Ninhydrin

HCID 10236

Basic information

CAS
485-47-2
Standard SMILES
O=C1c2ccccc2C(=O)C1(O)O
InChIKey
FEMOMIGRRWSMCU-UHFFFAOYSA-N
Molecular formula
C9H6O4
Average molar mass
178.14 g/mol
Monoisotopic mass
178.02660867

Names & identifiers

Preferred name
Ninhydrin
IUPAC
2,2-dihydroxyindene-1,3-dione
English name
Ninhydrin hydrate
Molecular formula
C9H6O4
Molecular weight
178.14

Names & synonyms

NINHYDRIN485-47-2Ninhydrin hydrate1,2,3-Indantrione monohydrate2,2-Dihydroxy-1H-indene-1,3(2H)-dione1H-Indene-1,3(2H)-dione, 2,2-dihydroxy-Triketohydrindene hydrate2,2-Dihydroxy-1,3-indandione2,2-Dihydroxy-1,3-indanedione1,2,3-Indantrione, 2-hydrateDTXSID70257161,3-Indandione, 2,2-dihydroxy-
Show more names
2,2-Dihydroxyindane-1,3-dione1H-Indene-1,2,3-trione2,2-dihydroxyindene-1,3-dioneNinhydrin, reagent ACS 25GRNINNinthydrin
HCL6S9K23ADTXCID605716CHEBI:86374Indantrione MonohydrateMonohydrate, IndantrioneRefChem:854157207-618-1Ninhydrine

Database identifiers

CAS
485-47-2
PubChem CID
10236
DTXSID
DTXSID7025716
ChEMBL
CHEMBL1221925
ChEBI
CHEBI:86374
UNII
HCL6S9K23A
Nikkaji
J6.001A

Properties

Computed structural properties

XLogP
0.1
Topological polar surface area
74.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
13

Physicochemical properties

Melting point
250 °C · 250 °C (dec.) (lit.)
Boiling point
230.35 °C · 230.35°C (rough estimate)
bulk density
680 kg/m3 · 680kg/m3
Density
0.862 · 0.862
vapor density
6.16 · 6.16 (vs air)
refractive index
1.4209 · 1.4209 (estimate)

Safety & regulation

Safety data

F
8
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
NK5425000
ridadr
UN 1170 3/PG 2

Chemistry & industry

Applications · 5 items

DescriptionNinhydrin is historically the most common reagent for processing fingerprints on porous substrates. It has been used as a fingerprint reagent since the 1950s but has been used as a cell stain since the early 1900s. Ninhydrin molecules form a complex with amino acids resulting in a purple product known as Ruhmann's purple. Purple fingerprints are easily visible on light-colored porous substrates but may be difficult to see on patterned or dark-colored substrates. DFO reacts with amino acids to produce a fluorescent product that is not readily seen with the naked eye. This makes it a useful reagent on dark or patterned porous items. DFO prints are viewed with an alternate light source or laser set to 530–570 nm (green light) through a red barrier filter. 1,2-indanedione is an emerging fingerprint reagent that results in visible pink fingerprints that are also fluorescent. The fluorescence is viewed under the same conditions as DFO. These chemicals can be used on their own or in sequence to develop latent prints on porous substrates. If they are used in sequence, they are used in the following order: indanedione, DFO, ninhydrin. If a reagent is used out of sequence, it will inhibit or limit the effectiveness of the other reagents. In this laboratory exercise you will develop fingerprints on a porous substrate using indanedione, DFO, and ninhydrin. ninhydrin structure

HistoryNinhydrin was discovered in 1910 by the German-English chemist Siegfried Ruhemann (1859–1943). In the same year, Ruhemann observed ninhydrin's reaction with amino acids. In 1954, Swedish investigators Oden and von Hofsten proposed that ninhydrin could be used to develop latent fingerprints.

UsesNinhydrin is used for the detection of free amino groups in amino acids, peptides and proteins.

UsesNinhydrin is an amino acid-sensitive reagent for the development of latent fingermarks on porous surfaces. More sensitive alternatives, such as DFO and IND-Zn, are now available and these have advantages on porous substrates that are not highly luminescent. However, ninhydrin can still be applied after these treatments and may reveal additional ridge detail, particularly on highly luminescent substrates where luminescence visualization may be problematic.

General DescriptionWhite to light yellow crystals or powder. Becomes anhydrous with reddening at 257-266°F.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Ninhydrin is a member of the class of indanones that is indane-1,3-dione bearing two additional hydroxy substituents at position 2. It has a role as a colour indicator and a human metabolite. It is a member of indanones, a beta-diketone, an aromatic ketone and a ketone hydrate.

Related reactions

256 records

Compound notes

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