JP2003261594A - Disodium 5'-xanthylate crystal - Google Patents

Disodium 5'-xanthylate crystal

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Publication number
JP2003261594A
JP2003261594A JP2002062178A JP2002062178A JP2003261594A JP 2003261594 A JP2003261594 A JP 2003261594A JP 2002062178 A JP2002062178 A JP 2002062178A JP 2002062178 A JP2002062178 A JP 2002062178A JP 2003261594 A JP2003261594 A JP 2003261594A
Authority
JP
Japan
Prior art keywords
xanthylic acid
crystals
disodium salt
crystal
xanthylate
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
Application number
JP2002062178A
Other languages
Japanese (ja)
Other versions
JP2003261594A5 (en
Inventor
Tsutomu Shimose
強 下瀬
Hideki Murata
英城 村田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KH Neochem Co Ltd
Original Assignee
Kyowa Hakko Kogyo Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kyowa Hakko Kogyo Co Ltd filed Critical Kyowa Hakko Kogyo Co Ltd
Priority to JP2002062178A priority Critical patent/JP2003261594A/en
Publication of JP2003261594A publication Critical patent/JP2003261594A/en
Publication of JP2003261594A5 publication Critical patent/JP2003261594A5/ja
Pending legal-status Critical Current

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Abstract

<P>PROBLEM TO BE SOLVED: To provide 5'-Xanthylic acid useful as a taste substance in the form of disodium 5'-Xanthylate crystal having excellent stability. <P>SOLUTION: The disodium 5'-Xanthylate crystal having low hygroscopicity and excellent stability, and a method for producing the same are provided. Disodium 5'-Xanthylate n hydrate [(n) is an integer or fraction of from 0 to below 7], especially, disodium 5'-Xanthylate hexahydrate crystal, disodium 5'-Xanthylate trihydrate crystal, and disodium 5'-Xanthylate nonhydrate crystal are provided. <P>COPYRIGHT: (C)2003,JPO

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【発明の属する技術分野】本発明は、呈味物質として有
用な5'−キサンチル酸・2ナトリウム塩の結晶に関す
る。
TECHNICAL FIELD The present invention relates to crystals of 5'-xanthylic acid disodium salt useful as a taste substance.

【0002】[0002]

【従来の技術】5'−キサンチル酸またはその塩は、呈
味物質として有用であり、その製造法として特公昭40
−24515号、特公昭45−11115号、特開平4
−262790号等に記載の発酵生産法が知られてい
る。公知の5'−キサンチル酸およびその塩、ならびに
市販の5'−キサンチル酸・2ナトリウム塩は、凍結乾
燥、溶媒沈殿等の操作により得られているため、非晶性
アモルファスである。これらの非晶性アモルファスは、
吸湿性、潮解性等があり、安定性に問題があることが知
られている。そのため、例えば保存、輸送、流通等にお
いて冷蔵もしくは冷凍するか、または包装する際に防湿
対策が必要であり、工業レベルでの大量供給には、常温
で保存可能な5'−キサンチル酸またはその塩の結晶が
求められる。
2. Description of the Related Art 5'-Xanthylic acid or a salt thereof is useful as a taste substance, and its production method is disclosed in Japanese Examined Patent Publication No.
No. 24515, Japanese Examined Patent Publication No. 45-11115, Japanese Patent Laid-Open No. Hei 4
Fermentation production methods described in, for example, No. -262790 are known. Known 5'-xanthylic acid and its salt, and commercially available 5'-xanthylic acid disodium salt are amorphous amorphous since they are obtained by operations such as lyophilization and solvent precipitation. These amorphous amorphous are
It has hygroscopicity and deliquescent, and is known to have a problem with stability. Therefore, for example, it is necessary to take moisture-proof measures when refrigerating or freezing during storage, transportation, distribution, etc., or when packaging, and for large-scale supply at an industrial level, 5'-xanthylic acid or a salt thereof that can be stored at room temperature is stored. Is required.

【0003】また、特公昭40−24515号および特
開平4−262790号に、それぞれ5'−キサンチル
酸結合蛋白結晶、ならびに5'−キサンチル酸・バリウ
ム塩および5'−キサンチル酸・2ナトリウム塩・7水
和物の結晶という記載がある。しかし、5'−キサンチ
ル酸・バリウム塩および5'−キサンチル酸・2ナトリ
ウム塩・7水和物の結晶について、取得法に関する詳細
な記載、明確な結晶性を証明する記載および保存等で問
題となる安定性に関する記載はない。
In Japanese Patent Publication No. 40-24515 and JP-A-4-262790, 5'-xanthylic acid-binding protein crystals, 5'-xanthylic acid-barium salt and 5'-xanthylic acid-disodium salt, respectively. There is a description of crystals of heptahydrate. However, regarding crystals of 5'-xanthylic acid-barium salt and 5'-xanthylic acid-disodium salt heptahydrate, there is a problem in detailed description regarding the acquisition method, description demonstrating clear crystallinity and storage. There is no description regarding stability.

【0004】[0004]

【発明が解決しようとする課題】本発明の目的は、呈味
物質として有用な5'−キサンチル酸を吸湿性が低く安
定性に優れた5'−キサンチル酸・2ナトリウム塩の結
晶として提供することにある。
The object of the present invention is to provide 5'-xanthylic acid, which is useful as a tastant, as crystals of 5'-xanthylic acid disodium salt having low hygroscopicity and excellent stability. Especially.

【0005】[0005]

【課題を解決するための手段】本発明は、5'−キサン
チル酸・2ナトリウム塩の結晶およびその製造法に関す
る。5'−キサンチル酸・2ナトリウム塩の結晶の中で
も、5'−キサンチル酸・2ナトリウム塩・n水和物
(式中、nは0以上7未満の整数または分数を表す)の
結晶が好ましく、さらには5'−キサンチル酸・2ナト
リウム塩・6水和物の結晶、5'−キサンチル酸・2ナ
トリウム塩・3水和物の結晶または5'−キサンチル酸
・2ナトリウム塩・無水和物の結晶が好ましい。
The present invention relates to crystals of 5'-xanthylic acid disodium salt and a process for producing the same. Among the crystals of 5'-xanthylic acid disodium salt, crystals of 5'-xanthylic acid disodium salt n hydrate (wherein n represents an integer of 0 or more and less than 7 or a fraction), Further, crystals of 5'-xanthylic acid disodium salt hexahydrate, crystals of 5'-xanthylic acid disodium salt trihydrate or crystals of 5'-xanthylic acid disodium salt anhydrate. Crystals are preferred.

【0006】[0006]

【発明の実施の形態】本発明において、5'−キサンチ
ル酸・2ナトリウム塩の結晶はどのような結晶でもよい
が、例えば、柱状、板状、針状等の結晶があげられ、と
りわけ柱状の結晶が好ましく、水和物、アセトン、メタ
ノールもしくはエタノール等の溶媒和物等も5'−キサ
ンチル酸・2ナトリウム塩の結晶に包含される。
BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, the crystals of 5'-xanthylic acid disodium salt may be any crystals, and examples thereof include columnar, plate-like, and needle-like crystals, and particularly columnar crystals. Crystals are preferable, and hydrates, solvates of acetone, methanol, ethanol and the like are also included in the crystals of 5'-xanthylic acid disodium salt.

【0007】次に、5'−キサンチル酸・2ナトリウム
塩の結晶の製造法について説明する。 製造法:5'−キサンチル酸・2ナトリウム塩の水溶液
を、例えば濃縮等により、100g/L〜600g/L
の濃度、好ましくは300g/L〜500g/Lの濃度
に調整する。この濃度を調整した水溶液に、必要に応じ
て例えば塩化ナトリウム、硫酸ナトリウム等の無機塩、
アセトン、メタノール、エタノール等の貧溶媒等を添加
し、種晶の存在下または非存在下、−20℃から40℃
の間の温度で、好ましくは0℃から40℃の間の温度
で、12時間〜72時間、静置または攪拌により晶析し
て、5'−キサンチル酸・2ナトリウム塩の結晶を析出
させる。このとき、必要に応じて晶析操作の前に、溶液
を40℃から100℃の間の温度で、好ましくは50℃
から70℃の間の温度で、1分間〜1時間、加熱攪拌し
てもよい。析出した5'−キサンチル酸・2ナトリウム
塩の結晶を濾過し、減圧下または通風下で取得した結晶
を乾燥することにより、5'−キサンチル酸・2ナトリ
ウム塩の結晶を得ることができる。
Next, a method for producing crystals of 5'-xanthylic acid disodium salt will be described. Production method: 100 g / L to 600 g / L of an aqueous solution of 5'-xanthylic acid disodium salt, for example, by concentration.
Is adjusted to a concentration of preferably 300 g / L to 500 g / L. An aqueous solution having this concentration adjusted, if necessary, for example, sodium chloride, an inorganic salt such as sodium sulfate,
Add a poor solvent such as acetone, methanol, or ethanol, and in the presence or absence of seed crystals, -20 ° C to 40 ° C.
At a temperature of between 0 ° C. and 40 ° C. for 12 hours to 72 hours to allow crystallization by standing or stirring to precipitate crystals of 5′-xanthylic acid disodium salt. At this time, if necessary, the solution may be heated to a temperature between 40 ° C. and 100 ° C., preferably 50 ° C., before the crystallization operation.
You may heat-stir at the temperature between 1 to 70 degreeC for 1 minute-1 hour. The precipitated crystals of 5'-xanthylic acid disodium salt are filtered, and the crystals obtained under reduced pressure or under ventilation are dried to obtain crystals of 5'-xanthylic acid disodium salt.

【0008】このとき、乾燥時間、乾燥方法、乾燥温度
等を変えることにより、異なる水和物数の5'−キサン
チル酸・2ナトリウム塩の結晶を得ることができる。例
えば常圧下、20℃から60℃の間の温度で通風乾燥す
ることにより、5'−キサンチル酸・2ナトリウム塩・
6水和物の結晶を得ることができ、例えば40℃から1
30℃の間の温度で、通風下もしくは静置で常圧下、乾
燥するか、または減圧乾燥することにより、5'−キサ
ンチル酸・2ナトリウム塩・無水和物の結晶を得ること
ができる。
At this time, crystals of 5'-xanthylic acid disodium salt having different numbers of hydrates can be obtained by changing the drying time, drying method, drying temperature and the like. For example, 5'-xanthylic acid / disodium salt /
Crystals of hexahydrate can be obtained, for example from 40 ° C to 1
The crystals of 5'-xanthylic acid / disodium salt / anhydrous salt can be obtained by drying under atmospheric pressure or at a temperature of 30 ° C under atmospheric pressure or by drying under reduced pressure.

【0009】また、さらに洗浄、乾燥、再結晶等の操作
を行うことにより、さらに精製することもできる。5'
−キサンチル酸・2ナトリウム塩の水溶液は、市販の
5'−キサンチル酸・2ナトリウム塩の非晶性アモルフ
ァスを水に溶解して調製してもよいが、例えば既知の方
法(例えば、特公昭40−24515号等)に準じて、
発酵法等により得られる5'−キサンチル酸の反応液、
培養液、または除菌液を精製した5'−キサンチル酸の
水溶液から調製することもできる。
Further, further purification can be carried out by further performing operations such as washing, drying and recrystallization. 5 '
An aqueous solution of -xanthylic acid disodium salt may be prepared by dissolving a commercially available amorphous amorphous 5'-xanthylic acid disodium salt in water. For example, a known method (for example, Japanese Patent Publication No. No. 24515, etc.)
A reaction solution of 5'-xanthylic acid obtained by a fermentation method,
It is also possible to prepare a culture solution or a sterilized solution from a purified 5'-xanthylic acid aqueous solution.

【0010】例えば、5'−キサンチル酸の水溶液を、
例えば水酸化ナトリウム、炭酸水素ナトリウム、炭酸ナ
トリウム、ナトリウムエトキシド、ナトリウムメトキシ
ド等のナトリウム含有塩基で、pH6.0〜7.0、好
ましくはpH6.3〜6.8に調整することにより、
5'−キサンチル酸・2ナトリウム塩の水溶液を得るこ
とができる。このとき、水溶液中に、例えばアセトン、
メタノール、エタノール等が含まれていてもよい。
For example, an aqueous solution of 5'-xanthylic acid is
For example, by adjusting the pH to 6.0 to 7.0, preferably pH 6.3 to 6.8 with a sodium-containing base such as sodium hydroxide, sodium hydrogen carbonate, sodium carbonate, sodium ethoxide, and sodium methoxide,
An aqueous solution of 5'-xanthylic acid disodium salt can be obtained. At this time, in the aqueous solution, for example, acetone,
Methanol, ethanol, etc. may be contained.

【0011】5'−キサンチル酸の水溶液を得るための
精製法としては、例えば膜処理、ゲル濾過処理、活性炭
処理、イオン交換樹脂処理、合成吸着樹脂処理、溶媒沈
殿等、好ましくは活性炭処理、イオン交換樹脂処理、合
成吸着樹脂処理、溶媒沈殿等、さらに好ましくはイオン
交換樹脂処理、合成吸着樹脂処理等があげられる。ま
た、上記製造法で得られる5'−キサンチル酸・2ナト
リウム塩の結晶には、異なった結晶形または異なった粒
度のものが存在する場合もあり、これらが単独でまたは
混合物として得られることもあるが、これらも本発明に
包含される。
As a purification method for obtaining an aqueous solution of 5'-xanthylic acid, for example, membrane treatment, gel filtration treatment, activated carbon treatment, ion exchange resin treatment, synthetic adsorption resin treatment, solvent precipitation, etc., preferably activated carbon treatment, ions Exchange resin treatment, synthetic adsorption resin treatment, solvent precipitation and the like, more preferably ion exchange resin treatment, synthetic adsorption resin treatment and the like. In addition, the crystals of 5'-xanthylic acid disodium salt obtained by the above production method may have different crystal forms or different particle sizes, and these may be obtained alone or as a mixture. However, these are also included in the present invention.

【0012】次に、本発明の5'−キサンチル酸・2ナ
トリウム塩の結晶の保存安定性について、試験例により
具体的に説明する。 試験例1:5'−キサンチル酸・2ナトリウム塩の結晶
と非晶性アモルファスの吸湿性の比較 実施例1で得られた6水和物である5'−キサンチル酸
・2ナトリウム塩の結晶と市販の非晶性アモルファスに
ついて、相対湿度86%、23℃で、重量変化を追跡
し、吸湿による水分増加率を求めた。その結果を第1表
に示す。
Next, the storage stability of crystals of the 5'-xanthylic acid disodium salt of the present invention will be specifically described with reference to test examples. Test Example 1: Comparison of 5'-xanthylic acid disodium salt crystals and amorphous amorphous hygroscopicity 5'-xanthylic acid disodium salt crystals which are the hexahydrate obtained in Example 1 With respect to the commercially available amorphous amorphous, the weight change was traced at a relative humidity of 86% and 23 ° C., and the moisture increase rate due to moisture absorption was obtained. The results are shown in Table 1.

【0013】[0013]

【表1】 [Table 1]

【0014】その結果、5'−キサンチル酸・2ナトリ
ウム塩・6水和物の結晶は、非晶性アモルファスと比較
して、吸湿性が極めて低いことが判明した。以下に、本
発明を実施例によりさらに具体的に説明するが、本発明
はこれらの実施例に何ら限定されるものではない。
As a result, it was found that the crystals of 5'-xanthylic acid disodium salt hexahydrate have extremely low hygroscopicity as compared with amorphous amorphous. Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited to these Examples.

【0015】[0015]

【実施例】実施例1:5'−キサンチル酸・2ナトリウ
ム塩・6水和物の結晶 市販の5'−キサンチル酸・2ナトリウム塩(ヤマサ醤
油)を水に溶解して、5'−キサンチル酸・2ナトリウ
ム塩の水溶液5mL(400g/L、pH6.5)を調
製した。この水溶液中に塩化ナトリウム添加して、飽和
状態にした。その後、この水溶液を60℃に加温して、
同温度で2分間保持した後、静置状態にて常温まで放冷
し、結晶を析出させた。さらに24時間静置した後、析
出した結晶を濾取した。この結晶を23℃で通風乾燥
し、5'−キサンチル酸・2ナトリウム塩・6水和物の
結晶0.6gを得た。
Example 1 Crystal of 5'-xanthylic acid disodium salt hexahydrate Commercially available 5'-xanthylic acid disodium salt (Yamasa soy sauce) was dissolved in water to prepare 5'-xanthyl salt. 5 mL (400 g / L, pH 6.5) of an aqueous solution of an acid disodium salt was prepared. Sodium chloride was added to this aqueous solution to make it saturated. Then, this aqueous solution is heated to 60 ° C.,
After holding at the same temperature for 2 minutes, it was left standing to cool to room temperature to precipitate crystals. After standing still for 24 hours, the precipitated crystals were collected by filtration. The crystals were blow-dried at 23 ° C. to obtain 0.6 g of 5′-xanthylic acid • disodium salt • hexahydrate crystals.

【0016】 ナトリウム含量:12.6%(原子吸光測定法) 水分含量:20.4%(カールフィッシャー法) 粉末X線回折[回折角(2θo)、( )内は相対強度比
(I/I0)を示す]:7.60 (16), 12.15 (18), 15.35
(19), 17.45 (14), 19.75 (39), 20.65 (12), 22.70 (1
7), 27.15 (18), 31.50 (100), 32.35 (14), 36.35 (1
2), 37.70 (13),45.25 (56), 47.85 (13), 56.30 (17)
Sodium content: 12.6% (atomic absorption measurement method) Moisture content: 20.4% (Karl Fischer method) Powder X-ray diffraction [diffraction angle (2θ o ), relative intensity ratio (I / I 0 )]: 7.60 (16), 12.15 (18), 15.35
(19), 17.45 (14), 19.75 (39), 20.65 (12), 22.70 (1
7), 27.15 (18), 31.50 (100), 32.35 (14), 36.35 (1
2), 37.70 (13), 45.25 (56), 47.85 (13), 56.30 (17)

【0017】実施例2:5'−キサンチル酸・2ナトリ
ウム塩・無水和物の結晶 実施例1で得られた5'−キサンチル酸・2ナトリウム
塩・6水和物の結晶を、105℃で15時間、常圧で乾
燥することにより5'−キサンチル酸・2ナトリウム塩
・無水和物の結晶を得た。 水分含量:0.1%(カールフィッシャー法)
Example 2: Crystal of 5'-xanthylic acid disodium salt anhydrate The crystal of 5'-xanthylic acid disodium salt hexahydrate obtained in Example 1 was stored at 105 ° C. The crystals of 5'-xanthylic acid / disodium salt / anhydrous were obtained by drying at atmospheric pressure for 15 hours. Water content: 0.1% (Karl Fischer method)

【0018】実施例3:5'−キサンチル酸・2ナトリ
ウム塩・6水和物の結晶 特公昭40−024515号に記載の方法に準じて、
5'−キサンチル酸の反応液を得た。この反応液を遠心
分離により除菌した後、ダイヤイオンPA−412(C
l型:三菱化学製)に吸着させ、塩酸で5'−キサンチ
ル酸を溶出させた。この溶出液をダイヤイオンSK−1
04(H型:三菱化学製)に吸着させ、水で5'−キサ
ンチル酸画分を分離した後、5'−キサンチル酸画分を
ピュロライトA−100(OH型:ピュロライト社製)
に吸着させ、水酸化ナトリウム水溶液で5'−キサンチ
ル酸を溶出した。得られた溶出液を水酸化ナトリウムで
pH6.5に調整し、減圧下で濃縮することにより5'
−キサンチル酸・2ナトリウム塩の水溶液(400g/
L、60mL)を得た。得られた5'−キサンチル酸・
2ナトリウム塩の水溶液に、実施例1で得られた6水和
物である5'−キサンチル酸・2ナトリウム塩・6水和
物の結晶を種晶として0.24g添加し、24時間攪拌
した。析出した結晶を濾取した後、実施例1と同様に通
風乾燥を行い、5'−キサンチル酸・2ナトリウム塩・
6水和物の結晶6gを得た。得られた結晶の物性は、実
施例1に示す結晶と同等のものであった。
Example 3: Crystals of 5'-xanthylic acid / disodium salt / hexahydrate According to the method described in JP-B-40024515.
A reaction solution of 5'-xanthylic acid was obtained. After sterilizing this reaction solution by centrifugation, Diaion PA-412 (C
l-type: manufactured by Mitsubishi Kagaku Co., Ltd.), and 5′-xanthylic acid was eluted with hydrochloric acid. This eluate is Diaion SK-1
04 (H type: manufactured by Mitsubishi Kagaku Co., Ltd.), the 5'-xanthylic acid fraction was separated with water, and then the 5'-xanthylic acid fraction was separated from Purolite A-100 (OH type: manufactured by Purolite).
And 5'-xanthylic acid was eluted with an aqueous sodium hydroxide solution. The obtained eluate was adjusted to pH 6.5 with sodium hydroxide and concentrated under reduced pressure to obtain 5 '.
-Aqueous solution of xanthylic acid disodium salt (400 g /
L, 60 mL) was obtained. The obtained 5'-xanthylic acid
To the aqueous solution of the disodium salt, 0.24 g of crystals of the hexahydrate of 5'-xanthylic acid / disodium salt / hexahydrate obtained in Example 1 was added as a seed crystal and stirred for 24 hours. . The precipitated crystals were collected by filtration, and then air-dried in the same manner as in Example 1 to give 5′-xanthylic acid · disodium salt ·
6 g of crystals of hexahydrate were obtained. The physical properties of the obtained crystal were similar to those of the crystal shown in Example 1.

【0019】[0019]

【発明の効果】本発明により、呈味物質として有用な
5'−キサンチル酸を、吸湿性が低く安定性に優れた5'
−キサンチル酸・2ナトリウム塩の結晶として提供する
ことができる。
INDUSTRIAL APPLICABILITY According to the present invention, 5'-xanthylic acid, which is useful as a tastant, has a low hygroscopic property and excellent stability.
-Can be provided as crystals of xanthylic acid disodium salt.

Claims (6)

【特許請求の範囲】[Claims] 【請求項1】 5'−キサンチル酸・2ナトリウム塩の
結晶。
1. Crystals of 5'-xanthylic acid disodium salt.
【請求項2】 5'−キサンチル酸・2ナトリウム塩の
結晶が5'−キサンチル酸・2ナトリウム塩・n水和物
(式中、nは0以上7未満の整数または分数を表す)で
ある請求項1記載の結晶。
2. Crystals of 5'-xanthylic acid disodium salt are 5'-xanthylic acid disodium salt n hydrate (wherein n represents an integer of 0 or more and less than 7 or a fraction). The crystal according to claim 1.
【請求項3】 nが6である請求項2記載の結晶。3. The crystal according to claim 2, wherein n is 6. 【請求項4】 nが3である請求項2記載の結晶。4. The crystal according to claim 2, wherein n is 3. 【請求項5】 nが0である請求項2記載の結晶。5. The crystal according to claim 2, wherein n is 0. 【請求項6】 5'−キサンチル酸・2ナトリウム塩の
水溶液を100g/L〜600g/Lの濃度に調整し、
晶析により5'−キサンチル酸・2ナトリウム塩の結晶
を析出させることを特徴とする請求項1記載の結晶の製
造法。
6. An aqueous solution of 5'-xanthylic acid disodium salt is adjusted to a concentration of 100 g / L to 600 g / L,
The method for producing crystals according to claim 1, wherein crystals of 5'-xanthylic acid disodium salt are precipitated by crystallization.
JP2002062178A 2002-03-07 2002-03-07 Disodium 5'-xanthylate crystal Pending JP2003261594A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3475409A (en) * 1966-07-14 1969-10-28 Asahi Chemical Ind Process for preparing ribonucleoside-5'-monophosphate
JPH03215494A (en) * 1989-09-04 1991-09-20 Ajinomoto Co Inc Production of 5'-guanylic acid disodium and 5'-inosinic acid disodium mixed crystal
JPH03223299A (en) * 1990-01-27 1991-10-02 Ajinomoto Co Inc Production of disodium 5'-guanylate. disodium 5'-inosinate mixed crystal
JPH04262790A (en) * 1991-02-19 1992-09-18 Kyowa Hakko Kogyo Co Ltd Production of 5'-xanthylic acid by fermentation
JPH06336488A (en) * 1993-05-27 1994-12-06 Ajinomoto Co Inc Method for selectively crystallizing 2 hydrate and 2.5 hydrate of guanosine monosodium salt

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3475409A (en) * 1966-07-14 1969-10-28 Asahi Chemical Ind Process for preparing ribonucleoside-5'-monophosphate
JPH03215494A (en) * 1989-09-04 1991-09-20 Ajinomoto Co Inc Production of 5'-guanylic acid disodium and 5'-inosinic acid disodium mixed crystal
JPH03223299A (en) * 1990-01-27 1991-10-02 Ajinomoto Co Inc Production of disodium 5'-guanylate. disodium 5'-inosinate mixed crystal
JPH04262790A (en) * 1991-02-19 1992-09-18 Kyowa Hakko Kogyo Co Ltd Production of 5'-xanthylic acid by fermentation
JPH06336488A (en) * 1993-05-27 1994-12-06 Ajinomoto Co Inc Method for selectively crystallizing 2 hydrate and 2.5 hydrate of guanosine monosodium salt

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