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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2220661
ChEBI	CHEBI:53648 ;
ChEMBL	ChEMBL2260697;
ChemSpider	11380 ;
ECHA InfoCard	100.009.278
EC Number	210-204-3;
Gmelin Reference	5309
KEGG	C11319 ;
PubChem CID	11873;
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) 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	228.116 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 pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H315, H318, H319, H335
GHS precautionary statements	P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P310, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 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
^ 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.

[hand-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

[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.

[Thiel-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.

[1]

[2]

[3]

[4]

[5]