JPWO2007032340A1 - α-Lipoic acid-containing composition - Google Patents

α-Lipoic acid-containing composition Download PDF

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JPWO2007032340A1
JPWO2007032340A1 JP2007535478A JP2007535478A JPWO2007032340A1 JP WO2007032340 A1 JPWO2007032340 A1 JP WO2007032340A1 JP 2007535478 A JP2007535478 A JP 2007535478A JP 2007535478 A JP2007535478 A JP 2007535478A JP WO2007032340 A1 JPWO2007032340 A1 JP WO2007032340A1
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lipoic acid
solid composition
acid
food
water
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JP5085329B2 (en
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酒井　康
康 酒井
綾子 室町
綾子 室町
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KYOUWA HAKKO BIO CO.,LTD
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A23L2/39—Dry compositions
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/58—Colouring agents
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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

Abstract

本発明の目的は、安定性の高いα−リポ酸を含有する固体組成物、飲食品、液状製剤およびこれらの製造方法を提供することにある。本発明は、α−リポ酸を溶解した油脂と水溶性高分子とを混合することを特徴とする、α−リポ酸を含有する固体組成物の製造、および該固体組成物を用いる飲食品または液状製剤の製造に関する。また、α−リポ酸を溶解した油脂と水溶性高分子とを混合し、必要に応じて乳化または乾燥することを特徴とする、α−リポ酸を含有する固体組成物の製造、および該固体組成物を用いる飲食品または液状製剤の製造に関する。The objective of this invention is providing the solid composition, food-drinks, liquid formulation, and these manufacturing methods containing alpha-lipoic acid with high stability. The present invention relates to the production of a solid composition containing α-lipoic acid, and a food or drink using the solid composition, wherein the oil and fat in which α-lipoic acid is dissolved and a water-soluble polymer are mixed. It relates to the production of liquid preparations. Also, the production of a solid composition containing α-lipoic acid, which comprises mixing an oil and fat in which α-lipoic acid is dissolved and a water-soluble polymer, and emulsifying or drying as necessary, and the solid The present invention relates to the production of a food or drink or a liquid preparation using the composition.

Description

本発明は、α−リポ酸を含有する固体組成物、飲食品、液状製剤およびこれらの製造方法に関する。   The present invention relates to a solid composition containing α-lipoic acid, a food or drink, a liquid preparation, and a method for producing them.

α−リポ酸は解糖系で生じたピルビン酸がアセチルＣｏＡに変換される反応などに補酵素として作用する重要な物質であり、各種疾患の治療に利用されている。また、α−リポ酸およびその還元物であるジヒドロリポ酸は、近年、健康食品の素材としても注目されている。
一般に、健康食品は、扱いやすい粉末や錠剤等、固体組成物の形態で供給されることが多いこと、また、固体組成物は液体組成物と比べて、運搬する際の負担が少ないというメリットがあることから、α−リポ酸も固体組成物として供給されることが望まれている。α-Lipoic acid is an important substance that acts as a coenzyme in a reaction in which pyruvic acid generated in a glycolysis is converted to acetyl CoA, and is used for treatment of various diseases. In addition, α-lipoic acid and its reduced product, dihydrolipoic acid, have recently attracted attention as materials for health foods.
In general, health foods are often supplied in the form of solid compositions such as easy-to-handle powders and tablets, and solid compositions have the advantage that they are less burdensome to transport than liquid compositions. Therefore, it is desired that α-lipoic acid is also supplied as a solid composition.

しかし、α−リポ酸を固体組成物に加工する際、また、供給された固体組成物を利用する際、該組成物が加熱や発熱等により高温条件下にさらされることがある。
α−リポ酸は、融点以上に加熱されると重合するという性質を有しているため、α−リポ酸を含有する組成物が高温条件下にさらされた場合、該組成物中のα−リポ酸の含有量が低下することがあるという問題がある。However, when α-lipoic acid is processed into a solid composition or when the supplied solid composition is used, the composition may be exposed to high-temperature conditions due to heating or heat generation.
Since α-lipoic acid has a property of polymerizing when heated above its melting point, when the composition containing α-lipoic acid is exposed to high temperature conditions, α-lipoic acid in the composition There exists a problem that content of lipoic acid may fall.

したがって、安定性の高いリポ酸を含有する固体組成物が望まれている。
なお、脂溶性物質を含有する固形製剤の製造方法として、脂溶性物質を水溶性高分子物質で乳化し、吸着剤を加えて乳化懸濁し、粉末化する方法（特許文献１参照）、油溶性物質および化工澱粉を水に加えて乳化し、乳化物を乾燥する方法（特許文献２参照）が知られているが、いずれも上記課題を解決するものではない。
特開２００３−３１３１４５号公報 特開平１１−１９３２２９号公報 Therefore, a solid composition containing highly stable lipoic acid is desired.
As a method for producing a solid preparation containing a fat-soluble substance, a method in which a fat-soluble substance is emulsified with a water-soluble polymer substance, an adsorbent is added and emulsified and suspended, and powdered (see Patent Document 1), oil-soluble A method of adding a substance and a modified starch to water to emulsify and drying the emulsion (see Patent Document 2) is known, but none of them solves the above problems.
JP 2003-313145 A JP 11-193229 A

本発明の目的は、安定性の高いα−リポ酸を含有する固体組成物、飲食品、液状製剤およびこれらの製造方法を提供することにある。   The objective of this invention is providing the solid composition, food-drinks, liquid formulation, and these manufacturing methods containing alpha-lipoic acid with high stability.

本発明は、以下の（１）〜（６）に関する。
（１） α−リポ酸を溶解した油脂と水溶性高分子とを混合することを特徴とする、α−リポ酸を含有する固体組成物の製造方法。
（２） 上記（１）の製造法により得られる固体組成物。
（３） α−リポ酸、油脂および水溶性高分子を含有する固体組成物。The present invention relates to the following (1) to (6).
(1) A method for producing a solid composition containing α-lipoic acid, comprising mixing an oil and fat in which α-lipoic acid is dissolved with a water-soluble polymer.
(2) A solid composition obtained by the production method of (1) above.
(3) A solid composition containing α-lipoic acid, fats and oils and a water-soluble polymer.

（４） α−リポ酸、油脂および水溶性高分子を含有する固形製剤。
（５） 上記（２）または（３）の固体組成物を用いることを特徴とする飲食品または液状製剤の製造法。
（６） 上記（５）の方法により得られる飲食品または液状製剤。(4) A solid preparation containing α-lipoic acid, fat and water-soluble polymer.
(5) A method for producing a food or drink or liquid preparation characterized by using the solid composition of (2) or (3) above.
(6) A food or drink or liquid preparation obtained by the method of (5) above.

本発明により、安定性の高いα−リポ酸を含有する固体組成物、飲食品、液状製剤およびこれらの製造方法を提供することができる。   According to the present invention, it is possible to provide a solid composition, food and drink, liquid preparation containing α-lipoic acid having high stability, and a method for producing them.

本発明のα−リポ酸を含有する固体組成物（以下、本発明の固体組成物という）は、α−リポ酸、油脂および水溶性高分子を含有する固体組成物であればいずれの組成物であってもよいが、水分含量は、通常20重量％以下、好ましくは10重量％以下の組成物である。
本発明の固体組成物は、α−リポ酸を溶解した油脂と、水溶性高分子とを混合し、必要に応じて乳化または乾燥させて得ることができる。The solid composition containing α-lipoic acid of the present invention (hereinafter referred to as the solid composition of the present invention) is any composition as long as it is a solid composition containing α-lipoic acid, fats and oils and a water-soluble polymer. However, the moisture content is usually 20% by weight or less, preferably 10% by weight or less.
The solid composition of the present invention can be obtained by mixing an oil and fat in which α-lipoic acid is dissolved and a water-soluble polymer, and emulsifying or drying as necessary.

α−リポ酸としては、チオクト酸（１，２−ジチオラン−３−ペンタノン酸；１，２−ジチオラン−３−吉草酸）またはその還元体であるジヒドロリポ酸（６，８−ジメルカプトオクタン酸）があげられる。また、これらの脂肪酸エステル等のアルキルエステル、アミド等であってもよく、さらにこれらのナトリウム、カリウム等の金属塩であってもよい。   As α-lipoic acid, thioctic acid (1,2-dithiolane-3-pentanoic acid; 1,2-dithiolane-3-valeric acid) or dihydrolipoic acid (6,8-dimercaptooctanoic acid) which is a reduced form thereof is used. Can be given. Further, alkyl esters such as these fatty acid esters, amides, and the like may be used, and metal salts such as sodium and potassium may also be used.

油脂としては、脂肪酸グリセライドが好ましく、脂肪酸部分の炭素数が6〜10個である中鎖脂肪酸トリグリセライドがさらに好ましい。中鎖脂肪酸トリグリセライドとしては、脂肪酸部分がカプリル酸（炭素数8）、またはカプリン酸（炭素数10）であるものが好ましい。また、これらの脂肪酸グリセライドを含有する植物油脂、動物油脂等を用いてもよい。植物油脂としては、例えばヤシ油、パーム核油、大豆油、落花生油、綿実油、ナタネ油、ピーナッツ油、オリーブ油等があげられる。動物油脂としては、肝油、牛脂、ラード等があげられる。   As fats and oils, fatty acid glycerides are preferable, and medium-chain fatty acid triglycerides having 6 to 10 carbon atoms in the fatty acid portion are more preferable. As the medium-chain fatty acid triglyceride, those in which the fatty acid portion is caprylic acid (carbon number 8) or capric acid (carbon number 10) are preferable. Moreover, you may use the vegetable fats and oils, animal fats, etc. containing these fatty acid glycerides. Examples of vegetable oils include coconut oil, palm kernel oil, soybean oil, peanut oil, cottonseed oil, rapeseed oil, peanut oil, olive oil and the like. Animal fats and oils include liver oil, beef tallow, lard and the like.

油脂に溶解させるα−リポ酸の量は、油脂100重量部に対して0.1〜20重量部が好ましく、1〜10重量部がさらに好ましい。
α−リポ酸を油脂に溶解させる前後において温度の限定は特にないが、α−リポ酸を油脂に溶解させるまでの操作は、60℃以下で行うことが好ましい。
水溶性高分子としては、アラビアゴム、化工澱粉、澱粉、デキストリン、ゼラチン、カゼイン、アルブミン、アルギン酸塩、ペクチン、グルテン、セルロース、カルボキシメチルセルロース、メチルセルロース、エチルセルロース、ヒドロキシエチルセルロース等のセルロース誘導体、ポリビニルアルコール、ポリアクリルアミド、ポリビニルピロリドン等があげられ、アラビアゴムまたは化工澱粉が好ましく用いられる。化工澱粉としては、コハク酸、酢酸、アジピン酸またはこれらのアルキルもしくはアルケニル誘導体等の有機酸、例えば、オクテニルコハク酸と澱粉とのエステル等があげられる。これらの水溶性高分子は単独で用いてもよいし、２種類以上を併用してもよい。The amount of α-lipoic acid dissolved in the oil / fat is preferably 0.1 to 20 parts by weight, more preferably 1 to 10 parts by weight per 100 parts by weight of the oil / fat.
Although there is no particular limitation on the temperature before and after dissolving α-lipoic acid in fats and oils, the operation until α-lipoic acid is dissolved in fats and oils is preferably performed at 60 ° C. or lower.
Water-soluble polymers include gum arabic, modified starch, starch, dextrin, gelatin, casein, albumin, alginate, pectin, gluten, cellulose, carboxymethylcellulose, methylcellulose, ethylcellulose, hydroxyethylcellulose and other cellulose derivatives, polyvinyl alcohol, poly Examples thereof include acrylamide and polyvinyl pyrrolidone, and gum arabic or modified starch is preferably used. Examples of the modified starch include organic acids such as succinic acid, acetic acid, adipic acid or their alkyl or alkenyl derivatives, for example, esters of octenyl succinic acid and starch. These water-soluble polymers may be used alone or in combination of two or more.

α−リポ酸を溶解した油脂と水溶性高分子とを混合する工程において、水溶性高分子はそのまま用いてもよいが、水、アルコール等の水性媒体に溶解したものを用いてもよい。アルコールとしては、飲食品等への利用という観点から、エタノールが好ましく用いられる。水溶性高分子の濃度としては、10〜99重量％であることが好ましく、20〜50重量%がさらに好ましい。   In the step of mixing the oil and fat in which α-lipoic acid is dissolved and the water-soluble polymer, the water-soluble polymer may be used as it is, or a solution dissolved in an aqueous medium such as water or alcohol may be used. As the alcohol, ethanol is preferably used from the viewpoint of use in foods and drinks. The concentration of the water-soluble polymer is preferably 10 to 99% by weight, more preferably 20 to 50% by weight.

α−リポ酸を溶解して得られた油脂と混合する水溶性高分子の量としては、α−リポ酸を溶解した油脂1重量部に対して水溶性高分子が1〜1000重量部となる量が好ましく、1〜100重量部となる量がより好ましく、1〜50重量部となる量がさらに好ましく、2〜10重量部となる量が特に好ましい。
α−リポ酸を溶解して得られた油脂と水溶性高分子とを混合する方法としては、例えば、水平円筒型、傾斜円筒型、Ｖ型、二重円錐型、正立方体方型等の回転混合機、リボン型、スクリュー型、回転円盤型、流動化型等の固定型混合機を用いる方法があげられる。The amount of the water-soluble polymer mixed with the fat and oil obtained by dissolving α-lipoic acid is 1 to 1000 parts by weight of the water-soluble polymer with respect to 1 part by weight of the fat and oil in which α-lipoic acid is dissolved. The amount is preferably 1 to 100 parts by weight, more preferably 1 to 50 parts by weight, and particularly preferably 2 to 10 parts by weight.
As a method of mixing the fats and oils obtained by dissolving α-lipoic acid and water-soluble polymer, for example, rotation of horizontal cylinder type, inclined cylinder type, V type, double cone type, regular cube type, etc. Examples include a method using a fixed mixer such as a mixer, a ribbon type, a screw type, a rotating disk type, and a fluidization type.

α−リポ酸を溶解して得られた油脂と水溶性高分子とを混合して得られた組成物を必要に応じて乳化する際の乳化方法としては、例えば、コロイドミル、高速攪拌乳化機、高圧ホモゲナイザー、超高圧ホモゲナイザー、超音波ホモゲナイザー等の装置を用いる方法があげられる。乳化を行う前に予備乳化を行ってもよい。なお、高圧ホモゲナイザーの操作圧力は、500〜700kg/cm2、超高圧ホモゲナイザーの操作圧力は、1000kg/cm2以上であることが好ましい。As an emulsification method when emulsifying a composition obtained by mixing oil and fat obtained by dissolving α-lipoic acid with a water-soluble polymer as necessary, for example, a colloid mill, a high-speed stirring emulsifier And a method using an apparatus such as a high-pressure homogenizer, an ultra-high pressure homogenizer, or an ultrasonic homogenizer. Pre-emulsification may be performed before emulsification. The operation pressure of the high pressure homogenizer are, 500~700kg / cm 2, the operating pressure of the ultrahigh pressure homogenizer is preferably 1000 kg / cm 2 or more.

α−リポ酸を溶解して得られた油脂と水溶性高分子とを混合し、必要に応じて乳化して得られた組成物の水分含量が20重量%を超える場合は、水分含量が上記の範囲内となるように乾燥させる。乾燥方法としては、噴霧乾燥、噴霧冷却乾燥、凍結乾燥等があげられるが、噴霧乾燥が好ましい。
上記で得られた組成物はそのまま本発明の固体組成物として用いてもよいが、さらに転動造粒、流動層造粒、押し出し造粒、圧縮造粒、解砕造粒、噴霧造粒などの方法で造粒して本発明の固体組成物としてもよい。When the water content of the composition obtained by mixing the fats and oils obtained by dissolving α-lipoic acid and the water-soluble polymer and emulsifying as necessary exceeds 20% by weight, the water content is as described above. Dry so that it is within the range. Examples of the drying method include spray drying, spray cooling drying, freeze drying and the like, and spray drying is preferable.
The composition obtained above may be used as it is as the solid composition of the present invention, but further includes rolling granulation, fluidized bed granulation, extrusion granulation, compression granulation, pulverization granulation, spray granulation, etc. It is good also as the solid composition of this invention by granulating by the method of this.

本発明の固体組成物には、塩化ナトリウム、塩化カリウム、塩化アンモニウム等の無機塩、フルクトース、ラクトース、シュクロース等の低分子糖類（単糖類、二糖類、オリゴ糖類等）、グルタミン酸ナトリウム、グリシン等のアミノ酸、イノシン酸ナトリウム、グアニル酸ナトリウム等の核酸、トコフェロール、塩酸システイン、Ｌ−アスコルビン酸ステアリン酸エステル等の抗酸化剤、醤油、味噌、エキス等の天然調味料が存在していてもよい。   The solid composition of the present invention includes inorganic salts such as sodium chloride, potassium chloride and ammonium chloride, low molecular sugars such as fructose, lactose and sucrose (monosaccharides, disaccharides and oligosaccharides), sodium glutamate, glycine and the like. Amino acids, nucleic acids such as sodium inosinate and sodium guanylate, antioxidants such as tocopherol, cysteine hydrochloride and L-ascorbic acid stearate, and natural seasonings such as soy sauce, miso and extract may be present.

本発明の固体組成物は、そのまま医薬品、食品または飼料として用いることができる。
また、本発明の固体組成物は、医薬品または食品分野で用いられる製剤用基剤とともに、錠剤、カプセル剤、座剤、丸剤、散剤、顆粒剤等の固形製剤として調製して用いてもよい。The solid composition of the present invention can be used as it is as a pharmaceutical, food or feed.
The solid composition of the present invention may be prepared and used as a solid preparation such as a tablet, capsule, suppository, pill, powder, granule, etc. together with a preparation base used in the pharmaceutical or food field. .

製剤用基剤としては、ラクトース、グルコース、シュクロース、マンニット等の賦形剤、澱粉、アルギン酸ナトリウム等の崩壊剤、ステアリン酸マグネシウム、タルク等の滑沢剤、ゼラチン等の結合剤等があげられる。また、固形製剤中には、脂肪酸エステル等の界面活性剤、グリセリン等の可塑剤、ｐ−ヒドロキシ安息香酸エステル類等の防腐剤、ｐＨ調整剤、香料、着色料等が含有されていてもよい。   Examples of the preparation base include excipients such as lactose, glucose, sucrose, and mannitol, disintegrants such as starch and sodium alginate, lubricants such as magnesium stearate and talc, and binders such as gelatin. It is done. The solid preparation may contain a surfactant such as a fatty acid ester, a plasticizer such as glycerin, a preservative such as p-hydroxybenzoic acid esters, a pH adjuster, a fragrance, a colorant, and the like. .

本発明の固体組成物は、水、エタノール、塩溶液等の水性媒体に溶解し、必要に応じて、シュクロース、ソルビトール、フルクトース等の糖類、ポリエチレングリコール、プロピレングリコールなどのグリコール類、ごま油、オリーブ油、大豆油等の油類、ｐ−ヒドロキシ安息香酸エステル類などの防腐剤、香料、着色料等を添加して、液剤、懸濁剤、乳剤、エリキシル剤、シロップ剤、注射剤等の液状製剤の製造に用いることができる。また、ここであげた成分以外の上記の製剤用基材を含有していてもよい。   The solid composition of the present invention is dissolved in an aqueous medium such as water, ethanol, or a salt solution, and if necessary, sugars such as sucrose, sorbitol, and fructose, glycols such as polyethylene glycol and propylene glycol, sesame oil, and olive oil. , Liquids such as liquids, suspensions, emulsions, elixirs, syrups, injections, etc. with addition of preservatives such as oils such as soybean oil, p-hydroxybenzoates, flavorings, coloring agents, etc. Can be used in the manufacture of Moreover, you may contain said base materials for formulations other than the component quoted here.

また、本発明の固体組成物は、飲食品素材に添加して飲食品の製造に用いてもよい。
飲食品としては、清涼飲料水、ジュース類、茶類、乳酸菌飲料、冷菓、乳、乳製品（バター、チーズ、ヨーグルト、加工乳、脱脂乳等）、畜肉、畜肉製品（ハム、ソーセージ、ハンバーグ等）、魚肉、魚肉製品（蒲鉾、竹輪、さつま揚げ、ソーセージ等）、卵、卵製品（だし巻き、卵豆腐等）、菓子類（クッキー、ゼリー、スナック菓子等）、パン類、麺類、漬物類、燻製品、干物、佃煮、塩蔵品、スープ類、調味料等があげられる。本発明の飲食品は、粉末食品、シート状食品、瓶詰め食品、缶詰食品、レトルト食品、カプセル食品、タブレット状食品、流動食品、ドリンク剤等の形態のものであってもよい。Moreover, you may add the solid composition of this invention to food-drinks raw material, and may use it for manufacture of food-drinks.
As food and drink, soft drinks, juices, teas, lactic acid bacteria beverages, frozen desserts, milk, dairy products (butter, cheese, yogurt, processed milk, skim milk, etc.), livestock meat, livestock meat products (ham, sausage, hamburger, etc.) ), Fish meat, fish products (boiled, bamboo rings, fried fish, sausages, etc.), eggs, egg products (dried rolls, egg tofu, etc.), confectionery (cookies, jelly, snacks, etc.), breads, noodles, pickles, smoked products Products, dried fish, boiled rice cakes, salted products, soups, seasonings and the like. The food and drink of the present invention may be in the form of powdered food, sheet-like food, bottled food, canned food, retort food, capsule food, tablet-like food, liquid food, drink and the like.

本発明の固体組成物、飲食品または液状製剤中のα−リポ酸の含有量に特に限定はないが、0.001〜5重量%、好ましくは0.01〜5重量%含有されていることが望ましい。
本発明の固体組成物、飲食品または液状製剤を、ヒトまたは非ヒト動物に医薬品、食品または飼料として投与する量または投与回数は、投与目的、投与形態、投与するヒトまたは非ヒト動物の年齢、体重、症状等により異なるが、α−リポ酸として、成人一人当り0.1〜500mg、好ましくは1〜100mgを一日一回ないし数回投与する。The content of α-lipoic acid in the solid composition, food / beverage product or liquid preparation of the present invention is not particularly limited, but it is desirably 0.001 to 5% by weight, preferably 0.01 to 5% by weight.
The amount or frequency of administration of the solid composition, food / beverage product or liquid preparation of the present invention as a pharmaceutical, food or feed to a human or non-human animal depends on the purpose of administration, the mode of administration, the age of the human or non-human animal to be administered, Although it varies depending on body weight, symptoms, etc., 0.1 to 500 mg, preferably 1 to 100 mg, is administered once a day or several times a day as α-lipoic acid.

本発明の実施例を以下に示す。   Examples of the present invention are shown below.

1gのα−リポ酸〔リポイック（リポ酸を98%含有）、コグニス社製〕と9gの中鎖脂肪酸トリグリセライド（アクターＭ−１、理研ビタミン社製）とを混ぜ、57℃で加熱して溶解させた後、40gの化工澱粉（Purity gum1773、ナショナル・スターチ・ケミカル社製)に添加し、フードプロセッサー（ナショナル社製）を用い、混合して粉末Ａを得た。
また、49gの化工澱粉（Purity gum1773、ナショナル・スターチ・ケミカル社製)に1gのリポイックを添加し、フードプロセッサー（ナショナル社製）を用いて混合し、粉末Ｂを得た。1 g of α-lipoic acid [Lipoic (98% lipoic acid), manufactured by Cognis Co., Ltd.) and 9 g of medium chain fatty acid triglyceride (Actor M-1, manufactured by Riken Vitamin Co., Ltd.) were mixed and dissolved by heating at 57 ° C. Then, it was added to 40 g of modified starch (Purity gum1773, manufactured by National Starch Chemical Co., Ltd.) and mixed using a food processor (manufactured by National Co., Ltd.) to obtain Powder A.
Further, 1 g of lipoic was added to 49 g of modified starch (Purity gum1773, manufactured by National Starch Chemical Co., Ltd.), and mixed using a food processor (manufactured by National Co., Ltd.) to obtain Powder B.

粉末Ａおよび粉末Ｂの水分含量を測定したところ、いずれも5重量%以下であった。粉末Ａおよび粉末Ｂ中のα−リポ酸の含有量は、高速液体クロマトグラフィー（以下、HPLCという）を用いて測定した。
また、リポイック、粉末Ａおよび粉末Ｂをアルミ包材に封入し、恒温乾燥機〔MOV-212F(U)、三洋電機社製〕中、60℃の条件下で5日間保存し、それぞれの粉末中のα−リポ酸の含有量を保存前の方法と同様の方法により定量した。When the moisture content of powder A and powder B was measured, both were 5% by weight or less. The content of α-lipoic acid in powder A and powder B was measured using high performance liquid chromatography (hereinafter referred to as HPLC).
In addition, lipoic, powder A and powder B are enclosed in an aluminum wrapping material and stored for 5 days at 60 ° C. in a thermostatic dryer (MOV-212F (U), manufactured by Sanyo Electric Co., Ltd.). The content of α-lipoic acid was quantified by the same method as that before storage.

保存前後の各粉末中のα−リポ酸の含有量からα−リポ酸の残存率を算出した。保存前後の各粉末中のα−リポ酸の含有量および保存後のα−リポ酸の残存率を第１表に示す。   The residual ratio of α-lipoic acid was calculated from the content of α-lipoic acid in each powder before and after storage. Table 1 shows the content of α-lipoic acid in each powder before and after storage and the residual ratio of α-lipoic acid after storage.

Figure 2007032340
Figure 2007032340

第１表から明らかなとおり、α−リポ酸を中鎖脂肪酸トリグリセライドに溶解し、化工澱粉と混合して得られた本発明の固体組成物である粉末Ａは、α−リポ酸の安定性の高い粉末であった。   As is apparent from Table 1, powder A, which is a solid composition of the present invention obtained by dissolving α-lipoic acid in medium-chain fatty acid triglyceride and mixing with modified starch, is stable in α-lipoic acid. It was a high powder.

6.3gのリポイックと55.2gの中鎖脂肪酸トリグリセライド（アクターＭ−１、理研ビタミン社製）とを混ぜ、55℃で加熱して溶解させた。
また、237gのアラビアガム（アラビックコールＳＳ、三栄薬品社製）を690mlの水に加えて60℃で加熱して溶解し、Ｔ．Ｋホモミキサー（特殊機化工業社製）で攪拌しながら、上記α−リポ酸の中鎖脂肪酸トリグリセライド溶液を添加し、60℃、6,000rpmで30分間乳化して予備乳化液を得た。6.3 g of lipoic and 55.2 g of medium chain fatty acid triglyceride (Actor M-1, manufactured by Riken Vitamin Co., Ltd.) were mixed and heated at 55 ° C. to dissolve.
In addition, 237 g of gum arabic (Arabic Coal SS, manufactured by Sanei Pharmaceutical Co., Ltd.) was added to 690 ml of water and dissolved by heating at 60 ° C. While stirring with a K homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.), the medium chain fatty acid triglyceride solution of α-lipoic acid was added and emulsified at 60 ° C. and 6,000 rpm for 30 minutes to obtain a preliminary emulsion.

得られた予備乳化液を高圧ホモゲナイザーを用いて、乳化圧力800kg／cm2で3回リサイクル処理して乳化液を得た。該乳化液を噴霧乾燥機（Ｌ−１２型、大川原加工機社製）を用いて噴霧乾燥して粉末Ｃ 210gを得た。
また、98gのデキストリン（パインデックス＃４、松谷化学社製）に2gのリポイックを加え、フードプロセッサー（ナショナル社製）を用いて混合し、粉末Ｄ 100gを得た。The obtained preliminary emulsified liquid was recycled three times at an emulsifying pressure of 800 kg / cm 2 using a high-pressure homogenizer to obtain an emulsified liquid. The emulsion was spray-dried using a spray dryer (L-12, manufactured by Okawara Koki Co., Ltd.) to obtain 210 g of powder C.
Further, 2 g of lipoic was added to 98 g of dextrin (paindex # 4, manufactured by Matsutani Chemical Co., Ltd.) and mixed using a food processor (manufactured by National Corporation) to obtain 100 g of powder D.

粉末Ｃおよび粉末Ｄの水分含量を測定したところ、いずれも5重量%以下であった。粉末Ｃおよび粉末Ｄ中のα−リポ酸の含有量は、HPLCを用いて測定した。 また、リポイック、粉末Ｃおよび粉末Ｄをアルミ包材に封入し、恒温乾燥機〔MOV-212F（Ｕ）、三洋電機社製〕中、60℃の条件下で5日間保存し、それぞれの粉末中のα−リポ酸の含有量を保存前の方法と同様の方法により定量した。   When the water content of powder C and powder D was measured, both were 5% by weight or less. The content of α-lipoic acid in powder C and powder D was measured using HPLC. In addition, lipoic powder, powder C and powder D are enclosed in an aluminum wrapping material and stored for 5 days at 60 ° C. in a constant temperature dryer (MOV-212F (U), manufactured by Sanyo Electric Co., Ltd.). The content of α-lipoic acid was quantified by the same method as that before storage.

保存前後の各粉末中のα−リポ酸の含有量からα−リポ酸の残存率を算出した。保存前後の各粉末中のα−リポ酸の含有量および保存後のα−リポ酸の残存率を第２表に示す。   The residual ratio of α-lipoic acid was calculated from the content of α-lipoic acid in each powder before and after storage. Table 2 shows the content of α-lipoic acid in each powder before and after storage and the residual ratio of α-lipoic acid after storage.

Figure 2007032340
Figure 2007032340

第２表から明らかなとおり、α−リポ酸を中鎖脂肪酸トリグリセライドに溶解し、アラビアガム溶液と混合、乳化し、乾燥して得られた本発明の固体組成物である粉末Ｃは、α−リポ酸の安定性の高い粉末であった。   As is apparent from Table 2, powder C, which is a solid composition of the present invention obtained by dissolving α-lipoic acid in medium-chain fatty acid triglyceride, mixing with emulsified gum arabic, and drying, is α- It was a powder with high stability of lipoic acid.

実施例２で調製した粉末Ｃ 2.5gを水100mlに分散し、クエン酸を用いてpH3.8に調整し、α−リポ酸を含有する飲料を製造した。得られた飲料を、湯浴中で90℃、15分間加熱した。加熱前後の飲料中のα−リポ酸の含有量を測定したところ、α−リポ酸は100％残存していた。
また、実施例２で調製した粉末Ｃ 2.5gを水100mlに分散し、クエン酸を用いてpH6.0に調整し、α−リポ酸を含有する飲料を製造した。得られた飲料をオートクレーブを用いて120℃で、20分間加熱した。加熱前後の飲料中のα−リポ酸の含有量を測定したところ、α−リポ酸は100％残存していた。2.5 g of powder C prepared in Example 2 was dispersed in 100 ml of water and adjusted to pH 3.8 using citric acid to produce a beverage containing α-lipoic acid. The obtained beverage was heated in a hot water bath at 90 ° C. for 15 minutes. When the content of α-lipoic acid in the beverage before and after heating was measured, 100% α-lipoic acid remained.
Further, 2.5 g of the powder C prepared in Example 2 was dispersed in 100 ml of water and adjusted to pH 6.0 with citric acid to produce a beverage containing α-lipoic acid. The obtained beverage was heated at 120 ° C. for 20 minutes using an autoclave. When the content of α-lipoic acid in the beverage before and after heating was measured, 100% α-lipoic acid remained.

このように、本発明の固体組成物である粉末Ｃを用いて得られた飲料は、安定性の高いα−リポ酸を含有する飲料であった。
なお、実施例２で調製した粉末Ｄを水に添加したところ、α−リポ酸が溶解せず、飲用に適する飲料を製造できなかった。Thus, the drink obtained using the powder C which is the solid composition of the present invention was a drink containing α-lipoic acid having high stability.
In addition, when the powder D prepared in Example 2 was added to water, α-lipoic acid was not dissolved, and a beverage suitable for drinking could not be produced.

90℃の水100ｍｌに、1ｇの実施例２で調製した粉末Ｃ、1gのオルニチン塩酸塩、1gの水溶性CoQ-10（協和発酵工業社製）、0.1gのＬ−カルニチン、3ｇのエリスリトール、0.5ｇのクエン酸、0.01ｇの甘味料（アスパルテーム、味の素社製）を添加し、攪拌後、クエン酸でpHを3.3に調整した後、0.1ｇの香料を添加し飲料を製造した。該飲料は、飲用に適した飲料であった。   In 100 ml of water at 90 ° C., 1 g of powder C prepared in Example 2, 1 g of ornithine hydrochloride, 1 g of water-soluble CoQ-10 (manufactured by Kyowa Hakko Kogyo Co., Ltd.), 0.1 g of L-carnitine, 3 g of erythritol, 0.5 g of citric acid and 0.01 g of sweetener (Aspartame, manufactured by Ajinomoto Co., Inc.) were added. After stirring, the pH was adjusted to 3.3 with citric acid, and 0.1 g of flavor was added to produce a beverage. The beverage was a beverage suitable for drinking.

1ｇの実施例２で調製した粉末Ｃ、20ｇのグラニュー糖、40ｇのコラーゲン、3ｇのクエン酸、22ｇのトレハロース（林原商事社製）、10ｇのアスコルビン酸、2ｇの乳酸カルシウム、1ｇの酸化マグネシウム、および1ｇのビタミンミックス（DN、BASFJapan）を混合して清涼飲料用粉末100gを製造する。得られた清涼飲料用粉末30gを100ｍｌの水に加えて、よくかき混ぜることにより、飲料を製造する。   1 g of powder C prepared in Example 2, 20 g of granulated sugar, 40 g of collagen, 3 g of citric acid, 22 g of trehalose (produced by Hayashibara Shoji Co., Ltd.), 10 g of ascorbic acid, 2 g of calcium lactate, 1 g of magnesium oxide, And 1 g of vitamin mix (DN, BASFJapan) are mixed to produce 100 g of soft drink powder. A beverage is produced by adding 30 g of the obtained soft drink powder to 100 ml of water and stirring well.

2ｇの実施例２で調製した粉末Ｃ、100ｇのマルチトール（食品用50メッシュ、東和化成社製）および2ｇの水溶性CoQ-10（協和発酵工業社製）を、プルラン（プルランPF-20、林原社製）の 5%水溶液をバインダーとして流動層造粒機（FL-MINI型、フロイント産業社製)を用いて造粒した。得られた造粒物93ｇに、0.1g のＬ−カルニチン、3gの酸味料（クエン酸、磐田化学）、1gの甘味料（アスパルテーム、味の素社製）および3gの香料（グレープフルーツ香料、三栄源ＦＦＩ社製）を添加、混合し、グレープフルーツ味の顆粒を製造した。   2 g of powder C prepared in Example 2, 100 g of maltitol (50 mesh for food, manufactured by Towa Kasei Co., Ltd.) and 2 g of water-soluble CoQ-10 (manufactured by Kyowa Hakko Kogyo Co., Ltd.) were combined with pullulan (pululan PF-20, Granulation was performed using a fluidized bed granulator (FL-MINI type, manufactured by Freund Sangyo Co., Ltd.) using a 5% aqueous solution of Hayashibara Co., Ltd. To 93 g of the obtained granulated product, 0.1 g of L-carnitine, 3 g of acidulant (citric acid, Iwata Chemical), 1 g of sweetener (Aspartame, manufactured by Ajinomoto Co., Inc.) and 3 g of flavor (grapefruit flavor, Saneigen FFI) Grapefruit-flavored granules were produced by adding and mixing.

実施例６で調製した顆粒50gに、0.5gの二酸化ケイ素（カープレックス、塩野義製薬社製）を混合し、単発式圧縮成形機（菊水竪型成形機6B-2M)を用いて直径8mm、240mg／錠の錠剤を得た。   50 g of the granules prepared in Example 6 were mixed with 0.5 g of silicon dioxide (Carplex, manufactured by Shionogi Seiyaku Co., Ltd.), and a diameter of 8 mm, using a single-shot compression molding machine (Kikusui Tsuji Molding Machine 6B-2M). 240 mg / tablet tablets were obtained.

本発明により、安定性の高いα−リポ酸を含有する固体組成物、飲食品、液状製剤およびこれらの製造方法を提供することができる。
According to the present invention, it is possible to provide a solid composition, food and drink, liquid preparation containing α-lipoic acid having high stability, and a method for producing them.

Claims (6)

α−リポ酸を溶解した油脂と水溶性高分子とを混合する工程を含むことを特徴とする、α−リポ酸を含有する固体組成物の製造方法。 The manufacturing method of the solid composition containing alpha lipoic acid characterized by including the process of mixing the fats and oils which melt | dissolved alpha lipoic acid, and a water-soluble polymer. 請求項１記載の方法により得られる固体組成物。 A solid composition obtained by the method according to claim 1. α−リポ酸、油脂および水溶性高分子を含有する固体組成物。 A solid composition containing α-lipoic acid, fats and oils and a water-soluble polymer. α−リポ酸、油脂および水溶性高分子を含有する固形製剤。 A solid preparation containing α-lipoic acid, fats and oils and a water-soluble polymer. 請求項２または３記載の固体組成物を用いることを特徴とする飲食品または液状製剤の製造法。 A method for producing a food or drink or liquid preparation, wherein the solid composition according to claim 2 or 3 is used. 請求項５記載の方法により得られる飲食品または液状製剤。 A food or drink or liquid preparation obtained by the method according to claim 5.
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JP5027375B2 (en) * 2002-02-20 2012-09-19 エーザイ・アール・アンド・ディー・マネジメント株式会社 Improved formulation
AU2003266287A1 (en) * 2002-08-23 2004-03-11 Dsm Ip Assets B.V. Novel nutraceutical compositions comprising biotin
CN1694695A (en) * 2002-11-07 2005-11-09 帝斯曼知识产权资产管理有限公司 Novel nutraceutical compositions comprising epigallocatechin gallate

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