Malonoben

Names

[ Name ]:
Malonoben

[Synonym ]:
(3,5-Di-tert-butyl-4-hydroxybenzyliden)malononitril
2-(3,5-di-tert-butyl-4-hydroxybenzylidene)malononitrile
Malonoben
MFCD00209853
2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
(3,5-Di-tert-butyl-4-hydroxybenzylidene)malononitrile
Tyrphostin AG17
Tyrphostin 9
2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile
[4-Hydroxy-3,5-bis(2-methyl-2-propanyl)benzylidene]malononitrile
GCP 5126
Propanedinitrile, 2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-
(3,5-di-tert-butyl-4-hydroxybenzylidene)propanedinitrile
Caswell No. 291AA
[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
3,5-di-tert-butyl-4-hydroxybenzylidene-malononitrile
tyrphostin A9

Biological Activity

[Description]:

Tyrphostin A9(AG 17), a tyrosine kinase inhibitor, is a potent inducer of mitochondrial fission. Tyrphostin A9 emerged as the most potent and selective of 51 tyrosine kinase inhibitors tested against the TNF-induced respiratory burst. IC50 value: Target: Multi tyrosine kinaseTyrphostin A9 inhibited TNF-induced tyrosine phosphorylation of pyk2 without blocking the cells' bactericidal activity. Tyrphostin A9 is a PDGF receptor tyrosine kinase inhibitor (IC50 = 500 nM). Recent findings suggest that signaling via PDGF receptor tyrosine kinases is not necessary for the shift of the smooth muscle cells from a contractile to a synthetic phenotype. On the other hand these enzymes apparently carry out important functions in the control of intracellular membrane traffic and cell division.

[Related Catalog]:

Research Areas >> Cancer

[References]

[1]. Park SJ, Park YJ, Shin JH, et al. A receptor tyrosine kinase inhibitor, Tyrphostin A9 induces cancer cell death through Drp1 dependent mitochondria fragmentation. Biochem Biophys Res Commun. 2011 May 13;408(3):465-70.

[2]. Richard F. Loeser, Christopher B. Forsyth, Allen M. Samarel et al. Fibronectin Fragment Activation of Proline-rich Tyrosine Kinase PYK2 Mediates Integrin Signals Regulating Collagenase-3 Expression by Human Chondrocytes through a Protein Kinase C-dependent Pathway. The Journal of Biological Chemistry, 2003, 278, 24577-24585.

[3]. Michele Fuortes, Maxine Melchior, Hyunsil Han, et al. Role of the tyrosine kinase pyk2 in the integrin-dependent activation of human neutrophils by TNF. J Clin Invest. 1999;104(3):327-335.

[4]. Johan Thyberg . Tyrphostin A9 and wortmannin perturb the Golgi complex and block proliferation of vascular smooth muscle cells. European Journal of Cell Biology.1998,76(1): 33-42

[5]. R Marhaba, F Mary, C Pelassy, et al. Tyrphostin A9 inhibits calcium release-dependent phosphorylations and calcium entry via calcium release-activated channel in Jurkat T cells. The Journal of Immunology. 1996,157 (4): 1468-1473

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
386.8±37.0 °C at 760 mmHg

[ Melting Point ]:
141-143℃ (ethanol )

[ Molecular Formula ]:
C₁₈H₂₂N₂O

[ Molecular Weight ]:
282.380

[ Flash Point ]:
187.7±26.5 °C

[ Exact Mass ]:
282.173218

[ PSA ]:
67.81000

[ LogP ]:
4.81

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.555

[ Storage condition ]:
Store at RT

[ Water Solubility ]:
ethanol: 20 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OO3737000

CHEMICAL NAME :: Malononitrile, 3,5-di-tert-butyl-4-hydroxybenzylidene-

CAS REGISTRY NUMBER :: 10537-47-0

BEILSTEIN REFERENCE NO. :: 2700764

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H22-N2-O

MOLECULAR WEIGHT :: 282.42

WISWESSER LINE NOTATION :: NCYCN&U1R DQ CX1&1&1 EX1&1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 87 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SPEADM Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740) Volume(issue)/page/year: 78-1,21,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 226 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SPEADM Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740) Volume(issue)/page/year: 74-1,-,1974

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H311-H331

[ Precautionary Statements ]:
P261-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S36/37/39-S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
OO3737000

[ Hazard Class ]:
6.1

[ HS Code ]:
2926909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2926909090

[ Summary ]:
HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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