JPS6263859A - Automatic analyzer for homovanillic acid and vanilamandelic acid - Google Patents
Automatic analyzer for homovanillic acid and vanilamandelic acidInfo
- Publication number
- JPS6263859A JPS6263859A JP60203991A JP20399185A JPS6263859A JP S6263859 A JPS6263859 A JP S6263859A JP 60203991 A JP60203991 A JP 60203991A JP 20399185 A JP20399185 A JP 20399185A JP S6263859 A JPS6263859 A JP S6263859A
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- Prior art keywords
- pretreatment
- column
- acid
- flow path
- analysis
- Prior art date
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Abstract
Description
【発明の詳細な説明】
（イ）産業上の利用分野
この発明はホモバニリン酸及びバニルマンデル酸の自動
分析装置に関する。さらに詳しくは、高速液体クロマト
グラフィを用いる分析装置であって、ことに連続的に迅
速な分析が可能であるホモバニリン酸及びバニルマンデ
ル酸の自動分析装置に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application This invention relates to an automatic analyzer for homovanillic acid and vanylmandelic acid. More specifically, the present invention relates to an automatic analyzer for homovanillic acid and vanylmandelic acid, which is an analyzer using high-performance liquid chromatography, and is particularly capable of continuous and rapid analysis.
（ロ）従来の技術
小児ガンの一種である神経芽細胞腫の早期発見法として
、尿中のホモバニリン酸及びバニルマンデル酸の二成分
を検出゛する方法が有用であることが知られている。こ
れは通常高速液体クロマトグラフィを利用し、ＯＤＳカ
ラムなどのシリカ系逆相カラムを用いて分離定理され、
汎用されているＵＶ検出器は選択性に劣る上感度も低い
ために螢光検出器又は電気化学検出器を用いて検出され
ている。さらに最近アニオン交換カラムと電気化学検出
器を用いる方法が報告されている。(b) Prior Art It is known that a method for detecting two components, homovanillic acid and vanylmandelic acid, in urine is useful as a method for early detection of neuroblastoma, which is a type of childhood cancer. This is usually achieved using high-performance liquid chromatography and a separation theorem using a silica-based reverse phase column such as an ODS column.
Since commonly used UV detectors have poor selectivity and low sensitivity, detection is performed using a fluorescence detector or an electrochemical detector. Furthermore, a method using an anion exchange column and an electrochemical detector has recently been reported.
（ハ）発明が解決しようとする問題点
上記のいずれの方法においても、試料中の夾雑成分に妨
害されて、ホモバニリン酸及びバニルマンデル酸の定量
が困難であり、さらにホモバニリために長時間、移動相
や洗浄液を導入する必要があり、−分析時間が長くなる
という問題点があった。(c) Problems to be solved by the invention In any of the above methods, it is difficult to quantify homovanillic acid and vanilmandelic acid due to interference from contaminant components in the sample. It is necessary to introduce a cleaning solution and a cleaning solution, which poses a problem in that the analysis time becomes longer.
この夾雑成分を除去する方法として試料の前処理が挙げ
られるが、抽出操作等の前処理は操作が煩雑であり、又
目的成分の回収率が不安定であり定量性に欠ける点で不
都合であった。Pretreatment of the sample is a method for removing these impurities, but pretreatment such as extraction is inconvenient in that the operations are complicated, the recovery rate of the target component is unstable, and quantitative performance is lacking. Ta.
以上の分析時間が長くかかる点、前処理が必要な点は連
続分析や自動分析に適さず臨床分野への応用という観点
から不都合である。The above-mentioned analysis time is long and pretreatment is required, which makes it unsuitable for continuous analysis or automatic analysis, and is disadvantageous from the viewpoint of clinical application.
この発明はかかる問題点に鑑みイ【されたもので、抽出
操作のごとき前処理を全く行なうことなく、分析時間を
短縮化でき、連続分析や自動分析に適したホモバニリン
酸及びバニルマンデル酸の自動分析装置を提供するもの
である。This invention was developed in view of the above problems, and is suitable for automatic analysis of homovanillic acid and vanylmandelic acid, which shortens analysis time without any pretreatment such as extraction operation, and is suitable for continuous analysis and automatic analysis. It provides equipment.
（ニ）問題点を解決するための手段及び作用かくしてこ
の発明によれば
（お 移動相供給部とアニオン交換又は逆相分離カラム
と検出部をこの順に接続してなる分析流路、（ｂ）
前処理用溶媒又はカラム洗浄液の切換供給部と試料導入
部とからなり、ドレインに接続される前処理用流路、
（ｃ＞ アニオン交換分離カラムからなる前処理カラ
ム及び
＋ｄ＋ 上記（ｃ）の前処理カラムを、分析流路（■
の移動相供給部と分離カラムとの間、又は前処理用溶媒
山）の試料導入部とドレインとの間に流路接続しうる切
換流路とから構成されてなり、
試料導入時に前処理カラム（ｃ１を前処理用流路（ｂ＞
側に流路接続すると共に、前処理用流路（ｂ）に前処理
用溶媒を供給して予備分離し、前処理カラム（ｃ）から
の試料の分離溶出分のうちホモバニリン酸及びバニルマ
ンデル酸溶出分に対応する所定時間のみ前処理カラムを
分析流路（ａ）側に切換えてホモバニリン酸及びバニル
マンデル酸溶出分を分析流路に導入し、かつこの導入後
に前処理用流路＋ｂ）にカラム洗浄液を供給して前処理
カラムの洗浄をホモバニリン酸及びバニルマンデル酸の
分離分析と並行して行なう制御部を設けでなるホモバニ
リン酸及びバニルマンデル酸の自動分析装置が提供され
る。(d) Means and operation for solving the problems Thus, according to the present invention (b)
A pretreatment flow path consisting of a pretreatment solvent or column cleaning liquid switching supply section and a sample introduction section and connected to a drain, (c> a pretreatment column consisting of an anion exchange separation column and +d+ before (c) above) Connect the processing column to the analytical flow path (■
between the mobile phase supply section and the separation column, or between the sample introduction section and the drain of the pretreatment solvent mountain (pretreatment solvent mountain). (c1 is the pretreatment flow path (b>
A flow path is connected to the side, and a pretreatment solvent is supplied to the pretreatment flow path (b) for preliminary separation, and homovanillic acid and vanylmandelic acid elution from the separated eluate of the sample from the pretreatment column (c) is carried out. The pretreatment column is switched to the analysis flow path (a) side for a predetermined period of time corresponding to minutes, and the eluted portions of homovanillic acid and vanylmandelic acid are introduced into the analysis flow path, and after this introduction, the column cleaning solution is transferred to the pretreatment flow path + b). Provided is an automatic analyzer for homovanillic acid and vanylmandelic acid, which is provided with a control unit that supplies homovanillic acid and vanylmandelic acid to wash a pretreatment column in parallel with separation and analysis of homovanillic acid and vanylmandelic acid.
この発明の最も特徴とする点は、前処理操作を行なうこ
となく尿等の被測定試料を直接高速液体クロマトグラフ
ィーに付し、かつ迅速に連続分析しうるよう構成した点
にある。そしてぞのために試料を前処理カラムに導入し
て予備分離し、ホモバニリン酸及びバニルマンデル酸に
対応する溶出分のみを分離カラムで精密分離しく第３図
、第４図及び第５図参照）、これと平行して前処理カラ
ムの洗浄を行ない次の分析に備えるものである。The most distinctive feature of this invention is that it is constructed so that a sample to be measured, such as urine, can be directly subjected to high performance liquid chromatography without any pretreatment and can be rapidly and continuously analyzed. For this purpose, the sample is introduced into a pretreatment column for preliminary separation, and only the eluate corresponding to homovanillic acid and vanilmandelic acid is precisely separated using the separation column (see Figures 3, 4, and 5). In parallel with this, the pretreatment column is washed in preparation for the next analysis.
上記前処理カラムとしては、アニオン交換ｈラムが選択
され、例えば３ｈｉｍ Ｐａｃｋ ＷＡＸ −１、
（島津製作所製）の名称で入手可能である。As the pretreatment column, an anion exchange column is selected, such as 3him Pack WAX-1,
(manufactured by Shimadzu Corporation).
前処理カラムで予備分離するための前処理溶媒としては
、０．０１〜０．５Ｍの酢酸緩衝液、り土ン酸緩衝液又
はリン酸緩衝液が適切であり、かかる処理液を媒体とし
て被測定試料を前処理カラムに通過させることにより、
効率良く予備分離が行なわれ、ホモバニリン酸及びバニ
ルマンデル酸に対応する溶出分のみが切換流路の制御に
より分析流路に導入され、他の溶出分はドレインより開
渠される。As the pretreatment solvent for preliminary separation in the pretreatment column, 0.01 to 0.5M acetate buffer, phosphate buffer, or phosphate buffer is suitable; By passing the measurement sample through the pretreatment column,
Preliminary separation is carried out efficiently, and only the eluates corresponding to homovanillic acid and vanylmandelic acid are introduced into the analysis flow path by controlling the switching flow path, and the other eluates are drained through the drain.
分析流路に導入された溶出分は次いで分離カラムにより
精密分析される。分離カラムとしてはアニオン交換カラ
ム又は逆相分離カラム（例えばＯＤＳカラム、ＣＮカラ
ム、 Ｃａカラム等）が好適である。移動相供給部より
供給される移動相としてはリン酸緩衝液が適切であり、
試料の保持力の点で州は６〜７が好ましい。The eluate introduced into the analysis channel is then precisely analyzed by a separation column. As the separation column, an anion exchange column or a reverse phase separation column (eg, ODS column, CN column, Ca column, etc.) is suitable. Phosphate buffer is suitable as the mobile phase supplied from the mobile phase supply unit.
In terms of sample retention, the number of states is preferably 6 to 7.
この精密分析に並行して、前処理カラムには洗浄液が流
され前処理カラムに残る尿中の多くの成分の洗浄が行な
われる。この洗浄は、前処理用流路における前処理用溶
媒又はカラム洗浄液の切換供給部を洗浄液側とすること
により行なわれ、この切換はホモバニリン酸及びバニル
マンデル酸溶出分の分析流路への導入後、航処理流路側
に切換えられた直後もしくは切換後の所定時間後に行な
われる。In parallel with this precise analysis, a cleaning solution is flowed through the pretreatment column to wash away many components of the urine remaining in the pretreatment column. This cleaning is performed by switching the pretreatment solvent or column cleaning solution supply part in the pretreatment channel to the cleaning solution side, and after introducing the homovanillic acid and vanylmandelic acid eluates into the analysis channel, This is performed immediately after switching to the air processing flow path side or after a predetermined time after switching.
洗浄液としては０．５〜１Ｍの塩濃度の緩衝液、たとえ
ば０．５Ｍのリン？ＩＩ緩衝液などが使用できる。The washing solution is a buffer solution with a salt concentration of 0.5 to 1M, such as 0.5M phosphorus. II buffer etc. can be used.
検出部に使用する検出器としては、通常用いられる検出
器が用いられる。螢光検出器または電気化学検出器を用
いることが望ましい。′電気化学検出器としては、例え
ば７ンベＤメトリ、クーロメトリ等が使用できる。As a detector used in the detection section, a commonly used detector is used. Preferably, a fluorescent or electrochemical detector is used. 'As the electrochemical detector, for example, 7-beam D-metry, coulometry, etc. can be used.
この装置を自動制御するマイクロ」ンビ］−ターを内蔵
したシステムコント［］−ラ０３１のフローチャートを
第５図に示した。FIG. 5 shows a flowchart of a system controller 031 having a built-in microcontroller for automatically controlling this device.
なお、前処理用溶媒又は移動相の供給部はグラジェント
溶離用のものであってもよく、各流路の上流には、これ
らの溶液中の夾雑物の一部を除去すべくいわゆる予備カ
ラムが設置されていてもよい。Note that the pretreatment solvent or mobile phase supply section may be for gradient elution, and a so-called preliminary column is installed upstream of each flow path to remove some of the impurities in these solutions. may be installed.
（ホ）実施例
第１図はこの発司のホモバニリン酸及びバニルマンデル
酸の自動分析装置を示す構成説明図である。図において
自動分析装置（１）は、移動相供給部（ａ分離カラム（
３）及び検出部（４）とからなる分析流路と、前処理用
溶媒供給部（５）、洗浄液供給部（６）と試料導入部（
７１とからなりドレイン（８）に接続される前処理用流
路並びに前処理カラム００）どから基本構成されてイに
る。(E) Example FIG. 1 is an explanatory diagram of the construction of an automatic analyzer for homovanillic acid and vanylmandelic acid produced by this company. In the figure, the automatic analyzer (1) has a mobile phase supply section (a separation column (
3) and a detection section (4), a pretreatment solvent supply section (5), a cleaning liquid supply section (6), and a sample introduction section (
71 and a pretreatment flow path connected to the drain (8) and a pretreatment column 00).
そして分析流路と前処理用流路とは六方電磁弁高圧切換
バルブ（９）で切換可能に連結されている。The analysis flow path and the pretreatment flow path are switchably connected by a six-way solenoid high-pressure switching valve (9).
なお図中、０１）はレコーダー、０ｚはドレイン、０３
）はシステムコントローラをそれぞれ示す。分析に際し
ては、まずバルブ（９）が破線側とされ試料導入部（刀
から被測定試料が導入され、バルブ（′１４）を実線側
として前処理用溶媒供給部（５）からの溶媒によって前
処理カラム（１０）に導入される。ここでシステムコン
トローラ（１３）のυ１１１１によって、ホモバニリン
酸溶出開始時間（ｔ、）までの夾雑成分の溶出分はドレ
インから廃棄される。ホモバニリン酸溶出開始時間（ｔ
、〉からバニルマンデル酸溶出終了時間（ｔ２〉までの
溶出分はバルブ（９）を実線側に切換えて分離カラム（
３）に導かれ、移動相供給部（２１から供給される移動
相を用いて分離分析される。バニルマンデル酸溶出終了
時間（ｔ２）後に溶出する夾雑成分はバルブ（９）を破
線側に切換えることによりドレインより廃棄される。こ
の直後もしくは切換後の所定時間後にバルブ（１４）が
破線側に切換えられる。これにより洗浄液供給部（６）
から洗浄液が航処理カラム（ト））に導入されて前処理
カラムの洗浄が、分離分析と並行して進行する。このあ
と再びバルブ（９）は実線側に切換えられて次の分析に
ががるべく早漏される。なお、これらのバルブの切換の
タイミングはシステムコントローラ（１３）によって自
動制御されている。In the figure, 01) is the recorder, 0z is the drain, and 03
) indicates the system controller. During analysis, first, the valve (9) is set to the dotted line side, and the sample to be measured is introduced from the sample introduction part (sword). is introduced into the processing column (10). Here, the elution of contaminant components up to homovanillic acid elution start time (t,) is discarded from the drain by υ1111 of the system controller (13). Homovanillic acid elution start time (t,) t
,〉 to vanylmandelic acid elution end time (t2〉), switch the valve (9) to the solid line side and transfer the eluate to the separation column (
3) and is separated and analyzed using the mobile phase supplied from the mobile phase supply section (21).For contaminant components eluted after the vanyl mandelic acid elution end time (t2), switch the valve (9) to the dotted line side. Immediately after this or after a predetermined time after switching, the valve (14) is switched to the side shown by the broken line.This causes the cleaning liquid supply section (6) to be discarded.
A cleaning solution is introduced into the pretreatment column (g), and the cleaning of the pretreatment column proceeds in parallel with the separation analysis. After this, the valve (9) is switched again to the solid line side to allow premature ejaculation in order to prepare for the next analysis. Note that the timing of switching these valves is automatically controlled by a system controller (13).
上記装置を用いて、下記の条件下で分析を行”Ｋつだ。Analysis was performed using the above apparatus under the following conditions.
（試料）
新生児尿 １００誠を０，９ｉ１の蒸留水に添加して注
入用試料とした。(Sample) Newborn urine 100 sigma was added to 0.9i1 distilled water to prepare a sample for injection.
（分析条件）
前処理カラム（至）：４ｍｍφ×５．：ｍのステンレス
管に粒子径１０．、のアニオン交換
型シリカをつめたもの
（Ｓｈｉｍ −ｐａｃｋ ＷＡＸ −１：島津製作所
製）
前処理用溶媒 ： ５０ｍ Ｍ酢酸緩衝液（ｐＨ４，５
）流量１）／／ｍｉｎ
分離カラム（３）：４ｍｍφＸ５Ｃ３ｍのスデ：／レス
管に粒子径３４の７ニオン交換型シ
リカをつめたもの
（Ｓｈｉｎ −ｐａｃｋ ＷＡＸ−１：島津製作所製
作）
移動相： ０，１Ｍリン酸緩衝液（ｐｕ ６．Ｏ）流
量０．５ｇｆ／ｎ１ｉｎ
洗浄ａ＋ ０．５Ｍ リン１１１１１１ （ＰＨ７，
０＞検出器（４）：吸光度検出器 波長２５４ｎｌｌｌ
ホモバニリン酸溶出開始時間ｔＩＺ、Ｓ分バニルマンデ
ル酸溶出終了時間ｔ２９．５分この結果を第４図に示し
た。(Analysis conditions) Pretreatment column (to): 4mmφ×5. : Particle size 10.m in stainless steel tube. (Shim-pack WAX-1: manufactured by Shimadzu Corporation) Pretreatment solvent: 50mM acetate buffer (pH 4,5
) Flow rate 1) //min Separation column (3): 4 mm φ x 5 C 3 m 7-ion exchange type silica packed in a 4 mm φ x 5 C 3 m tube (Shin-pack WAX-1: manufactured by Shimadzu Corporation) Mobile phase: 0.1M phosphate buffer (pu 6.O) flow rate 0.5gf/n1in Washing a+ 0.5M phosphorus 111111 (PH7,
0>Detector (4): Absorbance detector wavelength 254nllll
Homovanillic acid elution start time tIZ, S minutes Vanylmandelic acid elution end time t29.5 minutes The results are shown in FIG.
このように、この発明の装置によれば、被測定試料中の
夾雑成分が除去されて、ホモバニリン酸及びバニルマン
デル酸が明瞭に分離されていることがわかる。Thus, it can be seen that, according to the apparatus of the present invention, contaminant components in the sample to be measured are removed and homovanillic acid and vanylmandelic acid are clearly separated.
（へ）発明の効果
この発明の装置によれば、流路系に直接尿等の試料を導
入してホモバニリン酸及びバニルマンデル酸の分離室Ｍ
を行なうことができる。従来のごどき抽出操作等の前処
理を要しないため分析操作が短時間かつ簡便であり、さ
らに抽出操作に基づく誤差が解消されるという利点を有
している。(F) Effects of the Invention According to the apparatus of the present invention, a sample such as urine can be directly introduced into the flow path system to separate homovanillic acid and vanilmandelic acid into the separation chamber M.
can be done. Since preprocessing such as conventional extraction operations is not required, analysis operations are short and simple, and furthermore, it has the advantage of eliminating errors caused by extraction operations.
ことに、分離カラムによる分析と同時に前処理カラムの
洗浄を行４ｒうので、迅速な連続分析が可能となり、自
動化が容易となる。In particular, since the pretreatment column is washed 4 times at the same time as the analysis using the separation column, rapid continuous analysis becomes possible and automation becomes easy.
第１図はこの発明の装置の一例を示す構成説明図、第２
図は無処理の尿のクロマトグラム図、第３図は前処理を
行ない夾雑成分を除去した尿のクロマトグラム図、第４
図はこの発明の装置によって得られるクロマトグラム図
、第５図はこの装置の自動制御の７０−ヂヤー１−であ
る。
（１）・・・・・・自動分析装置、 （２）・・・・
・・移仙相供給部、（３）・・・・・・分離カラム、
（４）・・・・・・検出部、（５）・・・・・・
前処理用溶媒供給部、（６）・・・・・−洗浄液供給部
、（′７１・・・・・・試料導入部、 （８）・
・・・・・ドｌノ・イン、（９）・・・・・・高圧切換
バルブ、 呻・・・・・・］ｙｉ処理カラム、（１１
）・・・・・・レコーダー、 ■・・・・・・ド
レイン、０３）・・−・・・システムコントローラ、０
４）・・・・・・バルブ。
第１図
第２図
第４ 図
（鵡叶１１１１Ｉｃ分） 藻坪叶閣關第５図FIG. 1 is a configuration explanatory diagram showing an example of the device of the present invention, and FIG.
The figure is a chromatogram of untreated urine, Figure 3 is a chromatogram of urine that has been pretreated to remove contaminants, and Figure 4 is a chromatogram of urine after pretreatment to remove contaminant components.
The figure shows a chromatogram obtained by the apparatus of the present invention, and FIG. 5 shows a 70-degree automatic control of this apparatus. (1)... Automatic analyzer, (2)...
...transfer phase supply section, (3) ...separation column,
(4)...Detection section, (5)...
Pretreatment solvent supply section, (6)...-cleaning liquid supply section, ('71...sample introduction section, (8)...
・・・・・・Doll-no-in, (9) ・・・High-pressure switching valve, groan...]yi processing column, (11
)...Recorder, ■...Drain, 03)...System controller, 0
4)...Valve. Figure 1 Figure 2 Figure 4 (Uno 1111Ic section) Motsubo Kanokaku Figure 5
Claims (1)
ラムと検出部をこの順に接続してなる分析流路、 （ｂ）前処理用溶媒又はカラム洗浄液の切換供給部と試
料導入部とからなり、ドレインに接続される前処理用流
路、 （ｃ）アニオン交換分離カラムからなる前処理カラム及
び （ｄ）上記（ｃ）の前処理カラムを、分析流路（ａ）の
移動相供給部と分離カラムとの間、又は前処理用流路（
ｂ）の試料導入部とドレインとの間に流路接続しうる切
換流路とから構成されてなり、 試料導入時に前処理カラム（ｃ）を前処理用流路（ｂ）
側に流路接続すると共に、前処理用流路（ｂ）に前処理
用溶媒を供給して予備分離し、前処理カラム（ｃ）から
の試料の分離溶出分のうちホモバニリン酸及びバニルマ
ンデル酸溶出分に対応する所定時間のみ前処理カラムを
分析流路（ａ）側に切換えてホモバニリン酸及びバニル
マンデル酸溶出分を分析流路に導入し、かつこの導入後
に前処理用流路（ｂ）にカラム洗浄液を供給して前処理
カラムの洗浄をホモバニリン酸及びバニルマンデル酸の
分離分析と並行して行なう制御部を設けてなるホモバニ
リン酸及びバニルマンデル酸の自動分析装置。 ２、移動相がリン酸緩衝液である特許請求の範囲第１項
記載の装置。 ３、前処理用溶媒が０．０１〜０．５Ｍの酢酸緩衝液、
クエン酸緩衝液又はリン酸緩衝液である特許請求の範囲
第１項記載の装置。[Scope of Claims] 1. (a) An analysis channel formed by connecting a mobile phase supply section, an anion exchange or reversed phase separation column, and a detection section in this order; (b) Switchable supply of pretreatment solvent or column cleaning solution (c) a pretreatment column consisting of an anion exchange separation column; and (d) the pretreatment column of (c) above is connected to an analysis flow path ( a) between the mobile phase supply section and the separation column, or the pretreatment flow path (
It is composed of a switching flow path that can be connected between the sample introduction part of b) and the drain, and when introducing the sample, the pretreatment column (c) is connected to the pretreatment flow path (b).
A flow path is connected to the side, and a pretreatment solvent is supplied to the pretreatment flow path (b) for preliminary separation, and homovanillic acid and vanylmandelic acid elution from the separated eluate of the sample from the pretreatment column (c) is carried out. The pretreatment column is switched to the analysis flow path (a) side for a predetermined period of time corresponding to minutes, and the eluted portions of homovanillic acid and vanylmandelic acid are introduced into the analysis flow path, and after this introduction, the pretreatment column is transferred to the pretreatment flow path (b). An automatic analyzer for homovanillic acid and vanylmandelic acid, which is provided with a control unit that supplies a cleaning solution to wash a pretreatment column in parallel with the separation and analysis of homovanillic acid and vanylmandelic acid. 2. The device according to claim 1, wherein the mobile phase is a phosphate buffer. 3. Pretreatment solvent is 0.01-0.5M acetate buffer;
The device according to claim 1, which is a citrate buffer or a phosphate buffer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60203991A JPS6263859A (en) | 1985-09-13 | 1985-09-13 | Automatic analyzer for homovanillic acid and vanilamandelic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60203991A JPS6263859A (en) | 1985-09-13 | 1985-09-13 | Automatic analyzer for homovanillic acid and vanilamandelic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6263859A true JPS6263859A (en) | 1987-03-20 |
Family
ID=16482968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60203991A Pending JPS6263859A (en) | 1985-09-13 | 1985-09-13 | Automatic analyzer for homovanillic acid and vanilamandelic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6263859A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01142458A (en) * | 1987-11-30 | 1989-06-05 | Yokogawa Electric Corp | Measurement of cation with very low density |
| JPH01131157U (en) * | 1988-03-02 | 1989-09-06 | ||
| JPH0269655A (en) * | 1988-09-05 | 1990-03-08 | Japanese Res & Dev Assoc Bio Reactor Syst Food Ind | On-line automatic analyzing instrument for bioreactor |
| JPH02310468A (en) * | 1989-05-25 | 1990-12-26 | Shiseido Co Ltd | Automatic analysis apparatus of creatinine, homovanillic acid and vanilyl mandelic acid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55103462A (en) * | 1979-02-02 | 1980-08-07 | Hitachi Ltd | Analysis method for urine composing material |
| JPS5940255A (en) * | 1982-08-31 | 1984-03-05 | Shimadzu Corp | Analytical system of indoleacetic acid |
-
1985
- 1985-09-13 JP JP60203991A patent/JPS6263859A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55103462A (en) * | 1979-02-02 | 1980-08-07 | Hitachi Ltd | Analysis method for urine composing material |
| JPS5940255A (en) * | 1982-08-31 | 1984-03-05 | Shimadzu Corp | Analytical system of indoleacetic acid |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01142458A (en) * | 1987-11-30 | 1989-06-05 | Yokogawa Electric Corp | Measurement of cation with very low density |
| JPH01131157U (en) * | 1988-03-02 | 1989-09-06 | ||
| JPH0269655A (en) * | 1988-09-05 | 1990-03-08 | Japanese Res & Dev Assoc Bio Reactor Syst Food Ind | On-line automatic analyzing instrument for bioreactor |
| JPH02310468A (en) * | 1989-05-25 | 1990-12-26 | Shiseido Co Ltd | Automatic analysis apparatus of creatinine, homovanillic acid and vanilyl mandelic acid |
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