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A0554

4-Acetamido-4′-isothiocyanato-2,2′-stilbenedisulfonic acid disodium salt hydrate

Name: 4-Acetamido-4&#8242;-isothiocyanato-2,2&#8242;-stilbenedisulfonic acid disodium salt hydrate
Brand: SIGMA

powder, ≥80%

Synonym(s):

Disodium 4-acetamido-4′-isothiocyanato-stilben-2,2′-disulfonate, SITS

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₁₂N₂Na₂O₇S₃ · xH₂O

CAS Number:

51023-76-8

Molecular Weight:

498.46 (anhydrous basis)

NACRES:

NA.77

PubChem Substance ID:

24890434

UNSPSC Code:

12352202

EC Number:

256-919-4

MDL number:

MFCD00007485

Beilstein/REAXYS Number:

9177451

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Product Name

4-Acetamido-4′-isothiocyanato-2,2′-stilbenedisulfonic acid disodium salt hydrate, ≥80%

Quality Level

100

assay

≥80%

form

powder

storage temp.

−20°C

SMILES string

[Na+].[Na+].CC(=O)Nc1ccc(\C=C\c2ccc(cc2S([O-])(=O)=O)N=C=S)c(c1)S([O-])(=O)=O

InChI

1S/C17H14N2O7S3.2Na/c1-11(20)19-15-7-5-13(17(9-15)29(24,25)26)3-2-12-4-6-14(18-10-27)8-16(12)28(21,22)23;;/h2-9H,1H3,(H,19,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2/b3-2+;;

InChI key

NPAWAMRXPHRVQY-WTVBWJGASA-L

Related Categories

Proteins & Enzymes

Detection Substrates & Enzymes

Application

Fluorescent marker for membranes; inhibits anion permeability of membranes. Also inactivates Na,K-ATPase, by covalent modification of a specific Lys residue.

Other Notes

Predominantly trans-isomer

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H302,H315,H319,H334,H335

pcodes

P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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SITS Derivatization of Peptides to Enhance 266 nm Ultraviolet Photodissociation (UVPD).

M Montana Quick et al.

Journal of the American Society for Mass Spectrometry, 28(7), 1462-1472 (2017-03-21)

N-terminal derivatization of peptides with the chromogenic reagent 4-acetamido-4-isothiocyanatostilbene-2,2-disulfonic acid (SITS) is demonstrated to enhance the efficiency of 266 nm ultraviolet photodissociation (UVPD). Attachment of the chromophore results in a mass shift of 454 Da and provides significant gains in the number

Inactivation of the Na,K-ATPase by modification of Lys-501 with 4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid (SITS).

C H Pedemonte et al.

FEBS letters, 314(1), 97-100 (1992-12-07)

The sodium pump or Na,K-ATPase, maintains the Na+ and K+ gradients across eukaryotic cell membranes at the expense of ATP. Incubation of purified canine renal Na,K-ATPase with 4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid (SITS) inhibited the ATPase activity. Both the labeling of the protein

Mechanisms and regulation of chloride transport in the Malpighian tubules of the larval cabbage looper Trichoplusia ni.

Dennis Kolosov et al.

Insect biochemistry and molecular biology, 116, 103263-103263 (2019-11-05)

Malpighian tubules (MTs) and the hindgut together constitute the excretory system of insects. Larvae of lepidopterans (butterflies and moths) demonstrate the so-called cryptonephric arrangement, where the distal blind end of each MT is embedded into the rectal complex. The rest

Cell volume decrease as a link between azaspiracid-induced cytotoxicity and c-Jun-N-terminal kinase activation in cultured neurons.

Carmen Vale et al.

Toxicological sciences : an official journal of the Society of Toxicology, 113(1), 158-168 (2009-10-10)

Azaspiracids (AZAs) are a group of marine toxins recently described that currently includes 20 members. Not much is known about their mechanism of action, although the predominant analog in nature, AZA-1 targets several organs in vivo, including the central nervous

Agonist-dependent potentiation of vanilloid receptor transient receptor potential vanilloid type 1 function by stilbene derivatives.

Xuan Zhang et al.

Molecular pharmacology, 81(5), 689-700 (2012-02-14)

Transient receptor potential vanilloid type 1 (TRPV1) is a nonselective cation channel activated by capsaicin, low pH, and noxious heat and plays a key role in nociception. Understanding mechanisms for functional modulation of TRPV1 has important implications. One characteristic of

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Global Trade Item Number

SKU	GTIN
A0554-1G	04061826740781
A0554-250MG	04061833334089

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