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Merck

T182

Tyrphostin A9

solid

Synonym(s):

Malonoben, [[3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile

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About This Item

Empirical Formula (Hill Notation):
C18H22N2O
CAS Number:
10537-47-0
Molecular Weight:
282.38
NACRES:
NA.77
PubChem Substance ID:
24278069
UNSPSC Code:
51111800
MDL number:
MFCD00209853

Product Name

Tyrphostin A9, solid

InChI

1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3

SMILES string

CC(C)(C)c1cc(\C=C(\C#N)C#N)cc(c1O)C(C)(C)C

InChI key

MZOPWQKISXCCTP-UHFFFAOYSA-N

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

solid

color

yellow

mp

139-140 °C

solubility

ethanol: 20 mg/mL
DMSO: <25 mg/mL
H2O: insoluble

Quality Level

100

Gene Information

human ... EGFR(1956), ORAI1(84876), PDGFRA(5156), PDGFRB(5159)
mouse ... Eef2k(13631), Prkaca(18747), Prkca(18750), Src(20779)

Related Categories

Application

Tyrphostin A9 can be used for inhibiting tyrosine kinase functions in C2C12 cells. It has also been used to disrupt membrane potential in mammalian cells.

Biochem/physiol Actions

Tyrphostin A9 is a PDGF receptor tyrosine kinase inhibitor that can induce apoptosis in cancer cells, inhibit the growth of vascular smooth cells and block calcium release-dependent phosphorylations.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Tyrphostin A9 is soluble in ethanol at 20 mg/ml, in DMSO at a concentration less than 25 mg/ml. It is insoluble in water.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV7328
MKCT9315
MKCS3755
MKCR8771
MKCH0037

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J Thyberg
European journal of cell biology, 76(1), 33-42 (1998-07-03)
To proliferate, vascular smooth muscle cells first convert from a contractile to a synthetic phenotype. Earlier studies indicate that this process is supported by fibronectin and accelerated by platelet-derived growth factor (PDGF). Here, the mechanisms in this transition were further
Naveen Kumar et al.
Journal of virology, 85(6), 2818-2827 (2011-01-07)
Host signaling pathways play important roles in the replication of influenza virus, but their functional effects remain to be characterized at the molecular level. Here we identify two receptor tyrosine kinase inhibitors (RTKIs) of the tyrphostin class that exhibit robust
So Jung Park et al.
Biochemical and biophysical research communications, 408(3), 465-470 (2011-04-30)
Mitochondria dynamics controls not only their morphology but also functions of mitochondria. Therefore, an imbalance of the dynamics eventually leads to mitochondria disruption and cell death. To identify specific regulators of mitochondria dynamics, we screened a bioactive chemical compound library
R Marhaba et al.
Journal of immunology (Baltimore, Md. : 1950), 157(4), 1468-1473 (1996-08-15)
The mechanism by which calcium-depleted intracellular stores may trigger an external calcium influx through a calcium release-activated channel was investigated by analyzing the effects of several protein tyrosine kinase inhibitors on calcium movements in Jurkat T cells. Tyrphostin A9, an
M Zhao et al.
Leukemia, 14(3), 374-378 (2000-03-17)
Somatic mutation of the FLT3 gene, in which the juxtamembrane domain has an internal tandem duplication, is found in 20% of human acute myeloid leukemias and causes constitutive tyrosine phosphorylation of the products. In this study, we observed that the
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