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Alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester, preparation method and application

A technology of hydroxycinnamic acid and n-propyl ester, which is applied in the preparation of carboxylic acid nitriles, chemical instruments and methods, and the preparation of organic compounds. It can solve the problems of low mass spectrometry analysis and detection, sample loss, and high prices of commercial products. The effect of reducing requirements and improving test results

Active Publication Date: 2014-01-01
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(2) The samples to be analyzed, especially the actual samples of biological samples such as proteomics research, often have a lot of impurities and other non-protein components, which greatly reduces the sensitivity of mass spectrometry detection and seriously inhibits the signal of the sample, so it is necessary to add additional The desalting steps and impurity removal operations lead to a large loss of samples, and the low sample content brings difficulties to subsequent mass spectrometry analysis and detection
(3) CHCA is not easy to obtain pure products in synthesis and preparation, and the price of commercial products is high

Method used

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  • Alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester, preparation method and application
  • Alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester, preparation method and application
  • Alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of n-propyl α-cyano-4-hydroxycinnamate

[0042] Add 0.2 mL piperidine to ethanol (30 mL), then add propyl cyanoacetate (0.6357 g, 5 mmol) and 4-hydroxybenzaldehyde (0.6717 g, 5.5 mmol). After the solid drug was dissolved, toluene (30 mL) was added, and the temperature was raised to 130° C., stirred and refluxed to remove water for 3 hours to stop the reaction. After cooling to room temperature, it was concentrated to 10 mL by rotary evaporation. The obtained concentrated liquid was poured into 300 mL of primary water, and solids were precipitated, and a slightly yellow powder filter cake was obtained by suction filtration. The filter cake was recrystallized once with ethanol (50 mL) to obtain the slightly yellow product α-cyano-4-hydroxycinnamic acid n-propyl ester (0.7958 g, 0.34 mmol), and the yield was 68.82%.

[0043] The structure identification data of α-cyano-4-hydroxycinnamic acid n-propyl ester are as follows:

[0044] 1 H NMR(300MHz, CDCl 3 )δ...

Embodiment 2

[0046] Example 2: Using α-cyano-4-hydroxycinnamic acid n-propyl ester as a matrix to perform mass spectrometry analysis on protein standards.

[0047] Take various prepared sample solutions (respectively bovine serum albumin (BSA), equine myoglobin (Myoglobin) and bovine insulin (Insulin) standards, all purchased from sigma company, the concentration is 1μM) and matrix solution ( Concentration is 5mM) Mix uniformly at a volume ratio of 1:1, then add 1μL of mixed sample to the MALDI target plate, place it in the air to volatilize the solvent, and then perform mass spectrometry analysis.

[0048] Compared with the traditional matrix α-cyano-4-hydroxycinnamic acid test sample, α-cyano-4-hydroxycinnamic acid n-propyl ester is used as the matrix for BSA ( figure 2 b, m / z66342, [M+H] + ;33153,[2M+H] + ), Myoglobin ( image 3 b, m / z16960.817,[M+H] + ;8479.374,[2M+H] + ,5650.476,[3M+H] + ), Insulin ( Figure 4 b, m / z5734.439) have obtained relatively high signal intensity, so it has better...

Embodiment 3

[0049] Example 3: Mass spectrometry analysis of polypeptide standards.

[0050] Take [Gly 14 ]-Humanin G human (amino acid sequence is Met-Ala-Pro-Arg-Gly-Phe-Ser-Cys-Leu-Leu-Leu-Leu-Thr-Gly-Glu-Ile-Asp-Leu-Pro-Val-Lys -Arg-Arg-Ala, with a concentration of 1μM, purchased from sigma company) The standard solution and matrix solution (with a concentration of 5mM) are mixed uniformly in a volume ratio of 1:1, and then 1μL of the mixed sample is added to the MALDI target plate and placed in the air The solvent is evaporated, and then mass spectrometry is performed.

[0051] Compared with the traditional matrix α-cyano-4-hydroxycinnamic acid test sample, α-cyano-4-hydroxycinnamic acid n-propyl ester is used as the matrix for [Gly 14 ]-Humanin G human( Figure 5 b, m / z2685.761,[M+H] + ;1343.516,[2M+H] + ) Have obtained relatively high signal intensity, and thus have better matrix performance. The amount of the analyte in the figure is 0.5 pmol, which shows that the sensitivity of the ma...

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Abstract

The invention discloses an alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester, a preparation method and an application, and belongs to the technical field of MALDI mass spectra. The preparation method comprises the steps of adding piperidine into a reaction solvent by stirring at the room temperature, then adding cyano propyl acetate and 4-hydroxy benzaldehyde, after the drugs are dissolved, adding methylbenzene, raising the temperature, stopping the reaction after the reflux and water removal, after cooling to the room temperature, conducting rotary evaporation to obtain a concentrated solution containing the alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester, purifying the concentrated solution, pouring the obtained concentrated solution into a large amount of deionized water, immediately separating out solid, conducting suction filtration to obtain a filter cake, and then conducting recrystallization on the filter cake 1-5 times by means of ethyl alcohol to obtain a yellowish product, namely the alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester. By the adoption of a mass spectrometry to detect various samples, and compared with a traditional base material (alpha-cyano-group-4-hydroxycinnamic acid), the alpha-cyano-group-4-hydroxycinnamic acid normal propyl ester has good sensitivity, good detection limit and a better test effect.

Description

Technical field [0001] The invention belongs to the technical field of matrix-assisted laser desorption ionization mass spectrometry (MALDI), and specifically relates to α-cyano-4-hydroxycinnamic acid n-propyl ester, a preparation method and application as a matrix of MALDI. Background technique [0002] Matrix-assisted laser desorption ionization (MALDI) mass spectrometry technology has been favored by researchers from various countries since Tanaka et al. reported in 1988. Matrices play a very important role in MALDI analysis. They can not only absorb and transmit laser energy, but also separate the analyte molecules to prevent them from gathering into clusters to prevent the analyte molecules from being fragmented by strong laser irradiation. A "good" matrix needs to meet several conditions, including strong absorption at the wavelength of the laser used, and mutual solubility with the object to be measured, so that it can be well crystallized together and uniformly. In fact,...

Claims

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Application Information

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IPC IPC(8): C07C255/41C07C253/30G01N27/64
Inventor 国新华肖朝辉刘超王晟
Owner JILIN UNIV
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