3,5-Dinitrosalicylic acid

3,5-Dinitrosalicylic acid^[1]

Names

Preferred IUPAC name

2-Hydroxy-3,5-dinitrobenzoic acid

Other names

3,5-Dinitrosalicylic acid

Identifiers

CAS Number

609-99-4^N

3D model (JSmol)

Interactive image

Beilstein Reference

2220661

ChEBI

CHEBI:53648^Y

ChEMBL

ChEMBL2260697

ChemSpider

11380^Y

ECHA InfoCard

100.009.278

EC Number

210-204-3

Gmelin Reference

5309

KEGG

C11319^Y

PubChem CID

11873

UNII

2ACT5NW8HU^Y

CompTox Dashboard (EPA)

DTXSID9060576

InChI

InChI=1S/C7H4N2O7/c10-6-4(7(11)12)1-3(8(13)14)2-5(6)9(15)16/h1-2,10H,(H,11,12)^Y
Key: LWFUFLREGJMOIZ-UHFFFAOYSA-N^Y
InChI=1/C7H4N2O7/c10-6-4(7(11)12)1-3(8(13)14)2-5(6)9(15)16/h1-2,10H,(H,11,12)
Key: LWFUFLREGJMOIZ-UHFFFAOYAQ

SMILES

c1c(cc(c(c1C(=O)O)O)[N+](=O)[O-])[N+](=O)[O-]

Properties

Chemical formula

C₇H₄N₂O₇

Molar mass

228.116 g·mol⁻¹

Appearance

Yellow needles or plates

Melting point

182 °C (360 °F; 455 K)

Solubility in water

Soluble

Solubility in organic solvents

Soluble in ethanol, diethyl ether, benzene

Hazards

GHS labelling:

Pictograms

Signal word

Danger

Hazard statements

H302, H315, H318, H319, H335

Precautionary statements

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

3,5-Dinitrosalicylic acid (DNS or DNSA, IUPAC name 2-hydroxy-3,5-dinitrobenzoic acid) is an aromatic compound that reacts with reducing sugars and other reducing molecules to form 3-amino-5-nitrosalicylic acid, which strongly absorbs light at 540 nm. It was first introduced as a method to detect reducing substances in urine by James B. Sumner^[2] and has since been widely used, for example, for quantifying carbohydrate levels in blood.^[3] It is mainly used in assay of alpha-amylase. However, enzymatic methods are usually preferred due to DNS's lack of specificity.^[4]

Synthesis

3,5-Dinitrosalicylic acid can be prepared by the nitration of salicylic acid.^[5]

References

^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–318. ISBN 978-0-8493-0594-8.
^ Sumner, J.B. Dinitrosalicylic acid: a reagent for the estimation of sugar in normal and diabetic urine. Journal of Biological Chemistry 47, 5, 1921.
^ "Description of lab use from the Department of Chemical Engineering, University of Maryland". Archived from the original on 2007-08-17. Retrieved 2006-03-17.
^ Miller, Gail Lorenz (1959). "Use of dinitrosalicylic acid reagent for determination of reducing sugar". Anal. Chem. 31 (3): 426–428. doi:10.1021/ac60147a030.
^ Thiel, W.; Mayer, R.; Jauer, E.-A.; Modrow, H.; Dost, H.: Synthesis and Spectral Characterization of Blue Dyes of the Benzene Series in J. Prakt. Chem. (Leipzig) 328 (1986) 497-514, doi:10.1002/prac.19863280406.

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Synthesis

References