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(Synonyms: 茚三酮) 目录号 : GC61135

Ninhydrin可作为显色分析探针(chromogenicanalyticalprobe)用于氨基酸和蛋白质的定量分析。

Ninhydrin Chemical Structure

Cas No.:485-47-2

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500mg
¥450.00
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产品描述

Ninhydrin can be used as a chromogenic analytical probe for the quantification of amino acids and proteins.

Ninhydrin is used in amino acid analysis of proteins. Except proline, Most amino acids can be hydrolyzed and react with ninhydrin. The amino acids are then quantified colorimetrically after separation by chromatography.Ninhydrin reacts with primary and secondary amines producing a blue or purple reaction product: diketohydrindylidene-diketohydrindamine.

[1]. Omar MA, et al. Utility of ninhydrin reagent for spectrofluorimetric determination of heptaminol in human plasma.Luminescence. 2018 Sep;33(6):1107-1112. [2]. Anantharaman S, et al. Ninhydrin-sodium molybdate chromogenic analytical probe for the assay of amino acids and proteins.rSpectrochim Acta A Mol Biomol Spectrosc. 2017 Feb 15;173:897-903.

Chemical Properties

Cas No. 485-47-2 SDF
别名 茚三酮
Canonical SMILES O=C1C(O)(O)C(C2=C1C=CC=C2)=O
分子式 C9H6O4 分子量 178.14
溶解度 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 5.6136 mL 28.0678 mL 56.1356 mL
5 mM 1.1227 mL 5.6136 mL 11.2271 mL
10 mM 0.5614 mL 2.8068 mL 5.6136 mL
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Research Update

Ninhydrin-functionalized chitosan for selective removal of Pb(II) ions: Characterization and adsorption performance

Int J Biol Macromol 2021 Apr 30;177:29-39.PMID:33607139DOI:10.1016/j.ijbiomac.2021.02.110.

A chitosan-based adsorbents (CS-Ninhydrin) was prepared by grafting Ninhydrin for Pb(II) ions adsorption. SEM-EDS, XRD and FTIR analysis were used to characterize the synthesized CS-Ninhydrin. The static adsorption experiments showed that CS-Ninhydrin had a good removal rate for Pb(II) ions in a wide range of pH 3 to 7, quickly reached equilibrium (120 min) and had a higher adsorption capacity (196 mg/g). Pseudo second-order and Langmuir models showed that the adsorption process of Pb(II) by CS-Ninhydrin was a single-layer chemical adsorption. Temperature experiments showed that the reaction was a spontaneous exothermic process. In the wastewater experiment, CS-Ninhydrin showed an excellent selectivity to Pb(II) ions. The reusability of CS-Ninhydrin was perfect after five adsorption-desorption cycles. The main adsorption mechanism was the chelating and electrostatic action between N and O groups in CS-Ninhydrin and Pb(II) ions. Therefore, the new adsorbent CS-Ninhydrin was expected to promote the wide application of chitosan in Pb(II) adsorption.

The development of novel Ninhydrin analogues

Chem Soc Rev 2005 May;34(5):408-17.PMID:15852153DOI:10.1039/b315496n.

Following its discovery by Siegfried Ruhemann in 1910, Ninhydrin rapidly became a practical analytical tool. In 1954 it was found to be an important reagent to develop fingerprints on porous surfaces. Since its use in forensic chemistry, many efforts have focused on improving the reagent. Many of the shortcomings of Ninhydrin have been met by the synthesis of a variety of Ninhydrin analogues. This tutorial review provides a short introduction to Ninhydrin and highlights the different synthetic approaches used in the development of analogues for the detection of latent fingerprints.

A Ninhydrin-Type Urea Sorbent for the Development of a Wearable Artificial Kidney

Macromol Biosci 2020 Mar;20(3):e1900396.PMID:32065727DOI:10.1002/mabi.201900396.

The aim of this study is to develop polymeric chemisorbents with a high density of Ninhydrin groups, able to covalently bind urea under physiological conditions and thus potentially suitable for use in a wearable artificial kidney. Macroporous beads are prepared by suspension polymerization of 5-vinyl-1-indanone (vinylindanone) using a 90:10 (v/v) mixture of toluene and nitrobenzene as a porogen. The indanone groups are subsequently oxidized in a one-step procedure into Ninhydrin groups. Their urea absorption kinetics are evaluated under both static and dynamic conditions at 37 °C in simulated dialysate (urea in phosphate buffered saline). Under static conditions and at a 1:1 molar ratio of Ninhydrin: urea the sorbent beads remove ≈0.6-0.7 mmol g-1 and under dynamic conditions and at a 2:1 molar excess of Ninhydrin ≈0.6 mmol urea g-1 sorbent in 8 h at 37 °C, which is a step toward a wearable artificial kidney.

Applications of the Ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences

J Agric Food Chem 2004 Feb 11;52(3):385-406.PMID:14759124DOI:10.1021/jf030490p.

The reaction of Ninhydrin with primary amino groups to form the purple dye now called Ruhemann's purple (RP) was discovered by Siegfried Ruhemann in 1910. In addition, imines such as pipecolic acid and proline, the guanidino group of arginine, the amide groups of asparagine, the indole ring of tryptophan, the sulfhydryl group of cysteine, amino groups of cytosine and guanine, and cyanide ions also react with Ninhydrin to form various chromophores of analytical interest. Since its discovery, extensive efforts have been made to apply manual and automated Ninhydrin reactions as well as Ninhydrin spray reagents to the detection, isolation, and analysis of numerous compounds of interest across a broad spectrum of disciplines. These include agricultural, biochemical, clinical, environmental, food, forensic, histochemical, microbiological, medical, nutritional, plant, and protein sciences. This reaction is unique among chromogenic reactions in that at pH 5.5 it results in the formation of the same soluble chromophore by all primary amines which react, be they amines, amino acids, peptides, proteins, and even ammonia. Because the chromophore is not chemically bound to the protein or other insoluble material, it is not lost when the insoluble substrate is removed by centrifugation or filtration after the reaction is completed. The visible color of the chromophore is distinctive and is generally not affected by the yellow colors present in many food, plant, and tissue extracts. Adaptations of the classical Ninhydrin reaction to specialized needs in analytical chemistry and biochemistry include the use of acid, alkaline, and fluorogenic Ninhydrin reagents. To cross-fertilize information among several disciplines wherein an interest in the Ninhydrin reaction has developed, and to enhance its utility, this review attempts to integrate and correlate the widely scattered literature on Ninhydrin reactions of a variety of structurally different compounds. Specifically covered are the following aspects: historical perspective, chemistry and mechanisms, applications, and research needs. A better understanding of these multifaceted Ninhydrin reactions provide a scientific basis for further improvements of this important analytical technique.

A convenient Ninhydrin assay in 96-well format for amino acid-releasing enzymes using an air-stable reagent

Anal Biochem 2022 Oct 1;654:114819.PMID:35839914DOI:10.1016/j.ab.2022.114819.

An improved and convenient Ninhydrin assay for aminoacylase activity measurements was developed using the commercial EZ Nin™ reagent. Alternative reagents from literature were also evaluated and compared. The addition of DMSO to the reagent enhanced the solubility of Ruhemann's purple (RP). Furthermore, we found that the use of a basic, aqueous buffer enhances stability of RP. An acidic protocol for the quantification of lysine was developed by addition of glacial acetic acid. The assay allows for parallel processing in a 96-well format with measurements microtiter plates.