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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
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
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biological source

synthetic (organic)

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

yellow

mp

139-140 °C

solubility

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

SMILES string

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

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

InChI key

MZOPWQKISXCCTP-UHFFFAOYSA-N

Gene Information

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

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

Regulatory Information

农药列管产品

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH0037
MKCC5802
MKBZ4365V
MKBV0692V
SLBD5202V

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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
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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Global Trade Item Number

SKUGTIN
SAB1305340-400UL04061835614097
T182-25MG04061832434858
T182-5MG04061832434865