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3,5-Dinitrosalicylic acid

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3,5-Dinitrosalicylic acid
Names
Preferred IUPAC name 2-Hydroxy-3,5-dinitrobenzoic acid
Other names 3,5-Dinitrosalicylic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 2220661
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.278 Edit this at Wikidata
EC Number
  • 210-204-3
Gmelin Reference 5309
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: LWFUFLREGJMOIZ-UHFFFAOYSA-N
  • 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)(=O))(=O)
Properties
Chemical formula C7H4N2O7
Molar mass 228.116 g·mol
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 GHS05: CorrosiveGHS07: Exclamation mark
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 and has since been widely used, for example, for quantifying carbohydrate levels in blood. It is mainly used in assay of alpha-amylase. However, enzymatic methods are usually preferred due to DNS's lack of specificity.

Synthesis

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

References

  1. 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.
  2. Sumner, J.B. Dinitrosalicylic acid: a reagent for the estimation of sugar in normal and diabetic urine. Journal of Biological Chemistry 47, 5, 1921.
  3. "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.
  4. Miller, Gail Lorenz (1959). "Use of dinitrosalicylic acid reagent for determination of reducing sugar". Anal. Chem. 31 (3): 426–428. doi:10.1021/ac60147a030.
  5. 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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