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151173 Sigma-Aldrich

Ninhydrin

ACS reagent

Synonym: 1,2,3-Indantrione monohydrate, 2,2-Dihydroxy-1,3-indanedione, Trioxohydrindene monohydrate

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Properties

Related Categories Amino Acids, Analytical Reagents, Analytical/Chromatography, Derivatization Reagents, Derivatization Reagents HPLC,
grade   ACS reagent
identification and melting point   passes test
color   white to brownish-white, crystals
mp   250 °C (dec.)(lit.)
solubility   H2O: passes test
suitability   passes test for sensitivity to amino acids

Description

Application

Used for the detection of free amino groups in amino acids, peptides and proteins.

Used in the detection and assay of peptides, amino acids, amines, and amino sugars yielding highly fluorescent ternary compounds with aldehydes and primary amines. Reaction with sarcosine or proline gives azomethine ylides.

Packaging

10, 25, 100 g in glass bottle

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
WGK Germany 
3
RTECS 
NK5425000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Reagent for detecting and assaying peptides, amino acids, amines and amino sugars. Samejima, K. Anal. Biochem. 42, 222, 237, (1971)

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Tetrahedron 34, 1285, (1978)

Gazz. Chim. Ital. 123, 137, (1993)

Review. Schoenberg, A., Singer, E. Tetrahedron 34, 1285, (1978)

Amino acid analysis: ninhydrin reaction with titanous chloride. James, L.B. J. Chromatogr. Sci. 152, 298, (1978)

Quantitative determination of chitosan and the percentage of free amino groups. Anal. Biochem. 211, 240, 242, (1993)

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Amino acid analysis: aqueous dimethyl sulfoxide as solvent for the ninhydrin reaction. Moore, S. J. Biol. Chem. 243, 6281-6283, (1968)

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Kaiser test. Kaiser, E. Anal. Biochem. 34, 595, (1970)

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A viscoelastic chitosan-modified three-dimensional porous poly(L-lactide-co-ε-caprolactone) scaffold for cartilage tissue engineering. Li C, Wang L, Yang Z, et al. J. Biomater. Sci. Polym. Ed. 23(1-4), 405-24, (2012)

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Antimicrobial activity of marine sponge Clathria indica (Dendy, 1889). Ravichandran S, Wahidullah S, D'Souza L, et al. Bioorg. Khim. 37(4), 483-9, (2011)

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Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences. Friedman M J. Agric. Food Chem. 52(3), 385-406, (2004)

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Locally released small (non-protein) ninhydrin-reacting molecules underlie developmental differences of cultured medullary versus spinal dorsal horn neurons. Xie YF, Pflueger M, Feng S, et al. J. Neurochem. 122(3), 605-18, (2012)

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Surgical repair of a 30 mm long human median nerve defect in the distal forearm by implantation of a chitosan-PGA nerve guidance conduit. Gu J, Hu W, Deng A, et al. J. Tissue Eng. Regen. Med. 6(2), 163-8, (2012)

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The development of novel ninhydrin analogues. Hansen DB and Joullie MM Chem. Soc. Rev. 34(5), 408-17, (2005)

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CaCl(2) as a bifunctional reusable catalyst: diversity-oriented synthesis of 4H-pyran library under ultrasonic irradiation. Safaei HR, Shekouhy M, Shirinfeshan A, et al. Mol. Divers. 16(4), 669-83, (2012)

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Moistened hands do not necessarily allude to high quality fingerprints: the relationship between palmar moisture and fingerprint donorship. Almog J, Sheratzki H, Elad-Levin M, et al. J. Forensic Sci. 56 Suppl 1, S162-5, (2011)

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Micelle-catalyzed reaction between ninhydrin and nickel dipeptide complex [Ni(II)-Gly-Tyr]+. Akram M, Kumar D, and Kabir-ud-Din Colloids Surf. B Biointerfaces 94, 220-5, (2012)

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Fragment-based discovery and optimization of BACE1 inhibitors. James Madden et al Bioorg. Med. Chem. Lett. 20, 5329-33, (2010)

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Continuous stationary phase gradients for planar chromatographic media. Kannan B, Marin MA, Shrestha K, et al. J. Chromatogr. A 1218(52), 9406-13, (2011)

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Determination of in-gel protein concentration by a ninhydrin-based method. Kang SU and Lubec G Proteomics 11(3), 481-4, (2011)

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Carcass mass can influence rate of decomposition and release of ninhydrin-reactive nitrogen into gravesoil. Spicka A, Johnson R, Bushing J, et al. Forensic Sci. Int. 209(1-3), 80-5, (2011)

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Chemical enhancement of footwear impressions in urine on fabric. Farrugia KJ, Bandey H, Bleay S, et al. Forensic Sci. Int. 214(1-3), 67-81, (2012)

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Preparation and characterization of PEGyated Concanavalin A for affinity chromatography with improved stability Wen, Z. and B. Niemeyer J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 879, 1732-1740, (2011)

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A modified ninhydrin micro-assay for determination of total cyanogens in plants. Surleva A and Drochioiu G Food Chem. 141(3), 2788-94, (2013)

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Estimation of stature from hand impression: a nonconventional approach. Ahemad N and Purkait R J. Forensic Sci. 56(3), 706-9, (2011)

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Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine. Sotgia S, Zinellu A, Pinna GA, et al. Talanta 85(4), 1783-5, (2011)

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Molecular structure, vibrational spectral analysis, NBO, HOMO-LUMO and conformational studies of ninhydrin. Arivazhagan M and Anitha Rexalin D Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 104, 451-60, (2013)

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A colorimetric assay of 1-aminocyclopropane-1-carboxylate (ACC) based on ninhydrin reaction for rapid screening of bacteria containing ACC deaminase. Li Z, Chang S, Lin L, et al. Lett. Appl. Microbiol. 53(2), 178-85, (2011)

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Determination of efficacy of fingermark enhancement reagents; the use of propyl chloroformate for the derivatization of fingerprint amino acids extracted from paper. Mink T, Voorhaar A, Stoel R, et al. Sci. Justice 53(3), 301-8, (2013)

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Chemical enhancement of footwear impressions in blood on fabric - part 3: amino acid staining. Farrugia KJ, Bandey H, Savage K, et al. Sci. Justice 53(1), 8-13, (2013)

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An assessment of the effectiveness of 5-methylthioninhydrin within dual action reagents for latent fingerprint development on paper substrates. Porpiglia N, Bleay S, Fitzgerald L, et al. Sci. Justice 52(1), 42-8, (2012)

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Multicomponent reactions for the synthesis of functionalized imidazoles. Seyfi S, Hossaini Z, and Rostami-Charati F Comb. Chem. High Throughput Screen 16(8), 652-6, (2013)

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RGDS-fuctionalized alginates improve the survival rate of encapsulated embryonic stem cells during cryopreservation. Sambu S, Xu X, Schiffer HA, et al. Cryo. Letters 32(5), 389-401, (2011)

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Latent fingermark development on a range of porous substrates using ninhydrin analogs--a comparison with ninhydrin and 1,8-diazofluoren. Berdejo S, Rowe M, and Bond JW J. Forensic Sci. 57(2), 509-14, (2012)

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In situ observation of ninhydrin and phenylhydrazine reaction in solution by FTIR. Turhan O and Tezbaşaran E Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 113, 297-301, (2013)

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Antimicrobial activity and second harmonic studies on organic non-centrosymmetric pure and doped ninhydrin single crystals. Prasanyaa T, Jayaramakrishnan V, and Haris M Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 104, 110-3, (2013)

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Novel rearrangements in the reactions directed toward preparation of spiro-N,N-ketals: reactions of naphthalene-1,8-diamine with ninhydrin and isatin. Akita M, Seto H, Aoyama R, et al. Molecules 17(12), 13879-90, (2012)

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An investigation into the enhancement of fingermarks in blood on fruit and vegetables. Rae L, Gentles D, and Farrugia KJ Sci. Justice 53(3), 321-7, (2013)

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An investigation into the enhancement of fingermarks in blood on paper with genipin and lawsone. Thomas P and Farrugia K Sci. Justice 53(3), 315-20, (2013)

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1,3-Ninhydrin dihydrazone featuring an R4(4)(12) motif with 4 symmetry and comprising only N and H atoms. Blake AJ, Chebude Y, Tadesse H, et al. Acta Crystallogr. C 68(Pt 9), o362-4, (2012)

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Commentary. Bennett MJ Clin. Chem. 57(4), 549-50, (2011)

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Commentary. Cowan TM Clin. Chem. 57(4), 548-9, (2011)

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Merck 14,6554

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