JP7378771B2 - Emulsified composition containing tocopherols - Google Patents
Emulsified composition containing tocopherols Download PDFInfo
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- JP7378771B2 JP7378771B2 JP2019180123A JP2019180123A JP7378771B2 JP 7378771 B2 JP7378771 B2 JP 7378771B2 JP 2019180123 A JP2019180123 A JP 2019180123A JP 2019180123 A JP2019180123 A JP 2019180123A JP 7378771 B2 JP7378771 B2 JP 7378771B2
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- 239000011732 tocopherol Substances 0.000 title claims description 42
- 229930003799 tocopherol Natural products 0.000 title claims description 42
- 239000000203 mixture Substances 0.000 title claims description 27
- 235000019149 tocopherols Nutrition 0.000 title claims description 24
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 title claims description 24
- 239000000839 emulsion Substances 0.000 claims description 20
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 19
- 229960001295 tocopherol Drugs 0.000 claims description 18
- 235000010384 tocopherol Nutrition 0.000 claims description 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- -1 medium chain fatty acid triglycerides Chemical class 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 14
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000004667 medium chain fatty acids Chemical class 0.000 description 3
- WOKDXPHSIQRTJF-UHFFFAOYSA-N 3-[3-[3-[3-[3-[3-[3-[3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)CO WOKDXPHSIQRTJF-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000035622 drinking Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 229940057917 medium chain triglycerides Drugs 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 241000555825 Clupeidae Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
Description
本発明は、難水溶性のトコフェロール類を容易に且つ経済的に水溶化しうるトコフェロール類含有乳化組成物に関する。 The present invention relates to an emulsified composition containing tocopherols that can easily and economically make poorly water-soluble tocopherols water-soluble.
トコフェロール類は栄養の補給や酸化防止剤として広く利用されているが、水溶性が低く、飲料等にそのまま添加することは困難である。 Tocopherols are widely used as nutritional supplements and antioxidants, but their low water solubility makes it difficult to add them directly to drinks and the like.
この問題を解決する方法として、特許文献１並びに特許文献２では、トコフェロール類を油分として用い、ポリグリセリン脂肪酸エステル等の乳化剤を用いて高濃度のトコフェロール類製剤を調製する方法が開示されているが、いずれの技術も油分バランスが限定されているため、製剤の乳化安定性が不十分である。 As a method to solve this problem, Patent Document 1 and Patent Document 2 disclose a method of preparing a highly concentrated tocopherol preparation using tocopherols as an oil component and an emulsifier such as polyglycerin fatty acid ester. Both techniques have limited oil balance, resulting in insufficient emulsion stability of the formulation.
特許文献３では、多価アルコールとして、Ｄ－ソルビトールやデンプン分解物等の糖類を使用する方法が開示されているが、乳化安定性の面でいずれも不十分であるとともに糖類使用のため、飲食物への応用範囲が限定されてしまう。 Patent Document 3 discloses a method of using saccharides such as D-sorbitol and starch decomposition products as polyhydric alcohols, but these methods are insufficient in terms of emulsion stability, and because they use saccharides, they are not suitable for drinking or drinking. The scope of application to objects is limited.
さらに、特許文献４では、乳化剤を用いてトコフェロールを水溶化した製剤が開示されているが、これは煮干しの酸化防止に用いるものであり、飲食物へ直接添加した際の溶解性や安定性等が考慮されていない。 Furthermore, Patent Document 4 discloses a preparation in which tocopherol is made water-soluble using an emulsifier, but this is used to prevent the oxidation of dried sardines, and the solubility and stability when directly added to food and drink are limited. etc. are not taken into consideration.
本発明の目的は、難水溶性のトコフェロール類を容易に且つ経済的に水溶化しうる、安定性の高いトコフェロール類含有乳化組成物を提供することである。 An object of the present invention is to provide a highly stable emulsified composition containing tocopherols that can easily and economically water-solubilize poorly water-soluble tocopherols.
本発明者は、上記課題を解決するため鋭意検討を行った結果、トコフェロール類含有乳化組成物において、中鎖脂肪酸トリグリセリド、２種以上のポリグリセリン脂肪酸エステル（好ましくはＨＬＢが１１以上１６以下の２種以上のポリグリセリン脂肪酸エステル）と水相成分（好ましくは環状構造を取らない直鎖状多価アルコールを含むもの）を組み合わせることで、使用性や経済性、乳化安定性に優れたトコフェロール類含有乳化組成物が得られることを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors found that an emulsified composition containing tocopherols contains medium chain fatty acid triglycerides, two or more types of polyglycerin fatty acid esters (preferably 2 with an HLB of 11 or more and 16 or less). By combining the aqueous phase component (preferably one containing a linear polyhydric alcohol without a cyclic structure), a tocopherol-containing product with excellent usability, economic efficiency, and emulsion stability. It was discovered that an emulsified composition can be obtained, and the present invention was completed.
すなわち、本発明のトコフェロール類含有乳化組成物は、Ａ：油溶性成分としてトコフェロール類及び中鎖脂肪酸トリグリセリド、Ｂ：２種以上のポリグリセリン脂肪酸エステル、Ｃ：水相成分、を含有してなるトコフェロール類含有乳化組成物にかかわるものであり、従来のトコフェロール類を水溶化する技術と比較して、経済性や乳化安定性という面で優れており、製造時の省力化や製品の品質向上に効果があることを特徴とする新規技術である。 That is, the tocopherol-containing emulsified composition of the present invention contains tocopherols containing A: tocopherols and medium-chain fatty acid triglyceride as oil-soluble components, B: two or more types of polyglycerin fatty acid esters, and C: aqueous phase component. This technology is related to emulsified compositions containing tocopherols, and is superior in terms of economy and emulsion stability compared to conventional technology for water-solubilizing tocopherols, and is effective in saving labor during manufacturing and improving product quality. This is a new technology characterized by the following.
本発明によれば、難水溶性のトコフェロール類を容易に且つ経済的に水溶化しうる、安定性の高いトコフェロール類含有乳化組成物を提供することができる。 According to the present invention, it is possible to provide a highly stable tocopherol-containing emulsion composition that can easily and economically water-solubilize poorly water-soluble tocopherols.
本発明に用いられるＡのトコフェロール類は、その種類に特に限定はないが、天然濃縮トコフェロールおよびこれを油脂で希釈したもの、ｄｌ－α－トコフェロールに代表される合成トコフェロール及びそれらの脂肪酸エステル等が挙げられ、これらの市販品を１種または２種以上用いることができる。 The tocopherols A used in the present invention are not particularly limited in type, but include naturally concentrated tocopherols and their diluted forms with fats and oils, synthetic tocopherols typified by dl-α-tocopherol, and fatty acid esters thereof. One or more of these commercially available products can be used.
本発明に用いられる上記トコフェロール類の含有量は、本発明の組成物全体に対して好ましくは２０～３０重量％、より好ましくは２５～３０重量％である。配合量が２０重量％未満であると飲食品等への添加量が増えることになるため経済性が十分ではなく、また３０重量％を超える場合は使用性や乳化安定性が悪くなり好ましくない。 The content of the tocopherols used in the present invention is preferably 20 to 30% by weight, more preferably 25 to 30% by weight based on the entire composition of the present invention. If the amount is less than 20% by weight, the amount added to foods and drinks will increase, which is not economical enough, and if it exceeds 30% by weight, usability and emulsion stability will deteriorate, which is not preferable.
なお、本発明のトコフェロール類含有製剤中の難水溶性物質はトコフェロール類に限らず、他の種類の難水溶性物質と組み合わせることも可能である。例えば、クルクミノイド、カロテノイド、イソプレノイドキノン類などと組み合わせることも可能である。 The poorly water-soluble substance in the tocopherol-containing preparation of the present invention is not limited to tocopherols, but can also be combined with other types of poorly water-soluble substances. For example, it is also possible to combine with curcuminoids, carotenoids, isoprenoid quinones, etc.
本発明に用いられるＡの中鎖脂肪酸トリグリセリドは、ＭＣＴ（Medium Chain Triglycerides）と一般に呼ばれるものであり、炭素数８～１０の飽和脂肪酸から構成されるトリグリセリドであり、無色で低粘度の液状油である。炭素数８～１０の飽和脂肪酸としては、ｎ－オクタン酸、ｎ－ノナン酸、ｎ－デカン酸などが挙げられる。その配合量は特に制限されるものではないが、トコフェロール類に対して好ましくは１重量％以上１０重量％未満であり、より好ましくは４重量％以上８重量％未満である。１重量％未満であれば製剤の安定性が悪くなり、１０重量％以上だと油相の含有量が多くなり乳化が困難になり好ましくない。 The medium-chain fatty acid triglyceride A used in the present invention is generally called MCT (Medium Chain Triglycerides), and is a triglyceride composed of saturated fatty acids having 8 to 10 carbon atoms, and is a colorless, low-viscosity liquid oil. be. Examples of saturated fatty acids having 8 to 10 carbon atoms include n-octanoic acid, n-nonanoic acid, and n-decanoic acid. The amount incorporated is not particularly limited, but is preferably 1% by weight or more and less than 10% by weight, more preferably 4% by weight or more and less than 8% by weight based on the tocopherols. If it is less than 1% by weight, the stability of the formulation will deteriorate, and if it is more than 10% by weight, the content of the oil phase will increase, making emulsification difficult, which is not preferable.
本発明に用いられるポリグリセリン脂肪酸エステルは、平均重合度５以上のポリグリセリンと炭素原子数８～２２の脂肪酸とのエステルである。平均重合度５以上のポリグリセリンとは、例えば、ヘキサグリセリン、オクタグリセリン、デカグリセリンなどが挙げられる。これらを１種または２種以上組み合わせて用いることができる。 The polyglycerin fatty acid ester used in the present invention is an ester of polyglycerin having an average degree of polymerization of 5 or more and a fatty acid having 8 to 22 carbon atoms. Examples of polyglycerin having an average degree of polymerization of 5 or more include hexaglycerin, octaglycerin, and decaglycerin. These can be used alone or in combination of two or more.
炭素原子数８～２２の脂肪酸とは、例えば、カプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸、エルカ酸などが挙げられる。これらを１種または２種以上組み合わせて用いることができる。 Examples of fatty acids having 8 to 22 carbon atoms include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, and erucic acid. These can be used alone or in combination of two or more.
本発明に用いられるポリグリセリン脂肪酸エステルの好ましい例としては、デカ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ミリスチン酸エステル、デカグリセリンモノパルミチン酸エステル、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オレイン酸エステルなどが挙げられる。乳化安定性の観点から、これらを１種類、より好ましくは２種類以上組み合わせて用いることができる。特にデカグリセリンモノステアリン酸エステルとデカグリセリンモノパルミチン酸エステルの組み合わせが好ましい。 Preferred examples of the polyglycerin fatty acid ester used in the present invention include decaglycerin monolaurate, decaglycerin monomyristate, decaglycerin monopalmitate, decaglycerin monostearate, and decaglycerin monooleate. Can be mentioned. From the viewpoint of emulsion stability, one type of these can be used, and more preferably two or more types can be used in combination. Particularly preferred is a combination of decaglycerol monostearate and decaglycerol monopalmitate.
本発明に用いられるＢの２種以上のポリグリセリン脂肪酸エステルは食品用として使用されるものであればいかようなものでも使用できるが、ＨＬＢが１１以上１６以下のものが好ましく、１２以上１５以下のものがさらに好ましい。
ここで、ＨＬＢは、界面活性剤の分野において使用される親水性―疎水性バランスを示すものであり、例えば下記の計算式（川上式）が使用できる。
ＨＬＢ＝７＋１１．７ｌｏｇ（ＭＷ／ＭＯ）
ここで、ＭＷは親水基の分子量、ＭＯは疎水基の分子量である。また、カタログ等に記載されているＨＬＢの数値を使用してもよい。
The two or more types of polyglycerol fatty acid esters B used in the present invention can be of any type as long as they are used for food, but those with an HLB of 11 or more and 16 or less are preferable, and 12 or more and 15 or less. More preferred is
Here, HLB indicates the hydrophilicity-hydrophobicity balance used in the field of surfactants, and for example, the following calculation formula (Kawakami formula) can be used.
HLB=7+11.7log(M W /M O )
Here, M W is the molecular weight of the hydrophilic group, and M O is the molecular weight of the hydrophobic group. Alternatively, the HLB values listed in catalogs or the like may be used.
本発明に用いられる上記ポリグリセリン脂肪酸エステルの含有量は、製剤の性状に影響がない限りは特に限定されるものではないが、好ましくは１０重量％以上２０重量％以下である。１０重量％未満であれば希釈液の耐酸性が悪くなり、２０重量％を超えると粘度が高くなり製造上に支障が生じる。 The content of the polyglycerol fatty acid ester used in the present invention is not particularly limited as long as it does not affect the properties of the preparation, but is preferably 10% by weight or more and 20% by weight or less. If it is less than 10% by weight, the acid resistance of the diluted liquid will be poor, and if it exceeds 20% by weight, the viscosity will become high, causing problems in production.
本発明に用いられるＣの水相成分として好ましいのは水である。水としては飲用可能なものであればよく、その配合量としては好ましくは４０重量％以下、より好ましくは３０重量％以下である。４０重量％を超えるとトコフェロール類の配合量が制限されるため、経済的に不利である。 Water is preferred as the aqueous phase component of C used in the present invention. The water may be any drinkable water, and its amount is preferably 40% by weight or less, more preferably 30% by weight or less. If it exceeds 40% by weight, the amount of tocopherols to be blended is limited, which is economically disadvantageous.
本発明に用いられるＣの水相成分には、環状構造を取らない直鎖型多価アルコールを含めることが好ましい。該直鎖状多価アルコールは食品に使用可能なものであれば特に制限はないが、グリセリンを使用することが好ましい。また、その配合量は好ましくは油相と同量以上であり、より好ましくは１．３倍以上２．５倍以下である。油相と同量未満であれば製造時の粘度が上昇するため好ましくない。 The aqueous phase component C used in the present invention preferably contains a linear polyhydric alcohol that does not have a cyclic structure. The linear polyhydric alcohol is not particularly limited as long as it can be used in foods, but it is preferable to use glycerin. Further, the blending amount thereof is preferably at least the same amount as the oil phase, and more preferably at least 1.3 times and at most 2.5 times. If the amount is less than the same amount as the oil phase, the viscosity during production will increase, which is not preferable.
本発明のトコフェロール類乳化組成物には、製剤の性状に影響がない限り、食品用に用いられるものであれば他の添加剤等を配合することが可能である。例えば、酸化防止剤、ｐＨ調整剤、粘度調整剤等が挙げられる。 The tocopherol emulsified composition of the present invention may contain other additives as long as they are used for foods, as long as they do not affect the properties of the preparation. Examples include antioxidants, pH adjusters, viscosity adjusters, and the like.
次に実施例を挙げて本発明を詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples.
［実施例１～３、比較例１～４］
実施例１～３、比較例１～４のトコフェロール類含有乳化組成物を以下の方法にしたがって製造した。すなわち、表１に示す配合割合（数値の単位は質量％）の乳化剤、多価アルコールを加熱溶解し（水相）、ホモミキサー等の乳化機で混合しながら、トコフェロール類、中鎖脂肪酸トリグリセリド（構成脂肪酸が炭素数８及び１０の脂肪酸からなるもの）を混合したもの（油相）を添加した。更に水を添加し、均質化処理を行うことで、トコフェロール類含有乳化組成物を得た（実施例１～３、比較例１～４）。これらの乳化組成物に対して以下に述べる評価を行った。
[Examples 1 to 3, Comparative Examples 1 to 4]
The tocopherol-containing emulsion compositions of Examples 1 to 3 and Comparative Examples 1 to 4 were produced according to the following method. That is, the emulsifier and polyhydric alcohol in the proportions shown in Table 1 (the units of mass %) are heated and dissolved (aqueous phase), and mixed with an emulsifying machine such as a homomixer, tocopherols, medium chain fatty acid triglycerides ( A mixture (oil phase) of constituent fatty acids consisting of fatty acids having 8 and 10 carbon atoms was added. By further adding water and performing a homogenization treatment, tocopherol-containing emulsion compositions were obtained (Examples 1 to 3, Comparative Examples 1 to 4). These emulsified compositions were evaluated as described below.
［乳化粒子径］
実施例１～３、比較例１～４で得られた前記乳化組成物をそれぞれ水に１％希釈し、その際の乳化粒子径（ｎｍ）をレーザー式光散乱法により測定した。
[Emulsification particle size]
The emulsion compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 4 were each diluted with water by 1%, and the emulsion particle diameter (nm) was measured by a laser light scattering method.
［乳化安定性］
実施例１～３、比較例１～４で得られた前記乳化組成物の前記水希釈液を２５℃に設定した恒温槽に保管し、１ヶ月後に当該乳化組成物の水希釈液の乳化粒子径の変化を測定し、以下の基準に基づいて乳化安定性を評価した。
◎：乳化粒子径の変化が２０ｎｍ以下である。
○：乳化粒子径の変化が５０ｎｍ以下である。
△：乳化粒子径の変化が５０ｎｍ以上であるが、外観に沈殿や分離などの変化が認められない。
×：外観に沈殿や分離などの変化が認められる。
[Emulsification stability]
The water diluted solutions of the emulsified compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 4 were stored in a constant temperature bath set at 25°C, and after one month, the emulsified particles of the water diluted emulsified compositions were Changes in diameter were measured and emulsion stability was evaluated based on the following criteria.
◎: Change in emulsified particle diameter is 20 nm or less.
○: Change in emulsified particle diameter is 50 nm or less.
Δ: Change in emulsified particle size is 50 nm or more, but no change in appearance such as precipitation or separation is observed.
×: Changes such as precipitation and separation are observed in appearance.
［水分散性］
実施例１～３、比較例１～４で得られた前記乳化組成物をそれぞれ水に１％希釈し、スターラーで撹拌し、分散状態を目視で確認し、以下の基準に基づいて水分散性を評価した。
◎：撹拌２０秒以内に均一に分散する。
○：撹拌３０秒以内に均一に分散する。
△：撹拌６０秒以内に均一に分散する。
×：撹拌６０秒後に、溶け残りが目視で確認される。
[Water dispersibility]
The emulsion compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 4 were each diluted with water by 1%, stirred with a stirrer, and the dispersion state was visually confirmed, and the water dispersibility was determined based on the following criteria. was evaluated.
◎: Uniformly dispersed within 20 seconds of stirring.
○: Uniformly dispersed within 30 seconds of stirring.
Δ: Uniformly dispersed within 60 seconds of stirring.
×: After 60 seconds of stirring, undissolved residue is visually confirmed.
［分散液耐熱性、分散液耐酸性］
分散液の耐熱性、耐酸性の評価として、トコフェロール含有量が１０ｍｇ／１００ｍＬになるように、実施例１～３、比較例１～４で得られた乳化組成物をイオン交換水（耐熱性評価用）、ｐＨ３の酸性水（耐酸性評価用）でそれぞれ希釈し、８５℃で３０分間加熱し、加熱前後の乳化粒子径の変化を確認し、以下の基準に基づいて分散液の耐熱性、耐酸性をそれぞれ評価した。
◎：加熱前後で乳化粒子径の変化が２０ｎｍ以下である。
○：加熱前後で乳化粒子径の変化が５０ｎｍ以下である。
△：加熱前後で乳化粒子の変化が５０ｎｍ以上であるが、外観に油浮きや沈殿が生じていない。
×：加熱前後の外観に、油浮きや沈殿が生じている。
◎：イオン交換水希釈液と酸性希釈液で乳化粒子径の差が２０ｎｍ以下である。
○：イオン交換水希釈液と酸性希釈液で乳化粒子径の差が５０ｎｍ以下である。
△：イオン交換水希釈液と酸性希釈液で乳化粒子径の差が５０ｎｍ以上であるが、外観に油浮きや沈殿が生じていない。
×：酸性希釈液の外観に、油浮きや沈殿が生じている。
[Dispersion liquid heat resistance, dispersion liquid acid resistance]
To evaluate the heat resistance and acid resistance of the dispersion liquid, the emulsion compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 4 were mixed with ion-exchanged water (heat resistance evaluation) so that the tocopherol content was 10 mg/100 mL. diluted with pH 3 acidic water (for acid resistance evaluation), heated at 85°C for 30 minutes, confirmed the change in emulsified particle size before and after heating, and evaluated the heat resistance of the dispersion based on the following criteria. Acid resistance was evaluated.
◎: Change in emulsified particle diameter before and after heating is 20 nm or less.
○: The change in emulsion particle diameter before and after heating is 50 nm or less.
Δ: The emulsified particles change by 50 nm or more before and after heating, but there is no oil floating or precipitation in the appearance.
×: Oil floating and precipitation are observed in the appearance before and after heating.
◎: The difference in emulsion particle diameter between the ion exchange water diluted solution and the acidic diluted solution is 20 nm or less.
Good: The difference in emulsion particle diameter between the ion exchange water diluted solution and the acidic diluted solution is 50 nm or less.
Δ: The difference in emulsified particle size between the ion-exchanged water diluted solution and the acidic diluted solution is 50 nm or more, but no oil floating or precipitation is observed in the appearance.
×: Oil floating and precipitation are observed in the appearance of the acidic diluted solution.
［経済性］
実施例１～３、比較例１～４で得られた乳化組成物におけるトコフェロール含有量により以下の基準に基づいて経済性を判断した。
◎：トコフェロール含有量が２１重量％以上である。
○：トコフェロール含有量が１６重量％以上２１重量％未満である。
△：トコフェロール含有量が１１重量％以上１６重量％未満である。
×：トコフェロール含有量が１１重量％未満である。
[Economy]
Economic efficiency was determined based on the tocopherol content in the emulsified compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 4 based on the following criteria.
◎: Tocopherol content is 21% by weight or more.
○: Tocopherol content is 16% by weight or more and less than 21% by weight.
Δ: Tocopherol content is 11% by weight or more and less than 16% by weight.
×: Tocopherol content is less than 11% by weight.
［総合評価］
前述した乳化安定性、水分散性、分散液耐熱性、分散液耐酸性、経済性の評価結果を勘案することにより、総合的な評価を以下の基準で行った。
◎：非常に良い
○：かなり良い
△：やや良い
×：悪い
[comprehensive evaluation]
By taking into account the evaluation results of emulsion stability, water dispersibility, dispersion heat resistance, dispersion acid resistance, and economic efficiency described above, a comprehensive evaluation was performed based on the following criteria.
◎: Very good ○: Fairly good △: Fairly good ×: Bad
表１から明らかなように、中鎖脂肪酸トリグリセリド、ＨＬＢが１２以上１５以下の２種以上のポリグリセリン脂肪酸エステル、環状構造を取らない直鎖状多価アルコールを組み合わせた実施例１～３は経済性に優れ、且つ乳化安定性や水分散性も良い評価が得られた。
As is clear from Table 1, Examples 1 to 3 in which a medium chain fatty acid triglyceride, two or more types of polyglycerin fatty acid esters having an HLB of 12 to 15, and a linear polyhydric alcohol without a cyclic structure are combined are economical. It had excellent properties, and also received good evaluations for emulsion stability and water dispersibility.
Claims (4)
前記Ａのトコフェロール類の含有量が、組成物全体に対して２０～３０質量％であり、
前記Ｂのポリグリセリン脂肪酸エステルの平均重合度が、５以上であるトコフェロール類含有乳化組成物。 A: Contains tocopherols and medium chain fatty acid triglycerides as oil-soluble components, B: Two or more types of polyglycerin fatty acid esters, C: Water phase component ,
The content of tocopherols in A is 20 to 30% by mass based on the entire composition,
An emulsified composition containing tocopherols , wherein the average degree of polymerization of the polyglycerol fatty acid ester (B) is 5 or more .
The tocopherol-containing emulsified composition according to any one of claims 1 to 3 , wherein the emulsified particle size is less than 200 nm.
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