JPH0447656B2 - - Google Patents
Info
- Publication number
- JPH0447656B2 JPH0447656B2 JP58188004A JP18800483A JPH0447656B2 JP H0447656 B2 JPH0447656 B2 JP H0447656B2 JP 58188004 A JP58188004 A JP 58188004A JP 18800483 A JP18800483 A JP 18800483A JP H0447656 B2 JPH0447656 B2 JP H0447656B2
- Authority
- JP
- Japan
- Prior art keywords
- pyruvate
- aqueous solution
- acid
- pyruvic acid
- hydrogen ion
- 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.)
- Expired - Lifetime
Links
- 229940076788 pyruvate Drugs 0.000 claims description 44
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 43
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 26
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 229940107700 pyruvic acid Drugs 0.000 claims description 13
- -1 alkali metal salt Chemical class 0.000 claims description 11
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 16
- 229940054269 sodium pyruvate Drugs 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- JKVUQLWTIZFTMF-UHFFFAOYSA-M potassium;2-oxopropanoate Chemical compound [K+].CC(=O)C([O-])=O JKVUQLWTIZFTMF-UHFFFAOYSA-M 0.000 description 2
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- HDDQRHGTFKLBCI-UHFFFAOYSA-L barium(2+);2-oxopropanoate Chemical compound [Ba+2].CC(=O)C([O-])=O.CC(=O)C([O-])=O HDDQRHGTFKLBCI-UHFFFAOYSA-L 0.000 description 1
- 229940018333 calcium pyruvate Drugs 0.000 description 1
- UZWMCCLZMHPPKW-UHFFFAOYSA-L calcium;2-oxopropanoate Chemical compound [Ca+2].CC(=O)C([O-])=O.CC(=O)C([O-])=O UZWMCCLZMHPPKW-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- DNGVGLGPVLVROB-UHFFFAOYSA-M cesium;2-oxopropanoate Chemical compound [Cs+].CC(=O)C([O-])=O DNGVGLGPVLVROB-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HUKIJZIDGFUNMG-UHFFFAOYSA-N dimethyl 4-oxocyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCC(=O)CC1C(=O)OC HUKIJZIDGFUNMG-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- OFJHGWPRBMPXCX-UHFFFAOYSA-M lithium;2-oxopropanoate Chemical compound [Li+].CC(=O)C([O-])=O OFJHGWPRBMPXCX-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YXAMJFINXWQMCB-UHFFFAOYSA-L strontium;2-oxopropanoate Chemical compound [Sr+2].CC(=O)C([O-])=O.CC(=O)C([O-])=O YXAMJFINXWQMCB-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明はピルビン酸のアルカリ金属塩またはア
ルカリ土類金属塩の水溶液の安定化方法に関す
る。
ピルビン酸およびこれより誘導されるピルビン
酸のアルカリ金属塩またはアルカリ土類金属塩
（以下の説明において、ピルビン酸のアルカリ金
属塩またはアルカリ土類金属塩を単にピルビン酸
塩と呼称することがある）は、生体内物質代謝経
路における重要な中間体であるばかりでなく、各
種有機合成反応における合成中間体として、また
酸素反応を用いてＬ−トリプトフアン、Ｌ−シス
テイン、Ｌ−チロシン、Ｌ−ドーパーなどのアミ
ノ酸を合成する際の原料として有用な化合物であ
る。
ピルビン酸塩は溶液状態では極めて不安定であ
り、このことがピルビン酸塩の保存を困難なもの
にしている。たとえば、30重量％のピルビン酸ナ
トリウム水溶液を窒素雰囲気下に25℃で放置保存
したときの１週間後および１ヶ月後のピルビン酸
塩の残存割合はそれぞれ約80％および約60％であ
る。ピルビン酸塩はこのように溶液状態での長期
安定性に乏しく、このため、従来ピルビン酸塩は
結晶化して保存されてきた。しかしピルビン酸塩
の結晶化のためには繁雑でコストの高くつく晶析
操作を必要とし、さらに使用に際して結晶化され
たピルビン酸塩を溶媒に溶解するという繁雑な操
作が必要となるので、ピルビン酸塩を結晶として
取り扱うことは工業的に不利である。
かかる状況下にあつて本発明者らはピルビン酸
塩水溶液の保存安定性に影響を及ぼす要因につい
て詳細に検討した結果、ピルビン酸塩水溶液の水
素イオン指数（PH）が重要な因子であることがわ
かつた。ピルビン酸塩の水溶液は通常アルカリ性
を示し、その水素イオン指数はピルビン酸塩水溶
液中のピルビン酸塩の濃度が増すにしたがつて高
くなる傾向を示した。本発明者らはこの新しい知
見に基づきピルビン酸塩の水溶液の保存方法につ
いて検討を加えた結果、上記ピルビン酸塩水溶液
の水素イオン指数をその値が３〜６の範囲になる
ように調整することにより該ピルビン酸塩水溶液
を長期に亘つて安定に保存しうることを見出し、
本発明を完成するに至つた。
本発明方法において重要なことは、ピルビン酸
塩の水溶液の水素イオン指数をその値が３〜６の
範囲になるように保持することである。ピルビン
酸塩水溶液の水素イオン指数の値が８を越える場
合にばピルビン酸塩の安定性が著しく低下する。
ピルビン酸塩水溶液の水素イオン指数を上記特定
の範囲に調整するには、該ピルビン酸塩水溶液に
ピルビン酸またはピルビン酸よりも弱い酸を添加
する方法を採用するのが好ましい。この目的に使
用しうるピルビン酸以外の酸の具体例としては、
炭酸、硫酸水素ナトリウム、リン酸２水素ナトリ
ウム、およびギ酸、酢酸、プロピオン酸などの低
級カルボン酸を挙げることができる。また前述の
酸の代りに水溶液中で容易に加水分解されて遊離
カルボン酸を与える上記カルボン酸のメチルまた
はエチルエステルなどの水溶性のエステルを使用
することもできる。これらの酸およびエステルの
うちでも酢酸およびピルビン酸が特に好ましい。
本発明方法におけるピルビン酸のアルカリ金属
塩またはアルカリ土類金属塩は具体的には、ピル
ビン酸リチウム、ピルビン酸ナトリウム、ピルビ
ン酸カリウム、ピルビン酸セシウム、ピルビン酸
カルシウム、ピルビン酸バリウム、ピルビン酸マ
グネシウム、ピルビン酸ストロンチウムなどであ
り、これらのうちでもピルビン酸ナトリウムおよ
びピルビン酸カリウムが一般によく用いられる。
これらのピルビン酸塩は、ピルビン酸をアルカリ
（土類）金属の水酸化物または酸化物、もしくは
炭酸塩と反応させることにより、あるいはピルビ
ン酸エステルをアルカリ（土類）金属の水酸化物
を用いてアルカリ条件下で加水分解することによ
り、容易に入手することができる。ピルビン酸塩
の水溶液をピルビン酸のアルカリ中和反応または
ピルビン酸エステルのアルカリ加水分解反応によ
つて得る場合には、反応を調節して反応系中にピ
ルビン酸を一部残留させることにより該ピルビン
酸塩水溶液の水素イオン指数の値を本発明に規定
した範囲内に調整することもできる。
本発明方法を実施するにあたり、ピルビン酸塩
水溶液中のピルビン酸塩濃度についてはこのもの
が飽和溶解以下であれば何ら特別な制限はない
が、ピルビン酸塩の保存に用いられるタンクの容
量、保存中のピルビン酸塩の析出防止などの観点
から通常30重量％程度の水溶液が用いられる。
ピルビン酸塩水溶液の水素イオン指数の値はPH
メータなどを用いて測定することにより求めるこ
とができる。
本発明方法に従えばピルビン酸塩水溶液の安定
性を著しく高めることができるが、ピルビン酸塩
水溶液を長期に亘つて保存するにはその温度を低
く保つのが望ましく、特に約40℃以下に保持する
のがよい。また保存中におけるピルビン酸塩の酸
化等の副反応を防止するため、ピルビン酸塩水溶
液を非酸素雰囲気下、たとえば窒素、アルゴン、
炭酸ガスなどの不活性ガス雰囲気下に保存するの
が好ましい。ピルビン酸塩は光に対しても敏感で
あるので、ピルビン酸塩水溶液は光を遮断して保
存すののがよい。
以下、実施例にて本発明方法を具体的に説明す
る。
実施例 １
あらかじめ窒素置換した100mlのメスフラスコ
にピルビン酸ナトリウムの結晶30ｇを入れ、窒素
置換済みの蒸溜水を添加し、ピルビン酸ナトリウ
ムを完全溶解することにより30重量％ピルビン酸
ナトリウム水溶液を調製した。その後この系に窒
素雰囲気下ピルビン酸0.24ｇ（存在するピルビン
酸ナトリウムの量の１モル％に相当）を添加し、
完全溶解した。溶解後の溶液のPHをPHメータを用
いて測定したところ4.59であつた。上記により調
製した溶液を25℃にて光を遮断して２ヶ月間にわ
たつて保存し、その安定性を液体クロマトグラフ
イーにより分析することにより調べた。その結
果、１ヶ月後および２ヶ月後のピルビン酸ナトリ
ウムの残存率は調製直後を基準としてそれぞれ
99.5％および99％であつた。
実施例２〜７および比較例１〜４
ピルビン酸塩の種類、ピルビン酸塩の濃度、添
加するカルボン酸およびカルボン酸エステルの種
類および量、保存温度を種々変化させ、保存期間
を30日とした以外は実施例１と同様の条件下でピ
ルビン酸塩水溶液の保存安定性を調べた。その結
果を表１にまとめて示す。
The present invention relates to a method for stabilizing an aqueous solution of an alkali metal or alkaline earth metal salt of pyruvic acid. Pyruvic acid and alkali metal salts or alkaline earth metal salts of pyruvic acid derived therefrom (in the following description, alkali metal salts or alkaline earth metal salts of pyruvic acid may be simply referred to as pyruvate) is not only an important intermediate in the metabolic pathway of living substances, but also a synthetic intermediate in various organic synthesis reactions, and is used to synthesize L-tryptophan, L-cysteine, L-tyrosine, L-doper, etc. using oxygen reactions. It is a compound useful as a raw material when synthesizing amino acids. Pyruvate is extremely unstable in solution, which makes storage of pyruvate difficult. For example, when a 30% by weight aqueous sodium pyruvate solution is stored at 25° C. under a nitrogen atmosphere, the residual percentage of pyruvate after one week and one month is about 80% and about 60%, respectively. Pyruvate thus has poor long-term stability in a solution state, and for this reason, pyruvate has conventionally been stored by crystallizing it. However, crystallization of pyruvate requires a complicated and costly crystallization operation, and furthermore, it requires a complicated operation of dissolving the crystallized pyruvate in a solvent. It is industrially disadvantageous to treat acid salts as crystals. Under these circumstances, the present inventors conducted a detailed study on the factors that affect the storage stability of pyruvate aqueous solutions, and as a result, they found that the hydrogen ion index (PH) of pyruvate aqueous solutions is an important factor. I understand. A pyruvate aqueous solution is usually alkaline, and its hydrogen ion index tends to increase as the concentration of pyruvate in the pyruvate aqueous solution increases. Based on this new knowledge, the present inventors investigated the storage method of pyruvate aqueous solution and found that the hydrogen ion index of the pyruvate aqueous solution was adjusted so that its value was in the range of 3 to 6. discovered that the pyruvate aqueous solution can be stored stably for a long period of time,
The present invention has now been completed. What is important in the method of the present invention is to maintain the hydrogen ion index of the aqueous solution of pyruvate within the range of 3-6. When the hydrogen ion index value of the pyruvate aqueous solution exceeds 8, the stability of pyruvate is significantly reduced.
In order to adjust the hydrogen ion index of the pyruvate aqueous solution to the above specific range, it is preferable to adopt a method of adding pyruvic acid or an acid weaker than pyruvic acid to the pyruvate aqueous solution. Specific examples of acids other than pyruvic acid that can be used for this purpose include:
Mention may be made of carbonic acid, sodium hydrogen sulfate, sodium dihydrogen phosphate, and lower carboxylic acids such as formic acid, acetic acid, and propionic acid. Also, in place of the above-mentioned acids, water-soluble esters such as methyl or ethyl esters of the above-mentioned carboxylic acids can be used, which are easily hydrolyzed in aqueous solution to give free carboxylic acids. Among these acids and esters, acetic acid and pyruvic acid are particularly preferred. Specifically, the alkali metal salt or alkaline earth metal salt of pyruvic acid in the method of the present invention includes lithium pyruvate, sodium pyruvate, potassium pyruvate, cesium pyruvate, calcium pyruvate, barium pyruvate, magnesium pyruvate, These include strontium pyruvate, and among these, sodium pyruvate and potassium pyruvate are commonly used.
These pyruvates are prepared by reacting pyruvate with an alkali (earth) metal hydroxide or oxide or carbonate, or by reacting pyruvate with an alkali (earth) metal hydroxide. It can be easily obtained by hydrolysis under alkaline conditions. When an aqueous solution of pyruvate is obtained by an alkali neutralization reaction of pyruvic acid or an alkaline hydrolysis reaction of a pyruvate ester, the pyruvic acid can be obtained by adjusting the reaction so that a portion of pyruvic acid remains in the reaction system. The hydrogen ion index value of the aqueous acid salt solution can also be adjusted within the range specified in the present invention. When carrying out the method of the present invention, there are no particular restrictions on the pyruvate concentration in the pyruvate aqueous solution as long as the concentration is below saturation dissolution, but the capacity of the tank used to store pyruvate, the storage An aqueous solution of about 30% by weight is usually used from the viewpoint of preventing precipitation of pyruvate therein. The hydrogen ion index value of pyruvate aqueous solution is PH
It can be determined by measuring with a meter or the like. According to the method of the present invention, the stability of the pyruvate aqueous solution can be significantly increased; however, in order to preserve the pyruvate aqueous solution for a long period of time, it is desirable to keep the temperature low, especially below about 40°C. It is better to do so. In addition, in order to prevent side reactions such as oxidation of pyruvate during storage, the pyruvate aqueous solution should be stored in a non-oxygen atmosphere such as nitrogen, argon, etc.
It is preferable to store it under an inert gas atmosphere such as carbon dioxide gas. Pyruvate is also sensitive to light, so it is best to store pyruvate aqueous solutions protected from light. Hereinafter, the method of the present invention will be specifically explained in Examples. Example 1 30 g of sodium pyruvate crystals were placed in a 100 ml volumetric flask that had been purged with nitrogen in advance, and distilled water that had been purged with nitrogen was added to completely dissolve the sodium pyruvate, thereby preparing a 30% by weight aqueous sodium pyruvate solution. . 0.24 g of pyruvate (corresponding to 1 mol% of the amount of sodium pyruvate present) was then added to this system under a nitrogen atmosphere,
Completely dissolved. The pH of the solution after dissolution was measured using a PH meter and found to be 4.59. The solution prepared above was stored at 25° C. in the dark for two months, and its stability was analyzed by liquid chromatography. As a result, the residual rate of sodium pyruvate after 1 month and 2 months was determined based on the value immediately after preparation.
They were 99.5% and 99%. Examples 2 to 7 and Comparative Examples 1 to 4 The type of pyruvate, the concentration of pyruvate, the type and amount of carboxylic acid and carboxylic acid ester to be added, and the storage temperature were varied, and the storage period was 30 days. The storage stability of the pyruvate aqueous solution was examined under the same conditions as in Example 1 except for this. The results are summarized in Table 1.
【表】
実施例８〜10および比較例５〜７
ピルビン酸塩の種類、ピルビン酸塩の濃度、添
加するカルボン酸およびカルボン酸エステルの種
類および量、保存温度を種々変化させ、保存期間
を30日とした以外は実施例１と同様の条件下でピ
ルビン酸塩水溶液の保存安定性を調べた。その結
果を表２にまとめて示す。[Table] Examples 8 to 10 and Comparative Examples 5 to 7 The type of pyruvate, the concentration of pyruvate, the type and amount of carboxylic acid and carboxylic acid ester to be added, and the storage temperature were varied, and the storage period was 30 days. The storage stability of the pyruvate aqueous solution was investigated under the same conditions as in Example 1, except that the storage stability was set at 100 days. The results are summarized in Table 2.
Claims (1)
土類金属塩の水溶液の水素イオン指数（pH）を
その値が３〜６の範囲になるように調整すること
を特徴とするピルビン酸塩水溶液の安定化方法。1. A method for stabilizing an aqueous solution of pyruvate, which comprises adjusting the hydrogen ion index (pH) of an aqueous solution of an alkali metal salt or alkaline earth metal salt of pyruvic acid so that the value falls within the range of 3 to 6. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18800483A JPS6078936A (en) | 1983-10-06 | 1983-10-06 | Stabilization of aqueous solution of pyruvic acid salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18800483A JPS6078936A (en) | 1983-10-06 | 1983-10-06 | Stabilization of aqueous solution of pyruvic acid salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6078936A JPS6078936A (en) | 1985-05-04 |
| JPH0447656B2 true JPH0447656B2 (en) | 1992-08-04 |
Family
ID=16215954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18800483A Granted JPS6078936A (en) | 1983-10-06 | 1983-10-06 | Stabilization of aqueous solution of pyruvic acid salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6078936A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008046357A1 (en) * | 2006-10-18 | 2008-04-24 | Fangqiang Zhou | Aqueous solution containing sodium pyruvate, preparation method and use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4775785B2 (en) * | 2004-05-28 | 2011-09-21 | 東レ・ファインケミカル株式会社 | Method for producing high purity 2-keto acid ester |
-
1983
- 1983-10-06 JP JP18800483A patent/JPS6078936A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008046357A1 (en) * | 2006-10-18 | 2008-04-24 | Fangqiang Zhou | Aqueous solution containing sodium pyruvate, preparation method and use thereof |
| US8835508B2 (en) | 2006-10-18 | 2014-09-16 | Fangqiang Zhou | Stable aqueous solution containing sodium pyruvate, and the preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6078936A (en) | 1985-05-04 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |