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72491

Sigma-Aldrich

Ninhydrin

≥95.0% (UV)

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/REAXYS Number:
1910963
EC Number:
207-618-1
MDL number:
MFCD00003791
UNSPSC Code:
12352100
PubChem Substance ID:
57652420

assay

≥95.0% (UV)

form

crystals

mp

250 °C (dec.) (lit.)

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,[1] is a useful organic building block.[2]

Application

Ninhydrin (Triketohydrindene hydrate) may be used as a reagent for the quantification of amino acids and peptides by photometric method[3] and colorimetric method.[4] 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.[5]
Used for the detection of free amino groups in amino acids, peptides and proteins.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBQ6520V
BCBQ3034V
BCBN5715V
BCBN3972V
BCBM2513V

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Photometric ninhydrin method for use in the chromatography of amino acids.
S MOORE et al.
The Journal of biological chemistry, 176(1), 367-388 (1948-10-01)
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)
Ninhydrin as a building block in scaffold-linked chromophoric dyad construction.
Margetic D, et al.
ARKIVOC (Gainesville, FL, United States), 210, 224-224 (2014)
Yu-Feng Xie et al.
Journal of neurochemistry, 122(3), 605-618 (2012-05-23)
Neurons located in the trigeminal subnucleus caudalis (Vc) play crucial roles in pain and sensorimotor functions in the orofacial region. Because of many anatomical and functional similarities with the spinal dorsal horn (SDH), Vc has been termed the medullary dorsal
Mendel Friedman
Journal of agricultural and food chemistry, 52(3), 385-406 (2004-02-05)
The reaction of ninhydrin with primary amino groups to form the purple dye now called Ruhemann's purple (RP) was discovered by Siegfried Ruhemann in 1910. In addition, imines such as pipecolic acid and proline, the guanidino group of arginine, the
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