JP2006129841A - alpha-LIPOIC ACID-CONTAINING AQUEOUS COMPOSITION - Google Patents
alpha-LIPOIC ACID-CONTAINING AQUEOUS COMPOSITION Download PDFInfo
- Publication number
- JP2006129841A JP2006129841A JP2004325567A JP2004325567A JP2006129841A JP 2006129841 A JP2006129841 A JP 2006129841A JP 2004325567 A JP2004325567 A JP 2004325567A JP 2004325567 A JP2004325567 A JP 2004325567A JP 2006129841 A JP2006129841 A JP 2006129841A
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- JP
- Japan
- Prior art keywords
- lipoic acid
- component
- aqueous composition
- containing aqueous
- fatty 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.)
- Pending
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- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 229960002663 thioctic acid Drugs 0.000 claims abstract description 95
- 235000019136 lipoic acid Nutrition 0.000 claims abstract description 94
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims abstract description 84
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 44
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- 150000004665 fatty acids Chemical class 0.000 claims abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 6
- 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 17
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- 210000004185 liver Anatomy 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
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- 235000020640 mackerel 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
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- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 235000020679 tap water Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
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- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
本発明は、α−リポ酸含有水性組成物、およびこれを原材料とする飲食品に関する。さらに、詳しくはα−リポ酸の安定性が高く、耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物、およびこれを原材料とする飲食品に関する。 The present invention relates to an α-lipoic acid-containing aqueous composition and a food or drink using the same as a raw material. More specifically, the present invention relates to an α-lipoic acid-containing aqueous composition having high stability of α-lipoic acid and excellent heat resistance, acid resistance, and salt resistance, and a food and drink using this as a raw material.
α−リポ酸は生体内に含まれ、糖の代謝、ＴＣＡサイクルの回転に作用する補酵素の一種であり、構造式Ｃ８Ｈ１４Ｏ２Ｓ２、分子量２０６．３の化合物である。その物性としては、黄色結晶、融点６０〜６２℃の物質として知られている。α−リポ酸は、ヒトにおけるエネルギー生産において、酸化的脱炭酸反応のコファクターとして重要な役割を自然に果たしており、多くの研究において、強力な細胞酸化還元調節剤、内因性「抗酸化剤」の再生物質、および酸化ストレスの軽減物質であることが認められているなど、高い生理活性を持ち、かつ生体内に存在する安全性の高い物質と考えられている。α−リポ酸は、２００４年度の政府による食薬区分見直しにより、食品への使用が認められ、乳化液、可溶化液、分散液等の水性飲食食品への応用が期待されている。
α−リポ酸を用いた医薬品は、α−リポ酸を塩として水溶化したり、α−リポ酸そのものを錠剤化している。（例えば、特許文献１）
A pharmaceutical product using α-lipoic acid is water-soluble as a salt of α-lipoic acid, or tablets of α-lipoic acid itself. (For example, Patent Document 1)
しかし、α−リポ酸は重合し易く、保存安定性の良いα−リポ酸含有水性組成物を製造することは難しかった。さらに、α−リポ酸は独特の硫黄臭を持つが、これを抑制することは難しかった。
さらに、α−リポ酸含有水性組成物を飲食品分野において使用する際、加工時に加温したり、他の素材と組み合わせて使用するため、耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物を製造する必要がある。
本発明の目的は、保存安定性に優れ、耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物を提供することにある。さらに、α−リポ酸の硫黄臭を抑制したα−リポ酸含有水性組成物を提供することにある。そして、α−リポ酸含有水性組成物を原材料とする食味がよく、保存時の安定性に優れた飲食品を提供することにある。
However, α-lipoic acid is easily polymerized, and it has been difficult to produce an α-lipoic acid-containing aqueous composition having good storage stability. Furthermore, although α-lipoic acid has a unique sulfur odor, it was difficult to suppress this.
Furthermore, when the α-lipoic acid-containing aqueous composition is used in the field of foods and drinks, it is heated during processing or used in combination with other materials, so that α-lipoides excellent in heat resistance, acid resistance and salt resistance are used. There is a need to produce an acid-containing aqueous composition.
An object of the present invention is to provide an α-lipoic acid-containing aqueous composition that is excellent in storage stability and excellent in heat resistance, acid resistance, and salt resistance. Furthermore, it is providing the alpha-lipoic acid containing aqueous composition which suppressed the sulfur smell of alpha-lipoic acid. And it is providing the food / beverage products which are good in the taste which uses the alpha-lipoic acid containing aqueous composition as a raw material, and were excellent in stability at the time of a preservation | save.
本発明の第１の発明は、下記のＡ成分を０．０００１〜２０重量％，Ｂ成分を０．０００１〜５０重量％、およびＡ成分１重量部に対して０．０１〜１０重量部のＣ成分を含有し、連続相が水であるα−リポ酸含有水性組成物である。
Ａ：α−リポ酸、
Ｂ：平均重合度３〜１０のポリグリセリンと炭素数１２〜１８の脂肪酸からなるポリグリセリン脂肪酸エステル、
Ｃ：結晶化抑制剤
The first invention of the present invention comprises 0.0001 to 20% by weight of the following component A, 0.0001 to 50% by weight of component B, and 0.01 to 10 parts by weight with respect to 1 part by weight of component A. An α-lipoic acid-containing aqueous composition containing a component C and having a continuous phase of water.
A: α-lipoic acid,
B: polyglycerin fatty acid ester comprising polyglycerin having an average degree of polymerization of 3 to 10 and fatty acid having 12 to 18 carbon atoms,
C: Crystallization inhibitor
本発明の第２の発明は、Ｃ成分の結晶化抑制剤が、プロピレングリコール脂肪酸エステル、グリセリン脂肪酸エステル、ショ糖脂肪酸エステル、レシチン及びリゾレシチンからなる群から選ばれる一つ又はこれらの組み合わせである第１の発明のα−リポ酸含有水性組成物である。 According to a second aspect of the present invention, the C component crystallization inhibitor is one selected from the group consisting of propylene glycol fatty acid ester, glycerin fatty acid ester, sucrose fatty acid ester, lecithin and lysolecithin, or a combination thereof. It is the alpha-lipoic acid containing aqueous composition of 1 invention.
本発明の第３の発明は、さらにＤ成分として抗酸化剤をＡ成分１重量部に対して０．１〜１０重量部含有する第１又は２の発明のα−リポ酸含有水性組成物である。 The third invention of the present invention is the α-lipoic acid-containing aqueous composition of the first or second invention, further comprising 0.1 to 10 parts by weight of an antioxidant as D component with respect to 1 part by weight of component A. is there.
本発明の第４の発明は、Ｄ成分の抗酸化剤がα−トコフェロールおよびアスタキサンチンを含有する抗酸化剤である第３の発明のα−リポ酸含有水性組成物である。 A fourth invention of the present invention is the α-lipoic acid-containing aqueous composition of the third invention, wherein the antioxidant of component D is an antioxidant containing α-tocopherol and astaxanthin.
本発明の第５の発明は、さらにＥ成分として、ＨＬＢが８以上のショ糖脂肪酸エステルをＢ成分１重量部に対して０．００１〜１０重量部含有する第１〜４のいずれかの発明のα−リポ酸含有水性組成物である。
である。
The fifth invention of the present invention is any one of the first to fourth inventions further comprising 0.001 to 10 parts by weight of a sucrose fatty acid ester having an HLB of 8 or more as an E component with respect to 1 part by weight of the B component. [Alpha] -lipoic acid-containing aqueous composition.
It is.
本発明の第６の発明は、第１〜第５の発明のいずれか１つの発明のα−リポ酸含有水性組成物を原材料とする飲食品である。 6th invention of this invention is the food-drinks which use as a raw material the alpha-lipoic acid containing aqueous composition of any one invention of 1st-5th invention.
本発明の第１あるいは２の発明によれば、保存時のα−リポ酸の安定性が高く、かつ、耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物が提供される。本発明のα−リポ酸含有水性組成物は長期間保存しても、α−リポ酸がポリマーを形成することなく保存安定性が高いので、クリーミングを生じたりα−リポ酸が分離、析出、沈殿することなく、均一な乳化または可溶化または分散の状態を保つことができる。したがって、発明のα−リポ酸含有水性組成物は、飲料の原料として好適に使用できる。
本発明の第３の発明によれば、第１又は２の発明において、より耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物が提供され、さらに硫黄臭がより抑制される。
本発明の第４の発明によれば、第３の発明において、より耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物が提供され、さらに硫黄臭がより抑制される。
本発明の第５の発明によれば、第１〜４の発明において、より保存安定性が高く、耐熱性、耐酸性に優れたα−リポ酸含有水性組成物が提供される。
本発明の第６の発明によれば、α−リポ酸含有水性組成物を飲食品の原材料に使用すると、食味がよく、保存時の安定性に優れた飲食品が提供される。そして、粒子径が２００ｎｍ以下のα−リポ酸含有水性組成物を使用すると、摂食時には効率よくこれらの成分を生体に吸収させることのできる飲食品が提供される。
According to the first or second invention of the present invention, there is provided an α-lipoic acid-containing aqueous composition having high stability of α-lipoic acid during storage and excellent heat resistance, acid resistance and salt resistance. The Even if the α-lipoic acid-containing aqueous composition of the present invention is stored for a long period of time, α-lipoic acid has high storage stability without forming a polymer, so that creaming occurs or α-lipoic acid is separated and precipitated. Uniform emulsification or solubilization or dispersion can be maintained without precipitation. Therefore, the α-lipoic acid-containing aqueous composition of the invention can be suitably used as a raw material for beverages.
According to the third invention of the present invention, in the first or second invention, an α-lipoic acid-containing aqueous composition that is more excellent in heat resistance, acid resistance, and salt resistance is provided, and the sulfur odor is further suppressed. The
According to the fourth invention of the present invention, in the third invention, an α-lipoic acid-containing aqueous composition that is more excellent in heat resistance, acid resistance, and salt resistance is provided, and the sulfur odor is further suppressed.
According to the fifth invention of the present invention, in the first to fourth inventions, an α-lipoic acid-containing aqueous composition having higher storage stability and excellent heat resistance and acid resistance is provided.
According to the sixth aspect of the present invention, when the α-lipoic acid-containing aqueous composition is used as a raw material for foods and drinks, foods and drinks having good taste and excellent stability during storage are provided. And if the alpha-lipoic acid containing aqueous composition with a particle diameter of 200 nm or less is used, the food / beverage products which can make a living body absorb these components efficiently at the time of eating are provided.
本発明は、α−リポ酸（Ａ成分）、特定の種類のポリグリセリン脂肪酸エステル（Ｂ成分）および結晶化抑制剤（Ｃ成分）を特定量含有するα−リポ酸含有水性組成物である。 The present invention is an α-lipoic acid-containing aqueous composition containing a specific amount of α-lipoic acid (component A), a specific type of polyglycerin fatty acid ester (component B) and a crystallization inhibitor (component C).
ここで、本発明で用いるＡ成分であるα−リポ酸は、Ｒ，Ｓ−（＋／−）−α−リポ酸、Ｒ−（＋）−α−リポ酸、Ｓ−（−）−α−リポ酸等が挙げられる。
本発明において、組成物中におけるα−リポ酸のα−リポ酸含有水性組成物中における含有量は０．０００１〜２０重量％、好ましくは０．００１〜１５重量％、さらに好ましくは０．１〜１０重量％である。α−リポ酸の含有量が２０重量％を超えると、α−リポ酸含有水性組成物の保存時の安定性が悪くなる。
α−リポ酸の市販品としては、例えばデグサテクスチュラントシステムズ ジャパン(株) 製の商品名：ＡＬＩＰＵＲＥ、立山化成(株) 製の商品名：α−リポ酸（チオクト酸）、コグニス(株) 製の商品名：Ｌｉｐｏｅｃ等が挙げられる。これらのα−リポ酸は、天然由来のものであっても、合成品であってもよい。
Here, α-lipoic acid as the component A used in the present invention is R, S-(+/−)-α-lipoic acid, R-(+)-α-lipoic acid, S-(−)-α. -Lipoic acid etc. are mentioned.
In the present invention, the content of α-lipoic acid in the α-lipoic acid-containing aqueous composition in the composition is 0.0001 to 20% by weight, preferably 0.001 to 15% by weight, more preferably 0.1. -10% by weight. If the α-lipoic acid content exceeds 20% by weight, the stability of the α-lipoic acid-containing aqueous composition during storage deteriorates.
As a commercial product of α-lipoic acid, for example, trade name: ALIPURE manufactured by Degustex Texturant Systems Japan Co., Ltd., trade name: manufactured by Tateyama Kasei Co., Ltd .: α-lipoic acid (thioctic acid), Cognis Co., Ltd. Product name: Lipoec, etc. These α-lipoic acids may be naturally derived or synthetic.
本発明は、Ｂ成分として平均重合度３〜１０のポリグリセリンと炭素数１２〜１８の脂肪酸からなるポリグリセリン脂肪酸エステルを使用することを特徴とする。平均重合度が２以下のポリグリセリン脂肪酸エステルあるいは、炭素数が１１以下の脂肪酸からなるポリグリセリン脂肪酸エステルを使用すると、安定なα−リポ酸含有水性組成物を製造することが難しくなる。
Ｂ成分のα−リポ酸含有水性組成物中の含有量は０．０００１〜５０重量％、好ましくは０．０１〜４５重量％、さらに好ましくは１〜４０重量％である。Ｂ成分の含有量が０．０００１重量％より少ないと本発明のα−リポ酸含有水性組成物の安定性が悪くなる。また、５０重量％より多いとα−リポ酸含有水性組成物の粘性が高くなり調製が難しくなるだけでなく、ポリグリセリン脂肪酸エステル独特の風味が最終製品に影響し好ましくない。
平均重合度３〜１０のポリグリセリンと炭素数１２〜１８の脂肪酸からなるポリグリセリン脂肪酸エステルの市販品としては、例えば、阪本薬品工業（株）製の商品名：ＳＹグリスターＭＬ−７５０、太陽化学（株）製の商品名：サンソフトＱ−１２Ｓ、同Ａ−１７１Ｅ、同Ｑ−１７Ｓ、理研ビタミン（株）製の商品名：ポエムＪ−００２１、同Ｊ−００８１Ｈ等が挙げられる。
なお、上記ポリグリセリン脂肪酸エステルは脂肪酸のモノエステルであることが好ましいが、製造の性質上、モノエステルだけでなく、若干のジエステルやトリエステルを含んでいてもよい。また、これらのポリグリセリン脂肪酸エステルは、１種単独で、あるいは２種以上混合して使用することができる。
The present invention is characterized in that a polyglycerin fatty acid ester composed of polyglycerin having an average degree of polymerization of 3 to 10 and a fatty acid having 12 to 18 carbon atoms is used as the B component. If a polyglycerin fatty acid ester having an average degree of polymerization of 2 or less or a polyglycerin fatty acid ester comprising a fatty acid having 11 or less carbon atoms is used, it becomes difficult to produce a stable α-lipoic acid-containing aqueous composition.
The content of the B component in the α-lipoic acid-containing aqueous composition is 0.0001 to 50% by weight, preferably 0.01 to 45% by weight, more preferably 1 to 40% by weight. When content of B component is less than 0.0001 weight%, stability of the alpha-lipoic acid containing aqueous composition of this invention will worsen. On the other hand, when the content is more than 50% by weight, not only is the viscosity of the α-lipoic acid-containing aqueous composition high and the preparation becomes difficult, but also the unique flavor of the polyglycerin fatty acid ester affects the final product.
As a commercial item of the polyglycerol fatty acid ester which consists of a polyglycerol with an average degree of polymerization of 3-10 and a C12-C18 fatty acid, for example, Sakamoto Pharmaceutical Co., Ltd. product name: SY Glister ML-750, Taiyo Kagaku Trade name: Sunsoft Q-12S, A-171E, Q-17S, Riken Vitamin Co., Ltd. Trade names: Poem J-0021, J-0081H, etc.
The polyglycerin fatty acid ester is preferably a monoester of a fatty acid, but may contain not only a monoester but also some diesters or triesters due to the properties of production. These polyglycerin fatty acid esters can be used alone or in combination of two or more.
本発明のＣ成分である結晶化抑制剤は、α−リポ酸の結晶化を抑制できる化合物であり、一般に油脂の結晶化抑制剤として知られている化合物を使用できる。例えば、プロピレングリコール脂肪酸エステル、グリセリン脂肪酸エステル、ショ糖脂肪酸エステル、レシチン、リゾレシチン等を使用することができる。これらの化合物のＨＬＢは８未満であることが、その結晶抑制効果において好ましい。Ｃ成分は、これらの結晶化抑制剤の群から選ばれる一つ又はこれらの組み合わせとして使用できる。
Ｃ成分の含有量はＡ成分１重量部に対して０．０１〜１０重量部、好ましくは０．０５〜８重量部である。Ｃ成分の含有量が、Ａ成分１重量部％に対して０．０５重量部より少ないと水性組成物の保存安定性が低下するだけでなく、α−リポ酸が重合体を形成し沈殿を生じるなどの問題があり、好ましくない。また、１０重量部より多いとα−リポ酸含有水性組成物の粘性が高くなり調製が難しくなるだけでなく、結晶化抑制剤の風味が最終製品に影響し好ましくない。
The crystallization inhibitor which is the C component of the present invention is a compound that can suppress crystallization of α-lipoic acid, and a compound generally known as a crystallization inhibitor of fats and oils can be used. For example, propylene glycol fatty acid ester, glycerin fatty acid ester, sucrose fatty acid ester, lecithin, lysolecithin and the like can be used. The HLB of these compounds is preferably less than 8 in terms of the crystal suppression effect. The component C can be used as one selected from the group of these crystallization inhibitors or a combination thereof.
Content of C component is 0.01-10 weight part with respect to 1 weight part of A component, Preferably it is 0.05-8 weight part. If the content of component C is less than 0.05 parts by weight with respect to 1 part by weight of component A, not only the storage stability of the aqueous composition is lowered, but also α-lipoic acid forms a polymer and precipitates. There are problems such as occurrence, which is not preferable. On the other hand, when the amount is more than 10 parts by weight, not only the viscosity of the α-lipoic acid-containing aqueous composition becomes high and the preparation becomes difficult, but also the flavor of the crystallization inhibitor affects the final product, which is not preferable.
本発明において、Ｃ成分の結晶化抑制剤は市販品を使用することができる。
プロピレングリコール脂肪酸エステルの市販品としては、例えば、理研ビタミン（株）製の商品名：リケマールＰＳ−１００、同ＰＯ−１００Ｖ、同ＰＰ−１００、同ＰＢ−１００、太陽化学(株)製の商品名：サンソフトＮｏ．２５ＢＤ、同Ｎｏ．２５ＣＤ、同Ｎｏ．２５ＯＤ等が挙げられる。
グリセリン脂肪酸エステルの市販品としては、例えば、理研ビタミン（株）製の商品名：ポエムＪ−４６Ｂ、太陽化学(株)製の商品名：サンファットＰＳ−６６、同ＰＳ−６８、阪本薬品工業(株)製の商品名：ＴＨＬ−３、同１５等が挙げられる。
ショ糖脂肪酸エステルの市販品としては、例えば、太陽化学(株)製の商品名：サンソフトＳＥ−７、三菱化学フーズ(株)製の商品名：リョートーシュガーエステルＳ−０７０、同Ｓ−５７０、同Ｐ−０７０、同Ｏ−０７０、同Ｌ−１９５、同Ｌ−５９５、同Ｂ−３７０、同ＥＲ−１９０、同ＥＲ−２９０等が挙げられる。
レシチンの市販品としては、例えば、太陽化学（株）製の商品名：サンレシチンＬ−８、同Ｌ−６、理研ビタミン（株）製の商品名：レシオンＰ等が挙げられる。
ショ糖脂肪酸エステルの純度としては、製造の性質上、モノエステルだけでなく、若干のジエステルやトリエステルを含んでいてもよい。
リゾレシチンの市販品としては、例えば、太陽化学（株）製の商品名：サンレシチンＡ、同Ｗ−１、理研ビタミン（株）製の商品名：レシマールＥＬ、キューピー（株）製の卵黄レシチンＬＰＬ−１０Ｐ等が挙げられる。なお、上記のレシチンおよびリゾレシチンとしては、天然由来のものであっても、合成品であってもよい。
また、これらの結晶化抑制剤は、１種単独で、あるいは２種以上混合して使用することができる。
In the present invention, a commercially available product can be used as the C component crystallization inhibitor.
As a commercial item of propylene glycol fatty acid ester, for example, product names manufactured by Riken Vitamin Co., Ltd .: Riquemar PS-100, PO-100V, PP-100, PB-100, products manufactured by Taiyo Kagaku Co., Ltd. Name: Sunsoft No. 25BD, no. 25CD, No. 25OD etc. are mentioned.
Commercially available products of glycerin fatty acid esters include, for example, trade names manufactured by Riken Vitamin Co., Ltd .: Poem J-46B, and product names manufactured by Taiyo Kagaku Co., Ltd .: Sun Fat PS-66, PS-68, Sakamoto Pharmaceutical Co., Ltd. Trade name: THL-3, 15 and the like, manufactured by KK
Examples of commercially available sucrose fatty acid esters include trade names manufactured by Taiyo Kagaku Co., Ltd .: Sunsoft SE-7, trade names manufactured by Mitsubishi Chemical Foods Co., Ltd .: Ryoto Sugar Esters S-070, S- 570, P-070, O-070, L-195, L-595, B-370, ER-190, ER-290, and the like.
As a commercial item of a lecithin, the product name: Sun lecithin L-8, the same L-6, the Riken vitamin Co., Ltd. brand name made by Taiyo Kagaku Co., Ltd., etc. are mentioned, for example.
The purity of the sucrose fatty acid ester may include some diesters and triesters as well as monoesters due to the properties of production.
As a commercial product of lysolecithin, for example, trade names manufactured by Taiyo Kagaku Co., Ltd .: Sun lecithin A, W-1, trade names manufactured by Riken Vitamin Co., Ltd .: Recimar EL, egg yolk lecithin LPL manufactured by Kewpie Co., Ltd. -10P etc. are mentioned. The above lecithin and lysolecithin may be naturally derived or synthetic.
Moreover, these crystallization inhibitors can be used singly or in combination of two or more.
本発明のα−リポ酸含有水性組成物において、さらにＤ成分である抗酸化剤を含むと、耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物が製造でき、さらに硫黄臭がより抑制されるので好ましい。
本発明で用いるＤ成分である抗酸化剤の含有量は、Ａ成分１重量部に対して０．１〜１０重量部、好ましくは１〜８重量部である。Ｄ成分の含有量が１０重量部より多いとα−リポ酸含有水性組成物の粘性が高くなり調製が難しくなり好ましくない。
抗酸化剤としては抗酸化能を持つものであれば特に制限はなく、ミックストコフェロール、α−トコフェロール、β−トコフェロール、γ−トコフェロール、δ−トコフェロール、アスタキサンチン、γ−オリザノール、カテキン、ゴマ油抽出物、生コーヒー豆抽出物、米糠油抽出物、ユーカリ葉抽出物、ローズマリー抽出物、ヒノキチオール、トコトリエノール、プロポリス抽出物、アスコルビン酸およびそれらの塩類、アスコルビン酸脂肪酸エステル、ユビキノンなどが挙げられ、これらを単独で、または適宜組み合わせて用いることができる。また、これらの純度は特に制限はなく、天然由来のものであっても、合成品であってもよい。
抗酸化剤の市販品としては、例えば、理研ビタミン(株)製の商品名：リケンＥオイル、富士化学工業(株)製の商品名：アスタリールオイル５０Ｆ、築野食品工業(株)製の商品名：米胚芽油、エーザイ(株)の商品名：トコリット−９２などが挙げられる。
さらに、本発明において、α−トコフェロールおよびアスタキサンチンを含む抗酸化剤を用いると、より耐熱性、耐酸性、耐塩性に優れたα−リポ酸含有水性組成物を製造でき、さらに硫黄臭がより抑制されるので好ましい。α−トコフェロールとアスタキサンチンの比率はα−トコフェロール１重量部に対してアスタキサンチン０．１〜１０重量部であることが、好ましい。
In the α-lipoic acid-containing aqueous composition of the present invention, when an antioxidant as component D is further included, an α-lipoic acid-containing aqueous composition excellent in heat resistance, acid resistance, and salt resistance can be produced, and sulfur Since an odor is suppressed more, it is preferable.
Content of the antioxidant which is D component used by this invention is 0.1-10 weight part with respect to 1 weight part of A component, Preferably it is 1-8 weight part. When the content of component D is more than 10 parts by weight, the viscosity of the α-lipoic acid-containing aqueous composition becomes high and preparation becomes difficult, which is not preferable.
Antioxidant is not particularly limited as long as it has antioxidant ability, mixed tocopherol, α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, astaxanthin, γ-oryzanol, catechin, sesame oil extract, Examples include raw coffee bean extract, rice bran oil extract, eucalyptus leaf extract, rosemary extract, hinokitiol, tocotrienol, propolis extract, ascorbic acid and salts thereof, ascorbic acid fatty acid ester, ubiquinone, etc. Or can be used in appropriate combination. Moreover, there is no restriction | limiting in particular in these purity, The thing of a natural origin or a synthetic product may be sufficient.
Commercially available antioxidants include, for example, trade names manufactured by Riken Vitamin Co., Ltd .: Riken E Oil, trade names manufactured by Fuji Chemical Industry Co., Ltd .: Asteril Oil 50F, manufactured by Tsukino Food Industries Co., Ltd. Trade name: Rice germ oil, trade name of Eisai Co., Ltd .: Tokorit-92 and the like.
Furthermore, in the present invention, when an antioxidant containing α-tocopherol and astaxanthin is used, an α-lipoic acid-containing aqueous composition having more excellent heat resistance, acid resistance, and salt resistance can be produced, and the sulfur odor is further suppressed. This is preferable. The ratio of α-tocopherol and astaxanthin is preferably 0.1 to 10 parts by weight of astaxanthin with respect to 1 part by weight of α-tocopherol.
本発明のα−リポ酸含有水性組成物において、さらに、Ｅ成分として、ＨＬＢが８以上のショ糖脂肪酸エステルを含有すると、より保存安定性が高く、耐熱性、耐酸性に優れたα−リポ酸含有水性組成物を製造することができるので好ましい。
このショ糖脂肪酸エステルの含有量は、Ｂ成分１重量部に対して０．００１〜１０重量部、好ましくは０．１〜８重量部である。１０重量部より多いとα−リポ酸含有水性組成物の粘性が高くなり調製が難しくなるだけでなく、ショ糖脂肪酸エステルの風味が最終製品に影響し好ましくない。
ＨＬＢが８以上のショ糖脂肪酸エステルの市販品としては、太陽化学（株）製の商品名：サンソフトＳＥ−１６Ｐ、同ＳＥ−１１、三菱化学フーズ（株）製の商品名：リョートーシュガーエステルＳ−１６７０、同Ｐ−１６７０、同Ｍ−１６９５、同Ｏ−１５７０、同Ｌ−１６９５、第一工業製薬（株）製の商品名：ＤＫエステルＳＳ、同Ｆ−１６０等が挙げられる。
In the α-lipoic acid-containing aqueous composition of the present invention, when the sucrose fatty acid ester having an HLB of 8 or more is further contained as the E component, the α-lipoic acid has higher storage stability and excellent heat resistance and acid resistance. Since an acid-containing aqueous composition can be manufactured, it is preferable.
Content of this sucrose fatty acid ester is 0.001-10 weight part with respect to 1 weight part of B components, Preferably it is 0.1-8 weight part. When the amount is more than 10 parts by weight, not only the viscosity of the α-lipoic acid-containing aqueous composition becomes high and the preparation becomes difficult, but also the flavor of the sucrose fatty acid ester affects the final product, which is not preferable.
Commercial products of sucrose fatty acid esters having an HLB of 8 or more include trade names manufactured by Taiyo Kagaku Co., Ltd .: Sunsoft SE-16P, SE-11, Mitsubishi Chemical Foods Co., Ltd .: Ryoto Sugar Examples include Ester S-1670, P-1670, M-1695, O-1570, L-1695, trade names manufactured by Daiichi Kogyo Seiyaku Co., Ltd .: DK Ester SS, F-160, and the like.
本発明で使用する水は、飲食品に配合できる水であれば特に制限はなく、例えば、イオン交換水、蒸留水等の精製水、水道水、天然水、アルカリイオン水等が挙げられる。また、これは水のみであっても、その他に食品添加物を加えた水であってもよい。食品添加物としては、ビタミン類、界面活性剤、安定剤、調味料、酸および塩などが挙げられる。 If the water used by this invention is water which can be mix | blended with food-drinks, there will be no restriction | limiting in particular, For example, purified water, such as ion-exchange water and distilled water, tap water, natural water, alkali ion water, etc. are mentioned. In addition, this may be water alone or water with food additives added thereto. Examples of food additives include vitamins, surfactants, stabilizers, seasonings, acids and salts.
本発明においてα−リポ酸含有水性組成物には、他に、本発明の効果を損なわない範囲において、その他の界面活性剤を混合して使用してもかまわない。これらの界面活性剤としては、具体的には例えば、ソルビタン脂肪酸エステル、グリセリン脂肪酸エステル、プロピレングリコール脂肪酸エステル、ショ糖脂肪酸エステル、レシチン、サポニン、ステロール、コール酸、デオキシコール酸、ユッカ抽出物、陽イオン性界面活性剤、陰イオン性界面活性剤、両性界面活性剤などがある。 In the present invention, the α-lipoic acid-containing aqueous composition may be mixed with other surfactants as long as the effects of the present invention are not impaired. Specific examples of these surfactants include sorbitan fatty acid ester, glycerin fatty acid ester, propylene glycol fatty acid ester, sucrose fatty acid ester, lecithin, saponin, sterol, cholic acid, deoxycholic acid, yucca extract, positive Examples include ionic surfactants, anionic surfactants, and amphoteric surfactants.
さらに、本発明のα−リポ酸含有水性組成物中には、安定剤を添加することができる。 本発明に用いる安定剤としては、ガム質や多価アルコール、糖類などが挙げられる。具体的には例えば、アラビアガム、キサンタンガム、トラガントガム、グアガム、ジェランガム、ローカストビーンガム、エチレングリコール、プロピレングリコール、グリセリン、マルチトール、還元水あめ、ラクチトール、パラチニット、エリスリトール、ソルビトール、マンニトール、ブドウ糖果糖液糖、加糖ブドウ糖液糖、デキストリン、乳糖などが挙げられる。これらの安定剤は、５〜４０重量％の水を含むものであってもよく、１種単独で、あるいは２種以上混合して使用することができる。 Furthermore, a stabilizer can be added to the α-lipoic acid-containing aqueous composition of the present invention. Examples of the stabilizer used in the present invention include gums, polyhydric alcohols, and sugars. Specifically, for example, gum arabic, xanthan gum, gum tragacanth, guar gum, gellan gum, locust bean gum, ethylene glycol, propylene glycol, glycerin, maltitol, reduced starch syrup, lactitol, palatinit, erythritol, sorbitol, mannitol, glucose fructose liquid sugar, Examples include sugar-added glucose liquid sugar, dextrin, and lactose. These stabilizers may contain 5 to 40% by weight of water, and can be used alone or in combination of two or more.
さらに、本発明のα−リポ酸含有水性組成物中には、食用油脂を添加することができる。本発明に用いる食用油脂としては、特に制限はなく、一般に食用油脂である動物、植物、微生物を原料とする油脂または合成油等を使用できる。例えば、豚脂、牛脂、鶏油、鯨油、マグロ油、イワシ油、サバ油、サンマ油、カツオ油、ニシン油、肝油、大豆油、綿実油、サフラワー油、米油、コーン油、ナタネ油、パーム油、シソ油、エゴマ油、カカオ脂、落花生油、ヤシ油等、および中鎖脂肪酸トリグリセリド等の合成トリグリセリド等が挙げられ、これらを単独で、または適宜組み合わせて用いることができる。
これらの中でも、パーム油、ヤシ油、中鎖脂肪酸トリグリセリドなどの比較的短鎖の脂肪酸を含む油脂を用いるとα−リポ酸含有水性組成物の安定性が更に向上するので好ましい。
Furthermore, edible fats and oils can be added to the α-lipoic acid-containing aqueous composition of the present invention. There is no restriction | limiting in particular as edible oil and fat used for this invention, The fats and oils or synthetic oil etc. which use the animal, plant, microorganisms which are generally edible fats and oils as a raw material can be used. For example, lard, beef tallow, chicken oil, whale oil, tuna oil, sardine oil, mackerel oil, saury oil, bonito oil, herring oil, liver oil, soybean oil, cottonseed oil, safflower oil, rice oil, corn oil, rapeseed oil, Examples include palm oil, perilla oil, sesame oil, cocoa butter, peanut oil, coconut oil, and synthetic triglycerides such as medium chain fatty acid triglycerides, which can be used alone or in appropriate combination.
Among these, it is preferable to use fats and oils containing relatively short-chain fatty acids such as palm oil, coconut oil, and medium-chain fatty acid triglycerides because the stability of the α-lipoic acid-containing aqueous composition is further improved.
さらに、本発明のα−リポ酸含有水性組成物中には、その他の機能性素材を添加することができる。本発明に用いるその他の機能性素材としては抽出カロチン等の着色料、カプシカム油、グレープフルーツ油等の香料、シソ抽出物、ショウガ抽出物、オクタコサノール、ポリコサノール、セラミド、ホスファチジルセリン、植物ステロール、脂溶性ビタミン類など生理効果を期待できる機能性素材が挙げられ、これらを単独で、または適宜組み合わせて用いることができる。 Furthermore, other functional materials can be added to the α-lipoic acid-containing aqueous composition of the present invention. Other functional materials used in the present invention include colorants such as extracted carotene, fragrances such as capsicum oil and grapefruit oil, perilla extract, ginger extract, octacosanol, policosanol, ceramide, phosphatidylserine, plant sterol, fat-soluble vitamin Functional materials that can be expected to have a physiological effect, such as a class, can be mentioned, and these can be used alone or in appropriate combination.
本発明のα−リポ酸含有水性組成物は、連続相が水であるα−リポ酸の可溶化液、乳化液、あるいは分散液であるが、平均粒径２００ｎｍ以下のα−リポ酸含有水性組成物であることが好ましい。平均粒径が２００ｎｍ以下ではα−リポ酸含有水性組成物の安定性が向上するばかりか、摂食時には効率よくこれらの成分を生体に吸収させることのできるので好ましい。 The α-lipoic acid-containing aqueous composition of the present invention is an α-lipoic acid solubilized solution, emulsion, or dispersion having a continuous phase of water, but has an average particle size of 200 nm or less. A composition is preferred. An average particle size of 200 nm or less is preferable because not only the stability of the α-lipoic acid-containing aqueous composition is improved, but also these components can be efficiently absorbed by the living body when ingested.
本発明の粒径が２００ｎｍ以下のα−リポ酸含有水性組成物は、例えば、Ａ成分のα−リポ酸、Ｂ成分の特定の種類のポリグリセリン脂肪酸エステル、Ｃ成分の結晶化抑制剤、Ｄ成分の抗酸化剤、Ｅ成分のショ糖脂肪酸エステル、水等を特定量含有する組成物に均質機で高剪断力を与えることで剪断力を与えることにより得られる。例えば、本発明のα−リポ酸含有水性組成物は上記の組成物に、均質機により４９ＭＰａ以上の剪断力を与えることで製造される。 The α-lipoic acid-containing aqueous composition having a particle diameter of 200 nm or less according to the present invention includes, for example, α-lipoic acid as component A, a specific type of polyglycerol fatty acid ester as component B, a crystallization inhibitor for component C, D It is obtained by applying a shearing force by applying a high shearing force with a homogenizer to a composition containing a specific amount of an antioxidant as a component, a sucrose fatty acid ester as an E component, water and the like. For example, the α-lipoic acid-containing aqueous composition of the present invention is produced by applying a shearing force of 49 MPa or more to the above composition using a homogenizer.
具体的には、以下の工程１〜３からなる製造方法より本発明のα−リポ酸含有水性組成物を製造することができる。
工程１；Ｂ成分、場合によってはＥ成分およびその他の成分を、所定量はかり取り、水に加熱溶解する。この場合は、６０〜８０℃で加熱溶解することが好ましい。
工程２；Ａ成分及びＣ成分、場合によってはＤ成分を、３０℃に加温し混合した後、これを前記工程１で加熱溶解したものに加える。
工程３；均質化機械を用いて均質化を行なう。
さらに前記工程２の後に、ホモミキサー等により工程３の前処理を行ってもよい。
Specifically, the α-lipoic acid-containing aqueous composition of the present invention can be produced by a production method comprising the following steps 1 to 3.
Step 1: The B component, optionally the E component and other components are weighed in a predetermined amount and dissolved in water by heating. In this case, it is preferable to melt by heating at 60 to 80 ° C.
Step 2: A component and C component, and optionally D component, are heated to 30 ° C. and mixed, and then added to those heated and dissolved in step 1 above.
Step 3: Homogenization is performed using a homogenizing machine.
Furthermore, after the step 2, the pretreatment of the step 3 may be performed by a homomixer or the like.
前記の工程で行う均質化処理を行うための均質化機械としては、例えば、マイクロフルイダイザー（みづほ工業（株）製、商品名）、アルティマイザー（（株）スギノマシン製、商品名）などの均質化処理機を使用できる。均質化処理の圧力は４９ＭＰａ以上、より好ましくは１００ＭＰａ以上、さらに好ましくは１５０ＭＰａ以上の剪断力を与える方法が挙げられる。圧力を掛けると、より粒子径の微細な水溶性組成物が得られる。
また前記の均質化処理はホモミキサー等として、例えば、ＴＫホモミキサー（特殊機化工業（株）製、商品名）、クレアミックス（エム・テクニック（株）製、商品名）等が挙げられる。攪拌羽の周速は７５０ｍ／分以上、より好ましくは１０００ｍ/分以上、さらに好ましくは１５００ｍ／分以上の剪断力を与える方法等が挙げられる。
また、均質化処理は外にも、ナノマイザー、超音波乳化機等の均質化処理機やアジホモミキサー、ウルトラミキサーなどの各種のホモミキサーを用いることができる。
脂溶性ビタミン類含有組成物をより小粒径化して安定化させるために、この均質化処理を２回以上行うことが望ましい。
Examples of the homogenizing machine for performing the homogenizing treatment performed in the above process include a microfluidizer (manufactured by Mizuho Kogyo Co., Ltd., trade name), an optimizer (manufactured by Sugino Machine Co., Ltd., trade name), and the like. A homogenizer can be used. A method of applying a shearing force of 49 MPa or more, more preferably 100 MPa or more, and further preferably 150 MPa or more is used as the pressure for the homogenization treatment. When pressure is applied, a water-soluble composition having a finer particle diameter is obtained.
Examples of the homogenization treatment include a homomixer and the like, such as TK homomixer (trade name, manufactured by Tokushu Kika Kogyo Co., Ltd.) and Claremix (trade name, manufactured by M Technique Co., Ltd.). The peripheral speed of the stirring blade is 750 m / min or more, more preferably 1000 m / min or more, and still more preferably 1500 m / min or more.
In addition to the homogenization treatment, various homomixers such as a homogenizer such as a nanomizer and an ultrasonic emulsifier, an azide homomixer, and an ultramixer can be used.
In order to stabilize the fat-soluble vitamins-containing composition by reducing the particle size, it is desirable to perform this homogenization treatment twice or more.
本発明のα−リポ酸含有水性組成物を含有する飲食品としては、例えば、パン、ビスケット、キャンディー、ゼリーなどのパン・菓子類や、ヨーグルト、ハムなどの乳肉加工食品や味噌、ソース、タレ、ドレッシングなどの調味料や豆腐、めん類などの加工食品やマーガリン、ファットスプレッド、ショートニングなどの油脂加工食品や粉末飲料、粉末スープなどの粉末食品などやカプセル状、タブレット状、粉末状、顆粒状などにした健康食品などを挙げることができる。
本発明のα−リポ酸含有水性組成物を含有する飲料としては、例えば、食塩などのミネラル、酸味料、甘味料、アルコール、ビタミン、フレーバーおよび果汁の中から少なくとも１種を含む飲料、例えばスポーツ飲料、果汁飲料、乳酸菌飲料、アルコール飲料、ビタミン・ミネラル飲料などが挙げられる。さらに、加工乳、豆乳、体質改善のための飲料、生理効果を期待できる天然素材を組合わせた飲料などを挙げることができる。
清涼飲料の調製法の例としては、ベースとなる飲料の濃縮液に必要量のα−リポ酸含有水性組成物を添加し、撹拌混合した後、飲用水を用いて希釈する。更に、これに加熱殺菌処理を施したものをビンまたは缶等の包材に充填し、製品とすることができる。
Examples of the food and drink containing the α-lipoic acid-containing aqueous composition of the present invention include bread and confectionery such as bread, biscuits, candy and jelly, processed milk food such as yogurt and ham, miso, sauce and sauce. , Seasonings such as dressings, processed foods such as tofu and noodles, processed oils and fats such as margarine, fat spread, shortening, powdered foods such as powdered beverages, powdered soups, capsules, tablets, powders, granules, etc. And health foods made.
Examples of the beverage containing the α-lipoic acid-containing aqueous composition of the present invention include beverages containing at least one of minerals such as salt, acidulants, sweeteners, alcohols, vitamins, flavors and fruit juices, such as sports. Examples include beverages, fruit juice beverages, lactic acid bacteria beverages, alcoholic beverages, and vitamin / mineral beverages. Furthermore, processed milk, soy milk, beverages for improving constitution, beverages combining natural materials that can be expected to have physiological effects, and the like.
As an example of a method for preparing a soft drink, a necessary amount of an α-lipoic acid-containing aqueous composition is added to a concentrated beverage of a base beverage, mixed with stirring, and then diluted with drinking water. Further, a product obtained by subjecting it to heat sterilization can be filled into a packaging material such as a bottle or a can to obtain a product.
具体例を用いてさらに本発明を詳細に説明する。以下に本実験における測定方法、評価方法を示す。
Ａ．α−リポ酸含有水性組成物の状態の評価
（１）平均粒子径の測定方法
試料の平均粒子径は、α−リポ酸含有水性組成物を精製水にて１００〜３００倍に希釈した水溶液を調製し、サブミクロン粒度分布測定装置〔型式：Ｎ４ＳＤ ベックマン・コールター（株）製〕により分散粒子を測定した。
（２）状態
製造直後及び２５℃で１週間静置後の状態を肉眼で観察し、以下の基準で評価した。
◎：非常に優れている、○：優れている、△：クリーミングが若干発生する。×：オイルオフ、二層分離が生じる。
なお、非常に優れている（◎）と優れている（○）との相違は、クリーミングの発生がない水性組成物において、これを１００倍に希釈し、透過率が９０％以上のものを非常に優れている（◎）と評価した。
（３）臭い
製造直後及び２５℃で１週間静置後の臭いを以下の基準で評価した。
◎：臭わない、○：僅かに臭う、△：やや臭う。×：異臭がする。
The present invention will be further described in detail using specific examples. The measurement method and evaluation method in this experiment are shown below.
A. Evaluation of State of α-Lipoic Acid-Containing Aqueous Composition (1) Method for Measuring Average Particle Diameter The average particle diameter of the sample is an aqueous solution obtained by diluting the α-lipoic acid-containing aqueous composition 100 to 300 times with purified water. Then, the dispersed particles were measured with a submicron particle size distribution analyzer (model: N4SD, manufactured by Beckman Coulter, Inc.).
(2) State Immediately after production and after standing for 1 week at 25 ° C., the state was observed with the naked eye and evaluated according to the following criteria.
A: Excellent, B: Excellent, B: Some creaming occurs. X: Oil-off and two-layer separation occur.
The difference between excellent (優 れ) and excellent (○) is that an aqueous composition that does not generate creaming is diluted 100 times and has a transmittance of 90% or more. (◎).
(3) Odor Immediately after production and after standing at 25 ° C. for 1 week, the odor was evaluated according to the following criteria.
A: No smell, B: Slightly smell, B: Slightly smelled. X: There is a strange odor.
Ｂ．安定性試験
（１）耐熱性試験
耐熱性を粒径の変化、状態の変化より評価した。
精製水に試料を１重量％となるように添加し、湯煎にかけ液温が８５℃に到達した時点より３０分間放置した後、室温まで放冷して、粒径を測定した。また、状態の変化を観察した。
（粒径の変化）
◎：±５ｎｍ未満、○：±５ｎｍ以上〜±１０ｎｍ未満、△：±１０ｎｍ以上〜±２０ｎｍ未満、×：±２０ｎｍより大
（試験後の状態）
◎：非常に優れている、○：優れている、△：クリーミングが若干発生する。×：オイルオフ、二層分離が生じる。
なお、非常に優れている（◎）と優れている（○）との相違は、クリーミングの発生がない水性組成物において、これを１００倍に希釈し、透過率が９０％以上のものを非常に優れている（◎）と評価した。
B. Stability test (1) Heat resistance test Heat resistance was evaluated from changes in particle size and state.
A sample was added to purified water so as to be 1% by weight, and the sample was placed in a water bath and allowed to stand for 30 minutes from the time when the liquid temperature reached 85 ° C., then allowed to cool to room temperature, and the particle size was measured. Moreover, the change of the state was observed.
(Change in particle size)
A: Less than ± 5 nm, O: ± 5 nm or more to less than ± 10 nm, Δ: ± 10 nm or more to less than ± 20 nm, X: Greater than ± 20 nm (state after test)
A: Excellent, B: Excellent, B: Some creaming occurs. X: Oil-off and two-layer separation occur.
The difference between excellent (優 れ) and excellent (○) is that an aqueous composition that does not generate creaming is diluted 100 times and has a transmittance of 90% or more. (◎).
（２）耐酸・耐熱試験
クエン酸にてｐＨを３に調整した緩衝水に試料を１重量％となるように添加し、上記（１）の耐熱性試験と同様に実験を行い、評価した。
(2) Acid / heat resistance test A sample was added to buffered water whose pH was adjusted to 3 with citric acid so as to be 1% by weight, and an experiment was conducted and evaluated in the same manner as in the heat resistance test of (1) above.
（３）耐塩・耐熱性試験
食塩を５重量％含有する精製水に試料を１重量％となるように添加し、上記（１）の耐熱性試験と同様に実験を行い、評価した。
(3) Salt Resistance / Heat Resistance Test A sample was added to purified water containing 5% by weight of salt so as to be 1% by weight, and an experiment was conducted and evaluated in the same manner as in the heat resistance test of (1) above.
実施例１
Ｂ成分のデカグリセリンオレイン酸モノエステル（阪本薬品工業（株）製、商品名：ＳＹグリスターＭＯ−７５０、８８ｇ（２２重量部））さらに水（２８８ｇ（７２重量部））を量り取り、７５〜８０℃で加熱溶解し、水相部とした。
次に、Ａ成分のα−リポ酸（デグサテクスチュラントシステムズジャパン（株）製、商品名：ＡＬＩＰＵＲＥ、１２ｇ（３重量部））およびＣ成分のリゾレシチン（太陽化学（株）製、商品名：サンレシチンＷ−１、１２ｇ（３重量部））を量り取り、湯煎にて３０℃で緩やかに加熱しながら混合し、これを油相部とした。
水相部を４８〜５３℃に冷却後、上記で調製した油相部を添加し、スリーワンモーターで２０分間攪拌混合を行った。その後、前記液をマイクロフルイダイザー（みづほ工業(株)製、型式：Ｍ−１１０Ｅ／Ｈ）を用いて１４７ＭＰａ（１５００ｋｇ／ｃｍ２）の圧力で均質化する工程を行った。この組成物をさらに前記の高圧均質化機に同条件で再度通過させることにより、α−リポ酸含有水性組成物を製造した。このα−リポ酸含有水性組成物の平均粒径を測定したところ、１３９ｎｍの乳化液であった。
この水性組成物を用い、前記の試験方法により安定性試験を行った。組成および得た水性組成物の平均粒子径を表１に示す。さらにこの水性組成物を用いて、前記の耐熱性試験、耐酸・耐熱性試験および耐塩・耐熱性試験を行った結果を合わせて表１に示す。
Example 1
B component decaglycerin oleic acid monoester (manufactured by Sakamoto Pharmaceutical Co., Ltd., trade name: SY Glyster MO-750, 88 g (22 parts by weight)) and water (288 g (72 parts by weight)) were weighed, and 75- It melt | dissolved by heating at 80 degreeC and was set as the water phase part.
Next, α-lipoic acid of component A (Degustex Texturant Systems Japan Co., Ltd., trade name: ALIPURE, 12 g (3 parts by weight)) and C component lysolecithin (product of Taiyo Kagaku Co., Ltd., trade name: Sanlecithin W-1, 12 g (3 parts by weight)) was weighed and mixed while gently heating at 30 ° C. in a hot water bath, and this was used as the oil phase part.
After cooling the water phase part to 48-53 ° C., the oil phase part prepared above was added and stirred and mixed with a three-one motor for 20 minutes. Thereafter, the liquid was homogenized at a pressure of 147 MPa (1500 kg / cm 2 ) using a microfluidizer (manufactured by Mizuho Kogyo Co., Ltd., model: M-110E / H). The composition was further passed through the high-pressure homogenizer under the same conditions to produce an α-lipoic acid-containing aqueous composition. When the average particle diameter of this α-lipoic acid-containing aqueous composition was measured, it was a 139 nm emulsion.
Using this aqueous composition, a stability test was conducted by the test method described above. The composition and the average particle size of the aqueous composition obtained are shown in Table 1. Further, Table 1 shows the results of the heat resistance test, acid resistance / heat resistance test and salt resistance / heat resistance test performed using this aqueous composition.
実施例２〜７及び比較例１〜４
配合組成を表１に示すようにした以外は、実施例１と同様にして均質化した乳化液を得た。実施例１と同様に、結果を表１にそれぞれ示す。
なお、実験には、他の成分として、デカグリセリンカプリン酸モノエステル（阪本薬品工業（株）製、商品名：ＳＹグリスターＭＣＡ７５０）、ペンタグリセリンオレイン酸モノエステル（太陽化学（株）製、商品名：サンソフトＡ−１７１Ｅ）、α−トコフェロール（エーディーエムファーイースト（株）製 商品名：Ｅ５−８７）、アスタキサンチン（富山化学工業（株）会社、商品名：アスタリールオイル５０Ｆ）、ショ糖ステアリン酸エステル（第一化学工業（株）製、商品名：ＤＫエステルＳＳ）、中鎖脂肪酸トリグリセライド（日本油脂株（株）製、商品名：パナセート８１０）を使用した。
Examples 2-7 and Comparative Examples 1-4
A homogenized emulsion was obtained in the same manner as in Example 1 except that the formulation was as shown in Table 1. Similar to Example 1, the results are shown in Table 1, respectively.
In the experiment, as other components, decaglycerin capric acid monoester (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd., trade name: SY Glister MCA750), pentaglycerin oleic acid monoester (manufactured by Taiyo Kagaku Co., Ltd., trade name) : Sunsoft A-171E), α-tocopherol (manufactured by ADM Far East Co., Ltd., trade name: E5-87), Astaxanthin (Toyama Chemical Co., Ltd., trade name: Asteryl Oil 50F), sucrose stearin Acid ester (Daiichi Kagaku Kogyo Co., Ltd., trade name: DK Ester SS) and medium chain fatty acid triglyceride (Nippon Yushi Co., Ltd., trade name: Panacet 810) were used.
表１の結果より、本発明の実施例は、Ｂ成分としてデカグリセリンカプリン酸モノエステルを使用した場合（比較例１）、Ｃ成分の結晶化抑制剤を使用しない場合（比較例２〜４）に比べて、α−リポ酸含有水性組成物の乳化状態、耐熱性、耐酸性、耐塩性において優れていることがわかる。
実施例１、２と実施例３〜４を比較すると、実施例３〜４のＤ成分を含有するα−リポ酸含有水性組成物は乳化状態および臭いにおいて優れていることがわかる。また、実施例６、７のＥ成分を含有するα−リポ酸含有水性組成物は耐熱性、耐酸性において優れていることがわかる。
From the results of Table 1, in the examples of the present invention, when decaglycerin capric acid monoester is used as the B component (Comparative Example 1), the crystallization inhibitor of the C component is not used (Comparative Examples 2 to 4). It can be seen that the α-lipoic acid-containing aqueous composition is superior in the emulsified state, heat resistance, acid resistance, and salt resistance.
When Example 1, 2 and Example 3-4 are compared, it turns out that the alpha-lipoic acid containing aqueous composition containing D component of Examples 3-4 is excellent in an emulsified state and an odor. Moreover, it turns out that the alpha-lipoic acid containing aqueous composition containing E component of Example 6 and 7 is excellent in heat resistance and acid resistance.
実施例８
Ｂ成分のヘキサグリセリンミリスチン酸モノエステル（太陽化学(株)製、商品名：サンソフトＱ−１４Ｆ、１０ｇ（２．５重量部））、デカグリセリンミリスチン酸モノエステル（三菱化学フーズ(株)製、商品名：リョートーポリグリエステルＭ−１０Ｄ、１０ｇ（２．５重量部））、還元水あめ（東和化成工業(株)製、商品名：アマミール、２６０ｇ（６５重量部））、水（７２．４ｇ（１８．１重量部））を量り取り、７５〜８０℃で加熱溶解した。
次に、Ａ成分のα−リポ酸（デグサテクスチュラントシステムズジャパン(株)製、商品名：ＡＬＩＰＵＲＥ、１２ｇ（３重量部））、Ｃ成分のレシチン（ツルレシチン工業(株)製、商品名：ＳＬＰ−ＰＣ５５、１２ｇ（３重量部））、Ｅ成分のα−トコフェロール（エーディーエムファーイースト（株）製、商品名：Ｅ５−８７、１３．６ｇ（３．４重量部））、中鎖脂肪酸トリグリセリド（日本油脂（株）製、商品名：パナセート８１０、６ｇ（１．５重量％））を量り取り、湯煎にて３０℃で緩やかに加熱、分散し、これを油相部とした。
水相を４８〜５３℃に冷却後、上記で調製した油相部を添加し、スリーワンモーターで２０分間攪拌混合を行った。その後、前記液をマイクロフルイダイザー（みづほ工業(株)製、型式：Ｍ−１１０Ｅ／Ｈ）を用いて１４７ＭＰａ（１５００ｋｇ／ｃｍ２）の圧力で均質化する工程を行った。この組成物をさらに前記の高圧均質化機に同条件で再度通過させることにより、α−リポ酸含有水性組成物を製造した。このα−リポ酸含有水性組成物の平均粒径を測定したところ、１１０ｎｍの乳化液であった。
この水性組成物を用い、前記の試験方法により安定性試験を行った。組成および得た水性組成物の平均粒径を表２に示す。さらにこの水性組成物を用いて、前記の耐熱性試験、耐酸・耐熱性試験および耐塩・耐熱性試験を行った結果を合わせて表２に示す。
Example 8
B component hexaglycerin myristic acid monoester (manufactured by Taiyo Kagaku Co., Ltd., trade name: Sunsoft Q-14F, 10 g (2.5 parts by weight)), decaglycerin myristic acid monoester (manufactured by Mitsubishi Chemical Foods Co., Ltd.) , Trade name: Ryoto-polyglycerester M-10D, 10 g (2.5 parts by weight)), reduced water candy (manufactured by Towa Kasei Kogyo Co., Ltd., trade name: Amamiru, 260 g (65 parts by weight)), water (72. 4 g (18.1 parts by weight)) was weighed and dissolved by heating at 75 to 80 ° C.
Next, component A α-lipoic acid (Degustex Texturant Systems Japan Co., Ltd., trade name: ALIPURE, 12 g (3 parts by weight)), component C lecithin (manufactured by Tururecitin Industry Co., Ltd., trade name: SLP-PC55, 12 g (3 parts by weight)), α-tocopherol of E component (manufactured by ADM Far East Co., Ltd., trade name: E5-87, 13.6 g (3.4 parts by weight)), medium chain fatty acid Triglyceride (Nippon Yushi Co., Ltd., trade name: Panacet 810, 6 g (1.5% by weight)) was weighed and gently heated and dispersed at 30 ° C. in a hot water bath to obtain an oil phase part.
After cooling the aqueous phase to 48 to 53 ° C., the oil phase part prepared above was added, and the mixture was stirred and mixed with a three-one motor for 20 minutes. Thereafter, the liquid was homogenized at a pressure of 147 MPa (1500 kg / cm 2 ) using a microfluidizer (manufactured by Mizuho Kogyo Co., Ltd., model: M-110E / H). The composition was further passed through the high-pressure homogenizer under the same conditions to produce an α-lipoic acid-containing aqueous composition. When the average particle diameter of this α-lipoic acid-containing aqueous composition was measured, it was an emulsion of 110 nm.
Using this aqueous composition, a stability test was conducted by the test method described above. Table 2 shows the composition and the average particle size of the aqueous composition obtained. Further, Table 2 shows the results of the heat resistance test, acid / heat resistance test, and salt / heat resistance test performed on the aqueous composition.
実施例９〜１４
実施例９〜１４の配合組成を表２に示すようにした以外は、実施例８と同様にして均質化した乳化液を得た。結果を表２にそれぞれ示す。なお、実験には、実施例１〜７で使用した成分以外に、デカグリセリンラウリン酸モノエステル（理研ビタミン（株）製、商品名：ポエムＪ−００２１）、ショ糖オレイン酸エステル（三菱化学フーズ（株）製、商品名：リョートーシュガーエステルＯ−１７０）、プロピレングリコールオレイン酸エステル（理研ビタミン（株）製、商品名：リケマールＰＯ−１００Ｖ）を使用した。
Examples 9-14
A homogenized emulsion was obtained in the same manner as in Example 8 except that the formulation compositions of Examples 9 to 14 were as shown in Table 2. The results are shown in Table 2, respectively. For the experiment, in addition to the components used in Examples 1 to 7, decaglycerin lauric acid monoester (manufactured by Riken Vitamin Co., Ltd., trade name: Poem J-0021), sucrose oleate (Mitsubishi Chemical Foods) Product name, Ryoto Sugar Ester O-170), propylene glycol oleate (Riken Vitamin Co., Ltd., product name: Riquemar PO-100V) were used.
表２の結果より、本発明の範囲で各成分の構成成分を変更しても、良好なα−リポ酸含有水性組成物を得られることを確認できた。 From the results in Table 2, it was confirmed that even when the constituent components of the respective components were changed within the scope of the present invention, a good α-lipoic acid-containing aqueous composition could be obtained.
Claims (6)
Ａ：α−リポ酸、
Ｂ：平均重合度３〜１０のポリグリセリンと炭素数１２〜１８の脂肪酸からなるポリグリセリン脂肪酸エステル、
Ｃ：結晶化抑制剤 The following A component contains 0.0001-20 weight%, B component 0.0001-50 weight%, and 0.01-10 weight part C component with respect to 1 weight part of A component, and a continuous phase is An α-lipoic acid-containing aqueous composition which is water.
A: α-lipoic acid,
B: polyglycerin fatty acid ester comprising polyglycerin having an average degree of polymerization of 3 to 10 and fatty acid having 12 to 18 carbon atoms,
C: Crystallization inhibitor
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| EP1864578A1 (en) * | 2006-06-09 | 2007-12-12 | FUJIFILM Corporation | Carotenoid-containing emulsion composition, process for its production, and food and cosmetic product containing the same |
| EP1927287A1 (en) | 2006-12-01 | 2008-06-04 | FUJIFILM Corporation | Emulsion composition, and foods and cosmetics containing the emulsion composition |
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