JP2023165287A - Squalene water solubilizer and method for producing the same - Google Patents
Squalene water solubilizer and method for producing the same Download PDFInfo
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- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 title claims abstract description 118
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 title claims abstract description 118
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 229940031439 squalene Drugs 0.000 title claims abstract description 118
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 title claims abstract description 118
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 239000002904 solvent Substances 0.000 title claims abstract description 83
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 35
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 17
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 12
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005642 Oleic acid Substances 0.000 claims abstract description 12
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 11
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000008117 stearic acid Substances 0.000 claims abstract description 11
- 239000002245 particle Substances 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 26
- 238000003756 stirring Methods 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 150000004665 fatty acids Chemical group 0.000 claims description 18
- 239000012071 phase Substances 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 9
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 8
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 claims description 7
- 235000013305 food Nutrition 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 244000068988 Glycine max Species 0.000 claims description 3
- 125000005313 fatty acid group Chemical group 0.000 abstract 2
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 239000002253 acid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 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 8
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 7
- 239000000787 lecithin Substances 0.000 description 7
- 229940067606 lecithin Drugs 0.000 description 7
- 235000010445 lecithin Nutrition 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 6
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 6
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 6
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 229940049964 oleate Drugs 0.000 description 5
- 230000000007 visual effect Effects 0.000 description 5
- 229930003427 Vitamin E Natural products 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 4
- 235000019165 vitamin E Nutrition 0.000 description 4
- 229940046009 vitamin E Drugs 0.000 description 4
- 239000011709 vitamin E Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 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 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940069078 citric acid / sodium citrate Drugs 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- 229940110767 coenzyme Q10 Drugs 0.000 description 1
- 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 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010686 shark liver oil Substances 0.000 description 1
- 229940069764 shark liver oil Drugs 0.000 description 1
- 231100000245 skin permeability Toxicity 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
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Abstract
Description
本発明は、スクワレン水溶化剤及びその製造方法に関する。 The present invention relates to a squalene water solubilizing agent and a method for producing the same.
スクワレンは、サメ肝臓に含まれる油（肝油）の成分である。市販のスクワレンのほとんどは、サメ肝油から抽出されたものである。このスクワレンの６大作用として、細胞賦活作用、免疫強化作用、鎮痛作用、殺菌作用、浄化作用、浸透作用が知られている。健康増進に効果的な働きをすることからサプリメント・健康食品として利用されている。また皮膚への浸透性が強いことから化粧品としても広く利用されている。
このように幅広い用途を有するスクワレンではあるが、水に難溶性であり、使い勝手が悪いという課題があった。
この課題を解決するために、乳化剤等を加えることにより、水に溶解させることが試みられている。
Squalene is a component of the oil found in shark liver (cod liver oil). Most commercially available squalene is extracted from shark liver oil. The six major effects of squalene are known to be cell activating, immune strengthening, analgesic, bactericidal, purifying, and penetrating. It is used as a supplement and health food because it is effective in promoting health. It is also widely used in cosmetics because of its strong skin permeability.
Although squalene has such a wide range of uses, it has the problem of being poorly soluble in water and being difficult to use.
In order to solve this problem, attempts have been made to dissolve it in water by adding an emulsifier or the like.
しかしながら、時間の経過と供に、水分とスクワレンが分離してしまうという課題があった。そのため、経時安定性の高い、スクワレン水溶化剤が求められていた。 However, there was a problem in that water and squalene separated over time. Therefore, a squalene water solubilizing agent with high stability over time has been desired.
本発明は以下の内容に関する。
〈１〉 スクワレンと、乳化剤と、水と、を含む水溶化剤であって、スクワレンの含有量は、前記スクワレン水溶化剤の全質量基準で、１８質量％以上であり、乳化剤として、脂肪酸鎖がステアリン酸である乳化剤及び脂肪酸鎖がオレイン酸である乳化剤の少なくとも一方を含むスクワレン水溶化剤。
〈２〉 スクワレンの含有量は、スクワレン水溶化剤の全質量基準で、１８質量％以上３８質量％未満である〈１〉記載のスクワレン水溶化剤。
〈３〉 さらに、リゾレシチンを含有する〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈４〉 スクワレンが、大豆由来スクワレンである〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈５〉 スクワレン水溶化剤の乳化粒子の平均粒子径が１２０～２００ｎｍであり、スクワレン水溶化剤の調製時から調製２カ月後の乳化粒子の平均粒子径の変化率が５％以下である〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈６〉 スクワレン水溶化剤の調製時から調製２カ月後のスクワレン含有量の変化率が５％以下である〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈７〉 スクワレン水溶化剤の調製時から２カ月間酸糖液中に保持した場合の乳化粒子の平均粒子径の変化率が５％以下である〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈８〉 さらに、中鎖脂肪酸油を含む〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈９〉 さらに、グリセリンを含む〈１〉又は〈２〉に記載のスクワレン水溶化剤。
〈１０〉 〈１〉又は〈２〉に記載の前記水溶化剤を含む飲食品。
〈１１〉 乳化剤とグリセリンを７０℃～９０℃で加熱混合して水相を得る工程と、中鎖脂肪酸油を９０℃～１２０℃で加熱混合して油相を得る工程と、水相に油相を撹拌しながら添加して混合物を得る工程と、混合物にスクワレンを撹拌しながら投入する工程と、混合物にイオン交換水を撹拌しながら添加する工程と、を備え、前記乳化剤として、脂肪酸鎖がステアリン酸である乳化剤及び脂肪酸鎖がオレイン酸である乳化剤の少なくとも一方を用いるスクワレン水溶化剤の製造方法。
〈１２〉 混合物にスクワレンを撹拌しながら投入する工程において、さらにリゾレシチンを添加する、〈９〉に記載のスクワレン水溶化剤の製造方法。
The present invention relates to the following contents.
<1> A water solubilizer containing squalene, an emulsifier, and water, wherein the content of squalene is 18% by mass or more based on the total mass of the squalene water solubilizer, and the emulsifier contains a fatty acid chain. A squalene water solubilizer comprising at least one of an emulsifier whose fatty acid chain is stearic acid and an emulsifier whose fatty acid chain is oleic acid.
<2> The squalene water-solubilizing agent according to <1>, wherein the content of squalene is 18% by mass or more and less than 38% by mass, based on the total mass of the squalene water-solubilizing agent.
<3> The squalene water-solubilizing agent according to <1> or <2>, further containing lysolecithin.
<4> The squalene water-solubilizing agent according to <1> or <2>, wherein the squalene is soybean-derived squalene.
<5> The average particle size of the emulsified particles of the squalene water solubilizer is 120 to 200 nm, and the rate of change in the average particle size of the emulsified particles from the time of preparation of the squalene water solubilizer to 2 months after preparation is 5% or less. The squalene water solubilizer described in 1> or <2>.
<6> The squalene water-solubilizing agent according to <1> or <2>, wherein the rate of change in squalene content after two months from the time of preparation of the squalene water-solubilizing agent is 5% or less.
<7> The squalene water soluble according to <1> or <2>, wherein the rate of change in the average particle diameter of the emulsified particles is 5% or less when kept in an acid sugar solution for two months from the time of preparation of the squalene water solubilizer. agent.
<8> The squalene water-solubilizing agent according to <1> or <2>, further comprising a medium-chain fatty acid oil.
<9> The squalene water-solubilizing agent according to <1> or <2>, further comprising glycerin.
<10> A food or drink containing the water solubilizing agent according to <1> or <2>.
<11> A step of heating and mixing an emulsifier and glycerin at 70°C to 90°C to obtain an aqueous phase, a step of heating and mixing medium chain fatty acid oil at 90°C to 120°C to obtain an oil phase, and adding oil to the aqueous phase. The emulsifier includes a step of adding squalene to the mixture while stirring to obtain a mixture, a step of adding squalene to the mixture while stirring, and a step of adding ion-exchanged water to the mixture while stirring. A method for producing a squalene water solubilizer using at least one of an emulsifier whose fatty acid chain is stearic acid and an emulsifier whose fatty acid chain is oleic acid.
<12> The method for producing a squalene water-solubilizing agent according to <9>, wherein lysolecithin is further added in the step of adding squalene to the mixture while stirring.
本発明によれば、経時安定性の高いスクワレン水溶化剤が提供される。 According to the present invention, a squalene water solubilizing agent with high stability over time is provided.
以下に、実施形態を挙げて本発明の説明を行うが、本発明は以下の実施形態に限定されるものではない。 The present invention will be described below with reference to embodiments, but the present invention is not limited to the following embodiments.
本発明は、スクワレンと、乳化剤と、水と、を含むスクワレン水溶化剤であって、スクワレンの含有量が、スクワレン水溶化剤の全質量基準で、１８質量％以上であり、乳化剤として、ステアリン酸及びオレイン酸の少なくとも一方を含む水溶化剤に関する。水溶化剤は、さらにグリセリンを含むことが好ましい。 The present invention provides a squalene water solubilizer containing squalene, an emulsifier, and water, in which the content of squalene is 18% by mass or more based on the total mass of the squalene water solubilizer, and stearin is used as the emulsifier. The present invention relates to a water-solubilizing agent containing at least one of acid and oleic acid. Preferably, the water solubilizing agent further contains glycerin.
スクワレンとしては特に制限なく種々のものを使用することができるが、大豆由来スクワレンであることが好ましい。 Although various types of squalene can be used without particular limitation, soybean-derived squalene is preferred.
スクワレンの含有量は、水溶化剤の全質量基準で、１８質量％以上３８質量％未満であることが好ましい。上記下限値未満となると乳化粒子の粒子径が大きくなり、乳化状態が不安定になるからである。上記上限値以上となると乳化粒子の粒子径が経時的に増加する傾向があるからである。スクワレンの含有量は、水溶化剤の全質量基準で、２０質量％以上３４質量％未満であることがより好ましい。 The content of squalene is preferably 18% by mass or more and less than 38% by mass based on the total mass of the water solubilizing agent. This is because if it is less than the above lower limit, the particle size of the emulsified particles becomes large and the emulsified state becomes unstable. This is because when the above upper limit is exceeded, the particle diameter of the emulsified particles tends to increase over time. The content of squalene is more preferably 20% by mass or more and less than 34% by mass based on the total mass of the water-solubilizing agent.
スクワレン水溶化剤の経時安定性が良好であることの目安としては、乳化粒子の平均粒子径が５０～２００ｎｍであることが挙げられる。本実施形態に係るスクワレン水溶化剤の乳化粒子の平均粒子径は、好ましくは１２０～２００ｎｍであり、さらに好ましくは１４０～２００ｎｍである。乳化粒子の平均粒子径が５０～２００ｎｍの範囲に入ることより、非常に安定性が高いといえる。
乳化粒子の平均粒子径の測定方法としては、例えば、動的光散乱法を用いた装置（大塚電子株式会社製、商品名「ＥＬＳＺ－２０００ＺＳ」）により粒子径を測定することができる。
A standard for good stability over time of a squalene water-solubilizing agent is that the average particle diameter of the emulsified particles is 50 to 200 nm. The average particle diameter of the emulsified particles of the squalene water solubilizer according to the present embodiment is preferably 120 to 200 nm, more preferably 140 to 200 nm. Since the average particle diameter of the emulsified particles falls within the range of 50 to 200 nm, it can be said that the emulsified particles have very high stability.
As a method for measuring the average particle diameter of the emulsified particles, for example, the particle diameter can be measured using a device using a dynamic light scattering method (manufactured by Otsuka Electronics Co., Ltd., trade name "ELSZ-2000ZS").
またスクワレン水溶化剤の経時安定性が良好であることの目安の１つとしては、スクワレン水溶化剤の液滴の調製時から調製２カ月後の平均粒子径の変化率が５％以下であることが挙げられる。本実施形態に係るスクワレン水溶化剤は、乳化粒子の平均粒子径の変化率は５％以下であり、経時安定性が非常に高い。 In addition, one of the indicators that the squalene water-solubilizing agent has good stability over time is that the rate of change in the average particle diameter from the time of preparation of squalene water-solubilizing agent droplets to two months after preparation is 5% or less. This can be mentioned. The squalene water solubilizer according to this embodiment has a change rate of the average particle diameter of emulsified particles of 5% or less, and has very high stability over time.
乳化剤としては、特に制限なく種々のものを使用することができるが、脂肪酸鎖がステアリン酸又はオレイン酸である乳化剤を用いることが好ましい。この場合、両者の一方を含めばよいが両者を含んでもよい。またその他の乳化剤と組み合わせて使用してもよいが、脂肪酸鎖がステアリン酸及び／又はオレイン酸である乳化剤のみを用いることが好ましい。 Although various emulsifiers can be used without particular limitation, it is preferable to use an emulsifier whose fatty acid chain is stearic acid or oleic acid. In this case, one of the two may be included, but both may be included. Although it may be used in combination with other emulsifiers, it is preferable to use only emulsifiers whose fatty acid chains are stearic acid and/or oleic acid.
スクワレン水溶化剤は、油相成分として、さらに中鎖脂肪酸油（Medium Chain Triglyceride：ＭＣＴ）を含有してもよい。スクワレンの酸化安定性が向上するからである。
その他にも、安定性の向上のためビタミンＥ等の酸化防止剤を含有してもよい。
The squalene water solubilizer may further contain medium chain triglyceride (MCT) as an oil phase component. This is because the oxidation stability of squalene is improved.
In addition, antioxidants such as vitamin E may be included to improve stability.
スクワレン水溶化剤は、さらにレシチン及び酵素処理されたレシチンのいずれか一方を含有してもよい。酵素処理されたレシチンとしては、例えば、レシチンの疎水基部分の脂肪酸部分が酵素により分解されることにより、疎水性が低減され相対的に親水性が向上したレシチンを用いることが好ましい。酵素処理されたレシチンの具体例としては、レシチンの脂肪酸残基部分が酵素により加水分解されたリゾレシチンが挙げられる。
スクワレン水溶化剤は、リゾレシチンを含有することが好ましい。スクワレン水溶化剤の経時安定性が向上するからである。
The squalene water solubilizing agent may further contain either lecithin or enzyme-treated lecithin. As the enzyme-treated lecithin, it is preferable to use, for example, lecithin whose hydrophobicity is reduced and whose hydrophilicity is relatively improved by decomposing the fatty acid moiety of the hydrophobic group portion of lecithin with an enzyme. A specific example of enzyme-treated lecithin includes lysolecithin in which the fatty acid residue portion of lecithin is hydrolyzed by an enzyme.
The squalene water solubilizing agent preferably contains lysolecithin. This is because the stability of the squalene water solubilizing agent over time is improved.
実施形態に係るスクワレン水溶化剤は、酸糖液中でも乳化粒子の粒子径の変化が少なく、糖度（Ｂｒｉｘ）耐性が良好であるといえる。
スクワレン水溶化剤の糖度（Ｂｒｉｘ）耐性が良好であることの目安の１つとしては、スクワレン水溶化剤の液滴の調製時から２カ月間、酸糖液中に保持した場合でも乳化粒子の平均粒子径の変化率が５％以下であることが挙げられる。本実施形態に係るスクワレン水溶化剤は、乳化粒子の平均粒子径の変化率は５％以下であり、経時安定性が非常に高い。
The squalene water-solubilizing agent according to the embodiment shows little change in the particle diameter of emulsified particles even in an acid-sugar solution, and can be said to have good sugar content (Brix) resistance.
One of the indicators of good sugar content (Brix) resistance of the squalene water solubilizer is that even when the droplets of the squalene water solubilizer are kept in an acid sugar solution for two months from the time of preparation, the emulsified particles remain The rate of change in average particle diameter is 5% or less. The squalene water solubilizer according to this embodiment has a change rate of the average particle diameter of emulsified particles of 5% or less, and has very high stability over time.
スクワレン水溶化剤は、上述の成分の他に、スクワレンの機能を害することがなく、飲食品に使用した場合に、適用可能なものであれば特に制限なく、種々の成分を添加することができる。例えばコエンザイムＱ１０やビタミンＣ等の美容系のサプリメントと併用することができる。 In addition to the above-mentioned ingredients, the squalene water solubilizing agent may contain various other ingredients without any particular restrictions, as long as they do not impair the function of squalene and are applicable when used in foods and drinks. . For example, it can be used in combination with beauty supplements such as coenzyme Q10 and vitamin C.
（スクワレン水溶化剤の製造方法）
スクワレン水溶化剤は、製造方法に特に制限はないが、例えば、以下の工程を備える製造方法により製造することができる。
（イ）乳化剤とグリセリンを５０℃～９０℃で加熱混合して水相を得る。上記下限値未満となると粘度が高くなり、上記上限値を超えると粘度が低くなるため、上記加熱温度の範囲が好ましい。加熱温度は７０～９０℃がより好ましい。乳化剤としては、脂肪酸鎖がステアリン酸又はオレイン酸であるものを用いることが好ましい。この場合、脂肪酸鎖がステアリン酸であるものと脂肪酸鎖がオレイン酸であるものを併用しても構わない。
（ロ）中鎖脂肪酸油を９０℃～１２０℃で加熱混合して油相を得る。
（ハ）イ工程で得られた水相に、ロ工程で得られた油相を撹拌しながら添加して混合物を得る。水相と油相が混じり合えば攪拌速度に特に制限はないが、撹拌速度は３０００～６０００ｒｐｍが好ましい。
（ニ）混合物にスクワレンを撹拌しながら投入する。
（ホ）混合物にイオン交換水を撹拌しながら添加する。
以上のようにしてスクワレン水溶化剤が製造される。
上記工程に限らず、例えば（イ）工程において、任意成分としてレゾレシチンをさらに添加してもよい。スクワレン水溶化剤の経時安定性が向上するからである。
(Method for producing squalene water solubilizer)
The squalene water solubilizing agent can be manufactured by a manufacturing method including the following steps, for example, although there are no particular restrictions on the manufacturing method.
(a) Heat and mix the emulsifier and glycerin at 50°C to 90°C to obtain an aqueous phase. The above heating temperature range is preferable because the viscosity becomes high when it is below the above lower limit, and the viscosity becomes low when it exceeds the above upper limit. The heating temperature is more preferably 70 to 90°C. As the emulsifier, it is preferable to use one whose fatty acid chain is stearic acid or oleic acid. In this case, a fatty acid whose fatty acid chain is stearic acid and a fatty acid chain whose fatty acid chain is oleic acid may be used together.
(b) Heat and mix medium chain fatty acid oil at 90°C to 120°C to obtain an oil phase.
(c) The oil phase obtained in step B is added to the aqueous phase obtained in step A with stirring to obtain a mixture. There is no particular restriction on the stirring speed as long as the aqueous phase and oil phase are mixed, but the stirring speed is preferably 3000 to 6000 rpm.
(d) Add squalene to the mixture while stirring.
(e) Add ion exchange water to the mixture while stirring.
A squalene water-solubilizing agent is produced as described above.
Not limited to the above steps, for example, resolecithin may be further added as an optional component in step (a). This is because the stability of the squalene water solubilizing agent over time is improved.
（その他の実施形態）
上記のように、本発明は実施形態によって記載したが、この開示の一部をなす論述はこの発明を限定するものであると理解すべきではない。この開示から当業者には様々な代替実施の形態、実施例及び運用技術が明らかとなろう。
スクワレン水溶化剤について中心に説明してきたが、本発明は、上述のスクワレン水溶化剤を含む飲食品にも関する。飲食品としては、例えば、飲料、ゼリー、グミ等が挙げられる。
このように、本発明はここでは記載していない様々な実施の形態等を含むことは勿論である。したがって、本発明の技術的範囲は上記の説明から妥当な特許請求の範囲に係る発明特定事項によってのみ定められるものである。
(Other embodiments)
As mentioned above, although the present invention has been described by way of embodiments, the statements forming a part of this disclosure should not be understood as limiting the present invention. Various alternative embodiments, implementations, and operational techniques will be apparent to those skilled in the art from this disclosure.
Although the description has focused on the squalene water-solubilizing agent, the present invention also relates to foods and drinks containing the above-mentioned squalene water-solubilizing agent. Examples of the food and drink include drinks, jellies, and gummies.
Thus, it goes without saying that the present invention includes various embodiments not described here. Therefore, the technical scope of the present invention is determined only by the matters specifying the invention in the claims that are reasonable from the above description.
以下、実施例により詳細に説明するが、本発明はこれらに限定されるものではない。 Examples will be described in detail below, but the present invention is not limited thereto.
（スクワレン水溶化剤の製造）
（実施例１）
乳化剤としてステアリン酸ポリグリセリル（ＳＶＥＸ：日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-SVEX」、以下「ＳＶＥＸ」ともいう）１０質量部と、グリセリン３４．８２質量部を８０℃で加熱混合して水相を得た。
中鎖脂肪酸油（ＭＣＴ：花王社製、商品名「ココナードＭＴ」、以下「ＭＣＴ」ともいう）５質量部と、ビタミンＣパルミテート（ＶＣＰ）０．０４質量部を９０℃～１２０℃で加熱混合して油相を得た。
水相に油相を６０００ｒｐｍで撹拌しながら添加して混合物を得た。
混合物を４０℃まで冷却した後、混合物に、ビタミンＥ０．０４質量部とスクワレン３５質量部とを６０００ｒｐｍで撹拌しながら投入した。
イオン交換水１５質量部にビタミンＣナトリウム（ＶＣＮａ）０．１質量部を溶解させた。
混合物にＶＣＮａを含むイオン交換水を６０００ｒｐｍで撹拌しながら添加した。
このようにしてスクワレン水溶化剤（試料１）が得られた。各成分の配合率をまとめて表１に示す。
(Manufacture of squalene water solubilizer)
(Example 1)
As an emulsifier, 10 parts by mass of polyglyceryl stearate (SVEX: manufactured by Nikko Chemicals Co., Ltd., product name "NIKKOL Decaglyn 1-SVEX", hereinafter also referred to as "SVEX") and 34.82 parts by mass of glycerin were heated and mixed at 80°C and mixed with water. I got the phase.
5 parts by mass of medium chain fatty acid oil (MCT: manufactured by Kao Corporation, product name "Coconard MT", hereinafter also referred to as "MCT") and 0.04 parts by mass of vitamin C palmitate (VCP) are heated and mixed at 90°C to 120°C. An oil phase was obtained.
The oil phase was added to the water phase while stirring at 6000 rpm to obtain a mixture.
After the mixture was cooled to 40° C., 0.04 parts by mass of vitamin E and 35 parts by mass of squalene were added to the mixture while stirring at 6000 rpm.
0.1 part by mass of vitamin C sodium (VCNa) was dissolved in 15 parts by mass of ion-exchanged water.
Ion exchange water containing VCNa was added to the mixture while stirring at 6000 rpm.
In this way, squalene water solubilizer (Sample 1) was obtained. The blending ratio of each component is summarized in Table 1.
（実施例２）
乳化剤として、ステアリン酸ポリグリセリル（ＳＶＥＸ）を８質量部と、オレイン酸ポリグリセリル（ＯＶＥＸ：日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-OVEX」、以下「ＯＶＥＸ」ともいう）を２質量部用いたことを除き、実施例１と同様にしてスクワレン水溶化剤（試料２）を調製した。
(Example 2)
As emulsifiers, 8 parts by mass of polyglyceryl stearate (SVEX) and 2 parts by mass of polyglyceryl oleate (OVEX: manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-OVEX", hereinafter also referred to as "OVEX") were used. A squalene water solubilizer (sample 2) was prepared in the same manner as in Example 1 except for the following.
（製造安定性）
得られた試料１、試料２について、製造安定性を評価した。
［平均粒子径］
試料をイオン交換水で１.０重量％の濃度になるように希釈した後、動的光散乱法を用いた装置（大塚電子株式会社製、商品名「ＥＬＳＺ－２０００ＺＳ」）により乳化粒子の粒子径を測定した。そして、試料の中からランダムに選んだ乳化粒子の粒子径の平均値を算出することにより平均粒子径をもとめた。
また試料を５０ｍｌ褐色瓶の３本の蓋つき容器に導入し、窒素シールを行い、試料が収められた各容器をそれぞれ４０℃、２５℃、５℃の温度に設定された恒温槽で１ヶ月間保持した後の各試料の乳化粒子の平均粒子径を上述と同様にして測定した。得られた結果をまとめて表２に示す。
The manufacturing stability of the obtained Samples 1 and 2 was evaluated.
[Average particle diameter]
After diluting the sample with ion-exchanged water to a concentration of 1.0% by weight, emulsified particles were collected using a dynamic light scattering device (manufactured by Otsuka Electronics Co., Ltd., trade name: "ELSZ-2000ZS"). The diameter was measured. Then, the average particle diameter was determined by calculating the average value of the particle diameters of emulsified particles randomly selected from among the samples.
In addition, the sample was introduced into three 50ml amber bottles with lids, sealed with nitrogen, and each container containing the sample was placed in a constant temperature bath set at 40℃, 25℃, and 5℃ for 1 month. The average particle diameter of the emulsified particles of each sample after being held for a period of time was measured in the same manner as described above. The obtained results are summarized in Table 2.
表２に示されるように、試料１、試料２において、どの温度に保持した場合であっても、平均粒子径に大きな変化はみられなかった。 As shown in Table 2, in Sample 1 and Sample 2, no significant change was observed in the average particle diameter no matter what temperature they were held at.
［スクワレン含有量］
試料中のスクワレン含有量を、ＨＰＬＣ装置（島津製作所製）を用いて測定した。
また試料を５０ｍｌ褐色瓶の３本の蓋つき容器に導入し、窒素シールを行い、試料が収められた各容器をそれぞれ４０℃、２５℃、５℃の温度に設定された恒温槽で１ヶ月間保持した後の各試料中のスクワレン含有量を測定した。
The squalene content in the sample was measured using an HPLC device (manufactured by Shimadzu Corporation).
In addition, the sample was introduced into three 50ml amber bottles with lids, sealed with nitrogen, and each container containing the sample was placed in a constant temperature bath set at 40℃, 25℃, and 5℃ for 1 month. The squalene content in each sample after holding for a period of time was measured.
表３に示されるように、試料１、試料２は、いずれの条件においても、粒子径の変化はほとんど見られず良好な結果であった。 As shown in Table 3, Sample 1 and Sample 2 had good results with almost no change in particle diameter observed under any conditions.
［耐熱性・耐酸性］
ｐＨ３．０に調整したクエン酸・クエン酸ナトリウム溶液（分散液耐酸性の評価用）またはイオン交換水（分散液耐熱性の評価用）に、各試料を、１質量％の濃度になるように添加・混合した。そして、溶液の温度が８０℃に達するまで加温し、その温度を維持した状態で３０分間加熱殺菌した。その後試料を室温で保持した。試料が室温程度になった後と、室温で１ヶ月保持した後に、乳化粒子の粒子径を上述と同様に測定した。そして、加熱前、加熱後、加熱から１ヶ月後の粒子径の経時変化を観察した。得られた結果をまとめて表４に示す。また得られた試料の状態を目視観察した。得られた結果を図１Ａ（加熱前）、図１Ｂ（加熱後）に示す。
Add each sample to a citric acid/sodium citrate solution (for evaluating dispersion acid resistance) or ion exchange water (for dispersion heat resistance evaluation) adjusted to pH 3.0 to a concentration of 1% by mass. Added and mixed. Then, the solution was heated until the temperature reached 80° C., and heat sterilized for 30 minutes while maintaining that temperature. The samples were then kept at room temperature. After the sample reached room temperature and after being kept at room temperature for one month, the particle diameter of the emulsified particles was measured in the same manner as described above. Then, changes over time in particle diameter were observed before heating, after heating, and one month after heating. The obtained results are summarized in Table 4. In addition, the condition of the obtained sample was visually observed. The obtained results are shown in FIG. 1A (before heating) and FIG. 1B (after heating).
試料１、試料２は、中性、酸性のいずれの条件においても、加熱前後で粒子径の変化はほとんど見られず良好な結果であった。
また目視観察の結果、図１Ａ（加熱前）、図１Ｂ（加熱後）に示すように、試料１、試料２は、中性、酸性のいずれの条件においても、外観に変化は見られなかった。
以上より耐酸性耐熱性が良好であることが示された。
Samples 1 and 2 showed good results, with almost no change in particle size observed before and after heating under both neutral and acidic conditions.
Furthermore, as a result of visual observation, as shown in Figure 1A (before heating) and Figure 1B (after heating), there was no change in the appearance of Sample 1 and Sample 2 under either neutral or acidic conditions. .
From the above, it was shown that acid resistance and heat resistance were good.
［Ｂｒｉｘ耐性］
ｐＨ３．０に調整した酸性溶液に、各試料を、１質量％の濃度になるように添加・混合した。得られた溶液に砂糖を添加して糖度（Ｂｒｉｘ）１０になるように調整した。糖度測定には、デジタル屈折計（アタゴ社製、商品名「ＲＸ－５０００ｉ」）を用いた。そして、溶液の温度が８０℃に達するまで加温し、その温度を維持した状態で３０分間加熱した。その後試料を室温で保持した。試料が室温程度になった後、乳化粒子の粒子径を上述と同様に測定した。得られた結果をまとめて表５に示す。
Each sample was added and mixed to a concentration of 1% by mass to an acidic solution adjusted to pH 3.0. Sugar was added to the resulting solution to adjust the sugar content (Brix) to 10. A digital refractometer (manufactured by Atago Co., Ltd., trade name "RX-5000i") was used for sugar content measurement. Then, the solution was heated until the temperature reached 80° C., and heated for 30 minutes while maintaining that temperature. The samples were then kept at room temperature. After the sample reached room temperature, the particle size of the emulsified particles was measured in the same manner as described above. The obtained results are summarized in Table 5.
表５に示すように、乳化粒子の粒子径に変化はほとんど見られなかった。このことより、糖度（Ｂｒｉｘ）による不安定化は見られないことが確認された。 As shown in Table 5, almost no change was observed in the particle diameter of the emulsified particles. From this, it was confirmed that destabilization due to sugar content (Brix) was not observed.
（参考例１）
乳化剤としてオレイン酸ポリグリセリル（ＯＶＥＸ）１０質量部と、グリセリン３４．８２質量部を８０℃で加熱混合して水相を得た。
中鎖脂肪酸油（ＭＣＴ）５質量部と、ビタミンＣパルミテート（ＶＣＰ）０．０４質量部とを９０℃～１２０℃で加熱混合して油相を得た。
水相に油相を６０００ｒｐｍで撹拌しながら添加して混合物を得た。
混合物を４０℃まで冷却した後、混合物に、ビタミンＥを０．０４質量部とスクワレン３５質量部とを６０００ｒｐｍで撹拌しながら投入した。
イオン交換水１５質量部にビタミンＣナトリウム（ＶＣＮａ）０．１質量部を溶解させた。
混合物にＶＣＮａを含むイオン交換水を６０００ｒｐｍで撹拌しながら添加した。
このようにしてスクワレン水溶化剤（試料３）が得られた。
(Reference example 1)
10 parts by mass of polyglyceryl oleate (OVEX) as an emulsifier and 34.82 parts by mass of glycerin were heated and mixed at 80°C to obtain an aqueous phase.
5 parts by mass of medium chain fatty acid oil (MCT) and 0.04 parts by mass of vitamin C palmitate (VCP) were heated and mixed at 90°C to 120°C to obtain an oil phase.
The oil phase was added to the water phase while stirring at 6000 rpm to obtain a mixture.
After the mixture was cooled to 40° C., 0.04 parts by mass of vitamin E and 35 parts by mass of squalene were added to the mixture while stirring at 6000 rpm.
0.1 part by mass of vitamin C sodium (VCNa) was dissolved in 15 parts by mass of ion-exchanged water.
Ion exchange water containing VCNa was added to the mixture while stirring at 6000 rpm.
In this way, squalene water solubilizer (Sample 3) was obtained.
（参考例２～７）
乳化剤を表６に示す成分に変更したことを除き、参考例１と同様にしてスクワレン水溶化剤（試料４～試料９）を調製した。
なお、表中の試料３～試料９で用いた乳化剤は以下の通りである。
試料３：オレイン酸ポリグリセリル（ＯＶＥＸ）（日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-OVEX」）
試料４：ステアリン酸ポリグリセリル（ＳＶＥＸ）（日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-SVEX」）
試料５：パルミチン酸ポリグリセリル（ＰＶＥＸ）（日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-PVEX」）
試料６：ミリスチン酸ポリグリセリル（ＭＶＥＸ）（日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-MVEX」）
試料７：ラウリン酸ポリグリセリル（ＬＶＥＸ）（日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-LVEX」）
試料８：ステアリン酸ポリグリセリル（５０ＳＶ）（日光ケミカルズ社製、商品名「NIKKOL Decaglyn 1-50SV」）
試料９：オレイン酸ポリグリセリル（Ｑ-１７Ｓ）（太陽化学社製、商品名「サンソフトQ-17S」）
(Reference examples 2 to 7)
Squalene water solubilizers (Samples 4 to 9) were prepared in the same manner as in Reference Example 1, except that the emulsifier was changed to the components shown in Table 6.
The emulsifiers used in Samples 3 to 9 in the table are as follows.
Sample 3: Polyglyceryl oleate (OVEX) (manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-OVEX")
Sample 4: Polyglyceryl stearate (SVEX) (manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-SVEX")
Sample 5: Polyglyceryl palmitate (PVEX) (manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-PVEX")
Sample 6: Polyglyceryl myristate (MVEX) (manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-MVEX")
Sample 7: Polyglyceryl laurate (LVEX) (manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-LVEX")
Sample 8: Polyglyceryl stearate (50SV) (manufactured by Nikko Chemicals, trade name "NIKKOL Decaglyn 1-50SV")
Sample 9: Polyglyceryl oleate (Q-17S) (manufactured by Taiyo Kagaku Co., Ltd., trade name "Sunsoft Q-17S")
試料３～試料９（参考例１～参考例７）について、調製直後と４日後における、目視観察と乳化粒子径の測定を、実施例１の基準に基づいて行った。得られた試料３～試料９の結果を表６にまとめて示す。また４日後の目視観察の結果を図２に示す。
表６や図２に示されるように、試料３（オレイン酸）は４日後に分離しかけていたが、経時安定性が良好であった。試料４、試料８（ステアリン酸）は分離することなく、経時安定性が極めて良好であった。
一方、その他の参考例では、分離が生じていた。このことから、乳化剤として、オレイン酸又はステアリン酸を含むものが好ましいことが分かった。
As shown in Table 6 and FIG. 2, Sample 3 (oleic acid) began to separate after 4 days, but had good stability over time. Samples 4 and 8 (stearic acid) did not separate and had extremely good stability over time.
On the other hand, in other reference examples, separation occurred. From this, it was found that emulsifiers containing oleic acid or stearic acid are preferable.
（実施例３）（比較例１，２）
処方を表７に示す内容に変えたことを除いて、実施例１と同様の方法により、試料１０（実施例３）、試料１１（比較例１）を調製した。試料１２（比較例２）は特許文献１の実施例の方法に準じて調製した。比較例２ではオレイン酸ポリグリセリル（ＯＶＥＸ）とジグリセリンモノオレート(ＤＯ‐１００Ｖ)（理研ビタミン株式会社製、商品名「ポエム」）を使用した。
その後、実施例１、２と同様の方法により各試料の平均粒子径を測定した。得られた結果を表８に示す。
(Example 3) (Comparative Examples 1 and 2)
Sample 10 (Example 3) and Sample 11 (Comparative Example 1) were prepared in the same manner as in Example 1, except that the formulations were changed to those shown in Table 7. Sample 12 (Comparative Example 2) was prepared according to the method of Example of Patent Document 1. In Comparative Example 2, polyglyceryl oleate (OVEX) and diglycerin monooleate (DO-100V) (manufactured by Riken Vitamin Co., Ltd., trade name "Poem") were used.
Thereafter, the average particle diameter of each sample was measured by the same method as in Examples 1 and 2. The results obtained are shown in Table 8.
表８に示すように、スクワレンの配合量が低い試料１１は試作直後から粒子径が４２２．８ｎｍと大きく、乳化が不安定であることが示された。試料１０、試料１２については乳化粒子の平均粒子径が小さく乳化が安定していることが示された。 As shown in Table 8, sample 11 with a low squalene content had a large particle diameter of 422.8 nm immediately after trial production, indicating that emulsification was unstable. For Samples 10 and 12, the average particle diameter of the emulsified particles was small, indicating that the emulsification was stable.
続いて、試料１０、試料１２について、乳化粒子の平均粒子径の経時安定性について、実施例１、２と同様の手法により観察した。得られた結果を表９、表１０にまとめて示す。なお、表中の変動率は下式より求まるものである。表１１、表１２においても同様である。
変動率＝経時での平均粒子径／初期の平均粒子径×１００
Subsequently, regarding Samples 10 and 12, the stability over time of the average particle diameter of the emulsified particles was observed using the same method as in Examples 1 and 2. The obtained results are summarized in Tables 9 and 10. Note that the fluctuation rates in the table are determined from the formula below. The same applies to Tables 11 and 12.
Variation rate = average particle diameter over time / initial average particle diameter x 100
表９に示されるように、試料１０の乳化粒子の平均粒子径に変動はほとんど見られなかった。一方、表１０に示すように、試料１２の乳化粒子の平均粒子径は増加傾向にあり、１１８％まで増加していることが示された。試料１０のほうが試料１２よりも、乳化粒子の平均粒子径の変動が少ないことから、経時安定性が優れていることが示された。 As shown in Table 9, almost no variation was observed in the average particle diameter of the emulsified particles of Sample 10. On the other hand, as shown in Table 10, the average particle diameter of the emulsified particles of Sample 12 was shown to be increasing, increasing to 118%. Sample 10 had less variation in the average particle diameter of the emulsified particles than sample 12, indicating that it had better stability over time.
試料１０、試料１２について、乳化粒子のＢｒｉｘ耐性の経時安定性について、実施例１，２と同様の手法により観察した。得られた結果を表１１、表１２にまとめて示す。 For Samples 10 and 12, the stability over time of the Brix resistance of the emulsified particles was observed using the same method as in Examples 1 and 2. The obtained results are summarized in Tables 11 and 12.
表１１に示されるように、試料１０のスクワレン水溶化剤は、酸糖液中における乳化粒子の平均粒子径の変化が少なく、糖度（Ｂｒｉｘ）耐性が良好であることが示された。
表１２に示されるように、試料１２のスクワレン水溶化剤は、酸糖液中における乳化粒子の平均粒子径の変化は少なかった。
As shown in Table 11, the squalene water solubilizing agent of Sample 10 showed a small change in the average particle diameter of the emulsified particles in the acid-sugar solution, indicating good sugar content (Brix) resistance.
As shown in Table 12, the squalene water solubilizing agent of Sample 12 showed little change in the average particle diameter of the emulsified particles in the acid sugar solution.
（実施例４）
乳化剤としてステアリン酸ポリグリセリル（ＳＶＥＸ）１０質量部と、グリセリン４２．８４質量部を８０℃で加熱混合して水相を得た。
中鎖脂肪酸油（ＭＣＴ）５質量部と、ビタミンＣパルミテート（ＶＣＰ）０．０４質量部を９０℃～１２０℃で加熱混合して油相を得た。
水相に油相を６０００ｒｐｍで撹拌しながら添加して混合物を得た。
混合物を４０℃まで冷却した後、混合物に、ビタミンＥ０．０２質量部とスクワレン２５質量部と、リゾレシチン（協和発酵工業株式会社製、商品名「エルマイザーＡ」）２質量部と、を６０００ｒｐｍで撹拌しながら投入した。
イオン交換水１５質量部にビタミンＣナトリウム（ＶＣＮａ）０．１質量部を溶解させた。
混合物にＶＣＮａを含むイオン交換水を６０００ｒｐｍで撹拌しながら添加した。
このようにしてスクワレン水溶化剤（試料１３）が得られた。各成分の配合率をまとめて表１３に示す。
(Example 4)
10 parts by mass of polyglyceryl stearate (SVEX) as an emulsifier and 42.84 parts by mass of glycerin were heated and mixed at 80°C to obtain an aqueous phase.
5 parts by mass of medium chain fatty acid oil (MCT) and 0.04 parts by mass of vitamin C palmitate (VCP) were heated and mixed at 90°C to 120°C to obtain an oil phase.
The oil phase was added to the water phase while stirring at 6000 rpm to obtain a mixture.
After cooling the mixture to 40°C, 0.02 parts by mass of vitamin E, 25 parts by mass of squalene, and 2 parts by mass of lysolecithin (manufactured by Kyowa Hakko Kogyo Co., Ltd., trade name "Elmizer A") were stirred at 6000 rpm. I put it in while doing so.
0.1 part by mass of vitamin C sodium (VCNa) was dissolved in 15 parts by mass of ion-exchanged water.
Ion exchange water containing VCNa was added to the mixture while stirring at 6000 rpm.
In this way, squalene water solubilizer (Sample 13) was obtained. The blending ratio of each component is summarized in Table 13.
また試料を５０ｍｌ褐色瓶の蓋つき容器に導入し、窒素シールを行い、試料が収められた各容器を４０℃の温度に設定された恒温槽で２ヶ月間保持した後の試料の乳化粒子の平均粒子径の経時変化を上述と同様にして測定した。得られた結果を表１４に示す。 In addition, the sample was introduced into a 50 ml amber bottle with a lid, sealed with nitrogen, and each container containing the sample was kept in a constant temperature bath set at a temperature of 40°C for 2 months. Changes in average particle diameter over time were measured in the same manner as described above. The results obtained are shown in Table 14.
表１４に示されるように、試料１３のスクワレン水溶化剤は、経時変化における乳化粒子の平均粒子径の変化は少なかった。 As shown in Table 14, the squalene water solubilizing agent of Sample 13 showed little change in the average particle diameter of the emulsified particles over time.
なお、２５℃、５℃の温度に設定された恒温槽に２カ月保持した場合においても乳化粒子の平均粒子径の変化は少なかった。またスクワレン含有量、耐熱性・耐酸性、Ｂｒｉｘ耐性についても上述と同様に測定又は観察したところ、それぞれ良好な結果が示された。 Incidentally, even when the emulsified particles were kept in a constant temperature bath set at a temperature of 25° C. or 5° C. for 2 months, there was little change in the average particle diameter of the emulsified particles. In addition, the squalene content, heat resistance/acid resistance, and Brix resistance were also measured or observed in the same manner as described above, and good results were shown for each.
スクワレン水溶化剤は、水に均一に溶解し、耐熱性・耐酸性を有する。スクワレン水溶化剤は経時安定性が良好である。そのため、飲食品に幅広く用いられ得るものである。
スクワレン水溶化剤は、スクワレンを所定の含有量で備えることから、飲食品等に添加する際に非常に使い勝手がよいものである。
The squalene water solubilizer dissolves uniformly in water and has heat resistance and acid resistance. The squalene water solubilizer has good stability over time. Therefore, it can be widely used in food and drink products.
Since the squalene water solubilizing agent contains squalene at a predetermined content, it is very convenient to use when added to foods and drinks.
Claims (12)
前記スクワレンの含有量は、前記スクワレン水溶化剤の全質量基準で、１８質量％以上であり、
前記乳化剤として、脂肪酸鎖がステアリン酸である乳化剤及び脂肪酸鎖がオレイン酸である乳化剤の少なくとも一方を含むスクワレン水溶化剤。 A water solubilizer comprising squalene, an emulsifier, and water,
The squalene content is 18% by mass or more based on the total mass of the squalene water solubilizing agent,
A squalene water solubilizer comprising at least one of an emulsifier whose fatty acid chain is stearic acid and an emulsifier whose fatty acid chain is oleic acid.
中鎖脂肪酸油を９０℃～１２０℃で加熱混合して油相を得る工程と、
前記水相に前記油相を撹拌しながら添加して混合物を得る工程と、
前記混合物にスクワレンを撹拌しながら投入する工程と、
前記混合物にイオン交換水を撹拌しながら添加する工程と、を備え、
前記乳化剤として、脂肪酸鎖がステアリン酸である乳化剤及び脂肪酸鎖がオレイン酸である乳化剤の少なくとも一方を用いるスクワレン水溶化剤の製造方法。 A step of heating and mixing the emulsifier and glycerin at 70°C to 90°C to obtain an aqueous phase;
A step of heating and mixing medium chain fatty acid oil at 90°C to 120°C to obtain an oil phase;
Adding the oil phase to the aqueous phase while stirring to obtain a mixture;
Adding squalene to the mixture while stirring;
adding ion-exchanged water to the mixture while stirring;
A method for producing a squalene water solubilizer using, as the emulsifier, at least one of an emulsifier whose fatty acid chain is stearic acid and an emulsifier whose fatty acid chain is oleic acid.
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