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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 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
  • 609-99-4 N
3D model (JSmol)
  • Interactive image
2220661
ChEBI
  • CHEBI:53648 Y
ChEMBL
  • ChEMBL2260697
ChemSpider
  • 11380 Y
ECHA InfoCard 100.009.278
EC Number
  • 210-204-3
5309
KEGG
  • C11319 Y
  • 11873
UNII
  • 2ACT5NW8HU Y
  • DTXSID9060576
  • 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
  • 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:
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).
N verify (what is YN ?)

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. ^ . 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.


dinitrosalicylic, acid, dnsa, iupac, name, hydroxy, dinitrobenzoic, acid, aromatic, compound, that, reacts, with, reducing, sugars, other, reducing, molecules, form, amino, nitrosalicylic, acid, which, strongly, absorbs, light, first, introduced, method, detec. 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 3 5 Dinitrosalicylic acid 1 NamesPreferred IUPAC name 2 Hydroxy 3 5 dinitrobenzoic acidOther names 3 5 Dinitrosalicylic acidIdentifiersCAS Number 609 99 4 N3D model JSmol Interactive imageBeilstein Reference 2220661ChEBI CHEBI 53648 YChEMBL ChEMBL2260697ChemSpider 11380 YECHA InfoCard 100 009 278EC Number 210 204 3Gmelin Reference 5309KEGG C11319 YPubChem CID 11873UNII 2ACT5NW8HU YCompTox Dashboard EPA DTXSID9060576InChI 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 YKey LWFUFLREGJMOIZ UHFFFAOYSA N YInChI 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 UHFFFAOYAQSMILES c1c cc c c1C O O O N O O N O O PropertiesChemical formula C 7H 4N 2O 7Molar mass 228 116 g mol 1Appearance Yellow needles or platesMelting point 182 C 360 F 455 K Solubility in water SolubleSolubility in organic solvents Soluble in ethanol diethyl ether benzeneHazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H315 H318 H319 H335Precautionary 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 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSynthesis Edit3 5 Dinitrosalicylic acid can be prepared by the nitration of salicylic acid 5 References Edit 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 This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 3 5 Dinitrosalicylic acid amp oldid 1118573885, wikipedia, wiki, book, books, library,

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