipient of other compositions, dextrin) (for example is dissolved in medium in advance, water) in, under agitation, add the liquid composition that obtains as described above and make its emulsification, be prepared through suitable drying.The use level of this excipient is not particularly limited, and with respect to the 1st kind of composition 100 weight portions of the present invention, is preferably about 5～90 weight portions, more preferably about 10～50 weight portions.The interpolation sequential scheduling of excipient and liquid composition is not particularly limited.Drying means is not particularly limited, and for example, can enumerate spray-drying, freeze drying, dull and stereotyped drying etc., considers preferably spray drying from the aspects such as simplicity of drying.
In addition, when the 1st kind of composition of the present invention made graininess, for example can use comminutor such as showering curtain type coating machine that the powdered composition that obtains is carried out grain forming and be prepared.
Can make the 1st kind of composition of the present invention (still, the 1st kind of preparation of compositions method of the present invention is not limited to said method) through aforesaid operations and all have good storage stability.Wherein, the storage stability of graininess, pulverous composition is high.And, even when for example adding in the water once more, but also can present and the good emulsifying or the melting state of the composition same degree that obtains with liquid condition.
The 1st kind of composition of the present invention can be the composition that obtains with liquid condition naturally, also can be with graininess, the Powdered composition that obtains, give organism with said composition, when CoQ10 is absorbed by organism, because CoQ10 is emulsified maybe can be dissolved, crystallization takes place in it can to infer abundant inhibition.Therefore, the bioabsorbable situation that is higher than independent use CoQ10 of the CoQ10 in the 1st kind of composition of the present invention.Therefore,, can provide a kind of composition according to the present invention, said composition with only compare for the situation of CoQ10, improved the bioabsorbable of CoQ10, be CoQ10 high-absorbable composition.
(2) the 2nd kind of composition of the present invention
The 2nd kind of composition of the present invention contains CoQ10, lipophile polyol fatty acid ester and hydrophily polyol fatty acid ester.
Operable CoQ10, hydrophily polyol fatty acid ester, other compositions and above-mentioned preferred version etc. are identical with above-mentioned the 1st kind of composition of the present invention in the said composition.In addition, the preferred version of said composition is also identical with above-mentioned the 1st kind of composition of the present invention.
The 2nd kind of composition of the present invention be CoQ10 be stabilized ground emulsification or liquefiable, storage stability is good contains the CoQ10 composition, and its emulsification in water maybe can be dissolved.Said composition can be added on various food, does not particularly increase the white casse degree in beverage, and does not precipitate, and can keep its form steadily in the long term.
In the 2nd kind of composition of the present invention, different with the 1st kind of composition of the present invention, the lipophile polyol fatty acid ester is used as one of essential composition.
As the lipophile polyol fatty acid ester that uses in the 2nd kind of composition of the present invention, preferably have dispersion stably, emulsification or be dissolved in the character of fat in mutually, can be used for the material of food.Herein, " lipophile " typically refers to HLB less than about 8.This definition is in order to distinguish mutually with above-mentioned " hydrophily ", and " about less than 8 " is not strict.
The HLB of lipophile polyol fatty acid ester is not particularly limited, preferred less than 8, more preferably 6 below, further preferred below 4.
The lipophile polyol fatty acid ester is not particularly limited, the preferred material with nonionic surface active agent effect that uses.
As the lipophile polyol fatty acid ester that uses among the present invention, particularly, can enumerate single fatty acid monoglycerides such as single glyceryl monostearate, single glycerin mono-fatty acid ester, single monomyristin, single Monooctamoin, single glyceryl monolaurate, single Glyceryl monobehenate, single glycerine list mustard seed acid esters; Single dialycerides fat acid esters such as single glycerol distearate, single diolein, single glycerine dicaprylate, single dilaurin; Single glycerine fatty acid organic acid esters such as single glycerine stearic acid citrate, single glycerine stearic acid acetic acid esters, SUNFAT U-12, single glycerine stearic acid succinate, the sad succinate of single glycerine, single glycerine stearic acid lactate, single glycerine stearic acid diacetyl tartrate; Single glycerine tallow fixed oil fat acid esters, single glycerine vegetable seed fixed oil fat acid esters, single glycerine soybean hardened oil fatty acid ester, single glycerine cottonseed oil fatty acid ester, the mono-fatty acid glyceride that the various greases of employing such as single glycerine safflower oil fatty acid ester obtain, average degree of polymerization is that 2～10 polyglycereol and carbon number are the polyglyceryl fatty acid esters such as ester that 6～22 aliphatic acid forms, and average degree of polymerization is that 2～10 polyglycereol and condensation degree are the fatty acid glyceride classes such as polyglycereol condensation ricinoleate such as ester that 2～4 poly-ricinoleic acid forms; Propylene glycol monostearate, propylene glycol mono-oleate, and methyl glycol fatty acid ester class such as PGML; Dehydrated sorbitol distearate, sorbitan tristearate, NOFABLE SO-992, sorbitan dioleate, and sorbitan fatty acid esters class such as sorbitan trioleate; And the mixture of selecting in the lecithin class such as soybean lecithin, egg yolk lecithin, enzymolysis lecithin more than a kind or 2 kinds.Wherein, the mixture of preferably from the fatty acid glyceride class, selecting more than a kind or 2 kinds; more preferably single fatty acid monoglyceride; single dialycerides fat acid esters; single glycerine fatty acid organic acid esters (particularly single glycerine fatty acid acetic acid esters; SUNFAT U-12); the mixture of selecting in polyglyceryl fatty acid ester (particularly average degree of polymerization is that 2～10 polyglycereol and carbon number are the ester that 6～22 aliphatic acid forms) and the polyglycereol condensation ricinoleate (particularly average degree of polymerization is that 2～10 polyglycereol and condensation degree are the ester that 2～4 poly-ricinoleic acid forms) more than a kind or 2 kinds; further preferred single glycerine fatty acid organic acid esters (particularly single glycerine fatty acid acetic acid esters; SUNFAT U-12); as concrete example, can enumerate 50% acetylate of single glyceryl monostearate; the complete acetylate of coconut hardened oil monoglyceride.Above-mentioned lipophile polyol fatty acid ester all can use separately, or uses mixing more than 2 kinds.In addition, when using polyglyceryl fatty acid ester as the lipophile polyol fatty acid ester, be not particularly limited, compound for following lipophile polyol fatty acid ester and CoQ10, from forming stable oil-in-water type emulsion particle, maybe can dissolve state aspect and consider, preferred esterification degree is more than 75% or HLB is any material below 4.
The 2nd kind of composition of the present invention uses above-mentioned lipophile polyol fatty acid ester, therefore as a kind of scheme of the present invention, comprise the 2nd kind of preparation of compositions of the present invention with the lipophile polyol fatty acid ester and the purposes that is used to prepare the lipophile polyol fatty acid ester of the 2nd kind of composition of the present invention.
In the 2nd kind of composition of the present invention, the total content of CoQ10, lipophile polyol fatty acid ester and hydrophily polyol fatty acid ester is not particularly limited, and is preferably 2～60 weight %, 5～50 weight % more preferably.In addition, weight ratio as CoQ10 and lipophile polyol fatty acid ester, with respect to 100 weight portion CoQ10, the lipophile polyol fatty acid ester is preferably 25～2000 weight portions, more preferably 50～1000 weight portions, 100～500 weight portions more preferably.In addition, weight ratio as CoQ10 and hydrophily polyol fatty acid ester, with respect to 100 weight portion CoQ10, the hydrophily polyol fatty acid ester is preferably 50～10000 weight portions, more preferably 100～5000 weight portions, 200～2000 weight portions more preferably.
The 2nd kind of composition of the present invention mixes above-mentioned CoQ10, lipophile polyol fatty acid ester and hydrophily polyol fatty acid ester and obtains, compound for following lipophile polyol fatty acid ester and CoQ10, from forming stable oil-in-water type emulsion particle, maybe can dissolving the state aspect consideration, the HLB of the lipophile polyol fatty acid ester that use this moment is below 6, and the HLB of hydrophily polyol fatty acid ester is preferably more than 8.
The 2nd kind of composition of the present invention can be prepared as follows, and particularly, can the mixing of hydrophily polyol fatty acid ester, stirring be prepared by CoQ10 and lipophile polyol fatty acid ester are mixed, stir again.Heating condition during stirring is preferably 40～90 ℃, and more preferably 50～80 ℃, more preferably 60～75 ℃.In addition, stirring means is not particularly limited, and can suitably utilize the stirring of oar formula, mulser, homogenizer etc., considers from stirring efficiency and operability aspect, preferably utilizes mulser.
The method for making of the 2nd kind of composition of the present invention is not particularly limited, and said composition for example preferably is prepared through following 2 steps:
Mixed C oQ10 and lipophile polyol fatty acid ester, form CoQ10 and lipophile polyol fatty acid ester compound the 1st step and
Mix this compound that obtains in the 1st step and the 2nd step of hydrophily polyol fatty acid ester.
The use level of CoQ10 in above-mentioned the 1st step is not particularly limited, and in this compound, the amount of CoQ10 is preferably 1～50 weight %, more preferably 5～40 weight %, 10～30 weight % more preferably.By cooperating the CoQ10 of described use level, finally can obtain containing the compositions desired of the CoQ10 that brings into play the necessary abundant content of its function.
Obtain the compound (following, be called compound) of CoQ10 and lipophile polyol fatty acid ester in above-mentioned the 1st step.Particularly, the lipophile polyol fatty acid ester is heated to 40～90 ℃, adds CoQ10 while stirring, prepare transparent complex solution thus.In addition, the fusing point of CoQ10 is about 48 ℃, in order significantly to shorten preparation compound required time, and, consider the heat endurance of CoQ10 preferably to be heated to 50～80 ℃, more preferably be heated to 60～75 ℃.In addition, when using the high-melting-point material in the lipophile polyol fatty acid ester, preferably can both remain on more than the fusing point of this material until following emulsifying step of the present invention.In addition, infer that this compound has the form that the alkyl chain that is present in intramolecular 10 isoprene side chains of CoQ10 and lipophile polyol fatty acid ester combines with one another.In addition, the stirring means in the 1st step is not particularly limited, and can suitably utilize the stirring of oar formula, mulser, homogenizer etc., considers from stirring efficiency and operability aspect, preferably utilizes mulser.
In above-mentioned the 2nd step, further use the hydrophily polyol fatty acid ester, formation with this stable composite be emulsified into the system of oil-in-water type drop.Particularly, as long as will be heated to this compound of 40～90 ℃ and the hydrophily polyol fatty acid ester mixes, stirs.The heating condition of this compound is preferably 50～80 ℃, more preferably 60～75 ℃.For the hydrophily polyol fatty acid ester, there is no special temperature conditions and limit, the operability aspect from mix and stir is considered, preferably is heated to 40～90 ℃.And, this compound and hydrophily polyol fatty acid ester are stirred, the temperature in the stirring is preferably 40～90 ℃, more preferably 50～80 ℃, more preferably 60～75 ℃.In addition, the stirring means in the 2nd step is not particularly limited, and can suitably utilize the stirring of oar formula, mulser, homogenizer etc., considers from stirring efficiency and operability aspect, preferably utilizes mulser.
The hydrophily polyol fatty acid ester that uses in the 2nd step of the present invention with respect to compound 1 weight portion that obtains in the 1st step of the present invention, preferably cooperates 1.5～5 weight portions, more preferably cooperates 2～3 weight portions.By in this compound, cooperating the hydrophily polyol fatty acid ester in this scope, finally obtain the desired combined thing, in the said composition, infer that this compound by the tunicle of hydrophily polyol fatty acid ester parcel, can continue to discharge CoQ10.
And, in the present invention, the emulsifying mixture that obtains in the 2nd step is become oil-in-water type drop (emulsifying step).When being emulsified into the oil-in-water type drop, in aqueous matrix, add the hydrophilic surfactant active, then, with the method for the mixing of oiliness raw material, emulsification is general general knowledge, but be characterized as greatly of the present invention one, in advance the hydrophily polyol fatty acid ester is not added in the aqueous matrix, but is added in the compound that obtains in the 1st step as the fat raw material.What carry out this operation is in the 2nd step of the present invention.Promptly, the compound that obtains in the 1st step of the present invention is because the emulsion stability during by above-mentioned existing emulsification order operation is insufficient, therefore by emulsification order of the present invention, this compound can be wrapped in effectively in the matrix that the alkyl chain by the hydrophily polyol fatty acid ester constitutes, stably carry out emulsification and can dissolve.But, do not get rid of the hydrophily polyol fatty acid ester be added on operation in the aqueous matrix in advance respectively.
Aqueous matrix when being emulsified into oil-in-water type is not particularly limited in water, alcohol, glycerine, propane diols, liquid sugar etc., can use separately, or uses mixture more than 2 kinds.Special preferably glycerine also can wait and improve emulsion stability, liquid fluidity by interpolation water, ethanol.In addition, the use level of aqueous matrix is with respect to mixture 1 weight portion that obtains in the 2nd step, is preferably 0.8～20 weight portion, more preferably 1～10 weight portion, 1.2～2 weight portions more preferably.The method that emulsification method preferably is heated to 50～80 ℃ respectively with the mixture that obtains in the 2nd step and aqueous matrix, carry out emulsification after mixing, but be not particularly limited.As utilizable mulser in the emulsification, can enumerate mulser, homogenizer, super-pressure homogenizer etc.
Can obtain emulsified or solvable the 2nd kind of composition of the present invention that turns to oil-in-water type of CoQ10 thus.Consider that from the good physical and chemical stability aspect of emulsified particle the average emulsification particle diameter of emulsified particle is preferably following, the 1nm～100nm more preferably of 300nm in the said composition.
The 2nd kind of composition of the present invention for example, in emulsifying step of the present invention, cooperates the normally used stabilizing agent of food, preservative agent, pH conditioning agent etc. except preparation as described above, can make emulsion stability more good.In addition, identical with above-mentioned the 1st kind of composition of the present invention, can make Powdered the 2nd kind of composition of the present invention or graininess.For example, make when Powdered, as long as cooperate above-mentioned water miscible excipient to make dried powder.Drying means can be enumerated spray-drying, freeze drying, dull and stereotyped drying etc., is not particularly limited, and preferably utilizes spray-drying.When making graininess, the powdered composition that obtains further is shaped to particle with comminutors such as showering curtain type coating machines gets final product.The storage stability of making dried powder or the 2nd kind of composition of granular the present invention is extremely good, also can keep original well emulsify state in the aqueous medium even add to again.
Composition of the present invention is oral uptake directly, its organism replenishers as CoQ10 can be used thus.In addition, can preferably use as CoQ10 replenishers such as CoQ10 condensed foods.Therefore, as a kind of scheme of the present invention, provide a kind of Foods or drinks that contains the present composition.In addition, also may contain beverage in the food.
Foods or drinks of the present invention is not got rid of the feed of domestic animal or house pet etc. especially with artificial object.Below, the Foods or drinks with artificial object is described, but Foods or drinks of the present invention also comprises above-mentioned feed.
Foods or drinks of the present invention is not particularly limited, and gets final product so long as contain the Foods or drinks of composition of the present invention.As above-mentioned Foods or drinks, for example, can enumerate dairy products such as milk, milk beverage, cheese, preparation milk powder; Cold drink classes such as fruit juice, lactic acid drink, sour milk beverage; Hobby such as coffee, black tea, green tea beverage class; Candy classes such as candy, chewing gum, chocolate, Qu Qi, biscuit, Japanese candy, rice flour system biscuit, cake group; Wheat flour goods classes such as bread, Noodles, cake mix; Sweets classes such as ice cream, ice lolly, pudding, jelly, yogurt, jam; Flavoring classes such as soy sauce, sauce, miso, sweet taste material, spices, flavouring; Soup juice classes such as Miso Soup, face juice, soup; Fish ham sausage, aquatic products boil aquatic products processing categories such as product, canned aquatic products; Pickle livestock products processing category, other various Foods or drinkses such as agricultural production processing categories such as thing, agricultural product fruit can, poultry meat ham and sausage, poultry canned meat.
The content of above-mentioned composition of the present invention is not particularly limited in the Foods or drinks of the present invention.As long as contain the composition that CoQ10 strengthens required sufficient amount, can suitably determine according to the combination of the Foods or drinks that is applicable to the present composition, the picked-up individual subject of this Foods or drinks.As the content of said composition, for example, in Foods or drinks, convert with CoQ10, be preferably 0.0001～50 weight %, more preferably 0.001～20 weight %, 0.002～10 weight % more preferably.
Foods or drinks of the present invention for example can be prepared as follows, in existing Foods or drinks, add composition of the present invention, in addition, when the above-mentioned Foods or drinks of preparation, be prepared by together cooperating in the raw material that composition of the present invention is added in advance to use or in preparation process.In addition, also composition of the present invention (according to circumstances also can be beverage) when the synthetic food together can be added with material and prepare food of the present invention.As long as can access the Foods or drinks that to bring into play the desired effect of the present invention, be not particularly limited for the interpolation time or the adding method of composition of the present invention in Foods or drinks.
Foods or drinks of the present invention contains the CoQ10 that is higher than existing Foods or drinks, but because CoQ10 is stabilized ground emulsification maybe can dissolve, and does not therefore produce CoQ10 and separates out the white casse that causes etc.Particularly major part such as cold drink water is a transparency liquid, cooperates the outward appearance of this beverage that composition of the present invention obtains to have no less than the transparency of existing beverage.Thus,, the outward appearance of Foods or drinks is worsened, again the CoQ10 that carries out in the Foods or drinks be strengthened by composition of the present invention.
In addition, as described in following embodiment, composition of the present invention can demonstrate the good treatment of various diseases etc., preventive effect etc., therefore, and the therapeutic agent or the prophylactic of the above-mentioned various diseases that CoQ10 can be played a role as active ingredient etc.Therefore, according to the present invention, can provide a kind of therapeutic agent or prophylactic that contains composition of the present invention, be used to make the application of the present composition of above-mentioned therapeutic agent or prophylactic.This therapeutic agent or prophylactic are preferably and are suitable for peroral administration preparation.Said preparation can use assistants such as pharmaceutically useful for example excipient, wetting agent, adhesive, stabilizing agent, diluent to make powder, granule, tablet, pill, capsule, liquor or syrup according to the known method in pharmaceuticals field, the particularly existing manufacture method that contains therapeutic agent or the prophylactic of CoQ10.The content of the present composition is not particularly limited in this therapeutic agent or the prophylactic, converts with CoQ10, is preferably 0.0001～50 weight %, and more preferably 0.001～20 weight % most preferably is 0.002～10 weight %.In addition, the dosage of this therapeutic agent or prophylactic can suitably determine based on the effective dose (can confirm the amount of action effect that CoQ10 produce) of CoQ10 in treatment or prevention as active ingredient according to settings such as the target disease for the treatment of or prevent, patient's age, body weight.This dosage is not particularly limited, for example, and about preferred administration every day of people 0.15～20mg/kg body weight.The therapeutic agent that the present invention obtains or the pharmacological effect of prophylactic can use the animal patterns such as rat that for example suffer from target disease to estimate.
Embodiment
Below, by embodiment the present invention is described, but the present invention is not limited to this embodiment.
Embodiment 1-1
With polyglyceryl fatty acid ester (polyglycereol average degree of polymerization 6, HLB=14; Trade name " Sunsoft No.Q12F " Taiyo Kagaku Co., Ltd.'s system) 2.0g adds among 70 ℃ the water 50.0g, stirs with PHYSCOTRON ((strain) day sound medical knowledge section apparatus fabricate is made).Then, keep 70 ℃, and stir with PHYSCOTRON on the limit, Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 5g, polyglycereol condensation ricinoleate (polyglycereol average degree of polymerization 5, ricinoleic acid condensation degree=2, HLB=14, Taiyo Kagaku Co., Ltd.'s system) 43g are added in the limit, stir with PHYSCOTRON, obtain yellow oil-in-water and drip the composition that oil-in-water type contains Co-Q10.
Embodiment 1-2
With glycerine fatty acid organic acid esters (organic acid: citric acid, HLB=8.5; Trade name " Sunsoft No.623M ", Taiyo Kagaku Co., Ltd.'s system) 1.2g, polyglyceryl fatty acid ester (polyglycereol average degree of polymerization 6, HLB=10.5; Trade name " Sunsoft No.Q18F ", Taiyo Kagaku Co., Ltd.'s system) 1.5g adds among 60 ℃ the water 49.3g, stirs with PHYSCOTRON.Then, keep 70 ℃ and limit to stir the limit and add Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 5g, polyglycereol condensation ricinoleate (polyglycereol average degree of polymerization 5, ricinoleic acid condensation degree=2, HLB=16, Taiyo Kagaku Co., Ltd.'s system) 43g with PHYSCOTRON, stir with PHYSCOTRON, obtain yellow oil-in-water and drip the composition that oil-in-water type contains Co-Q10.The average emulsification particle diameter of the emulsified particle of Co-Q10 is 20.3nm in the said composition.
Embodiment 1-3
With glycerine fatty acid organic acid esters (organic acid: citric acid, HLB=9.5; Trade name " SunsoftNo.621B ", Taiyo Kagaku Co., Ltd.'s system) 10.0g, polyglyceryl fatty acid ester (polyglycereol average degree of polymerization 10, HLB=11; Trade name " Sunsoft No.Q182S ", Taiyo Kagaku Co., Ltd.'s system) 14.0g adds among 60 ℃ the water 883.0g, stirs with mulser (TOKUSHU KIKAI KOUGYO CO., LTD. system).Then, keep 80 ℃ and limit to stir the limit and add Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 50g, polyglycereol condensation ricinoleate (polyglycereol average degree of polymerization 5, ricinoleic acid condensation degree=2, HLB=18, Taiyo Kagaku Co., Ltd.'s system) 43.0g with mulser, stir the back with mulser and add glycerine 1000g, stir with mulser again.Then, make it pass through homogenizer (three and mechanical Co., Ltd. system), obtain yellow oil-in-water and drip the composition that oil-in-water type contains Co-Q10.The average emulsification particle diameter of the emulsified particle of Co-Q10 is 40.4nm in the said composition.
Embodiment 1-4
With polyglyceryl fatty acid ester (polyglycereol average degree of polymerization 6, HLB=14; Trade name " Sunsoft No.Q12F ", Taiyo Kagaku Co., Ltd.'s system) 1.5g adds among the water 50.5g that is heated to 65 ℃, stirs with PHYSCOTRON.Then, keep 70 ℃ and limit to stir the limit and add Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 5g and water 43g, stir, obtain yellow oil-in-water and drip the composition that oil-in-water type contains Co-Q10 with PHYSCOTRON with PHYSCOTRON.The average emulsification particle diameter of the emulsified particle of Co-Q10 is 241nm in the said composition.
Embodiment 1-5
With polyglyceryl fatty acid ester (HLB=11; Trade name " Sunsoft No.Q182S ", Taiyo Kagaku Co., Ltd.'s system) 0.7g, glycerine fatty acid organic acid esters (organic acid: diacetyl tartaric acid, HLB=9; Trade name " SunsoftNo.641D ", Taiyo Kagaku Co., Ltd.'s system) 0.5g adds among 80 ℃ the water 50.0g, stirs with PHYSCOTRON.Then, keep 80 ℃ and limit to stir the limit and add Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 2.5g, stir, obtain yellow oil-in-water and drip the composition that oil-in-water type contains Co-Q10 with PHYSCOTRON with PHYSCOTRON.The average emulsification particle diameter of the emulsified particle of Co-Q10 is 175nm in the said composition.
Embodiment 1-6
400g water is heated to 60～70 ℃ in advance, and the limit is stirred the limit with PHYSCOTRON and is added casein (trade name " ACID CASEIN EDIBLE 30/60 MESH ", MEGGLE society system) 18.9g, sodium carbonate (trade name " soda ash light ", TOSOH Co., Ltd's system) 1.3g, organic acid mono-glyceride (organic acid: citric acid, HLB=9.5; Trade name " SunsoftNo.621B ", Taiyo Kagaku Co., Ltd.'s system) 8.2g, polyglyceryl fatty acid ester (HLB=10.5; Trade name " SunsoftNo.Q18F ", Taiyo Kagaku Co., Ltd.'s system) behind the 11.3g, stirred 30 minutes to 1 hour with mulser.Then, add Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 40.og, dextrin (trade name " Sundec#70 ", three and starch industry Co., Ltd. system) 20.3g, with mulser stir about 30 minutes.Then, the spray-dried dried powder of making obtains oil-in-water and drips the composition powder that oil-in-water type contains Co-Q10.
Embodiment 1-7
Alginic acid Na (trade name " KIMITSU ALGIN I-3F ", monarch Tianjin chemical industry Co., Ltd. system) 16.2g is added among the water 400g that is heated to 75 ℃, add lecithin (HLB
=7; Trade name " SUNLECITHIN L6 ", Taiyo Kagaku Co., Ltd.'s system) 10.0g, lysolecithin (HLB=12; Trade name " SUNLECITHIN A ", Taiyo Kagaku Co., Ltd.'s system) 9.5g, stir with mulser.Then, keep 70 ℃, and the limit is stirred the limit with mulser and is added Co-Q10 (Kanegafuchi Chemical Industry Co., Ltd's system) 20.0g, and dextrin (trade name " BLD No.8 ", the loose Industrial Co., Ltd of ginseng system) 44.3g is added on the limit when stirring with mulser, make its dissolving, then, the spray-dried dried powder of making obtains oil-in-water and drips the powder that oil-in-water type contains the Co-Q10 composition.
Embodiment 1-8
Behind mixing water 88.78g, fructose Glucose Liquid sugar 10.8g, citric acid 0.18g, the trisodium citrate 0.04g, be heated to 93～95 ℃ while stirring, add, the composition 0.2g that contains Co-Q10 of mix embodiment 1-3, obtain containing the beverage of Co-Q10.
Embodiment 1-9
The composition 1g that contains Co-Q10 that mixes wheat flour 100g, margarine 60g, granulated sugar 40g, fine salt 1g, baking powder 1.6g, whole egg 30g, water 10g, embodiment 1-6, the bent neat blank of preparation according to a conventional method.After the demoulding,, obtain containing the Qu Qi of Co-Q10 160 ℃ of following roastings 11～12 minutes.
Embodiment 1-10
With the composition that contains Co-Q10 of 100g embodiment 1-6 showering curtain type coating machine (FREUND Industry Co., Ltd system) limit spraying 1 (w/v) % dextrin (trade name " BLDNo.8 ", the loose Industrial Co., Ltd of ginseng system) aqueous solution 20g, granulation is carried out on the limit, obtains containing the additive of graininess Co-Q10.
Embodiment 1-11
With commercially available milk 99g refrigeration (4 ℃), the composition 1g that contains Co-Q10 of mix embodiment 1-3 obtains the milk that every 100g contains the 25mg Co-Q10 simultaneously.
Embodiment 1-12
With the composition 1g that contain Co-Q10 of commercially available tea beverage 99g, obtain the transparent tea beverage that every 100g contains the 50mg Co-Q10 at 60 ℃ of following stirrings, limit mix embodiment 1-3.
Embodiment 1-13
Commercially available mineral water 99g is stirred under 60 ℃, mix the composition 1g that contains Co-Q10 of the embodiment 1-2 that is heated to 60 ℃ in advance simultaneously, stir cooling immediately in 10 minutes, obtain the transparent mineral water that every 100g contains the 50mg Co-Q10.
Embodiment 1-14
Commercially available coffee beverage 99g is at room temperature stirred, and the composition 1g that contains Co-Q10 of mix embodiment 1-3 obtains the coffee beverage that every 100g contains the 25mg Co-Q10 simultaneously.
Embodiment 1-15
Commercially available black tea drinks 99g is stirred down at 80 ℃, mix the composition 1g that contains Co-Q10 of the embodiment 1-2 that is heated to 65 ℃ in advance simultaneously, stir cooling immediately after 10 minutes, obtain the black tea drinks that every 100g contains the 50mg Co-Q10.
Embodiment 1-16
Commercially available clear soup powder is dissolved in for 1 part among the water 150mL that is heated to 95 ℃, and the composition 2g that contains Co-Q10 of mix embodiment 1-3 obtains the transparent clear soup that every 150mL contains the 50mg Co-Q10.
Embodiment 1-17
Commercially available juice 99g stirred down at 80 ℃, mix the composition 1g that contains Co-Q10 of the embodiment 1-2 that is heated to 55 ℃ in advance simultaneously, stir cooling immediately after 10 minutes, obtain the transparent area juice that every 100g contains the 50mg Co-Q10.
Test the emulsion stability that routine 1-1 contains the composition of Co-Q10 and contains the beverage of said composition
The composition 0.2g that contains Co-Q10 of record in embodiment 1-2 or 3 is added on back stirring among the water 100mL, and preparation contains the water of Co-Q10.Use the beverage that contains Co-Q10 of this water that contains Co-Q10, embodiment 1-8 and commercially available co-enzyme Q 10 formulations 0.2g as a comparative example, the beverage that will similarly prepare with embodiment 1-8 is as test specimen, after confirming that preparation has just finished, emulsified state and average emulsification particle diameter under refrigeration (4 ℃) and 40 ℃ of lucifuge conditions after 2 weeks, 4 weeks, 6 weeks.The mensuration of average emulsification particle diameter uses laser refraction type particle size distribution device (NICOMP MODEL370, Particle Sizing Systems society system) to measure.The result is shown in table 1 and table 2.
The result that [table 1] refrigeration (4 ℃) is kept in Dark Place
[table 2] 40 ℃ of results that keep in Dark Place
In addition, with the powder-product of embodiment 1-6 and 7 and Co-Q10 itself (Kanegafuchi Chemical Industry Co., Ltd's system) as test specimen, confirm to begin to preserve preceding, and at the preservation state after 4 weeks, 12 weeks under 50 ℃ of lucifuges.The result is as shown in table 3.
[table 3] 50 ℃ of results that keep in Dark Place
| Test specimen | Project | Before beginning to preserve | After 4 weeks | After 12 weeks |
| The powder of embodiment 1-6 | Preservation state | Yellow powder | Yellow powder | Yellow powder |
| The powder of embodiment 1-7 | Preservation state | Yellow powder | Yellow powder | Yellow powder |
| The Co-Q10 powder | Preservation state | Yellow powder | Melt | Melt |
By the result of table 1 and 2 as can be known, as the water that contains Co-Q10 (embodiment 1-2 and 3) of product of the present invention, contain the beverage (embodiment 1-8) of Co-Q10 even significant change does not take place yet for emulsified state etc. after 6 weeks, but be in the emulsification or the melting state of stabilizer pole.In addition, as shown in Table 3 as containing of product of the present invention auxilliary pure Q10 the powder (embodiment 1-6 and 7) of composition compare with Co-Q10 itself and demonstrate high storage stability.
In addition, 40 ℃ of Co-Q10 assay result demonstrations of the water that contains Co-Q10 of the embodiment 1-3 of preservation down, the residual rate of Co-Q10 is higher during through 6 weeks, is 85.2 weight %.In addition, 50 ℃ of Co-Q10 assay result demonstrations of the composition powder that contains Co-Q10 of the embodiment 1-6 of preservation down, the Co-Q10 residual rate during through 12 weeks is higher, is 96.5 weight %.
Test the stability of food that routine 1-2 contains the composition of Co-Q10
For the food of the composition that contains Co-Q10 of embodiment 1-8～17, the state after 8 hours after with the naked eye estimating preparation and just having finished and under the room temperature (25 ℃).In addition, Co-Q10 itself melted use, and make its Co-Q10 content identical, with the composition that contains Co-Q10 that replaces using among each embodiment as product of the present invention, the sample of the method preparation that each embodiment of employing is identical is similarly estimated as the reference substance that corresponds respectively to embodiment 1-8～17.
The result is, for the various aqueous food such as beverage of embodiment 1-8 and 11～17, corresponding whole reference substances Co-Q10 occurs after preparation just finishes, in the crystallization of separating out Co-Q10 through 8 hours time point, with respect to this, arbitrary sample is after preparation has just been finished and through 8 hours the time point not change of Discovery Status fully.In addition, there are any problem in embodiment 1-9 also unconfirmed and 10 solid food.Hence one can see that, identical with the proterties of original food as the food of the composition that contains Co-Q10 of product of the present invention, is that the food that any proterties changes, is rich in Co-Q10 does not take place.
Especially, comprise transparent beverage in the beverage that obtains among the embodiment, still contain the composition of Co-Q10, do not damage its original transparency by interpolation.This is considered to because in the composition that contains Co-Q10 that adds, Co-Q10 maybe can be dissolved by the emulsification of highly stable ground usually.Hence one can see that, owing to can add in the aqueous medium as the composition that contains Co-Q10 of product of the present invention, therefore do not have hell and high water when preparation contains the food of said composition, and said composition has general usability to food.
Test the bioabsorbable test 1 of routine 1-3 Co-Q10
To give rat respectively as powder and the Co-Q10 itself of the embodiment 1-6 of test specimen, the Co-Q10 concentration in the blood plasma is measured in the time dependent blood sampling, estimates the bioabsorbable of Co-Q10 thus, relatively each test specimen.
(test specimen and feeding condition)
Test specimen connects the administering mode shown in the following table 4 to the rat administration.Make rat freely absorb feed.In addition, CMC-Na represents the sodium salt of carboxy methyl cellulose.
[table 4]
| Test specimen | Administering mode | |
| Sample | The powder-product of embodiment 1-6 | The solution of distilled water |
| Comparative sample 1 | The Co-Q10 powder | The solution of soybean oil |
| Comparative sample 2 | The Co-Q10 powder | 0.5 (w/v) suspension of the %CMC-Na aqueous solution |
Sample 1 is added in the distilled water, mixes and prepare by the powder with embodiment 1-6.Comparative sample 1 is by preparing mixing after the heating for dissolving of Co-Q10 own, with soybean oil.Comparative sample 2 is by adding Co-Q10 itself in 0.5 (w/v) %CMC-Na aqueous solution, being prepared with ultrasonic wave.
The condition of following notebook test etc.
Rat: Crj-SD system, male 6 ages in week, n=4
Dosage: the test specimen that gives to be scaled 30mg by every 1kg rat body weight by Co-Q10.
Give amount of liquid medicine: every 1kg rat body weight gives 10mL in sample 1 and the comparative sample 3, and every 1kg rat body weight gives 3mL in the comparative sample 2.
Medication: use irrigation stomach device oral administration by force.
Blood sampling:, use the about 0.5mL of blood collection needle that has added heparin through jugular vein.
Blood sampling time: after beginning 1,2,4,8 and 24 hour from administration.
Blood processing: just after the blood sampling blood is being preserved under freezing condition, under 4 ℃, carried out centrifugation, separated plasma at once after blood sampling is finished.After dividing the blood plasma after separating in the injection preservation container, preserve until use down at-80 ℃.
Quantitative approach:, after blood is extracted out, the concentration of the Co-Q10 in the blood plasma is carried out quantitatively with high performance liquid chromatography (HPLC) by following conventional method.That is, with respect to blood plasma 0.2mL, add, mix 1 (w/v) %FeCl
3Aqueous solution 0.01mL, deionized water 0.5mL and methyl alcohol 2mL.In the mixed liquor that obtains, add, mix hexane 3mL, extract Co-Q10.Separate hexane, its evaporation is solidified after, be dissolved in ethanol 0.2mL again, carry out quantitatively.
(condition of HPLC)
Detector: ultraviolet light absorption photometer
Detect wavelength: 275nm
Post: YMC-Pack ODS-A303
(YMC society system)
Phase: methyl alcohol: hexane=88:12 (Capacity Ratio) flows
Flow velocity: 1mL/ minute
Analysis time: 40 minutes
Give behind the rat Co-Q10 concentration determination result such as the table 5 and shown in Figure 1 in the blood plasma in 1～24 hour with sample 1, comparative sample 1 or comparative sample 2.
[table 5]
| Test specimen | Administering mode | |
| Sample 1 | The powder-product of embodiment 1-6 | The solution of distilled water |
| Comparative sample 1 | The Co-Q10 powder | The solution of soybean oil |
| Comparative sample 2 | The Co-Q10 powder | 0.5 (w/v) suspension of the %CMC-Na aqueous solution |
When giving sample 1, the Co-Q10 concentration in the blood plasma is from keeping high value in 4 hours to 8 hours after the administration, at 8 hours peakings (Tmax).In addition, when giving comparative sample, Tmax is after the administration 2 hours.When giving sample 1, present lasting Co-Q10 blood level pattern.
In addition, the maximum concentration in the blood plasma (Cmax) is 2.1 times of comparative sample 1 when giving sample 1,1.6 times of comparative sample 2; Concentration integrated value (AUC in the blood plasma in 1～24 hour
1 -24) when giving sample 1, be 2.5 times of comparative sample 1, be 1.8 times of comparative sample 2.
As can be known every 1kg rat body weight is given when giving Co-Q10 and being scaled the test specimen of 30mg according to The above results, sample 1 demonstrates the high bioabsorbable of the Co-Q10 that is higher than comparative sample 1 and 2.
Test the bioabsorbable test 2 of routine 1-4 Co-Q10
Will as the composition that contains Co-Q10 of the embodiment 1-2 of test specimen, and Co-Q10 itself give rat respectively, through the time blood sampling, measure the Co-Q10 concentration in the blood plasma, estimate the bioabsorbable of Co-Q10 thus, relatively each test specimen.
(test specimen and feeding condition)
Administering mode shown in the test specimen according to the form below 6 carries out administration to rat.In addition, the feeding condition is freely absorbed feed (being satiated with food) for making rat; And stop feeding at the night of test day before yesterday, giving test specimen after 2 kinds of situations of feeding once more after 8 hours the blood sampling.
[table 6]
Distilled water solution among test A and the A ' is to be added in the distilled water, to mix and prepare by the composition that contains Co-Q10 with embodiment 1-2.The suspension of 0.5 (w/v) %CMC-Na aqueous solution among test B and the B ' is by Co-Q10 itself being added in 0.5 (w/v) %CMC-Na aqueous solution, being prepared with ultrasonic wave.
Provide the condition of this test etc. below.
Rat: SD system, 7 ages in week, male, n=4.
Dosage: every 1kg rat body weight gives to be scaled by Co-Q10 the test specimen of 5mg.
Administration amount of liquid: being every 1kg rat body weight to amount of liquid medicine and being 5mL of suspension that uses among test A, A ', B, the B ' or solution.
In addition, medication, blood sampling, blood sampling time, blood processing and quantitative approach are identical with above-mentioned test example 1-3.
It is as shown in table 7 that each test specimen that will test A and B and test A ' and B ' gives behind the rat in 1～24 hour the measurement result of the auxilliary pure Q10 concentration in the blood plasma.In addition, the measurement result of test A and A ' and comparative test B and B ' is shown in the curve map of Fig. 2.
[table 7]
By the result of table 7 and Fig. 2 as can be known, as product of the present invention, infer that the composition that contains Co-Q10 (embodiment 1-2) that has formed the emulsification tunicle compares with independent use Co-Q10, its infiltration rate is exceedingly fast.Hence one can see that, by improving absorbability, can expect further to improve the effect of having reported the disease of Co-Q10 curative effect for following, as: heart disease is (for example, the ischemic cardiac dysfunction, coronary heart disease, miocardial infarction etc.), hypertension, diabetes, cancer, gum disease, sacred disease (for example, Parkinson's, Alzheimer disease, chorea), progressive muscular dystrophy, allergy (for example, hereditary allergic dermatitis), infertility, AIDS, chronic lung disease (for example, the chronic occlusion lung disease, sudden pulmonary fibrosis etc.) disease such as, can expect setting up or improving the wrinkle effect, postoperative (for example, the operation of recuperating, PTCA etc.) better effect such as.
Embodiment 2-1
(ubidecarenone preparation)
＜the 1 step 〉
15g is heated to 50 ℃ with SUNFAT U-12 (trade name " SUNFAT U-12 ", HLB=1.5, Taiyo Kagaku Co., Ltd.'s system), ubidecarenone (Kanegafuchi Chemical Industry Co., Ltd's system) 5g that the slow adding in limit is heated to 55 ℃ is in advance stirred with PHYSCOTRON in the limit, obtains the ubidecarenone compound of yellow transparent.
＜the 2 step and the emulsifying step 〉
The limit is heated to 50 ℃ with ubidecarenone compound 20g, the polyglycereol condensation ricinoleate be heated to 50 ℃ in advance (the polyglycereol average degree of polymerization is 5, ricinoleic acid condensation degree=2, HLB=14, Taiyo Kagaku Co., Ltd.'s system) 54g and polyglycereol condensation ricinoleate (the polyglycereol average degree of polymerization is 5, ricinoleic acid condensation degree=2, HLB=16, Taiyo Kagaku Co., Ltd.'s system) 6g is added on the limit, stirs with PHYSCOTRON.Then, the mixture that obtains is remained on 50 ℃, and the limit stirs the limit with PHYSCOTRON and add glycerine 100g, water 15g, ethanol 5g successively, the oil-in-water that obtains yellow transparent drips oil-in-water type ubidecarenone preparation.The average emulsification particle diameter of the emulsified particle of ubidecarenone is 52.0nm in the said preparation.
Embodiment 2-2
＜ubidecarenone preparation 〉
＜the 1 step 〉
19g is heated to 65 ℃ that it is melted with single glyceryl monolaurate (trade name " SUNSOFT No.750 ", HLB=5.3, Taiyo Kagaku Co., Ltd.'s system), the limit is stirred the limit with PHYSCOTRON and is slowly added ubidecarenone (Kanegafuchi Chemical Industry Co., Ltd's system) 1g, obtains the ubidecarenone compound of yellow transparent.
＜the 2 step and the emulsifying step 〉
35g is heated to 80 ℃ in advance that it is melted with SUNSOFT 641C (trade name " SUNSOFT641C ", HLB=10, Taiyo Kagaku Co., Ltd.'s system) 25g, ten glycerol distearates (trade name " SUNSOFT Q-182S ", HLB=11, Taiyo Kagaku Co., Ltd.'s system), and the limit is stirred the limit with PHYSCOTRON and added ubidecarenone compound 20g.Then, the mixture that obtains is remained on 65 ℃, and the limit stirs the limit with PHYSCOTRON and add glycerine 100g, water 20g, the oil-in-water that obtains yellow transparent drips oil-in-water type ubidecarenone preparation.The average emulsification particle diameter of the emulsified particle of ubidecarenone is 80.7nm in the said preparation.
Embodiment 2-3
＜ubidecarenone preparation 〉
＜the 1 step 〉
17g is heated to 45 ℃ with SUNSOFT A-173E (trade name " SUNSOFT A-173E ", HLB=7, Taiyo Kagaku Co., Ltd.'s system), slow while stirring interpolation is heated to 65 ℃ ubidecarenone (Kanegafuchi Chemical Industry Co., Ltd's system) 3g in advance, obtains the ubidecarenone compound of yellow transparent.
＜the 2 step and the emulsifying step 〉
Add SUNSOFT A-141E (trade name " SUNSOFT A-141E ", HLB=13, Taiyo Kagaku Co., Ltd.'s system) 60g in ubidecarenone compound 20g, the limit remains on 45 ℃ of limits and stirs with mulser.Then, stir, simultaneously the mixture that obtains is added to respectively among the glycerine 100g that is heated to 50 ℃, obtain emulsion with mulser.To work as this emulsion and further homogenize with PHYSCOTRON, and add ethanol 6g then, the oil-in-water that obtains yellow transparent drips oil-in-water type ubidecarenone preparation.The average emulsification particle diameter of the emulsified particle of ubidecarenone is 125nm in the said preparation.
Embodiment 2-4
＜ubidecarenone preparation 〉
Water 200g is heated to 65～70 ℃, limit in advance to be stirred with PHYSCOTRON, the limit is added dextrin (BLD No.8, the loose Industrial Co., Ltd of ginseng system) 50g, is made its dissolving, keep 65～70 ℃, slowly drop into the ubidecarenone preparation 10g of embodiment 2-3 simultaneously, make its emulsification, make dried powder with spray-drying then, obtain oil-in-water and drip oil-in-water type ubidecarenone preparation powder.
Embodiment 2-5
＜contain the food of ubidecarenone preparation 〉
Behind mixing water 88.78g, fructose Glucose Liquid sugar 10.8g, citric acid 0.18g, the trisodium citrate 0.04g, be heated to 93～95 ℃ while stirring, add the ubidecarenone preparation 0.2g of the embodiment 2-1 that is heated to 60 ℃ in advance, mix the transparent beverage that obtains containing ubidecarenone.
Embodiment 2-6
＜contain the food of ubidecarenone preparation 〉
The ubidecarenone preparation 1g that mixes wheat flour 100g, margarine 60g, granulated sugar 40g, fine salt 1g, baking powder 1.6g, whole egg 30g, water 10g, embodiment 2-4, the bent neat blank of preparation.After the demoulding,, obtain containing the Qu Qi of Co-Q10 180 ℃ of following roastings 11～12 minutes.
Embodiment 2-7
＜contain the food of ubidecarenone preparation 〉
With showering curtain type coating machine (FREUND Industry Co., Ltd system) the limit 1% dextrin 20g (BLD No.8, the loose Industrial Co., Ltd of ginseng system) that sprays, granulation is carried out on the limit, obtains containing the additive of graininess ubidecarenone with the ubidecarenone preparation 100g of embodiment 2-4.
Embodiment 2-8
＜contain the food of ubidecarenone preparation 〉
Stir commercially available milk 99g down at 60 ℃, mix the ubidecarenone preparation 1g of the embodiment 2-1 that is heated to 60 ℃ in advance simultaneously, stir cooling immediately after 10 minutes, obtain containing the milk of 25mg ubidecarenone/100g.
Embodiment 2-9
＜contain the food of ubidecarenone preparation 〉
Cooling immediately after 10 minutes is stirred with the ubidecarenone preparation 1g that commercially available tea beverage 99g stirs down at 60 ℃, mixing is heated to 60 ℃ embodiment 2-1 in advance simultaneously in the limit, obtains containing the transparent tea beverage of 25mg ubidecarenone/100g.
Embodiment 2-10
＜contain the food of ubidecarenone preparation 〉
With the ubidecarenone preparation 1g that stir down at 60 ℃ on commercially available mineral water 99g limit, mixing is heated to 60 ℃ embodiment 2-1 in advance simultaneously, stir cooling immediately after 10 minutes, obtain containing the transparent mineral water of 25mg ubidecarenone/100g.
Embodiment 2-11
＜contain the food of ubidecarenone preparation 〉
With the ubidecarenone preparation 1g that commercially available coffee beverage 99g stirs down at 70 ℃, mixing is heated to 65 ℃ embodiment 2-2 in advance simultaneously, stir cooling immediately after 10 minutes, obtain containing the coffee beverage of 5mg ubidecarenone/100g.
Embodiment 2-12
＜contain the food of ubidecarenone preparation 〉
Commercially available black tea drinks 99g is stirred down at 80 ℃, mix the ubidecarenone preparation 1g of the embodiment 2-2 that is heated to 65 ℃ in advance simultaneously, stir cooling immediately after 10 minutes, obtain containing the black tea drinks of 5mg ubidecarenone/100g.
Embodiment 2-13
＜contain the food of ubidecarenone preparation 〉
Commercially available clear soup powder is dissolved in for 1 part among the water 150ml that is heated to 95 ℃, and the ubidecarenone preparation 1g of mix embodiment 2-2 obtains containing the transparent clear soup of 5mg ubidecarenone/150ml.
Embodiment 2-14
＜contain the food of ubidecarenone preparation 〉
Commercially available juice 99g 80 ℃ of following stirrings, mixed the ubidecarenone preparation 1g of the embodiment 2-3 that is heated to 55 ℃ in advance simultaneously, stir cooling immediately after 10 minutes, obtain containing the transparent area juice of 15mg ubidecarenone/100g.
Test routine 2-1
＜contain the storage stability of the beverage of ubidecarenone preparation and said preparation 〉
Stir after the ubidecarenone preparation 0.2g that is heated to 50 ℃ embodiment 2-1～3 record being added among 50 ℃ the water 100ml, preparation contains the water of ubidecarenone.For this beverage that contains ubidecarenone and 5 weight % ubidecarenone preparation 0.1g that other companies of use as a comparative example make and beverage that embodiment 2-5 similarly prepares that contains water, the embodiment 2-5 of ubidecarenone, confirm prepare just finished after, emulsified state and average emulsification particle diameter after following 1 day of room temperature and 50 ℃, 2 weeks, 4 weeks.The mensuration of average emulsification particle diameter uses above-mentioned laser refraction type particle size distribution device (NICOMP MODEL370) to measure.The result is shown in table 8 and table 9.
The emulsion stability of table 8 ubidecarenone preparation (preserving under the room temperature)
The emulsion stability of table 9 ubidecarenone preparation (preserving down for 50 ℃)
By table 8, table 9 as can be known, but the water that contains ubidecarenone of embodiment 2-1～3 demonstrates extremely stable emulsification or melting state.In addition, 50 ℃ of ubidecarenone assay result demonstrations of the beverage that contains ubidecarenone of the embodiment 2-5 of preservation down, the ubidecarenone residual rate through 4 weeks the time is higher, is 91.4 weight %.
Test routine 2-2
＜contain the storage stability of the food (beverage) of ubidecarenone preparation 〉
For the food that contains the ubidecarenone preparation of record in embodiment 2-8～14, with the naked eye estimate preparation and just finished the proterties after 8 hours under back and the room temperature.In addition, use the identical ubidecarenone of ubidecarenone content to melt the sample of formation separately,, as reference substance, similarly estimate respectively corresponding to embodiment 2-8～14 with the ubidecarenone preparation that replaces using among each embodiment.The result shows, whole beverages of reference substance all ubidecarenone occurs after preparation just finishes, separate out the ubidecarenone crystallization through 8 hours time point, whole beverages of embodiment 2-8～14 have just finished the back and have not also had fully after 8 hours to change in preparation in contrast, and any change does not take place original beverage proterties.
Food and the original food proterties that contains the ubidecarenone preparation of the present invention is identical, and is not taking place to have strengthened ubidecarenone under the situation that any proterties changes.Particularly, even transparent beverage of the present invention does not damage original transparency yet.This is the effect that contains the ubidecarenone preparation of the present invention that comprises in the food of ubidecarenone preparation of the present invention.Promptly, ubidecarenone preparation of the present invention be called the composite interstitial substance that lipophile and hydrophilic opposite polarity polyol fatty acid ester and ubidecarenone form the three, and utilize the hydrophily polyol fatty acid ester to form Nano capsule (the average emulsification particle diameter 10～150nm) of stabilisation.Therefore in addition, ubidecarenone preparation of the present invention can add in the aqueous medium, and when the preparation food that contains the ubidecarenone preparation of the present invention, no hell and high water has general usability to food.
Test routine 2-3
＜contain the effect of the food of ubidecarenone preparation 〉
With 16 of 34 of the healthy normal male sex of 22～51 years old (36.7 years old mean age, average weight 58.6kg) and women as the experimenter, use the food 100ml that contains the ubidecarenone preparation (content of ubidecarenone is 5mg) of embodiment 2-5,3 times on the early, middle and late 1st (ubidecarenone 15mg/ days) took this food in totally 2 weeks, estimated by following metewand.In addition, utilize the food preparation that contains the ubidecarenone preparation of embodiment 2-5 to remove the food (control food) of the ubidecarenone preparation of embodiment 2-1, equally 50 experimenters are carried out same test.
＜metewand 〉
With take before compare body weight and significantly lighten: 2 minutes
With take before compare body weight and lighten: 1 minute
With take before compare no change: 0 minute
With take before compare body weight and become heavy :-1 minute
With take before compare body weight and significantly become heavy :-2 minutes
As a result, when taking control food, all experimenters be equally divided into 0.06, in contrast, when taking the food that contains the ubidecarenone preparation of the present invention, be equally divided into 1.64 fens, and do not have that 1 example is negative to be estimated.This is the effect that contains the ubidecarenone preparation of the present invention that comprises in the food of ubidecarenone preparation of the present invention.Though promptly infer ubidecarenone and lipophile polyol fatty acid ester formation compound in food of the present invention, and this compound is enclosed in the nanometer emulsified particle of hydrophily polyol fatty acid ester formation, but in vivo, in this compound, discharge ubidecarenone.Therefore, ubidecarenone preparation of the present invention can form the system that can stably add in the aqueous medium, is a kind of preparation that does not influence the original effect to human body of ubidecarenone simultaneously, and this is the feature of food of the present invention.In addition, be included in the fine emulsified particle of 10～150nm, therefore think that the living bulk absorption of ubidecarenone also is improved owing to infer the ubidecarenone in the food of the present invention.
Industrial applicability
According to the present invention, can provide a kind of storage stability good and improved CoQ10 bioabsorbable, applicable to the composition that contains CoQ10 of food applications. Said composition can both operability be added in the aqueous medium in various food processings well, particularly owing to can be applied in the transparent beverage, therefore contribute greatly for Health-care Foods Industry from now on, and have very important significance in industrial aspect.
Claims (13)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP009013/2003 | 2003-01-17 | ||
| JP2003009013A JP4567945B2 (en) | 2003-01-17 | 2003-01-17 | Ubidecarenone formulation |
| JP165690/2003 | 2003-06-10 |
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| Publication Number | Publication Date |
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| CN1738548A CN1738548A (en) | 2006-02-22 |
| CN100536691C true CN100536691C (en) | 2009-09-09 |
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| CNB2004800023313A Expired - Fee Related CN100536691C (en) | 2003-01-17 | 2004-01-15 | Compositions containing coenzyme Q10 |
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| Country | Link |
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| JP (1) | JP4567945B2 (en) |
| CN (1) | CN100536691C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4971597B2 (en) * | 2005-03-23 | 2012-07-11 | 東海物産株式会社 | Antioxidant composition |
| JP5258144B2 (en) * | 2004-12-21 | 2013-08-07 | 株式会社分子生理化学研究所 | Method for producing solid coenzyme Q10 oral preparation with improved absorbability |
| JP4970734B2 (en) * | 2005-03-03 | 2012-07-11 | 株式会社コーセー | Clear aqueous composition |
| US20090098097A1 (en) * | 2006-01-25 | 2009-04-16 | Kaneka Corporation | Composition for normalizing blood pressure |
| JP2007302585A (en) * | 2006-05-10 | 2007-11-22 | Fuji Capsule Kk | Food and drink and pharmaceutical containing coenzyme q10 |
| JP4869266B2 (en) * | 2008-03-03 | 2012-02-08 | 長谷川香料株式会社 | Beverage emulsion composition containing coenzyme Q10 and method for producing the same |
| US9919017B2 (en) | 2011-02-01 | 2018-03-20 | Kaneka Corporation | Biologically active substance-containing water-solubilizing preparation and method for producing the same |
| CN103027300A (en) * | 2012-09-28 | 2013-04-10 | 石药集团中奇制药技术（石家庄）有限公司 | VE (Vitamin E) coenzyme Q10 composition for assisting to reduce blood fat and boosting immunity and preparation method thereof |
| CN105963254B (en) * | 2016-06-28 | 2019-03-22 | 北京素维生物科技有限公司 | Coenzyme Q10 pharmaceutical composition and preparation process thereof |
| CN112056560A (en) * | 2020-09-18 | 2020-12-11 | 烟台硕人生物科技有限公司 | Preparation method of coenzyme Q10 and brown algae oligosaccharide oxidation composite particle |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5618914A (en) * | 1979-07-25 | 1981-02-23 | Eisai Co Ltd | Ubidecarenone composition having good absorbability |
| JPS5877810A (en) * | 1981-11-01 | 1983-05-11 | Taiho Yakuhin Kogyo Kk | Oral drug composition containing polyglycerol unsaturated fatty acid ester |
| JPS59148718A (en) * | 1983-02-10 | 1984-08-25 | Fujisawa Pharmaceut Co Ltd | Ubidecarenone composition |
| IT1191608B (en) * | 1985-02-01 | 1988-03-23 | Zambon Spa | PHARMACEUTICAL COMPOSITION AND PHARMACEUTICAL FORMS THAT CONTAIN IT |
| JPH0686374B2 (en) * | 1992-03-05 | 1994-11-02 | エーザイ株式会社 | Aqueous liquid containing fat-soluble substance |
| JPH06219923A (en) * | 1993-01-26 | 1994-08-09 | Nippon Zetotsuku Kk | Transparent liquid composition |
| JPH0787892A (en) * | 1993-09-22 | 1995-04-04 | Taiyo Kagaku Co Ltd | Easily soluble cocoa and its preparation |
| JP3294443B2 (en) * | 1994-09-13 | 2002-06-24 | 太陽化学株式会社 | Solubilizing agent and solubilizing composition |
| JP3273882B2 (en) * | 1995-11-14 | 2002-04-15 | 明治製菓株式会社 | Method for producing chocolate confectionery |
| JPH09279129A (en) * | 1996-04-12 | 1997-10-28 | Taiyo Kagaku Co Ltd | Antifogging agent |
| JPH1094375A (en) * | 1996-09-20 | 1998-04-14 | Nisshin Flour Milling Co Ltd | Water-solubilizing type flour for deep-fried food |
| DE19647352C2 (en) * | 1996-11-15 | 2000-06-29 | Aqua Nova Getraenketechnologie | Non-alcoholic beverage containing Q 10 |
| JP3973001B2 (en) * | 1998-02-13 | 2007-09-05 | 太陽化学株式会社 | cream |
| JP2000157168A (en) * | 1998-04-01 | 2000-06-13 | Nisshin Oil Mills Ltd:The | Oily composition and method for producing the same |
| JP4190070B2 (en) * | 1998-11-16 | 2008-12-03 | 太陽化学株式会社 | Water-soluble vitamin-enriched food |
| JP3880265B2 (en) * | 1998-11-16 | 2007-02-14 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Aqueous solution of fat-soluble substances |
| US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| JP4285859B2 (en) * | 1999-11-12 | 2009-06-24 | ライオン株式会社 | W / O / W type composite emulsion |
| JP3996342B2 (en) * | 2000-11-02 | 2007-10-24 | 花王株式会社 | Oil composition |
| US20040115161A1 (en) * | 2001-03-29 | 2004-06-17 | Keiichi Oyama | Cosmetic emulsion preparation and agent for external use |
-
2003
- 2003-01-17 JP JP2003009013A patent/JP4567945B2/en not_active Expired - Fee Related
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2004
- 2004-01-15 CN CNB2004800023313A patent/CN100536691C/en not_active Expired - Fee Related
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| JP4567945B2 (en) | 2010-10-27 |
| CN1738548A (en) | 2006-02-22 |
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