JP2006045217A - Zinc-containing composition for oral administration - Google Patents
Zinc-containing composition for oral administration Download PDFInfo
- Publication number
- JP2006045217A JP2006045217A JP2005196925A JP2005196925A JP2006045217A JP 2006045217 A JP2006045217 A JP 2006045217A JP 2005196925 A JP2005196925 A JP 2005196925A JP 2005196925 A JP2005196925 A JP 2005196925A JP 2006045217 A JP2006045217 A JP 2006045217A
- Authority
- JP
- Japan
- Prior art keywords
- zinc
- fatty acid
- oral administration
- composition
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 239000011701 zinc Substances 0.000 title abstract description 13
- 229910052725 zinc Inorganic materials 0.000 title abstract description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title abstract description 12
- -1 fatty acid ester Chemical class 0.000 claims abstract description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 24
- 239000000194 fatty acid Substances 0.000 claims abstract description 24
- 229930195729 fatty acid Natural products 0.000 claims abstract description 24
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 18
- 150000003752 zinc compounds Chemical class 0.000 claims abstract description 12
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 claims abstract description 9
- 239000011670 zinc gluconate Substances 0.000 claims abstract description 9
- 235000011478 zinc gluconate Nutrition 0.000 claims abstract description 9
- 229960000306 zinc gluconate Drugs 0.000 claims abstract description 9
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 6
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims abstract description 3
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 claims abstract description 3
- 239000011667 zinc carbonate Substances 0.000 claims abstract description 3
- 235000004416 zinc carbonate Nutrition 0.000 claims abstract description 3
- 229910000010 zinc carbonate Inorganic materials 0.000 claims abstract description 3
- 229940043825 zinc carbonate Drugs 0.000 claims abstract description 3
- 239000011592 zinc chloride Substances 0.000 claims abstract description 3
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 3
- 229960001939 zinc chloride Drugs 0.000 claims abstract description 3
- 239000011746 zinc citrate Substances 0.000 claims abstract description 3
- 235000006076 zinc citrate Nutrition 0.000 claims abstract description 3
- 229940068475 zinc citrate Drugs 0.000 claims abstract description 3
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims abstract description 3
- 229910000165 zinc phosphate Inorganic materials 0.000 claims abstract description 3
- 229940077935 zinc phosphate Drugs 0.000 claims abstract description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims abstract description 3
- 229960001763 zinc sulfate Drugs 0.000 claims abstract description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims abstract description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical group 0.000 claims description 11
- 235000019640 taste Nutrition 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 abstract description 22
- 235000019606 astringent taste Nutrition 0.000 abstract description 12
- 235000011187 glycerol Nutrition 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 6
- 206010013911 Dysgeusia Diseases 0.000 abstract description 3
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002314 glycerols Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000008213 purified water Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 239000002253 acid Substances 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 5
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- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
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- UIERGBJEBXXIGO-UHFFFAOYSA-N thiamine mononitrate Chemical compound [O-][N+]([O-])=O.CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N UIERGBJEBXXIGO-UHFFFAOYSA-N 0.000 description 4
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- 229960002675 xylitol Drugs 0.000 description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 3
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- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229960003589 arginine hydrochloride Drugs 0.000 description 1
- PLKYGPRDCKGEJH-UHFFFAOYSA-N azane;2-hydroxypropane-1,2,3-tricarboxylic acid;iron Chemical compound N.[Fe].OC(=O)CC(O)(C(O)=O)CC(O)=O PLKYGPRDCKGEJH-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 1
- 229960000678 carnitine chloride Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 229960002104 cyanocobalamin Drugs 0.000 description 1
- 235000000639 cyanocobalamin Nutrition 0.000 description 1
- 239000011666 cyanocobalamin Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WPUMTJGUQUYPIV-JIZZDEOASA-L disodium (S)-malate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)CC([O-])=O WPUMTJGUQUYPIV-JIZZDEOASA-L 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
- FODTZLFLDFKIQH-FSVGXZBPSA-N gamma-Oryzanol (TN) Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)O[C@@H]2C([C@@H]3CC[C@H]4[C@]5(C)CC[C@@H]([C@@]5(C)CC[C@@]54C[C@@]53CC2)[C@H](C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-FSVGXZBPSA-N 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000006286 nutrient intake Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019265 sodium DL-malate Nutrition 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
本発明は、亜鉛化合物の不快な味を低減し、服用感を良好にした経口投与組成物に関する。 The present invention relates to an orally administered composition that reduces the unpleasant taste of zinc compounds and improves the feeling of taking.
亜鉛含有経口投与組成物は亜鉛イオンに由来する不快な味のため飲みにくいものであった。この味は、タンニンやミョウバンなどのタンパクと結合する収斂剤を口にしたときの味(収斂味)と共通のものである。これまで、亜鉛化合物を含有する薬剤や食品の不快な味を改善するため、アルキルジメチルベタインなどのベタイン型両性界面活性剤を配合する技術が開示されている(特許文献1)。しかしながら、これらの両性界面活性剤では亜鉛イオンに由来する不快な味を改善する効果は充分でなかった。 The composition containing orally containing zinc is difficult to drink due to an unpleasant taste derived from zinc ions. This taste is the same as the taste when using an astringent that binds to proteins such as tannin and alum. Until now, in order to improve the unpleasant taste of drugs and foods containing zinc compounds, a technique of blending a betaine-type amphoteric surfactant such as alkyldimethylbetaine has been disclosed (Patent Document 1). However, these amphoteric surfactants have not been sufficiently effective in improving the unpleasant taste derived from zinc ions.
本発明の目的は、亜鉛イオンに由来する収斂味を低減し、飲みやすく、しかも不快な後味が残らない亜鉛含有経口投与組成物を提供することである。 An object of the present invention is to provide a zinc-containing oral administration composition that reduces the astringent taste derived from zinc ions, is easy to drink, and does not leave an unpleasant aftertaste.
上記課題を解決するために、本発明者らは、鋭意検討を重ねた結果、亜鉛化合物にポリグリセリン脂肪酸エステルを配合すると、亜鉛イオンによるタンパクの凝集(収斂性)が低減し、収斂味が改善されることを見出し、本発明を完成した。 In order to solve the above-mentioned problems, the present inventors have made extensive studies. As a result, when a polyglycerol fatty acid ester is blended with a zinc compound, protein aggregation (convergence) due to zinc ions is reduced, and astringency is improved. As a result, the present invention has been completed.
すなわち、本発明は、亜鉛化合物およびポリグリセリン脂肪酸エステルを含有することを特徴とする経口投与組成物である。 That is, the present invention is an orally administered composition comprising a zinc compound and a polyglycerol fatty acid ester.
本発明における亜鉛化合物とは、亜鉛を含む塩であり、塩を形成する酸は無毒性であれば有機酸又は無機酸のどちらでもかまわず、有機酸としては例えば、乳酸、グルコン酸、クエン酸、リンゴ酸、酒石酸等の有機酸を、また無機酸としては、例えば、硫酸、炭酸、塩酸、リン酸、硝酸等を挙げることができる。好ましい亜鉛化合物としては、例えば、グルコン酸亜鉛、硫酸亜鉛、クエン酸亜鉛、炭酸亜鉛、塩化亜鉛、リン酸亜鉛などが挙げられる。これらは、単独で配合してもよく、2種以上を組み合わせて配合してもよい。 The zinc compound in the present invention is a salt containing zinc, and the acid forming the salt may be either an organic acid or an inorganic acid as long as it is non-toxic. Examples of the organic acid include lactic acid, gluconic acid, and citric acid. Organic acids such as malic acid and tartaric acid, and inorganic acids include sulfuric acid, carbonic acid, hydrochloric acid, phosphoric acid, nitric acid and the like. Preferred zinc compounds include, for example, zinc gluconate, zinc sulfate, zinc citrate, zinc carbonate, zinc chloride, zinc phosphate and the like. These may be blended singly or in combination of two or more.
亜鉛化合物の配合量は、これを配合する亜鉛含有経口投与組成物の使用目的により異なる。栄養摂取量の面からは、亜鉛イオンに換算して、1日当たり1〜50mgが好ましく、1日に100mlの内服液剤として摂取する場合、その亜鉛イオン濃度は、0.001〜0.05W/V%である。 The compounding quantity of a zinc compound changes with the intended purposes of the zinc containing oral administration composition which mix | blends this. In terms of nutrient intake, 1 to 50 mg per day is preferable in terms of zinc ions, and when taken as a 100 ml oral solution per day, the zinc ion concentration is 0.001 to 0.05 W / V. %.
本発明におけるポリグリセリン脂肪酸エステルとは、4〜20個のグリセリンが重合したポリグリセリンと炭素数8〜20個の脂肪酸を縮合したエステルであって、HLBが12以上のものである。具体的には、デカグリセリンモノミリスチン酸エステル、ヘキサグリセリンモノミリスチン酸エステル、デカグリセリンモノラウリン酸エステル、ヘキサグリセリンモノラウリン酸エステル、デカグリセリンモノステアリン酸エステル、ヘキサグリセリンモノステアリン酸エステル、デカグリセリンモノカプリル酸エステル、デカグリセリンモノオレイン酸エステル、ヘキサグリセリンモノオレイン酸エステル、デカグリセリンモノリノレン酸エステルなどが挙げられ、その中でもデカグリセリンモノミリスチン酸エステル、デカグリセリンモノステアリン酸エステル、デカグリセリンモノラウリン酸エステルが好ましい。 The polyglycerol fatty acid ester in the present invention is an ester obtained by condensing polyglycerol obtained by polymerization of 4 to 20 glycerol and a fatty acid having 8 to 20 carbon atoms, and has an HLB of 12 or more. Specifically, decaglycerin monomyristic acid ester, hexaglycerin monomyristic acid ester, decaglycerin monolauric acid ester, hexaglycerin monolauric acid ester, decaglycerin monostearic acid ester, hexaglycerin monostearic acid ester, decaglycerin monocaprylic acid Ester, decaglycerin monooleate, hexaglycerin monooleate, decaglycerin monolinolenic acid ester, etc. Among them, decaglycerin monomyristic acid ester, decaglycerin monostearic acid ester, decaglycerin monolauric acid ester are preferable. .
本発明の亜鉛含有経口投与組成物において、ポリグリセリン脂肪酸エステルの配合量は、亜鉛化合物を亜鉛イオンに換算したとき、その亜鉛イオン1質量部に対し0.1質量部以上であり、好ましくは0.5〜2000質量部、さらに好ましくは2.5〜1000質量部である。 In the zinc-containing oral administration composition of the present invention, the amount of polyglycerin fatty acid ester is 0.1 parts by mass or more, preferably 0 with respect to 1 part by mass of zinc ions when the zinc compound is converted into zinc ions. It is 0.5-2000 mass parts, More preferably, it is 2.5-1000 mass parts.
本発明の亜鉛含有経口投与組成物を内服液剤とする場合には、防腐性および風味等を考慮してそのpHを2.5〜7.0、好ましくは3.0〜5.5とする。この内服液剤のpHは、例えば、クエン酸、リンゴ酸、フマル酸、酒石酸、乳酸、コハク酸などの有機酸、これら有機酸の塩、リン酸、塩酸などの無機酸、水酸化ナトリウムなどの無機塩基を添加して調整することができる。 When the zinc-containing composition for oral administration of the present invention is used as an internal solution, the pH is adjusted to 2.5 to 7.0, preferably 3.0 to 5.5 in consideration of preservability and flavor. The pH of the internal solution is, for example, organic acids such as citric acid, malic acid, fumaric acid, tartaric acid, lactic acid, succinic acid, salts of these organic acids, inorganic acids such as phosphoric acid and hydrochloric acid, inorganic acids such as sodium hydroxide, etc. It can be adjusted by adding a base.
本発明の亜鉛含有経口投与組成物には、ビタミン類、ミネラル類、アミノ酸類、生薬、生薬抽出物、カフェイン、ローヤルゼリーなどを本発明の効果を損なわない範囲で適宜に配合できる。また、必要に応じて界面活性剤、抗酸化剤、着色剤、香料、矯味剤、溶解補助剤、保存剤および甘味料などの添加物を本発明の効果を損なわない範囲で適宜に配合できる。 Vitamins, minerals, amino acids, herbal medicines, herbal extracts, caffeine, royal jelly, and the like can be appropriately blended in the zinc-containing oral administration composition of the present invention as long as the effects of the present invention are not impaired. In addition, additives such as surfactants, antioxidants, colorants, fragrances, flavoring agents, solubilizers, preservatives, and sweeteners can be appropriately blended as necessary so long as the effects of the present invention are not impaired.
なお、ポリグリセリン脂肪酸エステルは低温保存時、溶解度が低下し、沈澱や浮遊物を生じ易い。そのため、生薬又は生薬抽出物などの有効成分を配合する場合には、これら有効成分を安定に溶解させるために、ポリオキシエチレン系非イオン性界面活性剤および油成分を配合することが好ましい。 Polyglycerin fatty acid esters have low solubility during storage at low temperatures, and are liable to cause precipitation and floating matters. Therefore, when blending active ingredients such as herbal medicine or herbal extract, it is preferable to blend a polyoxyethylene nonionic surfactant and an oil component in order to dissolve these active ingredients stably.
上記油成分としては、ビタミンE、ビタミンEの誘導体(例えば酢酸、コハク酸等のエステル)、ビタミンA、ビタミンD、ビタミンK、γ−オリザノール、大豆油、中鎖脂肪酸トリグリセリド、γ−リノレン酸等のトリグリセリン脂肪酸エステル等を挙げることができる。これらは1種又は2種以上を混合して用いることができる。生薬又は生薬抽出物などの有効成分を安定に溶解するためには、油成分の配合量をポリグリセリン脂肪酸エステル1質量部に対して0.7質量部以下とすることが望ましい。 Examples of the oil component include vitamin E, derivatives of vitamin E (for example, esters such as acetic acid and succinic acid), vitamin A, vitamin D, vitamin K, γ-oryzanol, soybean oil, medium chain fatty acid triglyceride, γ-linolenic acid, etc. And triglycerin fatty acid esters. These may be used alone or in combination of two or more. In order to dissolve an active ingredient such as a crude drug or a crude drug extract stably, the amount of the oil component is preferably 0.7 parts by mass or less with respect to 1 part by mass of the polyglycerol fatty acid ester.
本発明の亜鉛含有経口投与組成物を調製する方法は特に限定されるものではない。内服液剤とする場合には、通常、各成分を適量の精製水で溶解した後、pHを調整し、残りの精製水を加えて容量調整し、必要に応じて濾過、滅菌処理することにより目的の亜鉛含有経口投与組成物を得ることができる。 The method for preparing the zinc-containing oral administration composition of the present invention is not particularly limited. When using it as an internal solution, the purpose is usually to dissolve each component with an appropriate amount of purified water, adjust the pH, adjust the volume by adding the remaining purified water, and filter and sterilize as necessary. A zinc-containing composition for oral administration can be obtained.
以下に実施例及び試験例を挙げ、本発明をより詳しく説明する。 Hereinafter, the present invention will be described in more detail with reference to examples and test examples.
実施例1
グルコン酸亜鉛 0.08g
ポリグリセリン脂肪酸エステル 0.20g
酢酸トコフェロール 0.10g
硝酸チアミン 0.01g
リン酸リボフラビンナトリウム 0.01g
塩酸ピリドキシン 0.01g
アスコルビン酸 1.00g
アミノエチルスルホン酸 2.00g
キシリトール 4.00g
トレハロース 5.00g
エリスリトール 5.00g
クエン酸 0.80g
クエン酸ナトリウム 適量
安息香酸ナトリウム 0.06g
グリセリン 0.20g
ミックスフルーツフレーバー 0.10g
上記成分を精製水に溶解した後、pHを3.0に調整し、精製水を加えて全量を100mLとした。この液をろ紙でろ過し、滅菌装置を用いて、ろ液を80℃で25分間加熱滅菌した後、ガラス瓶に充填しキャップを施して内服液剤を得た。
Example 1
Zinc gluconate 0.08g
Polyglycerol fatty acid ester 0.20 g
Tocopherol acetate 0.10g
0.01 g of thiamine nitrate
Riboflavin sodium phosphate 0.01 g
0.01 g of pyridoxine hydrochloride
Ascorbic acid 1.00g
Aminoethylsulfonic acid 2.00g
Xylitol 4.00g
Trehalose 5.00g
Erythritol 5.00g
Citric acid 0.80 g
Sodium citrate appropriate amount Sodium benzoate 0.06g
Glycerin 0.20g
0.10g mixed fruit flavor
After dissolving the above components in purified water, the pH was adjusted to 3.0, and purified water was added to make up a total volume of 100 mL. This solution was filtered with a filter paper, and the filtrate was sterilized by heating at 80 ° C. for 25 minutes using a sterilizer, and then filled into a glass bottle and capped to obtain an internal solution.
実施例2
グルコン酸亜鉛 0.04g
ポリグリセリン脂肪酸エステル 0.20g
アルギン酸プロピレングリコール 0.05g
酢酸トコフェロール 0.10g
グルコン酸カルシウム 2.00g
アスパラギン酸マグネシウム 1.00g
硝酸チアミン 0.01g
リボフラビン 0.01g
塩酸ピリドキシン 0.10g
アスコルビン酸 1.00g
アミノエチルスルホン酸 1.00g
ソルビトール 4.00g
トレハロース 5.00g
キシリトール 4.00g
ステビア抽出物 0.03g
アセスルファムカリウム 0.03g
リンゴ酸 0.10g
クエン酸 0.40g
クエン酸ナトリウム 適量
安息香酸 0.06g
パラオキシ安息香酸ブチル 0.006g
パラオキシ安息香酸プロピル 0.006g
グリセリン 0.20g
アップルフレーバー 0.10g
上記成分を精製水に溶解した後、pHを4.0に調整し、精製水を加えて全量を100mLとした。この液をろ紙でろ過し、滅菌装置を用いて、ろ液を80℃で25分間加熱滅菌した後、ガラス瓶に充填しキャップを施して内服液剤を得た。
Example 2
Zinc gluconate 0.04g
Polyglycerol fatty acid ester 0.20 g
Propylene glycol alginate 0.05g
Tocopherol acetate 0.10g
Calcium gluconate 2.00g
Magnesium aspartate 1.00 g
0.01 g of thiamine nitrate
Riboflavin 0.01g
0.10 g of pyridoxine hydrochloride
Ascorbic acid 1.00g
Aminoethylsulfonic acid 1.00g
Sorbitol 4.00g
Trehalose 5.00g
Xylitol 4.00g
Stevia extract 0.03g
Acesulfame potassium 0.03g
Malic acid 0.10g
Citric acid 0.40g
Sodium citrate appropriate amount Benzoic acid 0.06g
Butyl paraoxybenzoate 0.006g
Propyl paraoxybenzoate 0.006 g
Glycerin 0.20g
Apple flavor 0.10g
After dissolving the above components in purified water, the pH was adjusted to 4.0, and purified water was added to make up a total volume of 100 mL. This solution was filtered with a filter paper, and the filtrate was sterilized by heating at 80 ° C. for 25 minutes using a sterilizer, and then filled into a glass bottle and capped to obtain an internal solution.
実施例3
グルコン酸亜鉛 0.08g
ポリグリセリン脂肪酸エステル 0.20g
ショ糖脂肪酸エステル 0.10g
リボフラビン 0.01g
塩酸ピリドキシン 0.01g
アスコルビン酸 1.00g
シアノコバラミン 120μg
パンテノール 0.01g
ニコチン酸アミド 0.05g
アミノエチルスルホン酸 1.00g
ソルビトール 5.00g
トレハロース 2.00g
マルチトール 2.00g
クエン酸 0.40g
リンゴ酸ナトリウム 適量
安息香酸 0.06g
パラオキシ安息香酸ブチル 0.006g
パラオキシ安息香酸プロピル 0.006g
トリカプリリン 0.05g
グリセリン 0.20g
ミックスフルーツフレーバー 0.10g
上記成分を精製水に溶解した後、pHを4.5に調整し、精製水を加えて全量を100mLとした。この液をろ紙でろ過し、滅菌装置を用いて、ろ液を80℃で25分間加熱滅菌した後、ガラス瓶に充填しキャップを施して内服液剤を得た。
Example 3
Zinc gluconate 0.08g
Polyglycerol fatty acid ester 0.20 g
Sucrose fatty acid ester 0.10g
Riboflavin 0.01g
0.01 g of pyridoxine hydrochloride
Ascorbic acid 1.00g
Cyanocobalamin 120μg
Panthenol 0.01g
Nicotinamide 0.05g
Aminoethylsulfonic acid 1.00g
Sorbitol 5.00g
Trehalose 2.00g
Maltitol 2.00g
Citric acid 0.40g
Sodium malate appropriate amount Benzoic acid 0.06g
Butyl paraoxybenzoate 0.006g
Propyl paraoxybenzoate 0.006 g
Tricaprylin 0.05g
Glycerin 0.20g
0.10g mixed fruit flavor
After dissolving the above components in purified water, the pH was adjusted to 4.5, and purified water was added to make up a total volume of 100 mL. This solution was filtered with a filter paper, and the filtrate was sterilized by heating at 80 ° C. for 25 minutes using a sterilizer, and then filled into a glass bottle and capped to obtain an internal solution.
実施例4
グルコン酸亜鉛 0.01g
ポリグリセリン脂肪酸エステル 0.20g
ポリオキシエチレン硬化ヒマシ油 0.10g
トリカプリリン 0.05g
乳酸カルシウム 0.30g
塩化マグネシウム 0.06g
クエン酸鉄アンモニウム 0.05g
硝酸チアミン 0.01g
リン酸リボフラビンナトリウム 0.01g
塩酸ピリドキシン 0.01g
ニコチン酸アミド 0.10g
無水カフェイン 0.10g
アミノエチルスルホン酸 2.00g
塩化カルニチン 0.20g
アルギニン塩酸塩 0.20g
ヨクイニン流エキス 2.00mL
ブドウ糖 5.00g
難消化性デキストリン 4.00g
エリスリトール 5.00g
キシリトール 2.00g
ステビア抽出物 0.02g
アセスルファムカリウム 0.03g
スクラロース 0.05g
クエン酸 0.80g
クエン酸ナトリウム 適量
安息香酸ナトリウム 0.06g
パラオキシ安息香酸ブチル 0.006g
パラオキシ安息香酸プロピル 0.006g
グリセリン 0.20g
ミックスフルーツフレーバー 0.10g
上記成分を精製水に溶解した後、pHを3.5に調整し、精製水を加え全量を100mLとした。この液をろ紙でろ過し、滅菌装置を用いて、ろ液を80℃で25分間加熱滅菌した後、ガラス瓶に充填しキャップを施して内服液剤を得た。
Example 4
Zinc gluconate 0.01g
Polyglycerol fatty acid ester 0.20 g
Polyoxyethylene hydrogenated castor oil 0.10g
Tricaprylin 0.05g
Calcium lactate 0.30g
Magnesium chloride 0.06g
0.05 g of ammonium iron citrate
0.01 g of thiamine nitrate
Riboflavin sodium phosphate 0.01 g
0.01 g of pyridoxine hydrochloride
Nicotinamide 0.10g
Anhydrous caffeine 0.10g
Aminoethylsulfonic acid 2.00g
Carnitine chloride 0.20g
Arginine hydrochloride 0.20g
Yokuinin style extract 2.00mL
Glucose 5.00g
Indigestible dextrin 4.00 g
Erythritol 5.00g
Xylitol 2.00g
Stevia extract 0.02g
Acesulfame potassium 0.03g
Sucralose 0.05g
Citric acid 0.80 g
Sodium citrate appropriate amount Sodium benzoate 0.06g
Butyl paraoxybenzoate 0.006g
Propyl paraoxybenzoate 0.006 g
Glycerin 0.20g
0.10g mixed fruit flavor
After dissolving the above components in purified water, the pH was adjusted to 3.5, and purified water was added to make up a total volume of 100 mL. This solution was filtered with a filter paper, and the filtrate was sterilized by heating at 80 ° C. for 25 minutes using a sterilizer, and then filled into a glass bottle and capped to obtain an internal solution.
実施例5
グルコン酸亜鉛 0.08g
ポリグリセリン脂肪酸エステル 0.20g
ポリオキシエチレン硬化ヒマシ油 0.10g
トリカプリリン 0.05g
グルコン酸カルシウム 2.00g
乳酸カルシウム 1.00g
アスパラギン酸ナトリウム 0.10g
アスパラギン酸マグネシウム 1.00g
硝酸チアミン 0.01g
リン酸リボフラビンナトリウム 0.02g
塩酸ピリドキシン 0.03g
ニコチン酸アミド 0.05g
無水カフェイン 0.10g
アミノエチルスルホン酸 2.00g
ヨクイニン流エキス 2.00mL
ローヤルゼリー 0.60g
ブドウ糖 5.00g
ソルビトール 5.00g
キシリトール 5.00g
ステビア抽出物 0.02g
アセスルファムカリウム 0.03g
クエン酸 0.80g
クエン酸ナトリウム 0.10g
リン酸 0.30g
塩酸 適量
安息香酸ナトリウム 0.06g
パラオキシ安息香酸ブチル 0.006g
パラオキシ安息香酸プロピル 0.006g
グリセリン 0.20g
ミックスフルーツフレーバー 0.10g
上記成分を精製水に溶解した後、pHを3.5に調整し、精製水を加え全量を100mLとした。この液をろ紙でろ過し、滅菌装置を用いて、ろ液を80℃で25分間加熱滅菌した後、ガラス瓶に充填しキャップを施して内服液剤を得た。
Example 5
Zinc gluconate 0.08g
Polyglycerol fatty acid ester 0.20 g
Polyoxyethylene hydrogenated castor oil 0.10g
Tricaprylin 0.05g
Calcium gluconate 2.00g
Calcium lactate 1.00g
Sodium aspartate 0.10g
Magnesium aspartate 1.00 g
0.01 g of thiamine nitrate
Riboflavin sodium phosphate 0.02g
0.03 g of pyridoxine hydrochloride
Nicotinamide 0.05g
Anhydrous caffeine 0.10g
Aminoethylsulfonic acid 2.00g
Yokuinin style extract 2.00mL
Royal jelly 0.60g
Glucose 5.00g
Sorbitol 5.00g
Xylitol 5.00g
Stevia extract 0.02g
Acesulfame potassium 0.03g
Citric acid 0.80 g
Sodium citrate 0.10g
Phosphoric acid 0.30 g
Hydrochloric acid appropriate amount Sodium benzoate 0.06g
Butyl paraoxybenzoate 0.006g
Propyl paraoxybenzoate 0.006 g
Glycerin 0.20g
0.10g mixed fruit flavor
After dissolving the above components in purified water, the pH was adjusted to 3.5, and purified water was added to make up a total volume of 100 mL. This solution was filtered with a filter paper, and the filtrate was sterilized by heating at 80 ° C. for 25 minutes using a sterilizer, and then filled into a glass bottle and capped to obtain an internal solution.
試験例
Hagermanらは、溶液中のタンパク(ウシ血清アルブミン:BSA)がタンニンにより凝集し、その沈澱量はタンニンの量に比例することを報告した(J.Agric.Food.Chem.,1978,Vol.26,809-812)。本発明者らは、亜鉛イオン溶液にBSA溶液を加えると、この溶液が懸濁し、吸光度が減少すること、この吸光度の減少が、亜鉛イオンの濃度に相関することを見出した。これは、ある物質を添加した亜鉛イオン溶液をBSA溶液に混合したときの吸光度が無添加の場合と比較して減少すると、その物質の添加により、タンパク−亜鉛イオン相互作用による凝集(収斂性)が減少したこと、すなわち収斂味が減少したことを意味すると考えられる。
Test example
Hagerman et al. Reported that protein (bovine serum albumin: BSA) in solution was aggregated by tannin, and the amount of precipitation was proportional to the amount of tannin ( J. Agric . Food . Chem ., 1978, Vol. 26 , 809) . -812). The present inventors have found that when a BSA solution is added to a zinc ion solution, the solution is suspended, the absorbance decreases, and this decrease in absorbance correlates with the zinc ion concentration. This is because, when the absorbance when a zinc ion solution containing a certain substance is mixed with a BSA solution decreases compared to the case where no addition is made, the addition of that substance causes aggregation due to protein-zinc ion interaction (convergence). Is considered to mean that the astringent taste has decreased.
試験方法
(1)BSA溶液の調製:BSA(Sigma Chemical Co.;fraction V,fatty acid free)10gを適量の精製水に溶解し、クエン酸100mgを加え、NaOH溶液(1mol/L)でpHを4.8に調整し、精製水で100mLとした。
(2)希釈液の調製:クエン酸100mgを適量の水に溶解し、NaOH溶液(1mol/L)でpHを4.8に調整し、精製水で100mLとした。
(3)亜鉛イオン溶液の調製:グルコン酸亜鉛0.04g、0.19及び0.39gにクエン酸0.10gを加えた。それぞれを適量の精製水に溶解し、NaOH溶液(1mol/L)でpHを4.8に調整し、精製水で100mLとした。
(4)タンパク−亜鉛イオン相互作用(収斂性)の評価
各亜鉛イオン溶液2mLにBSA溶液6mLを加え、希釈液でそれぞれ全量を10mLとした。これを40℃で30分間振とうした。石英セル(L=1cm)を使用し、分光光度計(日立製作所製:U−3300)により、各透明溶液では吸収されない波長である500nmにおける吸光度を測定した。この結果(図1)は、亜鉛イオン濃度と吸光度が相関することを示す。
Test method
(1) Preparation of BSA solution: 10 g of BSA (Sigma Chemical Co .; fraction V, fatty acid free) is dissolved in an appropriate amount of purified water, 100 mg of citric acid is added, and pH is adjusted to 4. with NaOH solution (1 mol / L). 8 and adjusted to 100 mL with purified water.
(2) Preparation of diluting solution: 100 mg of citric acid was dissolved in an appropriate amount of water, the pH was adjusted to 4.8 with NaOH solution (1 mol / L), and adjusted to 100 mL with purified water.
(3) Preparation of zinc ion solution: 0.10 g of citric acid was added to 0.04 g, 0.19 and 0.39 g of zinc gluconate. Each was dissolved in an appropriate amount of purified water, adjusted to pH 4.8 with NaOH solution (1 mol / L), and made up to 100 mL with purified water.
(4) Evaluation of protein-zinc ion interaction (convergence)
6 mL of BSA solution was added to 2 mL of each zinc ion solution, and the total volume was adjusted to 10 mL with the diluent. This was shaken at 40 ° C. for 30 minutes. Using a quartz cell (L = 1 cm), the absorbance at 500 nm, which is a wavelength that is not absorbed by each transparent solution, was measured with a spectrophotometer (manufactured by Hitachi, Ltd .: U-3300). This result (FIG. 1) shows that the zinc ion concentration and the absorbance are correlated.
次に、各種濃度の亜鉛イオン溶液と収斂味(官能評価)との相関を調べた。官能評価は、収斂味が強くて許容できない場合をB、許容することができる範囲をその収斂味の強さに応じてA4〜A1とし、収斂味を全く感じない場合をAとして評価を行った。その結果を図2に示す。図2より、吸光度が約0.4以下であれば、亜鉛イオン由来の収斂味が十分抑制されていると判断した。 Next, the correlation between various concentrations of zinc ion solution and astringency (sensory evaluation) was examined. The sensory evaluation was evaluated as B when the astringent taste was strong and unacceptable, A4 to A1 depending on the strength of the astringent taste, and A when the astringent taste was not felt at all. . The result is shown in FIG. From FIG. 2, when the absorbance was about 0.4 or less, it was judged that the astringent taste derived from zinc ions was sufficiently suppressed.
(5)検体のタンパク凝集性
上記と同様の試験方法により、表1に示す処方のタンパク凝集性を評価した。
(5) Protein aggregation properties of specimens The protein aggregation properties of the formulations shown in Table 1 were evaluated by the same test method as described above.
表1より、ポリグリセリン脂肪酸エステルを配合した検体1および検体2の吸光度は、ポリグリセリン脂肪酸エステルを含有しない検体3よりも小さいことから、ポリグリセリン脂肪酸エステルの配合により、亜鉛イオンに由来する収斂味を低減できることが明らかとなった。 From Table 1, since the absorbance of the sample 1 and the sample 2 containing the polyglycerol fatty acid ester is smaller than that of the sample 3 not containing the polyglycerol fatty acid ester, the astringent taste derived from zinc ions is obtained by blending the polyglycerol fatty acid ester. It has become clear that can be reduced.
本発明により、亜鉛イオンに由来する収斂味を低減し、飲みやすく、しかも不快な後味が残らない亜鉛含有経口投与組成物を提供することができた。この亜鉛含有経口投与組成物は、例えば、シロップ剤、ドリンク剤などの医薬品や医薬部外品を含む各種製剤及び栄養機能食品などの各種飲料に適用できる。 According to the present invention, it is possible to provide a zinc-containing composition for oral administration that reduces the astringent taste derived from zinc ions, is easy to drink, and does not leave an unpleasant aftertaste. This zinc-containing oral administration composition can be applied, for example, to various preparations including pharmaceuticals such as syrups and drinks and quasi-drugs, and various beverages such as nutritional functional foods.
Claims (5)
A method for reducing an unpleasant taste of an orally administered composition containing a zinc compound, comprising blending a polyglycerol fatty acid ester.
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US8399014B2 (en) | 2008-12-24 | 2013-03-19 | Maruha Nichiro Foods, Inc. | Physiologically active complex comprising protamine and/or salt therefor and an acidic macromolecular substance, and use thereof |
WO2019054859A1 (en) * | 2017-09-12 | 2019-03-21 | Purac Biochem B.V. | Meat treatment |
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