Ninhydrin
General
Systematic name	Triketohydrindane hydrate
Chemical formula	C9H6O4
Molecular mass	xx.xx g/mol
Appearance	White pale yellow crystals
CAS number	[485-47-2]
EINECS No	207-618-1
SMILES	xxxxx
Properties
Density	0.862 g/cm³
Melting point	250 °C
Boiling point	xx.x °C
Hazards
LD50	78 mg/kg
R-phrases	R22, R36, R37, R38
S-phrases	S26, S28, S36
Disclaimer and references

Ninhydrin, (Triketohydrindane hydrate) is a chemical used to detect ammonia or primary amines. When reacting with these free amines, a deep blue or purple color is evolved. Ninhydrin is most commonly used to detect fingerprints, as amines left over from peptides and proteins (terminal amines or lysine residues) sloughed off in fingerprints react with ninhydrin.^[1] Image File history File links Ninhydrin. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... The tip of a finger showing the friction ridge structure. ... Lysine is one of the 20 amino acids normally found in proteins. ...

Uses

Ninhydrin can also be used to monitor deprotection in solid phase peptide synthesis. When the growing peptide chain is deprotected, a ninhydrin test yields blue. If the next peptide residue is coupled then the test is colorless or yellow. It has been suggested that this article or section be merged into peptide synthesis. ...

Ninhydrin is also used in amino acid analysis of proteins: Most of the amino acids are hydrolyzed and reacted with ninhydrin except Proline; 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 chromatography. Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ... what tyler Kyle A chemist is shown using column chromatographic apparatus in the mid-1950s to separate constituents in a coal tar color analysis Pictured is a sophisticated gas chromatography system. ...

A solution suspected of containing the ammonium ion can be tested by ninhydrin by dotting it onto a solid support (such as silica gel); treatment with ninhydrin should result in a dramatic purple color if the solution contains this species. Fumes from hydrochloric acid and ammonia forming a white cloud of ammonium chloride Ammonium is also an old name for the Siwa oasis in western Egypt. ... Beads of silica gel Silica gel is a granular, porous form of silica made synthetically from sodium silicate. ...

Mechanism to generate the ninhydrin chromophore

Note that in order to generate the ninhydrin chromophore, 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 Schiff base 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. a mixture of 4,4-diaminodiphenyl ether 1 (1. ...

Mechanism for the ninhydrin test File links The following pages link to this file: Ninhydrin ...

See also

Paper chromatography Paper chromatography is an analytical technique for separating and identifying compounds that are or can be colored, especially pigments. ...

References

1. ^ http://www.bergen.org/EST/Year5/fingerprint.htm

External links

• External MSDS
• External MSDS