| Identification | More | [Name]
TYRPHOSTIN A9 | [CAS]
10537-47-0 | [Synonyms]
[[3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXYPHENYL]METHYLENE]-PROPANEDINITRILE
3,5-DI-T-BUTYL-4-HYDROXY-BENZYLIDENEMALONONITRILE
3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENEMALONONITRILE
AG 17
ALPHA-CYANO-(3,5-DI-T-BUTYL-4-HYDROXY)CINNAMONITRILE
CHEMBRDG-BB 5272363
MALONABEN
MALONOBEN
NSC 242557
RARECHEM AL BX 0198
RG 50872
SF 6847
TYRPHOSTIN 9
TYRPHOSTIN A9
TYRPHOSTIN AG 17
TYRPHOSTIN RG 50872
((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene)-propanedinitril
2-((3,5-bis(1,1-dimethyl)-4-hydroxyphenyl)methylene)propanedinitrile
3,5-di-tert-butyl-4-hydroxybenzylidene-malononitril
ent27910 | [Molecular Formula]
C18H22N2O | [MDL Number]
MFCD00209853 | [Molecular Weight]
282.38 | [MOL File]
10537-47-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
141-143℃ (ethanol ) | [Boiling point ]
424.99°C (rough estimate) | [density ]
1.0741 (rough estimate) | [refractive index ]
1.5700 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
ethanol: 20 mg/mL
| [form ]
solid
| [pka]
7.55±0.40(Predicted) | [color ]
yellow
| [biological source]
synthetic (organic) | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [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 | [InChIKey]
MZOPWQKISXCCTP-UHFFFAOYSA-N | [SMILES]
CC(C)(C)c1cc(\C=C(\C#N)C#N)cc(c1O)C(C)(C)C | [CAS DataBase Reference]
10537-47-0(CAS DataBase Reference) | [EPA Substance Registry System]
Malonoben (10537-47-0) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
OO3737000
| [HS Code ]
2926.90.5050 | [HazardClass ]
6.1 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Oral |
| Hazard Information | Back Directory | [Description]
Tyrphostin 9 (10537-47-0) inhibits PDGF receptor tyrosine kinase (IC50?= 1.2 μM)1and is a potent (10 nM) inhibitor of oxidative phosphorylation2. Inhibits cell growth by disrupting mitochondria.3 Tyrphostin 9 perturbs the golgi complex and blocks proliferation of vascular smooth muscle cells.4 | [Uses]
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. | [Uses]
Selective inhibitor of PDGF receptor tyrosine kinase | [Uses]
SF 6847 is an inhibitor of EGFR with IC50 of 460 μM. | [Definition]
ChEBI: Malonoben is an alkylbenzene. It has a role as a geroprotector. | [Production Methods]
Commercial synthesis details for malonoben are not available in open literature but its structure and classification allow its manufacturing process to be inferred from standard industrial practice. Based on its identity its commercial manufacture would have relied on assembling a hindered phenolic precursor (a 3,5 di tert butyl 4 hydroxybenzaldehyde derivative) followed by Knoevenagel type condensation with malononitrile to form the characteristic benzylidene malononitrile scaffold. This type of condensation is widely used in industrial production of substituted malononitriles and requires controlled basic or acidic catalysis to maintain selectivity and prevent side reactions. Final purification, typically crystallisation, would yield technical grade malonoben for formulation. | [General Description]
A selective, cell-permeable, reversible, and substrate competitive inhibitor of the platelet-derived growth factor receptor tyrosine kinase (IC50 = 500 nM). Anti-proliferative agent. Uncoupler of oxidative phosphorylation. Induces apoptosis in vitro and cell growth arrest in NHL cell lines. | [Biological Activity]
Potent uncoupler of oxidative phosphorylation. | [Biochem/physiol Actions]
Cell permeable: yes | [Mechanism of action]
Uncouples respiratory phosphorylation. Stomach and contact action | [storage]
Store at -20°C | [References]
1) Bilder?et al. (1991),?Tyrphostins inhibit PDGF-induced DNA synthesis and associated early events in smooth muscle cells; Am. J. Physiol.,?260?C721
2) Terada?et al. (1981),?The interaction of highly active uncouplers with mitochondria; Biochim. Biophys. Acta,?639?225
3) Burger?et al. (1995),?Tyrphostin AG17, [3,5-Ditert-butyl-4-hydroxybenzylidene)-malononitrile], inhibits cell growth by disrupting mitochondria; Cancer Res.,?55?2794
4) Thyberg?et al. (1998),?Tyrphostin A9 and wortmannin perturb the Golgi complex and block proliferation of vascular smooth muscle cells; Eur. J. Cell Biol.,?76?33 | [Pesticide Type]
Insecticide; Acaricide |
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