Structure via PubChem · Public domain (PubChem)
ninhydrin
Sign in to saveAlso known as 2,2-Dihydroxyindane-1,3-dione, 1,2,3-Indantrione, 2-hydrate, Triketohydrindene hydrate, 2,2-Dihydroxy-1,3-indandione, 1,2,3-Indantrione monohydrate
Ninhydrin (2,2-dihydroxyindane-1,3-dione) is an organic compound with the formula C6H4(CO)2C(OH)2. It is used to detect ammonia and amines. 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 fingerprints in forensic cases, as the terminal amines of lysine residues in peptides and proteins sloughed off in fingerprints react with ninhydrin.
Chemical data
- Formula
- C9H6O4
- Molecular weight
- 178.14 g/mol
- IUPAC name
- 2,2-dihydroxyindene-1,3-dione
- SMILES
- C1=CC=C2C(=C1)C(=O)C(C2=O)(O)O
- InChIKey
- FEMOMIGRRWSMCU-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 74.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,134 papers- Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences.Journal of agricultural and food chemistry · 2004
- A Ninhydrin-Type Urea Sorbent for the Development of a Wearable Artificial Kidney.Macromolecular bioscience · 2020
- The development of novel ninhydrin analogues.Chemical Society reviews · 2005
- The Ninhydrin Reaction Revisited: Optimisation and Application for Quantification of Free Amino Acids.Molecules (Basel, Switzerland) · 2024
- Ninhydrin-functionalized chitosan for selective removal of Pb(II) ions: Characterization and adsorption performance.International journal of biological macromolecules · 2021
via PubMed
Wikidata facts
- Mass
- 178.027
Show 3 more facts
- chemical formula
- C₉H₆O₄
- canonical SMILES
- C1=CC=C2C(=C1)C(=O)C(C2=O)(O)O
- Commons category
- Ninhydrin
via Wikidata · CC0
~5 min read
Article
7 sectionsContents
- History
- Uses
- Forensics
- Reactivity
- Effects on health
- See also
- References
Ninhydrin (2,2-dihydroxyindane-1,3-dione) is an organic compound with the formula C6H4(CO)2C(OH)2. It is used to detect ammonia and amines. 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 fingerprints in forensic cases, as the terminal amines of lysine residues in peptides and proteins sloughed off in fingerprints react with ninhydrin.
Ninhydrin is a white solid that is soluble in ethanol and acetone. Ninhydrin can be considered as the hydrate of indane-1,2,3-trione.