3,5-Dinitrosalicylic acid

3,5-Dinitrosalicylic acid^[1]

Names
IUPAC name 2-Hydroxy-3,5-dinitrobenzoic acid
Other names 3,5-Dinitrosalicylic acid
Identifiers
CAS Number	609-99-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:53648
ChemSpider	11380
ECHA InfoCard	100.009.278
KEGG	C11319
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)[N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	C7H4N2O7
Molar mass	228.12 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
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 and has since been widely used, for example, for quantifying carbohydrate levels in blood.^[2] It is mainly used in assay of alpha-amylase. However, enzymatic methods are usually preferred due to DNS lack of specificity.^[3]

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, FL: CRC Press. pp. 3–318. ISBN 0-8493-0594-2.
2. Description of lab use from the Department of Chemical Engineering, University of Maryland
3. Miller, Gail Lorenz (1959). "Use of dinitrosalicylic acid reagent for determination of reducing sugar". Anal. Chem. 31 (3): 426–428. doi:10.1021/ac60147a030.