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151173

Sigma-Aldrich

Ninhydrin

ACS reagent

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H6O4
CAS Number:
485-47-2
Molecular Weight:
178.14
Beilstein:
1910963
EC Number:
207-618-1
MDL number:
MFCD00003791
UNSPSC Code:
12352100
PubChem Substance ID:
24849098
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

description

identification and melting point passes test

form

solid

color

white to brownish white, crystals

mp

250 °C (dec.) (lit.)

solubility

H2O: passes test

suitability

passes test for sensitivity to amino acids

functional group

hydroxyl
ketone

SMILES string

OC1(O)C(=O)c2ccccc2C1=O

InChI

1S/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H

InChI key

FEMOMIGRRWSMCU-UHFFFAOYSA-N

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General description

Ninhydrin, a tricyclic 1,2,3-trione, is a useful organic building block. It is an amino acid reagent, which reveals latent fingerprints on porous surfaces like paper, cardboard and raw wood.
It is employed for nitrite detection in various samples, identifying contamination, and is also used as a colorimetric reagent.

Application

Ninhydrin (Triketohydrindene hydrate) may be used as a reagent for the quantification of amino acids and peptides by photometric method and colorimetric method. It may be used to prepare the ninhydrin reagent, by mixing ninhydrin and hydrindantin (reduced form of ninhydrin) in dimethyl sulfoxide. This reagent is used in manual ninhydrin method for the quantitative determination of amino acids.
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.
Used for the detection of free amino groups in amino acids, peptides and proteins.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000153228
0000153227
0000132437
BCCG3771
BCCG3723

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E Curotto et al.
Analytical biochemistry, 211(2), 240-241 (1993-06-01)
Chitosans were quantified with ninhydrin, a reagent normally used for recognizing and quantifying amino groups. The reaction was time dependent and there was no effect when different acids were added to the mixture. This method was used to determine the
Tetrahedron, 34, 1285-1285 (1978)
Gazzetta Chimica Italiana, 123, 137-137 (1993)
Shao-Ru Wang et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 7(13), 1903770-1903770 (2020-07-17)
CRISPR (clustered regularly interspaced short palindromic repeats) systems have been established as valuable genome-editing tools. Controlling CRISPR systems has high biological significance and this field has garnered intense interest. There is a considerable need for simple approaches with no need
Isomerization of Ninhydrin-Heterocyclic Ketene Aminal Adducts: Kinetic versus Thermodynamic Control, Solvent Dependency and Mechanism.
Chen N, et al.
European Journal of Organic Chemistry, 28, 6210-6218 (2014)
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