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P2297

Sigma-Aldrich

Picrylsulfonic acid solution

5 % (w/v) in H2O, BioReagent, suitable for determination of primary amines

Synonym(s):

2,4,6-Trinitrobenzenesulfonic acid solution, TNBS

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About This Item

Empirical Formula (Hill Notation):
C6H3N3O9S
CAS Number:
Molecular Weight:
293.17
Beilstein:
572358
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.25

product line

BioReagent

Quality Level

concentration

5 % (w/v) in H2O

suitability

suitable for determination of primary amines

storage temp.

2-8°C

SMILES string

OS(=O)(=O)c1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C6H3N3O9S/c10-7(11)3-1-4(8(12)13)6(19(16,17)18)5(2-3)9(14)15/h1-2H,(H,16,17,18)

InChI key

NHJVRSWLHSJWIN-UHFFFAOYSA-N

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General description

Picrylsulfonic acid solution is a hapten, which can bind to tissue proteins and turn into an antigen. This leads to several immunologic responses. Colitis induced by a 2,4,6-trinitrobenzene sulfonic acid (TNBS) is a type of delayed hypersensitivity reaction to haptenized proteins. Leukotriene B4 (LTB4) and the monhydroxyl fatty acids 5-hydroxyeicosatetraenoic acid (5-HETE), 12-HETE, and 15-HETE are the major inflammatory mediators involved in this TNBS-induced colitis. Ethanol when used in high concentration act as a vehicle for the TNBS administration.

Application

Hydrophilic modifying reagent. Derivatives with amino compounds can be regenerated with hydrazine.
Picrylsulfonic acid solution has been used:
  • to assess the efficiency of carboxymethyl lysine (CML) modifications of exposed primary amines
  • to incubate zona intact bovine embryos for the differential staining of blastocysts
  • to induce irritable bowel syndrome (IBS) in mice and to study its effects on Clostridium butyricum

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Pictograms

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Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Is Product P2297, Picrylsulfonic acid solution, supposed to be yellow?

    Yes. This product is a clear to slightly hazy yellow solution at room temperature. The solution has a concentration of 5 w/v % in H2O (5g per 100 mL).

  4. In general, what is Product P2297, Picrylsulfonic acid solution, used for?

    Picrylsulfonic acid has been used 1) As a hydrophilic modifying reagent[1]; 2) To make derivatives with amino compounds, which can be regenerated with hydrazine [2].

  5. How is Product P2297, Picrylsulfonic acid solution, tested? Do you have any references for its use besides Sigma's method?

    Sigma's suitability assay is based on a published method.1 We use a 500-fold dilution as a working solution, with glycine as a standard. Hydrochloric acid is used to stop the reaction, and to reduce yellow background due to picric acid.  Sodium phosphate is used as a buffer in place of sodium bicarbonate to avoid formation of CO2 when HCl is added.  Absorbance is read at 420 nm.Other procedures have been published. For example:---Twenty-five mL of 0.03 M TNBS is added to 1 mL of sample (in borate buffer), agitated to ensure complete mixing, and allowed to stand for 30 minutes at room temperature (25±1°C).  No quenching step is used.  In the blank, buffer replaces sample.  Absorbance is read at 420 nm.2---Protocols using a more concentrated solution of picric acid (1.1 M) have been published.3Note: TNBS forms an orange complex with amines, monitored at 420 nm, but the EmM of the complexes will vary with the reacting group:  for alpha-amino groups, 22.0; for epsilon-amino groups, somewhat lower; and for thiol groups, 2.25.3References:1. Satake, K. et al., J. Biochem., 47, 654 (1960).2. Snyder, S.L. and Sobocinski P.Z., Anal. Biochem., 64, 284-288 (1975).3. Fields, R., Methods in Enzymology, 25, 464-468 (1972).

  6. What are the suggested storage conditions for Product P2297, Picrylsulfonic acid solution?

    Store Product No. P2297 at 2-8°C in the dark.

  7. Is Product P2297, Picrylsulfonic acid solution, considered to be stable?

    It is explosive when it is dry. The solution should be stored at 2-8°C in the dark. Under these conditions less than 5% decomposition will occur over five months. At 37°C, 50% decomposition occurred in 60 days.  Picrylsulfonic acid decomposes to picric acid, crystals of which may form in the solution, but this impurity causes no interference in usage. The solution may also contain a trace amount of 2,4-dinitrophenol (typically <0.5%).  Storage at -20°C may enhance shelf-life of stock solutions.

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  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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    Ask a Scientist here.

Mengdie Shen et al.
Mediators of inflammation, 2020, 3070345-3070345 (2020-10-27)
To explore the treatment effect of mica on 2,4,6-trinitrobenzenesulfonic acid solution- (TNBS-) induced colitis in mice. Thirty male BALB/C mice were randomly divided into the control group, the TNBS group, and the mica group. Control mice were treated with saline
Elliot Yi-Hsin Lin et al.
Biomedicines, 8(8) (2020-08-09)
Aberrant neutrophil extracellular trap (NET) formation and the loss of barrier integrity in inflamed intestinal tissues have long been associated with inflammatory bowel disease (IBD). However, whether NETs alter intestinal epithelium permeability during colitis remains elusive. Here, we demonstrated that
Joel Castro et al.
Gastroenterology, 145(6), 1334-1346 (2013-08-21)
Linaclotide is a minimally absorbed agonist of guanylate cyclase-C (GUCY2C or GC-C) that reduces symptoms associated with irritable bowel syndrome with constipation (IBS-C). Little is known about the mechanism by which linaclotide reduces abdominal pain in patients with IBS-C. We
Manuela Désirée Bienert et al.
Plant physiology, 158(3), 1220-1229 (2012-01-05)
The leaf extracellular space contains several peptidases, most of which are of unknown function. We isolated cDNAs for two extracellular serine carboxypeptidase III genes from tobacco (Nicotiana tabacum), NtSCP1 and NtSCP2, belonging to a phylogenetic clade not yet functionally characterized
Wei Jiang et al.
The Journal of experimental medicine, 210(11), 2465-2476 (2013-09-26)
NOD2 functions as an intracellular sensor for microbial pathogen and plays an important role in epithelial defense. The loss-of-function mutation of NOD2 is strongly associated with human Crohn's disease (CD). However, the mechanisms of how NOD2 maintains the intestinal homeostasis

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