JP7734405B2 - Method for improving the stability of 3-(4-hydroxy-3-methoxyphenyl)propionic acid and stability improver - Google Patents
Method for improving the stability of 3-(4-hydroxy-3-methoxyphenyl)propionic acid and stability improverInfo
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Description
本発明は、３－（４－ヒドロキシ－３－メトキシフェニル）プロピオン酸の安定性向上方法及び安定性向上剤に関する。 The present invention relates to a method for improving the stability of 3-(4-hydroxy-3-methoxyphenyl)propionic acid and a stability improver.
下記構造式（１）で表される化合物の名称は、３－（４－ヒドロキシ－３－メトキシフェニル）プロピオン酸（英名：３－（４－Ｈｙｄｒｏｘｙ－３－ｍｅｔｈｏｘｙｐｈｅｎｙｌ）ｐｒｏｐｉｏｎｉｃ ａｃｉｄ）である。下記構造式（１）で表される化合物については、特定の成分を含有する培地にてある種の乳酸菌を培養すると、当該化合物が検出されることが知られている（例えば、特許文献１参照）。
前記構造式（１）で表される化合物は、ジペプチジルペプチダーゼＩＶ活性阻害剤などの有効成分であり、ジペプチジルペプチダーゼＩＶ活性阻害用飲食品などに配合できることが知られている非常に有用な成分である（例えば、特許文献２参照）。 The compound represented by structural formula (1) is an active ingredient in, for example, a dipeptidyl peptidase IV activity inhibitor, and is a highly useful ingredient known to be suitable for incorporation into foods and beverages for inhibiting dipeptidyl peptidase IV activity (see, for example, Patent Document 2).
上述したように、前記構造式（１）で表される化合物は非常に有用な成分であるものの、経時的な安定性や加熱処理に対する安定性が十分とはいえず、その安定性を向上することができる技術の速やかな開発が強く求められているのが現状である。 As mentioned above, the compound represented by structural formula (1) is an extremely useful component, but its stability over time and against heat treatment is insufficient, and there is currently a strong demand for the rapid development of technology that can improve its stability.
本発明は、前記従来における諸問題を解決し、以下の目的を達成することを課題とする。即ち、本発明は、構造式（１）で表される化合物の経時的な安定性や加熱処理に対する安定性を向上することができる、前記構造式（１）で表される化合物の安定性向上方法及び安定性向上剤を提供することを目的とする。 The present invention aims to solve the above-mentioned conventional problems and achieve the following objectives. That is, the present invention aims to provide a method for improving the stability of a compound represented by structural formula (1) and a stability improver that can improve the stability of the compound represented by structural formula (1) over time and against heat treatment.
前記課題を解決するために本発明者が鋭意検討を重ねた結果、下記構造式（１）で表される化合物と、下記構造式（Ａ）で表される化合物とを共存させると、下記構造式（１）で表される化合物の経時的な安定性、特に光照射下や高温下における経時的な安定性や、加熱処理に対する安定性を向上させることができることを知見し、本発明を完成した。
本発明は、本発明者らの前記知見に基づくものであり、前記課題を解決するための手段としては、以下の通りである。即ち、
＜１＞ 下記構造式（Ａ）で表される化合物を下記構造式（１）で表される化合物と共存させることを含むことを特徴とする下記構造式（１）で表される化合物の安定性向上方法である。
＜３＞ 飲食品に含まれる前記構造式（１）で表される化合物の安定性を向上する前記＜１＞から＜２＞のいずれかに記載の方法である。
＜４＞ 下記構造式（１）で表される化合物の安定性を向上するために用いられる安定性向上剤であって、
下記構造式（Ａ）で表される化合物を含むことを特徴とする安定性向上剤である。
＜６＞ 飲食品に含まれる前記構造式（１）で表される化合物の安定性を向上する前記＜４＞から＜５＞のいずれかに記載の安定性向上剤である。
The present invention is based on the above findings of the present inventors, and the means for solving the above problems are as follows:
<1> A method for improving the stability of a compound represented by the following structural formula (1), comprising causing a compound represented by the following structural formula (A) to coexist with a compound represented by the following structural formula (1):
<3> The method according to any one of <1> and <2>, which improves the stability of the compound represented by the structural formula (1) contained in a food or drink.
<4> A stability improver used to improve the stability of a compound represented by the following structural formula (1):
The stability improver is characterized by containing a compound represented by the following structural formula (A):
<6> The stability improver according to any one of <4> and <5>, which improves the stability of a compound represented by the structural formula (1) contained in a food or drink.
本発明によれば、従来における前記諸問題を解決し、前記目的を達成することができ、構造式（１）で表される化合物の経時的な安定性や加熱処理に対する安定性を向上することができる、前記構造式（１）で表される化合物の安定性向上方法及び安定性向上剤を提供することができる。 The present invention solves the above-mentioned problems of the prior art and achieves the above-mentioned objectives, thereby providing a method for improving the stability of a compound represented by structural formula (1) and a stability improver that can improve the stability of the compound represented by structural formula (1) over time and against heat treatment.
（構造式（１）で表される化合物の安定性向上方法）
本発明の構造式（１）で表される化合物の安定性向上方法（以下、「安定性向上方法」と称することがある。）は、共存工程を少なくとも含み、必要に応じて更にその他の工程を含む。
本明細書において、構造式（１）で表される化合物の安定性の向上とは、構造式（１）で表される化合物の含有量の経時的な低下を抑制したり、加熱処理による構造式（１）で表される化合物の含有量の低下を抑制したりすることをいう。
(Method for improving the stability of a compound represented by structural formula (1))
The method of the present invention for improving the stability of a compound represented by structural formula (1) (hereinafter, sometimes referred to as the "stability improvement method") includes at least a coexistence step, and may further include other steps as necessary.
In this specification, improving the stability of the compound represented by structural formula (1) means suppressing a decrease in the content of the compound represented by structural formula (1) over time or suppressing a decrease in the content of the compound represented by structural formula (1) due to heat treatment.
＜共存工程＞
前記共存工程は、構造式（Ａ）で表される化合物を構造式（１）で表される化合物と共存させる工程である。
前記共存工程では、前記構造式（Ａ）で表される化合物、及び前記構造式（１）で表される化合物以外のその他の成分が存在していてもよい。
<Coexistence process>
The coexistence step is a step of causing the compound represented by structural formula (A) to coexist with the compound represented by structural formula (1).
In the coexistence step, components other than the compound represented by the structural formula (A) and the compound represented by the structural formula (1) may be present.
－構造式（１）で表される化合物－
下記構造式（１）で表される化合物の名称は、３－（４－ヒドロキシ－３－メトキシフェニル）プロピオン酸（英名：３－（４－Ｈｙｄｒｏｘｙ－３－ｍｅｔｈｏｘｙｐｈｅｎｙｌ）ｐｒｏｐｉｏｎｉｃ ａｃｉｄ）である（以下、「ＨＭＰＡ」と称することがある。）。
The name of the compound represented by the following structural formula (1) is 3-(4-hydroxy-3-methoxyphenyl)propionic acid (hereinafter, sometimes referred to as "HMPA").
前記構造式（１）で表される化合物は、公知の化合物であり、市販品を使用してもよいし、公知の方法により製造したものを使用してもよい。 The compound represented by structural formula (1) is a known compound, and a commercially available product may be used, or one produced by a known method may be used.
－構造式（Ａ）で表される化合物－
前記構造式（Ａ）で表される化合物の名称は、４－ヒドロキシ－３－メトキシけい皮酸（英名：４－Ｈｙｄｒｏｘｙ－３－ｍｅｔｈｏｘｙｃｉｎｎａｍｉｃ ａｃｉｄ）である（以下、「ＨＭＣＡ」と称することがある。）。
The compound represented by the structural formula (A) is called 4-hydroxy-3-methoxycinnamic acid (hereinafter sometimes referred to as "HMCA").
前記構造式（Ａ）で表される化合物は、公知の化合物であり、市販品を使用してもよいし、公知の方法により製造したものを使用してもよい。 The compound represented by structural formula (A) is a known compound, and a commercially available product may be used, or one produced by a known method may be used.
前記構造式（Ａ）で表される化合物の使用量（共存させる量）としては、特に制限はなく、目的に応じて適宜選択することができるが、前記構造式（１）で表される化合物１質量部に対して、前記構造式（Ａ）で表される化合物を０．００１質量部以上用いることが好ましく、０．０１質量部以上用いることがより好ましい。前記好ましい範囲内であると、前記構造式（１）で表される化合物の経時的な安定性や加熱処理に対する安定性をより向上することができる点で、有利である。なお、前記構造式（Ａ）で表される化合物の使用量の上限値としては、本発明の効果を損なわない限り、特に制限はなく、目的に応じて適宜選択することができる。 The amount of the compound represented by structural formula (A) used (amount to be co-present) is not particularly limited and can be selected appropriately depending on the purpose. However, it is preferable to use 0.001 parts by mass or more of the compound represented by structural formula (A) per 1 part by mass of the compound represented by structural formula (1), and more preferably 0.01 parts by mass or more. Being within this preferred range is advantageous in that it can further improve the stability of the compound represented by structural formula (1) over time and its stability against heat treatment. There is no particular upper limit to the amount of the compound represented by structural formula (A) used, as long as it does not impair the effects of the present invention, and it can be selected appropriately depending on the purpose.
－その他の成分－
前記その他の成分としては、本発明の効果を損なわない限り、特に制限はなく、前記構造式（１）で表される化合物の用途などに応じて適宜選択することができ、例えば、賦形剤、防湿剤、防腐剤、強化剤、増粘剤、乳化剤、酸化防止剤、甘味料、酸味料、調味料、着色料、香料、美白剤、保湿剤、油性成分、紫外線吸収剤、界面活性剤、増粘剤、アルコール類、粉末成分、色剤、水性成分、水、皮膚栄養剤、飲食品に用いられる成分などが挙げられる。これらは、１種単独で使用してもよいし、２種以上を併用してもよい。
前記その他の成分の使用量としては、特に制限はなく、目的に応じて適宜選択することができる。
-Other ingredients-
The other components are not particularly limited as long as they do not impair the effects of the present invention, and can be appropriately selected depending on the application of the compound represented by structural formula (1), and examples thereof include excipients, moisture-proofing agents, preservatives, strengthening agents, thickeners, emulsifiers, antioxidants, sweeteners, acidulants, seasonings, coloring agents, fragrances, whitening agents, moisturizers, oily components, UV absorbers, surfactants, thickeners, alcohols, powder components, coloring agents, aqueous components, water, skin nutrients, components used in foods and beverages, etc. These may be used alone or in combination of two or more.
The amounts of the other components used are not particularly limited and can be appropriately selected depending on the purpose.
－共存－
前記共存の方法としては、特に制限はなく、目的に応じて適宜選択することができ、例えば、前記構造式（１）で表される化合物を含有する系に前記構造式（Ａ）で表される化合物を加える方法、前記構造式（Ａ）で表される化合物を含有する系に前記構造式（１）で表される化合物を加える方法、前記構造式（１）で表される化合物及び前記構造式（Ａ）で表される化合物を同一の系に同時に加える方法などが挙げられる。これらは、いずれかの方法を単独で使用してもよいし、２種以上の方法を組み合わせてもよい。
-Coexistence-
The coexistence method is not particularly limited and can be appropriately selected depending on the purpose, and examples thereof include a method of adding the compound represented by structural formula (A) to a system containing the compound represented by structural formula (1), a method of adding the compound represented by structural formula (1) to a system containing the compound represented by structural formula (A), a method of adding the compound represented by structural formula (1) and the compound represented by structural formula (A) to the same system simultaneously, etc. Any of these methods may be used alone, or two or more of them may be combined.
＜その他の工程＞
前記その他の工程としては、本発明の効果を損なわない限り、特に制限はなく、目的に応じて適宜選択することができる。
<Other processes>
The other steps are not particularly limited as long as they do not impair the effects of the present invention, and can be appropriately selected depending on the purpose.
＜態様＞
前記構造式（１）で表される化合物の態様としては、特に制限はなく、目的に応じて適宜選択することができ、例えば、飲食品に含まれる態様、ジペプチジルペプチダーゼＩＶ活性阻害剤などの各種の製剤に含まれる態様などが挙げられる。
また、前記構造式（１）で表される化合物を含有する含有物は、液体であってもよいし、固体であってもよいし、半固体であってもよい。
前記構造式（１）で表される化合物を含有する含有物における前記構造式（１）で表される化合物の含有量としては、特に制限はなく、目的に応じて適宜選択することができる。
<Aspects>
The form of the compound represented by the structural formula (1) is not particularly limited and can be appropriately selected depending on the purpose. Examples include forms in which the compound is contained in foods and beverages, and forms in which the compound is contained in various preparations such as dipeptidyl peptidase IV activity inhibitors.
The content containing the compound represented by the structural formula (1) may be liquid, solid, or semi-solid.
The content of the compound represented by the structural formula (1) in the inclusion containing the compound represented by the structural formula (1) is not particularly limited and can be appropriately selected depending on the purpose.
前記飲食品としては、特に制限はなく、目的に応じて適宜選択することができ、例えば、茶飲料、清涼飲料、炭酸飲料、栄養飲料、果実飲料、乳酸飲料等の飲料；アイスクリーム、アイスシャーベット、かき氷等の冷菓；そば、うどん、はるさめ、ぎょうざの皮、しゅうまいの皮、中華麺、即席麺等の麺類；飴、キャンディー、ガム、チョコレート、錠菓、スナック菓子、ビスケット、ゼリー、ジャム、クリーム、焼き菓子、パン等の菓子類；カニ、サケ、アサリ、マグロ、イワシ、エビ、カツオ、サバ、クジラ、カキ、サンマ、イカ、アカガイ、ホタテ、アワビ、ウニ、イクラ、トコブシ等の水産物；かまぼこ、ハム、ソーセージ等の水産・畜産加工食品；加工乳、発酵乳等の乳製品；サラダ油、てんぷら油、マーガリン、マヨネーズ、ショートニング、ホイップクリーム、ドレッシング等の油脂及び油脂加工食品；ソース、たれ等の調味料；カレー、シチュー、親子丼、お粥、雑炊、中華丼、かつ丼、天丼、うな丼、ハヤシライス、おでん、マーボドーフ、牛丼、ミートソース、玉子スープ、オムライス、餃子、シューマイ、ハンバーグ、ミートボール等のレトルトパウチ食品サラダ、漬物等の惣菜；種々の形態の健康・美容・栄養補助食品；錠剤、顆粒剤、カプセル剤、ドリンク剤、トローチ等の医薬品、医薬部外品などが挙げられる。なお、前記飲食品は上記例示に限定されるものではない。 The food and drink products are not particularly limited and can be selected appropriately depending on the purpose. Examples include beverages such as tea drinks, soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks; frozen desserts such as ice cream, ice sherbet, and shaved ice; noodles such as soba, udon, harusame, gyoza wrappers, shumai wrappers, Chinese noodles, and instant noodles; sweets such as candy, candy, gum, chocolate, candy tablets, snacks, biscuits, jelly, jam, cream, baked goods, and bread; seafood such as crab, salmon, clams, tuna, sardines, shrimp, bonito, mackerel, whale, oysters, saury, squid, ark shells, scallops, abalone, sea urchin, salmon roe, and tokobushi; kamaboko, ham, Examples include processed seafood and livestock foods such as sausages; dairy products such as processed milk and fermented milk; oils and fats and processed oil foods such as salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, and dressings; condiments such as sauces and dressings; retort pouch foods such as curry, stew, oyakodon (chicken and egg rice bowl), porridge, rice porridge, Chinese rice bowl, katsudon (pork cutlet rice bowl), tempura bowl, eel bowl, hayashi rice, oden, mapo dolphin, beef bowl, meat sauce, egg soup, omelet rice, gyoza (dumplings), shumai (steamed dumplings), hamburger steak, and meatballs; side dishes such as salads and pickles; health, beauty, and nutritional supplements in various forms; pharmaceuticals and quasi-drugs such as tablets, granules, capsules, drinks, and lozenges. The foods and beverages are not limited to those listed above.
前記製剤の剤型としては、特に制限はなく、目的に応じて適宜選択することができ、例えば、錠剤、粉剤、カプセル剤、顆粒剤、エキス剤、シロップ剤等の経口投与剤；注射剤、点滴剤、坐剤等の非経口投与剤；化粧水、乳液、クリーム、軟膏、美容液、ローション、パック、ゼリー、リップクリーム、口紅、ファンデーション、入浴剤、石鹸、ボディーソープ、アストリンゼント、ヘアトニック、ヘアローション、ヘアクリーム、ヘアリキッド、ポマード、シャンプー、リンス、コンディショナー等の外用剤などが挙げられる。 The dosage form of the preparation is not particularly limited and can be selected appropriately depending on the purpose. Examples include oral administration preparations such as tablets, powders, capsules, granules, extracts, and syrups; parenteral administration preparations such as injections, drip infusions, and suppositories; and topical preparations such as lotions, emulsions, creams, ointments, serums, lotions, packs, jellies, lip balms, lipsticks, foundations, bath additives, soaps, body washes, astringents, hair tonics, hair lotions, hair creams, hair liquids, pomades, shampoos, rinses, and conditioners.
本発明の安定性向上方法によれば、構造式（１）で表される化合物の経時的な安定性、特に光照射下や高温下における経時的な安定性や、加熱処理に対する安定性を向上させることができる。 The stability improvement method of the present invention can improve the stability of the compound represented by structural formula (1) over time, particularly its stability over time under light irradiation or high temperatures, and its stability against heat treatment.
（構造式（１）で表される化合物の安定性向上剤）
本発明の構造式（１）で表される化合物の安定性向上剤（以下、「安定性向上剤」と称することがある。）は、構造式（１）で表される化合物の安定性を向上するために用いられる安定性向上剤であって、構造式（Ａ）で表される化合物を少なくとも含み、必要に応じて更にその他の成分を含む。
(Stability improver for compounds represented by structural formula (1))
The stability improver for the compound represented by structural formula (1) of the present invention (hereinafter, may be referred to as "stability improver") is a stability improver used to improve the stability of the compound represented by structural formula (1), and contains at least a compound represented by structural formula (A) and, if necessary, further contains other components.
＜構造式（Ａ）で表される化合物＞
前記構造式（Ａ）で表される化合物は、上記した本発明の安定性向上方法における構造式（Ａ）で表される化合物と同様である。
<Compound represented by structural formula (A)>
The compound represented by the structural formula (A) is the same as the compound represented by the structural formula (A) in the stability improving method of the present invention described above.
前記構造式（Ａ）で表される化合物の前記安定性向上剤における含有量としては、特に制限はなく、その使用量などに応じて適宜選択することができる。前記安定性向上剤は、前記構造式（Ａ）で表される化合物のみからなるものであってもよい。 The content of the compound represented by structural formula (A) in the stability improver is not particularly limited and can be selected appropriately depending on the amount used, etc. The stability improver may consist solely of the compound represented by structural formula (A).
前記構造式（Ａ）で表される化合物の使用量としては、特に制限はなく、目的に応じて適宜選択することができるが、前記構造式（１）で表される化合物１質量部に対して、前記構造式（Ａ）で表される化合物を０．００１質量部以上用いることが好ましく、０．０１質量部以上用いることがより好ましい。前記好ましい範囲内であると、前記構造式（１）で表される化合物の経時的な安定性や加熱処理に対する安定性をより向上することができる点で、有利である。なお、前記構造式（Ａ）で表される化合物の使用量の上限値としては、本発明の効果を損なわない限り、特に制限はなく、目的に応じて適宜選択することができる。 The amount of the compound represented by structural formula (A) used is not particularly limited and can be selected appropriately depending on the purpose. However, it is preferable to use 0.001 parts by mass or more of the compound represented by structural formula (A) per 1 part by mass of the compound represented by structural formula (1), and more preferably 0.01 parts by mass or more. Being within this preferred range is advantageous in that it can further improve the stability of the compound represented by structural formula (1) over time and its stability against heat treatment. There is no particular upper limit to the amount of the compound represented by structural formula (A) used, as long as it does not impair the effects of the present invention, and it can be selected appropriately depending on the purpose.
＜その他の成分＞
前記その他の成分としては、本発明の効果を損なわない限り、特に制限はなく、目的に応じて適宜選択することができ、例えば、上記した本発明の安定性向上方法におけるその他の成分の項目に記載したものなどが挙げられる。
前記その他の成分の前記安定性向上剤における含有量としては、特に制限はなく、目的に応じて適宜選択することができる。
<Other ingredients>
The other components are not particularly limited as long as they do not impair the effects of the present invention, and can be selected appropriately depending on the purpose. Examples include those listed in the section on other components in the stability improvement method of the present invention described above.
The content of the other components in the stability improver is not particularly limited and can be appropriately selected depending on the purpose.
本発明の安定性向上剤によれば、構造式（１）で表される化合物の経時的な安定性、特に光照射下や高温下における経時的な安定性や、加熱処理に対する安定性を向上させることができる。 The stability improver of the present invention can improve the stability of the compound represented by structural formula (1) over time, particularly under light irradiation or high temperatures, and its stability against heat treatment.
前記構造式（１）で表される化合物は、上記した本発明の安定性向上方法における構造式（１）で表される化合物と同様である。また、前記構造式（１）で表される化合物の態様も上記した本発明の安定性向上方法における＜態様＞の項目に記載したものと同様である。 The compound represented by structural formula (1) is the same as the compound represented by structural formula (1) in the stability improvement method of the present invention described above. Furthermore, the aspects of the compound represented by structural formula (1) are also the same as those described in the <Aspects> section of the stability improvement method of the present invention described above.
以下、試験例を説明するが、本発明は、これらの試験例に何ら限定されるものではない。なお、以下の試験例では、ＨＭＰＡは東京化成工業株式会社製のものを用い、ＨＭＣＡ及びアスコルビン酸は富士フイルム和光純薬株式会社製のものを用いた。 Test examples are described below, but the present invention is not limited to these test examples. In the following test examples, HMPA manufactured by Tokyo Chemical Industry Co., Ltd. was used, and HMCA and ascorbic acid manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. were used.
（試験例１：光照射）
ＨＭＰＡ標準品及びＨＭＣＡ標準品を０．１ｍｇ／ｍＬとなるよう水に溶解させ、ＮａＯＨを添加し、ｐＨ３又はｐＨ６に調整した。また、アスコルビン酸を１０ｍｇ／ｍＬとなるよう水に溶解させ、ＮａＯＨを添加し、ｐＨ３又はｐＨ６に調整した。これらの液を用いて５００ｍＬに、ＨＭＰＡ、ＨＭＣＡ、及びアスコルビン酸が表１－１～１－４に記載の濃度となるよう希釈し、サンプルとした。
(Test Example 1: Light Irradiation)
HMPA standard and HMCA standard were dissolved in water to a concentration of 0.1 mg/mL, and NaOH was added to adjust the pH to 3 or 6. Ascorbic acid was also dissolved in water to a concentration of 10 mg/mL, and NaOH was added to adjust the pH to 3 or 6. These solutions were used to dilute the solution to 500 mL so that the concentrations of HMPA, HMCA, and ascorbic acid were as shown in Tables 1-1 to 1-4, and these were used as samples.
前記サンプルを光照射（１４，０００ｌｕｘ、２５℃）にて保管し、ＨＭＣＡ配合時のＨＭＰＡの安定性を確認した。ＨＭＰＡの安定性は、下記の高速液体クロマトグラフィー（ＨＰＬＣ）条件にて、保管前後のサンプルにおけるＨＭＰＡの量を測定し、ＨＭＰＡの残存率を算出し、確認した。結果を表１－１～１－４に示す。
＜ＨＰＬＣ条件＞
・ カラム ： Ｗａｋｏｓｉｌ－ＩＩ ５Ｃ１８ ＨＧ ４．６ｍｍ×２５０ｍｍ（富士フイルム和光純薬株式会社）
・ 移動相 ： 水（０．１％ＴＨＦ）：アセトニトリル＝８０：２０
・ 流速 ： １ｍＬ／分間
・ 温度 ： ４０℃
・ 注入量 ： １０μＬ
・ 波長 ： ２８０ｎｍ
・ オートサンプラー ： １５℃
The samples were stored under light irradiation (14,000 lux, 25°C) to confirm the stability of HMPA when HMCA was added. The stability of HMPA was confirmed by measuring the amount of HMPA in the samples before and after storage under the following high performance liquid chromatography (HPLC) conditions, and calculating the residual rate of HMPA. The results are shown in Tables 1-1 to 1-4.
<HPLC conditions>
Column: Wakosil-II 5C18 HG 4.6 mm x 250 mm (Fujifilm Wako Pure Chemical Industries, Ltd.)
Mobile phase: Water (0.1% THF):Acetonitrile = 80:20
Flow rate: 1 mL/min Temperature: 40°C
・Injection volume: 10μL
・Wavelength: 280nm
・Autosampler: 15℃
（試験例２：４０℃保管）
ＨＭＰＡ標準品及びＨＭＣＡ標準品を０．１ｍｇ／ｍＬとなるよう水に溶解させ、ＮａＯＨを添加し、ｐＨ３又はｐＨ６に調整した。この液を用いて５００ｍＬにＨＭＰＡ及びＨＭＣＡが表２－１～２－２に記載の濃度となるよう希釈し、サンプルとした。
前記サンプルを４０℃にて保管した以外は、試験例１と同様にして、ＨＭＣＡ配合時のＨＭＰＡの安定性を確認した。結果を表２－１～２－２に示す。
(Test Example 2: Storage at 40°C)
HMPA standard and HMCA standard were dissolved in water to a concentration of 0.1 mg/mL, and NaOH was added to adjust the pH to 3 or 6. This solution was used to dilute the HMPA and HMCA to 500 mL so that the concentrations shown in Tables 2-1 and 2-2 were obtained, and these were used as samples.
The stability of HMPA when blended with HMCA was confirmed in the same manner as in Test Example 1, except that the sample was stored at 40° C. The results are shown in Tables 2-1 and 2-2.
（試験例３：殺菌）
ＨＭＰＡ標準品、ＨＭＣＡ標準品、及びアスコルビン酸を１ｍｇ／ｍＬとなるよう水に溶解させ、ＮａＯＨを添加し、ｐＨ６に調整した。これらの液を用いて、ＨＭＰＡ、ＨＭＣＡ、及びアスコルビン酸が表３－１～３－２に記載の濃度となるように調整し、サンプルとした。
前記サンプルを９５℃、１時間にて加熱を行った。
前記加熱前後のＨＭＰＡの量を試験例１と同様にして測定し、ＨＭＰＡの安定性を確認した。結果を表３－１～３－２に示す。
(Test Example 3: Sterilization)
HMPA standard, HMCA standard, and ascorbic acid were dissolved in water to a concentration of 1 mg/mL, and NaOH was added to adjust the pH to 6. Using these solutions, HMPA, HMCA, and ascorbic acid were adjusted to the concentrations shown in Tables 3-1 and 3-2 to prepare samples.
The sample was heated at 95° C. for 1 hour.
The stability of HMPA was confirmed by measuring the amount of HMPA before and after the heating in the same manner as in Test Example 1. The results are shown in Tables 3-1 and 3-2.
以上より、ＨＭＰＡをＨＭＣＡと共存させることで、ＨＭＰＡの安定性が向上することが確認された。また、この安定性の向上効果は、ＨＭＰＡをアスコルビン酸と共存させた場合よりも優れていることも確認された。 From the above, it was confirmed that the stability of HMPA is improved by coexisting HMPA with HMCA. It was also confirmed that this stability improvement effect is superior to that achieved when HMPA is coexisted with ascorbic acid.
Claims (6)
下記構造式（Ａ）で表される化合物を含むことを特徴とする安定性向上剤。
A stability improver comprising a compound represented by the following structural formula (A):
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