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N4876

Sigma-Aldrich

Ninhydrin

Ninhydrin

suitable for amino acid detection

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:
24897715
NACRES:
NA.21
Pricing and availability is not currently available.

form

powder

Quality Level

200

mp

250 °C (dec.) (lit.)

solubility

ethanol: 100 mg/mL
H2O: 50 mg/mL (with sonication)

suitability

suitable for amino acid detection

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 is an important building block in organic synthesis and has been employed to prepare a variety of chemicals for complexing and/or sensing metal ions. It is an amino acid-sensitive reagent used for the preparation of Ruhemann′s purple.[1]

Application

Ninhydrin can be used:
  • For the detection of free amino groups in amino acids, peptides, and proteins.
  • As a ligand for the Cu-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides to synthesize N-arylheterocycles.
  • As a reactant to synthesize aldols by reacting with active methylene compounds.
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
BCCM2714
BCCL3628
BCCK4886
BCCK2178
BCCK6576

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Substituted naphthoquinones as novel amino acid sensitive reagents for the detection of latent fingermarks on paper surfaces
Jelly R, et al.
Talanta, 82, 1717-1724 (2010)
Vibrational spectroscopy and density functional theory study of ninhydrin.
Li R, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 136, 1642-1648 (2015)
Quantitative determination of chitosans by ninhydrin.
Prochazkova S, et al.
Carbohydrate Polymers, 38(2), 115-122 (1999)
Reaction of diaminofurazane with ninhydrin.
Pirogov SV, et al.
Chemistry of Heterocyclic Compounds, 33(12), 1473-1474 (1997)
Wort Free Amino Nitrogen Analysis Adapted to a Microplate Format.
Schmitt MR and Budde AD
Journal of the American Society of Brewing Chemists, 70(2), 95-95 (2012)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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