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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

Key Documents

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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)

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This Item
SML1206T1443S4194
Tyrphostin A9 solid

Sigma-Aldrich

T182

Tyrphostin A9

RA-9 &#8805;98% (HPLC)

Sigma-Aldrich

SML1206

RA-9

TCPOBOP &#8805;98% (HPLC), solid

Sigma-Aldrich

T1443

TCPOBOP

SR 12813 &#8805;98%, solid

Sigma-Aldrich

S4194

SR 12813

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98%

form

solid

form

powder

form

solid

form

solid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

solubility

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

solubility

DMSO: 2 mg/mL, clear (warmed)

solubility

DMSO: >10 mg/mL, H2O: insoluble

solubility

DMSO: ≥10 mg/mL, H2O: insoluble

color

yellow

color

white to beige

color

white

color

-

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

synthetic (organic)

Application

Tyrphostin A9 can be used for inhibiting tyrosine kinase functions in C2C12 cells[1]. It has also been used to disrupt membrane potential in mammalian cells[2].

Biochem/physiol Actions

Tyrphostin A9 is a PDGF receptor tyrosine kinase inhibitor that can induce apoptosis in cancer cells[3], inhibit the growth of vascular smooth cells[4] and block calcium release-dependent phosphorylations[5].

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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Naveen Kumar et al.
Antimicrobial agents and chemotherapy, 55(12), 5553-5559 (2011-09-21)
We have previously reported that two receptor tyrosine kinase inhibitors (RTKIs), called AG879 and tyrphostin A9 (A9), can each block the replication of influenza A virus in cultured cells. In this study, we further characterized the in vitro antiviral efficacies
Tyrphostins as molecular tools and potential antiproliferative drugs.
A Levitzki et al.
Trends in pharmacological sciences, 12(5), 171-174 (1991-05-01)
G E Bilder et al.
The American journal of physiology, 260(4 Pt 1), C721-C730 (1991-04-01)
Tyrphostins are low-molecular-weight synthetic inhibitors of protein tyrosine kinase, which block cell proliferation. Since platelet-derived growth factor (PDGF) is thought to figure prominently in disorders of vascular smooth muscle cells (VSMC), such as atherosclerosis, hypertension, and restenosis, we examined whether
Manuel Fischer et al.
Molecular biology of the cell, 24(14), 2160-2170 (2013-05-17)
Oxidation of cysteine residues to disulfides drives import of many proteins into the intermembrane space of mitochondria. Recent studies in yeast unraveled the basic principles of mitochondrial protein oxidation, but the kinetics under physiological conditions is unknown. We developed assays
Yan-Jun Xu et al.
Journal of cellular and molecular medicine, 12(3), 942-954 (2008-05-23)
Although lysophosphatidic acid (LPA) is known to increase intracellularfree calcium concentration ([Ca(2+)](i)) in different cell types, the effect of LPA on the skeletal muscle cells is not known. The present study was therefore undertaken to examine the effect of LPA
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