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			{{Use dmy dates|date=February 2023}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 402506633		| verifiedrevid = 412692887
	| Name = Ninhydrin		| Name = Ninhydrin
	| ImageFile = Ninhydrin-2D-skeletal.png		| ImageFile = Ninhydrin.svg
	| ImageFile1 = Ninhydrin-3D.jpg		| ImageFile1 =
	| ImageSize = 200px		| ImageSize =
	| ImageName = Ninhydrin		| ImageName = Ninhydrin
			| ImageFile2 = Ninhydrin sample.jpg
⚫	| IUPACName = 2,2-Dihydroxyindane-1,3-dione
			| ImageSize2 = 300px
⚫	| Section1 = {{Chembox Identifiers
			| PIN = 2,2-Dihydroxy-1''H''-indene-1,3(2''H'')-dione
		⚫	| OtherNames = 2,2-Dihydroxyindane-1,3-dione<br />1,2,3-Indantrione hydrate
		⚫	|Section1={{Chembox Identifiers
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| CASNo = 485-47-2
	| PubChem = 10236		| PubChem = 10236
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEMBL = 1221925
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID = 9819
			| EC_number = 213-340-1
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = HCL6S9K23A
	| InChI = 1/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H		| InChI = 1/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H
	| InChIKey = FEMOMIGRRWSMCU-UHFFFAOYAM		| InChIKey = FEMOMIGRRWSMCU-UHFFFAOYAM
⚫	| ChEMBL = 1221925
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H		| StdInChI = 1S/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = FEMOMIGRRWSMCU-UHFFFAOYSA-N		| StdInChIKey = FEMOMIGRRWSMCU-UHFFFAOYSA-N
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| CASNo = 485-47-2
	| SMILES = O=C2c1ccccc1C(=O)C2(O)O		| SMILES = O=C2c1ccccc1C(=O)C2(O)O
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID = 9819
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=9 | H=6 | O=4		| C=9 | H=6 | O=4
			| Formula = C<sub>9</sub>H<sub>6</sub>O<sub>4</sub>
		⚫	| Appearance = White solid
	| Density = 0.862 g/cm<sup>3</sup>		| Density = 0.862 g/cm<sup>3</sup>
			| Solubility = 20 g L<sup>−1</sup><ref name=merck>''Chemicals and reagents'', 2008–2010, Merck</ref>
	| MeltingPtC = 250		| MeltingPtC = 250
			| MeltingPt_notes = (decomposes)
	| BoilingPt =		| BoilingPt =
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
			| GHSPictograms = {{GHS07}}
	| RPhrases = {{R22}}, {{R36}}, {{R37}}, {{R38}}
			| GHSSignalWord = Warning
	| SPhrases = {{S26}}, {{S28}}, {{S36}}
			| HPhrases = {{H-phrases|302|315|319|335}}
	| ExternalMSDS =
			| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
			| ExternalSDS =
	}}		}}
	}}		}}
	'''Ninhydrin''' (2,2-Dihydroxyindane-1,3-dione) is a chemical used to detect ] or primary and secondary ]s. When reacting with these free amines, a deep blue or purple color known as Ruhemann's purple is produced. Ninhydrin is most commonly used to detect ]s, as the ]s or ] residues in peptides and proteins sloughed off in fingerprints react with ninhydrin.<ref>http://www.bergen.org/EST/Year5/fingerprint.htm</ref>		'''Ninhydrin''' (2,2-dihydroxyindane-1,3-dione) is an ] with the formula C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>C(OH)<sub>2</sub>. It is used to detect ] and ]s. Upon reaction with these amines, ninhydrin gets converted into deep blue or purple derivatives, which are called Ruhemann's purple. Ninhydrin is most commonly used to detect ]s in ] cases, as the terminal ]s of ] residues in ] and ] sloughed off in fingerprints react with ninhydrin.<ref>{{cite web|archive-url=https://web.archive.org/web/20070613175807/http://www.bergen.org/EST/Year5/fingerprint.htm|archive-date=13 June 2007|title=Fingerprinting Analysis|publisher=Bergen County Technical Schools|url=http://www.bergen.org/EST/Year5/fingerprint.htm|date=June 2003|url-status=dead}}</ref><ref>{{cite book |doi=10.1002/0471238961.0615180506091908.a01.pub3|chapter=Forensic Chemistry|title=Kirk-Othmer Encyclopedia of Chemical Technology|year=2015|last1=Rowe|first1=Walter F.|pages=1–19|isbn=9780471238966}}</ref>
			Ninhydrin is a white solid that is soluble in ] and ].<ref name=merck/> Ninhydrin can be considered as the ] of ].
			== History ==
			Ninhydrin was discovered in 1910 by the German-English chemist Siegfried Ruhemann (1859–1943).<ref>{{cite journal|author=Ruhemann, Siegfried |year=1910|url=https://archive.org/stream/p2journal97chemuoft#page/1438/mode/2up |title=Cyclic Di- and Tri-ketones|journal=Journal of the Chemical Society, Transactions|volume=97|pages= 1438–1449|doi=10.1039/ct9109701438}}</ref><ref>{{cite journal |author=West, Robert |date=1 July 1965 |title=Siegfried Ruhemann and the Discovery of Ninhydrin |url=https://pubs.acs.org/doi/abs/10.1021/ed042p386 |journal=Journal of Chemical Education |volume=42 |issue=7 |pages=386–388 |bibcode=1965JChEd..42..386W |doi=10.1021/ed042p386}}</ref> In the same year, Ruhemann observed ninhydrin's reaction with ].<ref>{{cite journal|author=Ruhemann, S. |year=1910|url=https://archive.org/stream/p2journal97chemuoft#page/2024/mode/2up |title=Triketohydrindene Hydrate|journal=Journal of the Chemical Society, Transactions|volume=97|pages=2025–2031|doi=10.1039/ct9109702025}}</ref> In 1954, Swedish investigators Oden and von Hofsten proposed that ninhydrin could be used to develop latent fingerprints.<ref>{{cite journal|author1=Odén, Svante|author2=von Hofsten, Bengt|name-list-style=amp|year= 1954|title=Detection of Fingerprints by the Ninhydrin Reaction|url=https://ui.adsabs.harvard.edu/abs/1954Natur.173..449O/abstract|doi=10.1038/173449a0|pmid= 13144778|journal=Nature|volume=173|issue=4401|pages= 449–450|bibcode=1954Natur.173..449O |s2cid=4187222}}</ref><ref>{{cite web|last1=Oden|first1=Svante.|url=http://pdfpiw.uspto.gov/.piw?Docid=02715571&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect2%3DPTO1%2526Sect2%3DHITOFF%2526p%3D1%2526u%3D%2Fnetahtml%2FPTO%2Fsearch-bool.html%2526r%3D1%2526f%3DG%2526l%3D50%2526d%3DPALL%2526S1%3D2715571.PN.%2526OS%3DPN%2F2715571%2526RS%3DPN%2F2715571&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page|title=Process of Developing Fingerprints}} U.S. Patent no. 2,715,571 (filed: 27 September 1954; issued: 16 August 1955).</ref>
	==Uses==		==Uses==
	Ninhydrin can also be used to monitor deprotection in ] (Kaiser Test).<ref>E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, ''Analytical Biochemistry'' 34 595 (1970)</ref> The chain is linked via its ] to the solid support, with the N-terminus extending off it. When that nitrogen is deprotected, a ninhydrin test yields blue. Amino-acid residues are attached with their N-terminus protected, so if the next residue has been successfully coupled onto the chain, the test gives a colorless or yellow result.		Ninhydrin can be used in Kaiser test to monitor ] in ].<ref>{{cite journal|doi=10.1016/0003-2697(70)90146-6|title=Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides |journal=Analytical Biochemistry|volume= 34|issue=2 |year=1970|last1=Kaiser |first1=E. |last2=Colescott |first2=R.L. |last3=Bossinger |first3=C.D. |last4=Cook |first4=P.I. |pages=595–8 |pmid=5443684 }}</ref> The chain is linked via its ] to the solid support, with the ] extending off it. When that nitrogen is deprotected, a ninhydrin test yields blue. Amino-acid residues are attached with their N-terminus protected, so if the next residue has been successfully coupled onto the chain, the test gives a colorless or yellow result.
	Ninhydrin is also used in amino acid analysis of proteins: Most of the amino acids are ] and reacted with ninhydrin except ]; Also, certain amino acid chains are degraded. Therefore, separate analysis is required for identifying such amino acids that either react differently or don't react at all with ninhydrin. The rest of the amino acids are then quantified colorimetrically after separation by ].		Ninhydrin is also used in ] of proteins. Most of the amino acids, except ], are ] and react with ninhydrin. Also, certain amino acid chains are degraded. Therefore, separate analysis is required for identifying such amino acids that either react differently or do not react with ninhydrin at all. The rest of the amino acids are then quantified colorimetrically after separation by ].
	A solution suspected of containing the ] ion can be tested by ninhydrin by dotting it onto a solid support (such as ]); treatment with ninhydrin should result in a dramatic purple color if the solution contains this species. In the analysis of a chemical reaction by ], the reagent can also be used. It will detect, on the TLC plate, virtually all ]s, ]s and also, after vigorous heating, ]s.		A solution suspected of containing the ] ion can be tested by ninhydrin by dotting it onto a solid support (such as ]); treatment with ninhydrin should result in a dramatic purple color if the solution contains this species. In the analysis of a chemical reaction by ] (TLC), the reagent can also be used (usually 0.2% solution in either n-butanol or in ethanol). It will detect, on the TLC plate, virtually all ]s, ]s and also, after vigorous heating, ]s.
	When ninhydrin reacts with amino acids, the reaction also releases CO<sub>2</sub>. The carbon in this CO<sub>2</sub> originates from the carboxyl carbon of the amino acid. This reaction has been used to release the carboxyl carbons of bone ] from ancient bones<ref>C. I. Keeling, D. E. Nelson, K. N. Slessor, ''Archaeometry'' 41 151 (1999)</ref> for stable ] in order to help reconstruct the palaeodiet of ].<ref>C. I. Keeling, D. E. Nelson, ''Oecologia'' 127 495 (2001)</ref> Release of the carboxyl carbon (via ninhydrin) from amino acids recovered from soil that has been treated with a labeled substrate demonstrates assimilation of that substrate into microbial protein<ref>Marsh, K. L., R. L. Mulvaney, and G. K. Sims. 2003. A technique to recover tracer as carboxyl-carbon and α-nitrogen from amino acids in soil hydrolysates. J. AOAC. 86:1106-1111.</ref>. This approach was successfully used to reveal that some ammonium oxidizing bacteria, also called ] use ] as a carbon source in soil<ref>Marsh, K. L., G. K. Sims, and R. L. Mulvaney. 2005. Availability of urea to autotrophic ammonia-oxidizing bacteria as related to the fate of 14C- and 15N-labeled urea added to soil. Biol. Fert. Soil. 42:137-145.</ref>.		Upon reaction with ninhydrin, amino acids undergo ]. The released CO<sub>2</sub> originates from the carboxyl carbon of the amino acid. This reaction has been used to release the carboxyl carbons of bone ] from ancient bones<ref>{{cite journal|author1=Keeling, C. I. |author2=Nelson, D. E. |author3=Slessor, K. N. |name-list-style=amp |journal=Archaeometry|volume= 41 |pages=151–164 |year=1999|doi=10.1111/j.1475-4754.1999.tb00857.x|title=Stable Carbon Isotope Measurements of the Carboxyl Carbons in Bone Collagen|url=http://summit.sfu.ca/system/files/iritems1/6994/b17944776.pdf}}</ref> for stable ] in order to help reconstruct the palaeodiet of ].<ref>{{cite journal|author1=Keeling, C. I. |author2=Nelson, D. E. |journal=Oecologia|volume= 127|issue=4|pages=495–500|year=2001|jstor=4222957|doi=10.1007/S004420000611|title=Changes in the Intramolecular Stable Carbon Isotope Ratios with Age of the European Cave Bear (''Ursus spelaeus'')|pmid=28547486 |bibcode=2001Oecol.127..495K |s2cid=23508811 }}</ref> Release of the carboxyl carbon (via ninhydrin) from amino acids recovered from soil that has been treated with a labeled substrate demonstrates assimilation of that substrate into microbial protein.<ref>{{cite journal|author=Marsh, K. L., Mulvaney, R. L. and Sims, G. K. |year=2003|title= A Technique to Recover Tracer as Carboxyl-Carbon and α-Nitrogen from Amino Acids in Soil Hydrolysates|journal= J. AOAC Int.|pmid=14979690|volume= 86|issue=6|pages=1106–1111|doi=10.1093/jaoac/86.6.1106|doi-access=free}}</ref> This approach was successfully used to reveal that some ammonium oxidizing bacteria, also called ] use ] as a carbon source in soil.<ref>{{cite journal|author=Marsh, K. L., Sims, G. K. and Mulvaney, R. L. |year= 2005|title= Availability of Urea to Autotrophic Ammonia-Oxidizing Bacteria as Related to the Fate of <sup>14</sup>C- and <sup>15</sup>N-labeled Urea Added to Soil|journal= Biol. Fert. Soil.|volume= 42|issue= 2|pages=137–145|doi=10.1007/s00374-005-0004-2|bibcode= 2005BioFS..42..137M|s2cid= 6245255}}</ref>
			]
	A ninhydrin solution is commonly used by forensic investigators in the analysis of latent fingerprints on porous surfaces such as paper. Amino acid containing fingermarks, formed by minute sweat secretions which gather on the finger's unique ridges, are treated with the ninhydrin solution which turns the amino acid finger ridge patterns purple and therefore visible. <ref>Menzel,E.R. (1986): Manual of fingerprint development techniques. Home Office,Scientific Research and Development Branch, London</ref>
	==Reactivity==		===Forensics===
			A ninhydrin solution is commonly used by ]s in the analysis of ]s on ] surfaces such as paper. The ]s present in the minute sweat secretions that gather on the finger's unique ridges transfer to surfaces that are touched. Exposure of the surface to ninhydrin converts the amino acids into visibly colored products and thus reveals the print.<ref>Menzel, E.R. (1986) ''Manual of fingerprint development techniques''. Home Office, Scientific Research and Development Branch, London. {{ISBN|0862522307}}</ref> The test solutions suffer from poor long-term stability, especially if not kept cold.<ref>{{Cite journal|last1=Janssen-Bouwmeester|first1=Roy|last2=Bremmer|first2=Christiaan|last3=Koomen|first3=Linda|last4=Siem-Gorré|first4=Shermayne|last5=de Puit|first5=Marcel|date=May 2020|title=Positive control tests for fingermark development reagents|journal=Forensic Science International|language=en|volume=310|pages=110259|doi=10.1016/j.forsciint.2020.110259|pmid=32224429|s2cid=214732288}}</ref>
			To further enhance the ability of ninhydrin, a solution of ] and ] (IND-Zn) can be used prior to ninhydrin. This sequence leads to greater overall reaction of the amino acids, possibly by IND-Zn helping to release them from the surface for the subsequent ninhydrin reaction.<ref>{{Cite journal|last1=Mangle|first1=Milery Figuera|last2=Xu|first2=Xioama|last3=de Puit|first3=M.|date=September 2015|title=Performance of 1,2-indanedione and the need for sequential treatment of fingerprints|journal=Science & Justice|language=en|volume=55|issue=5|pages=343–346|doi=10.1016/j.scijus.2015.04.002|pmid=26385717}}</ref>
	{{chembox
	| Name = Indane-1,2,3-trione
	| ImageFile = Indantrione.svg
	| ImageSize = 200px
	| IUPACName = Indane-1,2,3-trione
	| OtherNames = Indanetrione
	| Section1 = {{Chembox Identifiers
	| CASNo = 938-24-9
	| PubChem = 70309
	| SMILES = O=C2c1ccccc1C(=O)C2=O
	}}
	| Section2 = {{Chembox Properties
	| C=9 | H=4 | O=3
⚫	| Appearance = white powder
	| Density = 1.482 g/cm<sup>3</sup>
	| MeltingPt =
	| BoilingPtC = 338.4
	| Solubility =
	}}
	| Section3 = {{Chembox Hazards
	| MainHazards =
	| FlashPt =
	| Autoignition =
	}}
	}}
			==Reactivity==
	The carbon atom of a ] bears a partial positive charge enhanced by neighboring electron withdrawing groups like carbonyl itself. So the central carbon of a 1,2,3-tricarbonyl compound is much more electrophilic than one in a simple ketone. Thus indane-1,2,3-trione reacts readily with nucleophiles, including water. Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups.		Ninhydrin exists in equilibrium with the triketone ], which reacts readily with nucleophiles (including water). Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups.
	Note that in order to generate the ninhydrin ], the amine is condensed with a molecule of ninhydrin to give a Schiff base. Thus only ammonia and primary amines can proceed past this step. At this step, there must also be an alpha proton (H* in the diagram) for ] transfer, so an amine adjacent to a tertiary carbon cannot be detected by the ninhydrin test. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, and this is generally yellow-orange in color.		To generate the ninhydrin ] , the amine must condense to give a ]. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, generally being yellow–orange.
	:]		:]
			==Effects on health==
			Ninhydrin may cause allergic, IgE-mediated rhinitis and asthma.<ref name="Piirilä_1997" >{{cite journal | vauthors = Piirilä P, Estlander T, Hytönen M, Keskinen H, Tupasela O, Tuppurainen M| title = Rhinitis caused by ninhydrin develops into occupational asthma | journal = Eur Respir J | volume = 10 | issue = 8 | pages = 1918–1921| date = August 1997 | doi =10.1183/09031936.97.10081918 |pmid = 9272939 | doi-access = free }}</ref> A case has been described in which a 41 year old forensic laboratory worker working with Ninhydrin developed rhinitis and respiratory difficulty. Her specific IgE levels were found almost doubled.<ref name="Piirilä_1997"/>
	==See also==		==See also==
			{{Commons category}}
			* ]
	* ]		* ]
	==References==		==References==
			{{reflist}}
	<references/>
	]		]
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	]		]
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	]
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	]