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Merck
CN

A36883

Aurintricarboxylic acid ammonium salt

ACS reagent, powder or crystals

Synonym(s):

ATA, Aluminon, Ammonium aurintricarboxylate

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About This Item

Linear Formula:
C22H14O9 · 3NH3
CAS Number:
569-58-4
Molecular Weight:
473.43
UNSPSC Code:
12171500
NACRES:
NA.47
PubChem Substance ID:
24890803
EC Number:
209-319-1
MDL number:
MFCD00040925
Colour Index Number:
43810
Beilstein/REAXYS Number:
3900820

Key Documents

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Product Name

Aurintricarboxylic acid ammonium salt, ACS reagent

InChI

1S/C22H14O9.3H3N/c23-16-4-1-10(7-13(16)20(26)27)19(11-2-5-17(24)14(8-11)21(28)29)12-3-6-18(25)15(9-12)22(30)31;;;/h1-9,23-24H,(H,26,27)(H,28,29)(H,30,31);3*1H3

InChI key

AIPNSHNRCQOTRI-UHFFFAOYSA-N

SMILES string

N.N.N.OC(=O)c1cc(ccc1O)\C(c2ccc(O)c(c2)C(O)=O)=C3/C=CC(=O)C(=C3)C(O)=O

biological source

synthetic

grade

ACS reagent

form

powder or crystals

technique(s)

titration: suitable

impurities

≤0.1% insolubles

ign. residue

≤0.2%

color

dark red

mp

220-225 °C (dec.) (lit.)

solubility

water: soluble 100 mg/mL

λmax

450 nm, 522 nm (2nd)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

Quality Level

300

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Related Categories

Application

Reagent for aluminum

Biochem/physiol Actions

Aurintricarboxylic acid readily polymerizes in aqueous solution, forming a stable free radical that inhibits protein-nucleic acid interactions. It is a potent inhibitor of ribonuclease and topoisomerase II by preventing the binding of the nucleic acid to the enzyme. It stimulates tyrosine phosphorylation processes including the Jak2/STAT5 pathway in NB2 lymphoma cells, ErbB4 in neuroblastoma cells, and MAP kinases, Shc proteins, phosphatidylinositide 3-kinase and phospholipase C in PC12 cells. Aurintricarboxylic acid inhibits apoptosis in many cell types. Its neuroprotective effect, perhaps due to its ability to prevent down-regulation of Ca2+ impermeable GluR2 receptors or to its ability to inhibit calpain, a Ca2+-activated protease that is activated during apoptosis.

Other Notes

May contain a substantial amount of polymeric material.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS8727
SHBT1519
SHBS7143
SHBS8728
SHBR7029

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Jakyung Yoo et al.
Journal of molecular modeling, 18(4), 1583-1589 (2011-08-02)
DNA methyltransferase 1 (DNMT1) is an emerging target for the treatment of cancer, brain disorders, and other diseases. Currently, there are only a few DNMT1 inhibitors with potential application as therapeutic agents or research tools. 5,5-Methylenedisalicylic acid is a novel
Moonhee Lee et al.
Neurobiology of aging, 33(10), 2237-2246 (2012-01-06)
Complement plays a vital role in both the innate and adaptive immune systems. It recognizes a target, opsonizes it, generates anaphylatoxins, and directly kills cells through the membrane attack complex (MAC). This final function, which assembles C5b-9(n) on viable cell
Qiang Peng et al.
PloS one, 7(10), e47273-e47273 (2012-11-03)
Baboons receiving xenogeneic livers from wild type and transgenic pigs survive less than 10 days. One of the major issues is the early development of profound thrombocytopenia that results in fatal hemorrhage. Histological examination of xenotransplanted livers has shown baboon
Jakyung Yoo et al.
Advances in protein chemistry and structural biology, 87, 219-247 (2012-05-23)
DNA methyltransferases (DNMTs) are promising epigenetic targets for the development of novel anticancer drugs and other diseases. Molecular modeling and experimental approaches are being used to identify and develop inhibitors of human DNMTs. Most of the computational efforts conducted so
Hui-Chen Hung et al.
The Journal of antimicrobial chemotherapy, 65(4), 676-683 (2010-01-22)
Enterovirus 71 (EV71) causes serious diseases in humans. The aim of this study was to examine the effects of aurintricarboxylic acid (ATA) on EV71 replication and to explore the underlying mechanism. To measure the activity of ATA in inhibiting the
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