3,5-Dinitrosalicylic acid

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]

3,5-Dinitrosalicylic acid[1]
Names
Preferred IUPAC name
2-Hydroxy-3,5-dinitrobenzoic acid
Other names
3,5-Dinitrosalicylic acid
Identifiers
3D model (JSmol)
2220661
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.278
EC Number
  • 210-204-3
5309
KEGG
UNII
  • 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) checkY
    Key: LWFUFLREGJMOIZ-UHFFFAOYSA-N checkY
  • 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
  • c1c(cc(c(c1C(=O)O)O)[N+](=O)[O-])[N+](=O)[O-]
Properties
C7H4N2O7
Molar mass 228.116 g·mol−1
Appearance Yellow needles or plates
Melting point 182 °C (360 °F; 455 K)
Soluble
Solubility in organic solvents Soluble in ethanol, diethyl ether, benzene
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H315, H318, H319, H335
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

Synthesis

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

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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